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Purification of Acetanilide by Means of Recrystallization

Miguel, K.D., Moron, R.S.S., Pazon, A.D., Ramirez, C.V., Raquepo, T.M.R., Razon, D.N.A.Jr.
2B-PH, Group No. 6, Department of Pharmacy, Faculty of Pharmacy,
University of Santo Tomas, Espaa Boulevard, 1015 Manila, Philippines
Recrystallization is a widely used technique and is an important technique in purifying organic
compounds. It involves dissolving a material to be purified (the solute) in an appropriate hot
solvent to yield a solution. As the solvent cools, the solution becomes saturated with respect to
the solute (saturation level), which then recrystallizes. As the perfectly regular array of crystal is
formed, impurities are excluded, and the crystal is thus a pure substance. [1] A suitable solvent in
purifying solid compounds carries the characteristic of allowing the compound (to be purified) to
be very soluble to the solvent at its boiling point, and only sparingly soluble at its room
temperature.[2] This report presents the procedure on how to perform recrystallization: choosing
the suitable solvent for purification, acetylation of aniline with acetic anhydride to synthesize
crude acetanilide, purification of crude acetanilide, and gathering the crystals obtained from the
pure acetanilide. It also contains the equations and calculations used in this experiment. The
percentage yield calculated from the experiment is 77.70%. The actual yield is 2.3g. This is the
pure acetanilide obtained from aniline and acetic anhydride.

Various purification methods can be
done in natural organic compounds since
these compounds, whether solid or liquid,
contain impurities. The method of
purification is determined by different
physical and chemical characteristics of a
certain compound. [3] For liquids,
evaporation, and distillation are examples of
purification methods. Distillation is the most
commonly used process which is primarily
based on the boiling points of the
compounds used. For solids, purification can
be done through sublimation, adsorption,
and recrystallization. Organic compounds
purified through sublimation pass directly
into the vapour phase without passing
through the liquid phase. Organic
compounds that lack this property may be
purified through recrystallization, which is

the simplest and most commonly used

process. [4]
A pure crystalline substance is
composed of a three-dimensional array of
molecules held together primarily of London
forces. These attractive forces are fairly
weak; most organic solids melt in
temperatures between 22C and 250C. An
impure organic solid will not have a welldefined crystal lattice because impurities do
not allow the crystalline structure to form.
The goal of recrystallization is to remove
impurities from a solid to allow a perfect
crystal lattice to grow. [5] The main factor
that affects crystallization is solubility. It is
ideal to identify a suitable recrystallizing
solvent prior to performing purification
through the recrystallization process. It is
often stated that like dissolves like. More
correctly, it should be stated that,
Compound having similar structural
features will be soluble in one another. An

ideal solvent shall have structural features

similar to the structures of impurities in
order to obtain the pure crystals [6]
The Objectives of this experiment are:
1) to synthesize acetanilide by the
acetylation of aniline, and 2) to purify crude
acetanilide product by recrystallization.
Apparatus & Reagents Used
The apparatus and materials used in
this experiment were Erlenmeyer flask, test
tubes, Bunsen burner, tripod, wire gauze,
beaker, and a fluted filter paper. The
reagents used were hexane, acetic
anhydride, and ethanol.
Choosing the Recrystallizing Solvent
In this experiment, the first
step was to choose a suitable solvent that
will aid in the purification of acetanilide.
This was done by placing a corn-grain
amount of pure acetanilide into each of the
three test tubes. One milliliters of water was
placed on the first test tube. It was shaken
and placed in a warm water bath having a
temperature of about 40C for 5 minutes.
After the warm water bath, it was allowed to
cool. This was also done to the second and
third test tube but instead of water, ethanol
and hexane were used respectively. Take
note that both ethanol and hexane are
flammable and volatile. The solubility of the
pure acetanilide in the different solvents was
noted at varying temperatures. This was
done to determine the appropriate and the
best solvent that will yield pure acetanilide
through the acetylation of aniline and acetic
Acetylation of Aniline by Acetic Anhydride

In the preparation of acetanilide,

two milliliters of aniline and twenty
milliliters of water were mixed in an
Erlenmeyer flask. Three milliliters of acetic
anhydride was slowly added into the flask.
Obtaining Crude Acetanilide
The mixture was then cooled by
running a cold water on the outside of the
flask since no ice bath were available. This
was done to hasten the crystallization. When
the crystals were fully formed, the solution
was filtered through a wet filter paper. The
crystals were kept in the locker to dry for
several days, this served as the crude
acetanilide. The weight of the crude
acetanilide was noted.
Purification of Crude Acetanilide
The next step was to pour twenty
milliliters of water (which served as the
recrystallizing agent) to the crude
acetanilide. It was heated in a water bath
until the entire solid dissolved, or until it
gave a clear solution. After that, the solution
was quickly filtered while still hot using a
fluted filter paper. The filtrate was allowed
to cool by placing the receiver in a vessel
containing ice. The crystals were collected.
And the crystals were then washed with icecold distilled water. It was placed again in
the locker to dry, but this time it was already
pure acetanilide. The dry and pure
acetanilide was later on weighed.
Results and Discussions
Choosing the Recrystallizing Solvent
In determining the most suitable
recrystallizing solvent, some factors are
considered. The compound should be
insoluble to the solvent at room temperature.
While heating, the compound should be very

soluble, and upon cooling, it shall be

insoluble. On the contrary, the unwanted
impurities should be soluble at room
temperature or insoluble during heating.
Table 1 shows the solubility of acetanilide in
various solvents. Among the three solvents,
water was chosen to be the recrystallizing
solvent since it has the characteristics of an
ideal solvent based on the data gathered. The
applied amount of heat energy associated
with a given temperature in a given system
is the heat capacity.[7] It should not go
beyond the melting point of the substance to
be crystallized. If the boiling point of the
solvent is high, the solid may melt in the
solvent rather than dissolve. In such case,
the solid may oil out as shown in Figure 1.
Oiling occurs when the solid substance
melts and forms a liquid that is insoluble in
the solvent. When cooling, the liquid refuses
to crystallize; rather, it becomes a super
cooled liquid, or oil. Oils may solidify if the
temperature is lowered, yet will not
crystallize. In addition, volatility of the
solvent is a factor in selecting the correct
recrystallizing solvent. The solvent should
be volatile enough to be easily removed
from the solution after crystallization.
Volatile solvents having low boiling point is
preferable. The chemical reactivity of
recrystallizing solvent should be low. It
should neither decompose nor oxidize the
desired substance. The solvent should not
react with the compound to be purified.
Thus, the desired substance may be
contaminated with impurities.[8]
At room



Insoluble Insoluble Insoluble
Table 1 Solubility of acetanilide in
various solvents


Aniline by

Some properties of aniline,

acetic anhydride and acetanilide are
presented in Table 2. The molecular
structure formula of Aniline is seen on
Figure 2 and that of Acetic Anhydride is
seen on Figure 3. The molecular structure
formula of Acetanilide can be seen on
Figure 1 An example of a solution that has
oiled out
Figure 4. The crude acetanilide was obtained
by the acetylation of aniline. Acetylation
describes a reaction that introduces acetyl
functional group into a chemical compound.
[9] Namely, it is the substitution of an acetyl
group for an active hydrogen atom. A
reaction involving the replacement of the
hydrogen atom of a hydroxyl group with an
(CH3 CO)
specific ester,
acetate. Acetic
anhydride is commonly used as an
acetylating agent reacting with free hydroxyl
groups. [10] The crude acetanilide obtained
in this experiment was 4 grams in its weight.
This acetanilide still has impurities in it that
is why purification is still needed to be done.

Figure 4 The Molecular Structure Formula

of Acetanilide

Table 2 Some properties of Acetanilide,

Aniline & Acetic Anhydride

Figure 2 The Molecular Structure

Formula of Aniline

Figure 3 The Molecular Structure

Formula of Acetic Anhydride

Purification of Crude



In heating the solvent, it was noted

that the compound acetanilide may dissolve
in the solvent and insoluble impurities are
present in the sample. If in case that the
solution is colored, addition of activated
charcoal, to bind high molecular weight,
colored impurities is necessary. [11] This is
done to obtain the desired colorless solution
if heating is not enough. This step was not
used in the experiment since a colorless
solution was already obtained. Hot gravity
filtration was used in this experiment. This
type of filtration is used to separate
insoluble impurities from a hot solution. The
main problem in hot filtration is that the hot
solution cools a little before it runs through
the filter. This means that some
crystallization can take place in the filter .
That is why the solution was quickly
filtered. In filtering, a fluted filter paper was
used. Fluted filter paper is often better for
gravity filtration with organic solvents.[12]
A diagram of how to fold fluted filter paper
is shown below on Figure 5.
recrystallization of the crude acetanilide.
From the 4 grams of crude acetanilide, 2.3
grams of pure acetanilide was gathered. In
the computation of the theoretical yield,
aniline was the limiting reagent.
Significance of Cooling

Figure 5 A Diagram on How to Fold a Fluted Filter Paper

The rate of cooling determines the

size of the crystals. Slow cooling tends to
favor fewer and larger crystals, fast cooling
tends to favor more and smaller crystals.
Very large crystals are to be avoided since
they often occlude the solvent and its
dissolved impurities. Very small crystals are
undesirable because it is difficult to wash
them free of the solvent and the soluble
impurities, and it takes longer to dry them.
[8] Sometimes it will be possible to hurry
the cooling without getting overly small
crystals by swirling the flask in a beaker of
water at room temperature, or even by
placing the flask directly in an ice bath as
what was done in this experiment.

the sample substances. Micromelting point

is the strapping of capillary tubes on the tip
of the thermometer and then immersed into
an oil bath. In this experiment, oil can be
used rather than the usual water because it
has a higher boiling point than water, and
it also does not evaporate easily when
heated at a high temperature. The standard
melting point of acetanilide is 113-115C.
Once the determined melting point is same
as the standard, the obtained crystals may
be deemed as pure. A value obtained that is
not the same as the standard may be
subjected as impure.
Equations & Calculations Involved

Chemical equation for acetanilide:

Calculation of aniline (in grams):

Calculation of acetic anhydride (in grams):

Melting Point Determination of Pure

Melting point determination was not
done in this experiment but it is necessary to
determine whether a pure acetanilide was
obtained from the experiment or not.
Melting point is the temperature at which
the solid and liquid phase or forms of a
substance exist in equilibrium. Micromelting
point is one method that can be used in this
experiment to determine the melting point of

Determining the limiting reagent:

The limiting reagent (or limiting reactant) in
a chemical reaction is the substance which is

totally consumed when the chemical

reaction is complete. The amount of product
formed is limited by this reagent since the
reaction cannot proceed further without it.
Therefore, the limiting reagent is aniline
since 2.96g of CHNO was needed to
make 3mL of C4H6O3. The theoretical yield
is equal to the limiting reagent.
Percentage Yield & Percentage Recovery
Percantage Yield=

2.30 g
x 100
2.96 g


Percentage Recovery=

2.3 g
x 100
4.0 g


The percentage yield was

77.70%. This value is quite close to the
theoretical value expected to complete the
perfectly efficient reaction. There may be
some human errors encountered during the
experiment that might have contributed to
this value. Some human errors were as
follows: not being able to collect all of the
pure crystals, or it may have been collected
yet some may have been taken away by the
wind, or maybe the crystals werent weighed
The percentage recovery is used in
cases where no chemical reaction is taking
place, as in purification of a sample. It is
calculated as follows: first, by dividing the
weight of the pure acetanilide by the weight

of the crude acetanilide and then multiplying

by a hundred percent. The percentage
recovery was 57.50%

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New Jersey: John Wiley & Sons.
[4] Karger, B. L. (2014, April 4). Separation and Purification. Retrieved October 5, 2015, from
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Microscale.Washinton, DC: Charles Hartford.
[6] Barnes,M. (2014). Recrystallization. Retrieved October 6, 2015, from Chem Mass:
[7] Mullin, J. W. (2001). Crystallization (4th edition) .London, England: Butterworth & Co.
[8] Berry, J. (2004, September). UW Madison. Retrieved from Chem Wisk:
[9] Saunders. (2007). Dorland's Medical Dictionary for Health Consumers. Elsevier, Inc.
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[10] Pahlavan, D. (n.d.). Experiment 5- Preparation of Acetanilide. Retrieved from Southwest
[11] Athabasca University. (n.d.). Retrieved from science.pc:
[12] Organic Chemistry at CU Boulder. (2015, August 31). Retrieved from