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Recrystallization is one of the simplest and most widely used technique for purifying organic solids through the
differences in solubility at different temperatures. It is also the process in which the solid to be crystallized is dissolved
to either a hot solvent or a hot solvent mixture and is cooled in a solution.
In this experiment, acetanilide, the crude product of acetylation of aniline and acetic anhydride, was used as
the pure organic compound. Crude acetanilide underwent crystallization process using the preferred recrystallizing
solvent, water. The crystallization process was when crude acetanilide was placed in hot water bath and was cooled
after in an ice bath which would then yield to the formation of crystals of pure acetanilide. The percentage yield form
the crude acetanilide was 73.72% while the percentage yield from pure acetanilide was 61.93%. The percentage
recovery in the experiment was 84.00 %
INTRODUCTION
Organic compounds that came from the
nature, whether solid or liquid, contain impurities
in them. Different purification methods can be
used to remove the impurities present in a
compound. For liquids, distillation is the most
common used purification method. It separates
volatile liquids on the basis of their boiling points.
As
for
solids,
either
sublimation
or
Recrystallization can be used. Sublimation is only
use for solids which can directly pass into vapor
phase without passing through the liquid phase.
On the other hand, Recrystallization involves solid
which doesnt have the same property of liquids
used in sublimation. It is a method which purifies
organic solids base on its solubility. It is also a
process which dissolves solid to be crystallized in
a hot solvent mixture and cools it afterward. The
dissolve solid decreases in solubility at a low
temperature and separates as it cools resulting to
small seed crystals.
Crystallization was done twice. During the
first crystallization a crude product would be
formed which would still have some impurities
that needs to be remove. This was the reason for
doing crystallization for a second time yield to a
pure product which contained fewer or no
impurities at all. The level of purity of the product
can be checked through its melting point range.
Formation of crystals was due to the difference in
solubility of the solid with the solvent. Solutes or
compounds tend to be more soluble in hot
solvents than they were in cold solvents. The
crystals formed have a lattice structure that is a
fixed and rigid arrangement of atoms, molecules
or ions.
Solubility refers to the degree of
substance in which the solute is to be dissolved in
solvent. It was the main factor that affects
crystallization. Identifying the recrystallizing
solvent was very important in crystallization
process. The substance to be crystallized must
Aniline
(C6H5NH2)
also
known
as
aminobenzene or benzenamine is a primary
amine in which the amino group is directly
attached to the benzene ring and the final
product of the reduction of most nitrogen
derivatives of benzene. Its IUPAC name is
phenlyamine, has a density of 1.0217 g/ml and a
molecular weight of 93.13 g/mol. Aniline is a
clear to slightly yellow liquid with a characteristic
form acetanilide.
Figure 3. Structure of Acetanilide
Acetanilide (C6H5NH(COCH3)) which has a
IUPAC name of N-Phenylacetamide is the product
of acetylation of aniline with acetic anhydride at
low temperature. It is an odorless, white flake
solid or crystalline powder. Acetanilide is soluble
in hot water, alcohol, ether, chloroform, acetone,
glycerol, and benzene. It melts at a range of 114116C and boils at 304C. It can undergo selfignite at 545C, but is otherwise stable under
most conditions.
Acetanilide is used as an inhibitor of
peroxides and stabilizer for cellulose ester
varnishes. It is also used as an intermediate for
EXPERIMENTAL
A
Sample
Procedure
1
Used
Acetic Anhydride
Aniline
Acetanilide
Activated charcoal
Methanol
Hexane
Water
First crystallization
Second crystallization
When
the
crude
Acetanilide
was
completely dry, 20-mL of recyrstallizing solvent,
water, was added. It was then placed in a hot
plate until the solid was dissolved. Afterwards the
solution was removed from the water bath, to be
able to put a small amount of activated charcoal
because the solution was colored. A small
amount of activated charcoal was placed to
absorb the colored impurities. Afterwards the
solution was quickly subjected to filtration while
hot. Allow it to cool then collect crystals. It was
then washed by distilled water. Dry the residue
just like the procedure in first crystallization by
pressing the crystals with filter paper that would
sip the remaining liquid, or leaving the crystals
over-night for the liquid to evaporate on its own.
When the pure acetanilide was completely dry, it
was then weighed using the analytical balance.
Figure 5. Filtration Set-up
For the determination of the purity of the
pure Acetanilide find its melting point and
compare it with the theoretical melting point of a
Solvent
Room
temp.
During
heating
Upon
cooling
Water
Insoluble
Soluble
Insoluble
Methanol
Soluble
Soluble
Soluble
Hexane
Insoluble
Insoluble
Insoluble
2.1897 g
1.8394 g
C6 H 5 NH 2 + ( CH 3 CO 2 ) OCH 3 CO 2 H CH 3 CO NH C 6 H 5 +C
Aniline grams :
2 ml C6 H 5 NH 2
1.0217 g
=2.0434 g
1 ml
1.082 g
=3.2460 g
1 ml
2 ml C6 H 5 NH 2
=2.24 g ( C
1 ml
93.13 g
1 mole
3 ml ( CH 3 CO 2 ) O
Hence,
the
C6 H 5 NH 2 ).
1.082 g 1 mole
1mole
=2.96 g C
1 ml
102.09 g 93.13 g
limiting
reagent
is
Aniline
Yield=
Actual Yield
100
Theoretical Yield
2.1897 g
100=73.72
2.0434 g
Actual Yield
100
Theoretical Yield
ActualYield
100
Theoretical Yield
1.8394 g
100=61.93
2.0434 g
From books
Martin & Gilbert (2011). Organic Laboratory
Experiment (5th Ed.). Boston: Cengage
Learning.
University of Santo Tomas. Faculty of
Pharmacy. Organic Chemistry Group. (2009).
Laboratory Manual in Organic Chemistry.
Quezon City: C&E Publishing Inc.
Ault (1983). Techniques & Experiments fo
Organic Chemistry (4th Ed.). Massachusets:
Ally & Bacon Incorporated.
From websites
The
percentage
recovery
of
pure
acetanilide from the crude acetanilide was also
computed which is shown below.
Recovery =
Recovery =
% Recovery = 84.00%
The
percentage
recovery
of
pure
acetanilide was 84.00% which means there was
only a minimum amount of acetanilide lost and
the experiment was a success. The pure
acetanilide that was collected was colored white.
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