OGANIC CHEMISTRY (LABORATORY)

CM0134-1L/B2
4TH quarter S.Y. 2019-2020

Recrystallization
MENDOZA, Joseph Albert1, VERDIDA, Reginald A.2
1Professor, School of Chemical, Biological, and Materials Engineering and Sciences, Mapúa University; 2Student, CM134-1L/B2, Mapúa University

Introduction
Recrystallization is a technique used to purify chemicals by dissolving the impurities and a compound in
the solvent. A compound will be left behind because the compound or impurities can be closed out of the solution.
Liquid-liquid extraction also known as solvent extraction and partitioning, is a method to separate compounds
based on their relative solubility into different and miscible liquids, usually water and an organic solvent. It is an
extraction of a substance from one liquid into another liquid phase. The process involves dissolving a solid into
an appropriate solvent at an elevated temperature and allowing the crystals to reform on cooling, so that any
impurities remain in solution.

The principle behind recrystallization is that the amount of solute that can be dissolved by a solvent
increase with temperature. In recrystallization, a solution is created by dissolving a solute in a solvent at or near
its boiling point. At this high temperature, the solute has a greatly increased solubility in the solvent, so a much
smaller quantity of hot solvent is needed than when the solvent is at room temperature. When the solution is
later cooled, after filtering out insoluble impurities, the amount of solute that remains dissolved drops
precipitously. At the cooler temperature, the solution is saturated at a much lower concentration of solute. The
solute that can no longer be held in solution forms purified crystals of solute, which can later be collected.

Materials
 Test tube rack
 Buchner-funnel  Erlenmeyer Flask
 Thomas-Hoover Melting apparatus  Beaker
 Hot plates  Capillary tubes
 Stemless Funnel  Oven
 Funnel support  Filter paper
 24 micro test tubes  Pipette
Reagents
 Crude Acetanilide
 Acetamide
 Distilled water
 Acetanilide
 Ethanol
 Aspirin
 Ethyl Acetate
 Benzene
 Naphthalene
 Benzoic acid
 Sucrose

Methodology
The entirety of this experimentation about recrystallization was actually divided into two parts, which is
experimenting to identify which choice of solvent would best fit the process of recrystallization and the
recrystallization experiment itself.

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 OGANIC CHEMISTRY (LABORATORY)
CM0134-1L/B2
4TH quarter S.Y. 2019-2020

PART I: Choice of Solvent

The test compounds given subject to recrystallization are acetamide, acetanilide, aspirin, benzoic acid,
naphthalene and sucrose which to be observed together with the solvents water, ethanol, benzene and ethyl
acetate.

PROCEDURES:

1. Weigh approximately 0.10 grams of the test compound and put it in a micro test tube.

2. Dissolve the test compound with 2ml of cold water and observe solubility behavior. Record your
observation.

3. Set the micro test tube to room temperature. Boil the mixture and observe solubility behavior. Record
your observation.

4. Repeat procedures 1 to 3 in to the same compound using the other solvents (i.e. ethanol, benzene
and ethyl acetate)

5. Repeat procedures 1 to 4 in all the remaining test compounds.

PART II: Recrystallization

Before actually starting the experiment, prepare first the necessary set-ups needed in the course of
experimentation.

 Fluted filter paper

Cut out a piece of filter paper into a circle with a diameter of about 5 inches. Fold the circular paper
into two, and then into four, eight, sixteen and so on. Open the folded filter paper.

 Hot gravity filtration set-up

Assemble the set up shown

 Vacuum filtration set-up

Assemble the set-up shown. Cut and weigh an ashless filter paper and lay it flatly in the Buchner
funnel. Take not of the weight of the filter paper. It is advisable to moisten slightly the filter paper with the
solvent used.

PROCEDURES:

1. Heat approximately 100 mL of water.

2. Weigh approximately 3.5 grams crude acetanilide. Take note of the exact weight

3. Dissolve the impure acetanilide with 30 mL of water using a 150-mL beaker.

4. Using the hot plate, slightly boil the mixture. When the mixture starts to, ass 2 mL portions of the
previously heated water with stirring until the white solid completely dissolves. Maintain the temperature at 90C
while adding hot water. Take note of the total volume of water used. It should not exceed 70 mL since the
solubility if acetanilide of 4.30 g/100 mL water.
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 OGANIC CHEMISTRY (LABORATORY)
CM0134-1L/B2
4TH quarter S.Y. 2019-2020

5. If the solution is colored, add a small amount of activated carbon.

6. Using the set-up for hot gravity filtration, pour the solution into the fluted filter paper situated in the
stemless glass funnel.

7. At this point, you should obtain a colorless filtrate. If this is not possible, add more activated carbon
then reheat the mixture. Repeat the filtration process.

8. Remove the flask from the hot plate and discard the residue.

9. Cool down the filtrate to room temperature, then place it in an ice bath and continuously stir the mixture
until crystallization is complete. This process will take around 10 - 15 minutes. Scratch the side of the flask or
add some crystals of acetanilide if crystallization fails to occur.

10. Once crystallization is complete, vacuum filter the solution. Wash the crystals with 2mL of cold water.

11. Dry the crystals and weigh them. Compute for the percentage recovery.

12. Determine the melting point of the purified crystals.

Results and analysis

PART I: Choice of Solvent

Compound Water Ethanol benzene Ethyl Acetate

Cold Hot Cold Hot Cold Hot Cold Hot
Acetamide S S S S I S S S
Acetanilide I I I S I S S S
Aspirin I I S S I S S S
Benzoic Acid I S S S S S S S
Naphthalene I I I S S S S S
Sucrose S S I S I I I I

Compound Solvent appropriate for Recrystallization

Acetamide Benzene
Acetanilide Benzene
Aspirin Benzene
Benzoic Acid Water
Naphthalene Ethanol
Sucrose Ethanol

Judging from all the data gathered by the researchers as given in the table above, solubility of each test
compounds were determined in contrast with different solvent used. Acetamide was basically soluble both in hot
and cold water, ethanol and ethyl acetate solvents except using hot and cold benzene which exhibits
crystallization reaction. Aspirin on the other hand was both insoluble in hot and cold water and ethanol solvents
and both soluble in hot and cold ethyl acetate however, the compound exhibits crystalization when dissolved
with hot to cold benzene solvent. For Benzoic acid, the compound was both soluble in both hot and cold ethanol,

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 OGANIC CHEMISTRY (LABORATORY)
CM0134-1L/B2
4TH quarter S.Y. 2019-2020

benzene and ethyl acetate solvents except using cold and hot water solvent which caused the compound to
undergo crystallization. Naphthalene also was both soluble in both hot and cold benzene and ethyl acetate
solvents and both insoluble in both hot and cold water solvent however, using hot and cold ethanol solvent, the
compound exhibits crystallization reaction. Lastly, Sucrose in contrast was both insoluble in both hot and cold
benzene and ethyl acetate solvents and both soluble in both hot and cold water solvent but goes crystallization
reaction if dissolved using hot and cold ethanol solvent.

PART II: Recrystallization of Impure Acetanilide

Weight of crude acetanilide in grams 3.50

Weight of Filter paper in grams 1.27
Weight of pure acetanilide in grams 1.39
Volume of water used in mL 26
Melting point of pure acetanilide in Celsius 115
Percentage Recovery 39.71 %

Step Observation
Boiling of pure acetanilide 1.27
Addition of activated carbon 1.39
Hot gravity filtration 26
Cooling in an ice bath 115
Vacuum Filtration 39.71

Conclusion
Recrystallization works only when the proper solvent is used. The solute must be relatively insoluble in
the solvent at room temperature but much more soluble in the solvent at higher temperature. At the same time,
impurities that are present must either be soluble in the solvent at room temperature or insoluble in the solvent
at a high temperature.

Also appropriate would be a solvent in which the impurities are insoluble at a high temperature because
they will remain solid in the boiling solvent and can then be filtered out.

In general, a very polar solute will easily be dissolved in a polar solvent and will be fairly insoluble in a
non-polar solvent. Frequently, having a solvent with slightly different polarity characteristics than the solute is
best because if the polarity of the two is too closely matched, the solute will likely be at least partially dissolved
at room temperature.

Technically speaking, recrystallization is a way for purification. This technique allows for the purification
of a crude material. The small loss in yield is made up by the high gain in purity. The purity of the material
obtained can be correlated to the sharpness and veracity of the melting point data and this was observed.

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