is converted into acetic anhydride by atmospheric

oxidizing the liquid acetaldehyde in the presence

of metal acetate as the catalyst (oxidation
process). The ketene (or acetylene) created form
hot vapor of acetic acid is converted into acetic
anhydride by reacted with acetic acid (Ketene
process). The acyl groups (RCO) in organic
anhydrides favor wide range of organic synthesis.
They react with water to give carboxylic acids,
with alcohols or phenols to give esters, and with
ammonia and amines to give amides. Acetic
anhydride is used in the manufacture of cellulose
acetate having the application as a base for
magnetic tape and in the manufacture of textile
fibers. Also, it is heated with salicylic acid to
produce acetylsalicylic acid (aspirin). It is also
used in the manufacture of pigments, dyes,
cellulose and pesticides etc.

B. Procedure
1. Select the Recrystallizing Agent
A corn-grain amount of pure acetanilide was
placed into each of the three test tubes
containing water, ethanol and hexane, 1 mL of
each. Each test tube was shaken and was placed
in a warm water bath (37- 40oC) for 1-5 minutes.
It was cooled after. Observations were recorded.

2. Production of Crude Acetanilide

2 mL of aniline and 20 mL of distilled water
were mixed in an Erlenmeyer flask. Then, 3 mL of
acetic anhydride was slowly added. Changes were
noted, then it was cooled in an ice bath to hasten
crystallization. It was filtered through a wet filter
paper before drying it. Crude acetanilide was
obtained and weighed.

3. Recrystallization process

Figure 4. Structural Formula of Acetanilide

Acetanilide is an odorless, white flake solid or

crystalline powder (pure form); soluble in hot
water alcohol, ether, chloroform, acetone,
glycerol, and benzene; melting point 114 C and
boiling point 304 C; can undergo self-ignite at
545 C, but is otherwise stable under most
conditions. Acetanilide, which can be obtained by
acetylation of aniline, undergoes nitration at low
temperature and yields highly the para-nitro
products. Acetyl group can then be removed by
acid-catalyzed hydrolysis to yield paranitroaniline. Although the activating affection of
the amino group can be reduced, the acetyl
derivative remains an ortho/para-orientation and
activating substituent.

20 mL of the recrystallization solvent was

poured into the crude acetanilide then it was
heated in a water bath until the solid dissolved.
Activated charcoal is added if the solution is
colored, but the flask has to be removed from the
bath first before adding the activated charcoal.
The solution was quickly filtered while still hot
using a fluted filter paper. The filtrate was cooled
by placing the receiver in a beaker containing tap
water. The crystals were obtained. It was washed
with ice-cold distilled water before it was
pressed-in between two filter papers to dry. The
crystals produced were recrystallized pure
acetanilide. It was weighed before determining
the its melting point.

RESULTS AND DISCUSSIONS

The objectives of the experiment are as follow:

(1) to synthesize acetanilide by the acetylation of
aniline; (2) to purify crude acetanilide product by
recrystallization; and (3) to compute for the
percentage yield of pure acetanilide.

EXPERIMENTAL
A. Compounds tested (or Samples used)
The samples used to produce the crude
acetanilide were pure acetanilide, aniline and
acetic anhydride. The samples used in to select
the recrystallizing agent were pure acetanilide,
water, hexane and ethanol.

Figure 1. Melting point determination set-up

Melting point is determined to know the

temperature where a solid will change into its
liquid phase. Any impurities in a substance may
change its melting point.

Identifying the ideal recrystallizing solvent for

the compound is an important step for
recrystallization. The solubility test was
performed for the three given solvents, water,
ethanol and hexane. Pure acetanilide was added
to the three solvents. At room temperature, it
was insoluble in water and hexane, and soluble in
ethanol. The test tubes were then placed on a hot
water bath; the solvent became soluble in water
while it remained soluble in ethanol and insoluble
in hexane. After heating, the test tubes were
submerged on an ice bath. Upon cooling, the
solvent changed back to being insoluble in water
and the results for ethanol and hexane remained
the same.
Solvent

Room
During
temp.
heating
Water
Insoluble
Soluble
Ethanol
Soluble
Soluble
Hexane
Insoluble Insoluble
Table 1. Solubility of Pure Acetanilide
Solvents

Upon
cooling
Insoluble
Soluble
Insoluble
in Different

Table 1 shows the results of the solubility of

pure acetanilide in three different solvents.
Among the three solvent, the most appropriate
solvent to be used as the recrystallization solvent
is water since it exhibited the best results for
solubility of pure acetanilide.
Temperature
Pure acetanilide
112o C
Purified acetanilide
113o C
Table 2. Melting point of pure and purified acetanilide

Oil was used in the melting point determination

set-up because it has a higher boiling point than
water (>100OC). The table shows that the
purified acetanilide still had small traces of
impurities since there is a very slight difference
between their melting points.

The first major step in the recrystallization

process is dissolving the solute in the solvent.
After dissolving the acetanilide, the solution was
filtered using fluted filter paper while it is still hot
to prevent premature crystallization. It was then
cooled by placing the receiver in a beaker
containing tap water. The crystals were then
filtered and washed with distilled water, which is
the recrystallizing solvent of acetanilide. The
crystals were dried by pressing in-between the
filter paper then weighed. The weight of the
crystals collected was significantly reduced to
0.17g. The weight of pure acetanilide is small
compared to the 3.24g of crude acetanilide. This
also resulted to a small percentage yield.
COMPUTATIONS
Aniline in grams:
2mL Aniline x 1.0217g = 2.0434g
1mL
Acetic anhydride in grams:
3mL Acetic anhydride x 1.082g = 3.2460g
1mL
Computing for the limiting reagent:
2mL C6H5NH2 x 1.0217g x 1mole x 102.09g
1mL
93.13g 1mole
= 2.24g C4H6O3
3mL C4H6O3 x 1.082g x 1mole x 93.13g
1mL
102.09g 1mole
= 2.96g C6H5NH2
The limiting reagent is Aniline (C6H5NH2).
% Yield =

Actual Yield
Theoretical Yield

X 100

0.40g X 100 = 19.58%

2.0434g

The percentage yield is 19.58%. Only 19.58% of

pure acetanilide was formed after
recrystallization.
Figure 2. Recrystallization of Acetanilide

The acetylation of aniline and acetic anhydride

will yield the crude acetanilide but this contains
small amount of impurities that can affect the
weight of the pure acetanilide. During the hot
water bath, the impurities in the solution made
the solution appear colored. To decolorize the
solution, activated charcoal was added.

% Recovery =

Pure acetanilide X 100

Crude acetanilide
=

0.40g X 100 = 12.32%

3.2460g

The pure acetanilide is 12.32% of the weight of

crude acetanilide. This is the pure acetanilide

formed from the 2mL Aniline and 3mL Acetic

anhydride.

REFERENCES
[1]http://www.chm.uri.edu/bdeboef/chm292/rex
tallization.pdf
[2] Pastro, D. J., John, C. R., & Miller, M. S.
(1998). Experiment and Techniquesin Organic
Chemistry. New Jersey: Prentice Hall. Pg. 43-46
[3]http://www.chemicalland21.com/petrochemic
al/ANILINE.htm
[4]http://www.chemicalland21.com/petrochemic
al/ACETIC%20ANHYDRIDE.htm
[5]http://www.chemicalland21.com/lifescience/p
har/ACETANILIDE.htm

From book:
1. Pastro, D. J., John, C. R., & Miller, M. S.
(1998). Experiment and Techniquesin
Organic Chemistry. New Jersey: Prentice
Hall. Pg. 43-46

From the internet:

1. Recrystallization, retrieved October 11,
2015, from
http://www.chm.uri.edu/bdeboef/chm292
/rextallization.pdf
2. Aniline, retrieved October 11, 2015, from
http://www.chemicalland21.com/petroche
mical/ANILINE.htm
3. Acetic anhydride, retrieved October 11,
2015, from
http://www.chemicalland21.com/petroche
mical/ACETIC%20ANHYDRIDE.htm
4. Acetanilide, retrieved October 11, 2015,
from
http://www.chemicalland21.com/lifescienc
e/phar/ACETANILIDE.htm