Synthesis of Pure Acetanilide by the Acetylation of Aniline and Acetic Anhydride and its

Purification by the use of Recrystallization

Ajayi, Q., Alcuizar, M.K. , Alde, A.T., Amurao, R. A., Anisco, S.G., Arellano A.G.
2D-Pharmacy, Group No. 1, Department of Pharmacy, Faculty of Pharmacy, University of Santo
Tomas, Espaa Boulevard, 1015 Manila, Philippines

ABSTRACT
Recrystallization is a basic and widely used technique used for the purification of organic
solids through the difference of their solubility at different temperatures. It is also the process of
crystallizing solids by dissolving them in a hot solvent and then cooled at low temperature.
In this experiment, Crude acetanilide was formed through the acetylation of aniline
(C6H5NH2) and acetic anhydride (C4H6O3). Then by using a recrystallizing agent, namely water
(H2O), the crude acetanilide undergoes crystallization process. This process is done by dissolving
the crude acetanilide in a hot water until the solution is clear, but if there are coloration activated
charcoal should be added. After heating let it cool in an ice bath to produce pure acetanilide
[C6H5 NH(COCH3)] The weight of the crude acetanilide is 1.4g while the weight of pure
acetanilide is 1g. The percentage yield is 62.5%. The percent recovery is 71%

Introduction
Organic compounds, compounds made
up of Carbon (C), contain different
impurities. This impurities sometimes need
to be removed or purify for it can destroy
the experiment, thus people use different
purification methods to remove impurities.
For liquid solutions, Distillation is
commonly used, for it separates liquids
based on their boiling points. While on
solids, Sublimation or Recrystallization is
widely or commonly used. Sublimation is
the change of state of a solid to gas without
turning into liquid phase. While
Recrystallization is the process of purifying
organic solids base on their solubility rate. It
also is the process of heating solids and
cooling them to produce crystals.
In this experiment, we did crystallization
twice. In the first, we formed a crude
product. This means that there are some
impurities that is why a second
crystallization is needed to remove this

impurities and to get the pure substance

which is in the form of white crystals. The
formation of these crystals was because of
the difference in the solubility of the solid in
the solvent. In general, solutes or sometimes
compounds tend to be more soluble in
solvents at high temperature rather than cold
solvents.
In recrystallization the basis of
purification is solubility. Solubility is the
rate of a substance, solute, to be dissolved in
a solvent. That is why choosing the
crystallizing solvent was done first. The
purification process will happen if both the
desired substance and its impurities ahs the
same solubility when at boiling point.
The compounds that were involved were
Aniline, Acid Anhydride and Acetanilide.
Aniline, other known as amino benzene and
benzamine, is a clear or slightly yellow
liquid and is slightly soluble in water. It also
has different uses like synthesis of polymers,
fungicides and herbicides, and man-made

dyes. Its density is 1.0127g/mL and has a

molecular weight of 93.13 g/mol.
Acetic Anhydride, also known as Acetyl
Ether or Acetyl Oxide, is a colourless liquid
with a vinegar odour and when fused with
H2O will form Acetic Acid. It is used in the
synthesis of Cellulose acetate, naturally
occurring polymer, and can also be
combined to salicylic acid to form
acetylsalicylic acid or other known as
aspirin. Its density is 1.082 g/mL and has a
molecular weight of 102.09 g/moL. Its
boiling point is 140oC and its melting point
is at 73oC

Lastly is Acetanilide. Acetanilide is the

product formed in the experiment. It is a
odourless, white, crystalline powder. It is
soluble in hot water, alcohols, ethers,
chloroforms, acetones, glycerol and
benzene. It is used as an inhibitor and a
stabilizer; it is also used in the formation of
dyes, camphor and different pharmaceuticals
like penicillin and painkillers. Its boiling
point is 304oC and its melting point is
between 114-116oC.
The objectives of this experiment are to
synthesize acetanilide by the acetylation of
aniline and to purify the crude acetanilide
product by recrystallization process.

Methodology

Fig. 1 Heating Set-Up

1. Finding the right recrystallizing

agent.
A corn grain amount of acetanilide was
placed on three different test tubes. Distilled
water was then added on the first test tube,
Ethanol on the second and lastly Hexane on
the third. Then the test tubes were shook and
their solubility was noted. Then the test
tubes were heated on the water bath (37oC40oC) for 1-5 minutes. After heating, the
solubility is again noted. Then the test tubes
were cooled at room temperature. Then for
the last time the solubility was then again
noted. This process was done to determine
what the best recrystallizing agent is to form
pure acetanilide.

Fig. 2 Filtration Set-Up

2. Crystallization and Filtration of

Crude Acetanilide
In an Erlenmeyer flask, 2 mL of aniline and
20 mL of distilled water was combined and
3mL of acetic anhydride was slowly added
and then heated. Again the changes were
noted. Afterwards, the solution was cooled
and then filtered. The distillate was removed
and what remained was the filter paper were
residues of crude acetanilide was found. It
was then dried and weighed.

behaviour for the substance to be

crystallized. Compounds usually exhibits.
Solvent

Fig. 1 Ice Bath Set-Up

3. Recrystallization of Pure
Acetanilide Crystals
After drying, 20 mL of the recrystallizing
agent, namely water, was added to the crude
acetanilide. It was then heated in a hot plate
until the solids were dissolved. Then small
amounts of activated charcoal were added,
for the solution was colored. This was done
to remove the color for the activated
charcoal will absorb the color impurities.
Afterwards, the solution was filtered while
hot using a fluted filter paper, (a circular
piece of filter paper folded in an accordion
style and used to filter solid impurities from
a liquid during gravity filtration) Fluted
filter paper was used because it has an
increased filter area and because fluting
creates gaps between the filter paper and the
funnel. These gaps then provide channels for
the solvent to flow through there for
increasing the solvent flow. Then after
filtration, the distillate was cooled in an ice
bath and then the crystals were collected by
filtration again. Dry the residue then and
take note and weigh.

Results and Discussion

The very first step of this experiment is
the selection of proper recrystallizing
solvent. Recrystallizing solvent is a
substance use to show desired solubility

Room
During
Upon
Temp.
heating
cooling
Water
Insoluble Soluble
Insoluble
Ethanol Soluble, Soluble
Soluble
Hexane Insoluble Insoluble Insoluble
The solubility rates are first, At room
temperature insoluble and at the same time it
should be very soluble in heating or at high
temperatures. And again should be
insoluble at cooling or low temperatures.
Table 1. Solubility of Acetanilide
In this part, three solvents were used,
namely water, ethanol and hexane to find
which solvent would be suitable for the
experiment. As indicated in the table,
Hexane was insoluble in all temperatures
while Ethanol is soluble to all temperatures.
This proves that Ethanol and Hexane should
not be used as a recrystallizing solvent. On
the other hand, Distilled Water was insoluble
in room temperature and also upon cooling.
It is also non flammable and volatile. This
means that water is the recrystallizing agent
to be used in this experiment.
The combining of aniline and acetic
anyhydride produced crude acetanilide or
crystals with impurities with the help of
heating and cooling. Then the residue was
collected through the process of Filtration.
Although crystals were now produced,
we still need to remove its impurities so the
recrystallization process should be done
now. The crude acetanilide and the
recrystallizing solvent or water was then
cimbined and heated in a hot plate. Then
with constant stirring, wait for the crude
acetanilide to be dissolved. When the crude
acetanilide was dissolve, take a look at the
solution and if it has color then add a small
amount of activated charcoal. This was done
because Activated Charcoal is highly
absorbent carbin and also used as an

adsorbent and removal of impurities or

purification.
Then after heating, Filtration was then
used to remove the impurities. And then
after filtration, the solution was placed on an
ice bath and was cooled. Then the solution
will be filtered again to get the residue
which now contains Pure Acetanilide.
Weight of Crude
Actanilide
Weight of Pure
Acetanilide

References:
Books:
1. Brown, W., & Poon, T.
(2014). Introduction to organic
chemistry (5th ed.). Hoboken, NJ:
John Wiley & Sons, Inc.
2. Tung H.H. et. al. (2009)
Crystallization
of
Organic
Compounds:
An
Industrial
Perspective, Hoboken, NJ: John
Wiley & Sons, Inc.
3. Mullin, J.W. Crystallization.
Great Britain. Pitman, Press,
Bath

1.4g
1.0g

Table 2. Weight of the two Acetanilides

After the experiment, we must now
calculate the percentage yield, by using the
formula:
Actual Yield
Yield=
100
Theoretical Yield

Websites:

1.4 g

100=62.5
2.24 g
Based on the solution we could say that
the % yield can be easily computed. Then
the next to be solved is the %error of crude
acetanilide and pure acetanilide.
Recovery =

Recovery =

mass of pure acetanalide

100
mass of crude acetanalide
1. 0 g
100
1.4 g

% Recovery =71%

Conclusion
I therefore conclude that recrystallization
can make a substance purified but the
amount of substance may be decreased.

Recrystallization retrieved from

http://chemwiki.ucdavis.edu/Physical
_Chemistry/Physical_Properties_of_
Matter/Solutions_and_Mixtures/Case
_Studies/RECRYSTALLIZATION
Crystallization retrieved from
http://orgchem.colorado.edu/Techniq
ue/Procedures/Crystallization/Crystal
lization.html
Elements, Substances, Compounds
and Mixtures retrieved from
http://www.eschooltoday.com/scienc
e/elements-mixturescompounds/introduction-toelements-compounds-andmixtures.html