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Aspirin
Aspirin
Synthesis
Purification
Characterization
Aspirin: some background
! Patented by Bayer in 1893
! One of the oldest drugs
! One of the most consumed drugs
(Production in the US is 10 million
Kg/year)
Aspirin: Biological activity
! Analgesic (painkiller)
! Antipyretic (fever reducer)
! Anti-inflammatory (inhibition of the synthesis of
prostaglandins)
HO O O
OH
R
OH
enol phenol
Organic background O
Carboxylic acids
R OH
O O O
H OH H. C OH OH
benzoic acid
Organic background
Esterification
O O
H+ R2
R1 OH + HO R2 R1 O
This is an equilibrium!
Organic background
Esterification mechanism
H+
O
OH OH2+
R1 OH HO R2 R1 OH R1 OH
O + O
carboxylic acid alcool R2 H R2
-H+
R2
R1 O
ester
Organic background
Acidity: a review
! Bronsted-Lowry acid Acid pKa
Substance that can donate a proton
water 14.0
! Lewis acid
Substance that accepts lone-pair electrons Acetic acid 4.75
OH O HO O O
O O O
OH OH
H2SO4
+ +
O heat OH
acetic anhydride salicylic acid acetyl salicylic acid (aspirin) acetic acid
Reaction mechanism
OH
H+
O OH
O H+
O O
O O
HO O O
HO
-H+
O
O O O
+
HO OH
Safety
! Consult MSDS for safety information on all the chemicals
you plan to use.
! Induce crystallization.
! Write down the reaction with the correct stoechiometry. Ex: A+B " C
! Prepare a chart like below and calculate yield.
HO O O HO O O
OH O- Na+
+ NaOH + H2O
Assessment of purity:
Phenol test and visible spectroscopy
! Phenol react with FeCl3 (aq) to give a deep purple complex.
! Phenol is not present in the product but in one of the reactant.
! This test indicate the presence of unreacted starting material
(quantitative analysis possible via visible spectroscopy).
OH O
OH
salicylic acid