CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

Recrystallization
Miranda, Marilyn; Orense, Lara Melissa S.
Miranda, Marilyn, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; Orense, Lara Melissa S., CHM142L/B21, School of
Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology

ABSTRACT
Recrystallization is a method of choice for purifying organic solids. It involves dissolving a solid in a solvent and crystallizing
it again, taking the opportunity to discard impurities along the way. The researchers were to identify the appropriate solvent
for recrystallization technique and to use this method to purify a solid sample. Different solutes were to be dissolved in
different solvents and the researchers must observed its solubility behavior. For the recrystallization of the impure
compound, series of procedures like hot gravity filtration and vacuum filtration were to be followed to obtain a pure solid
compound. Its melting point and percent recovery were to be determined by the researchers. The researchers successfully
determined the solutes solubility behavior in different solvent. Also, they managed to get a high yield of crystals from
recrystallization although their observed melting point was far from that of the actual. This may be due to the amount of
sample used and the wrong observed temperature when it starts melting and when it completely melts. The researchers
should notice these small details in order for them to have an accurate and correct results.
Keywords: recrystallization, solvent, solubility, filtration, purify

INTRODUCTION
Substances, when reached specific temperatures, dissolve
in a solvent. Differential solubility is defined as the
difference in the amount of solid that can be dissolved in a
solvent as affected by variations in temperature. Usually,
substances or solutes solubility increases as the
temperature increases.
Recrystallization is a method of choice for purifying organic
solids. It involves dissolving a solid in a solvent and
crystallizing it again, taking the opportunity to discard
impurities along the way. One normally chooses a solvent in
which the solubility increases significantly with temperature.
The solid is dissolved in a minimal amount of hot solvent,
and the solution is filtered to remove insoluble impurities.
Upon cooling the solution, the desired compound
crystallizes, leaving soluble impurities in solution.
Alternatively, a mixed solvent system can be used to modify
the solubility the key is to get the compound into solution
then get it back out of solution.
In order for recrystallization to be effective, the solid and
impurities must have different solubilities in the solvent.
Impurities that remain undissolved in the solvent are
removed by filtration of the hot mixture. On the other hand,
soluble impurities that remain dissolved even after

Experiment 02 Group 8Nov. 7, 2014

crystallization are separated by filtration of the cold mixture.

Choosing an appropriate solvent is must for
recrystallization. This is to be done by looking at the
solubilities of both solute and the impurities. An ideal
recrystallization solvent should perform the following
conditions: dissolve all the substance at high temperature,
have different solubilities for the compound and impurities,
have a boiling point below the melting point of the
compound, be inert with respect to the compound, dissolve
very little of the compound at low temperature and must be
inexpensive.

MATERIALS AND METHODS

For this experiment, the researchers used the the
following apparatus: Buchner funnel, ThomasHover melting apparatus, hot plate, stemless
funnel, funnel support, micro test tubes, test tube
rack, Erlenmeyer flask, beaker, capillary tubes
and oven.

1 of 5

CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

This experiment requires the use of the following

reagents: Acetamide, Acetanilide, Aspirin,
Benzene, Benzoic acid, Crude acetanilide,
distilled water, Ethanol, Ethyl acetate,
Naphthalene and Sucrose. This reagents were
provided and prepared beforehand by the
Chemistry Stockroom and laboratory assistant.
For part I, the researchers were asked to weigh
0.10 g of acetamide, acetanilide, aspirin, benzoic
acid, naphthalene and sucrose then put each in a
micro test tube. It should be dissolved in 2 ml of
the following solvents: cold water, ethanol,
benzene and ethyl acetate. The researchers
observed the solubility behavior. The mixture
was placed in a hot bath if the acetamide failed to
dissolve.
For part II, the researchers were asked to setup
the process for hot gravity filtration and vacuum
filtration. The researchers heated 100 ml of
water, while they waited, they weighed 3.50 g
crude acetanilide and dissolved in 30 ml of water.
They boiled the mixture and continuously added
2-ml portions of previously heated water until the
white solid completely dissolved. They recorded
the total volume used but it should not exceed 70
ml. Since the researchers solution is already
colorless, they didnt add activated carbon to
their solution. Using hot gravity filtration setup,
they poured the solution into the fluted filter
paper placed in a stemless glass funnel. After
they cooled down the filtrate for a while, they
placed it in an ice bath then proceeded to vacuum
filtration setup after crystallization was complete.
They vacuumed the filter and washed the crystals
using water. It was then dried in an oven and
weighed.

RESULTS and DISCUSSIONS

Each solute was to be dissolved at different solvents like
water, ethanol, benzene and ethyl acetate. If the solute was
dissolved in the cold water, there is no need to dissolve it in
hot water for the reason that most substances increases

Experiment 02 Group 8Nov. 7, 2014

solubility as temperature increases. Otherwise, the solute

must be put in a hot bath and observe if the solid dissolves
or not. The overall summary of these solutes solubility is
seen in Table 1. From that table, acetamide and benzoic
acid dissolve completely in water and it will be soluble in
ethanol, benzene and ethyl acetate once the temperature
increases. Acetanilide and aspirin dissolve completely in
ethanol and ethyl acetate. Naphthalene dissolves
completely in benzene and ethyl acetate while sucrose
dissolves completely only in water and it doesnt dissolves
in benzene and ethyl acetate.
Table 1. Solubility and insolubility of different solutes in different
solvents (S-Soluble and I-Insoluble; C-Cold water and H-Hot
water)
Compound
Acetamide
Acetanilide
Aspirin
Benzoic Acid
Naphthalene
Sucrose

Water
C
S
I
I
S
I
S

H
S
S
I
S
I
S

Ethanol

Benzene

C
I
S
S
I
I
I

C
I
I
I
I
S
I

H
S
S
S
S
S
S

H
S
S
S
S
S
I

Ethyl
Acetate
C
H
I
S
S
S
S
S
I
S
S
S
I
I

As discussed in the Introduction, the ideal solvent for

crystallization of each compound is the one where the
compound is insoluble in cold temperature but soluble in
hot temperature. This difference in solubility at hot

versus cold temperatures is essential for the

recrystallization process. If the compound is
insoluble in the chosen solvent at high
temperatures, then it will not dissolve. If the
compound is very soluble in the solvent at room
temperature, then getting the compound to
crystallize in pure form from solution is difficult.
Also, the boiling point of the solvent should be
lower than the melting point of the compound.
The solvent should be volatile enough to be
easily removed from the solvent after the
compound has crystallized. This allows for easy
and rapid drying of the solid compound after it
has been isolated from the solution.
The choice of solvent for a recrystallization is crucial. If the
solvent is too good, then even when the solvent is cold the
sample will remain dissolved and obtaining any crystals is
impossible. If the solvent is too bad, then even when the
solvent is hot it still wont be able to dissolve the sample,

2 of 5

CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

and the impurities wont be freed from the original sample.

An effective solvent must be good enough to dissolve the
sample at high temperature (so that the impurities are
freed), but weak enough so that at least some of the
sample crystallizes out after cooling.

The researchers choice of solvent for acetamide,

aspirin and sucrose is different compared to the
appropriate solvent for crystallization (Table 2).
The ideal solvent for these compounds should be
benzene, benzene and ethanol, respectively. The
reason why the researchers choices were
different from that of the appropriate one was
because they picked the solvent where the
compound will be insoluble for both cold and hot
temperatures instead of solvent where the
compound will not dissolve in cold/room
temperature but will dissolve all the compound in
hot temperature. In case of sucrose, they recorded
water as the solvent for recrystallization as
opposed to the observed solubility of this
compound in cold water.

temperature, This was what happened in water.

This was also proven because water boiling
point (100C) is lower than acetanilides melting
point (114.3C). Also, in aspirin, only in benzene
will it be insoluble at cold temperature and
soluble at high temperature. Moreover, benzenes
boiling point (80.1C) is lower than aspirins
melting point which is 136C. Even though
benzoic is soluble in water for both cold and hot
temperature, it will be the appropriate solvent
because at 20C only 4.1 g of benzoic acid
dissolves in 1 liter of water, while at 95C the
solubility is 68 g/L. Same goes for naphthalene
and benzene because they were insoluble in cold
temperature in water and ethanol, respectively
and soluble in hot temperature.

Figure 1. Solutes-Acetamide, Acetanilide,

Aspirin, Benzoic Acid, Naphthalene and Sucrose
(starting
from

Table 2. Appropriate solvent for recrystallization

of each solute
COMPOUND
Acetamide
Acetanilide
Aspirin
Benzoic Acid
Naphthalene
Sucrose

SOLVENT
ethanol
water
ethyl acetate
water
water
water

As seen in Figure 1, the compound acetamide is

polar due to its functional groups (amine and
C=O). That is why the solvent where it will be
recrystallize will be nonpolar solvents like
benzene and ethyl acetate. Benzene is more
suitable since the boiling point of benzene is
80.1C is in between the value of melting point
of acetamide which is 79-81C. Acetanilide is a
polar compound, its appropriate solvent should
be water which is a polar solvent. It is because a
good recrystallization solvent will not dissolve
the compound at cold or room temperature but
will dissolve all the compound at hot

Experiment 02 Group 8Nov. 7, 2014

upper left going right)

3 of 5

CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

Usage of minimum amount of solvent to dissolve

solute is necessary because it will maximize the
yield or the resulting crystal. In the process of
filtration, the researchers used a fluted filter
paper instead of the traditional way of folding the
paper for the following reasons: first, fluted filter
paper will increase the filter area for the solution
and second, the fluting creates gaps between the
filter paper and the funnel in which it is resting.
These gaps provide channels for the solvent to
flow through after it passes through the filter
paper, thus greatly increasing the speed of
solvent flow through the paper. Also, instead of
using an ordinary glass funnel, the researchers
made use of stemless glass funnel (Refer to
Figure 2) for this process because crystals can
form in a cool stem or long-stem funnel and clog
it. If the obtained filtrate has a tint of color,
addition of activated carbon is a must. It is very
finely divided carbon that provides high surface
area to adsorb the colored impurities and remove
these in
the
sample.
Figure 2.
Hot
filtration
setup

After having the filtrate which is now in the

Erlenmeyer flask, it will be placed in an ice bath
to obtain maximum yield of the crystals. As the
temperature decreases, the solubility also
decreases, therefore a higher possibility of much
crystal formation. Take note that before placing it
in a ice bath, cool down the flask for a few
minutes because immediately placing a hot
glassware in cold environment may result to a
crack in the flask.
After placing the filtrate in the ice bath,

formation of crystals will be observed. To

maximize the yield of crystals, the researchers
used vacuum filtration for a faster way of sucking
out the water from the solution leaving the solid
in the Buchner funnel (Figure 3). Washing the
crystals with water will ensure that crystals on
the side of the flask will also be accompanied for
the filtration. In this manner, the researchers
obtained maximum amount of crystals needed.
Figure 3. Vacuum filtration setup

Experiment 02 Group 8Nov. 7, 2014

4 of 5

CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

CONCLUSIONS AND RECOMMENDATIONS

% recovery

wt pure acetanilide
100
A
4.30 g
volume H2O
small
100 ml

amount of obtained sample was placed in a

closed capillary tube and was then placed in a
Thomas-Hoover melting apparatus to determine
its melting point. The acquired melting point was
92-104C. It was far from the melting point of
pure acetanilide which is 114.3C. The difference
should be due to the amount of sample in the
capillary tube. The sample may be too few that
was why the sample melted at a lower
temperature. Also, one of the reasons why the
obtained sample was impure was because it had a
wide melting range. The computed percent
recovery of the acetanilide made by the
researchers was different to the actual percent
recovery. This was due to the usage of different
or wrong formula. The proper formula to be used
(Figure 4) will result to a 40.3% recovery of
acetanilide instead of researchers 85.27%
recovery of acetanilide.

Figure 4. Formula for percent recovery of

acetanilide

Overall, the researchers were able to perform the

experiment and determine its objectives although
some of the answers or values needed was
different from the actual answer. This may be due
to inexact use of data and variables. The
researchers may hadnt observed the changes to
be considered in the experiment.
The researchers should follow the instructions
carefully to avoid misconceptions and
misunderstandings. They should pay attention to
small details in experiment like the solubility
behavior and such. In this manner, the
experiment will be done successfully.
REFERENCES
1) Alexandra, A. (2011). Recrystallization. Vol. 2. pp. 9-12.
Northern Virginia Community College. VA: United Stated of
America.
2) Baluyot, J. Y., De Castro, K. Organic Chemistry
laboratory Manual 1 for Chemical Engineering Students.
Experiment 1. pp.4-6.
3) College of Science, Health & the Environment. (2001).
Chem 355. Recrystallization I. pp. 15. Minnesota State
University. Mankato MN: United States of America.
4) Department of Chemistry. (2009). Chem 21. Experiment
9: Recrystallization. pp. 56. Amherst College. Amherst MA:
United Stated of America.
5) PubChem. (2000). Boiling and Melting Points of
Common Organic Compounds. pp. 3-6.

This experiment aimed to identify the appropriate

solvent for the recrystallization technique and to
use the recrystallization technique in purifying a
solid sample. If this experiment will be
performed in the future, the researchers would
carefully observe and wait for the observation of
solubility behavior and will perform the
procedures exactly and step-by-step.

Experiment 02 Group 8Nov. 7, 2014

5 of 5