UNIVERSITY OF SANTO TOMAS

FACULTY OF PHARMACY
Organic Chemistry Laboratory
A.Y. 2018-2019

Experiment no. 4
Recrystallization of Acetanilide
Calugay, J.J., Caparas, C.E., Dador, A.S., De Guzman, D., & De Villa, G.K.

Abstract
To purify an organic compound, recrystallization is often used, wherein the
method of purification is based on the principle that: as the temperature increases, the
amount of solute that can be dissolved in a solvent increases as well.
In this experiment, to obtain pure acetanilide from crude acetanilide, the group
has conducted recrystallization. Corn-grain amount of acetanilide to be dissolved was
put in 3 different test tubes with three different solvents: water, methanol, and hexane,
respectively. Each test tube was then shaken and placed in a warm water bath for 1-3
minutes, then let cool. 2 mL of aniline and 20 mL of distilled water was mixed in an
Erlenmeyer flask. Then, 3 mL of acetic anhydride was slowly added. This mixture is
cooled with an ice bath which hastens the formation of crystals.
After this procedure, the mixture was filtered then dried, to finally obtain the
crude acetanilide. 20 mL of the recrystallizing solvent has been added to the crude
acetanilide and then heated on a water bath until the solid dissolves. Since the solution
was not completely colourless, activated charcoal was added. The mixture was filtered
while hot and the obtained filtrate was placed in an ice bath to cool. Crystals were
finally collected, then washed with distilled water. Weight and melting point of pure
acetanilide was determined. The crude acetanilide was found to be 2.35 grams in its
weight and yielded 72.97% of pure acetanilide which weighed 2.16 grams.

Introduction
There are always impurities when compound, purification is needed and
extracting compounds from natural recrystallization is a method to purify
products or after synthesis. These chemicals based on solubility, especially
impurities may include some since, not all solids can be purified by
combination of insoluble, soluble, and sublimation.
colored impurities. To obtain a pure
 Recrystallization is the process of
dissolving the solid to be crystallized in a
hot solvent, and then cooling the
solution slowly. It is important to choose
the appropriate solvent since the correct
solvent can yield high percentage
recovery and good purity. The
substance is expected to show an ideal
solubility behavior in a proper solvent in
which both the desired substance and
its impurities have similar solubilities
and boiling points. As a result, the
desired compound will crystallize after
dissolution when cooling, while the
impurities would not.
Crude acetanilide was first
obtained by acetylation of aniline. The
crude acetanilide contained impurities
such as acetic acid as well as unreacted
acetic anhydride. The said impurities of
the crude acetanilide were removed
using activated charcoal, filtration and
recrystallization.
The objectives of the experiment
are as follows:
(1)Synthesize acetanilide by the
acetylation of aniline
(2)Purify crude acetanilide
product by recrystallization
(3)Calculate percentage yield of
the recovered pure acetanilide
from the crude acetanilide

Methodology
The materials used in this
experiment were Erlenmeyer flask, test
tubes, bunsen burner, tripod, wire
gauze, beaker, filter paper, aniline,
hexane, acetic anhydride, and alcohol.
1. Choosing the Recrystallizing
Solvent
Fig 1. Testing and choosing the recrystallizing solvent
Corn-grain amount of pure
acetanilide was placed into each of the 2. Synthesis of Acetanilide
three test tubes. 1 mL of water was 2 mL of aniline and 20 mL of
added on the first test tube. It was distilled water was mixed in the
shaken and placed in a warm water Erlenmeyer flask. Then, 3 mL of acetic
bath (37-40℃) for 1-3 minutes. Then, it anhydride was slowly added. It was
was allowed to cool. Same procedure cooled to an ice bath for crystallization.
was done for the second and third test Then, the mixture was filtered through a
tube but instead of adding water, wet filter paper and was dried. Crude
ethanol and hexane were used acetanilide was then collected and
respectively. All observations were weighed.
recorded.
3. Purification by Recrystallization Results
20 mL of the recrystallizing The data collected during
solvent was poured into the crude experimentation included the weight of
acetanilide. It was heated in a water the crude acetanilide and weight of the
bath until all the solid dissolved. The pure acetanilide. The percentage (%)
solution was colored, therefore, yield was computed by first obtaining
activated charcoal was added. After the actual yield and the theoretical yield
which, the solution was filtered using a which was dictated by the limiting
fluted filter paper while it’s still hot. The reagent.
filtrate was placed in an ice bath to cool.
Crystals were collected and washed with Weight of the crude 2.35g
acetanilide
distilled water, then was pressed in-
between filter papers for it to dry. Weight of the pure 2.16g
Weight and melting point of pure acetanilide
acetanilide was determined. Table 1. Weight of crude and pure acetanilide

The solubility of the acetanilide

on various solvents which are: water,
ethanol, and hexane at three different
conditions (temperature) was also
identified. A criteria was followed in
order to find out the recrystallizing
solvent among the three.

Recrystallizing solvent criteria

At room During Upon

Fig 2. Filtering the crystals after using activated charcoal temperature Heating cooling

Insoluble Soluble Insoluble

Table 2. Ideal solubility of solute on various temperatures

Three conditions were followed

for every solvent; the solubility of the
acetanilide: at room temperature, when
heating, and upon cooling. And based
on the criteria, it was found out that
water is the most appropriate
recrystallizing solvent because the
solute was insoluble at room
temperature, dissolved when heated,
Fig 3. Pressing the crystals dry then became insoluble when cooled.
 At room During Upon grain of equal amount. Each of the test
temperature heating cooling tubes will have 1 mL of water, ethanol
and hexane respectively. The solvent
water Insoluble Soluble Insoluble
must be insoluble at room temperature
ethanol Soluble Soluble Soluble and in an ice bath, and soluble when
exposed to hot water to identify
hexane Insoluble Insoluble Insoluble whether it could be a recrystallizing
Table 3. Solubility results of the solute on three solvent at
solvent.
different conditions

The percentage yield and percent Once the recrystallizing solvent

recovery was computed respectively has been identified, 20mL distilled water
using the equations: will be added to 2 mL of aniline and was
subjected to an ice bath for
𝑨𝒄𝒕𝒖𝒂𝒍 𝒚𝒊𝒆𝒍𝒅
%yield= x 100% crystallization. The crude acetanilide
𝑻𝒉𝒆𝒐𝒓𝒆𝒕𝒊𝒄𝒂𝒍 𝒚𝒊𝒆𝒍𝒅
was collected being filtered and dried.
pure extract
%recovery= x 100% After which, 20 mL of the recrystallizing
𝑐𝑟𝑢𝑑𝑒 𝑒𝑥𝑡𝑟𝑎𝑐𝑡
agent was used to dissolve crude
Computations: acetanilide. Activated charcoal was
Theoretical Yield added to remove the impurities of the
solution. The crystals collected were
1.02g/mL aniline mol aniline
2mL Aniline x
mL aniline
x
93g aniline
x washed with distilled water and dried by
1mol acetanilide 135g acetanilide pressing them into filter papers. Crude
x = 2.96g
1 mol aniline 1 mol acetanilide acetanilide weighed 2.35g before
3.0mL Acetic anhydride x
1.08g/mL acet anhy
x
recrystallization. After the process, the
mL acet anhy pure acetanilide weighed 2.16g.
mol acet anh 1mol acetanilide 135g acetanilide
x x =
102g acet anh 1 mol acet anhy 1 mol acetanilide
4.29 g Acetanilide
The Limiting Reagent is the
Aniline. Thus, the theoretical yield is
2.96g Acetanilide.
2.16𝑔
%yield= x 100% = 72.97%
2.96𝑔

2.16g
%recovery= x 100% = 91.91%
2.35g

Discussions
As seen clearly from the
experiment, the first part is done to
identify the recrystallizing solvent. In the Fig 4. Pure acetanilide
first part of the experiment there were 3
test tubes containing a pinch of corn-
 Results showed that the %yield
was 72.97% and the recovery
percentage was 91.91%. It tells that the
2.16g pure extract is within the range of
the theoretical yield computed based on
the limiting reagent. The
experimentation also shows the
relationship between the temperature
and solubility of the solute and solvent.
That a solute must be soluble on hot
temperature and insoluble on low
temperature.
References
Bathan, et al. (2018) Experiment 3
Sublimation and Melting point.
Laboratory Manual in Organic
Chemistry (revised edition).

Britannica Online (2012). Aniline

(Chemical compound). Retrieved
from
http://www.britannica.com/EBche
cked/topic/25473/aniline.
Retrieved on March 24, 2019.

Dalmacio, E.., et al. (2012) Experiment

4: Recrystallization of Acetanilide.
Organic Chemistry Laboratory.

Hammond, M. (2017). Recrystallization.