RECRYSTALLIZATION

Adolfo, Angela Nicole G., Alcaraz Frances Jillian F., Aliman, Stephanie T., Astor, Jashmin D.,
Bauzon, Franchesca D., Cabral, Danica Rose G.

Department of Pharmacy, Faculty of Pharmacy

University of Santo Tomas
ABSTRACT
Recrystallization is a purifying method of organic solids where the amount of solute that
can be dissolved by a solvent increases with temperature. In the experiment, each of the three
test tubes contains pure acetanilide dissolved in water, ethanol, and hexane respectively. The test
tubes were observed at room temperature, during heating (37-40 C) and upon cooling. Moreover,
there was crude acetanilide obtained from mixture of aniline, distilled water and acetic anhydride.
Water was used as the recrystallizing solvent to obtain the pure acetanilide. The crude and pure
acetanilide was weighed. After which, the percentage yield of acetanilide was computed and the
melting point of the recrystallized acetanilide was determined. Therefore, recrystallization is a
good purification method compatible with the nature of acetanilide.
INTRODUCTION
A solid sample can be purified

in a purer form because the impurities won't

through the process of recrystallization, to

crystallize

prepare a highly concentrated solution at a

impurities behind in the solution. A filtration

high temperature. Melting point can be used

process must be used to separate the more

to determine the purity of this sample. The

pure crystals at this point. The procedure can

solution

the

be repeated. Solubility curves can be used to

temperature causes the solubility of the

predict the outcome of a recrystallization

impurities in the solution and the substance

procedure. The slower the rate of cooling, the

being purified to decrease. The impure

larger the crystals are that form. The

substance then crystallizes

before the

disadvantage of recrystallization is that it

impurities- assuming that there was more

takes a long time. Also, it is very important

impure substance than there were impurities.

that the proper solvent is used. This can only

The impure substance will crystallize

be determined by trial and error, based on

is

cooled.

Decreasing

yet,

therefore

leaving

the

predictions and observations. The solution

of obtaining a pure sample of some product,

must be soluble at high temperatures and

or precipitate.

insoluble

at

low

temperatures.

The

advantage or recrystallization is that, when

carried out correctly, it is a very effective way
The following are the objectives
1.)

To be able to select an appropriate

3.)

To compare the melting points of

impure and recrystallized acetanilide

recrystallizing solvent
2.)

To separate and purify acetanilide by

recrystallization
METHODOLOGY
Prepare three (3) different test tubes

In an Erlenmeyer flask, mix 2mL of

and place a corn-grain sized amount of pure

Aniline and 20mL of distilled water, and then

acetanilide, then add distilled water to the

slowly add 3mL of acetic anhydride. Note the

first test tube, hexane to the next one, and

changes then cool the flask in an ice bath to

ethanol to the last. Before placing it in a water

speed up the crystallization of the solution.

bath for 1-5 minutes, make sure that the test

The solution was then filtered to obtain the

tubes were shaken. The test tubes were

fully formed crystals, let it dry by pressing

placed to an ice bath right after, and note the

with filter paper and weigh the crude

solubility of the pure acetanilide in the

Acetanilide.

different solvents at varying temperature.

For the second crystallization, pour

impurities and heat it again. After heating, the

20mL of water of the recrystallizing solvent

solution should be filtered immediately while

when the crude Acetanilide was completely

it is still hot using a fluted filter paper. The

dried. The solution was placed in a water

filtrate was placed on an ice bath to hasten

bath until all the solid dissolves. If the

the crystallization. Collect the crystals and let

solution shows a change in color, add a pinch

it dry by pressing in-between filter papers,

of activated charcoal to remove the colored

and then weigh it.

After heating, the solution was filtered

placed on an ice bath to hasten the

immediately while it is hot and the filtrate was

crystallization of the solution. When the

solution is done crystallizing, the solution

between filter papers. The yielded pure

was filtered and the crystals were collected.

acetanilide was weighed.

The crystals were dried by pressing inRESULTS AND DISCUSSION

Table 1 - Solubility of Pure Acetanilide in

Different Solvent

A recrystallizing solvent is a
solvent that shows the desired solubility

Solvent

behavior for the substance to be crystallized,

Room

During

Upon

temp.

heating

cooling

and the process of recrystallization starts

with finding the right crystallizing solvent. In
choosing the recrystallizing solvent, the

Water

Insoluble Soluble

Insoluble

Methanol

Soluble

Soluble

Hexane

Insoluble Insoluble Insoluble

Soluble

compound being purified must be insoluble

in solvent at room temperature and must be
soluble in boiling solvent. The solvents
boiling point must be lower than the melting

In the experiment, three solvents

point of the compound. The unwanted

were used, such as Water, Methanol, and

impurities should be soluble at room

Hexane. The solvents were used to identify

temperature or insoluble during heating.

which solution would best suit for the

experiment. As tabulated on Table 1, hexane

The solubility of Acetanilide was

was insoluble in all temperatures and the

tested for the three given solvents: Water,

opposite for methanol which is soluble in all

Hexane, and Methanol. A compound usually

temperatures; as for water, it is insoluble at

exhibits one of the three general solubility

room temperature and upon cooling, but

behaviors: (1), the compound has a high

during heating it is soluble. Therefore, two of

solubility in both hot and cold solvent, (2), the

the chosen solvents cannot be used for the

compound has a low solubility in both hot and

recrystallization of acetanilide. Including the

cold solvent, and (3), the compound has a

verity that both hexane and methanol were

high solubility in hot solvent and low solubility

known to be highly volatile and flammable.

in cold solvent. A solvent showing the last

And as distilled water being the only option

characteristic or behavior is the one suitable

left, it is ceased that water is the ideal

as a Recrystallizing Solvent.

recrystallizing solvent for acetanilide.

In acetylation of aniline with acetic
anhydride, the yielding acetanilide exhibits

an exothermic reaction. Exothermic reaction

Thus, crystals form. Hastening crystallization

is the release of heat from the system. In

is done through ice bath. This method

case of cooling, the heat has to be removed

decreases the solubility of acetanilide.

from the system, the temperature is lowered.

the weight of the crude acetanilide is 4.80 g

first in a reaction must be determined first. It

The crude acetanilide was then subjected to

also limits the amount of product to be

the addition of the recrystallizing solvent

formed.

which is water and placed in a hot plate.

During the process of heating in a water bath,

Calculation for the determination of the

impurities may cause the solution to be

limiting reagent: (First Calculation)

colored, or have color. To let these color

vanish, activated charcoal can be applied to
remove the colored impurities of the solution.

2 ml aniline x

1.0217 g
= 2.0434 g
1 ml

2 ml aniline = 2.0434 g aniline

Activated charcoal was used to
adsorbs the impurities because it has a large
surface area and it can remove impurities
more effectively. Only a small amount of

3 ml acetic anhydride x

1.082 g
= 3.246 g
1 ml

activated charcoal should be added. Too

much activated charcoal will not only adsorb
the impurities but also the desired product.

3 ml acetic anhydride = 3.246 g

acetic anhydride

When the acetanilide was dissolved,

the solution should be immediately filtered

The

calculated

values

are

the

while hot using a fluted filter paper. The

amounts of the two reactants in terms of

filtrate was subjected to ice bath to speed

mass. These are used to determine if the

up the cooling process. The crystals

amount of each reactant is enough or more

collected were dried by pressing in between

than what is needed for the chemical

filter papers.

reaction.

To calculate the percentage yield of

the recrystallized acetanilide, the limiting
reagent which is the reactant that is used up

% Recovery =

3.70 g
100
4.80 g

% Recovery = 77.08%
Figure 1. Calculation for the determination of
the limiting reagent.

The percentage recovery was 77%,

which means there was only a minimum
amount

of

acetanilide

lost

and

the

aniline

experiment was a success. The pure

because it needed 2.96 g to react with 3 ml

acetanilide that was collected was colored

of acetic anhydride but only 2.0434 g is

white.

The

limiting

reagent

is

available to be used. Theoretical yield, the

maximum yield of pure crystals that could be
obtained by cooling or evaporating a given
solution, will be the mass of the limiting
reagent. This refers to the quantity of pure
crystals deposited from the solution.

CONCLUSION
As a conclusion, the process of
recrystallization is a quick, simple, and easy
way to purify a compound whether it is known
or unknown. Recrystallization is a good

% =

purification method compatible with the

100

nature of acetanilide. It is efficient for

dissolving the solid to be crystallized in a hot

2.70
% =
100
2.970

solvent or solvent mixture and by then,

cooling the solution slowly. It is also

% = 90.9%

somehow useful for identifying an unknown

compound because impurities affect boiling
and melting points which can cause or may

The calculated percentage yield was

lead to the identification of another different

90.9 %. Percentage recovery is the percent

compound. Charcoal, or for a concrete

of the pure form of a compound formed

example that was used in the experiment is

during the reaction. This refers to the percent

the activated charcoal, is useful in removing

of

some of the impurities of the mixture.

pure

acetanilide

formed

after

recrystallization.
% Recovery =

mass of pure acetanalide

mass of crude acetanalide
100

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