COURSE TITLE: General Chemistry II

COURSE CODE: CHM 102

TOPIC: Isolation and Purification of Organic Compound

1. Crystallization
2. Sublimation
3. Distillation
4. Fractional distillation
5. Distillation under reduced pressure
6. Steam distillation
7. Extraction with solvents
8. Chromatography

1. Crystallization
This is the process that is most commonly employed for the purification of
solid organic compounds. The impure solid is dissolved in the minimum volume
of a suitable solvent. The soluble impurities pass into the solution while the
insoluble ones are left behind. The hot solution is then filtered and allow to cool
undisturbed till crystallization is complete. The crystals are then separated from
the mother liquor by filtration and drying.
Efficiency of the process of crystallization depends on the scheme with
which the following process are carried out:
 Choice of solvent
 Preparation of solution
 Filtration of hot solution
 Crystallization
 Separation and drying of crystals

2. Sublimation
Some substances when heated, pass directly from the solid state to the
vapour state without melting. The vapour when cooled give back the solid
substances. The process is known as sublimation. This process is helpful in
separating mixture of volatile and non-volatile substances. Substances like
camphor, naphthalene and benzoic acid are separated using this method.

3. Distillation
This operation of distillation is employed for the purification of liquid from
non-volatile impurities. The impure liquid is boiled in a flask and the vapour so
formed are collected and condensed to give back the pure liquid in another
vessel. The non-volatile impurities are left behind in the flask. It is employed
when the differences in boiling point is not less than 60 0C

4. Fractional distillation
A mixture of two or more volatile liquid can be separated by fractional
distillation when their boiling point differ by about 40 0C. The operation can be
 carried out with the help of simple distillation apparatus. The more volatile liquid
passes over first and is collected in a receiver.

5. Distillation under Reduced Pressure

Direct or straight distillation is suitable only for liquid which boil without
decomposition at atmospheric pressure.
In case of organic liquid which decompose before their boiling
point/atmospheric pressure is reached, the distillation is carried out under
reduced pressure when the liquid boils at a lower temperature.
 An important application of the process is the recovery of glycerol from
spent-lye in soap industry.
 Another important application of vacuum distillation is the concentration
of sugar juice under reduced pressure.

6. Steam distillation
Many substances that are insoluble in water and volatile in steam can be
purified by distillation in a current of steam (steam distillation). The non-volatile
impurities are left behind in the distillation flask.
Steam distillation is employed in industries for the recovery of various
essential oil from plant and flowers. It is also used in the manufacture of Aniline
and Turpentine oil.

7. Extraction with solvent

When an organic substance is present as solution in water, it can be
recovered from the solution by the following steps:
 The aqueous solution is shaken with an immiscible organic solvent in
which solute is more soluble
 The solvent layer is separated by means of separating funnel
 The organic substance is then recovered from it by distilling off the
solvent.

8. Chromatography
Chromatography was derived from a Greek word; Chroma which means colour and graphein which means
writing
It was formerly called separation of coloured material but used nowadays
to separate all sort of materials (coloured or colourless). It is based on two
principles:
 Adsorption Chromatography
 Partition Chromatography
In the various types of chromatography, two phases are in contact, that is,
the stationary phase and the mobile phase
Types of Chromatography (Adapted from Lamlad)
Name Abbrevia Stationary phase Mobile
tion phase/Carrier
Paper PC Paper (Water adsorbed in Organic solvent
Chromatography cellulose, an adsorbent)
Thin Layer TLC Silica-gel or alumina in a Organic solvent
Chromatography solvent (an adsorbent)
Column CC A column of finely divided Organic solvent
Chromatography silica-gel or alumina in a
solvent (an adsorbent)
Gas-Solid GSC Column packings such as Inert gas (N2 or
Chromatography silica-gel, charcoal and He or Ar)
molecular sieve (an
adsorbent)
Gas-Liquid GLC Inert supporting material Inert gas (N2 or
Chromatography coated with a non-volatile He or Ar)
liquid, e.g powered fire brick
coated apiezon (a non-
volatile hydrocarbon grease
(an adsorbent))
Note: This table is not part of the lecturer’s note but the content
is.

TEST OF PURITY
A pure organic substance has characteristics physical properties
1. Crystalline form
2. Refractive index
3. Specific gravity
4. Melting point
5. Boiling point
If a given sample of substance shows the property that the pure substance is
known to possess, it may be considered pure. The numerical value of these
properties changes with the nature of the amount of the purity present. In many
laboratories, melting point of a solid substance and boiling point of a liquid
substance is considered a sufficient indication of its purity.

PRACTICE QUESTIONS
1. Crystallization is the process most commonly employed for the purification of
solid organic compound.
2. The efficiency of the process of crystallization depend on the following EXCEPT
A. Choice of solvent
B. Preparation of solution
C. Filtration of hot solution
D. Filtration of cold solution
E. Separation and drying of crystals
3. The process known as sublimation is very helpful in separating Naphthalene
from Sodium chloride (NaCl)
4. The recovery of glycerol from spent lye in the soap industry is an important
application of distillation under reduced pressure
5. Many substance that are insoluble in water and volatile in steam can be purified
by steam distillation
6. Steam distillation is employed in industries for the recovery of various essential
oil
7. How will you purify a solid organic compound?
8. How will you purify a liquid organic compound?
9. Write note on the following:
 Fractional distillation
 Steam distillation
  Solvent extraction
10. How will you separate a mixture of Naphthalene and Sodium chloride
(NaCl)?
Answer:
We can separate Naphthalene from Sodium chloride by sublimation
technique. The Naphthalene sublimes while the Sodium chloride does not
dissolve. A substance is said to sublime on cooling, if its vapour changes
directly from vapour to solid without going through an intermediate state.
Usually, a substance which sublime also changes from solid to vapour
without melting to a liquid. If a mixture of naphthalene and sodium chloride is
heated, the naphthalene turns directly to a vapour but the sodium chloride
remains unchanged. When the vapour is full, solid naphthalene recollect from
sodium chloride.
11. Which of the method is best treated to separate a 500ml sample of two
miscible liquids which boiling point differ by approximately 60 0C.
A. Distillation
B. Fractional distillation
C. Paper chromatography
D. Use of a separating funnel
12. From which of the following mixture will steam distillation be the most
appropriate method of separation.
A. Diethyl, ether and water
B. Ethyl alcohol and water
C. Aniline and sodium chloride
D. None of these
13. Write a note on
 Chromatography
 Column chromatography
 Thin layer chromatography
14. What are the criteria by which the purity of an organic compound may be
established?
15. Indicate whether the following statement are true or false
 Animal charcoal is added to a solution during recrystallization to ensure even
boiling. False
 Sublimation is used for the separation and purification of compounds with
low melting point. False
 The boiling point of a liquid increases as the pressure is reduced. False
 Paper chromatography is used only for the separation of coloured
compounds. False
 An Azeotrope is a liquid mixture of definite temperature which boils at
atmospheric pressure. True

Compiled by Sodiq Akerele