Sulfuric Acid → 4-Nitro-m-phenylenediamine sulfate

HRID 1275427Notes

Reaction equation

HRID 1275427 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[NH2:11])([O-:3])=[O:2].[S:12](=[O:16])(=[O:15])([OH:14])[OH:13]>C(O)(C)C>[S:12]([OH:16])([OH:15])(=[O:14])=[O:13].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[NH2:11])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 212084-Nitro-1,3-benzenediamine

Product 1

HCID 218892084-Nitro-m-phenylenediamine sulfate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In an agitated glass-reaction vessel, 50 g. of 4-nitro-m-phenylenediamine is added to 200 g. of isopropanol. While maintaining the temperature below 50 deg. C, 110.0 g. of conc. sulfuric acid is added to the mixture. After the acid addition, the mixture is heated between 70-75 deg. C for 3 hours, to a pH of 2.0±0.5. After 3 hours, the batch is cooled down to below 30 deg. C and then agitated for another hour. The product is filtered and dried under conditions below 80 deg. C. 78-81 g. of 4-nitro-m-phenylenediamine sulfate is obtained resulting is a yellow-brown powder. A 95-98% theoretical yield is obtained relative to 4 nitro-m-phenylenediamine.

Workup

  1. customIn an agitated glass-reaction vessel, 50 g
  2. temperatureWhile maintaining the temperature below 50 deg. C, 110.0 g
  3. additionAfter the acid addition
  4. temperaturethe mixture is heated between 70-75 deg. C for 3 hours, to a pH of 2.0±0.5
  5. temperaturethe batch is cooled down to below 30 deg. C
  6. filtrationThe product is filtered
  7. customdried under conditions below 80 deg. C

Sources & evidence

ORD record
ord-eaa2092414e14b37aa835fab0bf42d6e
Source dataset
uspto-grants-2000_12
Patent number
US06160179

Reaction notes

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