GB810844A - Improved process for the production of cycloaliphatic 1.2-diamines and the resultingproducts - Google Patents

Abstract

Cycloaliphatic-1,2-diamines of the formula: <FORM:0810844/IV (b)/1> wherein R is a divalent hydrocarbon radical with at least 4 carbon atoms and with 4-6 carbon atoms forming the direct link between the two valencies, which radical, together with the grouping <FORM:0810844/IV (b)/2> forms a cycloalkylene or bicycloalkylene radical, are made by heating a halogen ketone of the formula: <FORM:0810844/IV (b)/3> in presence of a hydrogen halide binding agent with urea, hydrogenating the imidazolone obtained of one of the following formul : <FORM:0810844/IV (b)/4> <FORM:0810844/IV (b)/5> to form an imidazolidone: <FORM:0810844/IV (b)/6> and hydrolysing this, advantageously in a mineral acid medium, to form the diamine. excess urea may be used in the first step as acid-binding agent. For the hydrogenation, nickel or platinum catalysts may be employed, and alcohols as solvents. The third hydrolysis stage may be effected with mineral acid, e.g. sulphuric or phosphoric acid. In examples, 2 - chloro - cyclohexanone, 2 - chloro - cycloheptanone, and chloro-2-decalone (produced by chlorinating 2-decalone) are each reacted with excess urea in diethyleneglycol diethyl ether, followed by hydrogenation, using Raney nickel, of the imidazolone to the imidazolidone, and hydrolysis of this with sulphuric acid to give 1,2 - diamino - cyclohexane, 1,2 - diamino - cycloheptane, and 1,2 - diamino - decalin respectively. Other starting materials specified are 2 - bromo - cyclohexanone, 3 - chloro - 1 - methyl - cyclohexanone - (2), 4 - chloro - 1 - methyl - cyclohexanone - (3), 3 - chloro - 1 - methyl - cyclohexanone - (4), 2 - bromo - cycloheptanone, 2 - bromo - cyclooctanone, 1 - chloro - 2 - decalone, 3 - chloro - 2 - decalone.