CHM142L Organic Chemistry 1 Laboratory

3rd Quarter SY 2014-2015

Recrystallization
Miranda, Marilyn1, Ayson, Jose Paolo, L2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; 2Student, CH142L/A31, School of Chemical Engineering,
Chemistry and Biotechnology, Mapua Institute of Technology
1

ABSTRACT
The objectives of this experiment are to identify the appropriate solvent for the recrystallization technique and to use the
recrystallization technique in purifying a solid sample. Recrystallization is a purification process used to remove impurities
from organic compounds that are solids at room temperature. The first part of the experiment is the determination of suitable
solvents of given substances (acetamide, acetanilide, aspirin, benzoic acid, naphthalene, and sucrose). In selecting
appropriate solvent, an ideal recrystallizing solvent: must dissolved the compound in high temperatures, must not dissolved
the compound in low temperatures, have different solubilities for the compound and the impurities, have a boiling point below
the melting point of the compound and must have an abundant quantity of crystals recoverable from the cool solvent. The last
part was a performed recrystallization of a impure sample of crude acetanilide. In performing the purification of an impure
substance by recrystallization, there are conditions that need to be followed like dissolving the substance in the least amount
of solvent to prevent recovery loss. Also, equipments must be considered like the fluted filter paper must be used rather than a
regular filter paper and a stemless funnel must be used to prevent blocking. The understanding of recrystallization process
and techniques were observed and learned in this experiment.
Keywords: recrystallization, purification, ideal recrystallization solvent, vacuum filtration, hot gravity filtration, activated carbon

INTRODUCTION
Differential solubility is one of the most commonly used
physical properties of solids in an appropriate solvent. It
is defined as differences in the amount of solid that can
be dissolved in an appropriate solvent as affected by
variations in temperature. Recrystallization is a process
that determines the purity of a compound or a solid
substance.
Impurities often contaminate organic compounds that
have been synthesized in the laboratory or isolated from
natural sources. Recrystallization is a purification process
used to remove impurities from organic compounds that
are solids at room temperature. This process is based on
the premise that the solubility of a compound in a solvent
increases with temperature. Conversely, the solubility of
the compound decreases as the solution cools, and thats
when the crystals are formed.
Pure compounds can be produced by recrystallization.
As a heated solution of the desired compound cools, a
small, pure seed crystal of the compound forms in the
solution. Layer by layer, additional molecules attach to
this crystal, forming a growing crystal lattice. Molecules in
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the crystal have greater affinity to the other molecules of

the same kind than any impurities present in the solution.
MATERIALS AND METHOD
The first part of the experiment is to determine what are
the appropriate solvent for the following substances;
acetamide, acetanilide, aspirin, benzoic acid,
naphthalene, and sucrose. The substances was test in
four different solvents namely water, ethanol, benzene
and Ethyl acetate. There are two trials per substance in
solvent for observing the reaction in hot and cold solvent.
In the second part of the experiment, we are obliged to
perform the recrystallization of an impure acetanilide. 100
ml of water was heated and approximately 3.50 g of
crude acetanilide was weighed. It was then dissolved 30
ml of water, with the use of the hot plate the mixture was
slightly boiled. 2 ml of water from the pre-heated 100 ml
water was added to the mixture when it starts to boil. The
addition of 2 ml of water was repeated with stirring until
the white solid was completely dissolved. Do not stop the
addition of water since the white solid may solidify when
the volume of water in the mixture decreases due to
evaporation. The total volume of the mixture did not
exceed 70 ml since the solubility is 4.30 g/ 100 ml. When
the white solids are completely dissolved, it was poured

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3rd Quarter SY 2014-2015

in the hot gravity filtration set-up through the fluted filter

paper situated in the stemless glass funnel. The filtrate
obtained was colorless and it was then cool downed to
room temperature and was placed in an ice bath with
stirring until crystallization is complete. After
crystallization is complete, the solution was vacuumed
filtered and dried in an oven for 30 minutes to 45 minutes.
It was then weighed for the computation of percentage
recovery.

Naphthalene

Water

Sucrose

Ethanol

These are the appropriate solvents for each of the

substance since the solvents achieved the characteristics
or conditions to be an ideal recrystallization solvent.
Table 3: Recrystallization of Impure Acetanilide.

RESULT
Table 1: Determination of Appropriate Solvent

COMPOUND

Water

Ethanol

Benzene

Ethyl
Acetate

Acetamide

Acetanilide

Aspirin

Benzoic Acid

Naphthalene

Sucrose

.S = Soluble; I= Insoluble

Weight of crude acetanilide

in grams

3.50

Weight of the filter paper in

grams

1.05

Weight of the
acetanilide in grams

0.91

pure

Volume of water used in ml

32

Melting point of pure

acetanilide in degrees
celcuis

99 101

Percentage Recovery

40.90%

The computed percentage recovery is small; meaning

only small amount of pure substance was acquired.
Table 4: Observations

Table 2: Appropriate Solvents

COMPOUND

Solvent Appropriate
Recrystallization

Acetamide

Benzene

Acetanilide

Water

Aspirin

Benzene

Benzoic Acid

Water

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for

Step

Observation

Boiling of crude acetanilide

The crude acetanilide was

dissolved using stirring rod,
it has black and white
particles, and it was heated
to maintain the required
temperature so that white
particles are dissolved and
black remains.

Addition
carbon

of

activated The liquid is clear/

colorless. Addition of

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3rd Quarter SY 2014-2015

activated carbon was not

needed.
Hot gravity filtration

The filtrate is a clear liquid

that was dissociated form
residue which has black
particles left.

Cooling in an ice bath

The filtrate was cooled

down to room temperature.
Some solids were formed
that can be filtered.

Vacuum filtration

Upon using the vacuum

filtration, white solids were
recovered and the liquid
was separated.

DISCUSSION
In
recrystallization,
selecting
an
appropriate
recrystallizing solvent to use is probably the most difficult
step of recrystallization. The primary consideration when
choosing a recrystallizing solvent is the extent to which
the compound and impurities are soluble in the solvent at
high and low temperatures. If possible, the compound to
be recrystallized should be very soluble in the chosen
solvent at elevated temperatures, but almost insoluble in
the cold solvent. Also, impurities should be insoluble at all
temperatures so they can be filtered out of the hot
solution. Acetamide and Aspirin are both have benzene
as their appropriate recrystallization solvent since
benzene satisfies one of the conditions that is both
Acetamide and Aspirin are both insoluble at cold benzene
and soluble in hot benzene. In selecting appropriate
solvent, an ideal recrystallizing solvent: must dissolved
the compound in high temperatures, must not dissolved
the compound in low temperatures, have different
solubilities for the compound and the impurities, have a
boiling point below the melting point of the compound and
must have an abundant quantity of crystals recoverable
from the cool solvent. The boiling point of the
recrystallization solvent should be lower than the melting
point of the compound to be recrystallized. If the solvents
boiling point is higher than the compounds melting point
the compound is deposited as oil, and not as crystals.

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These conditions are necessary to acquire the pure

substance without any complexity and have the desired
results.
In performing recrystallization, the minimum amount of
solvent is used to dissolve the solute because if too much
solvent is used, the recovery of sample will be
decreased. Fluted filter is used instead a regular filter
paper because it can maximize the rate at which the
solvent may flow through the filter paper. This will
increase the surface area of the air flown into the flask
along the sides to permit rapid pressure equalization. A
stemless funnel is used because crystals can form in the
cool stem of a long-stem funnel and clog it. The solution
was allowed to cool in room temperature because the
slower you cool, the slower the crystals will grow. Slowly
grown crystals grow larger, more regularly, and trap fewer
impurities. An advantage of suction filtration or vacuum
filtration is that the solution is more completely separated
from the solid, so drying time is often shorter. Water
should be poured over the crystals in order to wash off
the liquid that contains the soluble impurities. If this is not
done, the soluble impurities will be deposited on the
crystals when the solvent evaporates. Activated carbon is
used to bind colored impurities making it easy to separate
the impurities in the pure substance. It is necessary to
cool the filtrate to form the pure substance into crystals
making it easier to separate from the solvent. In the
experiment, the percentage recovery obtained was less
than 50%, meaning more pure substance was left in the
solution. Others may have solidified in the fluted filter
paper before it can be filtered, or some may have not
crystalized while cooling the solution in the ice bath.
CONCLUSION
The objectives of this experiment are to identify the
appropriate solvent for the recrystallization technique and
to use the recrystallization technique in purifying a solid
sample. The objectives were achieved in the experiment
since we have determined the appropriate solvents for
each of the substances and recrystallization was used in
purifying the crude acetanilide sample. We have learned
many things in purification by recrystallization since we
need to know first the suitable solvent for a substance
that needs to be purified. We also need to consider the

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CHM142L Organic Chemistry 1 Laboratory

3rd Quarter SY 2014-2015

characteristics of the solvent to the solute. In performing

the purification of an impure substance by
recrystallization, there are conditions that need to be
followed like dissolving the substance in the least amount
of solvent to prevent recovery loss. Also, equipments
must be considered like the fluted filter paper must be
used rather than a regular filter paper and a stemless
funnel must be used to prevent blocking. We have
learned so many things that can help us in the future,
techniques that can useful and learned skills that can be
applied.
REFERENCES

Anonymous. (n.d.). Purification by

Recrystallization. Retrieved February
25, 2015, from chemistry.sc.chula.ac.th:
http://www.chemistry.sc.chula.ac.th/bsa
c/Org%20Chem
%20Lab_2012/Exp.2[1].pdf
Anonymous. (n.d.). Recrystallization Lab.
Retrieved February 25, 2015, from
OChem331:
http://ochem331.wikispaces.com/Recry
stallization+Lab
Baluyot, J. Y., & De Castro, K. A. (n.d.).
Organic Chemistry Laboratory Manual
for Chemical Engineering Students.

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