EXPERIMENT 3

RECRYSTALLIZATION
Abarro, Justine Marie E., Andrade, Ehmmarie L., Hernando, Camille D., Sta. Isabel, Jamie Anne.,

A B S T R A C T
Recrystallization is a process of purifying solid organic compounds. In this experiment
the students were assigned a solid sample and need to determine the solubility by the given
solvents. Acetanilide was the sample in this experiment. We will discover different methods,
determine and know different ways in choosing appropriate solvents

for recrystallization

process.
I. INTRODUCTION
Organic

be

of the compound whether it may be solid or

synthesized in laboratory or be obtained

liquid. In this experiment, an unknown solid

from natural sources. The purification and

compound had undergone the process of

structure establishment of an unknown

recrystallization. Recrystallization is defined

compound is very necessary. The compound

as the method of dissolving impure substance

must be first obtained in a pure state. In fact,

in a suitable solvent and then allowed to cool

there are several methods available to

at room temperature (Davis, 2007). While

achieve purification of a sample. The

cooling, the pure substance crystallizes out

product obtained from a chemical reaction is

from the solution whereas the impurities

frequently contaminated with impurities.

remain dissolved in the solvent. It is

With these impurities present, the melting

preferred that the substance should have a

point or boiling point of the compound is not

high solubility in the hot solvent but low

sharp. One method to purify this compound

solubility in cold solvent. Sample compound

is recrystallization.

may often contain some colored impurities

Although
methods

available

compounds

there
for

are

can

numerous

purification,

which can be removed during the process

the

(Bansal, 2003). In this process, the crystals

technique to be used still depends on the state

from a hot solution should inaugurate to

appear as soon as the solution is allowed to

bath, seeding in which scratching the sides of

cool. Nevertheless, if this does not occur, one

the container with a glass rod or adding a

may have to resort to some other means. This

crystal of the pure compound takes place

may include cooling the solution in an ice-

(Ahluwalia, 2004).

II. METHODOLOGY

water in a clamped 125-mL Erlenmeyer

In order to carry out this experiment,

the

solvents

for

slightly boiled to 150 degrees. When the

recrystallization. Hot water bath inside the

mixture starts to boil, 2-mL portions of the

fume hood was prepared. A half-fill 150-mL

previously heated water was added and

beaker with distilled water was placed in a

stirred until the white solid completely

hot plate heated to 150 degrees. Four test

dissolves. The temperature at around 90

tubes were labeled (1) water, (2) ethanol, (3)

degrees was maintained while adding hot

benzene,

acetate.

water. The volume should not exceed at 70-

Approximately (4) 0.10g of the assigned

mL since the solubility of acetanilide is

solid sample in a creased paper and put it in

4.30g/100-mL of water. This step was only

each of the prepared test tubes. With a pipet,

performed for less than 15-minutes to

2-mL of the cold solvents were put in each

prevent loss of solvent through evaporation.

of their assigned test tubes and the solubility

Since th solution is colored, small amount of

behavior of the solid sample was observed.

activated carbon was added and the flask

Since the solid sample fails to dissolve in a

were swirled. Too much adding of activated

given solvent, the mixture was heated in the

carbon can absorb the dissolved crystal

prepared hot water bath in the fume hood.

itself. Adding activated carbon while the

The water was placed in a hot water bath.

solution is boiling can cause the solution to

and

were

(4)

first

tested

flask. Using the hot plate, the mixture was

ethyl

In the recrystallization part of the

boil over. The mixture was reheated to 90

experiment, fluted filter paper, hot gravity

degrees. Using the set up for hot gravity

filtration set up and vacuum filtration set up

filtration, the solution was poured over to a

were prepared. Around 100-mL of water in a

fluted filter paper situated in the funnel. At

250-mL beaker was heated. Approximately

this point, the filtrate obtained was colorless.

3.50g of crude acetanilide was weighed.

The flask was then removed from the hot

This compound was dissolved in 30-mL

plate and the residues were discarded. The

solution was cooled down on top of a

solvent. The solid sample must be insoluble

cooling pad, clamp was removed from flask,

in the solvent at room temperature but more

and an inverted 250-mL beaker was placed

soluble in the solvent at higher temperature.

to cover the flask then set aside to cool to

If the solid sample was insoluble in solvent

room temperature. Since crystals were not

at a higher temperature then it will not

formed

three

dissolved. If the solid sample was soluble in

induce

solvent at a room temperature, then getting

crystallization (1) scratch lightly the inner

the crystallization form will be difficult.

sides of the flask with a stirring rod, (2) dip

Then the next criteria, Impurities that are

a glass rod in the solution and then aerate it

present must either be soluble in the solvent

to dry off the solvent thenreturn the rod to

at room temperature or insoluble in the

the solution and (3) add seed crystal to the

solvent at a high temperature. If solid

solution. After a few minutes of cooling the

sample was dissolved in a hot solvent,

solution, rubber stopped and clamp was

impurities can be filtrated. The third criteria

inserted, then the solution was placed in an

was the solvent must not react with the

ice water bath to increase the output of

sample. The compound will be lost during

crystals.

was

recrystallization process. And lastly, the

completed, the solution was vacuum filtered.

solvent should be volatile enough to be

The crystals wewre washed with about 2-mL

easily removed from the solvent after it

of cold water. The crystals were placed on

crystallized. It allows easy and fast drying of

the petridish and was left to dry for a few

It allows easy and fast drying of the solid

days. After a few days, the crystals were

sample after being isolated from the

weighed and the percentage recovery was

solution.

at

techniques

room
are

temperature,

available

Once

to

crystallization

computed.

In the first part of our experiment,

III. RESULTS AND DISCUSSION

we were given a solid sample and we were

Recrystallization is a process of

about to determined the solubility of the

purifying organic solid compounds. In

sample in a solvent. There were different

recrystallization process, it only works in

solvents given: water, ethanol, benzene and

choosing

ethyl acetate. In a four different test tube we

an

appropriate

solvent

in

dissolving our solid sample. There were

different criteria in choosing an appropriate

put 0.10 g solid sample in each.

Table3.1 Testing Solubility of Solid Sample

Erlenmeyer flask. We boiled our mixture

to

and when it starts to boil, we add 2mL of the

Different

Solvents

to

Varying

Temperatures.

previously heated water with stirring until it

Solid

Solubility ( Soluble Appropr

dissolves. We must add enough water in

Sample

or Insoluble)

iate

dissolving our solid sample in getting

Recrysta

saturated solution at the boiling point of

llization

solvent. It was necessary because when the

Solvent(

solution was cooled, fewer crystals will

/ or X)
X
X
/
X

form. We added a small amount of activated

number
Cold

Water
Ethanol
Benzene
Ethyl

Insoluble
Soluble
Insoluble
Soluble

Hot

Insoluble
Soluble
Soluble
Soluble

Acetate
In our data, the appropriate solvent
for our solid sample was the benzene. Based
on the criteria above the solvent must be
insoluble in room temperature and soluble at
high temperature.
Table 3.2 Recrystallization of Acetanilide.
Step in Procedure
Dissolution of acetanilide
Addition of Activated Carbon
Hot Gravity Filtration
Cooling to Room Temperature
Cooling in an Ice bath

carbon. Colored impurities cannot be easily

removed in the mixture.
Adding activated carbon can removed the
color of the impurities. It also provides
higher surface area to gather the color of the
impurities.
Using hot gravity filtration, we poured the
solution into the fluted filter paper in the
funnel. The arrangement of the fluted filter
paper allows the liquid to pass quickly and a
lot of surface area in collecting solid
Observation
impurity.
Then cloudy
we removed
our sample
The solution
becomes
and color
pink. from
The solution
clear.
the hotbecomes
plate. We
cooled it slowly in a room
The white crystal form.
temperature.
It was not required to put it in
More crystal
formation.
When our
sample
in an
bath, many
crystals
an ice
bath was
during
hotice
filtration
step because
formed precipitate
at this partmay
than
when cooling it to room
form.

Vacuum Filtration
After choosing appropriate solvent, we
proceed to next step. We prepare the set up
for recrystallization process. We heat 100mL
water. We weigh 3.50g of acetanilide and
dissolved it in 30mL of water in an

temperature.
In our case, crystals do not form faster as
The less crystals seen in the flasks.
what we expected. We lightly scratch the
inner glass wall of the flask. This was done
to release some particles that stuck from the
sides of the flask. Then we put our sample in

an ice bath to increase the amount of crystal

different criterias in determining the right

formation.

solvent. First the solid sample must be

After crystallization was completed, we

insoluble in solvent at room temperature and

vacuum filter our solution. We washed the

soluble in solvent at high temperature. The

crystals.

second was the impurities must be soluble in

solvent at room temperature and insoluble in

Table3.3

Percentage

Recovery

of

Recrystallized Acetanilide

hot solvent. The next one was the sample

should not react with the solvent. And lastly,

the solvent should be volatile to be easily

Mass of crude acetanilide (g)
Mass of petri dish (g)
removed from the solvent after it was been
Mass of ashless filter paper (g)
Mass of recrystallized acetanilide, petri dish, crystallized. There were different methods
which plays an important role in crystal

ashless filter paper (g)

Mass of recrystallized acetanilide (g)
Percentage Recovery (%)
In

table3.3

it

shows

that

formation. New techniques we encounter

like the vacuum filtration and hot gravity
the

percentage of recovery we have was 17%.

filtration. After performing the experiment

the percentage of recovery was 17%.

IV. CONCLUSION
In recrystallization process, choosing an
appropriate solvent is a must. There were

V. REFERENCES
Bansal, Raj, K. 2003. A Textbook of Organic Chemistry. 4th ed. New Age International. New
Delhi, India.
Davis, Raymond E., M. Larry Peck, and George G. Stanley. Chemistry. By Kenneth W. Whitten.
Eighth ed. Belmont, California: David Harris, 2007.
Ahluwalia, V.K. Dhingra, S. 2004. Comprehensive Practical Organic Chemistry:
Qualitative Analysis. Universities Press.
IV. Conclusion