Volume No. 5 Issue No.

2
Date of Submission: October 30, 2015
Date of Acceptance: October 30, 2015

Application of Recrystallization Techniques in the Purification of Acetanilide Using

Appropriate Solvent
Macatantan, Sedfrey L.1; Gavio, Patricia Anne L.; Lat, Dheya O.; Manalo, Jayvee Bien D.; Dr. De Castro- Cruz,
Kathlia A.2
Mapua Institute of Technology, Muralla Street, Intramuros, Manila, Metro Manila, Philippines

ABSTRACT
Solubility of a substance varies with the properties of the solute and solvent present. For solids, most have higher
solubility at high temperatures and low solubility at low temperatures. In choosing the most appropriate solvent, the
solute should also be considered. The solvent should be the one that is able to exclude impurities. Recrystallization
is a method of purifying an impure solid in a solvent which results to an impurity-free product. The experiment aims
for us to be able to choose the right solvent for a given compound that can be used for recrystallization; and to
perform recrystallization techniques in the purification of solid samples. Each solid has a solvent that would be
appropriate for it. Acetanilide is used in recrystallization together with water as a solvent. It is done by boiling,
dissolving, filtering, cooling, and vacuum filtering the mixture. The product has been a pure acetanilide which is free
from impurities.
Keywords solubility, solvent, temperature, recrystallization, impurities, purification

Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of
Technology; sedfreymac@yahoo.com
2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology;
kadecastro@mapua.edu.ph

1. INTRODUCTION
Purification of substances is the physical
separation of the wanted substances from the
unwanted ones. It is a vital process especially in
dealing with sensitive experiments wherein pure
substance is a must-use to have good and accurate
results. In using pure substances, there would not be
any hindrance or alterations in the process as the
substance being used is free from any impurities or
any other unwanted parts or substances. On the other
hand, the use of impure substances is the opposite of
what is with pure substances, as impurities and
unwanted substances will be present and they will
also come along in the experiments which would
probably lead to inaccuracies and interferences in
performing the processes and finding the results.
Given that idea, it is important to know
some methods which can be used in purification of
substances. Some are liquid-liquid extraction where
impurities are removed and wanted products are
recovered by dissolving crude materials in a solvent
were parts of the feed are soluble; centrifugation
where at high speed, light particles revolve using an
electric motor so that the particles which do not settle
at the bottom would finally settle down; and
adsorption where impurities that are soluble are
removed by trapping them on the surface of a solid
material which can now form a strong non-covalent
bond with the impurity which then sticks to it
(Barbour & Burl, 2015). These are just few of the
many more purification methods that there are. Also,
the choice of what method of purification to be used
varies from experiment to experiment as it depends
on the type of substances that one has for a solute and
a solvent.
For the experiment, the method that we have
used is recrystallization. Here, a solution will be
created by having an impure solid compound
dissolved in a solvent. Filtration will then be done
and as the solution cools down, the compound will
now crystallize from the solution. As this happens,
the molecules of the unwanted parts of the original
1

substance will be dissolved in the solution and will be

excluded as the solution crystallizes which will then
result to a pure solid (Petrucci, Harwood, Herring, &
Madura, 2007).
To have an effective process of
recrystallization, it should be noted that the impure
solid and its impurities should not have the same
solubility in the solvent that will be used. This now
leads to the selection of the appropriate solvent that
should be used in the application of recrystallization.
In selecting the solvent to be use, the solubilities of
the solute and the impurities should be considered.
Given this, at a high temperature of the compound,
the whole substance should be dissolved, and the
opposite should happen at a low temperature
(Baluyot & De Castro). This is because at lower
temperatures, the heated solution tends to form
crystals, and nothing will happen if it would dissolve
at still low temperatures.
Solid substances could be soluble in for
some solvents and also insoluble for some which is
why properties of both the solute and solvent should
also be considered for choosing the appropriate
solvent. In the experiment, solubilities of different
kinds of solid solutes are tested using different
solvents both hot and cold so that appropriate
solvents would be known for certain solutes, which is
also a part of the recrystallization techniques.

2. EXPERIMENTAL SECTION
Materials Used. Buchner funnel, Thomas-Hoover
melting apparatus, hot plate, stemless funnel, funnel
support, micro test tubes, test tube rack, Erlenmeyer
flask, beaker, capillary tubes, oven
Reagents Used. Acetamide, acetanilide, aspirin,
benzene, benzoic acid, crude acetanilide, distilled
water, ethanol, ethyl acetate, naphthalene, sucrose
Choosing Appropriate Solvent. 0.10 g of the solute
to be used is put on a micro test tube. It will then be
dissolved in 2 mL of the solvent. If the solute does

Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of
Technology; ishy.gavino@yahoo.com.ph
2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology;
kadecastro@mapua.edu.ph

not dissolve, then the mixture will be boiled or put

into a warm water bath. All solutes will be used for
all solvents. Solubilities in both hot and cold
temperature will then be observed.
Recrystallization of Impure Acetanilide. 100 mL of
water is heated. From our sample, 3.50 g of crude
acetanilide is weighed and it is dissolved in 30 mL of
water. The mixture is then boiled on the hot plate. As
it boils, 2 mL of the previously heated water will be
added while stirring until the white solid from the
mixture is completely dissolved. Using the hot
gravity filtration set-up, the solution will now be
poured into the stemless funnel covered by the fluted
filter paper. The filtrate will ran down and it should
be colorless. For our part, the residue crystallized
immediately so we added more heated water and we
simply evaporated the excess water after all of the
solution passed through the fluted filter paper. The
filtrate is then cooled down and placed in an ice bath
while being shook. After crystals are formed, it is
then poured into the Buchner funnel and washed with
cold water. For a while, the wet crystals are dried and
when it is already dry, it is then weighed.

3. RESULTS AND DISCUSSION

In the experiment, we have determined the
solubility of different solutes in different solvents
(both hot and cold). Basing on the properties of the
substances used, particularly the intermolecular
forces, we can at least have an idea of what will
happen after trying to dissolve a certain solute in a
certain solvent. If we can remember, there is a
principle which is like dissolves like which pertains
to the fact that polar molecules can dissolve polar
molecules, and nonpolar molecules dissolve nonpolar
molecules (Yoder, 2015). By keeping this in mind,
we would be able to study more the solubility of the
given solutes in the given solvents. For the
substances used, the polar ones are acetamide,
acetanilide, aspirin, benzoic acid, sucrose (for the
solutes), water, ethanol, and ethyl acetate (for the

solvents) while the nonpolar ones are naphthalene

and benzene for the solute and solvent, respectively.
Table 1. Solubility of acetamide in different solvents
Solvent
Cold
Hot
Acetamide
Water
Soluble
Soluble
Ethanol
Soluble
Soluble
Benzene
Insoluble
Soluble
Ethyl Acetate
Insoluble
Soluble
Previously, it is said that an ideal solvent is
the one that dissolves the solute completely at high
temperature and does not have much effect on the
solute at a low temperature. From Table 1, two
solvents satisfy this description benzene and ethyl
acetate. Based on the fact that like dissolves like,
acetamide and ethyl acetate are polar compounds
while benzene is a nonpolar compound, this proves
that benzene would be the best solvent for acetamide
as they are unlike, meaning that it would be more
impossible for a benzene to dissolve acetamide
(already seeing that all the solvents dissolve
acetamide at high temperatures).
Table 2. Solubility of acetanilide in different solvents
Solvent
Cold
Hot
Acetanilide
Water
Insoluble
Soluble
Ethanol
Insoluble
Insoluble
Benzene
Insoluble
Soluble
Ethyl Acetate
Soluble
Soluble
Table 2 shows the solubility of acetanilide in
different solvents. The solvent that fits the description
for the most appropriate solvent to be used is water. It
is because it shows that acetanilide would be soluble
only at high temperature and insoluble at low
temperature, meaning that the acetanilide would
require high temperature for it to be dissolved
completely and as it does not dissolve at low
temperature, it would simply crystallize once it
passes through the filter and cooled down, as the
impurities would also be filtered easily.
Table 3. Solubility of aspirin in different solvents

Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of
Technology; ishy.gavino@yahoo.com.ph
2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology;
kadecastro@mapua.edu.ph

Solvent
Aspirin
Water
Ethanol
Benzene
Ethyl Acetate

Cold
Insoluble
Soluble
Insoluble
Insoluble

Hot
Soluble
Soluble
Soluble
Soluble

For the most appropriate solvent for aspirin,

it can be said from Table 3 that benzene is the most
appropriate solvent. Three from the four compounds
show that they can dissolve aspirin at high
temperature but cannot at low temperature. The
reason why benzene is the most appropriate is
because in water, aspirin only dissolves a little.
Moreover, ethyl acetate is proved to polar while
benzene is nonpolar. As the aspirin is polar, it is less
likely to be dissolved by benzene, much more in
lower temperatures, which makes it a more
appropriate choice.
Table 4. Solubility of benzoic acid
solvents
Solvent
Cold
Benzoic Acid
Water
Insoluble
Ethanol
Soluble
Benzene
Soluble
Ethyl Acetate
Soluble

in different

Hot
Insoluble
Soluble
Soluble
Soluble

Table 4 shows the solubility of benzoic acid

in different solvents. As can be seen, water is the
most appropriate solvent to be used. It is because
benzoic acid is insoluble in both low and high
temperatures of water which means the impurities
can be easily filtered once the solution is heated and
cooled down.
Table 5. Solubility of naphthalene
solvents
Solvent
Cold
Napthalene
Water
Insoluble
Ethanol
Soluble
Benzene
Soluble
Ethyl Acetate
Soluble

in different

Hot
Insoluble
Soluble
Soluble
Soluble

Table 5 shows the solubility of naphthalene

in different solvents. It can be said that ethanol is the
most appropriate solvent for naphthalene. It is
because naphthalene only partially dissolves in
ethanol. Therefore, impurities will immediately hang
once the solution is filtered.
Table 6. Solubility of sucrose in different solvents
Solvent
Cold
Hot
Sucrose
Water
Soluble
Soluble
Ethanol
Insoluble
Soluble
Benzene
Insoluble
Soluble
Ethyl Acetate
Insoluble
Soluble
From Table 6, it can be said that ethanol is
the most appropriate solvent for sucrose. Sucrose is
only slightly soluble in ethanol. Much less will be
dissolved when sucrose is tested in cold ethanol. This
is why after heating, the impurities can be easily
filtered because it is only partially soluble at high
temperature and not at all at a low temperature.
For the recrystallization part, we know that
recrystallization can be used in separating or
removing impurities of solid substances. The solute
that we have used is 3.50 g crude acetanilide. From
the results listed above, it is known that the best
solvent to be used in this type of recrystallization is
water for the reason that we would want to get as
much crystallized products as we can. Acetanilide is
soluble-enough in water and much more on the other
compounds. Given that, it is because we would want
to use the solvent where the compound will have the
least solubility so once it is filtered out, and cooled,
then impurities would be clinging up in the residue
and the filtrate would just contain the desired crystals
when furtherly cooled. Now, during the heating of the
mixture of water and crude acetanilide, some water
would evaporate which is why heated water is
continuously added. This is also to make sure that the
wanted solids in the solution would be dissolved
completely so that it can pass through the filter paper.
Once the solution is filtered, it would then be cooled
to room temperature and not directly on the ice bath,

Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of
Technology; ishy.gavino@yahoo.com.ph
2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology;
kadecastro@mapua.edu.ph

so that the immediate form of crystals would be

prevented because it would cause impurities due to
the fact that formation of crystal lattice would be
unsuccessful because it is performed faster than it
should have been. The resulting crystals from the ice
bath will then be vacuum filtered so that the solid
product which is the crystal would be separated from
the liquid ones which are still clinging to the crystals.
Now, from the 3.51 g that we started with the crude
acetanilide, the weight of pure acetanilide that we got
is 1.21 which gives us a percent recovery of 34.57%
which is pretty reasonable given the resulting product
that we have. Melting point is measured and it is seen
to be 113C.

4. CONCLUSION
In the experiment, we have dealt with the
determination of the appropriate solvents for given
solutes. It can be said that in choosing for the most
appropriate solvent, we should also consider the
properties of the solutes and solvents as they will also
play a part in deciding which to use. Like dissolves
like principle could help in the determination. Polar
substances would dissolve polar substance; nonpolar
substances would dissolve nonpolar substances. An
appropriate solvent is the one that could exclude all
unwanted impurities while still able to retain the
wanted parts of the original substance.
For the recrystallization, we should take into
account the solvent that would dissolve in high
temperature so that none of it would crystallize
immediately, and also the one that does not have
much effect when the temperature is low. In this case
of crude acetanilide, water is used. This is so the
solution would require more heat to be dissolved, and
would simply crystallize when subjected to low
temperature. In terms of practical works, when
pouring the dissolve mixture in the filter paper, it
should be done very fast so that it would not
crystallize immediately when it experience loss of
heat.

6.
Baluyot, J. Y., & De Castro, K. A. (n.d.).
Organic Chemistry Laboratory
Manual for Chemical
Engineering Students Part 1.
Barbour, P., & Burl, J. (2015, August
31). Recrystallization. Retrieved
from Organic Chemistry at CU
Border:
http://orgchem.colorado.edu/Tec
hnique/Procedures/Crystallizatio
n/Crystallization.html
Petrucci, Harwood, Herring, & Madura.
(2007). General Chemistry:
Principles & Modern
Applications, Ninth Edition.
Pearson Education, Inc.
Yoder, C. (2015). Chemistry. Retrieved
from Wired Chemist:
http://www.wiredchemist.com/c
hemistry/instructional/laborator
y-tutorials/recrystallization

7. SUPPORTING INFORMATION
Table 7. Data on Recrystallization of Impure
Acetanilide
Weight of crude acetanilide
(g)
Weight of filter paper +
crystals (g)
Weight of Filter Paper
(g)
Weight of pure acetanilide
(g)
Volume of water used
(mL)
Melting point of pure
acetanilide (C)
% recovery

3.51
2.32
1.11
1.21
90
113
34.57%

5. REFERENCES
1

Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of
Technology; ishy.gavino@yahoo.com.ph
2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology;
kadecastro@mapua.edu.ph

Figure 3. Vacuum Filtration Set-up

Figure 1. Fluted Filter Paper

Figure 4. Product (Pure Acetanilide)

Figure 2. Hot Gravity Filtration Set-up

1

Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of
Technology; ishy.gavino@yahoo.com.ph
2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology;
kadecastro@mapua.edu.ph

Figure 5. Thomas-Hooover Melting Point Apparatus

Figure 6. Turnitit Similarity Index

Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of
Technology; ishy.gavino@yahoo.com.ph
2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology;
kadecastro@mapua.edu.ph