Oleo Chemistry

Badrla Sandeep

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Contents
Articles
Oleochemistry 1
Oleochemical 1
Fatty acid 2
Fatty alcohol 9
Fatty acid methyl ester 14
Monoglyceride 14
Diglyceride 15
Triglyceride 17
Quaternary ammonium cation 23
Oil 25
Fat 27
Soap 30
Cosmetics 38
Vegetable fats and oils 51
Palm oil 59
Transesterification 71
Hydrogenation 73
Saponification 81

References
Article Sources and Contributors 85
Image Sources, Licenses and Contributors 89

Article Licenses
License 91
Oleochemistry 1

Oleochemistry
Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and
oils or from petrochemical feedstocks through physico-chemical modifications or transformation. First used in the
making of soaps, oleochemistry is now part of our daily lives where it is found in a wide variety of sectors like food,
cosmetics, pharmaceutical and industrial.

Oleochemical
Oleochemicals are chemicals derived from plant and animal fats. They are analogous to petrochemicals derived
from petroleum.
The formation of basic oleochemical substances like fatty acids, fatty acid methyl esters (FAME), fatty alcohols,
fatty amines and glycerols are by various chemical and enzymatic reactions. Intermediate chemical substances
produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether
sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols
(TAG), sugar esters, and other oleochemical products.
As the price of crude oil rose in the late 1970s,[1] manufacturers switched from petrochemicals to oleochemicals[2]
because plant-based lauric oils processed from palm kernel oil were cheaper. Since then, palm kernel oil is
predominantly used in the production of laundry detergent and personal care items like toothpaste, soap bars, shower
cream and shampoo.[3]

Industry in Asia
Southeast Asian countries' rapid production growth of palm oil and palm kernel oil in the 1980s spurred the
oleochemical industry in Malaysia, Indonesia, and Thailand. Many oleochemical plants were built. Though a nascent
and small industry when pitted against big detergent giants in the US and Europe, oleochemical companies in
southeast Asia had competitive edge in cheap ingredients.[4] The US fatty chemical industry found it difficult to
consistently maintain acceptable levels of profits. Competition was intense with market shares divided among many
companies there where neither imports nor exports played a significant role.[5] By the late 1990s, giants like Henkel,
Unilever, and Petrofina sold their oleochemical factories to focus on higher profit activities like retail of consumer
goods. Since the Europe outbreak of 'mad cow disease' or (bovine spongiform encephalopathy) in 2000, tallow is
replaced for many uses by vegetable oleic fatty acids, such as palm kernel and coconut oils.[6]

Applications
The most common application of oleochemicals is biodiesel production. Fatty acids are esterified with an alcohol,
commonly methanol to form methyl esters. Another common application is in the production of detergents. Lauric
acid is used to produce sodium lauryl sulfate, the main ingredient in many personal care products. Other applications
include the production of lubricants, green solvents, and bioplastics.

Hydrolysis
The fat splitting (or hydrolysis) of the triglycerides produces fatty acids and glycerol:
RCOOCH2–CHOOCR–CH2OCOR + 3 H2O → 3 RCOOH + HOCH2–CHOH–CH2OH
The addition of base helps the reaction proceed more quickly.
Oleochemical 2

Transesterification
If oils or fats are made to react with an alcohol (R'OH) instead of with water, the process is alcoholysis. It is also
called transesterification, because the glycerol fragment of the fatty acid tri-ester is exchanged for that of another
alcohol. Thus, the products are fatty acid esters and glycerol:
RCOOCH2–CHOOCR–CH2OCOR + 3 R'OH → 3 RCOOR' + HOCH2–CHOH–CH2OH
The fatty acid or fatty esters produced by these methods may be transformed. For example, hydrogenation converts
unsaturated fatty acids into saturated fatty acids. The acids or esters can also be reduced to give fatty alcohols.

References
[1] Haupt, D. E.; Drinkard, G.; Pierce, H. F. (1984). "Future of petrochemical raw materials in oleochemical markets". Journal of the American
Oil Chemists' Society 61 (2): 276. doi:10.1007/BF02678781.
[2] Akaike, Yoshiteru (1985). "Other oleochemical uses: Palm oil products". Journal of the American Oil Chemists' Society 62 (2): 335.
doi:10.1007/BF02541401.
[3] Dewaet, F. (1985). "Quality requirements from a consumer’s point of view (oleochemical products)". Journal of the American Oil Chemists'
Society 62 (2): 366. doi:10.1007/BF02541406.
[4] The future of palm oil in oleochemicals (http:/ / palmoilis. mpob. gov. my/ publications/ pod14-3. pdf) Appalasami & de Vries, Palm Oil
Developments 14-3, 1990
[5] Leonard, E. Charles; Kapald, S L (1984). "Challenges to a mature industry: Marketing and economics of oleochemicals in the United States".
Journal of the American Oil Chemists' Society 61 (2): 176. doi:10.1007/BF02678763.
[6] The Changing World of Oleochemicals (http:/ / palmoilis. mpob. gov. my/ publications/ pod44-wolfgang. pdf) Wolfgang Rupilius and
Salmiah Ahmad, Palm Oil Developments 44, 2005

Fatty acid
In chemistry, especially biochemistry, a fatty acid is a carboxylic acid
with a long aliphatic tail (chain), which is either saturated or
unsaturated. Most naturally occurring fatty acids have a chain of an
even number of carbon atoms, from 4 to 28.[1] Fatty acids are usually
derived from triglycerides or phospholipids. When they are not
attached to other molecules, they are known as "free" fatty acids. Fatty
acids are important sources of fuel because, when metabolized, they
Butyric acid, a short-chain fatty acid
yield large quantities of ATP. Many cell types can use either glucose or
fatty acids for this purpose. In particular, heart and skeletal muscle
prefer fatty acids. The brain cannot use fatty acids as a source of fuel; it relies on glucose or ketone bodies.[2]
Fatty acid 3

Types of fatty acids

Fatty acids that have double bonds are
known as unsaturated. Fatty acids without
double bonds are known as saturated. They
differ in length as well.

Length of free fatty acid chains

Fatty acid chains differ by length, often
categorized as short, medium, or long.
• Short-chain fatty acids (SCFA) are fatty
acids with aliphatic tails of fewer than six
carbons (i.e. butyric acid).
• Medium-chain fatty acid (MCFA) are
fatty acids with aliphatic tails of 6–12[3]
carbons, which can form medium-chain Three dimensional representations of several fatty acids
triglycerides.
• Long-chain fatty acid (LCFA) are fatty acids with aliphatic tails longer than 12 carbons.[4]
• Very long chain fatty acid (VLCFA) are fatty acids with aliphatic tails longer than 22 carbons

Unsaturated fatty acids

Unsaturated fatty acids have one or more
double bonds between carbon atoms. (Pairs
of carbon atoms connected by double bonds
can be saturated by adding hydrogen atoms
to them, converting the double bonds to
single bonds. Therefore, the double bonds
are called unsaturated.)

The two carbon atoms in the chain that are

bound next to either side of the double bond
can occur in a cis or trans configuration.
cis
A cis configuration means that
adjacent hydrogen atoms are on the
same side of the double bond. The
rigidity of the double bond freezes its Comparison of the trans isomer (top) Elaidic acid and the cis-isomer oleic acid.
conformation and, in the case of the
cis isomer, causes the chain to bend and restricts the conformational freedom of the fatty acid. The more
double bonds the chain has in the cis configuration, the less flexibility it has. When a chain has many cis
bonds, it becomes quite curved in its most accessible conformations. For example, oleic acid, with one double
bond, has a "kink" in it, whereas linoleic acid, with two double bonds, has a more pronounced bend.
Alpha-linolenic acid, with three double bonds, favors a hooked shape. The effect of this is that, in restricted
environments, such as when fatty acids are part of a phospholipid in a lipid bilayer, or triglycerides in lipid
droplets, cis bonds limit the ability of fatty acids to be closely packed, and therefore could affect the melting
temperature of the membrane or of the fat.
 Fatty acid 4

trans
A trans configuration, by contrast, means that the next two hydrogen atoms are bound to opposite sides of the
double bond. As a result, they do not cause the chain to bend much, and their shape is similar to straight
saturated fatty acids.
In most naturally occurring unsaturated fatty acids, each double bond has three n carbon atoms after it, for some n,
and all are cis bonds. Most fatty acids in the trans configuration (trans fats) are not found in nature and are the result
of human processing (e.g., hydrogenation).
The differences in geometry between the various types of unsaturated fatty acids, as well as between saturated and
unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures
(such as cell membranes).

Examples of Unsaturated Fatty Acids

Common Chemical structure Δx C:D n−x
name

Myristoleic CH3(CH2)3CH=CH(CH2)7COOH cis-Δ9 14:1 n−5

acid

Palmitoleic CH3(CH2)5CH=CH(CH2)7COOH cis-Δ9 16:1 n−7

acid

Sapienic acid CH3(CH2)8CH=CH(CH2)4COOH cis-Δ6 16:1 n−10

Oleic acid CH3(CH2)7CH=CH(CH2)7COOH cis-Δ9 18:1 n−9

Elaidic acid CH3(CH2)7CH=CH(CH2)7COOH trans-Δ9 18:1 n−9

Vaccenic acid CH3(CH2)5CH=CH(CH2)9COOH trans-Δ11 18:1 n−7

Linoleic acid CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH cis,cis-Δ9,Δ12 18:2 n−6

Linoelaidic CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH trans,trans-Δ9,Δ12 18:2 n−6

acid

α-Linolenic CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH cis,cis,cis-Δ9,Δ12,Δ15 18:3 n−3

acid

Arachidonic NIST [5] 5 8 11 14 20:4 n−6

CH (CH ) CH=CHCH CH=CHCH CH=CHCH CH=CH(CH ) COOH cis,cis,cis,cis-Δ Δ ,Δ ,Δ
3 2 4 2 2 2 2 3
acid

EicosapentaenoicCH CH CH=CHCH CH=CHCH CH=CHCH CH=CHCH CH=CH(CH ) COOH 5 8 11

cis,cis,cis,cis,cis-Δ ,Δ ,Δ ,Δ ,Δ
14 17 20:5 n−3
3 2 2 2 2 2 2 3
acid

Erucic acid CH3(CH2)7CH=CH(CH2)11COOH cis-Δ13 22:1 n−9

DocosahexaenoicCH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)2COOH cis,cis,cis,cis,cis,cis-Δ4,Δ7,Δ10,Δ13,Δ16,Δ19 22:6 n−3

acid

Essential fatty acids

Fatty acids that are required by the human body but cannot be made in sufficient quantity from other substrates, and
therefore must be obtained from food, are called essential fatty acids. There are two series of essential fatty acids:
one has a double bond three carbon atoms removed from the methyl end; the other has a double bond six carbon
atoms removed from the methyl end. Humans lack the ability to introduce double bonds in fatty acids beyond
carbons 9 and 10, as counted from the carboxylic acid side.[6] Two essential fatty acids are linoleic acid (LA) and
alpha-linolenic acid (ALA). They are widely distributed in plant oils. The human body has a limited ability to
convert ALA into the longer-chain n-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA),
Fatty acid 5

which can also be obtained from fish.

Saturated fatty acids

Saturated fatty acids are long-chain carboxylic acids that usually have between 12 and 24 carbon atoms and have no
double bonds. Thus, saturated fatty acids are saturated with hydrogen (since double bonds reduce the number of
hydrogens on each carbon). Because saturated fatty acids have only single bonds, each carbon atom within the chain
has 2 hydrogen atoms (except for the omega carbon at the end that has 3 hydrogens).

Examples of Saturated Fatty Acids

Common name Chemical structure C:D

Caprylic acid CH3(CH2)6COOH 8:0

Capric acid CH3(CH2)8COOH 10:0

Lauric acid CH3(CH2)10COOH 12:0

Myristic acid CH3(CH2)12COOH 14:0

Palmitic acid CH3(CH2)14COOH 16:0

Stearic acid CH3(CH2)16COOH 18:0

Arachidic acid CH3(CH2)18COOH 20:0

Behenic acid CH3(CH2)20COOH 22:0

Lignoceric acid CH3(CH2)22COOH 24:0

Cerotic acid CH3(CH2)24COOH 26:0

Nomenclature
Several different systems of
nomenclature are used for fatty acids.
The following table describes the most
common systems. Numbering of carbon atoms

System Example Explanation

Trivial Palmitoleic acid Trivial names (or common names) are non-systematic historical names, which are the most
nomenclature frequent naming system used in literature. Most common fatty acids have trivial names in addition
to their systematic names (see below). These names frequently do not follow any pattern, but they
are concise and often unambiguous.

Systematic (9Z)-octadecenoic acid Systematic names (or IUPAC names) derive from the standard IUPAC Rules for the Nomenclature
nomenclature [7]
of Organic Chemistry, published in 1979, along with a recommendation published specifically for
[8]
lipids in 1977. Counting begins from the carboxylic acid end. Double bonds are labelled with
cis-/trans- notation or E-/Z- notation, where appropriate. This notation is generally more verbose
than common nomenclature, but has the advantage of being more technically clear and descriptive.

Δx cis,cis-Δ9,Δ12 In Δx (or delta-x) nomenclature, each double bond is indicated by Δx, where the double bond is
nomenclature octadecadienoic acid located on the xth carbon–carbon bond, counting from the carboxylic acid end. Each double bond is
preceded by a cis- or trans- prefix, indicating the conformation of the molecule around the bond. For
example, linoleic acid is designated "cis-Δ9, cis-Δ12 octadecadienoic acid". This nomenclature has
the advantage of being less verbose than systematic nomenclature, but is no more technically clear
or descriptive.
Fatty acid 6

n−x n−3 n−x (n minus x; also ω−x or omega-x) nomenclature both provides names for individual
nomenclature compounds and classifies them by their likely biosynthetic properties in animals. A double bond is
located on the xth carbon–carbon bond, counting from the terminal methyl carbon (designated as n or
ω) toward the carbonyl carbon. For example, α-Linolenic acid is classified as a n−3 or omega-3 fatty
acid, and so it is likely to share a biosynthetic pathway with other compounds of this type. The ω−x,
omega-x, or "omega" notation is common in popular nutritional literature, but IUPAC has
[7]
deprecated it in favor of n−x notation in technical documents. The most commonly researched
fatty acid biosynthetic pathways are n−3 and n−6, which are hypothesized to decrease or increase,
respectively, inflammation.

Lipid numbers 18:3 Lipid numbers take the form C:D, where C is the number of carbon atoms in the fatty acid and D is
18:3, n−6 the number of double bonds in the fatty acid. This notation can be ambiguous, as some different
18:3, cis,cis,cis-Δ9,Δ12,Δ15 fatty acids can have the same numbers. Consequently, when ambiguity exists this notation is usually
[7]
paired with either a Δx or n−x term.

Production
Fatty acids are usually produced industrially by the hydrolysis of triglycerides, with the removal of glycerol (see
oleochemicals). Phospholipids represent another source. Some fatty acids are produced synthetically by
hydrocarboxylation of alkenes.

Free fatty acids

The biosynthesis of fatty acids involves the condensation of acetyl-CoA. Since this coenzyme carries a
two-carbon-atom group, almost all natural fatty acids have even numbers of carbon atoms.
The "uncombined fatty acids" or "free fatty acids" found in organisms come from the breakdown of a triglyceride.
Because they are insoluble in water, these fatty acids are transported (solubilized, circulated) while bound to plasma
protein albumin. The levels of "free fatty acid" in the blood are limited by the availability of albumin binding sites.

Fatty acids in dietary fats

The following table gives the fatty acid, vitamin E and cholesterol composition of some common dietary fats.[9] [10]

Saturated Monounsaturated Polyunsaturated Cholesterol Vitamin E

g/100g g/100g g/100g mg/100g mg/100g

Animal fats

Lard 40.8 43.8 9.6 93 0.00

[11] 33.2 49.3 12.9 100 2.70

Duck fat

Butter 54.0 19.8 2.6 230 2.00

Vegetable fats

Coconut oil 85.2 6.6 1.7 0 .66

Palm oil 45.3 41.6 8.3 0 33.12

Cottonseed oil 25.5 21.3 48.1 0 42.77

Wheat germ oil 18.8 15.9 60.7 0 136.65

Soya oil 14.5 23.2 56.5 0 16.29

Olive oil 14.0 69.7 11.2 0 5.10

Corn oil 12.7 24.7 57.8 0 17.24

Sunflower oil 11.9 20.2 63.0 0 49.0

Fatty acid 7

Safflower oil 10.2 12.6 72.1 0 40.68

Hemp oil 10 15 75 0

Canola/Rapeseed oil 5.3 64.3 24.8 0 22.21

Reactions of fatty acids

Fatty acids exhibit reactions like other carboxylic acid, i.e. they undergo esterification and acid-base reactions.

Acidity
Fatty acids do not show a great variation in their acidities, as indicated by their respective pKa. Nonanoic acid, for
example, has a pKa of 4.96, being only slightly weaker than acetic acid (4.76). As the chain length increases the
solubility of the fatty acids in water decreases very rapidly, so that the longer-chain fatty acids have minimal effect
on the pH of an aqueous solution. Even those fatty acids that are insoluble in water will dissolve in warm ethanol,
and can be titrated with sodium hydroxide solution using phenolphthalein as an indicator to a pale-pink endpoint.
This analysis is used to determine the free fatty acid content of fats; i.e., the proportion of the triglycerides that have
been hydrolyzed.

Hydrogenation and hardening

Hydrogenation of unsaturated fatty acids is widely practiced to give saturated fatty acids, which are less prone
toward rancidification. Since the saturated fatty acids are higher melting than the unsaturated relatives, the process is
called hardening. This technology is used to convert vegetable oils into margarine. During partial hydrogenation,
unsaturated fatty acids can be isomerized from cis to trans configuration.[12]
More forcing hydrogenation, i.e. using higher pressures of H2 and higher temperatures, converts fatty acids into fatty
alcohols. Fatty alcohols are, however, more easily produced from fatty acid esters.
In the Varrentrapp reaction certain unsaturated fatty acids are cleaved in molten alkali, a reaction at one time of
relevance to structure elucidation.

Auto-oxidation and rancidity

Unsaturated fatty acids undergo a chemical change known as auto-oxidation. The process requires oxygen (air) and
is accelerated by the presence of trace metals. Vegetable oils resists this process because they contain antioxidants,
such as tocopherol. Fats and oils often are treated with chelating agents such as citric acid to remove the metal
catalysts.

Ozonolysis
Unsaturated fatty acids are susceptible to degradation by ozone. This reaction is practiced in the production of
azelaic acid ((CH2)7(CO2H)2) from oleic acid.[12]

Circulation

Digestion and intake

Short- and medium-chain fatty acids are absorbed directly into the blood via intestine capillaries and travel through
the portal vein just as other absorbed nutrients do. However, long-chain fatty acids are not directly released into the
intestinal capillaries. Instead they are absorbed into the fatty walls of the intestine villi and reassembled again into
triglycerides. The triglycerides are coated with cholesterol and protein (protein coat) into a compound called a
chylomicron.
Fatty acid 8

Within the villi, the chylomicron enters a lymphatic capillary called a lacteal, which merges into larger lymphatic
vessels. It is transported via the lymphatic system and the thoracic duct up to a location near the heart (where the
arteries and veins are larger). The thoracic duct empties the chylomicrons into the bloodstream via the left subclavian
vein. At this point the chylomicrons can transport the triglycerides to tissues where they are stored or metabolized for
energy.

Metabolism
Fatty acids (provided either by ingestion or by drawing on triglycerides stored in fatty tissues) are distributed to cells
to serve as a fuel for muscular contraction and general metabolism. They are consumed by mitochondria to produce
ATP through beta oxidation.

Distribution
Blood fatty acids are in different forms in different stages in the blood circulation. They are taken in through the
intestine in chylomicrons, but also exist in very low density lipoproteins (VLDL) and low density lipoproteins (LDL)
after processing in the liver. In addition, when released from adipocytes, fatty acids exist in the blood as free fatty
acids.
It is proposed that the blend of fatty acids exuded by mammalian skin, together with lactic acid and pyruvic acid, is
distinctive and enables animals with a keen sense of smell to differentiate individuals.[13]

References
[1] IUPAC Compendium of Chemical Terminology (http:/ / goldbook. iupac. org/ F02330. html) (2nd ed.). International Union of Pure and
Applied Chemistry. 1997. ISBN 0-521-51150-X. . Retrieved 2007-10-31.
[2] Mary K. Campbell, Shawn O. Farrell (2006). Biochemistry (5th ed.). Cengage Learning. p. 579. ISBN 0-534-40521-5.
[3] Medscape: Free CME, Medical News, Full-text Journal Articles & More (http:/ / emedicine. medscape. com/ article/ 946755-overview)
[4] Christopher Beermann1, J Jelinek1, T Reinecker2, A Hauenschild2, G Boehm1, and H-U Klör2, " Short term effects of dietary medium-chain
fatty acids and n-3 long-chain polyunsaturated fatty acids on the fat metabolism of healthy volunteers (http:/ / lipidworld. com/ content/ 2/ 1/
10)"
[5] http:/ / webbook. nist. gov/ cgi/ cbook. cgi?Name=Arachidonic+ Acid& Units=SI
[6] Cell Biology: A Short Course (http:/ / books. google. com/ books?id=3a6p9pA5gZ8C& pg=PA42)
[7] Rigaudy, J.; Klesney, S.P. (1979). Nomenclature of Organic Chemistry. Pergamon. ISBN 0-08-022369-9. OCLC 5008199.
[8] "The Nomenclature of Lipids. Recommendations, 1976" (http:/ / www. blackwell-synergy. com/ doi/ pdf/ 10. 1111/ j. 1432-1033. 1977.
tb11778. x). European Journal of Biochemistry 79 (1): 11–21. 1977. doi:10.1111/j.1432-1033.1977.tb11778.x. .
[9] Food Standards Agency (1991). "Fats and Oils". McCance & Widdowson's the Composition of Foods. Royal Society of Chemistry.
[10] Ted Altar. "More Than You Wanted To Know About Fats/Oils" (http:/ / www. efn. org/ ~sundance/ fats_and_oils. html). Sundance Natural
Foods Online. . Retrieved 2006-08-31.
[11] U. S. Department of Agriculture.. "USDA National Nutrient Database for Standard Reference" (http:/ / www. nal. usda. gov/ fnic/
foodcomp/ search/ ). U. S. Department of Agriculture.. . Retrieved 2010-02-17.
[12] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia
of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
[13] "Electronic Nose Created To Detect Skin Vapors" (http:/ / www. sciencedaily. com/ releases/ 2009/ 07/ 090721091839. htm). Science Daily.
July 21, 2009. . Retrieved 2010-05-18.
Fatty acid 9

External links
• Lipid Library ([Link]
• Prostaglandins, Leukotrienes & Essential Fatty Acids Journal ([Link]
• Fatty Blood Acids ([Link]

Fatty alcohol
Fatty alcohols are aliphatic alcohols consisting of a chain of 8 to 22
carbon atoms. Fatty alcohols usually have even number of carbon
atoms and a single alcohol group (-OH) attached to the terminal
carbon. Some are unsaturated and some are branched. They are widely
used in industrial chemistry.

Production and occurrence

Fatty alcohol
Most fatty alcohols in nature are found as waxes which are esters with
fatty acids and fatty alcohols.[1] They are produced by bacteria, plants and animals for purposes of buoyancy, as
source of metabolic water and energy, biosonoar lenses (marine mammals) and for thermal insulation in the form of
waxes (in plants and insects).[2] Fatty alcohols were unavailable until the early 1900s. They were originally obtained
by reduction of wax esters with sodium by the Bouveault–Blanc reduction process. In the 1930s catalytic
hydrogenation was commercialized, which allowed the conversion of fatty acid esters, typically tallow, to the
alcohols. In the 1940s and 1950s, petrochemicals became an important source of chemicals, and Karl Ziegler had
discovered the polymerization of ethylene. These two developments opened the way to synthetic fatty alcohols.

From natural sources

The traditional and still important source of fatty alcohols are fatty acid esters. Wax esters were formerly extracted
from sperm oil, obtained from whales. An alternative plant source is jojoba. Fatty acid triesters, known as
triglycerides, are obtained from plant and animal sources. These triesters are subjected to transesterification to give
methyl esters, which in turn are hydrogenated to the alcohols. Although tallow is typically C16-C18, the chain length
from plant sources are more variable. Higher alcohols (C20–C22) can be obtained from rapeseed. Shorter alcohols
(C12-C14) are obtained from coconut oil.

From petrochemical sources

Fatty alcohols are also prepared from petrochemical sources. In the Ziegler process, ethylene is oligomerized using
triethylaluminium followed by air oxidation. This process affords even-numbered alcohols:
Al(C2H5)3 + 18 C2H4 → Al(C14H29)3
Al(C14H29)3 + 1.5 O2 + 1.5 H2O → 3 HOC14H29 + 0.5 Al2O3
Alternatively ethylene can be oligomerized to give mixtures of alkenes, which are subjected to hydroformylation,
this process affording odd-numbered aldehyde, which is subsequently hydrogenated. For example, from 1-decene,
hydroformylation gives the C11 alcohol:
C8H17CH=CH2 + H2 + CO → C8H17CH2CH2CHO
C8H17CH2CH2CHO + H2 → C8H17CH2CH2CH2OH
In the Shell higher olefin process, the chain-length distribution in the initial mixture of alkene oligomers is adjusted
so as to more closely match market demand. Shell does this by means of an intermediate metathesis reaction.[3] The
Fatty alcohol 10

resultant mixture is fractionated and hydroformylated/hydrogenated in a subsequent step.

Applications
Fatty alcohols are mainly used in the production of detergents and surfactants. They are components also of
cosmetics, foods, and as industrial solvents. Due to their amphipathic nature, fatty alcohols behave as nonionic
surfactants. They find use as emulsifiers, emollients and thickeners in cosmetics and food industry.

Nutrition
Very long chain fatty alcohols (VLCFA), obtained from plant waxes and beeswax have been reported to lower
plasma cholesterol in humans. They can be found in unrefined cereal grains, beeswax, and many plant-derived foods.
Reports suggest that 5–20 mg per day of mixed C24–C34 alcohols, including octacosanol and triacontanol, lower
low-density lipoprotein (LDL) cholesterol by 21%–29% and raise high-density lipoprotein cholesterol by 8%–15%.
Wax esters are hydrolyzed by a bile salt–dependent pancreatic carboxyl esterase, releasing long chain alcohols and
fatty acids that are absorbed in the gastrointestinal tract. Studies of fatty alcohol metabolism in fibroblasts suggest
that very long chain fatty alcohols, fatty aldehydes, and fatty acids are reversibly inter-converted in a fatty alcohol
cycle. The metabolism of these compounds is impaired in several inherited human peroxisomal disorders, including
adrenoleukodystrophy and Sjögren-Larsson syndrome.[4]

Safety

Exposure
Exposure could occur with commercial application in the manufacturing (such as in production and formulation) or
with use of the final product. Hazards are mitigated in industry by following information found in material safety
data sheets.

Human Health
Tests of acute and repeated exposures have revealed a low level of toxicity from inhalation, oral or dermal exposure
of fatty alcohols. Fatty alcohols are not very volatile and the acute lethal concentration is greater than the saturated
vapor pressure. Longer chain (C12-C16) fatty alcohols produce less health effects than short chain (< C12). Short
chain fatty alcohols are considered eye irritants, while long chain alcohols are not.[5] There is no skin sensitization
potential from fatty alcohols.[6]
Repeated exposure to fatty alcohols produce low level toxicity and certain compounds in this category can cause
local irritation on contact or low-grade liver effects (essentially linear alcohols have a slightly higher rate of
occurrence of these effects). No effects on the central nervous system have been seen with inhalation and oral
exposure. Tests of repeated bolus dosages of 1-hexanol and 1-octanol showed potential for CNS depression and
induced respiratory distress. No potential for peripheral neuropathy has been found. In rats, the no observable
adverse effect level (NOAEL) ranges from 200 mg/kg/day to 1000 mg/kg/day by ingestion. There has been no
evidence that fatty alcohols are carcinogenic, mutagenic, or cause reproductive toxicity or [Link] alcohols
are effectively eliminated from the body when exposed, limiting possibility of retention or bioaccumulation.[]
Margins of exposure resulting from consumer uses of these chemicals are adequate for the protection of human
health as determined by the Organization for Economic Co-operation and Development (OECD) high production
volume chemicals program.[5][7]
Fatty alcohol 11

Environment
Fatty alcohols up to chain length C18 are biodegradable, with length up to C16 biodegrading within 10 days
completely. Chains C16 to C18 were found to biodegrade from 62% to 76% in 10 days. Chains greater than C18
were found to degrade by 37% in 10 days. Field studies at waste-water treatment plants have shown that 99% of fatty
alcohols lengths C12-C18 are removed.[]
Fate prediction using Fugacity modeling has shown that fatty alcohols with chain lengths of C10 and greater in water
partition into sediment. Lengths C14 and above are predicted to stay in the air upon release. Modeling shows that
each type of fatty alcohol will respond independently upon environmental release.[]

Aquatic Organisms
Fish, invertebrates and algae experience similar levels of toxicity with fatty alcohols although it is dependent on
chain length with the shorter chain having greater toxicity potential. Longer chain lengths show no toxicity to aquatic
organisms.[]

Chain Size Acute Toxicity Chronic Toxicity

< C11 1–100 mg/l 0.1-1.0 mg/l

C11-C13 0.1-1.0 mg/l 0.1 - <1.0 mg/l

C14-C15 NA 0.01 mg/l

>C16 NA NA

This category of chemicals was evaluated under the Organization for Economic Co-operation and Development
(OECD) high production volume chemicals program. No unacceptable environmental risks were identified.[7]

Common names and related compounds

Name Carbon atoms Branches/saturated? Formula

capryl alcohol (1-octanol) 8 carbon atoms

2-ethyl hexanol 8 carbon atoms branched

pelargonic alcohol (1-nonanol) 9 carbon atoms

capric alcohol (1-decanol, decyl alcohol) 10 carbon

atoms

Undecyl alcohol (1-undecanol, undecanol, 11 carbon

Hendecanol) atoms

Lauryl alcohol (Dodecanol, 1-dodecanol) 12 carbon

atoms

Tridecyl alcohol (1-tridecanol, tridecanol, 13 carbon

isotridecanol) atoms

Myristyl alcohol (1-tetradecanol) 14 carbon

atoms

Pentadecyl alcohol (1-pentadecanol, pentadecanol) 15 carbon

atoms

cetyl alcohol (1-hexadecanol) 16 carbon

atoms

palmitoleyl alcohol (cis-9-hexadecen-1-ol) 16 carbon unsaturated CH3(CH2)5CH=CH(CH2)8OH

atoms
Fatty alcohol 12

Heptadecyl alcohol (1-n-heptadecanol, heptadecanol) 17 carbon

atoms

stearyl alcohol (1-octadecanol) 18 carbon

atoms

isostearyl alcohol (16-methylheptadecan-1-ol) 18 carbon branched (CH3)2CH-(CH2)15OH

atoms

elaidyl alcohol (9E-octadecen-1-ol) 18 carbon unsaturated CH3(CH2)7CH=CH(CH2)8OH

atoms

oleyl alcohol (cis-9-octadecen-1-ol) 18 carbon unsaturated

atoms

linoleyl alcohol (9Z, 12Z-octadecadien-1-ol) 18 carbon polyunsaturated,

atoms a hydrolyzation of linoleic
acid,
an omega 6 fatty acid

elaidolinoleyl alcohol (9E, 12E-octadecadien-1-ol) 18 carbon polyunsaturated

atoms

linolenyl alcohol (9Z, 12Z, 15Z-octadecatrien-1-ol) 18 carbon polyunsaturated

atoms

elaidolinolenyl alcohol (9E, 12E, 18 carbon polyunsaturated

15-E-octadecatrien-1-ol) atoms

ricinoleyl alcohol (12-hydroxy-9-octadecen-1-ol) 18 carbon unsaturated, diol CH3(CH2)5CH(OH)CH2CH=CH(CH2)8OH

atoms

Nonadecyl alcohol (1-nonadecanol) 19 carbon

atoms

arachidyl alcohol (1-eicosanol) 20 carbon

atoms

Heneicosyl alcohol (1-heneicosanol) 21 carbon

atoms

behenyl alcohol (1-docosanol) 22 carbon

atoms

erucyl alcohol (cis-13-docosen-1-ol) 22 carbon unsaturated CH3(CH2)7CH=CH(CH2)12OH

atoms

lignoceryl alcohol (1-tetracosanol) 24 carbon

atoms

ceryl alcohol (1-hexacosanol) 26 carbon

atoms

1-heptacosanol 27 carbon
atoms

montanyl alcohol, cluytyl alcohol (1-octacosanol) 28 carbon

atoms

1-nonacosanol 29 carbon
atoms

myricyl alcohol, melissyl alcohol (1-triacontanol) 30 carbon

atoms

1-dotriacontanol 32 carbon
atoms

geddyl alcohol (1-tetratriacontanol) 34 carbon

atoms
Fatty alcohol 13

Cetearyl alcohol

Behenyl alcohol, lignoceryl alcohol, ceryl alcohol, 1-heptacosanol, montanyl alcohol, 1-nonacosanol, myricyl
alcohol, 1-dotriacontanol, and geddyl alcohol are together classified as policosanol, with montanyl alcohol and
myricyl alcohol being the most abundant.

References
[1] Klaus Noweck, Wolfgang Grafahrend, "Fatty Alcohols" in Ullmann’s Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim.
[2] Stephen Mudge; Wolfram Meier-Augenstein, Charles Eadsforth and Paul DeLeo (2010). "What contribution do detergent fatty alcohols make
to sewage discharges and the maine environment?". Journal of Environmental Monitoring: 1846–1856. doi:10.1039/C0EM00079E.
[3] Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 6706-6711
[4] Nutritional Significance and Metabolism of Very Long Chain Fatty Alcohols and Acids from Dietary Waxes - Hargrove et al. 229 (3): 215 -
Experimental Biology and Medicine (http:/ / www. ebmonline. org/ cgi/ content/ abstract/ 229/ 3/ 215)
[5] Veenstra, Gauke; Catherine Webb, Hans Sanderson, Scott E. Belanger, Peter Fisk, Allen Nielson, Yutaka Kasai, Andreas Willing, Scott Dyer,
David Penney, Hans Certa, Kathleen Stanton, Richard Sedlak (2009). "Human health risk assessment of long chain alcohols". Ecotoxicology
and Environmental Safety: 1016–1030. doi:10.1016/[Link].2008.07.012.
[6] UK/ICCA (2006). "SIDS Initial Assessment Profile" (http:/ / webnet. oecd. org/ hpv/ UI/ handler.
axd?id=03441f78-d135-4cab-b832-edfb1d0d677e). OECD Existing Chemicals Database. .
[7] Sanderson, Hans; Scott E. Belanger, Peter R. Fisk, Christoph Schäfers, Gauke Veenstra, Allen M. Nielsen, Yutaka Kasai, Andreas Willing,
Scott D. Dyer, Kathleen Stanton, Richard Sedlak, (May 2009). "An overview of hazard and risk assessment of the OECD high production
volume chemical category—Long chain alcohols [C6–C22] (LCOH)". Ecotoxicology and Environmental Safety 72 (4): 973–979.
doi:10.1016/[Link].2008.10.006.

External links
• Cyberlipid. "Fatty Alcohols and Aldehydes" ([Link] Retrieved
2007-02-06. General overview of fatty alcohols, with references.
• CONDEA. "Dr. Z Presents All about fatty alcohols" ([Link] pdfs/articles/
All about fatty alcohols [Link]). Retrieved 2007-02-06.
Fatty acid methyl ester 14

Fatty acid methyl ester

Fatty acid methyl esters (FAME) are a type of fatty acid ester than can be produced by an alkali-catalyzed reaction
between fats or fatty acids and methanol. The molecules in biodiesel are primarily FAMEs, usually obtained from
vegetable oils by transesterification.
Since every microorganism has its specific FAME profile (microbial
fingerprinting), it can be used as a tool for microbial source tracking
(MST). The types and proportions of fatty acids present in cytoplasm
membrane and outer membrance (gram negative) lipids of cells are
major phenotypic trains.
Clinical analysis can determine the lengths, bonds, rings and branches of the FAME. To perform this analysis, a
bacterial culture is taken, and the fatty acids extracted and used to form methyl esters. The volatile derivatives are
then introduced into a gas chromatagraph, and the patterns of the peaks help identify the organism. This is widely
used in characterizing new species of bacteria, and is useful for identifying pathogenic strains.

Monoglyceride
A monoglyceride, more correctly known as a monoacylglycerol, is a
glyceride consisting of one fatty acid chain covalently bonded to a glycerol
molecule through an ester linkage.[1]
Monoacylglycerol can be broadly divided into two groups;
1-monoacylglycerols and 2-monoacylglycerols, depending on the position of
General chemical structure of a
the ester bond on the glycerol moiety.
1-monoacylglycerol
Monoacylglycerols can be formed by both industrial chemical and biological
processes. They are formed biochemically via release of a fatty acid from
diacylglycerol by diacylglycerol lipase. Monoacylglycerols are broken down
by monoacylglycerol lipase.
Mono- and diglycerides are commonly added to commercial food products in
small quantities. They act as emulsifiers, helping to mix ingredients such as
oil and water that would not otherwise blend well.[2]
The commercial source may be either animal (cow- or hog-derived) or
vegetable, and they may be synthetically made as well. They are often found General chemical structure of a
2-monoacylglycerol
in bakery products, beverages, ice cream, chewing gum, shortening, whipped
toppings, margarine, and confections. When used in bakery products,
monoglycerides improve loaf volume, and create a smooth, soft crumb.
One special monoacylglycerol, 2-arachidonoylglycerol, is a full agonist of the cannabinoid receptors. Another
important monoacylglycerol is 2-oleoylglycerol, which is a GPR119 agonist.[3]
Monoglyceride 15

References
[1] "Monoacylglycerols" (http:/ / www. cyberlipid. org/ glycer/ glyc0002. htm). Cyberlipid Center. .
[2] "Questions About Food Ingredients" (http:/ / www. vrg. org/ nutshell/ faqingredients. htm#mono). Vegetarian Resource Group. . Retrieved 13
November 2011.
[3] Hansen, K. B.; Rosenkilde, M. M.; Knop, F. K.; Wellner, N.; Diep, T. A.; Rehfeld, J. F.; Andersen, U. B.; Holst, J. J. et al (2011). "2-Oleoyl
Glycerol is a GPR119 Agonist and Signals GLP-1 Release in Humans". Journal of Clinical Endocrinology & Metabolism 96 (9):
E1409–E1417. doi:10.1210/jc.2011-0647. PMID 21778222.

Diglyceride
A diglyceride, or a diacylglycerol (DAG), is a glyceride consisting of
two fatty acid chains covalently bonded to a glycerol molecule through
ester linkages. One example, shown on the right, is
Chemical structure of the diglyceride
1-palmitoyl-2-oleoyl-glycerol, which contains side-chains derived 1-palmitoyl-2-oleoyl-glycerol
from palmitic acid and oleic acid. Diacylglycerols can also have many
different combinations of fatty acids attached at both the C-1 and C-2 positions.

Food additive
Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and
water, which would not otherwise blend well.
The commercial source may be either animal (cow- or hog-derived) or vegetable, derived primarily from partially
hydrogenated soy bean and canola oil. They may also be synthetically produced. They are often found in bakery
products, beverages, ice cream, peanut butter, chewing gum, shortening, whipped toppings, margarine, and
confections.

Biological functions

Protein kinase C activation

In biochemical signaling, diacylglycerol functions as a second
messenger signaling lipid, and is a product of the hydrolysis of the
phospholipid phosphatidylinositol 4,5-bisphosphate (PIP2) by the
enzyme phospholipase C (PLC) (a membrane-bound enzyme) that,
through the same reaction, produces inositol trisphosphate (IP3).
Although inositol trisphosphate diffuses into the cytosol,
diacylglycerol remains within the plasma membrane, due to its
hydrophobic properties. IP3 stimulates the release of calcium ions from
the smooth endoplasmic reticulum, whereas DAG is a physiological
activator of protein kinase C (PKC). The production of DAG in the
PIP2 cleavage to IP3 and DAG initiates
membrane facilitates translocation of PKC from the cytosol to the
intracellular calcium release and PKC activation.
plasma membrane.

Diacylglycerol can be mimicked by the tumor-promoting compounds phorbol esters.[1]

Diglyceride 16

Other
In addition to activating PKC, diacylglycerol has a number of other functions in the cell:
• a source for prostaglandins
• a precursor of the endocannabinoid 2-arachidonoylglycerol
• an activator of a subfamily of transient receptor potential canonical (TRPC) cation channels, TRPC3/6/7.

Metabolism
Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is
derived primarily from dihydroxyacetone phosphate, a product of
glycolysis (usually in the cytoplasm of liver or adipose tissue cells).
Glycerol-3-phosphate is first acylated with acyl-coenzyme A
(acyl-CoA) to form lysophosphatidic acid, which is then acylated with
another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic
glycerol-3-phosphate
acid is then de-phosphorylated to form diacylglycerol.

Diacylglycerol is a precursor to triacylglycerol (triglyceride), which is formed in the addition of a third fatty acid to
the diacylglycerol under the catalysis of diglyceride acyltransferase.
Since diacylglycerol is synthesized via phosphatidic acid, it will usually contain a saturated fatty acid at the C-1
position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. [2]

References
[1] Blumberg, PM (1988). "Protein kinase C as the receptor for the phorbol ester tumor promoters: Sixth Rhoads memorial award lecture".
Cancer Research 48 (1): 1–8. PMID 3275491.
[2] Berg J, Tymoczko JL, Stryer L (2006). Biochemistry (6th ed.). San Francisco: W. H. Freeman. ISBN 0-7167-8724-5.
Triglyceride 17

Triglyceride
A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an
ester derived from glycerol and three fatty acids.[1] There are many
triglycerides: depending on the oil source, some are highly unsaturated,
some less so.
Saturated compounds are "saturated" with hydrogen — all available
places where hydrogen atoms could be bonded to carbon atoms are Example of an unsaturated fat triglyceride. Left
occupied. Unsaturated compounds have double bonds (C=C) between part: glycerol, right part from top to bottom:
palmitic acid, (contains)oleic acid, alpha-linolenic
carbon atoms, reducing the number of places where hydrogen atoms
acid, chemical formula: C55H98O6
can bond to carbon atoms. Saturated compounds have single bonds
(C-C) between the carbon atoms, and the other bond is bound to
hydrogen atoms (for example =CH-CH=, -CH2-CH2-, etc.).

Unsaturated fats have a lower melting point and are more likely to be liquid. Saturated fats have a higher melting
point and are more likely to be solid.
Triglycerides are the main constituents of vegetable oil (typically more unsaturated) and animal fats (typically more
saturated).[2] In humans, triglycerides are a mechanism for storing unused calories, and their high concentration in
blood correlates with the consumption of starchy and other high carbohydrate foods.

Chemical structure
Triglycerides are formed by combining glycerol with three molecules of fatty acid. Alcohols have a hydroxyl (HO-)
group. Organic acids have a carboxyl (-COOH) group. Alcohols and organic acids join to form esters. The glycerol
molecule has three hydroxyl (HO-) groups. Each fatty acid has a carboxyl group (-COOH). In triglycerides, the
hydroxyl groups of the glycerol join the carboxyl groups of the fatty acid to form ester bonds:
HOCH2CH(OH)CH2OH + RCO2H + R'CO2H + R''CO2H → RCO2CH2CH(O2CR')CR'' + 3H2O
The three fatty acids (RCO2H, R'CO2H, R''CO2H in the above equation) are usually different, but many kinds of
triglycerides are known. The chain lengths of the fatty acids in naturally occurring triglycerides vary, but most
contain 16, 18, or 20 carbon atoms. Natural fatty acids found in plants and animals are typically composed of only
even numbers of carbon atoms, reflecting the pathway for their biosynthesis from the two-carbon building-block
acetyl CoA. Bacteria, however, possess the ability to synthesise odd- and branched-chain fatty acids. As a result,
ruminant animal fat contains odd-numbered fatty acids, such as 15, due to the action of bacteria in the rumen. Many
fatty acids are unsaturated, some are polyunsaturated, e.g., those derived from linoleic acid.
Most natural fats contain a complex mixture of individual triglycerides. Because of this, they melt over a broad range
of temperatures. Cocoa butter is unusual in that it is composed of only a few triglycerides, derived from palmitic,
oleic, and stearic acids.
Triglyceride 18

Metabolism
The enzyme pancreatic lipase acts at the ester bond, hydrolysing the bond and "releasing" the fatty acid. In
triglyceride form, lipids cannot be absorbed by the duodenum. Fatty acids, monoglycerides (one glycerol, one fatty
acid), and some diglycerides are absorbed by the duodenum, once the triglycerides have been broken down.
Triglycerides, as major components of very-low-density lipoprotein (VLDL) and chylomicrons, play an important
role in metabolism as energy sources and transporters of dietary fat. They contain more than twice as much energy (9
kcal/g or 38 kJ/g ) as carbohydrates and proteins. In the intestine, triglycerides are split into monoacylglycerol and
free fatty acids in a process called lipolysis, with the secretion of lipases and bile, which are subsequently moved to
absorptive enterocytes, cells lining the intestines. The triglycerides are rebuilt in the enterocytes from their fragments
and packaged together with cholesterol and proteins to form chylomicrons. These are excreted from the cells and
collected by the lymph system and transported to the large vessels near the heart before being mixed into the blood.
Various tissues can capture the chylomicrons, releasing the triglycerides to be used as a source of energy. Fat and
liver cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the
hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids.
As the brain cannot utilize fatty acids as an energy source (unless converted to a ketone), the glycerol component of
triglycerides can be converted into glucose, via glycolysis by conversion into Dihydroxyacetone phosphate and then
into Glyceraldehyde 3-phosphate, for brain fuel when it is broken down. Fat cells may also be broken down for that
reason, if the brain's needs ever outweigh the body's.
Triglycerides cannot pass through cell membranes freely. Special enzymes on the walls of blood vessels called
lipoprotein lipases must break down triglycerides into free fatty acids and glycerol. Fatty acids can then be taken up
by cells via the fatty acid transporter (FAT).

Role in disease
In the human body, high levels of triglycerides in the bloodstream have been linked to atherosclerosis and, by
extension, the risk of heart disease and stroke. However, the relative negative impact of raised levels of triglycerides
compared to that of LDL:HDL ratios is as yet unknown. The risk can be partly accounted for by a strong inverse
relationship between triglyceride level and HDL-cholesterol level.

Guidelines
The American Heart Association has set guidelines for triglyceride levels:[3]

Level mg/dL Level mmol/L Interpretation

<150 <1.70 Normal range, low risk

151-199 1.70-2.25 Slightly above normal

200-499 2.26-5.65

>500 >5.65 Very high: high risk

These levels are tested after fasting 8 to 12 hours. Triglyceride levels remain temporarily higher for a period of time
after eating.
Triglyceride 19

Reducing triglyceride levels

Diets high in carbohydrates, with carbohydrates accounting for more than 60% of the total energy intake, can
increase triglyceride levels.[3] Of note is how the correlation is stronger for those with higher BMI (28+) and insulin
resistance (more common among overweight and obese) is a primary suspect cause of this phenomenon of
carbohydrate-induced hypertriglyceridemia.[4]
There is evidence that carbohydrate consumption causing a high glycemic index can cause insulin overproduction
and increase triglyceride levels in women.[5]
Adverse changes associated with carbohydrate intake, including triglyceride levels, are stronger risk factors for heart
disease in women than in men.[6]
Triglyceride levels are also reduced by exercise and by consuming omega-3 fatty acids from fish, flax seed oil, and
other sources. See potential health benefits of Omega-3.
Carnitine has the ability to lower blood triglyceride levels.[7] In some cases, fibrates have been used to bring down
triglycerides substantially.[8]
Heavy use of alcohol can elevate triglycerides levels.[9]
Fish oil has been found to decrease triglycerides.[10]

Industrial uses
Linseed oil and related oils are important components of useful products used in oil paints and related coatings.
Linseed oil is rich in di- and triunsaturated fatty acid components, which tend to harden in the presence of oxygen.
The hardening process is peculiar to these so-called "drying oils". It is caused by a polymerization process that
begins with oxygen molecules attacking the carbon backbone.
Triglycerides are also split into their components via transesterification during the manufacture of biodiesel. The
resulting fatty acid esters can be used as fuel in diesel engines. The glycerin has many uses, such as in the
manufacture of food and in the production of pharmaceuticals.

Staining
Staining for fatty acids, triglycerides, lipoproteins, and other lipids is done through the use of lysochromes
(fat-soluble dyes). These dyes can allow the qualification of a certain fat of interest by staining the material a specific
color. Some examples: Sudan IV, Oil Red O, and Sudan Black B.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. [11]
[[File:
Triglyceride 20

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Triglyceride 21

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Triglyceride 22

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Statin Pathway edit [12]

References
[1] "Nomenclature of Lipids" (http:/ / www. chem. qmul. ac. uk/ iupac/ lipid/ ). IUPAC-IUB Commission on Biochemical Nomenclature (CBN).
. Retrieved 2007-03-08.
[2] Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
[3] "Your Triglyceride Level" (http:/ / www. americanheart. org/ presenter. jhtml?identifier=183#Triglyceride). What Your Cholesterol Levels
Mean. American Heart Association. . Retrieved 2009-05-22.
[4] Parks, E.J. (2002). "Dietary carbohydrate’s effects on lipogenesis and the relationship of lipogenesis to blood insulin and glucose
concentrations". British Journal of Nutrition 87: S247–S253. doi:10.1079/BJN/2002544. PMID 12088525. "Those with a body mass index
(BMI) equal to or greater than 28 kg/m2 experienced a 30% increase in TAG concentration, while those whose BMI was less than 28,
experienced no change...These data demonstrate that certain characteristics (e.g., BMI) can make some individuals more sensitive with respect
to lipid and lipoprotein changes when dietary CHO is increased. Such characteristics that have been identified from previous work in this field
and include BMI, insulin sensitivity (Coulston et al. 1989), concentration of TAG before the dietary change is made (Parks et al. 2001),
hormone replacement therapy (Kasim-Karakas et al. 2000), and genetic factors (Dreon et al. 2000)."
[5] "Focusing on Fiber?" (http:/ / www. drweil. com/ drw/ u/ id/ QAA298788). [Link]. . Retrieved 2010-08-02.
[6] "Dietary Glycemic Load and Index and Risk of Coronary Heart Disease in a Large Italian Cohort" (http:/ / archinte. ama-assn. org/ cgi/
content/ abstract/ 170/ 7/ 640). Archives of internal medicine. . Retrieved 2010-05-01.
[7] Balch, Phyllis A. Prescription for nutritional healing. 4th ed. New York: Avery, 2006. p. 54 Carnitine
[8] "Fibrates: Where Are We Now?: Fibrates and Triglycerides" (http:/ / www. medscape. com/ viewarticle/ 587134_7). [Link]. .
Retrieved 2010-08-02.
[9] Hemat, R A S (2003). Principles of Orthomolecularism (http:/ / books. google. com/ ?id=ED_xI-CEzFYC& pg=PA254& lpg=PA254&
dq=alcohol+ consumption+ can+ elevate+ triglyceride+ levels). Urotext. p. 254. ISBN 1-903737-06-0. .
[10] "Examine - Triglycerides" (http:/ / examine. com/ topics/ Triglycerides/ ). . Retrieved 2012-04-04.
Triglyceride 23

[11] The interactive pathway map can be edited at WikiPathways: "Statin_Pathway_WP430" (http:/ / www. wikipathways. org/ index. php/
Pathway:WP430). .
[12] http:/ / www. wikipathways. org/ index. php/ Pathway:WP430

Quaternary ammonium cation

Quaternary ammonium cations, also known as quats, are positively
charged polyatomic ions of the structure NR4+, R being an alkyl group
or an aryl group.[1] Unlike the ammonium ion (NH4+) and the primary,
secondary, or tertiary ammonium cations, the quaternary ammonium
cations are permanently charged, independent of the pH of their
solution. Quaternary ammonium salts or quaternary ammonium
compounds (called quaternary amines in oilfield parlance) are salts
of quaternary ammonium cations with an anion.

Synthesis
Quaternary ammonium compounds are prepared by alkylation of
tertiary amines, in a process called quaternization.[2] Typically one of Quaternary ammonium cation. The R groups may
the alkyl groups on the amine is larger than the others.[3] A typical be the same or different alkyl or aryl groups.
Also, the R groups may be connected.
synthesis is for benzalkonium chloride from a long-chain
alkyldimethylamine and benzyl chloride:
CH3(CH2)nN(CH3)2 + ClCH2C6H5 → CH3(CH2)nN(CH3)2CH2C6H5]+Cl-

Applications
Quaternary ammonium salts are used as disinfectants, surfactants, fabric softeners, and as antistatic agents (e.g. in
shampoos). In liquid fabric softeners, the chloride salts are often used. In dryer anticling strips, the sulfate salts are
often used. Spermicidal jellies also contain quaternary ammonium salts.

As antimicrobials
Quaternary ammonium compounds have also been shown to have antimicrobial activity. [4] Certain quaternary
ammonium compounds, especially those containing long alkyl chains, are used as antimicrobials and disinfectants.
Examples are benzalkonium chloride, benzethonium chloride, methylbenzethonium chloride, cetalkonium chloride,
cetylpyridinium chloride, cetrimonium, cetrimide, dofanium chloride, tetraethylammonium bromide,
didecyldimethylammonium chloride and domiphen bromide. Also good against fungi, amoeba, and enveloped
viruses,[5] quats act by disrupting the cell membrane. Quaternary ammonium compounds are lethal to a wide variety
of organisms except endospores, Mycobacterium tuberculosis and non-enveloped viruses.
In contrast to phenolics, quaternary ammonium compounds are not very effective in the presence of organic
compounds. Yet, they are very effective in combination with phenols. Quaternary ammonium compounds are
deactivated by soaps, other anionic detergents, and cotton fibers.[5] Also, they are not recommended for use in hard
water. Effective levels are at 200 ppm.[6] They are effective at temperatures up to 212 °F (unknown operator:
u'strong' °C).
Along with sodium hypochlorite, quaternary ammonium salts are the primary chemicals used in foodservice industry
as sanitizing agents.
Quaternary ammonium cation 24

As phase transfer catalysts

In organic synthesis, quaternary ammonium salts are employed as phase transfer catalysts (PTC). Such catalysts
accelerate reactions between reagents dissolved in immiscible solvents. The highly reactive reagent dichlorocarbene
is generated via PTC by reaction of chloroform and sodium hydroxide.

Osmolytes
Quaternary ammonium compounds are present in osmolytes, specifically glycine betaine, which stabilize osmotic
pressure in cells.[7]

Health effects
Quaternary ammonium compounds can display a range of health effects, amongst which are mild skin and
respiratory irritation [8] up to severe caustic burns on skin and gastro-intestinal lining (depending on concentration),
gastro-intestinal symptoms (e.g., nausea and vomiting), coma, convulsions, hypotension and death.[9]
They are thought to be the chemical group responsible for anaphylactic reactions that occur with use of
neuromuscular blocking drugs during general anaesthesia in surgery.[10] Quaternium-15 is the single most often
found cause of allergic contact dermatitis of the hands (16.5% in 959 cases)[11]

References
[1] Nic, M.; Jirat, J.; Kosata, B., eds. (2006–). "quaternary ammonium compounds" (http:/ / goldbook. iupac. org/ Q05003. html). IUPAC
Compendium of Chemical Terminology (Online ed.). doi:10.1351/goldbook.Q05003. ISBN 0-9678550-9-8. .
[2] Smith, Michael B.; March, Jerry (2001), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (5th ed.), New York:
Wiley-Interscience, ISBN 0-471-58589-0
[3] Kosswig, K. “Surfactants” in Ullmann’s Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a25_747.
[4] Zhishen Jia, Dongfeng shen, Weiliang Xu, Synthesis and antibacterial activities of quaternary ammonium salt of chitosan, Carbohydrate
Research, Volume 333, Issue 1, 22 June 2001, Pages 1-6, ISSN 0008-6215 (http:/ / dx. doi. org/ 10. 1016/ S0008-6215(01)00112-4)
[5] Specific Antimicrobials (http:/ / www. mansfield. ohio-state. edu/ ~sabedon/ biol2032. htm), outline of lecture by Stephen T. Abedon, Ohio
State U., URL accessed Dec 2008.
[6] The Use of Disinfectants In the Swine Industry (http:/ / mark. asci. ncsu. edu/ HealthyHogs/ book1993/ ladd1. htm), Mark G. Ladd, North
Carolina State Univ., URL accessed Dec 2008.
[7] http:/ / dx. doi. org/ 10. 1128/ AEM. 67. 6. 2692-2698. 2001 Sleator, Roy D., Wouters, Jeroen, Gahan, Cormac G. M., Abee, Tjakko, Hill,
Colin Analysis of the Role of OpuC, an Osmolyte Transport System, in Salt Tolerance and Virulence Potential of Listeria monocytogenes
Appl. Environ. Microbiol. 2001 67: 2692-2698
[8] http:/ / www. ehjournal. net/ content/ pdf/ 1476-069x-8-11. pdf
[9] http:/ / www. inchem. org/ documents/ pims/ chemical/ pimg022. htm#SectionTitle:2. 1%20%20Main%20risk%20and%20target%20organs
[10] Harper, N. J. et al (2009): "Suspected anaphylactic reactions associated with anaesthesia", Anaesthesia, 64(2):199-211
[11] E. Warshaw, et al. Contact dermatitis of the hands: Cross-sectional analyses of North American Contact Dermatitis Group Data, 1994-2004.
Journal of the American Academy of Dermatology, Volume 57, Issue 2, Pages 301-314

External links
• Toxicities of quaternary ammonium ([Link]
Oil 25

Oil
An oil is any substance that is liquid at ambient temperatures and does not mix with water but may mix with other
oils and organic solvents. This general definition includes vegetable oils, volatile essential oils, petrochemical oils,
and synthetic oils.

Etymology
First attested in English 1176, the word oil comes from Old French "oile", from Latin "oleum",[1] which in turn
comes from the Greek "ἔλαιον" (elaion), "olive oil, oil"[2] and that from "ἐλαία" (elaia), "olive tree".[3] The earliest
attested form of the word is the Mycenaean Greek e-ra-wo, written in Linear B syllabic script.[4]

Types

Organic oils
Organic oils are produced in remarkable diversity by plants, animals, and other organisms through natural metabolic
processes. Lipid is the scientific term for the fatty acids, steroids and similar chemicals often found in the oils
produced by living things, while oil refers to an overall mixture of chemicals. Organic oils may also contain
chemicals other than lipids, including proteins, waxes and alkaloids.
Lipids can be classified by the way that they are made by an organism, their chemical structure and their limited
solubility in water compared to oils. They have a high carbon and hydrogen content and are considerably lacking in
oxygen compared to other organic compounds and minerals; they tend to be relatively nonpolar molecules, but may
include both polar and nonpolar regions as in the case of phospholipids and steroids.[5]

Mineral oils
Crude oil, or petroleum, and its refined components, collectively termed petrochemicals, are crucial resources in the
modern economy. Crude oil originates from ancient fossilized organic materials, such as zooplankton and algae,
which geochemical processes convert into oil.[6] It is classified as a mineral oil because it does not have an organic
origin on human timescales, but is instead obtained from rocks, underground traps, or sands. Mineral oil also refers
to several specific distillates of crude oil.
Oil 26

Applications

Cosmetics
Oils are applied to hair to give it a lustrous look, to prevent tangles and roughness and to
stabilize the hair to promote growth. See Hair conditioner.

Religion
Oils are commonly used in ritual anointments. As a particular example, holy anointing oil has
been an important ritual liquid for Judaism and Christianity.

Painting
Color pigments are easily suspended in oil, making it suitable as a supporting medium for
paints. The oldest known extant oil paintings date from 650 AD.[7]

Heat transfer
Oils are used as coolants in oil cooling, for instance in electric transformers. Oils are also used A bottle of olive oil
used in food
to enhance heating in other applications, such as cooking (especially in frying).

Lubrication
Oils are commonly used as lubricants. Mineral oils are more commonly used as machine lubricants than biological
oils are.

Fuel
Some oils burn in liquid or aerosol form, generating heat which can be used directly or converted into other forms of
energy such as electricity or mechanical work. To obtain many fuel oils, crude oil is pumped from the ground and is
shipped via oil tanker to an oil refinery. There, it is converted from crude oil to diesel fuel (petrodiesel), ethane (and
other short-chain alkanes), fuel oils (heaviest of commercial fuels, used in ships/furnaces), gasoline (petrol), jet fuel,
kerosene, benzene (historically), and liquefied petroleum gas. A 42 gallon barrel (U.S.) of crude oil produces
approximately 10 gallons of diesel, 4 gallons of jet fuel, 19 gallons of gasoline, 7 gallons of other products, 3 gallons
split between heavy fuel oil and liquified petroleum gases,[8] and 2 gallons of heating oil. The total production of a
barrel of crude into various products results in an increase to 45 gallons.[8] Not all oils used as fuels are mineral oils,
see biodiesel and vegetable oil fuel.
Oil 27

Chemical feedstock
Crude oil can be refined into a wide variety of component hydrocarbons. Petrochemicals are the refined components
of crude oil and the chemical products made from them. They are used as detergents, fertilizers, medicines, paints,
plastics, synthetic fibers, and synthetic rubber. Organic oils are another important chemical feedstock, especially in
green chemistry.

References
[1] oleum (http:/ / www. perseus. tufts. edu/ hopper/ text?doc=Perseus:text:1999. 04. 0059:entry=oleum), Charlton T. Lewis, Charles Short, A
Latin Dictionary, on Perseus Digital Library
[2] ἔλαιον (http:/ / www. perseus. tufts. edu/ hopper/ text?doc=Perseus:text:1999. 04. 0057:entry=e)/ laion), Henry George Liddell, Robert Scott,
A Greek-English Lexicon, on Perseus Digital Library
[3] ἐλαία (http:/ / www. perseus. tufts. edu/ hopper/ text?doc=Perseus:text:1999. 04. 0057:entry=e)lai/ a), Henry George Liddell, Robert Scott, A
Greek-English Lexicon, on Perseus Digital Library
[4] Palaeolexicon (http:/ / www. palaeolexicon. com/ ), Word study tool of ancient languages
[5] Alberts, Bruce; Johnson, Alexander; Lewis, Julian; Raff, Martin; Roberts, Keith; Walter, Peter. Molecular Biology of the Cell. New York:
Garland Science, 2002, pp. 62, 118-119.
[6] Kvenvolden, Keith A. (2006). "Organic geochemistry – A retrospective of its first 70 years". Organic Geochemistry 37: 1.
doi:10.1016/[Link].2005.09.001.
[7] "Oldest Oil Paintings Found in Afghanistan" (http:/ / dsc. discovery. com/ news/ 2008/ 02/ 19/ oldest-oil-painting. html), Rosella Lorenzi,
Discovery News. Feb. 19, 2008.
[8] U.S. Energy Information Administration (EIA) (http:/ / www. eia. gov/ energyexplained/ index. cfm?page=oil_home) — Retrieved
2011-10-02.

External links
• Petroleum Online e-Learning resource from IHRDC ([Link]

Fat
Fats consist of a wide group of compounds that are generally soluble in organic solvents and generally insoluble in
water. Chemically, fats are triglycerides, triesters of glycerol and any of several fatty acids. Fats may be either solid
or liquid at room temperature, depending on their structure and composition. Although the words "oils", "fats", and
"lipids" are all used to refer to fats, "oils" is usually used to refer to fats that are liquids at normal room temperature,
while "fats" is usually used to refer to fats that are solids at normal room temperature. "Lipids" is used to refer to
both liquid and solid fats, along with other related substances, usually in a medical or biochemical context. The word
"oil" is also used for any substance that does not mix with water and has a greasy feel, such as petroleum (or crude
oil), heating oil, and essential oils, regardless of its chemical structure.[1]
Fats form a category of lipid, distinguished from other lipids by their chemical structure and physical properties. This
category of molecules is important for many forms of life, serving both structural and metabolic functions. They are
an important part of the diet of most heterotrophs (including humans). Fats or lipids are broken down in the body by
enzymes called lipases produced in the pancreas.
Examples of edible animal fats are lard, fish oil, butter/ghee and whale blubber. They are obtained from fats in the
milk and meat, as well as from under the skin, of an animal. Examples of edible plant fats include peanut, soya bean,
sunflower, sesame, coconut and olive oils, and cocoa butter. Vegetable shortening, used mainly for baking, and
margarine, used in baking and as a spread, can be derived from the above oils by hydrogenation.
These examples of fats can be categorized into saturated fats and unsaturated fats. Unsaturated fats can be further
divided into cis fats, which are the most common in nature, and trans fats, which are rare in nature but present in
partially hydrogenated vegetable oils.
Fat 28

Chemical structure
There are many different kinds of fats, but each is a
variation on the same chemical structure. All fats are
derivatives of fatty acids and glycerol. The molecules
are called triglycerides, which are triesters of glycerol
(an ester being the molecule formed from the reaction
of the carboxylic acid and an organic alcohol). As a
simple visual illustration, if the kinks and angles of
these chains were straightened out, the molecule would
have the shape of a capital letter E. The fatty acids
would each be a horizontal line; the glycerol
"backbone" would be the vertical line that joins the
horizontal lines. Fats therefore have "ester" bonds.

The properties of any specific fat molecule depend on A triglyceride molecule

the particular fatty acids that constitute it. Different
fatty acids are composed of different numbers of carbon and hydrogen atoms. The carbon atoms, each bonded to two
neighboring carbon atoms, form a zigzagging chain; the more carbon atoms there are in any fatty acid, the longer its
chain will be. Fatty acids with long chains are more susceptible to intermolecular forces of attraction (in this case,
van der Waals forces), raising its melting point. Long chains also yield more energy per molecule when metabolized.

Saturated and unsaturated fats

A fat's constituent fatty acids may also differ in the C/H ratio. When all three fatty acids have the formula
CnH(2n+1)CO2H, the resulting fat is called "saturated". Values of n usually range from 13 to 17. Each carbon atom in
the chain is saturated with hydrogen, meaning they are bonded to as many hydrogens as possible. Unsaturated fats
are derived from fatty acids with the formula CnH(2n-1)CO2H. These fatty acids contain double bonds within carbon
chain. This results in an "unsaturated" fatty acid. More specifically, it would be a monounsaturated fatty acid.
Polyunsaturated fatty acids would be fatty acids with more than one double bond; they have the formula,
CnH(2n-3)CO2H and CnH(2n-5)CO2H. Unsaturated fats can be converted to saturated ones by the process of
hydrogenation. This technology underpinned the development of margerine.
Saturated and unsaturated fats differ in their energy content and melting point. Since unsaturated fats contain fewer
carbon-hydrogen bonds than saturated fats with the same number of carbon atoms, unsaturated fats will yield slightly
less energy during metabolism than saturated fats with the same number of carbon atoms. Saturated fats can stack
themselves in a closely packed arrangement, so they can freeze easily and are typically solid at room temperature.
For example, animal fats tallow and lard are high in saturated fatty acid content and are solids. Olive and linseed oils
on the other hand are highly unsaturated and are oily.

Trans fats
There are two ways the double bond may be arranged: the isomer with both parts of the chain on the same side of the
double bond (the cis-isomer), or the isomer with the parts of the chain on opposite sides of the double bond (the
trans-isomer). Most trans-isomer fats (commonly called trans fats) are commercially produced. Trans fatty acids are
rare in nature. The cis-isomer introduces a kink into the molecule that prevents the fats from stacking efficiently as in
the case of fats with saturated chains. This decreases intermolecular forces between the fat molecules, making it
more difficult for unsaturated cis-fats to freeze; they are typically liquid at room temperature. Trans fats may still
stack like saturated fats, and are not as susceptible to metabolization as other fats. Trans fats may significantly
increase the risk of coronary heart disease.[2]
Fat 29

Importance for living organisms

Vitamins A, D, E, and K are fat-soluble, meaning they can only be digested, absorbed, and transported in
conjunction with fats. Fats are also sources of essential fatty acids, an important dietary requirement.
Fats play a vital role in maintaining healthy skin and hair, insulating body organs against shock, maintaining body
temperature, and promoting healthy cell function.
Fats also serve as energy stores for the body, containing about 37.8 kilojoules (9 calories) per gram of fat.[3] They are
broken down in the body to release glycerol and free fatty acids. The glycerol can be converted to glucose by the
liver and thus used as a source of energy.
Fat also serves as a useful buffer towards a host of diseases. When a particular substance, whether chemical or
biotic—reaches unsafe levels in the bloodstream, the body can effectively dilute—or at least maintain equilibrium
of—the offending substances by storing it in new fat tissue. This helps to protect vital organs, until such time as the
offending substances can be metabolized and/or removed from the body by such means as excretion, urination,
accidental or intentional bloodletting, sebum excretion, and hair growth.
While it is nearly impossible to remove fat completely from the diet, it would also be unhealthy to do so. Some fatty
acids are essential nutrients, meaning that they can't be produced in the body from other compounds and need to be
consumed in small amounts. All other fats required by the body are non-essential and can be produced in the body
from other compounds.

Adipose tissue
In animals, adipose, or fatty tissue is the body's means of storing
metabolic energy over extended periods of time. Depending on current
physiological conditions, adipocytes store fat derived from the diet and
liver metabolism or degrade stored fat to supply fatty acids and
glycerol to the circulation. These metabolic activities are regulated by
several hormones (i.e., insulin, glucagon and epinephrine). The
location of the tissue determines its metabolic profile: "visceral fat" is
located within the abdominal wall (i.e., beneath the wall of abdominal
muscle) whereas "subcutaneous fat" is located beneath the skin (and The obese mouse on the left has large stores of
adipose tissue. For comparison, a mouse with a
includes fat that is located in the abdominal area beneath the skin but
normal amount of adipose tissue is shown on the
above the abdominal muscle wall). Visceral fat was recently right.
discovered to be a significant producer of signaling chemicals (i.e.,
hormones), among which are several which are involved in inflammatory tissue responses. One of these is resistin
which has been linked to obesity, insulin resistance, and Type 2 diabetes. This latter result is currently controversial,
and there have been reputable studies supporting all sides on the issue.
Fat 30

References
[1] Maton, Anthea; Jean Hopkins, Charles William McLaughlin, Susan Johnson, Maryanna Quon Warner, David LaHart, Jill D. Wright (1993).
Human Biology and Health. Englewood Cliffs, New Jersey, USA: Prentice Hall. ISBN 0-13-981176-1. OCLC 32308337.
[2] Mozaffarian D, Katan MB, Ascherio A, Stampfer MJ, Willett WC (13 April 2006). "Trans Fatty Acids and Cardiovascular Disease". New
England Journal of Medicine 354 (15): 1601–1613. doi:10.1056/NEJMra054035. PMID 16611951.
[3] Stern, David P. (May 19, 2008). Newtonian mechanics – (15) Energy (http:/ / www-istp. gsfc. nasa. gov/ stargaze/ Senergy. htm). From
Stargazers to Starships. Retrieved April 11, 2011 from NASA's International Solar-Terrestrial Physics Goddard Space Flight Center website.

• Donatelle, Rebecca J. (2005). Health, the Basics (6th ed.). San Francisco: Pearson Education, Inc.
ISBN 0-13-120687-7. OCLC 51801859.

Further reading
• Hayes, K.C. (May 2005). Dietary fat and blood lipids ([Link]
Retrieved March 10, 2011.

Soap
In chemistry, soap is a salt of a fatty acid.[1]
Soaps are mainly used as surfactants for
washing, bathing, and cleaning, but they are
also used in textile spinning and are
important components of lubricants. Soaps
for cleansing are obtained by treating
vegetable or animal oils and fats with a
strongly alkaline solution. Fats and oils are
composed of triglycerides: three molecules
of fatty acids attached to a single molecule
of glycerol.[2] The alkaline solution, often
called lye, brings about a chemical reaction
known as saponification. In saponification,
the fats are first hydrolyzed into free fatty
acids, which then combine with the alkali to A collection of decorative soaps, often found in hotels
form crude soap. Glycerol, often called
glycerine, is liberated and is either left in or
washed out and recovered as a useful
by-product according to the process
employed.[2]

Soaps are key components of most

lubricating greases, which are usually Two equivalent images of the chemical structure of sodium stearate, a typical soap.

emulsions of calcium soap or lithium soaps

and mineral oil. These calcium- and lithium-based greases are widely used. Many other metallic soaps are also
useful, including those of aluminium, sodium, and mixtures of them. Such soaps are also used as thickeners to
increase the viscosity of oils. In ancient times, lubricating greases were made by the addition of lime to olive oil.[3]
Soap 31

Mechanism of cleansing soaps

When used for cleaning, soap serves as a surfactant in conjunction with water. The
cleaning action of this mixture is attributed to the action of micelles, tiny spheres
coated on the outside with polar hydrophilic (water-loving) groups, encasing a
lipophilic (fat-loving) pocket that can surround the grease particles, causing them
to disperse in water. The lipophilic portion is made up of the long hydrocarbon
chain from the fatty acid. In other words, whereas normally oil and water do not
mix, the addition of soap allows oils to disperse in water and be rinsed away.
Synthetic detergents operate by similar mechanisms to soap.

Effect of the alkali

Structure of a micelle, a cell-like
structure formed by the
The type of alkali metal used determines the kind of soap produced. Sodium soaps,
aggregation of soap subunits (such prepared from sodium hydroxide, are firm, whereas potassium soaps, derived from
as sodium stearate). The exterior potassium hydroxide, are softer or often liquid. Historically, potassium hydroxide
of the micelle is hydrophilic
was extracted from the ashes of bracken or other plants. Lithium soaps also tend to
(attracted to water) and the interior
is lipophilic (attracted to oils).
be hard—these are used exclusively in greases.

Effects of fats
Soaps are derivatives of fatty acids. Traditionally they have been made from triglycerides (oils and fats).[4]
Triglyceride is the chemical name for the triesters of fatty acids and glycerin. Tallow, i.e., rendered beef fat, is the
most available triglyceride from animals. Its saponified product is called sodium tallowate. Typical vegetable oils
used in soap making are palm oil, coconut oil, olive oil, and laurel oil. Each species offers quite different fatty acid
content and, hence, results in soaps of distinct feel. The seed oils give softer but milder soaps. Soap made from pure
olive oil is sometimes called Castile soap or Marseille soap and is reputed for being extra-mild. The term "Castile" is
also sometimes applied to soaps from a mixture of oils, but a high percentage of olive oil.

Fatty acid content of various fats used for soap-making

Lauric acid Myristic acid Palmitic acid Stearic acid Oleic acid Linoleic acid Linolenic acid

fats C12, C14 C16 C18 C18 C18 C18

saturated saturated saturated saturated monounsaturated diunsaturated triunsaturated

Tallow 0 4 28 23 35 2 1

Coconut oil 48 18 9 3 7 2 0

Palm kernel 46 16 8 3 12 2 0
oil

Laurel oil 54 0 0 0 15 17 0

Olive oil 0 0 11 2 78 10 0

Canola 0 1 3 2 58 9 23

|+
Soap 32

History of cleansing soaps

Early history
The earliest recorded evidence of the production of soap-like materials
dates back to around 2800 BC in Ancient Babylon.[5] In the reign of
Nabonidus (556–539 BCE) a recipe for soap consisted of uhulu
[ashes], cypress [oil] and sesame [seed oil] "for washing the stones for
the servant girls".[6] A formula for soap consisting of water, alkali, and
cassia oil was written on a Babylonian clay tablet around 2200 BC.

The Ebers papyrus (Egypt, 1550 BC) indicates that ancient Egyptians
bathed regularly and combined animal and vegetable oils with alkaline
salts to create a soap-like substance. Egyptian documents mention that
Box for Amigo de Obrero (Worker's friend) soap
a soap-like substance was used in the preparation of wool for weaving. from 20th century. Part of the Museo del Objeto
del Objeto collection
Roman history
The word sapo, Latin for soap, first appears in Pliny the Elder's Historia Naturalis, which discusses the manufacture
of soap from tallow and ashes, but the only use he mentions for it is as a pomade for hair; he mentions rather
disapprovingly that the men of the Gauls and Germans were more likely to use it than their female counterparts.[7]
Aretaeus of Cappadocia, writing in the first century AD, observes among "Celts, which are men called Gauls, those
alkaline substances that are made into balls, called soap".[8]
A popular belief encountered in some places claims that soap takes its name from a supposed Mount Sapo, where
animal sacrifices were supposed to take place—tallow from these sacrifices would then have mixed with ashes from
fires associated with these sacrifices and with water to produce soap. But there is no evidence of a Mount Sapo
within the Roman world and no evidence for the apocryphal story. The Latin word sapo simply means "soap"; it was
likely borrowed from an early Germanic language and is cognate with Latin sebum, "tallow", which appears in Pliny
the Elder's account.[9] Roman animal sacrifices usually burned only the bones and inedible entrails of the sacrificed
animals; edible meat and fat from the sacrifices were taken by the humans rather than the gods.
Zosimos of Panopolis, ca. 300 AD, describes soap and soapmaking.[10] Galen describes soap-making using lye and
prescribes washing to carry away impurities from the body and clothes. According to Galen, the best soaps were
German, and soaps from Gaul were second best. This is a reference to true soap in antiquity.[10]

Islamic history
Solid soap was virtually unknown in northern Europe until the thirteenth century when it started being imported from
Islamic Spain and North Africa. By that time the manufacture of soap in the Islamic world had become virtually
industrialized, with sources in Fes, Damascus, and Aleppo. A 12th century Islamic document has the world's first
extant description of the process of soap production.[11] Mentioning the key ingredient, alkali, which later becomes
crucial to modern chemistry, derived from al-qaly or "ashes".

Medieval history
Soap-makers in Naples were members of a guild in the late sixth century,[12] and in the 8th century, soap-making
was well known in Italy and Spain.[13] The Carolingian capitulary De Villis, dating to around 800, representing the
royal will of Charlemagne, mentions soap as being one of the products the stewards of royal estates are to tally.
Soap-making is mentioned both as "women's work" and as the produce of "good workmen" alongside other
necessities such as the produce of carpenters, blacksmiths, and bakers.[14]
Soap 33

15th–20th centuries
In France, by the second half of the 15th century, the
semi-industrialized professional manufacture of soap was concentrated
in a few centers of Provence— Toulon, Hyères, and Marseille —
which supplied the rest of France.[15] In Marseilles, by 1525,
production was concentrated in at least two factories, and soap
production at Marseille tended to eclipse the other Provençal
centers.[16] English manufacture tended to concentrate in London.[17]

Finer soaps were later produced in Europe from the 16th century, using
vegetable oils (such as olive oil) as opposed to animal fats. Many of
these soaps are still produced, both industrially and by small-scale
artisans. Castile soap is a popular example of the vegetable-only soaps
derived by the oldest "white soap" of Italy.
In modern times, the use of soap has become universal in industrialized
nations due to a better understanding of the role of hygiene in reducing
the population size of pathogenic microorganisms. Industrially
manufactured bar soaps first became available in the late eighteenth
century, as advertising campaigns in Europe and the United States Ad for Pear' Soap, 1889
promoted popular awareness of the relationship between cleanliness
and health.[18]

Until the Industrial Revolution, soapmaking was conducted on a small

scale and the product was rough. Andrew Pears started making a
high-quality, transparent soap in 1789 in London. His son-in-law,
Thomas J. Barratt, opened a factory in Isleworth in 1862. William
Gossage produced low-price good-quality soap from the 1850s. Robert
Spear Hudson began manufacturing a soap powder in 1837, initially by
grinding the soap with a mortar and pestle. American manufacturer
Benjamin T. Babbitt introduced marketing innovations that included
sale of bar soap and distribution of product samples. William Hesketh
Lever and his brother, James, bought a small soap works in Warrington
in 1886 and founded what is still one of the largest soap businesses,
formerly called Lever Brothers and now called Unilever. These soap
businesses were among the first to employ large-scale advertising
campaigns.
1922 magazine advertisement for Palmolive
Soap.
Soap making processes
The industrial production of soap involves continuous processes, involving continuous addition of fat and removal of
product. Smaller-scale production involve the traditional batch processes. There are three variations: the
cold-process, wherein the reaction takes place substantially at room temperature, the semi-boiled or hot-process,
wherein the reaction takes place at near-boiling point, and the fully boiled process, wherein the reactants are boiled at
least once and the
Soap 34

glycerol recovered. The cold-process and hot-process (semi-boiled) are

the simplest and typically used by small artisans and hobbyists
producing handmade decorative soaps and similar. The glycerine
remains in the soap and the reaction continues for many days after the
soap is poured into moulds. The glycerine is left during the hot-process
method, but at the high temperature employed the reaction is
practically completed in the kettle, before the soap is poured into
moulds. This process is simple and quick and is the one employed in
small factories all over the world.
Liquid soap
Handmade soap from the cold process also differs from industrially
made soap in that an excess of fat is used, beyond that which is used to
consume the alkali (in a cold-pour process this excess fat called
"superfatting"), and the glycerine left in acts as a moisturizing agent.
However, the glycerine also makes the soap softer and less resistant to
becoming "mushy" if left wet. Since it is better to add too much oil and
have left-over fat, than to add too much lye and have left-over lye, soap
produced from the hot process also contains left-over glycerine and its
concommitant pros and cons. Further addition of glycerine and
processing of this soap produces glycerin soap. Superfatted soap is
more skin-friendly than one without extra fat. However, if too much fat
is added, it can leave a "greasy" feel to their skin. Sometimes an Manufacturing process of soaps/detergents
emollient additive such as jojoba oil or shea butter is added "at trace"
(i.e., the point at which the saponification process is sufficiently advanced that the soap has begun to thicken in the
cold process method) in the belief that nearly all the lye will be spent and it will escape saponification and remain
intact. In the case of hot-process soap, an emollient may be added after the initial oils have saponified so that they
remain unreacted in the finished soap. Superfatting can also be accomplished through a process known as "lye
discount" in which the soap maker uses less alkali than required instead of adding extra fats.

Cold process
Even in the cold-soapmaking process, some heat is usually required; the temperature is usually raised to a point
sufficient to ensure complete melting of the fat being used. The batch may also be kept warm for some time after
mixing to ensure that the alkali (hydroxide) is completely used up. This soap is safe to use after approximately
12–48 hours but is not at its peak quality for use for several weeks.
Cold-process soapmaking requires exact measurements of lye and fat amounts and computing their ratio, using
saponification charts to ensure that the finished product does not contain any excess hydroxide or too much free
unreacted fat. Saponification charts should also be used in hot-processes, but are not necessary for the "fully boiled
hot-process" soaping.
A cold-process soapmaker first looks up the saponification value of the fats being used on a saponification chart.
This value is used to calculate the appropriate amount of lye. Excess unreacted lye in the soap will result in a very
high pH and can burn or irritate skin; not enough lye and the soap is greasy. Most soap makers formulate their
recipes with a 4–10% deficit of lye so that all of the lye is converted and that excess fat is left for skin conditioning
benefits.
The lye is dissolved in water. Then oils are heated, or melted if they are solid at room temperature. Once the oils are
liquified and the lye is fully dissolved in water, they are combined. This lye-fat mixture is mixed until the two phases
(oils and water) are fully emulsified. Emulsification is most easily identified visually when the soap exhibits some
Soap 35

level of "trace", which is the thickening of the mixture. (Modern-day amateur soapmakers often use a stick blender to
speed this process). There are varying levels of trace. Depending on how additives will affect trace, they may be
added at light trace, medium trace, or heavy trace. After much stirring, the mixture turns to the consistency of a thin
pudding. "Trace" corresponds roughly to viscosity. Essential oils and fragrance oils can be added with the initial
soaping oils, but solid additives such as botanicals, herbs, oatmeal, or other additives are most commonly added at
light trace, just as the mixture starts to thicken.
The batch is then poured into moulds, kept warm with towels or
blankets, and left to continue saponification for 12 to 48 hours. (Milk
soaps or other soaps with sugars added are the exception. They
typically do not require insulation, as the presence of sugar increases
the speed of the reaction and thus the production of heat.) During this
time, it is normal for the soap to go through a "gel phase," wherein the
opaque soap will turn somewhat transparent for several hours, before
once again turning opaque.
After the insulation period, the soap is firm enough to be removed from
Handmade soaps sold at a shop in Hyères, France
the mould and cut into bars. At this time, it is safe to use the soap,
since saponification is in essence complete. However, cold-process
soaps are typically cured and hardened on a drying rack for 2–6 weeks
before use. During this cure period, trace amounts of residual lye is
consumed by saponification and excess water evaporates.

During the curing process, some molecules in the outer layer of the
solid soap react with the carbon dioxide of the air and produce a dusty
sheet of sodium carbonate. This reaction is more intense if the mass is
exposed to wind or low temperatures.

Hot processes

Hot-processed soaps are created by encouraging the saponification

reaction by adding heat to the reaction. This speeds the reaction.
Unlike cold-processed soap, in hot-process soaping the oils are
completely saponified by the end of the handling period, whereas with
cold pour soap the bulk of the saponification happens after the oils and Traditional Marseille soap

lye solution emulsification is poured into moulds.

In the hot-process, the hydroxide and the fat are heated and mixed together 80–100 °C, a little below boiling point,
until saponification is complete, which, before modern scientific equipment, the soapmaker determined by taste (the
sharp, distinctive taste of the hydroxide disappears after it is saponified) or by eye; the experienced eye can tell when
gel stage and full saponification has occurred. Beginners can find this information through research and classes.
Tasting soap for readiness is not recommended, as sodium and potassium hydroxides, when not saponified, are
highly caustic.

An advantage of the fully boiled hot process in soap making is that the exact amount of hydroxide required need not
be known with great accuracy. They originated when the purity of the alkali hydroxides were unreliable, as these
processes can use even naturally found alkalis such as wood ashes and potash deposits. In the fully boiled process,
the mix is actually boiled (100C+), and, after saponification has occurred, the "neat soap" is precipitated from the
solution by adding common salt, and the excess liquid drained off. This excess liquid carries away with it much of
the impurities and color compounds in the fat, to leave a purer, whiter soap, and with practically all the glycerine
removed. The hot, soft soap is then pumped into a mould. The spent hydroxide solution is processed for recovery of
glycerine.
Soap 36

Molds
Many commercially available soap moulds are made of silicone or various types of plastic, although many soap
making hobbyists may use cardboard boxes lined with a plastic film. Soaps can be made in long bars that are cut into
individual portions, or cast into individual moulds.

Purification and finishing

In the fully boiled process on factory scale, the soap is further purified
to remove any excess sodium hydroxide, glycerol, and other
impurities, colour compounds, etc. These components are removed by
boiling the crude soap curds in water and then precipitating the soap
with salt.
At this stage, the soap still contains too much water, which has to be
removed. This was traditionally done on chill rolls, which produced the
soap flakes commonly used in the 1940s and 1950s. This process was
A generic bar of soap, after purification and
superseded by spray dryers and then by vacuum dryers. finishing.
The dry soap (approximately 6–12% moisture) is then compacted into
small pellets or noodles. These pellets/noodles are now ready for soap finishing, the process of converting raw soap
pellets into a saleable product, usually bars.
Soap pellets are combined with fragrances and other materials and blended to homogeneity in an amalgamator
(mixer). The mass is then discharged from the mixer into a refiner, which, by means of an auger, forces the soap
through a fine wire screen. From the refiner, the soap passes over a roller mill (French milling or hard milling) in a
manner similar to calendering paper or plastic or to making chocolate liquor. The soap is then passed through one or
more additional refiners to further plasticize the soap mass. Immediately before extrusion, the mass is passed through
a vacuum chamber to remove any trapped air. It is then extruded into a long log or blank, cut to convenient lengths,
passed through a metal detector, and then stamped into shape in refrigerated tools. The pressed bars are packaged in
many ways.
Sand or pumice may be added to produce a scouring soap. The
scouring agents serve to remove dead skin cells from the surface being
cleaned. This process is called exfoliation. Many newer materials that
are effective but do not have the sharp edges and poor particle size
distribution of pumice are used for exfoliating soaps.
Nanoscopic metals are commonly added to certain soaps specifically
for both colouration and anti-bacterial properties. Titanium powder is
commonly used in extreme "white" soaps for these purposes; nickel,
aluminium, and silver are less commonly used. These metals exhibit an (Azul e branco soap) – A bar of blue-white soap
electron-robbing behaviour when in contact with bacteria, stripping
electrons from the organism's surface, thereby disrupting their functioning and killing them. Because some of the
metal is left behind on the skin and in the pores, the benefit can also extend beyond the actual time of washing,
helping reduce bacterial contamination and reducing potential odours from bacteria on the skin surface.
Soap 37

References
[1] IUPAC. " IUPAC Gold Book – soap (http:/ / goldbook. iupac. org/ S05721. html)" Compendium of Chemical Terminology, 2nd ed. (the
"Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected
version: created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook. Accessed
2010-08-09
[2] Cavitch, Susan Miller. The Natural Soap Book. Storey Publishing, 1994 ISBN 0-88266-888-9.
[3] Thorsten Bartels et al. "Lubricants and Lubrication" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Weinheim.
doi:10.1002/14356007.a15_423
[4] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia
of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
[5] Willcox, Michael (2000). "Soap" (http:/ / books. google. com/ books?id=4HI8dGHgeIQC& pg=PA453). In Hilda Butler. Poucher's Perfumes,
Cosmetics and Soaps (10th ed.). Dordrecht: Kluwer Academic Publishers. p. 453. ISBN 0-7514-0479-9. . "The earliest recorded evidence of
the production of soap-like materials dates back to around 2800 BCE in ancient Babylon."
[6] Noted in Martin Levey (1958). "Gypsum, salt and soda in ancient Mesopotamian chemical technology". Isis 49 (3): 336–342 (341).
doi:10.1086/348678. JSTOR 226942.
[7] Pliny the Elder, Natural History, XXVIII.191 (http:/ / penelope. uchicago. edu/ Thayer/ L/ Roman/ Texts/ Pliny_the_Elder/ 28*. html#191).
[8] Aretaeus, The Extant Works of Aretaeus, the Cappadocian, ed. and tr. Francis Adams (London) 1856:494 note 6, noted in Michael W. Dols,
"Leprosy in medieval Arabic medicine" Journal of the History of Medicine 1979:316 note 9; the Gauls with whom the Cappadocian would
have been familiar are those of Anatolian Galatia.
[9] soap (http:/ / www. etymonline. com/ index. php?term=soap). [Link]. Retrieved on 2011-11-20.
[10] Partington, James Riddick; Bert S Hall (1999). A History of Greek Fire and Gun Powder. JHU Press. p. 307. ISBN 0-8018-5954-9.
[11] BBC Science and Islam Part 2, Jim Al-Khalili. BBC Productions. Accessed 30 January 2012.
[12] footnote 48, p. 104, Understanding the Middle Ages: the transformation of ideas and attitudes in the Medieval world, Harald Kleinschmidt,
illustrated, revised, reprint edition, Boydell & Brewer, 2000, ISBN 0-85115-770-X.
[13] Anionic and Related Lime Soap Dispersants, Raymond G. Bistline, Jr., in Anionic surfactants: organic chemistry, Helmut Stache, ed.,
Volume 56 of Surfactant science series, CRC Press, 1996, chapter 11, p. 632, ISBN 0-8247-9394-3.
[14] Robinson, James Harvey (1904). Readings in European History: Vol. I (http:/ / www. fordham. edu/ halsall/ source/ carol-devillis. html).
Ginn and co. .
[15] John U. Nef (1936). "A Comparison of Industrial Growth in France and England from 1540 to 1640: III". The Journal of Political Economy
44 (5): 643–666 (660ff.). doi:10.1086/254976. JSTOR 1824135.
[16] L. Barthélemy, "La savonnerie marseillaise", 1883, noted by Nef 1936:660 note 99.
[17] Nef 1936:653, 660.
[18] McNeil, Ian (1990). An Encyclopaedia of the history of technology (http:/ / books. google. com/ books?id=uxsOAAAAQAAJ& pg=PA203).
Taylor & Francis. pp. 2003–205. ISBN 978-0-415-01306-2. .

Further reading
• Garzena, Patrizia-Tadiello, Marina (2004). Soap Naturally—Ingredients, methods and recipes for natural
handmade soap. Online information and Table of Contents ([Link] ISBN
978-0-9756764-0-0
• Thomssen, E. G., Ph. D. (1922). Soap-Making Manual ([Link] Free ebook
at Project Gutenberg
• Mohr, Merilyn (1979). "The Art of Soap Making". A Harrowsmith Contemporary Primer. Firefly Books. ISBN
978-0-920656-03-7
• Dunn, Kevin M. (2010) " Scientific Soapmaking: The Chemistry of Cold Process" Clavicula Press. ISBN
978-1-935652-09-0
Soap 38

External links
• Handmade soapmaking information, resources and mailing list ([Link]
• Soap History ([Link] American
Cleaning Institute (formerly The Soap and Detergent Association)
• A short history of soap ([Link] The Pharmaceutical
Journal
• Medieval Sourcebook: The Capitulary De Villis ([Link]
• How to Make Soap ([Link]
• Soap ([Link]

Cosmetics
Cosmetics are substances used to enhance the appearance or odor of
the human body. Cosmetics include skin-care creams, lotions,
powders, perfumes, lipsticks, fingernail and toe nail polish, eye and
facial makeup, towelettes, permanent waves, colored contact lenses,
hair colors, hair sprays and gels, deodorants, hand sanitizer, baby
products, bath oils, bubble baths, bath salts, butters and many other
types of products. A subset of cosmetics is called "make-up," which
refers primarily to colored products intended to alter the user’s
appearance. Many manufacturers distinguish between decorative
Assorted cosmetics and tools
cosmetics and care cosmetics. The word cosmetics derives from the
Greek κοσμητική τέχνη (kosmetikē tekhnē), meaning "technique of
dress and ornament", from κοσμητικός (kosmētikos), "skilled in
ordering or arranging"[1] and that from κόσμος (kosmos), meaning
amongst others "order" and "ornament".[2]

The manufacture of cosmetics is currently dominated by a small

number of multinational corporations that originated in the early 20th
century, but the distribution and sale of cosmetics is spread among a
wide range of different businesses. The U.S. Food and Drug
Administration (FDA) which regulates cosmetics in the United
States[3] defines cosmetics as: "intended to be applied to the human Woman applying makeup
body for cleansing, beautifying, promoting attractiveness, or altering
the appearance without affecting the body's structure or functions." This broad definition includes, as well, any
material intended for use as a component of a cosmetic product. The FDA specifically excludes soap from this
category.[4]
Cosmetics 39

History
The first archaeological evidence of cosmetics usage was found in
Egypt around 3500 BC during the Old Kingdom. The Ancient Greeks
and Romans also used cosmetics.[5][6] The Romans and Ancient
Egyptians used cosmetics containing poisonous mercury and often
lead. The ancient kingdom of Israel was influenced by cosmetics as
recorded in the Old Testament—2 Kings 9:30 where Jezebel painted
her eyelids—approximately 840 BC. The Biblical book of Esther
describes various beauty treatments as well.

In the Middle Ages, although its use was frowned upon by Church
leaders, many women still wore cosmetics. A popular fad for women
during the Middle Ages was to have a pale-skinned complexion, which
was achieved through either applying pastes of lead, chalk, or flour, or
by bloodletting. Women would also put white lead pigment that was Nefertiti bust with eye liner applied
known as "ceruse" on their faces to appear to have pale skin.[7]

Cosmetic use was frowned upon at many points in Western history.

For example, in the 19th century, Queen Victoria publicly declared
makeup improper, vulgar, and acceptable only for use by actors.[8]
Women in the 19th century liked to be thought of as fragile ladies.
They compared themselves to delicate flowers and emphasized their
delicacy and femininity. They aimed always to look pale and
interesting. Sometimes ladies discreetly used a little rouge on the
cheeks, and used "belladonna" to dilate their eyes to make their eyes
stand out more. Make-up was frowned upon in general especially
during the 1870s when social etiquette became more rigid.
An 1889 Henri de Toulouse-Lautrec painting of a
Actresses however were allowed to use make up and famous beauties woman applying cosmetics to her face

such as Sarah Bernhardt and Lillie Langtry could be powdered. Most

cosmetic products available were still either chemically dubious, or found in the kitchen amid food colorings, berries
and beetroot.
By the middle of the 20th century, cosmetics were in widespread use by women in nearly all industrial societies
around the world.
Cosmetics have been in use for thousands of years. The absence of regulation of the manufacture and use of
cosmetics has led to negative side effects, deformities, blindness, and even death through the ages. Examples of this
were the prevalent use of ceruse (white lead), to cover the face during the Renaissance, and blindness caused by the
mascara Lash Lure during the early 20th century.
The worldwide annual expenditures for cosmetics today is estimated at $19 billion.[9] Of the major firms, the largest
is L'Oréal, which was founded by Eugene Schueller in 1909 as the French Harmless Hair Colouring Company (now
owned by Liliane Bettencourt 26% and Nestlé 28%; the remaining 46% is traded publicly). The market was
developed in the USA during the 1910s by Elizabeth Arden, Helena Rubinstein, and Max Factor. These firms were
joined by Revlon just before World War II and Estée Lauder just after.
Beauty products are now widely available from dedicated internet-only retailers,[10] who have more recently been
joined online by established outlets, including the major department stores and traditional bricks and mortar beauty
retailers.
Cosmetics 40

Like most industries, cosmetic companies resist regulation by government agencies like the FDA, and have lobbied
against this throughout the years. The FDA does not have to approve or review the cosmetics, or what goes in them
before they are sold to the consumers. The FDA only regulates against the colors that can be used in the cosmetics
and hair dyes. The cosmetic companies do not have to report any injuries from the products; they also only have
voluntary recalls on products.[11]
Though modern make-up has been used mainly by women traditionally, gradually an increasing number of males are
using cosmetics usually associated to women to enhance or cover their own facial features. Concealer is commonly
used by cosmetic-conscious men. Cosmetics brands are releasing cosmetic products especially tailored for men, and
men are using such products increasily more commonly.[12]

Criticism and controversy

Further information: Campaign for Safe Cosmetics and Testing cosmetics on animals

Ethics
During the 20th century, the popularity of cosmetics increased rapidly. Cosmetics are increasingly used by girls at a
young age, especially in the United States. Due to the fast-decreasing age of make-up users, many companies, from
high-street brands like Rimmel to higher-end products like Estee Lauder, have catered to this expanding market by
introducing more flavored lipsticks and glosses, cosmetics packaged in glittery, sparkly packaging and marketing
and advertising using young models. The social consequences of younger and younger beautification has had much
attention in the media over the last few years.
Criticism of cosmetics has come from a variety of sources including some feminists, religious groups, animal rights
activists, authors and public interest groups. There is a growing awareness and preference for cosmetics that are
without any supposedly toxic ingredients, especially those derived from petroleum, sodium lauryl sulfate (SLS), and
parabens.[13]

Safety
Numerous published reports have raised concern over the safety of a few surfactants. SLS causes a number of skin
issues including dermatitis.[14][15][16][17][18]
Parabens can cause skin irritation and contact dermatitis in individuals with paraben allergies, a small percentage of
the general population.[19] Animal experiments have shown that parabens have a weak estrogenic activity, acting as
xenoestrogens.[20]
Prolonged use of makeup has also been linked to thinning eyelashes.[21]
Synthetic fragrances are widely used in consumer products. Studies concluded from patch testing show synthetic
fragrances are made of many ingredients which cause allergic reactions.[22]
Cosmetics companies have been criticized for making pseudo-scientific claims about their products which are
misleading or unsupported by scientific evidence.[23][24]

Animal testing
Cosmetics testing on animals is particularly controversial. Such tests, which are still conducted in the U.S., involve
general toxicity, eye and skin irritancy, phototoxicity (toxicity triggered by ultraviolet light) and mutagenicity.[25]
Cosmetics testing is banned in the Netherlands, Belgium, and the UK, and in 2002, after 13 years of discussion, the
European Union (EU) agreed to phase in a near-total ban on the sale of animal-tested cosmetics throughout the EU
from 2009, and to ban all cosmetics-related animal testing. France, which is home to the world's largest cosmetics
company, L'Oreal, has protested the proposed ban by lodging a case at the European Court of Justice in
Luxembourg, asking that the ban be quashed.[26] The ban is also opposed by the European Federation for Cosmetics
Cosmetics 41

Ingredients, which represents 70 companies in Switzerland, Belgium, France, Germany and Italy.[26]

Psychological Motivations for Cosmetics Use

A correlational study that surveyed thirty English women revealed that anxiety (p= .008), self-presentation (p=.003),
and conformity (p= .007) are significantly positively correlated with the application of cosmetics, and social
confidence (p=.032), emotional stability (p=.037), self-esteem (p=.003), and physical attractiveness (p=.006) are
significantly negatively correlated with cosmetics usage. (Fieldman, Robertson and Hussey, 2008)[27] This data
suggests that anxious, insecure females are motivated to apply cosmetics more so than females who are emotionally
secure, socially confident and perceive themselves as physically attractive.
Another study conducted by Cash, Dawson, Davis, Bowen and Galumbeck, utilizing a sample of undergraduate
college students, discovered that male peers tend to be harsher judges of a female's physical attractiveness than
female peers are. It also revealed that females may overestimate their physical attractiveness when they are wearing
makeup cosmetics. (1988)[28]
However, the current literature on the motivation for cosmetics use is scarce, and society would benefit from the
creation and repetition of empirical studies on this topic. The aforementioned studies only studied small samples of
females, predominantly consisting of participants of Caucasian descent, in their early twenties and all had some
college education. More studies should be conducted including samples taken from people of various races, cultures,
religious affiliations, education statuses, social classes, genders and ages.
Cultural Studies
There are many studies conducted that include the use of skin bleaching agents to lighten skin color. In Tanzania [29]
and Burkina Faso,[30] studies found that skin bleaching and "depigmenting" products are used among women.
Women in Africa, as reported by Lewis, et. al, perform practices such as using creams, gels, and common household
products to bleach their skin that is very harmful to the body. There are "six thematic motivations behind the practice
of skin bleaching: (a) to remove pimples, rashes, and skin disease; (b) to have soft skin; (c) to be White, ‘‘beautiful,’’
and more European looking; (d) to remove the adverse effects of extended skin bleaching use on the body; (e) to
satisfy one’s partner and/or attract male mates; and (f) to satisfy and impress peers. These findings provide empirical
support for skin bleaching being linked to self-objectification, colonialism, and Westernization." Researchers find
that there is significant evidence that there are cultural factors to why this practice occurs, especially among African
women (Lewis, 2011). The roots to why this exists are that there are "racial hierarchies" among Africans passed on
by the colonialism era whereby the dark-skinned Africans were inferior to the light skinned Europeans. This left
native Africans as vulnerable to the idea that skin color was significant and important within society. In Lewis, et al.
study of Tanzanian women, the principle that women internalize the perspectives of others as a primary reference for
viewing themselves is a framework for their participant study.
In the study done by Traore, et al., "A desire to change the color of the skin motivated 197 CDP users (43.9%), and a
desire to change the texture of the skin motivated 77 (17.2%); 51 users (11.4%) did not give a reason for their CDP
use, and 75 gave imitation of others as their motivation (16.8%). Treatment of skin imperfections motivated 48 users
(10.7%)." Women two cities in Burkina Faso use bleaching products to mainly maintain acne and other
dermatological ailments perceived by the users. Among the users, it was more common for women 40 years and
younger, unmarried, or divorced to use bleaching products. The main motivation for use of such products was also to
lighten skin for self-fulfilling reasons (Traore, 2011).
Cosmetics 42

Makeup types
Most cosmetics are distinguished by the area of the body intended for application.
• Face Primer, Come in various formulas to suite individual skin concerns. Most are meant to reduce the
appearance of pore size, prolong the wear of makeup, and allow for a smoother application of makeup. Applied
before foundation.
• Eye Primer, Used to prolong the wear of eyeshadows on the eye as well as intensify color payoff from shadows.
• Lipgloss, is a sheer form of lipstick that is in a liquid form.
• Lipstick, lip gloss, lip liner, lip plumper, lip balm, lip conditioner, lip primer, and lip boosters.[3] Lip stains have a
water or gel base and may contain alcohol to help the product stay on the lips. The idea behind lip stains is to
temporarily saturate the lips with a dye, rather than covering them with a colored wax. Usually designed to be
waterproof, the product may come with an applicator brush or be applied with a finger.
• Concealer, makeup used to cover any imperfections of the skin. Concealer is often used for any extra coverage
needed to cover blemishes, or any other marks. Concealer is often thicker and more solid than foundation, and
provides longer lasting, and more detailed coverage. Some formulations are meant only for the eye or only for the
face.
• Foundation, used to smooth out the face and cover spots or uneven skin coloration. Usually a liquid, cream, or
powder, as well as most recently, a light and fluffy mousse, which provides excellent coverage as well.[3]
Foundation primer can be applied before or after to get a smoother finish. Some primers come in powder or liquid
form to be applied before foundation as a base, while other primers come as a spray to be applied after you are
finished to help make-up last longer.
• Face powder, used to set the foundation, giving a matte finish, and also to conceal small flaws or blemishes.
• Rouge, blush or blusher, cheek coloring used to bring out the color in the cheeks and make the cheekbones appear
more defined. This comes in powder, cream, and liquid forms.[3]
• Contour powder/creams, used to define the face. It can be used to give the illusion of a slimmer face or to even
modify a person’s face shape as desired. Usually a few shades darker than ones own skin tone and matte in finish
to create the illusion of depth. A darker toned foundation/concealer can be used instead to contour to create a
more natural look.
• Highlight, used to draw attention to the high points of the face as well as to add glow to the face. It comes in
liquid, cream, and powder form. Often contains shimmer, but sometimes does not. A lighter toned
foundation/concealer can be used instead to highlight create a more natural look.
• Bronzer, used to give skin a bit of color by adding a golden or bronze glow.[3] Can come in either matte, semi
matte/satin, or shimmer finishes.
• Mascara is used to darken, lengthen, and thicken the eyelashes. It is available in natural colors such as brown and
black, but also comes in bolder colors such as blue, pink, or purple. There are many different formulas, including
waterproof for those prone to allergies or sudden tears. Often used after an eyelash curler and mascara primer.[3]
There are now also many mascaras with certain components to help lashes to grow longer and thicker. There are
specific minerals and proteins that are combined with the mascara that can benefit, as well as beautify.
Cosmetics 43

• Eyelash glue, Used to adhere false lashes to the eyes. Can come in
either clear or colored formulas.
• Eyebrow pencils, creams, waxes, gels and powders are used to color
and define the brows.[3]
• Nail polish, used to color the fingernails and toenails.[3][31]
• Setting Spray, used to keep applied makeup intact for long periods
of time. An alternative to setting spray is setting powder which may
be either pigmented or translucent.
Cosmetics can be also described by the physical composition of the
product. Cosmetics can be liquid or cream emulsions; powders, both
pressed and loose; dispersions; and anhydrous creams or sticks.
Eye shadow being applied
Makeup remover is the product used to remove the makeup products
applied on the skin. It is used for cleaning the skin for other
procedures, like applying any type of lotion at evening before the
person go to sleep.

Skin Care Products

Also included in the general category of cosmetics are skin care
products. These include creams and lotions to moisturize the face and
body which are often formulated for different skin types per range,
sunscreens to protect the skin from UV radiation and damage, skin
lighteners, and treatment products to repair or hide skin imperfections Broadway actor Jim Brochu applies make-up
(acne, wrinkles, dark circles under eyes, etc.), tanning oils to brown the before the opening night of a play.

skin.

For each skin type present, the correct types of products must be used
in order to maintain healthy and attractive skin.

Skin Types
There are five basic skin types, including:

1. Normal Skin

This type of skin has a fine, even and smooth surface due to having an The chin mask known as chutti for Kathakali, a
performing art in Kerala, India is considered the
ideal balance between oil and moisture contents and is therefore
thickest makeup applied for any art form.
neither greasy nor dry. People who have normal skin have small,
barely-visible pores. Thus, their skin appears clear and does not
develop spots and blemishes. This type of skin needs minimal and gentle treatment.

2. Dry Skin

Dry skin has a parched appearance and tends to flake easily. It is prone to wrinkles and lines due to the inability to
retain moisture, as well as, the inadequate production of sebum by sebaceous glands. Dry skin often has problems in
cold weather as it dries up even further. Constant protection in the form of a moisturizer by day and a moisture-rich
cream by night is essential.
Cosmetics 44

3. Oily Skin
As its name implies, this type of skin’s surface is slightly to moderately greasy, which is caused by the over secretion
of sebum. The excess oil on the surface of the skin draws dirt and dust from the environment to stick to it. Oily skin
is usually prone to black heads, white heads, spots and pimples. It needs to be cleansed thoroughly every day.

4. Combination Skin
This is the most common type of skin. As the name suggests, it is a combination of both oily and dry skin where
certain areas of the face are oily and the rest dry. The oily parts are usually found on a central panel, called T – Zone,
consisting of the forehead, nose and chin. The dry areas consist of the cheeks and the areas around the eyes and
mouth. In such cases, each part of the face should be treated accordingly where the dry areas are treated as for dry
skin and the central panel is treated as for oily skin. There are also skin care products made especially for those who
have combination skin.

5. Sensitive skin
Sensitive skin has a very fine texture and is excessively sensitive to changes in the climate. This skin type is easily
irritated, bruised and/or scarred from bleaching, waxing, threading, perfumes, temperature extremes, soap, shaving
creams, etc. People who belong to this skin type should avoid products with dyes, perfumes, or unnecessary
chemical ingredients that may aggravate the skin.

General Skin Care Routines

Cleansing
Cleansing is the first essential step to any daily skin care routine. Cleansing the face at least twice a day is suitable
for normal skin. If skin is oily, a more frequent cleansing or about four to five times a day is required. However,
products that are water-based and gentle are ideal so as to not over-dry the skin. For dry skin, it is best to avoid
frequent washing and a suitable oil-based cosmetic cleanser instead of soap is preferred. There are several
alternatives to soap and water cleansing. Cleansers can be in the form of creams, milks, lotions, gels and liquids. All
are a mixture of oil, wax and water which have been formulated to suit different skin types. A cotton -pad dipped in
fresh milk available at home, is an equally effective natural cleanser. To complete the cleansing process, the skin
must be rinsed with water. Some who wear long wearing foundation may find it beneficial to pre-cleanse the face
with a cleansing oil to remove any silicones left over from the foundation.

Masks
Essentially all face masks have some sort of a cleansing action. Various ingredients are used in the masks, depending
on the skin type. Clay forms an important constituent of many face masks that helps to remove dirt, sebum, and dead
skin to refresh and soften the skin surface. Fullers earth is a special type of clay often used in face packs. It contains
aluminium silicate and as it dries on the skin, it absorbs the superficial dead cells and blots up any excessive oil. It is
therefore excellent for oily skin but should not be used on dry skin. Kaolin is also a fine clay which removes grime,
oils and dead cells. Again it is best for oily skin and should be avoided on dry skin. Another ingredient of some of
the masks is a peeling or exfoliating agent which helps remove the top layer of dead cells from the skin, leaving
behind fresh youthful skin. Oatmeal and bran are the commonly used peelers. In addition, natural ingredients such as
cucumbers, curds, lemon juice and Brewer's Yeast are added to many masks to restore the acid / alkali balance of the
skin. There are three general forms that masks come in: Clay, Peel, and Sheet. The clay formulation is one of the
most common. It is usually composed of different clays to draw out the impurities in the skin. Peel masks usually
have a gel like consistency and are peeled off of the skin to help exfoliate. Sheet masks are becoming more common
in America, they are very popular in Asia. Sheet masks can be used to treat different skin concerns, but one of the
most popular concerns is skin brightening.
Cosmetics 45

Toning
Many skin care products include skin fresheners, toners and astringents which generally contain alcohol and water.
These products are used after cleansing the skin to freshen and tone up and remove any traces of dirt or impurities
from the skin, as well as restore the skin’s acid/ alkali balance. Non-alcoholic fresheners are for dry and sensitive
skin. Those with alcohol (astringent) are for oily skin. People with combination skin should use both kinds for the
different areas of their face.

Moisturizing
Regular use of a suitable moisturizer benefits the skin as it not only replaces water lost from the skin but also
prevents the loss of water. It protects the skin against the drying influences of the environment including the harsh
effects of the sun, cold and heat. Tinted moisturizers can be used under foundation cosmetics. It allows make-up to
remain moist. Using a moisturizer is particularly beneficial for dry skins. Oil free moisturizers are also available for
oily skins. There are two types of moisturizers: Oil - in water emulsions and water -in -oil emulsions. For normal and
combination skin, a water based moisturizer containing minimal oil is suitable. Sensitive and dry types of skin need
moisturizers containing a high content of oil.

Protecting
The sun is the most damaging environmental factor to the health and appearance of skin. Ultraviolet radiation from
sunlight can cause permanent damage to the skin causing it to sag, lose elasticity and form wrinkles. Severe sunburn
can even cause skin cancer. Therefore, sunscreen and SPF-foundations protect the skin against these damaging
effects. They also shield the skin from direct contact with dirt or pollutants in the air and help the skin retain
necessary moisture. Sunscreen's come in lotions and creams. A sunscreen with the sun protection factor (SPF) of
number 15 can block most of the sun's ultraviolet radiations before it can damage the skin. The SPF number
indicates the length of time that the product will protect the skin, i.e. 15 hours. Sunscreens should be applied at least
10 minutes before exposure to the sun to ensure proper absorption and effective protection.

Ingredients
While there is assurance from the largest cosmetic companies that ingredients have passed quality tests and official
regulations, and are therefore generally safe to use, there is a growing preference for cosmetics that are without any
"synthetic" ingredients, especially those derived from petroleum. Once a niche market, handmade and certified
organic products are becoming more mainstream.
Ingredients' listings in cosmetics are highly regulated in many countries. The testing of cosmetic products on animals
is a subject of some controversy. It is now illegal in the United Kingdom, the Netherlands, and Belgium, and a ban
across the European Union came into effect in 2009. When purchasing cosmetics it is important to know that the
highest concentration of ingredients are listed first in the ingredients list on the packaging.

Organic and natural ingredients

Even though many cosmetic products are regulated, there are still health concerns regarding the presence of harmful
chemicals within these products. Aside from color additives, cosmetic products and their ingredients are not subject
to FDA regulation prior to their release into the market. It is only when a product is found to violate Federal Food,
Drug, and Cosmetic Act (FD&C Act) and Fair Packaging and Labeling Act (FPLA) after its release that the FDA
may start taking action against this violation.[12] With many new products released into the market every season, it is
hard to keep track of the safety of every product. Some products carry carcinogenic contaminant 1,4- dioxane. Many
cosmetic companies are coming out with "All natural" and organic products such as anti-ageing and anti-acne creams
based on Egg Oil which contains Omega-3 fatty acids and xanthophylls. All natural products contain mineral, egg
and plant ingredients and organic products are made with organic agricultural products. Products who claim they are
Cosmetics 46

organic are not, unless they are certified "USDA Organic."[32][33]

Mineral makeup
The term "mineral makeup" applies to a category of face makeup, including foundation, eye shadow, blush, and
bronzer, that is made with loose, dry mineral powders. Lipsticks, liquid foundations, and other liquid cosmetics, as
well as compressed makeups such as eye shadow and blush in compacts, are also often called mineral makeup if they
have the same primary ingredients as dry mineral makeups; however, liquid makeups must contain preservatives and
compressed makeups must contain binders, which the dry mineral makeups do not.

Ingredients
The main ingredients in mineral makeups are usually coverage pigments, such as zinc oxide and titanium dioxide,
both of which are also physical sunscreens.[34]
Other main ingredients include mica (Sericite) and pigmenting minerals, such as iron oxide, tin oxide, and
magnesium myristate.
Mineral makeup usually does not contain synthetic fragrances, preservatives, parabens, mineral oil, and chemical
dyes. Because of this, many dermatologists consider mineral makeup to be purer and kinder to the skin than makeup
that contains those ingredients.[35]
However, some mineral makeups contain Bismuth oxychloride, which can be irritating to the skin of sensitive
individuals. Others also contain talc, over which there is some controversy because of its comedogenic tendencies
(tendency to clog pores and therefore cause acne) and because some people are sensitive to talc.

Benefits
Because titanium dioxide and zinc oxide have anti-inflammatory properties, mineral makeups with those ingredients
can also have a calming effect on the skin, which is particularly important for those who suffer from inflammatory
problems such as rosacea. Zinc oxide is also anti-microbial,[36] so mineral makeups can be beneficial for those with
acne.
Mineral makeup is noncomedogenic (as long as it doesn't contain talc), and it offers a mild amount of sun protection
(because of the titanium dioxide and zinc oxide).[37]
Because they don't contain liquid ingredients, mineral makeups can last in their containers indefinitely as long as the
user doesn't contaminate them with liquid.

Cosmetic industry
The cosmetic industry is a profitable business for most manufacturers of cosmetic products. By cosmetic products,
we understand anything that is intended for personal care such as skin lotions or sun lotions, makeup and other such
products meant to emphasize one's look. Given the technological development and the improvement of the
manufacturing process of cosmetics and not least due to the constantly increasing demand of such products, this
industry reported an important growth in terms of profit.
The cosmetic industry has not only grown only in the United States, but also in various parts of the world which
have become famous for their cosmetic precuts. Some of these include France, Germany, Italy and Japan. It has been
estimated that in Germany, the cosmetic industry generated sales of EUR 12.6 billion at retail sales, in 2008[38]
which made of German cosmetic industry the 3rd in the world, after Japan and the United States. Also, it has been
shown that in the same country, this industry has grown with nearly 5 percent in one year, from 2007 to 2008. The
exports of Germany in this industry reached in 2008 EUR 5.8 billion whereas the imports of cosmetics totaled EUR
3 billion.[38] The main countries that export cosmetics to Germany are France, Switzerland, the United States and
Italy and they mainly consist of makeup and fragrances or perfumes for women.
Cosmetics 47

After the United States, Japan is the second largest market for cosmetics in the world, a market worth about JPY 1.4
trillion per year.[39]
The worldwide cosmetics and perfume industry currently generates an estimated annual turnover of US$170 billion
(according to Eurostaf - May 2007). Europe is the leading market, representing approximately €63 billion, while
sales in France reached €6.5 billion in 2006, according to FIPAR (Fédération des Industries de la Parfumerie - the
French federation for the perfume industry).[40] France is another country in which the cosmetic industry plays an
important role, both nationally and internationally. Most products on whose label it is stated "Made in France" are
valued on the international market. According to data from 2008, the cosmetic industry has risen constantly in
France, for 40 consecutive years. In 2006, this industrial sector reached a record level of EUR 6.5 billion. Famous
cosmetic brands produced in France include Vichy, Yves Saint Laurent, Yves Rocher and many others.
The Italian cosmetic industry is also an important player in the European cosmetic market. Although not as large as
in other European countries, the cosmetic industry in Italy was estimated to reach EUR 9 billion in 2007.[41] The
Italian cosmetic industry is however dominated by hair and body products and not makeup as in many other
European countries. In Italy, hair and body products make up approximately 30% of the cosmetic market. Makeup
and facial care however are the first cosmetic products to be exported in the United States.
Due to the popularity of cosmetics, especially fragrances and perfumes, many designers who are not necessarily
involved in the cosmetic industry came up with different perfumes carrying their names. Moreover, some actors and
singers have their own perfume line (such as Celine Dion). The designer perfumes are, like any other designer
products, the most expensive in the industry as the consumer pays not only for the product but also for the brand.
Famous Italian fragrances are produced by Giorgio Armani, Dolce and Gabbana and so on.
Recently, Procter & Gamble, which sells CoverGirl and Dolce & Gabbana makeup, funded a study[42] concluding
that makeup makes women seem more competent.[43] Due to the source of funding, the quality of this Boston
University study comes into question.
The cosmetic industry worldwide seems to be continuously developing, now more than ever with the advent of the
Internet companies. Many famous companies sell their cosmetic products online also in countries in which they do
not have representatives.

Legislation
The main directive in the EU affecting the manufacture, labelling and supply of cosmetics and personal care
products is the Cosmetics Directive 76/768/EEC.[44] It applies to all the countries of the EU as well as Iceland,
Norway and Switzerland. These regulations apply to single-person companies making or importing just one product
as well as to large multinationals. In the UK the directive is enacted as the Cosmetic Product (safety) Regulations
2008. [45] For manufacturers and importers of cosmetic products it is necessary to comply to the applying regulations
in order to sell their products. In this industry it is common fall back on a suitably qualified person, such as an
independent third party inspection and testing company, to verify the cosmetics’ compliance against the requirements
of applicable cosmetic regulations and other relevant legislation, including REACH, GMP, hazardous substances,
etc. [46][47]
In the European Union, the circulation of cosmetic products and their safety are law subjects since 1976. One of the
newest amendments of the directive concerning cosmetic industry comes as a result of the attempt to ban animal
testing. Therefore, testing cosmetic products on animals is illegal in the European Union from September 2004 and
testing separate ingredients of such products on animals is also prohibited by law starting with March 2009.[48]
In the U.S. the Food and Drug Administration (FDA) is the body making legislation in what concerns cosmetic
industry and its various aspects within the United States.[49] The FDA joined with thirteen other Federal agencies in
forming the Interagency Coordinating Committee on the Validation of Alternative Methods (ICCVAM) in 1997
which is an attempt to ban animal testing and find other methods to test the cosmetic products.[50]
Cosmetics 48

Cosmetic careers
An account executive is responsible for visiting all department and
specialty store counter sales and doors. They explain new products and
"gifts with purchase" (free items given out upon purchase of a certain
cosmetics item that costs more than a set amount).
A beauty adviser provides product advice based on the client's skin
care and makeup requirements. Beauty advisers can become certified
through the Anti-Aging Beauty Institute.

A professional make-up artist servicing a client

A cosmetician is a professional who provides facial and body

treatments for clients. The term cosmetologist is sometimes used
interchangeably with this term, but most commonly refers to a certified
professional. A freelance makeup artist provides clients with beauty
advice and cosmetics assistance—usually paid by the cosmetic
company by the hour, however they sometimes work as independently
without a company.

Professionals in cosmetics marketing careers manage research focus

Model Alek Wek receiving make-up from a
groups, promote the desired brand image, and provide other marketing professional.
services (sales forecasting, allocation to different retailers, etc.).
Many involved within the cosmetics industry often specialize in a certain area of cosmetics such as special effects
makeup or makeup techniques specific to the film, media and fashion sectors.

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Cosmetics 49

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story/ 0,11917,1021527,00. html), The Guardian, August 19, 2003. Retrieved February 27, 2008.
[27] Robertson, Julia; Fieldman, George and Hussey, Trevor (2008). ""Who wears Cosmetics?" Individual Differences and their Relationship
with Cosmetic Usage". Individual Differences Research 6 (1): 38–56.
[28] Cash, Thomas F.; Kathryn Dawson, Pamela Davis, Maria Bowen and Chris Galumbeck (April 11, 1988). "Effects of Cosmetics Use on the
Physical Attractiveness and Body Image of American College Women". The Journal of Social Psychology 129 (3): 349–355.
[29] Lewis, K.M.; Robkin, N., Gaska, K., Njoki, L. C. (March 2, 2011). "Investigating Motivations for Women's Skin Bleaching in Tanzani"
(http:/ / pwq. sagepub. com/ content/ 35/ 1/ 29). Psychology of Women Quarterly 35 (1): 29-37. .
[30] Traore, Adama; Kadeba, J., Niamba, P., Barro, F., Ouedraogo, L. (2005). "Use of cutaneous depigmenting products by women in two towns
in Burkina Faso: epidemiologic data, motivations, products and side effects". International Journal of Dermatology 44 (1): 30-32.
[31] [Link]
[32] Singer, Natasha. "Natural, Organic Beauty." New York Times. 1 Nov. 2007. 18 Mar. 2008
[33] http:/ / www. nytimes. com/ 2007/ 11/ 01/ fashion/ 01skin. html?_r=1& oref=slogin
[34] "mineral makeup - Wiktionary" (http:/ / en. wiktionary. org/ wiki/ mineral_makeup). [Link]. . Retrieved 2011-10-23.
[35] "The Lowdown on Mineral Makeup" (http:/ / www. webmd. com/ healthy-beauty/ features/ the-lowdown-on-mineral-makeup). WebMD.
p. 3. . Retrieved February 05, 2012.
[36] Padmavathy, Nagarajan; Vijayaraghavan, Rajagopalan (2008). "Enhanced bioactivity of ZnO nanoparticles—an antimicrobial study" (free
download pdf). Science and Technology of Advanced Materials 9 (3): 035004. doi:10.1088/1468-6996/9/3/035004.
[37] Palladino, Lisa (2009-12-07). "What Is Mineral Makeup?" (http:/ / www. luxist. com/ 2009/ 12/ 07/ what-is-mineral-makeup/ ). [Link].
. Retrieved 2011-10-23.
[38] "Cosmetic Industry" (http:/ / www. german-business-portal. info/ GBP/ Navigation/ en/ Business-Location/ Manufacturing Industries/
cosmetics-industry,did=326082. html). . Retrieved 2010-08-04.
[39] "Blueprint for a Cosmetics Empire" (http:/ / www. japaninc. com/ article. php?articleID=1390). . Retrieved 2010-08-04.
[40] "France continues to lead the way in cosmetics" (http:/ / www. clickpress. com/ releases/ Detailed/ 82987005cp. shtml). . Retrieved
2010-08-04.
[41] "Cosmetics - Europe (Italy) 2008 Marketing Research" (http:/ / researchwikis. com/
Cosmetics_-_Europe_(Italy)_2008_Marketing_Research). . Retrieved 2010-08-04.
[42] "Cosmetics as a Feature of the Extended Human Phenotype: Modulation of the Perception of Biologically Important Facial Signals" (http:/ /
www. plosone. org/ article/ info:doi/ 10. 1371/ journal. pone. 0025656). Plos One. . Retrieved 2011-10-23.
[43] "Makeup Makes Women Appear More Competent: Study" (http:/ / www. nytimes. com/ 2011/ 10/ 13/ fashion/
makeup-makes-women-appear-more-competent-study. html?_r=1). The New York Times. 2011-10-12. .
[44] [ http:/ / ec. europa. eu/ consumers/ sectors/ cosmetics/ documents/ directive/ index_en. htm EU Cosmetics Directive]
[45] [ http:/ / www. legislation. gov. uk/ uksi/ 2008/ 1284/ introduction/ made Cosmetic Product (safety) Regulations 2008]
[46] [ http:/ / www. bis. gov. uk/ policies/ consumer-issues/ product-safety/ cosmetic-products-safety-regulations-2008-as-amended Cosmetic
Products Safety Regulations]
[47] [ http:/ / www. sgs. com/ en/ Consumer-Goods-Retail/ Personal-and-Home-Care/ Cosmetics. aspx Cosmetic Testing]
[48] "Regulatory context" (http:/ / ec. europa. eu/ consumers/ sectors/ cosmetics/ animal-testing/ index_en. htm). . Retrieved 2010-08-04.
[49] [ http:/ / www. fda. gov/ RegulatoryInformation/ Legislation/ FederalFoodDrugandCosmeticActFDCAct/ default. htm Federal Food, Drug,
and Cosmetic Act]
Cosmetics 50

[50] "Animal Testing" (http:/ / www. fda. gov/ Cosmetics/ ProductandIngredientSafety/ ProductTesting/ ucm072268. htm). . Retrieved
2010-08-04.

Further reading
• Winter, Ruth (2005) [2005] (in English). A Consumer's Dictionary of Cosmetic Ingredients: Complete
Information About the Harmful and Desirable Ingredients in Cosmetics (Paperback). US: Three Rivers Press.
ISBN 1-4000-5233-5.
• Begoun, Paula (2003) [2003] (in English). Don't Go to the Cosmetics Counter Without Me(Paperback). US:
Beginning Press. ISBN 1-877988-30-8.
• Carrasco, Francisco (2009) [2009] (in Spanish). Diccionario de Ingredientes Cosmeticos(Paperback). Spain:
[Link]. ISBN 978-84-613-4979-1.
Vegetable fats and oils 51

Vegetable fats and oils

Plant oils

Olive oil

Types

Vegetable fats (list)

Macerated (list)

Uses

Drying oil - Oil paint

Cooking oil

Fuel - Biodiesel

Components

Saturated fat

Monounsaturated fat

Polyunsaturated fat

Trans fat

Vegetable fats and oils are lipid materials derived from plants. Physically, oils are liquid at room temperature, and
fats are solid. Chemically, both fats and oils are composed of triglycerides, as contrasted with waxes which lack
glycerin in their structure. Although many plant parts may yield oil,[1] in commercial practice, oil is extracted
primarily from seeds.
The melting temperature distinction between oils and fats is imprecise, since definitions of room temperature vary,
and typically natural oils have a melting range instead of a single melting point since natural oils are not chemically
homogeneous. Although thought of as esters of glycerin and a varying blend of fatty acids, fats and oils also
typically contain free fatty acids, monoglycerides and diglycerides, and unsaponifiable lipids.
Vegetable fats and oils may or may not be edible. Examples of inedible vegetable fats and oils include processed
linseed oil, tung oil, and castor oil used in lubricants, paints, cosmetics, pharmaceuticals, and other industrial
applications.
Vegetable fats and oils 52

Uses of triglyceride vegetable oil

Oils extracted from plants have been used since ancient times and in many cultures. As an example, in a
4,000-year-old "kitchen" unearthed in Indiana's Charlestown State Park, archaeologist Bob McCullough of Indiana
University-Purdue University Fort Wayne found evidence that natives used large slabs of rock to crush hickory nuts,
then boiled them in water to extract the oil.[2]

Culinary uses
Many vegetable oils are consumed directly, or indirectly as ingredients in food – a role that they share with some
animal fats, including butter and ghee. The oils serve a number of purposes in this role:
• Shortening – to give pastry a crumbly texture.
• Texture – oils can serve to make other ingredients stick together less.
• Flavor – while less-flavorful oils command premium prices, some oils, such as olive, sesame or almond oil, may
be chosen specifically for the flavor they impart.
• Flavor base – oils can also "carry" flavors of other ingredients, since many flavors are present in chemicals that
are soluble in oil.
Secondly, oils can be heated, and used to cook other foods. Oils suitable for this purpose must have a high flash
point. Such oils include the major cooking oils – soy, canola, sunflower, safflower, peanut, cottonseed, etc. Tropical
oils, like palm oil and coconut oil, and rice bran oil, are particularly valued in Asian cultures for high temperature
cooking, because of their unusually high flash point.

Hydrogenated oils
Unsaturated vegetable fats and oils can be transformed through partial or complete "hydrogenation" into fats and oils
of higher melting point. The hydrogenation process involves "sparging" the oil at high temperature and pressure with
hydrogen in the presence of a catalyst, typically a powdered nickel compound. As each carbon-carbon double-bond
is chemically reduced to a single bond, two hydrogen atoms each form single bonds with the two carbon atoms. The
elimination of double bonds by adding hydrogen atoms is called saturation; as the degree of saturation increases, the
oil progresses toward being fully hydrogenated. An oil may be hydrogenated to increase resistance to rancidity
(oxidation) or to change its physical characteristics. As the degree of saturation increases, the oil's viscosity and
melting point increase.
The use of hydrogenated oils in foods has never been completely satisfactory. Because the center arm of the
triglyceride is shielded somewhat by the end fatty acids, most of the hydrogenation occurs on the end fatty acids,
thus making the resulting fat more brittle. A margarine made from naturally more saturated oils will be more plastic
(more "spreadable") than a margarine made from hydrogenated soy oil. While full hydrogenation produces largely
saturated fatty acids, partial hydrogenation results in the transformation of unsaturated cis fatty acids to trans fatty
acids in the oil mixture due to the heat used in hydrogenation. Since the 1970s, partially hydrogenated oils and their
trans fats have increasingly been viewed as unhealthy.
In the U.S., the Standard of Identity for a product labeled as "vegetable oil margarine" specifies only canola,
safflower, sunflower, corn, soybean, or peanut oil may be used.[3] Products not labeled "vegetable oil margarine" do
not have that restriction.
Vegetable fats and oils 53

Industrial uses
Vegetable oils are used as an ingredient or component in many manufactured products.
Many vegetable oils are used to make soaps, skin products, candles, perfumes and other personal care and cosmetic
products. Some oils are particularly suitable as drying oils, and are used in making paints and other wood treatment
products. Dammar oil (a mixture of linseed oil and dammar resin), for example, is used almost exclusively in treating
the hulls of wooden boats. Vegetable oils are increasingly being used in the electrical industry as insulators as
vegetable oils are not toxic to the environment, biodegradable if spilled and have high flash and fire points.
However, vegetable oils are less stable chemically, so they are generally used in systems where they are not exposed
to oxygen, and they are more expensive than crude oil distillate. Synthetic tetraesters, which are similar to vegetable
oils but with four fatty acid chains compared to the normal three found in a natural ester, are manufactured by
Fischer esterification. Tetraesters generally have high stability to oxidation and have found use as engine lubricants.
Vegetable oil is being used to produce biodegradable hydraulic fluid[4] and lubricant.[5]
One limiting factor in industrial uses of vegetable oils is that all such oils eventually chemically decompose, turning
rancid. Oils that are more stable, such as ben oil or mineral oil, are preferred for some industrial uses.
Vegetable-based oils, like castor oil, have been used as medicine and as lubricants for a long time. Castor oil has
numerous industrial uses, primarily due to the presence of hydroxyl groups on the fatty acid chains. Castor oil, and
other vegetable oils which have been chemically modified to contain hydroxyl groups, are becoming increasingly
important in the production of polyurethane plastic for many applications. These modified vegetable oils are known
as natural oil polyols.

Pet food additive

Vegetable oil is used in production of some pet foods. AAFCO defines vegetable oil, in this context, as the product
of vegetable origin obtained by extracting the oil from seeds or fruits which are processed for edible purposes. In
some poorer grade pet foods, the oil is listed only as "vegetable oil", without specifying the particular oil.[6]

Fuel
Vegetable oils are also used to make biodiesel, which can be used like conventional diesel. Some vegetable oil
blends are used in unmodified vehicles but straight vegetable oil, also known as pure plant oil, needs specially
prepared vehicles which have a method of heating the oil to reduce its viscosity. The vegetable oil economy is
growing and the availability of biodiesel around the world is increasing.
The NNFCC estimate that the total net greenhouse gas savings when using vegetable oils in place of fossil
fuel-based alternatives for fuel production, range from 18 to 100%.[7]

Production
To produce vegetable fats and oils, the oil first needs to be removed from the oil-bearing plant components, typically
seeds or legumes. This can be done via mechanical or chemical extraction. The extracted oil can then be purified
and, if required, refined or chemically altered.

Mechanical extraction
Oils can also be removed via mechanical extraction, termed "crushing" or "pressing." This method is typically used
to produce the more traditional oils (e.g., olive, coconut etc.), and it is preferred by most "health-food" customers in
the United States and in Europe. There are several different types of mechanical extraction.[8] Expeller-pressing
extraction is common, though the screw press, ram press, and Ghani (powered mortar and pestle) are also used. Oil
seed presses are commonly used in developing countries, among people for whom other extraction methods would
be prohibitively expensive; the Ghani is primarily used in India.[9] The amount of oil extracted using these methods
Vegetable fats and oils 54

varies widely, as shown in the following table for extracting mowrah butter in India:[10]

Method Percentage extracted

[11] 20–30%
Ghani

Expellers 34–37%

Solvent 40–43%

Solvent extraction
The processing vegetable oil in commercial applications is commonly done by chemical extraction, using solvent
extracts, which produces higher yields and is quicker and less expensive. The most common solvent is
petroleum-derived hexane. This technique is used for most of the "newer" industrial oils such as soybean and corn
oils.
Supercritical carbon dioxide can be used as a non-toxic alternative to other solvents.[12]

Hydrogenation
Oils may be partially hydrogenated to produce various ingredient oils. Lightly hydrogenated oils have very similar
physical characteristics to regular soy oil, but are more resistant to becoming rancid. Margarine oils need to be
mostly solid at 32 °C (90 °F) so that the margarine does not melt in warm rooms, yet it needs to be completely liquid
at 37 °C (98 °F), so that it doesn't leave a "lardy" taste in the mouth.
Hardening vegetable oil is done by raising a blend of vegetable oil and a catalyst in near-vacuum to very high
temperatures, and introducing hydrogen. This causes the carbon atoms of the oil to break double-bonds with other
carbons, each carbon forming a new single-bond with a hydrogen atom. Adding these hydrogen atoms to the oil
makes it more solid, raises the smoke point, and makes the oil more stable.
Hydrogenated vegetable oils differ in two major ways from other oils which are equally saturated. During
hydrogenation, it is easier for hydrogen to come into contact with the fatty acids on the end of the triglyceride, and
less easy for them to come into contact with the center fatty acid. This makes the resulting fat more brittle than a
tropical oil; soy margarines are less "spreadable". The other difference is that trans fatty acids (often called trans fat)
are formed in the hydrogenation reactor, and may amount to as much as 40 percent by weight of a partially
hydrogenated oil. Hydrogenated oils, especially partially hydrogenated oils with their higher amounts of trans fatty
acids are increasingly thought to be unhealthy.

Sparging
In the processing of edible oils, the oil is heated under vacuum to near the smoke point, and water is introduced at
the bottom of the oil. The water immediately is converted to steam, which bubbles through the oil, carrying with it
any chemicals which are water-soluble. The steam sparging removes impurities that can impart unwanted flavors and
odors to the oil.

Particular oils
For a more comprehensive list, see List of vegetable oils.
The following triglyceride vegetable oils account for almost all worldwide production, by volume. All are used as
both cooking oils and as SVO or to make biodiesel. According to the USDA, the total world consumption of major
vegetable oils in 2007/08 was:[13]
Vegetable fats and oils 55

Oil source World Notes

consumption
(million tons)

Palm 41.31 The most widely produced tropical oil, also used to make biofuel

Soybean 41.28 Accounts for about half of worldwide edible oil production

Rapeseed 18.24 One of the most widely used cooking oils, canola is a (trademarked) variety (cultivar) of rapeseed

Sunflower seed 9.91 A common cooking oil, also used to make biodiesel

Peanut 4.82 Mild-flavored cooking oil

Cottonseed 4.99 A major food oil, often used in industrial food processing

Palm kernel 4.85 From the seed of the African palm tree

Coconut 3.48 Used in soaps and cooking

Olive 2.84 Used in cooking, cosmetics, soaps and as a fuel for traditional oil lamps

Note that these figures include industrial and animal feed use. The majority of European rapeseed oil production is
used to produce biodiesel, or used directly as fuel in diesel cars which may require modification to heat the oil to
reduce its higher viscosity. The suitability of the fuel should come as little surprise, as Rudolf Diesel originally
designed his engine to run on peanut oil.
Other significant triglyceride oils include:
• Corn oil, one of the most common cooking oils
• Grape seed oil, used in cooking and cosmetics
• Hazelnut and other nut oils
• Linseed oil, from flax seeds
• Rice bran oil, from rice grains
• Safflower oil, a flavorless and colorless cooking oil
• Sesame oil, used as a cooking oil, and as a massage oil, particularly in India

History in North America

While olive oil and other pressed oils have been around for millennia, Procter & Gamble researchers were innovators
when they started selling cottonseed oil as a creamed shortening, in 1911. Ginning mills were happy to have
someone haul away the cotton seeds. Procter & Gamble researchers learned how to extract the oil, refine it, partially
hydrogenate it (causing it to be solid at room temperature and thus mimic natural lard), and can it under nitrogen gas.
Compared to the rendered lard Procter & Gamble was already selling to consumers, Crisco was cheaper, easier to stir
into a recipe, and could be stored at room temperature for two years without turning rancid. (Procter & Gamble sold
their fats and oils brands – Jif and Crisco – to The J.M. Smucker Co. in 2002.)
Soybeans were an exciting new crop from China in the 1930s. Soy was protein-rich, and the medium viscosity oil
was high in polyunsaturates. Henry Ford established a soybean research laboratory, developed soybean plastics and a
soy-based synthetic wool, and built a car "almost entirely" out of soybeans.[14] Roger Drackett had a successful new
product with Windex, but he invested heavily in soybean research, seeing it as a smart investment.[15] By the 1950s
and 1960s, soybean oil had become the most popular vegetable oil in the US.
In the mid-1970s, Canadian researchers developed a low-erucic-acid rapeseed cultivar. Because the word "rape" was
not considered optimal for marketing, they coined the name "canola" (from "Canada Oil low acid"). The U.S. Food
and Drug Administration approved use of the canola name in January 1985,[16] and U.S. farmers started planting
large areas that spring. Canola oil is lower in saturated fats, and higher in monounsaturates and is a better source of
omega-3 fats than other popular oils. Canola is very thin (unlike corn oil) and flavorless (unlike olive oil), so it
Vegetable fats and oils 56

largely succeeds by displacing soy oil, just as soy oil largely succeeded by displacing cottonseed oil.

Used oil
A large quantity of used vegetable oil is produced and recycled, mainly from industrial deep fryers in potato
processing plants, snack food factories and fast food restaurants.
Recycled oil has numerous uses, including use as a direct fuel, as well as in the production of biodiesel, soap, animal
feed, pet food, detergent, and cosmetics. It's traded as the commodity, yellow grease.
Since 2002, an increasing number of European Union countries have prohibited the inclusion of recycled vegetable
oil from catering in animal feed. Used cooking oils from food manufacturing, however, as well as fresh or unused
cooking oil, continue to be used in animal feed.[17]

Negative health effects

Hydrogenated oils have been shown to cause what is commonly termed the "double deadly effect", raising the level
of LDLs and decreasing the level of HDLs in the blood, increasing the risk of blood clotting inside blood vessels.[18]
A high consumption of omega-6 polyunsaturated fatty acids (PUFAs), which are found in most types of vegetable oil
(e.g. soybean oil, corn oil – the most consumed in USA, sunflower oil, etc.) may increase the likelihood that
postmenopausal women will develop breast cancer.[19] A similar effect was observed on prostate cancer in mice.[20]
Plant based oils high in monounsaturated fatty acids, such as olive oil, peanut oil, and canola oil are relatively low in
omega-6 PUFAs and can be used in place of high-polyunsaturated oils.

Product labeling
There is increasing concern that the product labeling that includes "vegetable fat" or "vegetable oil" in its list of
ingredients masks the identity of the fats or oils present. This has been made more pressing as concerns have been
raised over the environmental impact of palm oil in particular, especially given the predominance of palm oil.[21]

Notes and references

[1] Compare, for example, the list of raw materials from which essential oils are extracted
[2] "4,000-year-old 'kitchen' unearthed in Indiana" (http:/ / www. stonepages. com/ news/ archives/ 001708. html). Archaeo News. January 26,
2006. . Retrieved 2006-07-31.
[3] "Margarine" (http:/ / www. accessdata. fda. gov/ scripts/ cdrh/ cfdocs/ cfcfr/ CFRSearch. cfm?CFRPart=166& showFR=1). Code of Federal
Regulations Title 21, Chapter I, Subchapter B, Part 166. U.S. Food and Drug Administration. April 1, 2011. . Retrieved 2011-11-01.
[4] Linda McGraw (April 19, 2000). "Biodegradable Hydraulic Fluid Nears Market" (http:/ / www. ars. usda. gov/ is/ pr/ 2000/ 000419. htm).
USDA. . Retrieved 2006-09-29.
[5] "Cass Scenic Railroad, West Virginia" (http:/ / www. gwrranci. org/ gallery/ 20060824/ ). GWWCA. . Retrieved 2011-11-01.
[6] "Ingredients to avoid" (http:/ / www. dogfoodproject. com/ index. php?page=badingredients). The Dog Food Project. . Retrieved 2007-06-26.
[7] National Non-Food Crops Centre. GHG Benefits from Use of Vegetable Oils for Electricity, Heat, Transport and Industrial Purposes,
NNFCC 10-016 (http:/ / www. nnfcc. co. uk/ tools/
ghg-benefits-from-use-of-vegetable-oils-for-electricity-heat-transport-and-industrial-purposes-nnfcc-10-016)
[8] "Kalu (oil presser)" (http:/ / banglapedia. search. com. bd/ HT/ K_0050. htm). Banglapedia. . Retrieved 2006-11-12.
[9] Janet Bachmann. "Oilseed Processing for Small-Scale Producers" (http:/ / www. attra. org/ attra-pub/ oilseed. html). . Retrieved 2006-07-31.
[10] B.L. Axtell from research by R.M. Fairman (1992). "Illipe" (http:/ / www. fao. org/ es/ faodef/ fdef14e. htm). Minor oil crops. FAO. .
Retrieved 2006-11-12.
[11] "Ghani" (http:/ / banglapedia. search. com. bd/ HT/ G_0089. htm). Banglapedia. . Retrieved 2006-11-12. A ghani is a traditional Indian oil
press, driven by a horse or ox.
[12] Eisenmenger, Michael; Dunford, Nurhan T.; Eller, Fred; Taylor, Scott; Martinez, Jose (2006). "Pilot-scale supercritical carbon dioxide
extraction and fractionation of wheat germ oil". Journal of the American Oil Chemists' Society 83 (10): 863. doi:10.1007/s11746-006-5038-6.
[13] January 2009 (http:/ / www. fas. usda. gov/ oilseeds/ circular/ 2009/ January/ Oilseedsfull0109. pdf). Oilseeds: World Market and Trade.
FOP 1-09. USDA. 2009-01-12. ., Table 03: Major Vegetable Oils: World Supply and Distribution at Oilseeds: World Markets and Trade
Monthly Circular (http:/ / www. fas. usda. gov/ oilseeds/ circular/ Current. asp)
Vegetable fats and oils 57

[14] "Soybean Car" (http:/ / www. thehenryford. org/ research/ soybeancar. aspx). Popular Research Topics. Benson Ford Research Center. .
Retrieved 2006-10-23.
[15] Horstman, Barry M (1999-05-21). "Philip W. Drackett: Earned profits, plaudits" (http:/ / web. archive. org/ web/ 20051205202014/ http:/ /
www. cincypost. com/ living/ 1999/ drack052199. html). The Cincinnati Post (E. W. Scripps Company). Archived from the original (http:/ /
www. cincypost. com/ living/ 1999/ drack052199. html) on 2005-12-05. . Retrieved 2006-10-22.
[16] "Canola oil" (http:/ / web. archive. org/ web/ 20060617234030/ http:/ / www. fda. gov/ bbs/ topics/ ANSWERS/ ANS00198. html).
Archived from the original (http:/ / www. fda. gov/ bbs/ topics/ ANSWERS/ ANS00198. html) on 2006-06-17. . Retrieved 2006-07-31.
[17] "Waste cooking oil from catering premises" (http:/ / www. food. gov. uk/ foodindustry/ guidancenotes/ foodguid/ wastecookingoil). .
Retrieved 2006-07-31.
[18] "Vegetable Oil – Everything You Need To Know About Vegetable Oils" (http:/ / vegetableoils. org/ vegetableoil/ ). .
[19] Emily Sonestedt, Ulrika Ericson, Bo Gullberg, Kerstin Skog, Håkan Olsson, Elisabet Wirfält (2008). "Do both heterocyclic amines and
omega-6 polyunsaturated fatty acids contribute to the incidence of breast cancer in postmenopausal women of the Malmö diet and cancer
cohort?". The International Journal of Cancer (UICC International Union Against Cancer) 123 (7): 1637–1643. doi:10.1002/ijc.23394.
PMID 18636564.
[20] Berquin IM, Min Y, Wu R, et al. (July 2007). "Modulation of prostate cancer genetic risk by omega-3 and omega-6 fatty acids". The Journal
of Clinical Investigation 117 (7): 1866–75. doi:10.1172/JCI31494. PMC 1890998. PMID 17607361.
[21] An issue highlighted in documentaries such as Dying for a Biscuit on BBC Panorama http:/ / www. bbc. co. uk/ programmes/ b00r4t3s

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• Berry, E.M. and Hirsch, J. (1986). "Does dietary linolenic acid influence blood pressure?". American Journal of
Clinical Nutrition 44: 336–340.
• Beyers, E.C. and Emken, E.A. (1991). "Metabolites of cis, trans, and trans, cis isomers of linoleic acid in mice
and incorporation into tissue lipids". Biochimica et Biophysica Acta 1082: 275–284.
• Birch, D.G., Birch, E.E., Hoffman, D.R., and Uauy, R.D. (1992). "Retinal development in very-low-birth-weight
infants fed diets differing in omega-3 fatty acids". Investigative Ophthalmology and Visual Science 33 (8):
2365–2376.
• Birch, E.E., Birch, D.G., Hoffman, D.R., and Uauy, R. (1992). "Dietary essential fatty acid supply and visual
acuity development". Investigative Ophthalmology and Visual Science 33 (11): 3242–3253.
• Brenner, R.R. (1989). A.J. Vergroesen and M. Crawford. ed. Factors influencing fatty acid chain elongation and
desaturation, in the role of fats in human nutrition (2 ed.). Academic Press, London. pp. 45–79.
• "Report of the task force on trans fatty acids". British Nutrition Foundation. 1987.
• "Central Soya annual report". 1979.
• Emken, E. A. (1984). "Nutrition and biochemistry of trans and positional fatty acid isomers in hydrogenated oils".
Annual Reviews of Nutrition 4: 339–376.
• Enig, M.G., Atal, S., Keeney, M and Sampugna, J. (1990). "Isomeric trans fatty acids in the U.S. diet". Journal of
the American College of Nutrition 9: 471–486.
• Ascherio, A., Hennekens, C.H., Baring, J.E., Master, C., Stampfer, M.J. and Willett, W.C. (1994). "Trans fatty
acids intake and risk of myocardial infarction". Circulation 89: 94–101.
• Gurr, M.I. (1983). "Trans fatty acids: Metabolic and nutritional significance". Bulletin of the International Dairy
Federation 166: 5–18.
• Hui Y. H., ed. Bailey's Industrial Oil and Fat Products.
• Koletzko, B. (1992). "Trans fatty acids may impair biosynthesis of long-chain polyunsaturates and growth in
man". Acta Paediatrica 81: 302–306.
• Lief, Alfred (1958). It floats: The story of Procter & Gamble. Rinehart.
• MacMillen, Harold W. (1967). Mr. Mac and Central Soya: the foodpower story. Newcomen Society.
• Marchand, C.M. (1982). "Positional isomers of trans-octadecenoic acids in margarine". Canadian Institute of
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Vegetable fats and oils 58

• Mensink, R.P., Zock, P.L., Katan, M.B. and Hornstra, G. (1992). "Effect of dietary cis-and trans-fatty acids on
serum lipoprotein[a] levels in humans". Journal of Lipid Research 33: 1493–1501.
• Siguel, E.N. and Lerman, R.H. (1993). "Trans fatty acid patterns in patients with angiographically documented
coronary artery disease". American Journal of Cardiology 71: 916–920.
• Troisi, R., Willett, W.C. and Weiss, S.T. (1992). "Trans-fatty acid intake in relation to serum lipid concentrations
in adult men". American Journal of Clinical Nutrition 56: 1019–1024.
• Willett, W.C., Stampfer, M.J., Manson, J.E., Colditz, G.A., Speizer, F.E., Rosner, B.A., Sampson, L.A. and
Hennekens, C.H. (1993). "Intake of trans fatty acids and risk of coronary heart disease among women". The
Lancet 341: 581–585.

Further reading
• Gupta, Monoj K. (2007). Practical guide for vegetable oil processing. AOCS Press, Urbana, Illinois.
ISBN 978-1-893997-90-5.
• Jee, Michael, ed. (2002). Oils and Fats Authentication. Blackwell Publishing, Oxford, England.
ISBN 1-84127-330-9.
• Salunkhe, D.K., Chavan, J.K., Adsule, R.N. and Kadam, S.S. (1992). World Oilseeds – Chemistry, Technology,
and Utilization. Van Nostrand Reinhold, New York. ISBN 0-442-00112-6.

External links
• "Fats and Cholesterol: Out with the Bad, In with the Good – What Should You Eat? – The Nutrition Source –
Harvard School of Public Health" ([Link]
fats-full-story/[Link]). [Link]. Retrieved 2009-05-04.
• "Vegetable oil yields, characteristics: Journey to Forever" ([Link]
[Link]. Retrieved 2009-05-04.
• "National Non-Food Crops Centre" ([Link] [Link]. Retrieved 2009-05-04.
Palm oil 59

Palm oil
Palm oil, is an edible plant oil derived from the mesocarp of the fruit
of the oil palm (Elaeis guineensis).[1] It is not to be confused with palm
kernel oil derived from the kernel of the same fruit[2], or coconut oil
derived from the kernel of the coconut palm (Cocos nucifera). The
differences are in color (raw palm kernel oil lacks carotenoids and is
not red), and in saturated fat content: Palm mesocarp oil is 41%
saturated, while Palm Kernel oil and Coconut oil are 81% and 86%
saturated respectively [3]

Naturally reddish in color because of a high beta-carotene content,

palm oil, along with coconut oil, is one of the few highly saturated
vegetable fats. It is semi-solid at room temperatures and contains
several saturated and unsaturated fats in the forms of glyceryl laurate
(0.1%, saturated), myristate (1%, saturated), palmitate (44%,
saturated), stearate (5%, saturated), oleate (39%, monounsaturated),
linoleate (10%, polyunsaturated), and alpha-linolenate (0.3%,
polyunsaturated).[4] Like all vegetable oils, palm oil does not contain
cholesterol,[5][6] although saturated fat intake increases both LDL[7]
and HDL[8] cholesterol.

Palm oil is a common cooking ingredient in the tropical belt of Africa, Palm oil from Ghana with its natural dark color
Southeast Asia and parts of Brazil. Its increasing use in the commercial visible, 2 litres
food industry in other parts of the world is buoyed by its lower cost[9]
and the high oxidative stability (saturation) of the refined product when
used for frying.[10][11]
The use of palm oil in food products attracts the concern of
environmental activist groups: the high oil yield of the trees have led,
in parts of Indonesia, to removal of forest in order to make space for
oil-palm monoculture: this has resulted in acreage losses of the natural
habitat of the orangutan [12]

Palm oil block showing the lighter color that

results from boiling.
Palm oil 60

History
Palm oil (from the African oil palm, Elaeis guineensis) has long
been recognized in West African countries, and is widely used as a
cooking oil. European merchants trading with West Africa
occasionally purchased palm oil for use as a cooking oil in Europe,
but palm oil was not able to supplant olive oil or butter, and
culinary uses of palm oil remained rare outside West Africa until
after commercial oil palm plantation development in non-African
tropical regions. In the Asante Confederacy, state-owned slaves
built large plantations of oil palm trees, while in the neighbouring
Oil palm tree (Elaeis guineensis)
Kingdom of Dahomey, King Ghezo passed a law in 1856
forbidding his subjects from cutting down oil palms.

Palm oil became a highly sought-after commodity by British traders, for use as an industrial lubricant for machinery
during Britain's Industrial Revolution[13]. Palm oil formed the basis of soap products, such as Lever Brothers' (now
Unilever) "Sunlight" soap, and the American Palmolive brand.[14] By around 1870, palm oil constituted the primary
export of some West African countries, such as Ghana and Nigeria, although this was overtaken by cocoa in the
1880s.

Research
In the 1960s, research and development (R&D) in oil palm breeding began to expand after Malaysia's Department of
Agriculture established an exchange program with West African economies and four private plantations formed the
Oil Palm Genetics Laboratory.[15] The government also established Kolej Serdang, which became the Universiti
Pertanian Malaysia (UPM) in the 1970s to train agricultural and agro-industrial engineers and agro-business
graduates to conduct research in the field.
In 1979, following strong lobbying from oil palm planters and support from the Malaysian Agricultural Research and
Development Institute (MARDI) and UPM, the government set up the Palm Oil Research Institute of Malaysia
(Porim).[16] B.C. Sekhar was instrumental in helping Porim recruit and train scientists to undertake R&D in oil palm
tree breeding, palm oil nutrition and potential oleochemical use. Sekhar, as founder and chairman, pushed Porim to
be a public-and-private-coordinated institution. As a result, Porim (renamed Malaysian Palm Oil Board in 2000)
became Malaysia's top research entity commercializing 20% of its innovations, compared to 5% among local
universities.

Nutrition
Further information: palmitic acid
Many processed foods contain palm oil as an ingredient.[17]
Palm oil is composed of fatty acids, esterified with glycerol just like any ordinary fat. It is high in saturated fatty
acids. Palm oil gives its name to the 16-carbon saturated fatty acid palmitic acid. Monounsaturated oleic acid is also
a constituent of palm oil. Unrefined palm oil is a large natural source of tocotrienol, part of the vitamin E family.[18]
The approximate concentration of fatty acids in palm oil is:[19]
Palm oil 61

Fatty acid content of palm oil

Type of fatty acid pct

Myristic saturated C14 1.0%

Palmitic saturated C16 43.5%

Stearic saturated C18 4.3%

Oleic monounsaturated C18 36.6%

Linoleic polyunsaturated C18 9.1%

Other/Unknown 5.5%

red: Saturated; orange: Monounsaturated; blue: Polyunsaturated

Red palm oil

Red palm oil gets its name from its characteristic dark red color, which comes from carotenes, such as
alpha-carotene, beta-carotene and lycopene, the same nutrients that give tomatoes, carrots and other fruits and
vegetables their rich colors.
Red palm oil contains at least 10 other carotenes, along with tocopherols and tocotrienols (members of the vitamin E
family), CoQ10, phytosterols, and glycolipids.[20] In a 2007 animal study, South African scientists found
consumption of red palm oil significantly decreased p38-MAPK phosphorylation in rat hearts subjected to a
high-cholesterol diet.[21]
Since the mid-1990s, red palm oil has been cold-pressed and bottled for use as cooking oil, and blended into
mayonnaise and salad oil.[22] Red palm oil antioxidants like tocotrienols and carotenes are added to foods and
cosmetics because of their purported health benefits.[23][24][25]
In a 2004 joint study between the Kuwait Institute for Scientific Research and the Malaysian Palm Oil Board, the
scientists found cookies, being higher in fat content than bread, are a better vehicle for red palm oil
phytonutrients.[26]
In a 2009 study, scientists in Spain tested the acrolein emission rates from the deep-frying of potatoes in red palm,
olive and polyunsaturated oils. They found higher acrolein emission rates from the polyunsaturated oils. The
scientists characterized red palm oil as "mono-unsaturated".[27]
Frying French fries in red palm oil gives them an attractive color.[28]

Refined, bleached, deodorized palm oil

Palm oil products are made using milling and refining processes: first using fractionation, with crystallization and
separation processes to obtain solid (stearin), and liquid (olein) fractions. Then melting and degumming removes
impurities. Then the oil is filtered and bleached. Next, physical refining removes smells and coloration, to produce
"refined bleached deodorized palm oil", or RBDPO, and free sheer fatty acids, which are used as an important raw
material in the manufacture of soaps, washing powder and other hygiene and personal care products. RBDPO is the
basic oil product sold on the world's commodity markets, although many companies fractionate it further into palm
olein, for cooking oil or other products.[29]
Splitting of oils and fats by hydrolysis, or under basic conditions saponification, yields fatty acids, with glycerin
(glycerol) as a byproduct. The split-off fatty acids are a mixture ranging in carbon chain length from C4 to C18,
depending on the type of oil or fat.[30][31]
Palm oil 62

Uses
Derivatives of palmitic acid were used in combination with naphtha during World War II to produce napalm
(aluminum naphthenate and aluminum palmitate).[32]
Many processed foods contain palm oil as an ingredient.[17] The highly saturated nature of palm oil, while
undesirable from the health perspective, renders it solid at room temperature in temperate regions, making it a cheap
substitute for butter in uses where solid fat is desirable, such as the making of pastry dough and baked goods: in this
respect, it is less of a health-hazard than the alternative substitute of partially hydrogenated trans fat.

Biodiesel
Palm oil, like other vegetable oils, can be used to create biodiesel, as either a simply processed palm oil mixed with
petrodiesel, or processed through transesterification to create a palm oil methyl ester blend, which meets the
international EN 14214 specification. Glycerin is a byproduct of transesterification. The actual process used to
produce biodiesel around the world varies between countries and the requirements of different markets.
Next-generation biofuel production processes are also being tested in relatively small trial quantities.
The IEA predicts biofuels usage in Asian countries will remain modest. But as a major producer of palm oil, the
Malaysian government is encouraging the production of biofuel feedstock and the building of palm oil biodiesel
plants. Domestically, Malaysia is preparing to change from diesel to biofuels by 2008, including drafting legislation
that will make the switch mandatory. From 2007, all diesel sold in Malaysia must contain 5% palm oil. Malaysia is
emerging as one of the leading biofuel producers, with 91 palm oil plants approved and a handful now in
operation.[33]
On 16 December 2007, Malaysia opened its first biodiesel plant in the state of Pahang, with an annual capacity of
100,000 tonnes, and which also produces byproducts in the form of 4,000 tonnes of palm fatty acid distillate and
12,000 tonnes of pharmaceutical-grade glycerine.[34] Neste Oil of Finland plans to produce 800,000 tonnes of
biodiesel per year from Malaysian palm oil in a new Singapore refinery from 2010, which will make it the largest
biofuel plant in the world,[35] and 170,000 tpa from its first second-generation plant in Finland from 2007-8, which
can refine fuel from a variety of sources. Neste and the Finnish government are using this paraffinic fuel in some
public buses in the Helsinki area as a small scale pilot.[36][37]
First generation biodiesel production from palm oil is in demand globally. Palm oil is also a primary substitute for
rapeseed oil in Europe, which too is experiencing new demand for biodiesel purposes. Palm oil producers are
investing heavily in the refineries needed for biodiesel. In Malaysia, companies have been merging, buying others
out and forming alliances to obtain the economies of scale needed to handle the high costs caused by increased
feedstock prices. New refineries are being built across Asia and Europe.[38]
As the food vs. fuel debate mounts, research is turning to biodiesel production from waste. In Malaysia, an estimated
50,000 tonnes of used frying oils, both vegetable oils and animal fats, are disposed of yearly, without treatment, as
wastes. In a 2006 study, researchers found used frying oil (mainly palm olein), after pretreatment with silica gel, is a
suitable feedstock for conversion to methyl esters by catalytic reaction using sodium hydroxide. The methyl esters
produced have fuel properties comparable to those of petroleum diesel, and can be used in unmodified diesel
engines.[39]
A 2009 study by scientists at Malaysian Science University concluded palm oil, compared to other vegetable oils, is
a healthy source of edible oil and at the same time, available in quantities that can satisfy global demand for
biodiesel. Oil palm planting and palm oil consumption circumvents the food vs. fuel debate because it has the
capacity to fulfill both demands simultaneously.[40] By 2050, a British scientist estimates global demand for edible
oils will probably be around 240 million tonnes, nearly twice 2008 consumption. Most of the additional oil may be
palm oil, which has the lowest production cost of the major oils, but soybean oil production will probably also
increase. An additional 12000000 hectares (unknown operator: u'strong' sq mi) of oil palms may be required, if
Palm oil 63

average yields continue to rise as in the past. This need not be at the expense of forest; oil palm planted on
anthropogenic grassland could supply all the oil required for edible purposes in 2050.[41]

Market
According to Hamburg-based Oil World trade journal, in 2008, global production of oils and fats stood at 160
million tonnes. Palm oil and palm kernel oil were jointly the largest contributor, accounting for 48 million tonnes or
30% of the total output. Soybean oil came in second with 37 million tonnes (23%). About 38% of the oils and fats
produced in the world were shipped across oceans. Of the 60.3 million tonnes of oils and fats exported around the
world, palm oil and palm kernel oil make up close to 60%; Malaysia, with 45% of the market share, dominates the
palm oil trade.[42]

Regional production

Indonesia
As of 2009, Indonesia was the largest producer of palm oil, surpassing
Malaysia in 2006, producing more than 20.9 million tonnes. Indonesia
aspires to become the world's top producer of palm oil.[43] But at the
end of 2010, 60 percent of the output was exported still in the form of
Crude Palm Oil.[44] FAO data show production increased by over Palm oil output in 2006

400% between 1994–2004, to over 8.66 million metric tonnes.

In addition to servicing traditional markets, Indonesia is looking to put more effort into producing biodiesel. Major
local and global companies are building mills and refineries, including PT. Astra Agro Lestari terbuka (150,000 tpa
biodiesel refinery), PT. Bakrie Group (a biodiesel factory and new plantations), Surya Dumai Group (biodiesel
refinery). Cargill (sometimes operating through CTP Holdings of Singapore, is building new refineries and mills in
Malaysia and Indonesia, expanding its Rotterdam refinery to handle 300,000 tpa of palm oil, acquiring plantations in
Sumatra, Kalimantan, the Indonesian peninsula and Papua New Guinea). Robert Kuok's Wilmar International
Limited has plantations and 25 refineries across Indonesia, to supply feedstock to new biodiesel refineries in
Singapore, Riau, Indonesia and Rotterdam.[38] In Kalimantan, the activity of palm oil companies endangers the
living space of Orang Utans. [45]

Malaysia
In 2008, Malaysia produced 17.7 million tonnes of palm oil on unknown operator: u',' hectares (unknown
operator: u'strong'unknown operator: u','sq mi) of land,[42] and was the second largest producer of palm oil,
employing more than 570,000 people.[46] Malaysia is the world's second largest exporter of palm oil. About 60% of
palm oil exports from Malaysia are shipped to China, the European Union, Pakistan, United States and India. They
are mostly made into cooking oil, margarine, specialty fats and oleochemicals.
In December 2006, the Malaysian government initiated merger of Sime Darby Berhad, Golden Hope Plantations
Berhad and Kumpulan Guthrie Berhad to create the world’s largest listed oil palm plantation player.[47] In a
landmark deal valued at RM31 billion, the merger involved the businesses of eight listed companies controlled by
Permodalan Nasional Berhad (PNB) and the Employees Provident Fund (EPF). A special purpose vehicle, Synergy
Drive Sdn Bhd, offered to acquire all the businesses including assets and liabilities of the eight listed companies.
With 543,000 hectares of plantation in a landbank, the merger resulted in an oil palm plantation entity that could
produce 2.5 million tonnes of palm oil or 5% of global production in 2006. A year later, the merger completed and
the entity was renamed Sime Darby Berhad.[48]
Palm oil 64

Nigeria
As of 2011, Nigeria was the third-largest producer, with more than 2.5 million hectares (unknown operator:
u'strong'×106 acres) under cultivation. Until 1934, Nigeria had been the world's largest producer. Both small- and
large-scale producers participated in the industry.[49][50]

Colombia
In the 1960s, about unknown operator: u',' hectares (unknown operator: u'strong'unknown operator: u','sq mi)
were planted with palm. Colombia has now become the largest palm oil producer in the Americas, and 35% of its
product is exported as biofuel. In 2006, the Colombian plantation owners' association, Fedepalma, reported that oil
palm cultivation was expanding to unknown operator: u',' hectares (unknown operator: u'strong'unknown
operator: u','sq mi). This expansion is being funded, in part, by the United States Agency for International
Development to resettle disarmed paramilitary members on arable land, and by the Colombian government, which
proposes to expand land use for exportable cash crops to unknown operator: u',' hectares (unknown operator:
u'strong'unknown operator: u','sq mi) by 2020, including oil palms. Fedepalma states that its members are
following sustainable guidelines.[51]
Some Afro-Colombians claim that some of these new plantations have been expropriated from them after they had
been driven away through poverty and civil war, while armed guards intimidate the remaining people to further
depopulate the land, while coca production and trafficking follows in their wake.[52]

Other producers

Benin
Palm is native to the wetlands of western Africa, and south Benin already hosts many palm plantations. Its
'Agricultural Revival Programme' has identified many thousands of hectares of land as suitable for new oil palm
export plantations. In spite of the economic benefits, Non-governmental organisations (NGOs), such as Nature
Tropicale, claim biofuels will compete with domestic food production in some existing prime agricultural sites.
Other areas comprise peat land, whose drainage would have a deleterious environmental impact. They are also
concerned genetically modified plants will be introduced for the first time into the region, jeopardizing the current
premium paid for their non-GM crops.[53]

Kenya
Kenya's domestic production of edible oils covers about a third of its annual demand, estimated at around 380,000
metric tonnes. The rest is imported at a cost of around US$140 million a year, making edible oil the country's second
most important import after petroleum. Since 1993 a new hybrid variety of cold-tolerant, high-yielding oil palm has
been promoted by the Food and Agriculture Organization of the United Nations in western Kenya. As well as
alleviating the country's deficit of edible oils while providing an important cash crop, it is claimed to have
environmental benefits in the region, because it does not compete against food crops or native vegetation and it
provides stabilisation for the soil.[54]
Palm oil 65

Ghana
Ghana has a lot of palm nuts vegetation, which can become an important contributor to the agriculture of the Black
Star region. Although Ghana has multiple palm species, ranging from local palm nuts to other species locally called
agric, it is only marketed locally and to neighboring countries.

Impacts

Social
Palm oil producers have been accused of various human-rights violations, from low pay and poor working
conditions[55] to theft of land[56] and murder.[57] However, some social initiatives use palm oil profits to finance
poverty alleviation strategies. Examples include the financing of Magbenteh hospital in Makeni, Sierra Leone
through profits made from palm oil grown by small local farmers,[58] the Presbyterian Disaster Assistance's Food
Security Program, which draws on a women-run cooperative to grow palm oil, the profits of which are reinvested in
food security,[59] or the UN Food and Agriculture Organisation's hybrid oil palm project in Western Kenya, which
improves incomes and diets of local populations.[60]

Environmental
Palm oil production has been documented as a cause of substantial and often irreversible damage to the natural
environment.[61] Its impacts include: deforestation, habitat loss of critically endangered species such as the
Orangutan[62][63][64][65] and Sumatran Tiger,[66][67] and a significant increase in greenhouse gas emissions.[68] The
pollution is exacerbated because many rainforests in Indonesia and Malaysia[69] lie atop peat bogs that store great
quantities of carbon that are released when the forests are cut down and the bogs drained to make way for
plantations. Environmental groups such as Greenpeace claim that the deforestation caused by making way for oil
palm plantations is far more damaging for the climate than the benefits gained by switching to biofuel.[70][71]
The Roundtable on Sustainable Palm Oil (RSPO)is an organisation that was formed in 2004 with the objective
promoting the growth and use of sustainable oil palm products through credible global standards and engagement of
stakeholders. It has over 450 member organisations that are from the different stakeholders in the palm oil supply
chain from the Palm Oil Growers to the Palm Oil Processors and Traders, Banks and Investors, Consumer Goods
Manufactures, Retailers, Environmental Organisations (NGOs) and Social Organisations (NGOs). RSPO practices a
consensus based decision making philosophy.[72] The seat of the association is in Zurich, Switzerland, while the
secretariat is currently based in Kuala Lumpur with a satellite office in Jakarta.[73] This video done by WWF a
environmental NGO gives a balance view of the industry and RSPO.[74] Many of the major companies in the
vegetable oil economy participate in the Roundtable on Sustainable Palm Oil, which is trying to address this
problem, though their efforts so far have done almost nothing to change or slow the escalating situation and have
been likened to green-washing.[75] Even so, in 2008 Unilever, a member of the RSPO group, committed to use only
palm oil which is certified as sustainable, by ensuring that the large companies and smallholders that supply it
convert to sustainable production by 2015.[76] On 1 June 2011, RSPO launched its trademark for use by its members.
With this trademark producers of products such as chocolate, margarine and cosmetics can show their commitment
towards sustainable palm oil through the use of the trademark.[77] On 1 July 2011, PT Carrefour Indonesia reiterated
its commitment to exclusively source for sustainable palm oil products by 2015.[78] In August of that same year,
RSPO marked one million hectares of certified sustainable land (and brought the volume of sustainable oil to over 5
million tonnes) with the certification of the Agropalma company in Brazil. It was also the first RSPO certification
received by Brazil.[79]
Meanwhile, much of the recent investment in new palm plantations for biofuel has been part-funded through carbon
credit projects through the Clean Development Mechanism; however the reputational risk associated with
unsustainable palm plantations in Indonesia has now made many funds wary of investing there.[80]
Palm oil 66

Medical
Although palm oil is applied to wounds for its supposed antimicrobial effects, research does not confirm its
effectiveness. scientists are testing it to see if it can cure cancer.[81]

Health

Blood lipid and cholesterol effects

The Center for Science in the Public Interest cites meta-analysis that point to excessive intake of palmitic acid (the
major saturated fatty acid in palm oil, which is also present in other food sources) as a culprit in heart disease.[82]
The CSPI report cited research that goes back to 1970[83] and metastudies.[84][85] CSPI also said that The National
Heart, Lung and Blood Institute,[86] World Health Organization (WHO), and other health authorities have urged
reduced consumption of palm oil. WHO states that there is convincing evidence that palmitic acid consumption
contributes to an increased risk of developing cardiovascular diseases.[87] 2005 research in Costa Rica suggests
consumption of non-hydrogenated unsaturated oils over palm oil.[88]
In 1993, Malaysia's Institute for Medical Research's head of Cardiovascular Disease Unit Cardiovascular, Diabetes
and Nutrition Centre Dr Tony Ng Kock Wai[89] showed that the cholesterol impact of saturated fats is affected by its
amount at the sn-2 position. Despite the high palmitic acid content (41%) of palm oil, only 13-14% is present at the
sn-2 position.[90]
In an email response to WHO's 2002 draft report, Dr. David Kritchevsky of the Wistar Institute, Philadelphia denied
that there were, at that time, any data showing palm oil consumption causing atherosclerosis.[91]
However, a 2006 study supported by the National Institutes of Health and the USDA Agricultural Research Service
concluded that palm oil is not a safe substitute for partially hydrogenated fats (trans fats) in the food industry,
because palm oil results in adverse changes in the blood concentrations of LDL cholesterol and apolipoprotein B just
as trans fat does.[92][93]

Comparison with animal saturated fat

Not all saturated fats are equally cholesterolemic.[94] Studies have indicated that consumption of palm olein (which
is more unsaturated) reduces blood cholesterol when compared to sources of saturated fats like coconut oil, dairy and
animal fats.[95]
In 1996, Dr Becker of University of Massachusetts stressed that saturated fats in the sn–1 and -3 position of
triacylglycerols exhibit different metabolic patterns because of their low absorptivity. Dietary fats containing
saturated fats primarily in sn–1 and -3 positions (e.g., cocoa butter, coconut oil, and palm oil) have very different
biological consequences than those fats in which the saturated fats are primarily in the sn–2 position (e.g., milk fat
and lard). Differences in stereospecific fatty acid location should be an important consideration in the design and
interpretation of lipid nutrition studies and in the production of specialty food products.[96]
Palm oil 67

Roundtable on Sustainable Palm Oil

The Roundtable on Sustainable Palm Oil (RSPO) was formed in 2004
with the objective of promoting the growth and use of sustainable oil
palm products through credible global standards and engagement of
stakeholders. The seat of the association is in Zurich, Switzerland,
while the secretariat is currently based in Kuala Lumpur with a satellite
office in Jakarta.
RSPO is a not-for-profit association that represents stakeholders from
seven sectors of the palm oil industry - oil palm producers, palm oil
processors or traders, consumer goods manufacturers, retailers, banks Roundtable No 2 (RT2) in Zurich in 2005.
and investors, environmental or nature conservation NGOs and social
or developmental NGOs - to develop and implement global standards for sustainable palm oil.
Such multi-stakeholder representation is mirrored in the governance structure of RSPO such that seats in the
Executive Board and project level Working Groups are fairly allocated to each sector. In this way, RSPO lives out
the philosophy of the "roundtable" by giving equal rights to each stakeholder group to bring group-specific agendas
to the roundtable, facilitating traditionally adversarial stakeholders and business competitors to work together
towards a common objective and making decisions by consensus
The organization holds an annual meeting called RT or Round Table Meetings to bring together the various
stakeholders to negotiate and deliberate on various issues affecting the industry. Such multi-stakeholder
representation is mirrored in the governance structure of RSPO such that seats in the Executive Board and project
level Working Groups are fairly allocated to each sector.
Some of the key achievements of the organization so far include:
• Establishment of the RSPO Principles & Criteria (P&C) for certification of mills and plantations;
• Formation of Working Groups on Green House Gases to address climate change issues;
• Smallholder Task Force to protect the rights of small farmers planting oil palm; and
• Biodiversity Technical Committee to work out biodiversity issues pertaining to sustainable production and
biodiversity protection and conservation.[97]

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Palm oil 70

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htm#Cholesterolaemic effects of the saturated fatly acids of palm oil) Pramod Khosla and K. C. Hayes, The United Nations University Press,
Food and Nutrition Bulletin, Volume 15 (1993/1994), Number 2, June 1994
[91] Kritchevsky, David (6 June 2002). "Wistar Institute comments on WHO/FAO Diet, Nutrition and Prevention of Chronic Disease draft
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[92] Vega-López, Sonia et al. (July 2006). "Palm and partially hydrogenated soybean oils adversely alter lipoprotein profiles compared with
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Palm oil 71

External links
• Palm Oil - Production, Consumption, Exports, and Imports Statistics by Country ([Link]
en/commodities/agricultural/oil-palm/)
• Blood on the Palms: Afro-Colombians fight new plantations ([Link]
[Link]) by David Bacon, July/August 2007 Dollars & Sense
• Palm Oil as a Fuel for Agricultural Diesel Engines: Comparative Testing against Diesel Oil ([Link]
[Link]/biodiesel_SVO-[Link])

Transesterification
In organic chemistry, transesterification is the process of exchanging the organic group R″ of an ester with the
organic group R′ of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The
reaction can also be accomplished with the help of enzymes (biocatalysts) particularly lipases (E.C.[Link]).

Transesterification: alcohol + ester → different alcohol + different ester

Strong acids catalyse the reaction by donating a proton to the carbonyl group, thus making it a more potent
electrophile, whereas bases catalyse the reaction by removing a proton from the alcohol, thus making it more
nucleophilic. Esters with larger alkoxy groups can be made from methyl or ethyl esters in high purity by heating the
mixture of ester, acid/base, and large alcohol and evaporating the small alcohol to drive equilibrium.

Applications

Polyester production
The largest scale application of transesterification is in the synthesis of polyesters.[1] In this application diesters
undergo transesterification with diols to form macromolecules. For example, dimethyl terephthalate and ethylene
glycol react to form polyethylene terephthalate and methanol, which is evaporated to drive the reaction forward.

Methanolysis and biodiesel production

The reverse reaction, methanolysis, is also an example of transesterification. This process has been used to recycle
polyesters into individual monomers (see plastic recycling). It is also used to convert fats (triglycerides) into
biodiesel. This conversion was one of the first uses. Transesterified vegetable oil (biodiesel) was used to power
heavy-duty vehicles in South Africa before World War II.
It was patented in the U.S. in the 1950s by Colgate, though Biolipid transesterification may have been discovered
much earlier. In the 1940s, researchers were looking for a method to more readily produce glycerine, which was used
to produce explosives for World War II. Many of the methods used today by producers and homebrewers have their
origin in the original 1940s research.
Biolipid transesterification has also been recently shown by Japanese researchers to be possible using a super-critical
methanol methodology, whereby high temperature, high-pressure vessels are used to physically catalyze the
Transesterification 72

Biolipid/methanol reaction into fatty-acid methyl esters.

References
[1] Wilhelm Riemenschneider1 and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH,
Weinheim. doi:10.1002/14356007.a09_565.pub2
Hydrogenation 73

Hydrogenation
Catalysed hydrogenation
Process type Chemical

Industrial sector(s) Food industry, petrochemical industry, pharmaceutical industry, agricultural industry

Main technologies or sub-processes Various transition metal catalysts, high-pressure technology

Feedstock Unsaturated substrates and hydrogen or hydrogen donors

Product(s) Saturated hydrocarbons and derivatives

Inventor Paul Sabatier

Year of invention 1897

Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular
hydrogen (H2) and another compound or element, usually in the presence of a catalyst. The process is commonly
employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of
hydrogen atoms to a molecule, generally an alkene. Catalysts are required for the reaction to be usable; non-catalytic
hydrogenation takes place only at very high temperatures. Hydrogen adds to double and triple bonds in
hydrocarbons.[1]
Because of the importance of hydrogen, many related reactions have been developed for its use. Most
hydrogenations use gaseous hydrogen (H2), but some involve the alternative sources of hydrogen, not H2: these
processes are called transfer hydrogenations. The reverse reaction, removal of hydrogen from a molecule, is called
dehydrogenation. A reaction where bonds are broken while hydrogen is added is called hydrogenolysis, a reaction
that may occur to carbon-carbon and carbon-heteroatom (oxygen, nitrogen or halogen) bonds. Hydrogenation differs
from protonation or hydride addition: in hydrogenation, the products have the same charge as the reactants.
An illustrative example of a hydrogenation reaction is the addition of hydrogen to maleic acid to form succinic
acid.[2] Numerous important applications of this petrochemical are found in pharmaceutical and food industries.
Hydrogenation of unsaturated fats produces saturated fats and, in some cases, trans fats.

Process
Hydrogenation has three components,
the unsaturated substrate, the hydrogen
(or hydrogen source) and, invariably, a
catalyst. The reaction is carried out at
different temperatures and pressures
depending upon the substrate and the activity of the catalyst.
Hydrogenation 74

Substrate
The addition of H2 to an alkene affords an alkane in the protypical reaction:
RCH=CH2 + H2 → RCH2CH3 (R = alkyl, aryl)
Hydrogenation is sensitive to steric hindrance explaining the selectivity for reaction with the exocyclic double bond
but not the internal double bond.
An important characteristic of alkene and alkyne hydrogenations, both the homogeneously and heterogeneously
catalyzed versions, is that hydrogen addition occurs with "syn addition", with hydrogen entering from the least
hindered side.[3] Typical substrates are listed in the table

Substrates for and products of hydrogenation

alkene, R2C=CR'2 alkane, R2CHCHR'2

alkyne, RCCR alkene, cis-RHC=CHR'

aldehyde, RCHO primary alcohol, RCH2OH

ketone, R2CO secondary alcohol, R2CHOH

ester, RCO2R' two alcohols, RCH2OH, R'OH

imine, RR'CNR" amine, RR'CHNHR"

amide, RC(O)NR'2 amine, RCH2NR'2

nitrile, RCN imine, RHCNH easily hydrogenated further

nitro, RNO2 amine, RNH2

Catalysts
With rare exceptions, no reaction below 480 °C (750 K or 900 °F) occurs between H2 and organic compounds in the
absence of metal catalysts. The catalyst binds both the H2 and the unsaturated substrate and facilitates their union.
platinum, palladium, rhodium, and ruthenium form highly active catalysts, which operate at lower temperatures and
lower pressures of H . Non-precious metal catalysts, especially those based on nickel (such as Raney nickel and
2
Urushibara nickel) have also been developed as economical alternatives, but they are often slower or require higher
temperatures. The trade-off is activity (speed of reaction) vs. cost of the catalyst and cost of the apparatus required
for use of high pressures. Notice that the Raney-nickel catalysed hydrogenations require high pressures:[4][5]
Two broad families of catalysts are
known - homogeneous catalysts and
heterogeneous catalysts. Homogeneous
catalysts dissolve in the solvent that
contains the unsaturated substrate.
Heterogeneous catalysts are solids that
are suspended in the same solvent with
the substrate or are treated with
gaseous substrate.

Homogeneous catalysts

Illustrative homogeneous catalysts

include the rhodium-based compound
known as Wilkinson's catalyst and the
iridium-based Crabtree's catalyst. An example is the hydrogenation of carvone:[6]
Hydrogenation 75

Hydrogenation is sensitive to steric

hindrance explaining the selectivity for
reaction with the exocyclic double bond but
not the internal double bond.
The activity and selectivity of homogeneous
catalysts is adjusted by changing the
ligands. For prochiral substrates, the
selectivity of the catalyst can be adjusted
such that one enantiomeric product is favored. Asymmetric hydrogenation is also possible via heterogeneous
catalysis on a metal that is modified by a chiral ligand.[7]

Heterogeneous catalysts
Heterogeneous catalysts for hydrogenation are more common industrially. As in homogeneous catalysts, the activity
is adjusted through changes in the environment around the metal, i.e. the coordination sphere. Different faces of a
crystalline heterogeneous catalyst display distinct activities, for example. Similarly, heterogeneous catalysts are
affected by their supports, i.e. the material upon with the heterogeneous catalyst is bound.
In many cases, highly empirical modifications involve selective "poisons". Thus, a carefully chosen catalyst can be
used to hydrogenate some functional groups without affecting others, such as the hydrogenation of alkenes without
touching aromatic rings, or the selective hydrogenation of alkynes to alkenes using Lindlar's catalyst. For example,
when the catalyst palladium is placed on barium sulfate and then treated with quinoline, the resulting catalyst
reduces alkynes only as far as alkenes. The Lindlar catalyst has been applied to the conversion of phenylacetylene to
styrene.[8]
Asymmetric hydrogenation is also
possible via heterogeneous catalysis on
a metal that is modified by a chiral
ligand.[7]

Hydrogen sources
For hydrogenation, the obvious source of hydrogen is H2 gas itself, which is typically available commercially within
the storage medium of a pressurized cylinder. The hydrogenation process often uses greater than 1 atmosphere of H2,
usually conveyed from the cylinders and sometimes augmented by "booster pumps". Gaseous hydrogen is produced
industrially from hydrocarbons by the process known as steam reforming.[9]

Transfer hydrogenation
Hydrogen also can be extracted ("transferred") from "hydrogen-donors" in place of H2 gas. Hydrogen donors, which
often serve as solvents include hydrazine, dihydronaphthalene, dihydroanthracene, isopropanol, and formic acid.[10]
In organic synthesis, transfer hydrogenation is useful for the asymmetric reduction of polar unsaturated substrates,
such as ketones, aldehydes, and imines.

Electrolytic hydrogenation
Polar substrates such as ketones can be hydrogenated electrochemically, using protic solvents and reducing
equivalents as the source of hydrogen.[11]
Hydrogenation 76

Thermodynamics and mechanism

Hydrogenation is a strongly exothermic reaction. In the hydrogenation of vegetable oils and fatty acids, for example,
the heat released is about 25 kcal per mole (105 kJ/mol), sufficient to raise the temperature of the oil by 1.6-1.7 °C
per iodine number drop. The mechanism of metal-catalyzed hydrogenation of alkenes and alkynes has been
extensively studied.[12] First of all isotope labeling using deuterium confirms the regiochemistry of the addition:
RCH=CH2 + D2 → RCHDCH2D

Heterogeneous catalysis
On solids, the accepted mechanism today is called the Horiuti-Polanyi mechanism.
1. Binding of the unsaturated bond, and hydrogen dissociation into atomic hydrogen onto the catalyst
2. Addition of one atom of hydrogen; this step is reversible
3. Addition of the second atom; effectively irreversible under hydrogenating conditions.
In the second step, the metallointermediate formed is a saturated compound that can rotate and then break down,
again detaching the alkene from the catalyst. Consequently, contact with a hydrogenation catalyst necessarily causes
cis-trans-isomerization. This is a problem in partial hydrogenation, while in complete hydrogenation the produced
trans-alkene is eventually hydrogenated.
For aromatic substrates, the first bond is hardest to hydrogenate because of the free energy penalty for breaking the
aromatic system. The product of this is a cyclohexadiene, which is extremely active and cannot be isolated; in
conditions reducing enough to break the aromatization, it is immediately reduced to a cyclohexene. The cyclohexene
is ordinarily reduced immediately to a fully saturated cyclohexane, but special modifications to the catalysts (such as
the use of the anti-solvent water on ruthenium) can preserve some of the cyclohexene, if that is a desired product.

Homogeneous catalysis
In many homogeneous hydrogenation processes,[13] the metal binds to both components to give an intermediate
alkene-metal(H)2 complex. The general sequence of reactions is assumed to be as follows or a related sequence of
steps:
• binding of the hydrogen to give a dihydride complex ("oxidative addition"):
LnM + H2 → LnMH2
• binding of alkene:
LnM(η2H2) + CH2=CHR → Ln-1MH2(CH2=CHR) + L
• transfer of one hydrogen atom from the metal to carbon (migratory insertion)
Ln-1MH2(CH2=CHR) → Ln-1M(H)(CH2-CH2R)
• transfer of the second hydrogen atom from the metal to the alkyl group with simultaneous dissociation of the
alkane ("reductive elimination")
Ln-1M(H)(CH2-CH2R) → Ln-1M + CH3-CH2R
Preceding the oxidative addition of H2 is the formation of a dihydrogen complex.
Hydrogenation 77

Inorganic substrates
The hydrogenation of nitrogen to give ammonia is conducted on a vast scale by the Haber-Bosch process, consuming
an estimated 1% of the world's energy supply.
Oxygen can be partially hydrogenated to give hydrogen peroxide,
although this process has not been commercialized.

Industrial applications
Catalytic hydrogenation has diverse industrial uses.
In petrochemical processes, hydrogenation is used to convert alkenes and aromatics into saturated alkanes (paraffins)
and cycloalkanes (naphthenes), which are less toxic and less reactive. For example, mineral turpentine is usually
hydrogenated. Hydrocracking of heavy residues into diesel is another application. In isomerization and catalytic
reforming processes, some hydrogen pressure is maintained to hydrogenolyze coke formed on the catalyst and
prevent its accumulation.
Xylitol, a polyol, is produced by hydrogenation of the sugar xylose, an aldehyde.

In the food industry

Hydrogenation is widely applied to the processing of vegetable oils fats. Complete hydrogenation converts
unsaturated fatty acids to saturated ones. In practice the process is not usually carried to completion. Since the
original oils usually contain more than one carbon-carbon double bond per molecule (that is, they are
polyunsaturated), the result is usually described as partially hydrogenated vegetable oil; that is some, but usually not
all, of the carbon-carbon double bonds in each molecule have been reduced. This is done by restricting the amount of
hydrogen (or reducing agent) allowed to react with the fat.
Hydrogenation results in the conversion of liquid vegetable oils to solid or semi-solid fats, such as those present in
margarine. Changing the degree of saturation of the fat changes some important physical properties such as the
melting range, which is why liquid oils become semi-solid. Solid or semi-solid fats are preferred for baking because
the way the fat mixes with flour produces a more desirable texture in the baked product. Because partially
hydrogenated vegetable oils are cheaper than animal source fats, are available in a wide range of consistencies, and
have other desirable characteristics (e.g., increased oxidative stability/longer shelf life), they are the predominant fats
used as shortening in most commercial baked goods.

Health implications
A side effect of incomplete hydrogenation having implications for human health is the isomerization of some of the
remaining unsaturated carbon bonds. The cis configuration of these double bonds predominates in the unprocessed
fats in most edible fat sources, but incomplete hydrogenation partially converts these molecules to trans isomers,
which have been implicated in circulatory diseases including heart disease (see trans fats). The conversion from cis
to trans bonds is favored because the trans configuration has lower energy than the natural cis one. At equilibrium,
the trans/cis isomer ratio is about 2:1. Food legislation in the US and codes of practice in EU have long required
labels declaring the fat content of foods in retail trade and, more recently, have also required declaration of the trans
fat content. Trans fats are banned in Denmark and New York City.[14][15]
Hydrogenation 78

History
The earliest hydrogenation is that of platinum catalyzed addition of hydrogen to oxygen in the Döbereiner's lamp, a
device commercialized as early as 1823. The French chemist Paul Sabatier is considered the father of the
hydrogenation process. In 1897, building on the earlier work of James Boyce, an American chemist working in the
manufacture of soap products, he discovered that the introduction of a trace of nickel as a catalyst facilitated the
addition of hydrogen to molecules of gaseous hydrocarbons in what is now known as the Sabatier process. For this
work Sabatier shared the 1912 Nobel Prize in Chemistry. Wilhelm Normann was awarded a patent in Germany in
1902 and in Britain in 1903 for the hydrogenation of liquid oils, which was the beginning of what is now a world
wide industry. The commercially important Haber-Bosch process, first described in 1905, involves hydrogenation of
nitrogen. In the Fischer-Tropsch process, reported in 1922 carbon monoxide, which is easily derived from coal, is
hydrogenated to liquid fuels.
Also in 1922, Voorhees and Adams described an apparatus for performing hydrogenation under pressures above one
atmosphere.[16] The Parr shaker, the first product to allow hydrogenation using elevated pressures and temperatures,
was commercialized in 1926 based on Voorhees and Adams’ research and remains in widespread use. In 1924
Murray Raney developed a nickel fine powder catalyst named after him which is still widely used in hydrogenation
reactions such as conversion of nitriles to amines or the production of margarine. In 1938, Otto Roelen described the
oxo process which involves the addition of both hydrogen and carbon monoxide to alkenes, giving aldehydes. Since
this process entails C-C coupling, it and its many variations (see carbonylation) remains highly topical into the new
decade.[17] The 1960s witnessed the development of homogeneous catalysts, e.g., Wilkinson's catalyst. In the 1980s,
the Noyori asymmetric hydrogenation represented one of the first applications of hydrogenation in asymmetric
synthesis, a growing application in the production of fine chemicals.

Metal-free hydrogenation
For all practical purposes, hydrogenation requires a metal catalyst. Hydrogenation can, however, proceed from some
hydrogen donors without catalysts, illustrative hydrogen donors being diimide and aluminium isopropoxide. Some
metal-free catalytic systems have been investigated in academic research. One such system for reduction of ketones
consists of tert-butanol and potassium tert-butoxide and very high temperatures.[18] The reaction depicted below
describes the hydrogenation of benzophenone:

A chemical kinetics study[19] found this reaction is first-order in all three reactants suggesting a cyclic 6-membered
transition state.
Another system for metal-free hydrogenation is based on the phosphine-borane, compound 1, which has been called
a frustrated Lewis pair. It reversibly accepts dihydrogen at relatively low temperatures to form the phosphonium
borate 2 which can reduce simple hindered imines.[20]
Hydrogenation 79

The reduction of nitrobenzene to aniline has been reported to be catalysed by fullerene, its mono-anion, atmospheric
hydrogen and UV light.[21]

Equipment used for hydrogenation

Today’s bench chemist has three main choices of hydrogenation equipment:
• Batch hydrogenation under atmospheric conditions
• Batch hydrogenation at elevated temperature and/or pressure
• Flow hydrogenation

Batch hydrogenation under atmospheric conditions

The original and still a commonly practised form of hydrogenation in teaching laboratories, this process is usually
effected by adding solid catalyst to a round bottom flask of dissolved reactant which has been evacuated using
nitrogen or argon gas and sealing the mixture with a penetrable rubber seal. Hydrogen gas is then supplied from a
H2-filled balloon. The resulting three phase mixture is agitated to promote mixing. Hydrogen uptake can be
monitored, which can be useful for monitoring progress of a hydrogenation. This is achieved by either using a
graduated tube containing a coloured liquid, usually aqueous copper sulfate or with gauges for each reaction vessel.

Batch hydrogenation at elevated temperature and/or pressure

Since many hydrogenation reactions such as hydrogenolysis of protecting groups and the reduction of aromatic
systems proceed extremely sluggishly at atmospheric temperature and pressure, pressurised systems are popular. In
these cases, catalyst is added to a solution of reactant under an inert atmosphere in a pressure vessel. Hydrogen is
added directly from a cylinder or built in laboratory hydrogen source, and the pressurized slurry is mechanically
rocked to provide agitation or a spinning basket is used. Heat may also be used, as the pressure compensates for the
associated reduction in gas solubility.

Flow hydrogenation
Flow hydrogenation has become a popular technique at the bench and increasingly the process scale. This technique
involves continuously flowing a dilute stream of dissolved reactant over a fixed bed catalyst in the presence of
hydrogen. Using established HPLC technology, this technique allows the application of pressures from atmospheric
to 1,450 PSI. Elevated temperatures may also be used. At the bench scale, systems use a range of pre-packed
catalysts which eliminates the need for weighing and filtering pyrophoric catalysts.
Hydrogenation 80

Industrial reactors
Catalytic hydrogenation is done in a tubular plug-flow reactor (PFR) packed with a supported catalyst. The pressures
and temperatures are typically high, although this depends on the catalyst. Catalyst loading is typically much lower
than in laboratory batch hydrogenation, and various promoters are added to the metal, or mixed metals are used, to
improve activity, selectivity and catalyst stability. The use of nickel is common despite its low activity, due to its low
cost compared to precious metals.
Gas Liquid Induction Reactors (Hydrogenator) are also used for carrying out catalytic hydrogenation.[22]

References
[1] Hudlický, Miloš (1996). Reductions in Organic Chemistry. Washington, D.C.: American Chemical Society. pp. 429. ISBN 0-8412-3344-6.
[2] Catalytic Hydrogenation of Maleic Acid at Moderate Pressures A Laboratory Demonstration Kwesi Amoa 1948 Journal of Chemical
Education • Vol. 84 No. 12 December 2007
[3] Advanced Organic Chemistry Jerry March 2nd Edition
[4] C. F. H. Allen and James VanAllan (1955), "m-Toylybenzylamine" (http:/ / www. orgsyn. org/ orgsyn/ orgsyn/ prepContent.
asp?prep=CV3P0827), Org. Synth., ; Coll. Vol. 3: 827
[5] A. B. Mekler, S. Ramachandran, S. Swaminathan, and Melvin S. Newman (1973), "2-Methyl-1,3-Cyclohexanedione" (http:/ / www. orgsyn.
org/ orgsyn/ orgsyn/ prepContent. asp?prep=CV5P0567), Org. Synth., ; Coll. Vol. 5: 743
[6] S. Robert E. Ireland and P. Bey (1988), "Homogeneous Catalytic Hydrogenation: Dihydrocarvone" (http:/ / www. orgsyn. org/ orgsyn/
orgsyn/ prepContent. asp?prep=CV6P0459), Org. Synth., ; Coll. Vol. 6: 459
[7] T. Mallet, E. Orglmeister, A. Baiker" Chemical Reviews, 2007, 107, 4863-4890. doi:10.1021/cr0683663
[8] H. Lindlar and R. Dubuis (1973), "Palladium Catalyst for Partial Reduction of Acetylenes" (http:/ / www. orgsyn. org/ orgsyn/ orgsyn/
prepContent. asp?prep=CV5P0880), Org. Synth., ; Coll. Vol. 5: 880
[9] Paul N. Rylander, "Hydrogenation and Dehydrogenation" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
[10] van Es, T.; Staskun, B. "Aldehydes from Aromatic Nitriles: 4-Formylbenzenesulfonamide" Org. Syn., Coll. Vol. 6, p.631 (1988). ( Article
(http:/ / www. orgsyn. org/ orgsyn/ prep. asp?prep=cv6p0631))
[11] Daniela Maria do Amaral Ferraz Navarro and Marcelo Navarro "Catalytic Hydrogenation of Organic Compounds without H2 Supply: An
Electrochemical System" J. Chem. Educ., 2004, vol. 81, p 1350. doi:10.1021/ed081p1350
[12] Kubas, G. J., "Metal Dihydrogen and σ-Bond Complexes", Kluwer Academic/Plenum Publishers: New York, 2001
[13] Johannes G. de Vries, Cornelis J. Elsevier, eds. The Handbook of Homogeneous Hydrogenation Wiley-VCH, Weinheim, 2007. ISBN
978-3-527-31161-3
[14] "Deadly fats: why are we still eating them?" (http:/ / www. independent. co. uk/ life-style/ health-and-wellbeing/ healthy-living/
deadly-fats-why-are-we-still-eating-them-843400. html). The Independent. 2008-06-10. . Retrieved 2008-06-16.
[15] "New York City passes trans fat ban" (http:/ / www. msnbc. msn. com/ id/ 16051436/ ). msnbc. 2006-12-05. . Retrieved 2010-01-09.
[16] http:/ / pubs. acs. org/ cgi-bin/ abstract. cgi/ jacsat/ 1922/ 44/ i06/ f-pdf/ f_ja01427a021. pdf
[17] Perspective: Hydrogen-Mediated C-C Bond Formation: A Broad New Concept in Catalytic C-C Coupling Ming-Yu Ngai, Jong-Rock Kong,
and Michael J. Krische J. Org. Chem.; 2007, 72, pp. 1063–1072. doi:10.1021/jo061895m
[18] Homogeneous Hydrogenation in the Absence of Transition-Metal Catalysts Cheves Walling, Laszlo Bollyky J. Am. Chem. Soc.; 1964;
86(18); 3750–3752. doi:10.1021/ja01072a028
[19] Hydrogenation without a Transition-Metal Catalyst: On the Mechanism of the Base-Catalyzed Hydrogenation of Ketones Albrecht
Berkessel, Thomas J. S. Schubert, and Thomas N. Muller J. Am. Chem. Soc. 2002, 124, 8693–8698 doi:10.1021/ja016152r
[20] Metal-Free Catalytic Hydrogenation Preston A. Chase, Gregory C. Welch, Titel Jurca, and Douglas W. Stephan Angew. Chem. Int. Ed.
2007, 46, 8050–8053. doi:10.1002/anie.200702908
[21] A Nonmetal Catalyst for Molecular Hydrogen Activation with Comparable Catalytic Hydrogenation Capability to Noble Metal Catalyst
Baojun Li and Zheng Xu J. Am. Chem. Soc., 2009, 131 (45), pp 16380–16382. doi:10.1021/ja9061097
[22] Mechanically agitated gas-liquid reactors J.B. Joshi, A.B. Pandit, M.M. Sharma Department of Chemical Technology, University of
Bombay, Matunga, Bombay-400019, India http:/ / www. sciencedirect. com/ science/ article/ pii/ 0009250982801711
Hydrogenation 81

Further reading
• Jang ES, Jung MY, Min DB (2005). "Hydrogenation for Low Trans and High Conjugated Fatty Acids" (http://
[Link]/NR/rdonlyres/27B49B9B-EA63-4D73-BAB4-42FEFCD72C68/0/
[Link]) (PDF). Comprehensive Reviews in Food Science and Food Safety 1.
• examples of hydrogenation from Organic Syntheses:
• Organic Syntheses, Coll. Vol. 7, p.226 (1990). ([Link]
• Organic Syntheses, Coll. Vol. 8, p.609 (1993). ([Link]
• Organic Syntheses, Coll. Vol. 5, p.552 (1973). ([Link]
• Organic Syntheses, Coll. Vol. 3, p.720 (1955). ([Link]
• Organic Syntheses, Coll. Vol. 6, p.371 (1988). ([Link]
• early work on transfer hydrogenation: Davies, R. R.; Hodgson, H. H. J. Chem. Soc. 1943, 281. Leggether, B. E.;
Brown, R. K. Can. J. Chem. 1960, 38, 2363. Kuhn, L. P. J. Am. Chem. Soc. 1951, 73, 1510.
• Fred A. Kummerow (2008). Cholesterol Won't Kill You, But Trans Fat Could. Trafford. ISBN 142513808.

External links
• "The Magic of Hydro" Popular Mechanics, June 1931, pp. 107-109 ([Link]
books?id=4OIDAAAAMBAJ&pg=-PA107&dq=Popular+Science+1930+plane+"Popular+Mechanics"&
hl=en&ei=NCt4TtDKIqnf0QG65_3-Cw&sa=X&oi=book_result&ct=book-thumbnail&resnum=6&
ved=0CEIQ6wEwBTge#v=onepage&q&f=true) early article for the general public on hydrogenation of oil
produces in the 1930s

Saponification
Saponification is a process that
produces soap, usually from fats and
lye. In technical terms, saponification
involves base (usually caustic soda
NaOH) hydrolysis of triglycerides,
which are esters of fatty acids, to form
the sodium salt of a carboxylate. In
addition to soap, such traditional Saponification of a triglyceride with sodium hydroxide.
saponification processes produces
glycerol. "Saponifiable substances" are those that can be converted into soap.[1]

Saponification of triglyceride
Vegetable oils and animal fats are the main materials that are saponified. These greasy materials, triesters called
triglycerides, are mixtures derived from diverse fatty acids. Triglycerides can be converted to soap in either a one- or
a two-step process. In the traditional one-step process, the triglyceride is treated with a strong base (e.g., lye), which
accelerates cleavage of the ester bond and releases the fatty acid salt and glycerol. This process is the main industrial
method for producing glycerol. If necessary, soaps may be precipitated by salting it out with saturated sodium
chloride. The saponification value is the amount of base required to saponify a fat sample. For soap making, the
triglycerides are highly purified, but saponification includes other base hydrolysis of unpurified triglycerides, for
example, the conversion of the fat of a corpse into adipocere, often called "grave wax." This process is more
common where the amount of fatty tissue is high, the agents of decomposition are absent or only minutely present,
Saponification 82

and the burial ground is particularly alkaline.

Mechanism of base hydrolysis

The mechanism by which esters are cleaved by base involves nucleophilic acyl substitution.[2] The hydroxide anion
adds to (or "attacks") the carbonyl group of the ester. The immediate product is an orthoester:

At this stage, the orthoester has a choice: Reforming the carbonyl can be accompanied by expulsion of either the
hydroxide or the alkoxide. The former leads back to the starting materials and is unproductive (explaining why
saponification is in fact an equilibrium). On the other hand, expulsion of the alkoxide generates a carboxylic acid:

The alkoxide is more basic than the conjugate base of the carboxylic acid, and hence proton transfer is rapid:

In a classic laboratory procedure, the triglyceride trimyristin is obtained by extracting it from nutmeg with diethyl
ether.[3] Saponification to the sodium salt of myristic acid takes place with NaOH in water. The acid itself can be
obtained by adding dilute hydrochloric acid.[4]

Steam hydrolysis
Triglycerides are also saponified in a two-step process that begins with steam hydrolysis of the triglyceride. This
process gives the carboxylic acid, not its salt, as well as glycerol. Subsequently, the fatty acid is neutralized with
alkali to give the soap. The advantage of the two-step process is that the fatty acids can be purified, which leads to
soaps of improved quality. Steam hydrolysis proceeds via a mechanism similar to the base-catalysed route, involving
the attack of water (not hydroxide) at the carbonyl center. The process is slower, hence the requirement for steam.
Saponification 83

Applications
Knowledge of saponification is relevant to many technologies and many aspects of everyday life.

Soft vs hard soap

Depending on the nature of the alkali used in their production, soaps have distinct properties. Sodium hydroxide
(NaOH) gives "hard soap", whereas, when potassium hydroxide (KOH) is used, a soft soap is formed.

Lithium soaps
Lithium derivatives of 12-hydroxystearate and several other carboxylic acids are important constituents of
lubricating greases. In lithium-based greases, lithium carboxylates are thickeners. "Complex soaps" are also
common, these being combinations of metallic soaps, such as lithium and calcium soaps.[5]

Fire extinguishers
Fires involving cooking fats and oils (classified as class K (US) or F (Australia/Europe/Asia)) burn hotter than
flammable liquids, rendering a standard class B extinguisher ineffective. Flammable liquids have flash points under
100 degrees Fahrenheit. Cooking oil is a combustible liquid, since it has a flash point over 100 degrees. Such fires
should be extinguished with a wet chemical extinguisher. Extinguishers of this type are designed to extinguish
cooking fats and oils through saponification. The extinguishing agent rapidly converts the burning substance to a
non-combustible soap. This process is endothermic, meaning that it absorbs thermal energy from its surroundings,
which decreases the temperature of the surroundings, further inhibiting the fire.

Saponification in art conservation

Saponification can occur in oil paintings over time, causing visible damage and deformation. The ground layer or
paint layers of oil paintings commonly contain heavy metals in pigments such as lead white, red lead, or zinc white.
If those heavy metals react with free fatty acids in the oil medium that binds the pigments together, soaps may form
in a paint layer that can then migrate upward to the painting's surface.[6]
Saponification in oil paintings was first described in 1997.[7] It is believed to be widespread, having been observed in
many works dating from the fifteenth through the twentieth centuries, works of different geographic origin, and
works painted on various supports, such as canvas, paper, wood, and copper. Chemical analysis may reveal
saponification occurring in a painting’s deeper layers before any signs are visible on the surface, even in paintings
centuries old.[8]
The saponified regions may deform the painting's surface through the formation of visible lumps or protrusions that
can scatter light. These soap lumps may be prominent only on certain regions of the painting rather than throughout.
In John Singer Sargent’s famous Portrait of Madame X, for example, the lumps only appear on the blackest areas,
which may be because of the artist’s use of more medium in those areas to compensate for the tendency of black
pigments to soak it up.[9] The process can also form chalky white deposits on a painting’s surface, a deformation
often described as "blooming" or "efflorescence," and may also contribute to the increased transparency of certain
paint layers within an oil painting over time.[10]
The process is still not fully understood. Saponification does not occur in all oil paintings containing the right
materials. It is not yet known what triggers the process, what makes it worse, or whether it can be halted.[11] At
present, retouching is the only known restoration method.
Saponification 84

References
[1] K. Schumann, K. Siekmann “Soaps” in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.
doi:10.1002/14356007.a24_247
[2] John McMurry, Organic Chemistry (2nd Edition).
[3] Organic Syntheses 1:538 Link (http:/ / orgsynth. org/ orgsyn/ pdfs/ CV1P0538. pdf)
[4] Organic Syntheses 1:379 Link (http:/ / orgsynth. org/ orgsyn/ pdfs/ CV1P0379. pdf)
[5] Thorsten Bartels et al. "Lubricants and Lubrication" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Weinheim.
doi:10.1002/14356007.a15 423
[6] Silvia A. Centeno and Dorothy Mahon, "The Chemistry of Aging in Oil Paintings: Metal Soaps and Visual Changes." The Metropolitan
Museum of Art Bulletin’’, Summer 2009, pp. 12-19.
[7] Researchers in the Netherlands discovered it while analyzing Rembrandt's The Anatomy Lesson of Dr. Nicolaes Tulp (1632). See Centeno, p.
14.
[8] Centeno, p. 16.
[9] Centeno, pp. 12-13, 15.
[10] Centeno, pp. 16, 19.
[11] Centeno, p. 19.

External links
• Soapmaking at Bellaonline ([Link] - Soapmaking articles, forum and
supplier links.
• Soap Naturally Web and Mailing List ([Link] - Resources for natural handmade
soapmakers.
• Soap Recipe Corner ([Link] - Soapmaking explained.
• About Candle and Soap Making ([Link] - Soap making at [Link]
• Glossary for the Modern Soap Maker ([Link] - A collection of terms,
definitions and acronyms for today's soap maker.
• The Handbook of Soap Manufacture ([Link] - A book from 1908.
Article Sources and Contributors 85

Article Sources and Contributors

Oleochemistry  Source: [Link]  Contributors: Leftfoot69, Michel Awkal, Sscrofa, V8rik

Oleochemical  Source: [Link]  Contributors: Albmont, Arunnguptaa, BT119991, Burlywood, Cazarin, DabMachine, Edgar181, JBDJ2833,
Kandar, Lamro, Magioladitis, Michael Devore, Mild Bill Hiccup, Nimlot, Prari, Raoulduke25, Rifleman 82, Sscrofa, 25 anonymous edits

Fatty acid  Source: [Link]  Contributors: - ), 1m y0ur targ, 5 albert square, 5604a, Abeg92, Accurizer, Addshore, Ahoerstemeier, Albmont,
Alsocal, Andonic, Angela, Animum, Antandrus, Anupamsr, Arcadian, Aunt Entropy, Aznshark4, BTOperator150, Bassy101, Belgrano, Belovedfreak, Bencherlite, BernardH, Bobblewik,
Bogey97, Bongwarrior, Bryan Derksen, Btmachine333667, Bubbha, Bugo30, Bustinout244, [Link], Carlquinn, Carynoid, Cburnett, Cheeesemonger, ChemGardener, ChemNerd, Chiros Sunrider,
Christian75, Chuckyack, Cigaro Pizarro, Cindylovesyou, Clarince63, Cmh, Coltj1397, Conversion script, Corbinkirbynewtonscooby22, Cremepuff222, Cyrushehe, DA3N, DSLeB, DamnitFace,
Dante Alighieri, Darklilac, DarkoV, Dave6, Davewho2, [Link], Davidresseguie, Dawnseeker2000, Dcirovic, Deli nk, Delta G, DennyColt, Diderot's dreams, Discospinster, Djk3,
Domenic16, Domstaz, Donarreiskoffer, Doulos Christos, Download, DrGabriela, Dreadstar, Drmies, Drphilharmonic, Dsnow75, Ebuxbaum, Edgar181, Edinburgh Wanderer, Elkman, Epbr123,
EryZ, Ewisely, Excirial, FF2010, FMephit, Fabiform, Famas96, Fedir, Fieldday-sunday, Footwarrior, Frankg, Frecklefoot, Fæ, G00nsf, G3pro, GB fan, Gabethenerd, Gcanyon, GenOrl,
Ghosts&empties, Giftlite, Glenn, Gracenotes' left sock, Greensburger, Hargan, Haripandit, Hasinaisdabest, Hgrosser, Hsart, Ibrahim lodhi, Icairns, Icek, Ike9898, Ilikeeatingwaffles,
ImperfectlyInformed, InfoCan, Istvan, J G Campbell, [Link], JDog Sassy Pants, Jag123, Jaganath, Jay L09, Jaysbro, Jbening, Jdude89, Jfdwolff, Jim1138, Jmrowland, Joe Jarvis, JoeAnderson,
John, Johner, JohnnyA54, Johnsmith12321, Jpmoser14, Jqavins, Jü, Karenjc, Karol Langner, Khukri, Kosigrim, Kristof vt, Ksero, Kukini, Kupirijo, Kutulu, Lagrantierra, Lancethex, Lars
Washington, Linguina, Lubricatedcondoms, Luminaux, Lupin, Mac, Magioladitis, Mandarax, Manke20, Mannafredo, Mar Garina, MarcoTolo, Marcushen3ryal, MastCell, MatthewEHarbowy,
Mentifisto, Mikael Häggström, Mike Biker, Mike713, Miller17CU94, Minesweeper, Modernist, MoleculeUpload, Molybdenumblue, Mozzerati, Muhandes, Muriel Gottrop, N3362, NawlinWiki,
Nbauman, Nicholasmorassutti, Nicklink483, Nikai, Northfox, Numbo3, Nutriveg, OM-Aleks, Odazi, Odie5533, Oiws, Old Moonraker, Patelurology2, Pcyrus, Pedant, Peterlin, Phil Boswell, Phil
Ian Manning, PierreAbbat, Pinethicket, Press olive, win oil, Prestonmag, Pro crast in a tor, Prolog, Quantockgoblin, Queerboy1234, Quelsen, R107, RYNORT, Rajasekhar1961, Randi barnes
2013, Reaper Eternal, Rej5y7, [Link], Rich Farmbrough, Richard Arthur Norton (1958- ), Rjwilmsi, Robertvan1, Ronhjones, Royote, Rror, SEWilco, SabrehamLincoth, Salsb, Sasata,
Scarredintellect, Scott English, SemperBlotto, Several Pending, Sexualala, Shaddack, Shadowjams, Shadowlapis, Shirulashem, Shoy, Slashme, Smokefoot, Snaffu, Snek01, Snigbrook,
Snowmanradio, Snowolf, Sole Soul, Souperbwitch, Spartan-oj, Spikey, Spinningspark, Starblind, StevenLcarroll, Stone, Sundstrj, Sweikart, THEN WHO WAS PHONE?, Tangent747, Taroaldo,
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Diglyceride  Source: [Link]  Contributors: Aqua lem, Arcadian, ArglebargleIV, Dcirovic, Drphilharmonic, Edgar181, Eitch, Fjellstad,
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Oil  Source: [Link]  Contributors: (Didie), 007rex, 10jgwara, 123Hedgehog456, 28421u2232nfenfcenc, 4musicification, 5 albert square, A bit iffy,
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Article Sources and Contributors 86

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Fat  Source: [Link]  Contributors: 01EnterShikari10, 09zoulzm, 124aplele124, 16@r, 7, A D 13, A Softer Answer, [Link], AA, ATER1,
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Article Sources and Contributors 87

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Jrustenhoven, Judgepooley, Jushi, Jusjih, Kakoui, Katalaveno, Kembarawan, Kirien, Knutux, Kraftykyle, Ksenon, L Kensington, [Link], Lagrantierra, Lambanog, Larm93, Ldbio130,
Lightdarkness, Lightmouse, Lignon, Lordandmaker, LotR, Luigizanasi, Lunchboxhero, MGTom, MONGO, Mac, Macy, Mahahahaneapneap, Makeemlighter, Marknesbitt, Marshman,
MarthaHolley, Matt Gies, Matthewcgirling, Mccalliste53, Meeples, Mercurywoodrose, Midori, Mild Bill Hiccup, Mimaterials, Miranda, Mkweise, Mountainscout, Mxn, NellieBly, Nichalp,
Article Sources and Contributors 88

Noctibus, Nohat, Noles1984, Nono64, Nopira, Notheruser, Olivier, Paupamp, Pedro, Pekinensis, Philip Trueman, Pinethicket, Playadom, Ppntori, Prashanthns, Prgrmr@wrk, Pro crast in a tor,
Pstudier, Qutezuce, Qwayzer, RaseaC, Reach Out to the Truth, Reaverdrop, RekishiEJ, Riceball, Rjwilmsi, Rmhermen, Rory096, Rror, SDC, SMC, SV Resolution, Scott Ritchie, Severo, Shoefly,
Shreshth91, SilkTork, Silverchemist, Silverfish, SimonP, Sjschen, Skier Dude, Solipsist, SomeHuman, Sparklingway, Spiritia, Stroppolo, TheGuruTech, ThePerpetualStudent, Thomas bonasera,
Tjhiggin, Toh, Tom Lougheed, Tommy2010, Tommypark95, Tomr90, Transnistria, Treekids, Tresacl, Tropylium, Trusilver, V8rik, Vanderesch, Vincecate, Vuo, WLU, Waitak, Wavelength,
Wertles, Whitebox, Wilibus, Woohookitty, WorthWhatPaid, Xdamr, Xnn, YOSF0113, Yobol, Youandme, Zbd, Zigger, Zzorse, ‫ﻣﺎﻧﻲ‬, 387 anonymous edits

Palm oil  Source: [Link]  Contributors: 1luvly, A. B., Aardnavark, Abtinb, Acalamari, Adiput, Agradman, Ahoerstemeier, Alan Liefting, [Link],
Albmont, Alex Bakharev, [Link], Amikake3, AndyGondorf, Andyd79, Anna Frodesiak, Antandrus, Anwar saadat, Archmage Brian, Areenarena, Atatakakata, Avillia, BT119991, Badagnani,
Barefootguy, Barkeep, Beagel, Beal67, Because1981, Benjamindees, Betswiki, Bkell, Blackcats, Bonadea, Bongwarrior, Bremskraft, Brentt, Brinerustle, Bryan Derksen, Capricorn42, Cdc,
Cgingold, ChemRamirez, Cherylrenee, Chillysnow, Chris Capoccia, Chris Roy, Cimbalom, ClairSamoht, Cloey 101, [Link], Coemgenus, CommonsDelinker, Crl620, D a r l i n g f a c
e, DMacks, Dale Arnett, DanEdmonds, Danielle35, Davehi1, David from Downunder, Dbatreja, Deiz, Deli nk, Deltabeignet, Dolcezza077, Dontworry, Dragon guy, Dream Focus, Drmies,
Drnthe, Dycedarg, Edgar181, Edheitz, Egoddy, Emerson7, Epbr123, Ephebi, Eplebel, Erianna, Eshouthe, Ezzane, Flummery, Foobar, Fractal41x, Franamax, Freespeech4us, Freestyle-69,
Frosted14, Gail, Ghandi dancer, Gigemag76, Gioto, Glane23, Glennhurowitz, Gsarwa, Gunnar Hendrich, H2g2bob, Hai398, Herostratus, Hobsonlane, Horologium, Huayi, Huseyx2, Hyacinth,
Iammercutio, Icedog, Ijriims, Imalm91, JaGa, Jackol, Jakub, Jalen, JamesBWatson, Jay L09, Jedlink, Jeff G., Jeffhall318, Jensbn, John, John McDG, JohnFMayer, Johnfos, Johnvanzyl, KVDP,
Kaeso Dio, Kaldari, Karkaputto, Kkolmetz, Kubigula, LeadSongDog, Lester, Lfstevens, Liffey, Lightmouse, Lights, LilHelpa, LinkinPark, Little sawyer, Lizzay01, LorenzoB, Luigi30, MPF,
MZMcBride, Maggot, Magnificascriptor, Makeemlighter, Malmpoc, Mandarax, Margareta, [Link], Marknagel, Markthemac, Martin H., Masterhomer, Mausy5043, MaxPont, Maximum
Nuts, McSly, Mded, Meggar, Menwith, Merbabu, Mikeblyth, Minimac, Mkativerata, Mmortal03, Modernist, Morpheios Melas, Mr Accountable, NJGW, Nanjareddy, Nemo bis, Neuenglander,
Nhobgood, NickCT, Nicmart, Nicolas1981, Nigeriascholar, Nil Einne, Nipisiquit, Nivagh, NormanJiwan, Notmyrealname, Nunquam Dormio, Nutriveg, Nwbeeson, Oktuck, Olivierd,
Omegawarrior, Optigan13, Peter G Werner, Peterlewis, Petrusim, Pharaoh of the Wizards, Piast93, Piercetheorganist, Piuslxix, Pmj, Prakash Nadkarni, Press olive, win oil, Pseudomonas, Qeny,
RJFJR, Ranking Update, Rep07, RicDod, Rich Farmbrough, Richhill, Rjwilmsi, Robert Merkel, Rodskogj, Roman888, Ronz, Rooooooooooman, Rosdan001, Rp, Rrburke, RudolfRed,
Rusty2005, SAFTAG, SDC, SMasters, Sarcelles, Semperf, Sgorka, ShakataGaNai, SheffGruff, Sir Anon, Skopelos-slim, Smallweed, Smartse, Snowbunny22, So-so the first, Solipsist, Soultaco,
SpaghettiFreak, Spindled, Tabledhote, Tagus, Taxman, TeamOrangutan, Tedder, Tomtefarbror, Tornasole, Ufwuct, Ulric1313, Unioneagle, Urban-sm, Uriel8, User2004, UtherSRG, Vacarme,
Vanished user 47736712, Virnas, Voyaging, WRK, Wahloon, Waitak, Watti Renew, Wavelength, Weedwhacker128, Wfaulk, Wfgiuliano, Wgfcrafty, WhisperToMe, Whitebox, Whosasking,
WikHead, Wikiuser100, Will Beback, Witt1221, Woohookitty, Wsw16, Ytrottier, Zeshion, Zigger, Zodon, Zzorse, 657 anonymous edits

Transesterification  Source: [Link]  Contributors: 4lex, Albmont, Alchemical nocturne, AlexNB, Alsorises, Arcadian, Badagnani, Banus,
Benjah-bmm27, Biopresto, Bobo192, Bonus Onus, Chordate-eukaryote, Chrisbak, Diberri, Discospinster, Eurleif, Family Guy Guy, Fraterm, Hgrosser, Irbisgreif, Itub, JForget, Klip game,
Lamro, Mav, Mkstreet, Nirmos, Nv8200p, Phil Boswell, Pianomanusa, Polyparadigm, Rmhermen, Saravask, Smokefoot, Tarquin, Thedjatclubrock, Trosmisiek, UberScienceNerd, V8rik,
Walkerma, Williamborg, WojPob, Xiong Chiamiov, Youssefsan, Zaphraud, 99 anonymous edits

Hydrogenation  Source: [Link]  Contributors: 168..., 19vwishart, 2261Daryl, AJim, ASarnat, AThing, Altenmann, AndrewHowse, Antandrus,
Beagel, Bensaccount, Biscuittin, Bkell, Borgx, Cacycle, Calmer Waters, Calvero JP, CanadianLinuxUser, CatherineMunro, CerealBabyMilk, ChrisGualtieri, Christian75, Christopher Mann
McKay, CommonsDelinker, Conortodd, CyclePat, DA3N, DTM, DabMachine, Dante Alighieri, David spector, Edgar181, Effeietsanders, El C, Erbaiwu, Erianna, EtienneCha, Excirial,
Fanghong, FayssalF, Flowchemguy, Forenti, Furrykef, GL, Gareth McCaughan, GenQuest, Gene Nygaard, Gigemag76, Gioto, Gsumarji, Guccililpiggy3, Gulliver001, Gökhan, Happyharris,
Headbomb, Headius, Hellbus, Hermann Luyken, Heroeswithmetaphors, Hippolyte, Inoculatedcities, Iridescent, Isopropyl, Itub, [Link], Jackehammond, Jackfork, Janke, Jay L09, Jimp,
Jmendez, Joshuapfohl, Julesd, Karol Langner, Karsten Adam, Kdevans, Keenan Pepper, Kenyon, Kostisl, LOL, Lamro, LeadSongDog, Leslie Mateus, Loupeter, Lovecz, MER-C, MMS2013,
MasterFugu, Mausy5043, Mbeychok, Mdf, Michael Hardy, Mion, Mitchan, Mmmsnouts, Moonrabbit, Müslimix, NJA, Nevit, Nirvana2013, Nono64, Notreallydavid, Novickas, OrangeDog,
Organometallics, OverlordQ, PKT, PaperTruths, Physchim62, Picus viridis, Pinethicket, Poor Yorick, Qaddosh, RazorICE, RealGrouchy, RedHillian, Rhadamante, RickyWiki, Rjwilmsi,
SeventyThree, Shadow Puppet, Shawnc, SheenShin, Skittleys, Smokefoot, Soliloquial, Soyseñorsnibbles, Spalding, Stephenb, Stone, Tabledhote, Takometer, Tarotcards, Taurrandir, The Anome,
The MoUsY spell-checker, Tides, Trackbar, Turnstep, Tyciol, Tyler, V8rik, Vortexrealm, Vuo, Whosasking, Wimvandorst, Wjsams, Woohookitty, Wspencer11, Ww, ~K, ‫ﮐﺎﺷﻒ ﻋﻘﯿﻞ‬, 210
anonymous edits

Saponification  Source: [Link]  Contributors: Ace Class Shadow, Armeria, ArnoLagrange, Aronzak, Arthena, Asrghasrhiojadrhr, Avoided, Axl,
Beachclub, Beakerboy, Belg4mit, Blackcats, Bubalub, Charles Matthews, Crescentia moonshine, Curmudgeon3, Cyberoidx, DaGizza, Dawn Bard, Deepblue123, DocKrin, Donarreiskoffer,
Drpagel, Drphilharmonic, Dylanlucas, Epbr123, Escape Orbit, Fish and karate, Foolip, Geni, Giraffedata, Hadal, Headbomb, Hellbus, Hemmer, IdahoEv, Irishguy, Itub, Iulius, IvanLanin, Jj137,
Jmaes123, Kirrages, Kjkolb, Logan, Lucretiab, MKoltnow, Magister Mathematicae, Maimai009, Malcolmd83, Mboverload, MuffinTheGeek, Nmulder, OMCV, Paweł ze Szczecina,
Peregrine981, Phoenix.v2, Postdlf, Queenholly, Qweeer, RG2, Refsworldlee, RichardMcCoy, Rickproser, Riventree, Roadrunner, Scm83x, Smokefoot, Soap, Stevegallery, Tabletop,
TheObtuseAngleOfDoom, Thubten108, Uncle G, V8rik, Veesicle, Vegaswikian, Veinor, Walkerma, Wizard191, WpZurp, Xenowiki, Yyy, 159 anonymous edits
Image Sources, Licenses and Contributors 89

Image Sources, Licenses and Contributors

File:Butyric acid [Link]  Source: [Link]  License: Public Domain  Contributors: Calvero.
Image:[Link]  Source: [Link]  License: GNU Free Documentation License  Contributors: Original uploader was (Automated
conversion) at [Link]
Image:Isomers of oleic [Link]  Source: [Link]  License: Public Domain  Contributors: Edgar181
File:Fatty acid [Link]  Source: [Link]  License: Public Domain  Contributors: user:Foobar
Image:Fatty alcohol - [Link]  Source: [Link]  License: Public Domain  Contributors: Edgar181
Image:Transesterification [Link]  Source: [Link]  License: Public Domain  Contributors: Ertua
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: NEUROtiker
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Ed (Edgar181)
File:[Link]  Source: [Link]  License: Public Domain  Contributors: Ed (Edgar181)
Image:PIP2 cleavage to IP3 and [Link]  Source: [Link]  License: GNU Free Documentation License
 Contributors: Original uploader was Eak435s at [Link] Later version(s) were uploaded by DO11.10 at [Link].
File:[Link]  Source: [Link]  License: Public Domain  Contributors: Edgar181
Image:Fat triglyceride shorthand [Link]  Source: [Link]  License: Public Domain  Contributors:
Wolfgang Schaefer
Image:StatinPathway_WP430.png  Source: [Link]  License: Creative Commons Attribution 3.0  Contributors: Nathan
Salomonis, Alexander Pico, Kristina Hanspers, Thomas Kelder, Bruce Conklin
File:[Link]  Source: [Link]  License: Public Domain  Contributors: User:Erasoft24
File:Quaternary ammonium [Link]  Source: [Link]  License: Public Domain  Contributors: Fvasconcellos
File:Italian olive oil [Link]  Source: [Link]  License: Creative Commons Attribution-ShareAlike 3.0 Unported  Contributors:
my friend
File:[Link]  Source: [Link]  License: Public Domain  Contributors: Benjah-bmm27
File:[Link]  Source: [Link]  License: Public Domain  Contributors: Original uploader was Bigplankton at [Link] Later
versions were uploaded by Sunholm at [Link].
Image:Decorative [Link]  Source: [Link]  License: Public Domain  Contributors: Original uploader was Phanton at
[Link]
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Smokefoot
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Smokefoot
File:[Link]  Source: [Link]  License: unknown  Contributors: Bapti, Jarekt, Jean-Frédéric, Kaldari, Pixeltoo, Thelmadatter
File:Pears'[Link]  Source: [Link]  License: Public Domain  Contributors: uncredited commercial artist
Image:Palmolive soap 1922 advertisement ladies home [Link]  Source: [Link]
 License: Public Domain  Contributors: EugeneZelenko, [Link], Infrogmation, Kilom691, Lotsofissues, Man vyi, Mutter Erde, Sevela.p, Skipjack, Tekstman
File:Liquid antibacterial [Link]  Source: [Link]  License: Public Domain  Contributors: Malinaccier
Image:Soap and Detergent manufacturing process [Link]  Source: [Link]  License: Public
Domain  Contributors: Soap_and_Detergent_manufacturing_process_02.png: *Soap_Detergent_manufacturing.JPG: KVDP derivative work: Azcolvin429 (talk) derivative work: Northumbrian
(talk)
Image:Soap [Link]  Source: [Link]  License: GNU Free Documentation License  Contributors: David Monniaux
Image:Savon de [Link]  Source: [Link]  License: Creative Commons Attribution-ShareAlike 3.0 Unported  Contributors:
User:[Link]
Image:Generic [Link]  Source: [Link]  License: unknown  Contributors: Sam Smith
Image:Azul e [Link]  Source: [Link]  License: Creative Commons Attribution-ShareAlike 3.0 Unported  Contributors: 77bcr77
File:[Link]  Source: [Link]  License: GNU Free Documentation License  Contributors: Herbythyme, Jorgebarrios, KaurJmeb,
Mikomaid, Wst, 3 anonymous edits
File:Makeup [Link]  Source: [Link]  License: Creative Commons Attribution 2.5  Contributors: Original uploader was Petar
Milošević at [Link]
File:Nefertiti [Link]  Source: [Link]  License: Creative Commons Attribution-ShareAlike 3.0 Unported  Contributors:
Arkadiy Etumyan
File:Lautrec woman at her toilette [Link]  Source: [Link]  License: Public Domain  Contributors:
AndreasPraefcke, Hailey C. Shannon, Petrusbarbygere, Ranveig, Sandik, Wst
File:Pre-wedding [Link]  Source: [Link]  License: Creative Commons Attribution 2.0  Contributors: Ruth Ellison
File:Jim [Link]  Source: [Link]  License: Creative Commons Attribution 2.0  Contributors: Andre Engels, Nilfanion, Para,
Pfctdayelise, Ranveig, Thuresson, Vonvon
File:Kerala kathakali [Link]  Source: [Link]  License: Creative Commons Attribution-Sharealike 2.0  Contributors:
Thorsten Vieth from Bangalore, India
File:Professional Make-up [Link]  Source: [Link]  License: Creative Commons Attribution-Sharealike 3.0
 Contributors: TitanOne (talk)
File:Alek [Link]  Source: [Link]  License: Creative Commons Attribution-Sharealike 2.0  Contributors: Vonvon
Image:Olive oil from [Link]  Source: [Link]  License: Creative Commons Attribution-Share Alike  Contributors:
Lemone
File:Palm oil [Link]  Source: [Link]  License: Creative Commons Attribution-Sharealike 2.5  Contributors: en:User:Whitebox
File:Huile de palme biologique [Link]  Source: [Link]  License: Public Domain  Contributors: Romain Behar
File:Elaeis guineensis MS [Link]  Source: [Link]  License: Creative Commons Attribution-Sharealike 2.5
 Contributors: Marco Schmidt
File:2006palm [Link]  Source: [Link]  License: Public Domain  Contributors: Anwar (talk). Original uploader was Anwar saadat at
[Link]
File:Zurich [Link]  Source: [Link]  License: Free Art License  Contributors: RSPO
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Benjah-bmm27, Edgar181
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Smokefoot
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Smokefoot
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Smokefoot
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Smokefoot
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Smokefoot
Image:[Link]  Source: [Link]  License: Public Domain  Contributors: Smokefoot
Image Sources, Licenses and Contributors 90

Image:[Link]  Source: [Link]  License: Creative Commons

Attribution-Sharealike 3.0,2.5,2.0,1.0  Contributors: -
Image:[Link]  Source: [Link]  License: Creative Commons
Attribution-Sharealike 3.0,2.5,2.0,1.0  Contributors: Original uploader was V8rik at [Link]
Image:[Link]  Source: [Link]  License: Creative Commons Attribution-Sharealike 3.0  Contributors:
V8rik (talk). Original uploader was V8rik at [Link]
Image:Verseifungsreaktion [Link]  Source: [Link]  License: Public Domain  Contributors: Yikrazuul
Image:Verseifungsreaktion [Link]  Source: [Link]  License: Public Domain  Contributors: Yikrazuul
Image:Verseifungsreaktion [Link]  Source: [Link]  License: Public Domain  Contributors: Yikrazuul
License 91

License
Creative Commons Attribution-Share Alike 3.0 Unported
//[Link]/licenses/by-sa/3.0/