Method for preparing azines

Abstract

A method is disclosed for preparing symmetrical azines of the formulas ##EQU1## and unsymmetrical azines of the formulas ##EQU2## and mixtures of azines (I), (II) and (IV) and (I), (III) and (V), wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is a hydrogen atom, a straight chain alkyl radical of from 1 to 12 carbon atoms, a branched chain alkyl radical or unsubstituted or alkyl substituted cycloalkyl radical of from 3 to 12 carbon atoms, a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene ring; further provided that R.sup.1 and R.sup.2 can be the same or different radicals, R.sup.3 is a radical different from R.sup.1 and R.sup.2 and R.sup.3 and R.sup.4 are radicals different from each other and each is different from R.sup.1 and R.sup.2 ; or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 or R.sup.3 and R.sup.4 bonded to the same carbon atom together form an unsubstituted or alkyl substituted alkylene radical of from 3 to 11 carbon atoms, each of the aforesaid radicals being unsubstituted or substituted with one or more radicals which are stable in the medium in which said azines are produced. The method involves reacting in the liquid phase and in the absence of a nitrile, a carbonyl compound of the formula ##EQU3## alone or together with a different carbonyl compound ##EQU4## or ##EQU5## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each has the same meaning defined above, with ammonia and hydrogen peroxide in the presence of an effective amount of at least one catalyst selected from the group consisting of the hydroxides and water soluble organic and inorganic salts of ammonium and the metals of Groups 1a and IIa of the Periodic Table of the Elements, and recovering the azine or mixture of azines from the reaction medium.