Sulfuric Acid → 4-Amino-1,3-benzenedisulfonic acid

HRID 1073355

Reaction equation

[S:1](=[O:5])(=[O:4])([OH:3])O.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[NH2:6][C:7]1[C:12]([S:1]([OH:5])(=[O:4])=[O:3])=[CH:11][C:10]([S:1]([OH:3])(=[O:5])=[O:4])=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 6115Aniline

Product 1

HCID 673044-Amino-1,3-benzenedisulfonic acid

Conditions

Temperature: 200 °C

Procedure

225.5 g (2.3 mol) of 100% strength sulphuric acid were added to 257.0 g (2.76 mol) of aniline in 460 ml of ortho oil. The suspension obtained was heated at 200° C. for 2.5 hours in a 1.3 1 enamel autoclave. After cooling, the mixture was filtered off with suction and the filter residue was dried. The 475.6 g of solid contained 80.7% of p-sulphanilic acid in addition to unchanged anilinium hydrogensulphate, based on the excess sulphuric acid employed. Aniline-2,4-disulphonic acid was not formed.

Workup

customThe suspension obtained
temperatureAfter cooling
filtrationthe mixture was filtered off with suction
customthe filter residue was dried
additionin addition to unchanged anilinium hydrogensulphate

Sources & evidence

ORD record: ord-ca6a5238a0aa4cb68d5a645a169b8984
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04968835

Linked notes

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