Purification of Organic Compounds

Purification of Organic
Compounds
• These techniques include:
1. Filtration
2. Centrifugation
3. Crystallization
4. Solvent extraction
5. Distillation
Purification of Organic
Compounds
• These techniques include:
5. Fractional distillation
6. Sublimation
7. Chromatography
8. Steam distillation
9. Sublimation
By Using Filtration
Filtration
• To separate an insoluble solid from a liquid
particularly when the solid is suspended
throughout the liquid
• The solid/liquid mixture is called a suspension
Filtration
The laboratory set-up of filtration

Filtration
• There are many small holes in the filter paper

 allow very small particles of solvent and
dissolved solutes to pass through as filtrate
• Larger insoluble particles are retained on the
filter paper as residue
By Using Centrifugation
Centrifugation
• When there is only a small amount of

suspension, or when much faster
separation is required
 Centrifugation is often used
instead of filtration
Centrifugation
• The liquid containing
undissolved solids is put
in a centrifuge tube
• The tubes are then put
into the tube holders in a
centrifuge
A centrifuge
Centrifugation
• The holders and tubes are spun around at a
very high rate and are thrown outwards
• The denser solid is collected as a lump at
the bottom of the tube with the clear liquid
above
By Using Crystalisation
Crystallization
• Crystals are solids that have

 a definite regular shape
 smooth flat faces and straight edges
• Crystallization is the process of forming
crystals
1. Crystallization by Cooling a Hot Concentrated
Solution
• To obtain crystals from an unsaturated
aqueous solution
 the solution is gently heated to make it
more concentrated
• After, the solution is allowed to cool at
room conditions
Solution
• The solubilities of most solids increase
with temperature
• When a hot concentrated solution is
cooled
 the solution cannot hold all of the
dissolved solutes
• The “excess” solute separates out as
crystals
Solution
Crystallization by cooling a hot concentrated solution

2. Crystallization by Evaporating a Cold Solution
at Room Temperature
• As the solvent in a solution evaporates,

 the remaining solution becomes
more and more concentrated
 eventually the solution becomes
saturated
 further evaporation causes
crystallization to occur
at Room Temperature
• If a solution is allowed to stand at room

temperature,
 evaporation will be slow
• It may take days or even weeks for crystals
to form
at Room Temperature
Crystallization by slow evaporation of a solution (preferably

saturated) at room temperature
By Using Solvent
Extraction
Solvent Extraction
• Involves extracting a component from a

mixture with a suitable solvent
• Water is the solvent used to extract salts
from a mixture containing salts and sand
• Non-aqueous solvents (e.g. 1,1,1-
trichloroethane and diethyl ether) can be
used to extract organic products
Solvent Extraction
• Often involves the use of a separating
funnel
• When an aqueous solution containing
the organic product is shaken with
diethyl ether in a separating funnel,
 the organic product dissolves into
the ether layer
Solvent Extraction
The organic product in an aqueous solution can be extracted by solvent

extraction using diethyl ether
Solvent Extraction
• The ether layer can be run off from the
separating funnel and saved
• Another fresh portion of ether is shaken
with the aqueous solution to extract any
organic products remaining
• Repeated extraction will extract most of
the organic product into the several
portions of ether
Solvent Extraction
• Conducting the extraction with several
small portions of ether is more efficient
than extracting in a single batch with the
whole volume of ether
• These several ether portions are
combined and dried
 the ether is distilled off
 leaving behind the organic product
By Using Distillation
Distillation
• A method used to separate a solvent
from a solution containing non-volatile
solutes
• When a solution is boiled,
 only the solvent vaporizes
 the hot vapour formed condenses to
liquid again on a cold surface
• The liquid collected is the distillate
Distillation
The laboratory set-up of distillation

Distillation
• Before the solution is heated,

 several pieces of anti-bumping
granules are added into the flask
 prevent vigorous movement of the
liquid called bumping to occur during
heating
 make boiling smooth
Distillation
• If bumping occurs during distillation,

 some solution (not yet vaporized)
may spurt out into the collecting
vessel
By Using Fractional
Distillation
Fractional Distillation
• A method used to separate a mixture of
two or more miscible liquids
The laboratory set-up of

fractional distillation
• A fractionating column is attached vertically
between the flask and the condenser
 a column packed with glass beads
 provide a large surface area for the
repeated condensation and vaporization
of the mixture to occur
• The temperature of the escaping vapour
is measured using a thermometer
• When the temperature reading becomes
steady,
 the vapour with the lowest boiling
point firstly comes out from the top of
the column
• When all of that liquid has distilled off,
 the temperature reading rises and
becomes steady later on
 another liquid with a higher boiling
point distils out
• Fractions with different boiling points can
be collected separately
By Using Sublimation
Sublimation
• Sublimation is the direct change of
 a solid to vapour on heating, or
 a vapour to solid on cooling
 without going through the liquid
state
Sublimation
• A mixture of two compounds is heated in an
evaporating dish
• One compound changes from solid to
vapour directly
 The vapour changes back to solid on a
cold surface
• The other compound is not affected by
heating and remains in the evaporating dish
Sublimation
A mixture of two compounds can be separated by

sublimation
3. DISTILLATION
Aim
To separate a solution of a solid in a liquid and for separating a solution of two

liquids whose boiling points are different.
Principle
Distillation involves the conversion of a liquid into its vapors upon heating and
then cooling the vapors back into the liquid. Depending on the difference in
boiling points of liquids.
Types of distillation
 Simple Distillation
 Fractional Distillation
 Distillation Under Reduced Pressure or Vacuum Distillation
 Steam Distillation
41
SIMPLE DISTILLATION
Principle
It is used for separating liquids having boiling points
differing by 10-20 degrees. The liquid having the lower
boiling point distills over first, and the other liquid
component is left behind. In this process, vaporization
and condensation occur side by side.
Process
Example
Simple distillation of a Cyclohexane- Toluene mixtures
42
Video of How Simple
Distillation Works ?
 http://www.youtube.com/watch?v=T4eIc
_v-SrI
43
FRACTIONAL DISTILLATION
Principle
It is used for separating two liquids in any mixture, which
have boiling points within a narrow range of temperatures.
In such cases, simple distillation does not give complete
separation and a modified version called fractional
distillation is employed.
Process
Example
Fractional Distillation of a Cyclohexane- Toluene
mixtures
44
Video of How Fractional
 http://www.youtube.com/watch?v=Z6Oy
NB8V7Hc&list=UUunr-
10Cibvv4CKUBeI_Hkw
45
STEAM DISTILLATION
Principle
This technique is used for separating/purifying liquids,
which are immiscible with water, volatile in steam, & have
high vapor pressure at the boiling temperature of water.
Process
Example
Isolation of Citral
46
Video of How Steam
http://www.youtube.com/watch?v=7g4e3dh
tgjI
47
By Using
Chromatography
Chromatography
• An effective method of separating a

complex mixture of substances
• Paper chromatography is a common
type of chromatography
Chromatography
• A solution of the mixture is dropped at
one end of the filter paper
Chromatography
• The thin film of water adhered onto the surface
of the filter paper forms the stationary phase
• The solvent is called the mobile phase or eluent
Chromatography
• When the solvent moves across the sample spot
of the mixture,
 partition of the components between the
stationary phase and the mobile phase occurs
Chromatography
• As the various components are being
adsorbed or partitioned at different rates,
 they move upwards at different rates
• The ratio of the distance travelled by the
substance to the distance travelled by the
solvent
 known as the Rf value
 a characteristic of the substance
k= Cs
Cm
 K is the partition coefficients of the
components of a mixture between two
immiscible phases - stationary phase
and mobile phase
 Cs is the concentration of the substance in
the stationary phase (Adsorbent)
 Cm is the mobile phase ( Eulent)
By Using Sublimation
2. SUBLIMATION
Aim
To separate volatile solids, which pass directly into vapour
state on heating from a non-volatile solid.
Principle
A mixture of solid substances, such as camphor, benzoic acid,
ammonium chloride, iodine etc., containing non-volatile
substances, when heated, change directly into vapour without
passing through the liquid state.
Process
Fig :-Sublimation
Substance Mp Substance Mp
1,4-dichlorobenzene 55 Benzoic acid 122

Naphthalene 82 Salicylic acid 159
1-Naphthol 96 Camphor 177
Acetanilide 114 Caffeine 235

Purification of Organic Compounds

Uploaded by

Copyright:

Available Formats

Purification of Organic Compounds

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Purification of Organic Compounds

Uploaded by

Copyright:

Available Formats

Purification of Organic

The laboratory set-up of filtration

• There are many small holes in the filter paper

• When there is only a small amount of

• Crystals are solids that have

Crystallization by cooling a hot concentrated solution

• As the solvent in a solution evaporates,

• If a solution is allowed to stand at room

Crystallization by slow evaporation of a solution (preferably

• Involves extracting a component from a

The organic product in an aqueous solution can be extracted by solvent

The laboratory set-up of distillation

• Before the solution is heated,

• If bumping occurs during distillation,

The laboratory set-up of

A mixture of two compounds can be separated by

To separate a solution of a solid in a liquid and for separating a solution of two

This technique is used for separating/purifying liquids,

which are immiscible with water, volatile in steam, & have

high vapor pressure at the boiling temperature of water.

• An effective method of separating a

1,4-dichlorobenzene 55 Benzoic acid 122

You might also like