RECRYSTALLIZATION

Sophia Allison Dones, Angelica Gallardo, Lyka Alexandrea Gomez, Mikaela Rose Gutierrez,
Heather Eena Lim
Group #4
1C-Biochemistry

ABSTRACT

Recrystallization is a widely used technique for purifying organic solids. It is also a

process where a solid to be crystallized is dissolved in a hot solvent and is slowly cooled in a
solution. The objectives of this experiment was to synthesize acetanilide and to purify crude
acetanilide product by means of recrystallization. In this experiment, acetanilide was used as the
pure organic compound. The crude acetanilide underwent crystallization using water as solvent.
In the crystallization process, the crude acetanilide was placed in a hot water bath and was
cooled in an ice bath which produced the formation of crystals of pure acetanilide. The
percentage yield obtained from this experiment is 12.97% The results showed that water is the
proper recrystallizing agent for acetanilide.

INTRODUCTION appear and then it will grow layer by layer

Organic compounds acquired from
natural resources contain impurities.
Different purification methods can be used
to remove these impurities. The solubility
behavior of these compounds must be
considered. Distillation is usually used as a
purification method for liquids. For solids,
either recrystallization or sublimation is
used as a purification method.
Recrystallization is a primary method for
purifying an impure compound. The amount
of solute varies directly with temperature,
once the temperature increases, the amount
of solute that can dissolve in a solvent also
increases. [1] Only very pure compounds
can be produced by recrystallization when
the solution is heated and the dissolved solid
has decreased its solubility it will separate
from the solution then a small seed will
until it forms a crystal. [2] In this
experiment, acetanilide is used to be
purified, it is a white solid organic
compound usually used in organic synthesis.
It can be acquired by the acetylation of
aniline.
The objectives of this experiment
was to synthesize acetanilide by the
acetylation of aniline and to be able to purify
crude acetanilide by recrystallization.
MATERIALS AND METHODS
The experiment on recrystallization
includes the following materials;
Erlenmeyer flask, thermometer, filter paper,
hexane, ethanol, crude acetanilide, activated
charcoal, capillary tubes, test tubes,
perforated filter paper and a beaker. A
procedure was done to determine the
recrystallizing solvent; A corn grain amount
of acetanilide was placed into three test
tubes. The first test tube had one milliliter of
water added to it, the second had one
milliliter of ethanol added to it and the third
had one milliliter of hexane added to it.
These three test tubes were tested at
different temperatures, room temperature
and high temperature which ranged from
37°C to 40°C and at cold temperature. In an
Erlenmeyer flask, two millimeters of aniline
and twenty millimeters of distilled water
was mixed together while three millimeters
of acetic anhydride was added slowly. The
mixture was cooled under cold running
water to hasten the crystallization.
Figure 1. Filtration set-up
Figure 1. shows the set-up of filtration. After
having it cooled, it was then filtered through
a wet filter paper which yielded crude
acetanilide and was collected. The crude
was placed aside until it was fully dry then
weighed and placed in an Erlenmeyer flask.
Twenty millimeters of recrystallizing
solvent was poured into the flask and was
heated in a water bath until the solids were
completely dissolved. Color was observed in
the solution after it was dissolved then
activated charcoal was added to the solution.
The solution was filtered while it was hot
and the filtrate was cooled. Crystals were
collected after cooling and was rinsed with
water and dried.
The next procedure of the experiment for the
melting point determination had a different
set-up. The collected crystals were ground
into a fine powder and was placed inside a
capillary tube with a sealed end and was
pressed until it was well-packed with three
to five millimeters (3-5 mm) of the
sublimate. The closed end of a capillary tube
was aligned with the mercury bulb of the
thermometer and was taped together as seen
in Figure 2.
 Figure 2. Capillary set-up experiment’s data, water is the most suitable
The capillary tube was then immersed in an compound for recrystallization of pure
oil bath under heat and was stirred acetanilide because it manifests all the ideal
constantly while the temperature at which properties for recrystallization solvent.
the sublimate starts to melt until it was
completely melted was recorded. In the experiment, a hot filtration
was used to remove the impurities from the
RESULTS AND DISCUSSION compound by pouring a few milliliters of
recrystallizing solvent through a funnel with
Weight of crude acetanilide:​ 2.054 g the aid of a filter paper which produced
some colored impurities. Activated charcoal
Table 1. Solubility of pure acetanilide in was then added to adsorb the impurities.
various solvents After decoloration, the hot filtrate was set
At room During Upon aside and as the solution cools, crystals
temperat heating cooling began to form.
ure
Weight of pure acetanilide: ​0.2665 g
Water insoluble soluble insoluble
CALCULATIONS
Ethanol soluble insoluble insoluble % yield: (Actual yield)/(Theoretical yield)
x 100
Hexane insoluble insoluble insoluble
% yield: (0.2665)/(2.054) x 100
% yield: ​12.97%
Table 1 shows the solubility of
acetanilide using different solvents namely Percentage yield describes the
water, ethanol and hexane. The pure percent ratio of the obtained experimental
acetanilide in water at room temperature was yield to the theoretical yield. The a​mounts of
found out to be insoluble, soluble when products calculated from the complete
heated and insoluble when cooled. On the reaction of the limiting reagent are called
other hand, ethanol is soluble at a room theoretical yield, whereas the amount
temperature but gave an insoluble result actually produced of a product is the actual
both during heating and cooling. Lastly, yield. To calculate for the percentage yield,
hexane is insoluble at the three different the actual yield should be divided by the
given temperatures. A good solvent for theoretical yield and then multiply it by 100
recrystallization is the compound that is to get the percentage (“Recrystallization,”
insoluble at low temperatures but soluble in 2019). The percentage yield calculated is
higher temperatures 12.97%. A low percentage yield may have
(“Preparation/Recrystallization of been caused due to some impurities that
Acetanilide,” n.d.) Based on the were not totally removed, or may caused by
random errors. Percentage yield is helpful
because it indicates whether the experiment
done is efficient and correct.
Melting point of the recrystallized
acetanilide: ​100℃
Melting point is the temperature at
which a substance melts. Another method
to determine the identity and purity of an
unknown compound is by determining its
melting point. After the filtration, the
solution was cooled and and the purified
samples were collected and dried. The end
of capillary tube was put into the
compound so the crystals can fill the open
end of the melting point capillary.
Afterwards, the capillary tube was
immersed in the oil bath. In this
experiment, oil bath is more preferred
instead of a water bath because oil has a
higher boiling point and it does not
evaporate easily compared to water
because it is more volatile. Comparing the
experimental data with the standard
melting point of acetanilide which is
114.3°C, the pure acetanilide has still some
impurities left because it started to melt at
a lower temperature at 100°C. Based on
the result, it shows that the melting point
of the standard acetanilide and the pure
acetanilide has a difference of 14.3°C. The
greater the difference, the more impurities.
A pure substance has a fixed melting point
while an impure substance melts over a
wide range of temperatures and at a lower
temperature than the pure substance
(“​Recrystallization of Benzoic Acid and
Determination of its Melting Point,” 2019)​.
Since the sublimate started to melt at a
lower temperature than of the pure
substance’s melting point, this implies that
there are still some impurities left. The
said impurities blocks the formation and
create irregularities which makes the
intermolecular bond weaker. Moreover,
this results to decrease the heat energy that
breaks the bond making the temperature of
the impure substance lower.
Percentage error
% error: 100℃ - 114.3℃/114.3℃ x 100
% error: ​ 12.51%
The percentage error was
computed, having a value of 12.51%
implies that there are factors that may
have caused errors in the experiment,
such as systematic errors. Calculating the
percentage error is necessary for one to
know if the experiment is successful or
not. Small percentage errors mean that
the result of the experiment is close to
the accepted value.
REFERENCES
Chang, R. (2010). ​Chemistry​. Boston:
McGraw-Hill.
Preparation/Recrystallization of Acetanilide.
(n.d.). Retrieved from
http://www.mendelset.com/articles/680/prep
aration-recrystallization-acetanilide
Recrystallization. (2019) Retrieved from
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_Maps/Supplemental_Modules_(Physical_a
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ties_of_Matter/Solutions_and_Mixtures/Cas
e_Studies/RECRYSTALLIZATION

Recrystallization of Benzoic Acid and

Determination of its Melting Point. (2019).
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Theoretical and Actual Yields. (2019).

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