Reaction #324027

Reaction equation

2,4,4'-trinitroazobenzene

p-phenylenediamine

→

1,2,4-triaminobenzene

Yield 86.8%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherA 500 ml autoclave equipped with a stirrer and a gas-introducing tube
2. 2
   OtherThe inside of the reactor was purged completely with hydrogen
3. 3
   Temperaturewhile maintaining the pressure of hydrogen at 70 kg/cm2
4. 4
   FiltrationThe reaction mixture was filtered
5. 5
   WashThe cake was washed with water
6. 6
   workup.DISTILLATIONdistilled
7. 7
   Otherto afford 2.5 g of a fraction
8. 8
   OtherThe distillation residue was recrystallized from chloroform

Procedure

A 500 ml autoclave equipped with a stirrer and a gas-introducing tube was charged with 9.5 g of 2,4,4'-trinitroazobenzene, 0.6 g of PtO and 100 ml of ethanol. The inside of the reactor was purged completely with hydrogen, and the reaction was performed at 80° C. for 6 hours with stirring while maintaining the pressure of hydrogen at 70 kg/cm2.G. The reaction mixture was filtered. The cake was washed with water. The wash liquid and the filtrate were combined, and distilled to afford 2.5 g of a fraction having a boiling point of 174° to 180° C./30 mmHg.ab. This fraction coincided with p-phenylenediamine as a standard product. The distillation residue was recrystallized from chloroform to afford 3.2 g of 1,2,4-triaminobenzene having a melting point of 93° to 96° C. This product corresponded in IR spectrum with a standard product.

Source