aspirin preapation presentation

1. Chemical Process Industr ies
Topic: Preparation of Aspirin
Prepared By:

2. Details of aspirin:
o It is also commonly known by the name Acetyl Salicylic Acid and its IUPAC name
is: 2- Acetyloxybenzoic Acid
o Its molecular formula s: C9H8O4 and molecular weight is: 180.157 g/mol.
o Structural Formula of aspirin is :
o In 1853 Charles F. Gerhardt synthesized a primitive form of aspirin, derivative
of salicylic acid.
o In 1897 Felix Hoffmann working at Bayer, Germany derived a better way to
synthesize the aspirin.
o It was the first NSAID (non steroidal anti-inflammatory drug) and still is most
effective drug.
o It was mainly developed as an analgesic drug (pain killer).

3. Synthesis of aspirin:
o It is synthesised by the esterification reaction.
o The rectants used are salicylic acid and acetic anhydride.
o Here the salicylic acid is treated with acetic anhydride which results in chemical reation
turning the hydroxyl group of salicylic acid into ester group (R-OH -> R-OCOCH3).
o This yields aspirin and acetic acid, which is regarded as by product.
o Small amount of sulphuric acid (H2SO4) or phosphoric acid (H3PO4) are used as catalyst.
Chemical Reaction:
O
C-OH
OH
salicylic acid
O O
CH3C-O-CCH3
acetic anhydride
O
C-O-H
O C-CH3
O
aspirin
O
CH3C-OH
+
H

4. MECHANISM
••
••
••
••
O O
••
CH3C-O-CCH3
••
+
H
H

••
••
••
O O
••
••
CH3C-O-CCH3
H
••
••
••
••
O O
••
CH3C-O-CCH3
 ••
H
••
••
••
••
O O
••
CH3C-O-CCH3

H
••
••
••
••
O O
••
CH3C-O-CCH3
 ••
O
C-OH
•• C-OH
OH
••
O
H
••
••
••
••
CH3C-O-CCH3
OH
O O

••
••
••
O
C-OH
H
••

CH3C-O-CCH3
O
O O
H
••
••
••
••
••
••
O
C-OH
O
H

O
CCH3
••
••
••
O
C-OH
O
O
H
CCH3

••
••
••
••
O
C-OH
H
••

CH3C-O-CCH3
O
O O
H
••
••
••
••
••
••
••
O
••
HO-CCH3
••
••
O
C-O-H
O C-CH3
O

5. SYNTHETIC ASPIRIN
Synthesis from petroleum

6. FLOW CHART SCHEME FOR PURIFICATION
O O
CH3C-O-CCH3
O
C-OH
OH
H3PO4
heat 10 min add H2O cool
ppt
filter
O
C-O-H
O C-CH3
O
unreacted
salicylic acid
polymer
O
CH3C-OH
H3PO4
H2O
O
C-O–Na+
O C-CH3
NaHCO3 O
*
sodium
salicyate
polymer
NaHCO3 H2O
vacuum
filter *
polymer
O
C-O–Na+
O C-CH3
O
sodium
salicyate
NaHCO3 H2O
HCl
-CO2
O
C-O-H
O C-CH3
O
unreacted
salicylic acid
HCl NaCl H2O
O
C-O-H
O C-CH3
O
vacuum
filter
unreacted
salicylic acid
HCl NaCl H2O

7. Final Recrystallization of Crude Aspirin
O
C-O-H
O C-CH3
O
unreacted
salicylic acid
recytal.
ethyl
acetate
vacuum
filter
dry
O
C-O-H
O C-CH3
O
mp 135°C
unreacted
salicylic acid
ethyl
acetate

8. Industrial Scale Production of aspirin

9. Uses of aspirin:
o Over-the-counter pain relief, especially for headaches.
o Reduction of swelling and inflammation in arthritis and
injuries.
o Anti-coagulant given to sufferers of heart attack.
o Can reduce severity of heart attack if taken at first symptoms.
o Recovery after cardiovascular surgery.
o Treatment of rheumatoid arthritis, osteoarthritis and other
rheumatoid diseases

10. SIDE Effects:
o Risk of increase in gastrointestinal bleeding.
o It inhibits the ability of kidney to excrete uric acid and
exacerbate these conditions.
o Large dosages results in tinnitus (ringing in ears).
o May result in fatty liver and acute encephalopathy.
o May cause swelling of skin tissues.
o It increases the risk of cerebral microbleed.

11. Thank you