Experiment # 8:

Preparation of Aspirin

Date: 14-12-10

Muhammad Usman

(2008-chem-02-B)
 Pyridine:

Harmful:
Pyridine is harmful if inhaled, swallowed or absorbed through the skin.

Highly flammable:
It has a flash point of 21 oC. It can readily catch fire. So care should be taken
while handling it. However, pyridine itself is weak carcinogen.

Properties of Pyridine:
IUPAC Name Pyridine
Azabenzene
Other names Azine
py
Appearance Colorless liquid

Structure

Molecular formula C5H5N

Molar mass 79.1g mol-1
Density 0.9819g ml-1
Melting point -41.6oC
Boiling point 115.2 oC
Solubility in water Miscible
Auto-ignition temperature 21 oC
Salicylic acid:

Harmful:
It is a Harmful compound & can cause hearing loss in Zinc deficient
individuals.

Properties of salicylic acid:

IUPAC name 2-hydroxy Benzoic acid

Other names Salicylic acid

Structure

Molecular formula C7H6O3

Molar mass 138.12 g/gmol

Colorless crystaline organic

Appearance
acid

Density 1.443 g/cm3

Melting point 159 oC
Boiling point 211 oC
Solubility in water 0.2 g/100 ml H2O (20 oC)
Acidity (Pka) 2.97
Flash point 157 oC
 Acetyl-chloride:

Harmful:
Eyes and skin is specially damaged with acetyl chloride. It can cause pain &
vomiting. It also reacts hazardously with ethanol and phosphorus tri-chloride.

Highly flammable:
It has a flash point of 13 oC. It can readily catch fire. So care should be taken
while handling it because its combustion products include Acetaldehyde which is
a strongly carcinogenic substance. However, ethanol itself is not cancer causing.

Corrosive:
Acetyl chloride is a corrosive compound. It burns eyes and causes blistering on
skin.

Properties of Acetyl chloride:

IUPAC Name Acetyl chloride
Ethanoyl chloride
Other names
Acyl chloride

Appearance Colorless liquid

 Structure

Molecular formula CH3-CO-Cl

Molar mass 78.49g mol-1
Density 1.104 g ml-1
Melting point -112 oC
Boiling point 52 oC
Solubility in water Reacts with water
Auto-ignition temperature 390 oC

Water:
It is a non-hazardous compound.

Environmentally safe:
Water is an essential part of life. Life cannot be sustained without water.
Food & eatables contain some amount of water in them. It is a non-
hazardous compound.

Water
IUPAC name
Oxidane
Hydrogen oxide
Dihydrogen monoxide
Hydrogen monoxide
Hydroxylic acid
Hydrogen hydroxide
Other names
R-718
Oxygen dihydride
Oxygen hydride
Oxane
 Structure

Molecular formula H2O

Molar mass 18.0152833 gmol-1

Appearance

1000 kg m-3 (liquid)

Density 917 kg m-3 (solid)

Melting point 0 oC
Boiling point 99.98 oC
Acidity (Pka) 15.74
Basicity (Pkb) 15.74
Viscosity 0.001 Pa.S (20 oC)
 Preparation of Aspirin

Chemicals required:
1) Acetyl Chloride 2) Dry Pyridine
3) Salicylic acid 4) Water

Chemical reaction:

Apparatus Required:
Volumetric flask Weigh Balance
Wire Gauze Tripod stand
Filter paper Beaker
Stirrer

Procedure:
1. Place 10 g Salicylic acid in conical flask & added 7 ml of Pyridine. Finally added 7.5 ml of
acetyl chloride at a rate of 1 ml per unit time with shaking continuously.
2. The reaction was exothermic in nature. The heat of reaction is responsible for the rise in
temperature of the mixture. Maintain the temperature of the mixture between 50-60 oC.
3. Then the solution was heated on water bath for 5-10 minutes & then cooled. This mixture was
poured in 300 ml of cold water.
4. Solution was filtered and aspirin was dried as product.
Precautions:
1. Take special care to avoid fumes evolved during heating or use fuming hood while
heating.
2. Solution should be stirred continuously during heating.
3. Water bath should be used for heating purpose.

Uses of Aspirin:

Aspirin’s uses lie in the category of Drugs. Its uses in the form of drug are as follows.

 Analgesic:
It is used to relieve minor aches and pains.
 Antipyretic:
It is used to reduce fever.
 Anti inflammatory:
Aspirin is also used as an anti-inflammatory drug.