3,3,5-Trimethylcyclohexanone → 3,3,5-Trimethylcyclohexanone

Participants

Reaction Steps

1-Aminocyclohexyl hydroperoxide (13.1 g), dihydroisophorone (14 g), methanol (25 cc.) and ammonium acetate (1.0 g) were mixed, store at 0°C overnight and worked up as in the previous example. Distillation gave cyclohexanone and dihydroisophorone (9.0 g), an intermediate fraction (3.2 g), b.p. below 100°C/0.7 mm,Hg., a fraction (8.1 g), b.p. 110°-114°/0.7 mm of 3,3,5'-trimethyl-1,1'-peroxy-dicyclohexylamine (peroxide equivalent, 234; perchloric acid equivalent, 245; and residue (1.5 g). The process may be carried out in the liquid or gas phase, but is preferably carried out in the gas phase as the liquid phase reaction tends to give a complex mixture of products of which only part are the desired derivatives of 1,12-dodecanedioic acid. The elevated temperature to which the 1,1'-peroxydicyclohexylamine is heated is suitably in the range 300°C to 600°C, and preferably from 400°C to 600°C. If the reaction is to be carried out in the gas phase it is preferred to use reduced pressures. Suitable pressures are of the order of 10 to 250 mm Hg.

Provenance & Evidence