Sulfuric Acid → 4-Nitro-m-phenylenediamine sulfate

HRID 1275426Notes

Reaction equation

HRID 1275426 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 to a pH of 2.0.±0.5. After the acid addition, the mixture is heated to between 70-75 deg. C for 3 hours. After 3 hours, the batch is cooled down to below 30 deg. C. and then agitated for another hour. The product is filtered, washed with water, and dried under conditions below 80 deg. 77-80 g. of 4-nitro-m-phenylenediamine sulfate is obtained resulting in a yellow-brown powder. A 94-97% 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
  3. additionAfter the acid addition
  4. temperaturethe mixture is heated to between 70-75 deg. C for 3 hours
  5. temperaturethe batch is cooled down to below 30 deg. C
  6. filtrationThe product is filtered
  7. washwashed with water
  8. customdried under conditions below 80 deg

Sources & evidence

ORD record
ord-eeac72fa504b4005a877beba76a5a64d
Source dataset
uspto-grants-2000_12
Patent number
US06160179

Reaction notes

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