RECRYSTALLIZATION

UST Faculty of Pharmacy

Celzo, Chelzea
Co, Gian
Cruz, Dianna
Dalmacio, Trisha
Fabillaran, Joeselline
Guibani, Samantha
Group 2, 2E PH

ABSTRACT
Recrystallization is the primary method for purifying solid organic compounds
through the differences in solubility at different temperatures. The dissolved solid has a
decreased solubility at lower temperature and separates from the solution as it is
cooled. A small seed crystal is formed initially, and it then grows layer by layer. In this
experiment, acetanilide was formed by the acetylation of aniline and acetic anhydride.
The crude acetanilide was dissolved in a solvent in a hot water bath. The solution was
then cooled in an ice bath as crystals start to form. As the compound formed crystals,
molecules of other compounds dissolved in the solution are excluded from the growing
layer of crystals; hence, pure acetanilide is formed.
I.

INTRODUCTION

After the extraction of a

compound from a natural product, it is
still in an impure form. But there is a
need to purify the compound if it is to be
used for manufacturing certain products.
If the product is solid, it can be purified
by sublimation or crystallization. In the
experiment, recrystallization method
was used in order to purify organic
solids based on solubility.
In recrystallization, a solution is
created by dissolving a solute in an
appropriate solvent at or near its boiling
point.
The
principle
behind
recrystallization is that the solubility of a
compound increases with temperature
and decreased solubility as it cools
down, forming a crystal form. The first
crystallization, the product formed is the
crude acetanilide which still have

impurities. To remove this impurities, we

heated it in water bath until the solid
dissolves. This will result to a residue
which is the activated charcoal and
insoluble impurities and the filtrate which
is the acetanilide and the soluble
impurities. And on the filtrate, we placed
it on an ice bath and later filtered it
resulting the filtrate which is the watersoluble impurities and the residue which
is the final product, the pure acetanilide.

Aniline, phenylamine or aminobe

nzene is an organic compound with the
formula C6H5NH2. Consisting of a phenyl
group
attached
to
an
amino
group, aniline is
the
prototypical
aromatic amine. Being a precursor to
many industrial chemicals, its main use
is in the

manufacture
of
precursors
to
polyurethane. Like most volatile amines,
it possesses the somewhat unpleasant
odor of rotten fish.
Figure 1. Structure of Aniline
Acetanilide is the product formed
in this experiment. Acetanilide or NPhenylacetamide
is
an
organic
compound with the formula C8H9NO.
Consisting of a phenyl group attached
which is hydrophobic and an amido
group attached which is hydrophilic.
Acetanilide is used as an inhibitor of
peroxides and stabilizer for cellulose
ester varnishes.
Figure 2. Structure of Acetanilide

Acetic anhydride is the reagent

added to aniline to undergo acetylation.
Acetic anhydride is a clear colorless
liquid with a strong odor of vinegar with
a molecular formula of C4H6O3. It is
corrosive to metals and tissue. It has a
density of 9.0 lb /gal. It is used to make
fibers, plastics, pharmaceuticals, dyes,
and explosives. Aniline reacts with
acetic
anhydride
by
nucleophilic
substitution reaction. The reaction
between aniline and acetic anhydride is
called acetylation.

Figure 3.
Anhydride

Structure

of

Acetic

II.
III.

MATERIALS AND METHODS

Figure 1. Fractional Distillation
Set-Up

Methodology

The grop prepared 15 numbered

test tubes which is calibrated to
0.5mL.
After which, we added 30mL
vodka to the distilling flask with
boiling stones.

Then, the group heated the

distilling flask using an alcohol
lamp until the vodka boiled.
Temperature was recorded at
Afterwards, the group collected
the first drop of the distillate.
0.5mL each of the distillate in
eachgroup
calibrated
test
tubes
and
The
placed
3-5
drops
of
recorded
thefrom
temperature
in
the
distillate
the first and
each
occurred.
last distillate
test tubethat
seperately
onThe
a
collection
at 100C.
watch
glassstopped
and subjected
it on
fire to determine whether the
distillate is flammable or nonflammable.

IV.

RESULTS AND DISCUSSION

In order to attain the best

recrystallizing solvent, the compound
mixed in the solvent should be insoluble
at room temperature; soluble while

heating; and separates from the solution

upon cooling. At the same time,
impurities that are present must either
be soluble in the solvent at room
temperature or insoluble in the solvent
at a high temperature (Schaeffer, 2016).

Water
Methano
l
Hexane

Room
Temperature
insoluble
soluble

During
Heating
soluble
soluble

% recovery =

Upon
Cooling
Insoluble
Soluble

2.95 x100
4g

= 73.75%

insoluble

insolubl insoluble
e
Table 1. Solubility of Pure Acetanilide in
different solvents

Table 1 shows the solubility of

acetanilide using the three different
solvents namely the water, ethanol, and
hexane. At room temperature, the
acetanilide in water is insoluble and
became soluble at a higher temperature
and became insoluble when placed in a
lower temperature. The solid in ethanol
exhibited solubility in all temperature,
while acetanilide in hexane is insoluble
in all temperature. Water is the suitable
recrystallizing agent because it suffices
the criteria where the compound must
be insoluble in room temperature,
soluble when heated and will be
insoluble when cooled. Pure acetanilide
melts at 110 degrees Celsius.

% yield=

actual
x100
theoretical

% recovery =

Pure acetanilide x100

Crude acetanilide

V.

CONCLUSION
As weve noticed, the
percentage recovery of pure
acetanilide acquired in the
experiment was 73. 75% which
means there was only a minimum
amount of acetanilide lost. In
conclusion, the more the solute
had undergone crystallization, the
purer it get but the amount
decreases.

REFERENCES:
Yoder, Claude (2016). Retrieved
October 17, 2016. Website:
http://www.wiredchemist.com/chemistry/i
nstructional/laboratorytutorials/synthesis

Bathan, Gladys I.. Bayquen, Aristea V.

(2014). Laboratory Manual in Organic

Chemistry Revised Edition. C&E

Publishing, Inc.