Water → Sulfanilic acid

HRID 1073352Notes

Reaction equation

HRID 1073352 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:8](=O)(=[O:11])([OH:10])[OH:9].O.[OH-].[Na+]>ClC1C=CC=CC=1Cl>[S:8]([OH:11])(=[O:10])([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6115Aniline2×HCID 14798Sodium Hydroxide

Product 1

HCID 8479Sulfanilic acid

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
200 °C

Procedure

651.7 g (7.0 mol) of aniline in 1400 ml of o-dichlorobenzene were introduced into a 4 enamel stirring autoclave and 686.7 g (7.0 mol) of 100% sulphuric acid were added with stirring. The autoclave was then closed and the reaction mixture was heated to 200° C. with stirring. After 21/2 hours reaction time, the reaction mixture was cooled, poured into 1000 ml of water with stirring and neutralized with sodium hydroxide solution. Two liquid phases were obtained. After replenishing the aniline to the abovementioned value, the organic phase was added to a further batch. Pure p-sulphanilic acid was obtained from the aqueous phase by acidification using sulphuric acid. The yield amounted to 64.2%.

Workup

  1. additionwere added
  2. customThe autoclave was then closed
  3. stirringwith stirring
  4. customAfter 21/2 hours reaction time
  5. temperaturethe reaction mixture was cooled
  6. stirringwith stirring
  7. customTwo liquid phases were obtained
  8. additionthe organic phase was added to a further batch

Sources & evidence

ORD record
ord-79172fcae2834bb49f52cb5958aefd3e
Source dataset
uspto-grants-1990_11
Patent number
US04968835

Reaction notes

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