CHEMISTRY
INVESTIGATORY
PROJECT
TOPIC:- Uses of Aspirin
and its side effect
Introduction
Aspirin is the most widely used over-
the-counter drug in the world. The
average tablet contains about 325
milligrams of acetylsalicylic acid with
an inert binding material such as
starch. Aspirin is used to relieve
pain, reduce inflammation, and lower
fever. Aspirin originally was derived
by boiling the bark of the white
willow tree. Although the salicin in
willow bark has analgesic properties,
purified salicylic acid was bitter and
irritating when taken orally. Salicylic
acid was neutralized with sodium to
produce sodium salicylate, which
was better tasting but still irritated
the stomach. Salicylic acid could be
modified to produce phenyl
salicylate, which was better tasting
and less irritating, but released the
toxic substance phenol when
metabolized. Felix Hoffman and
Arthur Eichengrün first synthesized
the active ingredient in aspirin,
acetylsalicylic acid, in 1893.
Preparations of aspirin
Aim:
The purpose of this experiment is to
prepare acetylsalicylic acid, a.k.a.
aspirin.
Theory:
Aspirin, acetylsalicylic acid, was first
synthesized in 1893 by Felix Hofmann, a
chemist for the German firm of Bayer.
This compound had the medicinal
properties of salicylic acid, an extract of
willow bark, without the unpleasant
taste or the high degree of irritation of
the mucous membranes lining the
mouth, gullet, and stomach. Aspirin is
both an organic ester and an organic
acid. It is used extensively in medicine
as a pain killer (analgesic) and as a
fever-reducing drug (antipyretic). When
ingested, acetylsalicylic acid remains
intact in the acidic stomach, but in the
basic medium of the upper intestinal
tract, it hydrolyzes forming the
salicylate and acetate ions. However, its
additional physiological effects and
biochemical reactions are still not
thoroughly understood. Aspirin (molar
mass of 180.2 g/mol) is prepared by
reacting salicylic acid (molar mass of
138.1 g/mol) with acetic anhydride
(molar mass of 102.1 g/mol). Aspirin is a
weak monop rotic acid.
Preparation using
phenol
Preparation using
phenol
Acetaminophen is an amide, a
compound that is a derivative
of ammonia that has been
reacted with an acidic
substance, in this case, acetic
acid. Acetaminophen acts as a
fever reducer and pain reliever.
It can be found in several
analgesic preparations, such as
Tylenol, some of which may
contain other ingredients such
as caffeine and buffers.
Qualitatively, the purity of an
aspirin or acetaminophen
sample can be determined from
its melting point. The melting
point of a substance is
essentially independent of
atmospheric pressure, but it is
always lowered by the
presence of impurities (a
colligative property of pure
substances). The degree of
lowering of the melting point
depends on the nature and the
concentration of the impurities.
Procedure:
1. Obtain a 50 mL Erlenmeyer
flask, a filter flask, a Buchner
funnel, a watch glass, a
thermometer, a weigh boat,
and two pieces of filter paper
from the supply area. If the
Erlenmeyer flask contains
water droplets, heat it on a
Bunsen burner to remove the
moisture.
2. Obtain the mass of the watch
glass and record it on your data
sheet.
3. Weigh about 2 grams of
salicylic acid into the
Erlenmeyer flask. Do not try to
weigh out exactly 2.000 grams
of the chemical; your results
will be fine with +/– 0.250
grams of salicylic acid. Since
you won’t need the mass of the
flask for further work, zero the
balance with the flask in the
pan. Then remove the flask
from the balance and dispense
the amount of chemical you
need. Do not leave the flask on
the balance pan and try to get
the salicylic acid into it, you’ll
make a mess.
4. Measure about 5 mL of
acetic anhydride (density 1.082
g/mL) into a graduated
cylinder, then pour this into the
flask with the salicylic acid.
Acetic anhydride will be in the
fume hood, with a graduated
cylinder to measure it in. Swirl
the contents of the flask gently
to mix them. The solid may not
all dissolve. Add 5 drops of 85%
phosphoric acid (H3PO4). This
will also be in the hood.
5. Set up a Bunsen burner and
ring stand. Use a 250 mL
beaker to make a water bath.
Clamp the Erlenmeyer flask in
the water bath.
6. Heat the water bath to about
75°C. Maintain this
temperature for 15 minutes.
Move the burner away from the
bath when the water gets too
hot. A few degrees of
temperature fluctuation will not
hurt the reaction, but excess
heat will release acetic
anhydride vapor.
7. At the end of 15 minutes, the
salicylic acid should all have
dissolved and been converted
to acetylsalicylic acid. Remove
the burner, and cautiously add
about 2 mL of distilled water to
the flask. This will decompose
any remaining acetic
anhydride. You may observe
some hot acetic acid vapor
being formed in this step.
8. When the liquid has stopped
giving off vapor, remove the
flask from the water bath and
add 20 mL of distilled water. If
two layers form, or the liquid is
hazy, swirl the flask to obtain a
clear solution. Allow the flask to
cool until you can handle it
comfortably. While the flask
cools, crystals of aspirin will
probably appear. Do not move
the flask or handle it
excessively. The largest, purest
crystals form slowly from a
solution that is not being
stirred.
9. Once the flask has cooled
until you can handle it, cool it
further in an ice bath. Again,
avoid swirling or stirring it any
more than necessary. Keep the
flask in the ice bath about 5
minutes.
10. Assemble the apparatus for
a suction filtration. Place the
filter paper in the Buchner
funnel, wet it with distilled
water, and start the aspirator.
Pour the contents of the flask
into the filter. Use your spatula
to get as much of the aspirin
into the funnel as possible.
11. Draw air through the funnel
for a few minutes to dry the
crystals. Use the bottom of the
Erlenmeyer flask to compress
the crystals and spread them
so they cover the filter paper.
Transfer the crystals to a weigh
boat.
12. Rinse the small Erlenmeyer
flask well, then add 20 mL of
distilled water and return the
crystals to the flask. You will
have to bend the weigh boat
and use your spatula to move
the crystals. Transfer as much
of the solid as you can.
13. Heat the contents of the
flask to boiling. The crystals
should all dissolve. If they
don’t, add a few milli litres of
water to dissolve them. When
all the crystals have dissolved,
remove the flask from heat and
cool it in water bath (a 250 mL
beaker with tap water is fine).
Do this recrystallization quickly
to avoid hydrolysis of the
aspirin.
14. When the flask and its
contents are cool enough to
handle, cool them further in an
ice bath. Keep the flask in ice
for about 5 minutes.
15. Filter the crystals as you did
in step 11. Transfer them to the
watch glass.
16. Weigh the crystals on the
watch glass, and calculate your
percent yield.
17. Scrub the flasks and the
Buchner funnel with soap and
water, then rinse them well,
before you return them to the
supply area. Rinse the weigh
boats and discard them.
Uses
• Aspirin is used in the
treatment of a number of
conditions, including fever,
pain, rheumatic fever and
inflammatory diseases, such as
rheumatoid arthritis,
pericarditis, and disease. Lower
doses of aspirin have also
shown to reduce the risk of
death from a heart attack, or
the risk of stroke in some
circumstance. There is some
evidence that aspirin is
effective at preventing
colorectal cancer, though the
mechanisms of this effect are
unclear
• Pain: Uncoated aspirin
tablets, consisting of about
90% acetylsalicylic acid.
• Headache: Aspirin, either by
itself or in a combined
formulation, effectively treats
some types of headache, Fever:
Like its ability to control pain,
aspirin's ability to control fever
is due to its action on the
prostaglandin system. Although
aspirin's use as an antipyretic
in adults is well-established,
many medical societies and
regulatory agencies strongly
advise against using aspirin for
treatment of fever in children
because of the risk of Reye's
syndrome. Swelling and
inflammation: Aspirin is used as
an anti-inflammatory agent for
both acute and long-term
inflammation, as well as for
treatment of inflammatory
diseases
• Heart attacks and stroke:
Aspirin is an effective analgesic
for acute pain, but is generally
considered inferior to ibuprofen
for the alleviation of pain
because aspirin is more likely
to cause gastrointestinal
bleeding. Aspirin is generally
ineffective for those pains
caused by muscle. As with
other NSAIDs, combinations of
aspirin and caffeine provide
slightly greater pain relief than
aspirin alone. Aspirin is used in
the treatment of migraine
• Aspirin is an important part
of treatment of those who have
had a myocardial infraction
(heart attack).
• For a subset of the people,
aspirin may help prevent heart
attacks and strokes. In lower
doses, aspirin prevents the
progression of cardiovascular
disease. Frequently, aspirin is
combined with ADP receptor
inhibitors to prevent blood
clots. • Aspirin reduces the
overall risk of both getting
cancer and dying from cancer.
Some conclude the benefits are
greater than the risks due to
bleeding in those at average
risk
• Aspirin decomposes rapidly in
solutions of ammonium acetate
or of the acetates, carbonates,
citrates, or hydroxides of the
alkali metals. It is stable in dry
air, but gradually hydrolyses in
contact with moisture to acetic
and salicylic acids.
• Decreases inflammation:
Inflammation is a component of
plaque build-up and inflamed
plaque is more likely to cause a
heart attack or stroke. Aspirin
fights the inflammation
associated with heart disease.
• Inhibits blood clots: Some
prostaglandins in the blood
trigger a series of events that
cause blood platelets to clump
together and form blood clots.
Thus, when aspirin inhibits
prostaglandins, it inhibits the
formation of blood clots as well.
• Reduces the risk of death:
Research has shown that
regular aspirin use is
associated with a reduction in
death from all causes,
particularly among the elderly,
people with heart disease, and
people who are physically unfit.
• Remove sweat stains: Make a
paste using ground aspirin and
water, and apply it over the
yellowed area before
laundering. The salicylic acid in
aspirin is an effective cleaning
agent, working the same way
that other acidic substances
like vinegar and lemon juice do.
• Soothe mosquito bites: To
tame itching caused by a
mosquito bite, rub a dampened
aspirin pill over the inflamed
area until discomfort subsides.
• Keep soil fresh:To keep your
garden thriving, add one aspirin
per gallon of watering water in
order to prevent fungus from
growing around the roots of
fresh flowers. The treatment
will also result in longer- lasting
flowers once the blooms are
cut.
• Combat light cases of
dandruff To remove pesky dry
skin flakes from your scalp,
crush two aspirin tablets and
add them to a dab of shampoo
before washing hair as usual.
• Remove rust spots: To
remove rust spots crush an
aspirin or two and wet the
stained area, then sprinkle the
powder onto the rust and let it
sit for 10 minutes before wiping
away with a damp sponge.
• Prevent Cancer: An aspirin a
day may help keep cancer
away. A study published in the
Annals of Oncology found the
benefits of taking aspirin to
prevent some types of cancer
outweigh the harms. The
researchers note the effects of
aspirin are not apparent until at
least three years after the start
of use, and some benefits are
sustained for several years
after stopping daily aspirin
therapy in long-term users. If
those between 50 and 65
started taking aspirin daily for
at least 10 years, there would
be a nine percent reduction in
the number of cancers, strokes,
and heart attacks
Common Side Effects of Aspirin:
➢ Vomiting
➢ Stomach pain
➢ Heartburn
➢ Drowsiness
➢ Nausea
Serious Side Effects of Aspirin:
➢ Ringing in the ears
➢ Loss of hearing
➢ Hives or rash
➢ Swelling of the eyes, face, lips,
tongue, or throat
➢ Wheezing or breathing
difficulties ➢ Hoarseness
➢ Fast heartbeat or fast breathing
➢ Cold, clammy skin
➢ Bloody vomit or vomit that
looks like coffee grounds
➢ Bright red blood in stools or
black or tarry stools
Conclusion
The theory of this experiment
was that acetylsalicylic acid,
also known as aspirin, can be
synthesized from salicylic acid,
acetic anhydride, and
phosphoric acid. Esters are
formed through Fischer
esterification. The information
from the data acquired from
this experiment reveals that
the correct product,
acetylsalicylic acid, was
produced. The techniques used
in this experiment include, but
are not limited to, the following:
TLC; filtration; IR spectrometry;
NMR spectrometry.
Chromatography, IR
spectrometry, and NMR
spectrometry are commonly
used to verify the purity of
medications. Filtration is used
to finish drying organic material
prior to the spectrometries.
Gallery
Bibliography
• www.slideshare.net
• www.google.co.in
• Chemistry NCERT (XII)
