Adipic Acid → 1,2,4-Triaminobenzene

HRID 1391276Notes

Reaction equation

HRID 1391276 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.C(O)(=O)CCCCC(O)=O.[H][H]>[Ni].O>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:4]=1[NH2:1]

Participants

6

Reactant 3

HCID 196Adipic AcidHCID 73212,4-DinitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 692061,2,4-Triaminobenzene

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

91 Parts of finely ground 2,4-dinitro-aniline together with 73 parts of adipic acid, 10 parts of a commercial-type nickel catalyst and 400 parts by volume of water were charged into a hydrogenation autoclave. After the autoclave had been sealed, hydrogenation was effected in the usual manner at a temperature ranging from 60 to 100° C., while keeping the hydrogen pressure constant for about half an hour after the end of hydrogenation. For evidencing 1,2,4-triamino-benzene obtained, residual hydrogen was released, and the mixture was freed from the catalyst by filtration through a pressure filter under 20 atmsg. nitrogen and the filtrate passed into another flask flushed with nitrogen. The urea compound was prepared as described in Example 1. 62 Grams of a compound having a melting point higher than 335° C. were obtained. The following table shows accordance of the analytical data with the calculated values of the formula

Workup

  1. customAfter the autoclave had been sealed
  2. customranging from 60 to 100° C.
  3. customconstant for about half an hour

Sources & evidence

ORD record
ord-40e66a64eb1a41e5a367bacded43fe19
Source dataset
uspto-grants-1979_02
Patent number
US04141917

Reaction notes

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