Purification of Organic Compounds by Recrystallization

Waris Shah 23100081

ABSTRACT: the purification technique by recrystallization was performed on five different

organic compounds. The main objective of these experiments was to find what percentage of
the mass of the given compounds consisted of impurities using the purification technique.
INTRODUCTION
During the synthesis of organic/inorganic compounds the products are accompanied by
impurities or by-products. The presence of these impurities can compromise the quality of the
products and can even prevent the products from fulfilling their purpose. The effect of
impurities in pharmaceuticals can be very dangerous as any impurity in a medicine may be toxic
to the consumer. They also cause other undesirable effects such as shortening the shelf life of
substances, decreasing therapeutic effects and even changing the physical and chemical
properties of the substances. The penalty for using fake medicine can be 10 years in prison and
even a life sentence if they caused any grievous harm.1

As honest chemist we want to avoid causing harm to others and being handed a prison
sentence. That’s why there are multiple purification techniques in chemistry to ensure that the
products formed are completely safe to use. Re- crystallization is one of the most important
techniques for the purification of solid organic and inorganic compounds. It involves dissolving
the compound formed along with its impurities in an appropriate solvent. The compound can
then be removed leaving behind the impurities. The solvent is heated to its boiling point and
added to the compound until majority of it is dissolved. This purification method is slow as we
have to find an appropriate solvent for the compound formed and then we have to let it cool
down so that larger crystals of our compound are formed. This technique can only be used for
compounds that are solid at room temperature. It cannot be used for that exist as waxes or oils
at standard conditions. Despite requiring a large amount of time this purification technique has
high efficiency and is preferred more in organic chemistry.2
EXPERIMENTAL SECTION:
Chemicals and materials:
Solvents used:
Water, methanol, hexane, ethyl acetate, ethanol and chloroform.
Five organic compounds used:
- Salicylic acid
- p-toluic acid
- 2-nitro benzoic acid
- 4-bromo benzoic acid
 - 4-Chloro benzoic acid

1.

2.

3.

4.

5.
Fig 1: Organic compounds and their solvents

Glassware and equipment:

Test tubes with rack and holder, water bath, filter paper, beakers (100 and 250 mL), stem
funnel, two Erlenmeyer flasks (50 mL), Buchner funnel, filtration flask, glass rod, spatula,
balance and boiling chips.
PROCEDURE:
1. Finding the appropriate solvent:
A small sample of the organic compound (approximately 20 mg) is taken and added into six test
tubes separately. The six solvents are then added to the test tubes which are then labeled
according to the solvent added. Solubility test is done by first trying to dissolve the compound
in the solvent at room temperature. Add 1ml of solvents to the test tubes. Write down the
names of the solvents which do not dissolve the compound at room temperature. Add boiling
chip to the test tube and heat the mixture to the solvents boiling point. Some solvents such as
ethanol are flammable so heat the test tubes in a water bath. The solvent which does not
dissolve the compound at room temperature but dissolves it at its boiling point is the
appropriate solvent. The same process is repeated for all the five organic compounds to find an
appropriate solvent for them.
2. Purification of products:
After performing the solubility test a sample of the compound was taken in an Erlenmeyer flask
where its mass was measured and recorded. The sample is dissolved in a minimum amount of
hot solvent. The solvent is added slowly until majority if the sample dissolves. Some impurities
may be insoluble and will not dissolve in the solvent. These can be removed from the mixture
by gravity filtration by passing the hot mixture through a filter paper. The impurities are left
behind on the filter paper while the remaining solution is collected in a clean Erlenmeyer flask.3
After all insoluble impurities have been removed the solution is allowed to cool down. Slowly
allowing the solution to cool down forms larger crystals. The crystals start to appear as the
solution cools down to room temperature. If the crystals don’t appear then they can be induced
by lightly scratching the interior of the flask with a glass rod. The glass rod can also be dipped
into the solution then allowed to cool down. When crystals start to form on the rod it can be
inserted into the solution again to induce recrystallization. The newly formed crystals can be
collected by vacuum filtration where the crystals are trapped onto the filter paper.4 These
crystals can be washed with a cold solvent that was used to carry out the purification and then
allowed to air dry to further ensure their purity.
RESULTS AND DISCUSSION:
Table 1: Information on the organic compounds purified

Sr. No Compound Initial Recorded %age Melting point

amount amount (g) recovery (°C)
(g)
1 Salicylic acid 1 0.915 91.5 157-159
2 p-toluic acid 1 0.890 89 177-180
3 2-nitrobenzoic 1 0.850 85 146-148
acid

4 4-bromo 1 0.90 90 252-254

benzoic acid
5 4-Chloro 1 0.891 89.1 238-241
benzoic acid
The percentage yield of the purification was high as the yield for all the compounds was close
to 90%. The results showed that recrystallization is an efficient purification process. The process
required more time but the slow crystallization process through cooling produced larger
crystals.

REFERENCES:
1. Dhikav, V., Fake medicine but real money. BMJ 2006, 333 (Suppl S5).
2. Hekmat, D., Large-scale crystallization of proteins for purification and formulation. Bioprocess
and biosystems engineering 2015, 38 (7), 1209-1231.
3. Chen, J. P.; Chang, S.-Y.; Huang, J. Y.; Bauman, E. R.; Hung, Y.-T., Gravity filtration. In
Physicochemical Treatment Processes, Springer: 2005; pp 501-543.
4. Zuk Jr, P., Systems, apparatus and methods for vacuum filtration. Google Patents: 2010.