RECRYSTALLIZATION

RECRYSTALLIZATION
to crystallize again
purification technique which is based
on changes of solubility at different
conditions (i.e. temperature)

SOLUBILITY AND
TEMPERATURE
Solubility is affected by
Nature (polarity) of the solute and
solvent
Like dissolves like

Temperature
Solubility Temperature

Solubility intensive property

Different substances have different
solubility in the same solvent

EXPERIMENT 4:
RECRYSTALLIZATIO
N

Selection of the
Recrystallizing
Solvent

Synthesis of
Acetanilide

Purification by
Recrystallization

CRITERIA FOR SELECTING THE

RECRYSTALLIZING SOLVENT
Substance of interest has variable
solubility at different conditions
(temperature)
Impurities are highly soluble in the
recrystallizing solvent
Does not react with the substance of
interest
Non-toxic

SELECTING THE
RECRYSTALLIZING SOLVENT

Solvent

Room
Temperature

Hot H2O
Bath

Ice Bath

dH2O

Insoluble

Soluble

Insoluble

Hexane

Insoluble

Insoluble

Insoluble

Ethanol

Soluble

Soluble

Soluble

SYNTHESIS OF
ACETANILIDE
+
Aniline

Acetic
anhydride

+
Nphenylacetamide
/
acetanilide

N-acylation
Nucleophilic Aromatic
Substitution

Acetic
acid

THEORETICAL YEILD
Maximum theoretical amount (in
grams) of product that can be
produced from the reaction
Dictated by the LIMITING REAGENT
the reagent which is completely
consumed at the end of the reaction

DETERMINATION OF THE
LIMITING REAGENT AND THE
THEORETICAL YIELD

Amount

of acetanilide that can be

produced from:
2.0 ml of aniline

3.0 ml of acetic anhydride

SOLUBILITY
Like dissolves like
Some organic compounds exhibit
partial solubility
temperature, solubility

ACETANILIDE/N-PHENYL
ACETAMIDE
Functional groups
Phenyl (hydrophobic)
Amido (hydrophylic)

Slightly soluble in water

RECRYSTALLIZATION IN THE
PURIFICATION OF ACETANILIDE
Synthesis of acetanilide produces:
Acetanilide (slightly soluble in water)
Acetic acid (soluble in water)
Co-product of acetanilide
Product of excess acetic anhydride and H2O

Unreacted aniline (amber color)

Activated charcoal adsorbs

impurities

RECRYSTALLIZATION IN THE
PURIFICATION OF ACETANILIDE
Crude Acetanilide
acetanilide +
impurities

heat
+ activated
charcoal
hot filtration

Residue

Filtrate

activated charcoal + insoluble

impurities

acetanilide + soluble
impurities
ice bath
filter

Filtrate

Residue

water-soluble
impurities

Pure acetanilide

QUANTITATIVE ANALYSIS

To synthesize acetanilide, 3.0 ml of

acetic anhydride was gradually added
to 2.0 ml of aniline in 20.0 ml of water.
The reaction produced 2.60 grams of
crude acetanilide which was purified
by recrystallization and produced 2.58
grams of pure acetanilide crystals.
Compute the % yield and % recovery.

Paracetamol, an analgesic drug, was synthesized

by the reaction of 1.50 milliliters of acetic
anhydride with 1.00 gram of 4-aminophenol.
After
synthesis,
1.10
grams
of
crude
paracetamol was collected as residue.
Recrystallization of the crude paracetamol
yielded 1.05 grams of pure crystals.
Molar mass: acetic anhydride: 102.10 g/mol
4-aminophenol: 109.13 g/mol paracetamol: 142.08 g/mol
Density: acetic anhydride: 1.02 g/ml

1. Illustrate the reaction. What is reaction mechanism in

the synthesis of paracetamol?
2. Which is the limiting reagent?
3. What is the percent yield?
4. What is the percent recovery after recrystallization?

END