Identification of

organic compounds using

Recrystallization

Ali Hussein Sabr, Mustafa Abd Alsalaam|

Pharmaceutical Chemistry |
Supervised by: Assist. Prof. Dr. Karima Fadhil Ali
 Introduction
In chemistry, recrystallization is a technique used to purify chemicals. By dissolving a
mixture of a compound and impurities in an appropriate solvent, either the desired
compound or impurities can be removed from the solution, leaving the other behind.
It is named for the crystals often formed when the compound precipitates out.

Recrystallization is a procedure for purifying compounds. The most typical situation

is that a desired "compound A" is contaminated by a small amount of "impurity B".
Various methods of purification may be attempted, recrystallization being one of
them. Different recrystallization techniques can be used such as:

Single-solvent recrystallization
Typically, the mixture of "compound A" and "impurity B" is dissolved in the smallest
amount of hot solvent to fully dissolve the mixture, thus making a saturated
solution. The solution is then allowed to cool. As the solution cools the solubility of
compounds in the solution drops. This results in the desired compound dropping
(recrystallizing) from the solution. The slower the rate of cooling, the bigger the
crystals form.

In an ideal situation the solubility product of the impurity, B, is not exceeded at any
temperature. In that case, the solid crystals will consist of pure A and all the
impurities will remain in the solution. The solid crystals are collected by filtration
and the filtrate is discarded. If the solubility product of the impurity is exceeded,
some of the impurities will co-precipitate. However, because of the relatively low
concentration of the impurity, its concentration in the precipitated crystals will be
less than its concentration in the original solid. Repeated recrystallization will result
in an even purer crystalline precipitate. The purity is checked after each
recrystallization by measuring the melting point, since impurities lower the melting
point. NMR spectroscopy can also be used to check the level of impurity. Repeated
recrystallization results in some loss of material because of the non-zero solubility of
compound A.

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The crystallization process requires an initiation step, such as the addition of a "seed"
crystal. In the laboratory, a minuscule fragment of glass, produced by scratching the
side of the glass recrystallization vessel, may provide the nucleus on which crystals
may grow. Successful recrystallization depends on finding the right solvent. This is
usually a combination of prediction/experience and trial/error. The compounds must
be more soluble at higher temperatures than at lower temperatures. Any insoluble
impurity is removed by the technique of hot filtration.

Multi-solvent recrystallization
This method is the same as the above but where two (or more) solvents are used.
This relies on both "compound A" and "impurity B" being soluble in a first solvent. A
second solvent is slowly added. Either "compound A" or "impurity B" will be
insoluble in this solvent and precipitate, whilst the other of "compound A"/"impurity
B" will remain in solution. Thus the proportion of first and second solvents is critical.
Typically the second solvent is added slowly until one of the compounds begins to
crystallize from the solution and then the solution is cooled. Heating is not required
for this technique but can be used.

The reverse of this method can be used where a mixture of solvents dissolves both A
and B. One of the solvents is then removed by distillation or by an applied vacuum.
This results in a change in the proportions of the solvent causing either "compound
A" or "impurity B" to precipitate.

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 Hot filtration-recrystallization
Hot filtration can be used to separate "compound A" from both "impurity B" and
some "insoluble matter C". This technique normally uses a single-solvent system as
described above. When both "compound A" and "impurity B" are dissolved in the
minimum amount of hot solvent, the solution is filtered to remove "insoluble matter
C". This matter may be anything from a third impurity compound to fragments of
broken glass. For a successful procedure, one must ensure that the filtration
apparatus is hot in order to stop the dissolved compounds from crystallizing from
the solution during filtration, thus forming crystals on the filter paper or funnel.
One way to achieve this is to heat a conical flask containing a small amount of clean
solvent on a hot plate. A filter funnel is rested on the mouth, and hot solvent vapors
keep the stem warm. Jacketed filter funnels may also be used. The filter paper is
preferably fluted, rather than folded into a quarter; this allows quicker filtration, thus
less opportunity for the desired compound to cool and crystallize from the solution.
Often it is simpler to do the filtration and recrystallization as two independent and
separate steps. That is dissolve "compound A" and "impurity B" in a suitable solvent
at room temperature, filter (to remove insoluble compound/glass), remove the
solvent and then recrystallize using any of the methods listed above.

Aim of experiment
The purpose of recrystallization is to separate or remove the impurities in a solid
compound that are dissolved in a solvent to obtain a pure compound.

Procedure
1. Weigh out approximately 0.5 grams of impure unknown using a spatula and
place it in a clean, dry, and heat-resistant flask.
2. Add a minimal amount of solvent to the flask, just enough to dissolve the
unknown. Be sure to use a solvent that unknown is soluble in when it's hot but not
when it's cold. Water can be used as a solvent.
3. Heat the mixture gently using a hot plate until the unknown dissolves
completely. Be careful not to overheat the mixture.

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 4. Add small amount of activated charcoal, and return the flask to the heater.
5. Remove the flask from the heat source and let it cool slowly. You can leave it on
the hot plate with the heat turned off or let it cool naturally to room temperature.
The slow cooling will encourage the formation of pure crystals.
6. Once the mixture is at room temperature, place the flask in an ice bath to further
encourage crystallization.
7. Once the crystals have formed, use a glass stirring rod to scratch the sides of the
flask to initiate crystallization. Avoid disturbing the crystals too much as they will be
delicate.
8. Set up funnel and filter paper.
9. Transfer the crystals to the funnel.
10. Allow the crystals to dry completely.
11. Once the crystals are dry, transfer them to a watch glass or weighing paper and
weigh them.
12. Determine the melting point of the unknown using a thermometer and compare
it to the literature value to confirm its purity.

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 Result
1- Dissolve the unknown in a suitable solvent and heat up the mixture.

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2- Filter the mixture while it is still hot.

3- Let the solution cool down to room temperature and then place
the flack in an iced water

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3- Filter the mixture to obtain pure crystals of the unknown

4- Dry the crystals then weight them and determine the unknown
using the Melting Point method of identification.

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Discussion
Recrystallization is a common purification technique used in chemistry to
separate impurities from a solid sample. In a typical recrystallization experiment,
an impure solid sample is dissolved in a hot solvent, and the solution is then
allowed to cool slowly to encourage the formation of pure crystals.

The recrystallization process works on the principle of solubility. The solubility of

most solids increases as the temperature of the solvent increases. When a solute
is dissolved in a hot solvent, the solution is saturated with the solute. As the
solution cools, the solubility of the solute decreases, leading to the formation of
crystals. The impurities in the sample are often less soluble than the desired
product and therefore remain in solution, leaving behind a pure product.
One important aspect of a recrystallization experiment is the choice of solvent.

The ideal solvent should dissolve the impure solid sample readily at high
temperatures but should be relatively insoluble at lower temperatures. The
solvent should also not react with the solute or any impurities present in the
sample. Additionally, the solvent should have a relatively low boiling point to
facilitate easy removal from the pure product.
During the experiment, the solubility of the solid sample is tested in different
solvents to determine the most appropriate solvent for the recrystallization
process. The solvent is then heated, and the solid sample is added in small
portions until it no more dissolves. The solution is then allowed to cool slowly,
and crystals of the pure product are collected by filtration. The collected crystals
are then washed with a small amount of cold solvent to remove any remaining
impurities before being dried.
The success of a recrystallization experiment can be evaluated by measuring the
melting point of the pure product. A pure compound will typically have a sharp
melting point, while impurities will lower the melting point range and cause it to
be broader.

In summary, recrystallization is a useful technique for purifying solid samples in

chemistry. The choice of solvent is critical for the success of the experiment, and
the purity of the product can be evaluated by measuring its melting point.

The success of this experiment depends on several factors, including the choice of
solvent, the purity of the starting material, and the careful control of temperature
during the recrystallization process. A suitable solvent should dissolve the
impure unknown completely when heated, but not dissolve the pure unknown

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when the solution cools down. If the solvent dissolves both impurities and the
pure compound equally well, the recrystallization will not be successful.

During the recrystallization process, it is important to control the rate of cooling

to ensure the formation of pure crystals. Slow cooling helps to promote the
formation of large, well-defined crystals while rapid cooling can lead to the
formation of small, poorly defined crystals that may still contain impurities.

Once the crystals have formed, the next step is to filter them out of the solution
using a vacuum filtration setup. It is important to use filter paper with a small
pore size to ensure that all of the crystals are captured and that no impurities
pass through the filter. The crystals should then be washed with a cold solvent to
remove any remaining impurities that may be adsorbed on the surface of the
crystals.
Finally, the purified crystals are dried and weighed to determine the yield of the
recrystallization. The purity of the crystals can be confirmed by comparing the
melting point of the purified unknown to the literature value. If the melting point
is significantly lower or higher than the literature value, it suggests that the
sample may still contain impurities.

Activated charcoal can be used in this experiment to remove impurities from the
unknown solution before recrystallization. Activated charcoal is a highly porous
material that can adsorb a wide range of organic and inorganic compounds,
including impurities in the unknown solution. By adding activated charcoal to
the solution, impurities can be removed through adsorption onto the surface of
the charcoal particles.
The addition of activated charcoal is particularly useful when the impurities in
the unknown solution are colored or have strong odors, as activated charcoal can
effectively remove these compounds from the solution. This can help to increase
the purity of the final product and improve the yield of the recrystallization
process.
To use activated charcoal in this experiment, a small amount of activated
charcoal is added to the impure unknown solution, and the mixture is heated and
stirred for a short period of time to allow the impurities to adsorb onto the
charcoal particles. The mixture is then filtered through a filter paper to remove
the charcoal and impurities, leaving behind a solution containing purified
unknown that can be recrystallized using a suitable solvent.

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