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Sharika Mae B. Espineli, Kamilah L. Fernando, Chester Bill C. Galapon

Jeana May C. Galinato and Jairish Keith Garcia
Group 4 2F Medical Technology Organic Chemistry Laboratory

Recrystallization is a common laboratory technique or method that is used to purify organic substances based on
solubility. In this experiment, crude acetanilide was produced by the acetylation of aniline and acetic anhydride. The
crude acetanilide was dissolved in the solvent using a heated water bath and immediately filtered. The filtrate was
cooled in an ice bath to hasten crystallization. Acetanilide underwent another crystallization process using the chosen
recrystallizing solvent which is water and filtered again to get the pure acetanilide. The data obtained was used to
compute for the percentage recovery of the pure acetanilide which is 29.17%.

Organic compounds that are solid at room
temperature are usually purified by
crystallization. [9] Recrystallization is a method
in which two crystallization processes were
performed. It is referred to as the second
crystallization. It depends on the difference of
solubility in a hot and in a cold solvent. [7]
Recrystallization of solids is a valuable
technique to master because it is one of the
methods used for purification of solids. Other
techniques for purifying solids include
sublimation, extraction, and chromatography.
Nevertheless, even when one of these alternative
methods of purification has been used, the solid
material thus isolated may still be recrystallized
to achieve the highest possible state of purity.
To understand the recrystallization process,
solubility behaviour must first be considered. It is
often stated that like dissolves like. More
correctly, it should be stated that, compounds
having similar structural features will be soluble
in one another. Some obvious structural
features that may affect solubility include polarity
and the ability to hydrogen bond. For known
compounds, it is useful to consider the structure
of the compound when choosing a
recrystallization solvent. Usually, however, the
structure of a compound may not be known so
the solvent must be chosen by carrying out
solubility tests. [8]
The objectives of the experiment are (1) to
synthesize acetanilide by the acetylation of
aniline, and (2) to purify crude acetanilide
product by recrystallization.
A. Compound tested (or Samples used)
The samples used in the experiment were pure
acetanilide, aniline and acetic anhydride.
Different solvents were also used in selecting the
recrystallizing solvent such as water, hexane and
Figure 1. Structural Formula of Aniline
Aniline is a colourless to brown, oily liquid with
an aromatic amine-like odour. It is stable,
incompatible with oxidizing agents, bases, acids,
iron and iron salts, zinc, aluminium. It is also
light sensitive and combustible. [3]
Figure 2. Structural Formula of Acetic
Acetic anhydride is a colourless liquid with a
strong, pungent, vinegar-like odour. It is
flammable and is also incompatible with strong
oxidizing agents, water, strong bases, and
alcohols. [2]
Figure 3. Structural Formula of Acetanilide
Acetanilide is a grey or white powder or flakes.
It is stable and it is combustible. It is
incompatible with strong oxidizing agents,
caustics and alkalis. [1]
B. Procedure
1. Determining the Recrystallizing Solvent
At the start of the experiment, a recrystallizing
solvent must be chosen. A pinch amount of pure
acetanilide was transferred into 3 separate test
tubes containing 3 mL distilled water, 3 mL
ethanol and 3 mL hexane each. Each of the test
tube was tested for the solubility of the pure
acetanilide in varying temperatures. First, the
solubility of the pure acetanilide in different
solvents was observed at room temperature.
Then, each test tube was heated in a water bath
(37-40C) for 1-5 minutes to check for the
solubility of the pure acetanilide in higher
temperature. After heating, the solution was
allowed to cool down to again check for the
solubility of the pure acetanilide.
2. Production of Crude Acetanilide
In an Erlenmeyer flask, 2 mL of aniline and 20
mL of distilled water was mixed and 3 mL of
acetic anhydride was slowly added after. The
Erlenmeyer flask containing the solution was then
cooled in an ice bath to hasten the crystallization
process. The solution was filtered through a wet
filter paper. The residue collected was the crude
acetanilide. The crude acetanilide was dried and
weighed after. [4]
3. Recrystallization Process
20 mL of the recrystallizing solvent was poured
into the crude acetanilide and heated after to
dissolve all of the solids formed. The solution was
filtered immediately while still hot using a fluted
filter paper. The filtrate collected was allowed to
cool in an ice bath to hasten crystallization. The
collected crystals were washed with distilled
water and were allowed to dry. The dried crystals
identified as pure acetanilide was weighed after.
Figure 4. Recrystallization Set-up

Recrystallization only works when a proper and
suitable recrystallizing solvent is used. The solute
must be relatively insoluble in the solvent at
room temperature, the solute should be much
more soluble in the solvent at high temperature
and insoluble upon cooling of the mixture. The
impurities present should be soluble in the
solvent at room temperature and insoluble in the
solvent at high temperature.
A table was created to show the obtained data
during the first part of the experiment which is
choosing the suitable recrystallizing solvent.
Table 1. Solubility of pure acetanilide in various
At room
Water Insoluble Soluble Insoluble
Ethanol Soluble Soluble Soluble
Hexane Insoluble Insoluble Insoluble

On table 1, it shows that there were three
solvents tested namely, water, ethanol and
hexane. Ethanol and hexane didnt show the
desired solubility behaviour of an ideal
recrystallizing solvent for acetanilide. Acetanilide
that will be placed in these solvents cannot
undergo recrystallization. However, water
showed the opposite behaviour exhibited by
ethanol and hexane. Pure acetanilide in water
was insoluble at room temperature, soluble
during heating and insoluble upon cooling, thus
showing the desired solubility behaviour of an
ideal recrystallizing solvent.
Table 2. Actual yield of crude and pure
acetanilide and the percentage recovery of pure
Weight of crude
2.4 g
Weight of pure
0.7 g
Percentage recovery 29.17%

Table 2 shows both the weight of the crude
acetanilide and the weight of the pure acetanilide
respectively. These values were already
subtracted to their pre-weighed filter papers
respectively. These values were also used to
compute for the percentage recovery of the pure
% recovery =

x 100
% recovery =

x 100
% recovery = 29.17%
To compute for the percentage recovery of the
pure acetanilide, the weight of the pure
acetanilide was divided by the weight of the
crude acetanilide, and multiplied by 100.

[1] Acetanilide, Retrieved September 24, 2013,
[2] Acetic anhydride, Retrieved September 24,
2013, from
[3] Aniline, Retrieved September 24, 2013, from
[4] Bathan, G. et. al. (2014). Laboratory Manual
in Organic Chemistry. Quezon City: C&E
[5] How to Perform a Recrystallization, Retrieved
September 23, 2014, from
[6] Recrystallization, Retrieved September 23,
2014, from
[7] Recrystallization, Retrieved September 23,
2014, from
[8] Recrystallization, Retrieved September 24,
2014, from
[9] Pastro, D.J., John C.R., & Miller, M.S. (1998).
Experiment and Techniques in Organic
Chemistry. New Jersey: Prentice Hall. Pg. 43-46
[10] Pavia, D.L., Lampman, G.M., Kriz, G.S., &
Engel, R.G. (1999). Organic Laboratory
Techniques: A Micro scale Approach (3
Harcourt College Publisher. Pg. 558-5