Method for preparing azines

Details Method for preparing azines Method for preparing azines

1972-09-20

1976-05-25

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260566B, C07C11900

Patent

active

039592626

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 are 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 aliphatic 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 the azines are produced.
The method comprises reacting in the liquid phase, ammonia with a percarboxylic acid of the formula ##EQU3## wherein R.sup.5 represents a hydrogen atom, a straight chain alkyl radical of from 1 to 18 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 the aforesaid radicals can contain a non-epoxidizable or epoxidizable ethylenic double bond and/or one or more radicals which are stable in the medium in which the azines are produced, in the presence of a carbonyl compound of the formula ##EQU4## alone or together with a different carbonyl compound ##EQU5## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each have the same meaning defined above and recovering the azine or mixture of azines from the reaction medium.

REFERENCES:
patent: 2870206 (1959-01-01), Meyer et al.

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