2-2

Recrystallization / Filtration
A brief theory and application

Recrystallization / Filtration
Solid compounds synthesized in the Organic laboratory
usually need to be purified before final confirmation tests
are performed.

One of the most commonly used techniques to purify a

sample is Recrystallization followed by Vacuum Filtration.

Recrystallization / Filtration
Background
Recrystallization
1. Solid organic compounds produced in the
laboratory usually need to be purified.
2. The most common technique involves
Recrystallizing the sample from an appropriate
Solvent.
3. The Recrystallization process is a relatively slow
and selective formation of crystals from a solvent.
4. Precipitation is a rapid and nonselective process;
thus not used to purify samples.

Recrystallization / Filtration
Recrystallization (Cont)
5. The Recrystallization Process
a. Dissolve sample in a minimal amount of an
appropriate solvent.
b. Sample should be insoluble in solvent at room
temperature, but soluble at elevated (boiling point)
temperature.
c. If solution is colorized, it is sometimes necessary to
add a decolorizing agent (activated charcoal - Norite)
d. Colorized solutions are first filtered through a fluted
filter or a column containing alumina or silica gel.

Recrystallization / Filtration
Recrystallization (Cont)
5.The Recrystallization Process (Cont)
e. The hot solution is cooled slowly to room temperature.
As the temperature changes the solute particles begin
to come out of solution, leaving the more soluble
impurities in solution.
f. After crystallization, place beaker in water/ice bath.
g. Collect crystals by vacuum filtration.
h. Rinse the crystals with small portion of cold solvent.
i. Dry the crystals in air in your drawer.
j. Determine Melting Point of dried sample.

Recrystallization / Filtration
Recrystallization (Cont)
6. The Appropriate Solvent
a. The solute particles are generally insoluble in cold
solvent, but soluble in hot solvent.
b. The solvent (or mixed solvent) should have a steep
solubility vs temperature curve.
B
Solubility

C
A
Temperature

The C curve is a good solvent

Solute sparingly soluble at room temperature
Solute very soluble at elevated temperature

Recrystallization / Filtration
Recrystallization (Cont)
6. The Appropriate Solvent (Cont)
c. Solubility of organic compounds is a function of
the polarities of both the solvent and the solute:

Like Dissolves Like

Polar solvents dissolve polar solutes

Nonpolar solvents dissolve nonpolar solutes

d. The stability of the solute crystal lattice affects the

solubility. The higher the melting point (higher
stability), the less soluble the solute.

Recrystallization / Filtration
Recrystallization (Cont)
6. The Appropriate Solvent (Cont)
e. The Boiling Point of the solvent must be less than
the Melting Point of the solute.
If the Boiling Point of the solvent is higher than the
melting point of the solute, the solute will Melt
instead of Dissolving in the solvent at the
elevated temperature.
Upon cooling, the Melted solute will Oil out
forming an insoluble mass that is not purified
f. The solvent should not react with the solute
g. Compounds with functional groups that can form
hydrogen bonds (-OH, -NH-, -COOH, -CONH-) will
be more soluble in hydroxylic (polar) solvents such
as Methanol and Water.

Recrystallization / Filtration
7. Solvents in Decreasing Order of Polarity

H2O

- Water

RCOOH

- Organic Acids (Acetic Acid)

RCONH2

- Amides (N,M-dimethylformamide)

ROH

- Alcohols (Methanol, Ethanol)

RNH2

- Amines (Triethylamine, Pyridine)

RCOR

- Aldehydes, Ketones (Acetone)

RCOOR

- Esters (Ethyl Acetate)

RX

- Halides (CH2Cl2 > CHCl3 > CCl4)

ROR

- Ethers (Diethylether)

ArH

- Aromatics (Benzene, Toluene)

RH

- Alkanes (Hexane, Petroleum

Recrystallization / Filtration
Filtration
1. Two Purposes
a. Separate Purified Solid from the Soluble Impurities in
the Solution from which it was Recrystallized.
b. Remove Solid Impurities from a Liquid
2. Two Types
a. Gravity
b. Vacuum
3. Filter Paper
a. Retentivity
Opposite of Porosity; measure
of the
size of particles that can be
retained on
the filter paper.
b. Porosity
Measure of the size of the
particles
than can pass through the
paper.

Recrystallization / Filtration
4. Gravity Filtration Types
a. Filter Cones
into a
extending into

- Folded paper filter inserted

class funnel with stem
a receiving flask.
Applicable Volume > 10 mL.

b. Fluted Filters
creases) filter
funnel
receiving

- Specially folded (many

paper inserted into a class
with stem extending into a
flask.
Applicable Volume > 10 mL

Recrystallization / Filtration
4. Gravity Filtration Types (Cont)
c. Filtering Pipettes
used with
inserted into
constriction.

- Microscale technique
Pasteur Pipets.
A piece of cotton is
the top of the lower
Applicable Volume <

10mL
d. Decantation
supernatant
behind.

- Careful pouring of
liquid into another vessel
leaving solids particles

Recrystallization / Filtration
5. Vacuum Filtration
a. Buchner Funnels
large
solids,

- More rapid than gravity.

- Primarily used to filter
volumes of liquid from
such as crystals from the
Recrystallization

Process.
Applicable Volume > 10
mL.
b. Hirsch Funnels
Buchner
sides.

- Similar, but smaller than

Funnel, with sloping
Used in Microscale

techniques.
Applicable Volume < 10 mL.