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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
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
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]
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
can be produced in a one step chemical process by reacting salicylic acid with acetyl anhydride.
The
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.
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
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.
Apparatus:
Beaker Dropper Stirring Pasteur
pipette
Thermometer Filter
rod
paper
Hot
plate
glass tube
Funnel
Test
Watch
tube cylinder
Capillary
Graduated
Start
Note: the acetic anhydride serves to wash the reactants to the bottom of the tube.
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.
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
Filter the crystals between the sheet of filter paper and squeeze the crystals between the filter to absorb excess water.
End