Ethanol → Benzenamine, 3,3'-methylenebis-

Participants

Reaction Steps

30.7 g (0.1 mol) of 3,3'-dinitro-4-chlorobenzophenone, 1.5 g of 5% Pd/C and 100 ml of ethanol were charged in a closed glass vessel equipped with a thermometer and a stirrer. While stirring the mixture at a temperature of 65° to 70° C., hydrogen was introduced thereto and 20.1 l (0.9 mol) of hydrogen was absorbed in 6 hours. Since no more absorption of hydrogen was observed, the reaction was terminated at this point. The reaction mixture was cooled to room temperature and filtered to obtain a black filter cake. This filter cake was dissolved in 100 ml of a 90% aqueous isopropyl alcohol solution with heating. The catalyst was removed by filtration with heating. The filtrate was cooled to precipitate 3,3'-diaminodiphenylmethane hydrochloride as a crystal. This crystal was recovered by filtration, washed with 10 ml of isopropanol and neutralized with dilute aqueous ammonia to precipitate a white crystal. The crystal was recovered by filtration and dried in vacuo to give 16.3 g (yield 82.2%) of 3,3'-diaminodiphenylmethane.

Provenance & Evidence