CHAPTER 4

RECRYSTALLIZATION
CLEAR AS A CRYSTAL
Morano, Jeanelle Denise R.
Mendoza, Janice Leslie M.
Mendoza, Maria Laura Isabel D.
Navales, Edgardo Antonio R.
Navarro, Micah Linell L.

Abstract
Recrystallization is the simplest and
most widely used operation for purifying
organic solids that differ in their solubility at
different temperature. In this experiment,
Acetanilide was used as the pure organic
compound. Acetylation of Aniline and Acetic
Anhydride yields the crude product or crude
Acetanilide. The Acetanilide will undergo
another crystallization process using the
preferred Recrystallizing Solvent. The
product of the 2nd crystallization will be the
Pure Acetanilide. Recrystallization is based
on the fact that the solubility of a solid in a
given
solvent
increases
with
the
temperature of the solvent.

Introduction
An impure compound dissolved (the
impurities must also be soluble in the
solvent) to prepare a highly concentrated
solution at high temperature. The solution is
cooled.
The impure substance will
crystallize in a purer form because the
impurities wont crystallize yet, therefore
leaving the impurities behind in the solution.
A filtration must be used to separate the
more pure crystals at this point. The slower
the rate of cooling, the larger the crystals
are that form. The disadvantage of

recrystallization is that it takes a long time.

Also, it is very important that the proper
solvent is used. The advantage or
recrystallization is that, when carried out
correctly, it is a very effective way of
obtaining a pure sample of some product or
precipitate.
Experimental
A. MATERIALS
The materials used for the experiment were
the following: Erlenmeyer flask, Bunsen
burner, test tubes, wire gauze, tripod,
beaker and filter paper.
B. SAMPLES AND CHEMICALS USED
Aniline is the primary compound used to
acquire Acetanilide, which is our product.
Aniline, is an odorless, oily, poisonous
benzene derivative. Aniline is a toxic
substance that affects the oxygen inside the
blood, resulting the hemoglobin to transform
to methemoglubin that causes cyanosis. It
can also cause skin irritation when there is
skin contact. Acetanilide is the product of
this
Recrystallization.
Adding
Acetic
Anhydride with Aniline produces acetanilide.
It is used as an inhibitor in hydrogen
peroxide and is used to stabilize cellulose
ester varnishes. Acetanilide has analgesic
and antipyretic properties but is not that
usually used due to its side effects of
cyanosis just like Aniline.

Procedure

Figures

Choosing the Recrystallizing Solvent:

Place a corn grain amount of pure
acetanilide into each of the three test tubes.
To the first test tube, add 1mL of water.
Shake the test tube and place it in a warm
water (37-40C) for 1-5 minutes. Allow it to
cool. Record your observations. Do likewise
to the second and third test tubes, but this
time using ethanol and hexane.
1. Mix 2mL of aniline and 20mL of
distilled water in an Erlenmeyer
flask. Slowly add 3 mL of acetic
anhydride. Note any changes. Cool
in an ice bath to hasten
crystallization.
2. Filter through a wet filter paper. Dry
AT ROOM
TEMP.

DURING
HEATING

UPON
COOLING

Water

Insoluble

Soluble

Insoluble

Methanol

Soluble

Soluble

Soluble

Hexane

Insoluble

Insoluble

Insoluble

and weight the crude acetanilide.

Pour 20mL of the recrystallizing
solvent into the crude acetanilide.
Heat in a water bath until all the solid
dissolves.
4. If the solution is colored, remove it
from the bath and add activated
charcoal. Allow the filtrate to cool by
placing the receiver in a beaker
containing tap water. Collect the
crystals. Wash the crystals ice cold
distilled water. Press in-between
filter papers to dry. Place inside the
locker until the next meeting.
5. Weigh the pure acetanilide.
Determine the melting point of the
pure acetanilide.
3.

Tables

Fig. 1 Structural Formula of Aniline

Fig. 2 Structural
Formula of Acetanilide

Fig. 3 Dried and Weighed Pure

Acetanilide

Results and
Discussion

Table 1 shows the solubility of the solvents

added to pure acetanilide under different
temperatures. According to the results
tabulated, water is the proper solvent to be
used
for
the
recrystallization
of theacetanilide.
Acetylation is a reaction where in an acetyl
functional group is introduced into the
chemical compound. Aniline is acetylated by
warming mixture of aniline with acetic
anhydride, acetyl chloride or even glacial
acetic acid forming N-phenylacetamide,
which is commonly known acetanilide.
Acetanilide is an odorless, white flake solid
or crystalline powder (pure form); soluble in
hot water alcohol, ether, chloroform,
acetone, glycerol, and benzene. It has a
density of 1.219 g/mL. Acetylation of Aniline

is an exothermic reaction. Exothermic

reaction is the release of heat in the system.
Acetanilide is soluble in hot water and
insoluble in cold water. In order to hasten
the speed of recrystallization, ice bath is
done.
The recrystallization process of the crude
acetanilide involves the usage of activated
charcoal when the solution is colored.
Activated charcoal has a large surface area
per gram and can bind to large molecules of
the surface. It is a good adsorbent.
The hot solution should be filtered right
away to avoid crystallization. Washing of
crystals with cold recrystallizing solvent was
done to help reduce the amount of mother
liquor (solution that remains in crystals)

retained by the mass of crystals. Distilled

water was used for washing because it is
the recrystallizing solvent for acetanilide.
A fluted filter paper is used to allow rapid
filtration. The method of using a filter paper
forseparating charcoal from the filtrate is
called gravity filtration.

References:
Petrucci, Harwood, Herring et. al. General
chemistry: Principles & Modern
Applications, Ninth Ed. Upper Saddle River,
NJ: Pearson Education, Inc., 2007.
Pavia, D.L. Lampman, G.M. & Kriz, G.S.
(2005). Introduction to organic laboratory
techniques: A small scale approach (2nd ed.)
Pacific Grove, CA: Thomson-Brooks/Cole