Exercise 3
SEPARATION AND PURIFICATION OF ORGANIC COMPOUNDS
CRYSTALLIZATION
Crystallization is a highly effective method for the purification of organic substances, provided
that the physical properties of a given compound permit its purification in this manner. It involves the
process of dissolving the material to form a saturated solution in a suitable solvent at an elevated
temperature, filtering while hot to remove any suspended insoluble particles, and letting crystallization
proceed.
A desirable solvent for crystallization has the following properties: 1) dissolves the solute readily
at an elevated temperature, but only sparingly at a lower temperature (room temperature); 2) gives no
chemical reaction with the solute; 3) is sufficiently volatile so that it may be removed easily from the
purified crystals.
Separation of crystals before the hot solution has all passed through the filter paper can be
prevented by preheating or continuous heating of the funnel. Preheating may be accomplished by passing
hot solvent through the funnel. Continuous heating may be done with steam, hot water, or electrical jacket
used with the funnel. The solution may be heated from time to time while filtration is carried out.
Crystallization involves three consecutive stages: 1) removal of impurities which may retard or
inhibit crystal formulation; 2) nucleus formation; and 3) encouragement of growth of crystals to visible
form.
When samples contain colored impurities that give rise to solutions and crystals that are
yellowish or brownish when they should be colorless or are of an off-color rather than a pure color, they
may be treated with decolorizing carbon (animal charcoal or bone black). The fine carbon particles
present a large, active surface upon which soluble colored substances which serve as impurities may be
adsorbed, particularly the polymeric, resinous and reactive by-products that appear in traces in most
organic reaction mixtures. The decolorizing carbon is added to the hot solution prior to filtration, and the
solution is kept hot for a brief period, shaken to wet the carbon, and filtered. Adsorption occurs very
rapidly, and no advantage is gained by boiling the suspension for several minutes. Animal charcoal is
actually less effective at a high than a low temperature, and the only reason for operating at boiling
temperature is to keep the substances being crystallized in solution. It is a mistake to use more
decolorizing carbon than is actually needed, for an excess may adsorb some of the sample and cause
losses. Removal of impurities which retard crystal formation may also be affected by solubility or
volatility differences.
Nucleus formation may be spontaneous or indirect. Spontaneous nucleus formation, usually at the
vicinity of the freezing point of the compound, is caused by the orientation and aggregation of sufficient
number of molecules which may give rise to a crystal nucleus. For organic substances which do not
crystalize readily even from saturated solutions, a small crystal of the pure material may be added to
induce the crystallization process—a technique known as “seeding.” Crystallization can be induced also
by scratching the sides or bottom of the container with a glass rod. The microscopic scratches in the glass
surface provide sharp edges upon which crystals growth may start.
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Growth of the crystal may be encouraged by stirring or agitation. This practice results in
distribution of the nuclei throughout the solution. In supersaturated solutions, growth of crystals may be
inhibited as a result of restricted motion of molecules. In this case, crystallization is effected by seeding or
by scratching the sides of the vessel with a glass rod.
The quality of the crystals obtained after the process is ascertained by melting point
determination. If found to be still impure, re-crystallization with fresh solvent may be necessary.
Test Compounds: Apparatus/Materials:
benzoic acid beaker
sodium chloride glass rod
methylene blue wire gauze
brown sugar tripod
Bunsen burner
Reagents: test tube
animal charcoal medicine dropper
5% nitric acid solution filter paper
1% silver nitrate solution ice
distilled water
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PROCEDURE
A.
1. In a beaker, prepare a mixture consisting of 1g benzoic acid, a pinch of NaCl and 10 drops of
methylene blue or congo red.
2. Add 100 mL distilled water and heat, while stirring.
3. When the benzoic acid has dissolved, add 0.5g of animal charcoal, and continue heating with
vigorous stirring.
4. Bring the solution to boiling and filter while still hot.
5. Collect 5 mL of the hot filtrate in the test tube labeled “slow cooling” and set it aside to cool
slowly.
6. Collect another 5 mL of the hot filtrate in a second test tube and submerge in a beaker of ice
water. Label this “rapid cooling: and set aside. Collect the remaining filtrate in another beaker
or flask.
7. Record observation of the following: the color of the filtrate, the size of the crystals formed in
rapid cooling and in slow cooling process.
8. Separate the crystals by filtration. Wash twice with cold distilled water. Spread crystals on a
filter paper on a watch glass and allow to dry. Cover with another piece of clean paper while
drying to protect form dust and other impurities.
9. Test for the completeness of the separation:
Dissolve a small amount of the purified crystals in 1 mL hot distilled water in a test tube.
Acidify with 1 drop of 5% nitric acid and add 2 drops of 1% AgNO 3. Observe and record the
result.
B.
1. Dissolve one gram of brown sugar in 25 mL distilled water in a beaker. Get 2 mL of this
solution in a test tube and set aside as control. Note the color of this solution.
2. Heat the remaining solution to nearly boiling. Add 0.5 gram of animal charcoal with constant
stirring. Continue heating and stirring for a few seconds. Filter the solution while still hot.
3. Transfer 2 mL of the filtrate in a test tube. Compare its color with that of control.
Questions
1. How are colored impurities removed from crystals?
2. Why is it necessary to filter the solution while still hot?
3. What are the methods of inducing crystal formation from solution?
4. What factors cause the difference in the size of crystals formed?
5. How is the completeness of separation of the benzoic acid crystals from sodium chloride known with
the addition of AgNO3 solution?
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DATA AND ANSWER SHEET
Name _________________________________________________ Date__________________
Class Schedule _________________________________________ Rating _________________
Group No. _____________________________________________
Exercise 3
Separation and Purification of Compounds
Crystallization
I. Results and Observations
1. Description of mixture:
a. Before heating ____________________________________________________
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b. While heating ____________________________________________________
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2. Crystals formed in rapid cooling
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Crystals formed in slow cooling
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3. Solutions of purified crystals + 1-2 drops of 1% AgNO3
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4.
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II. Answers to Questions
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