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salicylic acid
The problem with these chemicals was that they upset the user's stomach badly. Some people had
bleeding in their digestive tracts from the high doses of these chemicals needed to control, pain
and swelling. One of these people was a German named Hoffmann. Over 100 years ago, a
German industrial chemist, Felix Hoffmann set about to find a drug to ease his father's arthritis
without causing severe stomach irritation that was associated with sodium salicylate, the
standard anti-arthritis drug of the time. The large doses, 6 - 8 grams, of sodium salicylate that
was used to treat arthritis commonly irritated the stomach lining and many patients, including
Hoffmann's father could not tolerate the drug.
Figuring that the acidity made salicylates hard on the stomach, Hoffmann started looking for a
less acidic formulation. His search lead him to synthesize acetylsalicylic acid, a compound that
shared the therapeutic properties of other salicylates and might cause less stomach irritations. He
did this by putting the compound through a couple of chemical reactions that covered up one of
the acidic portions, leaving the carboxylic acid group, with an ACETYL group converting it into
acetylsalicylic acid.
acetylsalicylic acid
The new compound reduced fever, relieved moderate pain and at higher doses alleviated
rheumatic and arthritic conditions. Hoffman was confident that his new compound would be
more effective than the salicylates then in use.
His superiors did not share his enthusiasm. They doubted that acetylsalicylic acid would ever
become a valuable commercially successful drug because in large doses salicylates commonly
produced shortness of breath and an alarmingly rapid heart rate. It was taken for granted that
acetylsalicylic acid would weaken the heart and that physicians would be reluctant to prescribe
it.
In 1899, Dreser, a top chemist with Friedrich Bayer and Co., gave acetylsalicylic acid the now
familiar name aspirin, but in 1897 Bayer didn't think aspirin had much of a future. Little did
they know what the future held for aspirin.
Today, Americans consume an estimated 80 billion aspirins a year and the physicians desk
reference lists more than 50 over the counter drugs which contain aspirin as the principle active
ingredient.
The flask is then removed and allowed to cool. Ice cold distilled water is slowly added to the
flask to decompose any unreacted acetic annhydride.
Ice cold distilled water is added to the flask again. The flask is then chilled in an ice-water bath
for about 10 minutes until crystallization of the aspirin is complete. The aspirin crystals are
collected on a Buchner funnel and washed with additional ice cold distilled water. You are using
ice cold distilled water instead of room temperature distilled water because aspirin is insoluble in
cold water and you would not be dissolving any of your aspirin product. The acetic acid and
H2SO4 are water soluble, in any temperature water, and can be removed by washing the aspirin
with the chilled water. Salicylic acid is only slightly soluble in water and any unreacted salicylic
acid cannot be removed completely in the washing process. Once the aspirin crystals are purified
they are allowed to dry. They are then weighed and tested for purity.
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last updated: February 12, 2010