CHM142L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

Recrystallization
Terrado, Rence Christian L.

Professor Marilyn Miranda, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; Bote,Jairus Lemuel ; Brillas, Catherine Jill
1

CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology

ABSTRACT
One of the best purifying techniques is through recrystallization. The experiment entitled
Recrystallization aims to show of what solvents will best fit the given solute(i.e. benzene for
acetamide) and on how to recrystallize impure compounds such as crude acetanilide to pure
acetanilide. The said technique is used in the experiment. In this technique, impure solid (Crude
Acetanilide) was dissolved in enough warm water and then cooled allowing the molecules to
crystallize then immersed in a cold water bath forming more crystals. The molecules of the other
compounds dissolved in solution are excluded from the growing crystal lattice, giving a pure solid.
Pure acetanilide crystal was obtained by vacuum filtration and drying. An effective
recrystallization can be observed by its narrow melting point and higher percent recovery. Impure
compounds relatively have wider melting point range and have low percent recovery.
The group obtained high percent recovery 101.39 due to improper handling of the compound and
due to its wetness causing higher weight for the compound. The solubility of acetamide,
acetanilide, aspirin, benzoic acid, naphthalene and were determined by dissolving them in the
following solvents: cold ethanol, cold water, benzene and ethyl acetate. By doing so, the most
appropriate solvent for the given organic compounds were chosen by considering a criteria in
choosing one. As a result, Benzene solvent was suitable for acetamide and aspirin. Water was
best for acetanilide, Benzoic Acid, and Naphthalene and Ethanol solvent was best for Sucrose
solute. Overall experiment was fine, data obtained was according to the objectives and have met
them. The experiment aims to to identify the appropriate solvent for recrystallization technique
and to use recrystallization technique to purify a solid sample.

Keywords: Recrystallization, Solubility, Solvent, Impurities, Purities,

INTRODUCTION Crystallization is the deposition of crystals from

Recrystallization is a common method of
purifying organic substances through the
difference in solubility at different temperature.
Solubility is the degree of substance which is
the solute to be dissolved in solvent. It is the
main factor that affects crystallization. Before
performing crystallization, identifying
recrystallizing solvent is important. The
substance to be crystallized should show the
ideal solubility behaviour in the given solvent.
A substance can be purified when both the
desired substance and the impurity have
similar solubility at its boiling point
temperature, and when the impurity represents
only a small fraction of total solid. The desired
substance will crystallize on cooling, but the
impurities will not.
a solution. Organic compounds that are solid at
room temperature are usually purified by
crystallization. Crystallization of a solid is not
the same as precipitation of a solid. In
crystallization, there is a slow, selective
formation of the crystal framework resulting in
a pure compound. In precipitation, there is a
a rapid formation of a solid from a solution that
usually produces an amorphous solid
containing many trapped impurities within the
solid's crystal framework. For this reason,
experimental procedures that produce a solid
product by precipitation always include a final
recrystallization step to give the pure
compound. During the process of crystal
formation, a molecule have the tendency to be
attached to a growing crystal composed with
the same type of molecules because of a
better fit in a crystal lattice of a molecule of
the same structure than for other molecule.

Experiment 02 Group No. 4 Date 11/07/14 1 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015

Lattice is a fixed and rigid arrangement of particles were dissolved. Using the hot gravity
atoms, molecules or ions. Recrystallization is a filtration set up, pouring the solution into the
method in which two crystallization processes fluted filter paper situated in the stem-less
was performed. It is referred to the second funnel was the next step. The Erlenmeyer flask
crystallization. It depends on the difference of was removed and the residue was discarded
solubility of a substance in a hot and in a cold when the filtration stops. Placing the filtrate
solvent. The aim of this experiment entitled after cooling at room temperature was done
Recrystallization is to identify the appropriate until crystallization is complete. When the
solvent for recrystallization technique and to crystallization stopped, vacuum filtering the
use recrystallization technique to purify a solid solution was the next step. And crystals were
sample. washed with 2 mL cold water. Dried crystals
were obtained by heating approximately 100
degree Celsius in the oven and then weighed
the crystals. Melting point was obtained using
the Thomas Hoover Melting point apparatus
MATERIALS AND METHODS
and then submitted the crystals to the
instructor.
. In experiment 2 part 1 entitled Choice of
Solvent, the group tested the compounds:
acetamide, acetanilide, aspirin, benzoic acid,
naphthalene, and sucrose to what is their
choice of solvent. What solvent makes them
soluble and what does not. The procedures to
this experiment are preparing first the cold
water and hot water bath by heating distilled
water on a hot plate until the water boils. While Figure 1. Fluted Filter paper
waiting for the hot water bath to boil, 0.10
grams of the given solute was weighed then
placed in a micro test tube then labelled it.
Observing the solubility behaviour of the given
solute/s on the cold water is the next step. If it
fails to dissolve, boiling of the given solute
immersed in cold water in the water bath is
needed and observe its solubility behaviour
whether it is soluble or not. Recording
observations is needed for further
explanations.

In experiment 2, part 2 entitled

Recrystallization of Pure Compounds tested the
crude acetanilide to recrystallize it to remove
its impurities. The first step was to prepare the
following set ups: the Hot Gravity Filtration set
up and the Vacuum Filtration set up. Preparing Figure 2: Hot Gravity Filtration Set-up
also a fluted filter paper was needed and was
given by the laboratory assistant.
Approximately 3.50 grams of crude acetanilide
was weighed while preparing boiled 100-mL
distilled water. The crude acetanilide was
dissolved by adding 30 mL of distilled water
and adding 10 mL at a time until enough white
acetanilide is dissolved. Using the hot plate,
mixture was boiled and when it starts to boil,
the group added 2-mL portions of the
previously heated water until white solid

Experiment 02 Group No. 4 Date 11/07/14 2 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015

Crude Ethanol
Acetanilide

Distilled Water

RESULTS and DISCUSSIONS

The data obtained from the part 1 of the

experiment is shown in tabular form below:

Table 3: Choice of Solvents

Compound Water Ethanol Benzene Ethyl

Acetate
Figure 3: Vacuum Filtration Set-up
Cold Hot Cold Hot Cold Hot Cold Hot

Acetamide S S S S I S S S
(Table 1. List of apparatuses used)
Acetanilide I S I I S S S S

Thomas-Hoover Buchner Beaker

Aspirin I I S S I S S S
Melting Point Funnel
Apparatus
Benzoic I S S S S S S S
Acid
Stemless Funnel Micro test Capillary
tubes tubes
Naphthalene I S S S S S S S
Hot plate Funnel Oven
Support Sucrose S S I S I I S S

Table 4. Solvent Appropriate for Recrystallization of the

Test tube rack Erlenmeyer Given Solutes
Flask

Compounds/Solute Solvent Appropriate

for Recrystallization
(Table 2. List of reagents used)
Acetamide Benzene

Acetamide Benzoic Acetanilide Water

Acid
Aspirin Benzene
Acetanilide Ethyl
Acetate
Benzoic Acid Water
Aspirin Naphthalen
Naphthalene Water
e

Sucrose Ethanol
Benzene Sucrose

Experiment 02 Group No. 4 Date 11/07/14 3 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015
The first consideration in purifying a solid by
recrystallization is to find a suitable solvent. In
selecting the right solvent for the solute given
for recrystallization, here are the following
requirements to consider. First is purified
compound must be very soluble in hot solvent
and almost insoluble in cold solvent. Next is it
dissolves the impurities completely at room
temperature. Third is the solvent must not
react with substance to be purified. Fourth is
the solvent must be cheap, non-flammable and
non-toxic. Fifth is it must be a volatile solvent
(Low Boiling point) and can be easily removed
through evaporation. And the last is it should
have boiling point lower than the melting point
of the solid to be purified. In choosing the right
solvent will dissolve a large amount of the
impure compound at temperatures near the
boiling point of the solvent. Small amount of
compound being purified should remain in
solution at low temperatures because low
solubility at low temperatures minimizes the
amount of purified compound that will lose
during recrystallization. Another important
criterion for selecting a recrystallizing solvent
relates to recovery of the compound. An
abundant quantity of crystals must be
produced as the solution cools to room
temperature or below. From table 4, water is
the appropriate solvent for recrystallization of
Acetanilide, Benzoic acid and Naphthalene.
From the first table, these three compounds
are insoluble in cold water but soluble in hot
water. The criteria mentioned above earlier
were also met. And also, water is relatively less
expensive and is relatively available
everywhere thus, the losses are not costly. For
the compounds Acetamide and Aspirin,
Benzene is the suitable solvent. From table 1, it
can be deduced that the only solvent where
these compounds are insoluble in low
temperature is benzene, which is a crystallize from the solution. After the flask has
characteristic of a good solvent. Other
requirements mentioned were also met by
Benzene for these compounds. Ethanol is the
appropriate solvent for Sucrose because the
Experiment 02 Group No. 4 Date 11/07/14
compound was insoluble in low temperature
and was eventually dissolved when heated in a
warm bath. Ethanol also met the latter criteria.
In the part 2 of the experiment entitled
Recrystallization of pure compounds,
acetanilide was recrystallized through many
steps. From crude acetanilide to pure
acetanilide crystals formed. 3.52 grams of
crude acetanilide was weighed for the
experiment. Dissolving the crude acetanilide
with small amount of solvent like 30 mL then
adding 10 mL solvent at a time is very
important because the compounds solubility
at room temperature is not zero. The Gravity
Filtration set up (see Figure 2) is needed to
heat because of preventing pre-mature
precipitation of the solid in the funnel. After
filtration, the mother liquor is saturated in your
compound (in the real world, this solvent is
often concentrated and refiltered to collect
second, third, fourth etc. crops of crystals
and maximize yield). Using too much solvent
will get less product crystallizing out later. The
more solvent, more products will be lost. Fluted
paper allows the liquid to pass through it very
quickly and gives a lot of surface area on which
collect the solid impurities. Stem less funnel is
used because crystals can form in the cool
stem of a long-stem funnel and clog it. It is
important that the glass setup is warm before
starting the filtration. When most of the solvent
has gone through the funnel, the filter paper is
washed with a few milliliters of fresh, hot
solvent and the setup is allowed to cool. After
the insoluble impurities have been removed,
cover the flask containing the hot filtrate with a
watch glass and set it aside undisturbed to cool
slowly to room temperature. As the solution
cools, the solubility of the dissolved compound
will decrease and the solid will begin to
cooled to room temperature, it may be placed
in an ice bath to increase the yield of solid. Do
not rapidly cool the hot solution by placing the
flask in an ice bath before it has cooled to room
4 of 5
 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015
temperature-this will result in a rapid
precipitation of the solid in an impure form
because of trapped impurities. Activated
Carbon can be added when the filtrate is not
colourless. Activated carbon is used to remove
coloured soluble impurities by the coloured
substances attaching to the carbon by
Adsorption. Adsorption is the adhesion of
atoms, ions, or molecules from a gas, liquid, or
dissolved solid to a surface. Vacuum Filtration
is needed (see Figure 3) to remove the soluble
impurities from the wet crystals after cooling
and transferred to a filter paper. Cold crystals
are washed with small amounts of water to
gain more crystals for observation.
Figure 4: Steps in Removing impurities in Acetanilide
Data and results of computations are shown in
the table
Table 5: Recrystallization of Pure Acetanilide
Weight of Crude Acetanilide, g
Weight of filter paper, g
Weight of Pure Acetanilide, g
Volume of water used, mL
Melting point of pure
Acetanilide, C
Percentage Recovery, %
Experiment 02 Group No. 4 Date 11/07/14
The group obtained large weight of pure
acetanilide which leads to high percentage
recovery, due to wetness of the crystals from
the oven which conducts errors.
CONCLUSIONS AND RECOMMENDATIONS
The group obtained data closest to the true
values except for part 2 which indicates error
due to the handling of compounds. The group
did identify which solvent best suits the
recrystallization of the give solutes and the
group did well the recrystallization of impure
acetanilide but conducts error in the final
record. At the end of the experiment, the
criteria were helpful in identifying which
solvent is suitable for the given solutes. Certain
recrystallization techniques were also used in
purifying a solid sample. To refrain from error
and obtain the correct melting point range, one
recommendation is to make sure that the
sample should be firmly packed in the bottom
of the tube to ensure efficient heat transfer.
REFERENCES
1. Soderberg, T (n.d.) Organic Chemistry With
a Biological Emphasis (University of Minnesota,
Morris)
2. Samuel H. Yalkowsky , Joseph F.
Krzyzaniak , Paul B. Myrdal Ind. Eng.
Chem. Res., 1994, 33 (7), pp 18721877
3. Chang, R. (2008). General Chemistry: The
Essential Concepts (5th Ed.). NewYork:
3.52
McGraw-Hill.
1.15
4. Mullin, J. W. (1961). Crystallization. London,
England: Butterworth & Co.
2.18
50
113-
114
101.3
9
5 of 5