CHM142L Organic Chemistry 1 Laboratory

2nd Quarter SY 2013-2014

Recrystallization
Miranda, Marilyn1, Salen, Vladimir, A.2
Miranda, Marilyn, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; 2Salen, Vladimir A., CHM142L/B22, School of Chemical
Engineering, Chemistry and Biotechnology, Mapua Institute of Technology
1

ABSTRACT
In this experiment, we are expected to developed recrystallization techniques and apply them in purifying different organic
compounds commonly used in the laboratory. Recrystallization is the primary method for purifying solid organic compounds.
The impurities may include some combination of insoluble, soluble, and colored impurities. Each is removed in a separate
step in the recrystallization procedure. In order for recrystallization to be effective, the solid and the impurities should have
different solubilities in the recrystallization solvent. The purpose of this experiment is to identify the appropriate solvent for the
recrystallization technique and develop recrystallization techniques and apply them in purifying different organic compounds
commonly used in the laboratory. In this experiment, we dissolve some organic compounds in the cold(room temperature) and
hot(boiling) solvent and determined the solubility. We used hot gravity filtration set-up and vaccum filtration set-up in order to
recrystallize impure acetanilide to recover the pure portion of it and to compute its percent recovery. We slightly failed to
identify the appropriate solvent for the recrystallization technique as we failed to identify the appropriate solvent for
recrystallization for benzoic acid and naphthalene and we also failed to use recrystallization technique in purifying a solid
sample as we obtained 34.3 % of the pure acetanilide from crude or impure acetanilide. It is necessary to used appropriate
solvent for recrystallization because some solute didnt dissolved in solvent while others solute dissolved in solvent but
recrystallization doesnt occur at the end. Taking note that recrystallization works only when the proper solvent is used.
Keywords: recrystallization, percent recovery, impurities, solubility, and solvent

INTRODUCTION
Recrystallization is the primary method for
purifying solid organic compounds. The main foundation
behind recrystallization is the fact that substances will
usually become more soluble when the solvent is hot than
when it is cold. For example, sugar dissolves better in warm
water than in cold water, which is why it is often difficult to
dissolve sugar in iced tea even though a person may stir it
thoroughly. Compounds obtained from natural sources or
from reaction mixtures almost always contain impurities.The
impurities may include some combination of insoluble,
soluble, and colored impurities. To obtain a pure compound
these impuritiesmust be removed. Each is removed in a
separate step in the recrystallization procedure.
In order for recrystallization to be effective, the
solid and the impurities should have different solubilities in
the recrystallization solvent. The difference in solubility at
varying temperatures allows an impure substance to
dissolve at a higher temperature and then crystallize slowly
at a lower temperature without re-trapping the impurities
knowing that for most of solid, solubilities tend to increase
with increasing temperature as their solubilities tend to be
lower in liquid solvents at low temperature. Impurities that
remain undissolved in the solvent are removed by filtration
of the hot mixtures. Soluble impurities remain dissolved

Experiment 02 Group No. 1October 24, 2013

even after crystallization and are therefore separated by

filtration of the cold mixtures.
It is important to select the most appropriate
solvent for recrystallization by looking at the solubilities of
both the solute and the impurities. An ideal recrystallization
solvent should:
a. dissolved all of the compound at high temperature.
b. dissolved very little or none of the compound at low
temperature.
c. have different solubilities for the compound and the
impurities.
d. have a boiling point below the melting point of the
compound.
e. have a relatively low boiling point (60 100 degree
Celsius).
f. be inert with respect to the compound.
g. be relatively inexpensive.
In performing the experiment, the student are
expected to (1) identify the appropriate solvent for the
recrystallization technique and (2) develop recrystallization
techniques and apply them in purifying different organic
compounds commonly used in the laboratory.
MATERIALS AND METHODS

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The experiment has two parts. The first one is

choosing the best solvent appropriate for recrystallization
given the different solutes and the second one is recovering
the pure acetanilide from impure acetanilide using
recrystallization process.
In the first part of the experiment we are using
water, ethanol, benzene and ethyl acetate as solvent while
we are using acetamide, acetanilide, aspirin, benzoic acid,
naphthalene and sucrose as a solute. We also need to use
24 micro test tubes, hot plate and water bath. In choosing
the best solvent appropriate for recrystallization given the
different solutes, we need to dissolve the solute in the
solvent. First, boil a water in the waterbath using hot plate.
Put 2-ml of solvent in a micro test tube. Prepare six per kind
of solvent to be used. Put a little amount of solute in
solvent. Make sure the solution will not become
supersaturated. Do it by putting one kind of solute in
different kind of solvent. Do it one at a time. Record the
observation. If the solute didnt dissolved in solvent at room
temperature, dip the micro test tube containing the solute
and solvent in water in the water bath. Record again the
observation. To identify the solvent that appropriate for
recrystallization, the solvent must follow the characteristics
of ideal solvent for recrystallization.
In the second part of the experiment, we are using
the reagents crude acetanilide and activated carbon while
we are using the apparatuses such as hot plate, watch
glass, analytical balance, beaker, water bath, stemless
funnel, ice bath and Erlenmeyer flask. To recover the pure
acetanilide from crude acetanilide, we need to do it by
filtration. First, prepare a fluted filter paper (cut out a piece
of filter paper into circle with diameter of about five inches.
Fold the circular paper into two, then into four, eight, sixteen
and so on. Open the filter paper). Assemble the Hot gravity
Filtration Set-up (Figure 2.1). Assemble the Vacuum
Filtration Set-up (Figure 2.2). Take note of the weight of the
filter paper. It is also advisable to moisten slightly the filter
paper with the solvent used. Heat approximately 100-ml of
water. Weigh approximately 3.50-g crude acetanilide. Take
note of the exact weight. Then, dissolve the impure
acetanilide in 30-ml of water using 150-ml of beaker. Using
the hot plate, slightly boil the mixture. When the mixture
starts to boil, add 2-ml portions of the previously heated
water with stirring until the white solid completely dissolves.
Maintain the temperature at 90 degree Celsius while adding
hot water. Take note of the total volume of water used. It
should not exceed 70-ml since the solubility of acetanilide is
4.30-g / 100-ml water. If the solution is colored, add a small
amount of activated carbon. Using hot gravity filtration setExperiment 02 Group No. 1October 24, 2013

up, pour the solution into the fluted filter paper situated in
the stemless glass funnel. At this point, you should obtain a
colorless filtrate. If this is not possible, add more activated
carbon then reheat the mixture. Repeat the filtration
process. Remove the flask from the hot plate and discard
the residue. Cool down the filtrate to room temperature,
then place it in an ice bath, and continuously stir the mixture
until crystallization is complete. This process will take
around 10 to 15 minutes. Scratch the side of the flask or
add some crystals of acetanilide if crystallization fails to
occur. Once crystallization is complete, vacuum filter the
solution. Wash the crystals with 2-ml of cold water. Dry the
crystals and weigh them. Compute for the percentage
recovery. Finally, determine the melting point of the purified
crystals.

Figure 2.1 Hot Gravity Filtration Set-up

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2nd Quarter SY 2013-2014

Acetamide
Acetanilide
Aspirin
Benzoic Acid
Napthalene
Sucrose

Col
d
I
S
I
S
S
I

Hot
S
S
I
S
S
S

Acetate
Col
d
Hot
I
S
S
S
S
S
S
S
S
S
S
S

Table 3: Solvent Appropriate for Recrystallization for

Acetamide, Acetanilide, Aspirin, Benzoic Acid, Naphthalene
and Sucrose.

Compound
Figure 2.2 Vacuum Filtration Set-up
http://www.organicchem.org/oc1web/exp/lp/lprecrystal.html

RESULTS
Table 1: Solubilities of Acetamide, Acetanilide, Aspirin,
Benzoic Acid, Napthalene and Sucrose in Water and
Ethanol.
Legend:
S = Solute is soluble in solvent
I = Solute is insoluble in solvent
Compound
Water
Ethanol
Col
Col
d
Hot
d
Hot
Acetamide
S
S
S
S
Acetanilide
I
S
S
S
Aspirin
I
S
S
S
Benzoic Acid
I
I
S
S
Napthalene
I
I
S
S
Sucrose
S
S
I
I
Table 2: Solubilities of Acetamide, Acetanilide, Aspirin,
Benzoic Acid, Napthalene and Sucrose in Benzene and
Ethyl Acetate
Legend:
S = Solute is soluble in solvent
I = Solute is insoluble in solvent
Compound
Benzene

Experiment 02 Group No. 1October 24, 2013

Ethyl

Acetamide
Acetanilide
Aspirin
Benzoic Acid
Naphthalene
Sucrose

Solvent
Appropriate
for
Recrystallization
Benzene , Ethyl
Acetate
Water
Water
Water
Ethyl Acetate
Benzene

Table 4: Data Obtained upon Doing Recrystallization of

Impure Acetanilide.
Weight of crude acetanilde
in grams
Weight of the filter paper in
grams
Weight of the pure
acetanilide in grams
Volume of water used in ml
Melting point of pure
acetanilide in Celsius
Percentage recovery

3.51
1.14
0.59
40
112116
34.3

DISCUSSION

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The criteria in selecting good recrystallization

solvent are: (a) The substance to be purified must have a
high solubility in the solvent at its boiling point, and a
significantly diminished solubility at lower temperatures.
Obviously, the first part is necessary so that you can get the
material into solution, and the second part is required so
that the purified compound will come back out of solution.
(b) The solvent should dissolve the impurities at all
temperatures. The important point here is that purification
will be accomplished only if the impurities remain in solution
as the mixture is cooled. This isn't too hard to accomplish if
the amount of impurity is small. Obviously, it's a bit more
difficult if a large amount of an impurity is present, but if the
solubility characteristics of the desired substance are
sufficiently different from the impurity, as is often the case, a
suitable solvent can usually be found. (c) The solvent must
not react with the substance to be purified. It's hard to get
your compound to come back out of solution when it is
consumed by a reaction. (d) A reasonably volatile solvent is
preferred. This consideration is dictated by the need to
ultimately remove traces of solvent from the crystals, and
this is most easily accomplished by evaporation, either at
room temperature or in an oven. Even with an oven to aid in
the drying, only moderate temperatures can be used, since
you should stay below the melting temperature of the solid,
and definitely below temperatures where the material will
decompose. (e) Ideally, the solvent should be inexpensive,
non-toxic, and non-flammable. These are not absolutely
required, but desirable characteristics, which can help to
determine the choice of a solvent. Obviously, water is an
ideal choice based on these criteria. That are the reasons
based on Table 3 why benzene and ethyl acetate is best
solvent for recrystallization of acetamide, water is best
solvent for recrystallization of acetanilide, aspirin, benzoic
acid, and benzene is the best solvent for recrystallization of
sucrose and naphthalene.
Table 3: Solvent Appropriate for Recrystallization for
Acetamide, Acetanilide, Aspirin, Benzoic Acid, Naphthalene
and Sucrose.

Compound

Acetamide
Acetanilide
Aspirin
Benzoic Acid

Solvent
Appropriate
for
Recrystallization
Benzene , Ethyl
Acetate
Water
Water
Water

Experiment 02 Group No. 1October 24, 2013

Naphthalene
Sucrose

Benzene
Benzene

It is necessary to use appropriate solvent for

recrystallization because some solute didnt dissolved in
solvent while others solute dissolved in solvent but
recrystallization doesnt occur at the end. Taking note that
recrystallization works only when the proper solvent is
used.
In performing recrystallization there many
reminders to remember. It is important to used minimum
amount of solvent to dissolved the solute for
recrystallization to account for evaporation during the
heating, and to allow for the small amount of cooling which
will occur. A fluted filter paper is used during the hot
filtration step because a fluted paper uses the entire surface
area of the filter paper to filters more rapidly than the
conventional conical fold. A stemless glass funnel is used
during the hot filtration step because it is susceptible to
clogging by formation of crystals, so a stemless funnel is
used. The solution from the hot filtration step is not
immediately placed in the ice bath for cooling because toorapid crystallization generally leads to smaller, more poorly
formed (and less pure) crystals. The vacuum filtration is
used during the cold filtration step because this technique
permits fast and efficient removal of the mother liquor. The
mother liquors are rapidly drawn into the filter flask by
suction, and the crystals are squeezed dry of solvent by
pressing with a clean cork while drawing air through them.
Lastly the cold crystals are washed with water because
solvent is added to just cover the crystals in the funnel (this
solvent can be used to rinse the last few crystals out of the
crystallization flask). The crystals should be stirred gently
with a glass rod or a spatula so that all come in contact with
the wash liquid, then the vacuum is restarted and the
crystals sucked and pressed dry as before. In some cases,
it may be necessary to repeat the wash a 2nd time. Air is
drawn through the crystals until they are as dry as possible,
at which time they are spread on a watch glass for further
drying in the air or in an oven.
The best way to remove insoluble material is to
filter the hot mixture, while the desired material is dissolved.
Insoluble debris will be trapped on the filter paper. The
colored, resinous impurities are usually large, relatively
polar organic molecules which have a strong tendency to
be adsorbed on surfaces. Crystals grown from solutions
containing such resins are often discolored by surface

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contamination by these materials, and it is therefore

desirable to also remove them from the solution before
recrystallization. They can be taken care of by addition of a
small amount of powdered, activated charcoal to the hot
solution before filtering. Decolorizing carbon has a huge
surface area, and readily absorbs the colored impurities.
The hot filtration then removes the charcoal; the filtrate,
now free of this contamination, is allowed to cool and
deposit crystals.
Cooling the filtrate in an ice bath is also necessary
because cooling in an ice-water bath will cause additional
crystallization. Crystals come in a variety of shapes and
sizes: long needles, blocky prisms, and flat plates are
common. Slow crystal growth not only gives the most
pleasing display; the product is generally purer. Too-rapid
crystallization generally leads to smaller, more poorly
formed (and less pure) crystals.
CALCULATIONS
To calculate for the percent recovery of pure
acetanilde we need to the formula:
=

Weight of pure acetanilide recovered x 100%

Total volume used x solubility of acetanalide

Based on the data obtained given in the table 4:

Weight of pure acetanilide recovered = 0.59 grams
Total volume used = 40 ml
Solubility of acetanilide = 4.30 gram per 100 ml
Percent Recovery
=
0.59 grams x 100 %
40 ml x (4.30 gram / 100 ml)
= 34.3 %
The percent recovery of pure acetanilide is 34.4%
which means there was a large amount of pure acetanilide
lost and the recovery was failed.
CONCLUSIONS AND RECOMMENDATIONS
In the experiment, it slightly failed to identify the
appropriate solvent for the recrystallization technique as we
failed to identify the appropriate solvent for recrystallization
for benzoic acid and naphthalene. According to the date we
gathered in the experiment, benzene and ethyl acetate is
the appropriate solvent for recrystallization for acetamide,
water is the appropriate solvent for recrystallization of
acetanilide and aspirin while benzene is the appropriate

Experiment 02 Group No. 1October 24, 2013

solvent for sucrose as the solute is insoluble in cold solvent

while it is completely dissolved in hot solvent. In dissolving
solute in the solvent it also follow like dissolved like, water
is the appropriate solvent for recrystallization of benzoic
acid as it is insoluble in cold water but soluble in the hot
water. Benzoic acid also is a polar molecule that why it is
dissolved in water because water is also a polar molecule.
On the other hand, benzene is the appropriate solvent for
recrystallization of naphthalene as it is insoluble in cold
benzene but soluble in hot benzene. Benzene and
naphthalene is a non-polar molecule that why naphthalene
dissolved in benzene. Possible reasons why identification of
appropriate solvent for recrystallization fails are solute is not
properly heated in the water bath and shake after being
heated and too much solute added to the solvent that cause
supersaturated solution.
It is also failed to use recrystallization technique in
purifying a solid sample as we obtained 34.3 % of the pure
acetanilide from crude or impure acetanilide. Possible
reason why recovering of pure acetanilide fails are
immediate placing of solution to ice bath, too much solvent
used, not scratching the side of the container, not using
activated carbon if the solution is colored and too much
activated carbon used .
To avoid errors in identifying appropriate solvent
for recrystallization of given compounds, I recommend that
to follow the general rules like dissolved like and to heated
properly the mixture properly to dissolved the solute in the
solvent.
To recover high percentage of pure acetanilide, I
recommend to weigh the substance and filter paper before
crystallization, to slow down the cooling of a hot, saturated
solution to room temperature or below, slow down the
evaporation of the solvent at room temperature in an open
vessel, to scratch carefully the inner surface of the vessel
with a glass rod, to wash the crystals with cold solvent of
the same composition as the mother liquor, to use hot
gravity, to used vacuum filtration, to use activated carbon if
the solution is colored, avoid immediate cooling of the
solution and to follow procedure in the manual carefully.
REFERENCES
1. Baluyot, J.Y. G. and De Castro, K. Organic Chemistry
Laboratory Manual for Chemical Engineering Students, Part
1, Mapua Institute of Technology, Manila, Philippines

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2. Clayden J., Greeves N., Warren S. and Wothers P.

(2001). Organic Chemistry, Oxford University Press, United
States

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