Aspirin belongs to a group of organic compounds known as esters.

Aspirin

is an analgesic (painkiller), an antipyretic (fever reducer), and an anti-inflammatory agent. Bayer coined the name Aspirin for their new product to reflect its acetyl nature and its natural occurrence in the Spiraea plant.
Aspirin

alters the oxygenase activity of prostaglandin synthetase by moving the acetyl group to a terminal amine group of the enzyme.
It

interferes with the cyclooxygenase-1 and cyclooxygenase-2 enzymes

In aspirin synthesis, crystallization will take place.

Crystallization

is a process in which a dissolved solute comes out of solution and forms a crystalline solid.
is

the process of formation of solid crystals precipitating from a solution, melt or more rarely deposited directly from a gas. Crystallization involves the following steps: 1. Dissolving the substances with an appropriate solvent 2. Filtering the deposit crystal of the substances. 3. Washing the crystals to remove adhering mother liquor. 4. Drying the crystals to remove the last traces of solvent

5th century B.C.

The Greek physician Hippocrates described an extract of willow tree bark,a bitter powder that could be used to reduce fevers. Edward Stone (a clergyman) had collected observations from around the country on the effect of willow bark on the relief of fever due to agues (malaria). Salicin was isolated from willow bark and used as a pain reliever A Scottish physician found that extracts of willow bark relieved symptoms of acute rheumatism.

1763

1829

1830s

1870s

Professor von Nencki of Basle demonstrated that salicin was converted into salicylic acid in the body. [1][2]

[1] Figure

no. 1 Salicin

[2]

Figure no. 2 Salicylic acid

1897s

A German chemist named Felix Hoffman was working for the Bayer chemical company. His research led to the synthesis of acetylsalicylic acid (ASA) or aspirin.[3]

[3] Figure

no. 3 Aspirin

Figure no. 3 Aspirin synthesis

Aspirin

can be produced in a one step chemical process by reacting salicylic acid with acetyl anhydride.
The

synthesis of aspirin is classified as an esterification reaction.

Esterification

is simply the reaction between a carboxylic acid and an alcohol which is catalyzed by mineral acid.
esterification

is always accompanied by the formation of water , but, we will be using acetic anhydride, (CH3CO)2O, instead of acetic acid .
Acid

anhydride, which is made by the removal of a water molecule from two acetic acid molecules, reacts with alcohols in much the same way as acids to form the ester.

In

this image, a detailed reaction mechanism is given and to show how phosphoric acid catalyzes the formation of acetylsalicylic acid.

Physical State Color

Odor pH Vapor Pressure Melting Point
Autoignition Temperature

Powder White
Odorless 3.5(2.5g/L (20oC))

0.000003mmHg@25oC

136 140oC 500oC ( 932.00 oF) 250oC ( 482.00 oF) 3.3 g/l (20C) 1.350 C9H8O4 180.1610

Flash Point Solubility in water

Specific Gravity/ density

Molecular Formula Molecular Weight

Chemical Stability: Hygroscopic: absorbs moisture or water from the air. Conditions to Avoid: Incompatible materials, dust generation, exposure to moist air or water. Incompatibilities with Other Materials Strong oxidizing agents, strong acids, strong bases, alkalis. Hazardous Decomposition Products Carbon monoxide, carbon dioxide. Hazardous Polymerization will not occur.

[1] instead of sulfuric acid, we will use 85% phosphoric acid

Apparatus:
Beaker Dropper Stirring Pasteur

pipette

Thermometer Filter

rod

paper

Hot

plate
glass tube

Funnel
Test

Watch

tube cylinder

Capillary

Graduated

Start

Add 1.00 g of salicylic acid

Note: the acetic anhydride serves to wash the reactants to the bottom of the tube.

Add 2.0 mL of acetic anhydride

Add one small drop of 85% phosphoric acid

Mix the reactants thoroughly, the heat the reaction tube on a steam bath or in a beaker of 90 0C water for 5 minutes.

Slowly add 2.0 ml of water to the reaction mixture to decompose the excess acetic anhydride.

Note: Avoid breathing the vapors as they contain acetic acid.

Add an additional 1.0 ml of water.

Scratch the inside of the tube with glass stirring rod. Cool the tube in an ice bath.

no

Does crystallization of the product occur? yes Remove the solvent using Pasteur pipette

no

Add 1-2 ml of iced water

Filter the crystals between the sheet of filter paper and squeeze the crystals between the filter to absorb excess water.

Allow the product to air dry thoroughly

Determining the weight.

Calculate the percent yield

End