Sulfuric Acid → p-Toluenesulfonic acid

HRID 1706340Notes

Reaction equation

HRID 1706340 reaction equation
Cl[C:2]1[CH:7]=[C:6]([S:8]([OH:11])(=[O:10])=[O:9])[C:5](N)=[CH:4][C:3]=1[CH3:13].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[C:3]1([CH3:13])[CH:4]=[CH:5][C:6]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:7][CH:2]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 69362-Amino-5-chloro-4-methylbenzenesulfonic acid

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a typical process for preparing an aqueous solution of an alkali metal salt of 2-chloro-5-amino-4-toluene sulfonic acid, toluene is first reacted with sulfuric acid to produce para-toluene sulfonic acid as the principal product. The sulfonic acid is then reacted with chlorine to produce 2-chloro-para-toluene sulfonic acid as a principal product which is reacted with a mixture of 50 percent nitric acid and 50 percent sulfuric acid to produce 2-chloro-5-nitro-para-toluene sulfonic acid. The nitrated product is then neutralized in an aqueous lime slurry which is subsequently filtered. The aqueous nitrated product is then iron reduced to form an amine and the reaction mixture is neutralized with sodium hydroxide to a pH of about 9.5-10.5 and the resulting solution is subsequently filtered.

Sources & evidence

ORD record
ord-fb9d6b25942448fba249472afb1b050c
Source dataset
uspto-grants-1980_06
Patent number
US04207254

Reaction notes

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