申请人:THE GOODYEAR TIRE & RUBBER COMPANY
公开号:EP0617004A1
公开(公告)日:1994-09-28
The present invention relates to a process for the preparation of a N-substituted-N'-phenyl-p-phenylenediamine of the formula:
comprising reacting (a) a mixture of (1) N-phenyl-p-quinoneimine of the formula:
and (2) p-hydroxydiphenylamine in a mole ratio of N-phenyl-p-quinoneimine to p-hydroxydiphenylamine of from 1.5:1 to 1:1.5 with (b) a primary amine of the formula:
R¹-NH₂
in the presence of methanol wherein R¹ is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula:
wherein R² may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R³ is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6.
本发明涉及一种制备式为 N-取代-N'-苯基-对苯二胺的工艺:
包括使(a)式中的(1)N-苯基-对醌亚胺的混合物与(2)式中的(3)N-苯基-对醌亚胺反应:
和(2)对羟基二苯胺(N-苯基对醌亚胺与对羟基二苯胺的摩尔比为 1.5:1 至 1:1.5)与(b)式中的伯胺的混合物反应:
R¹-NH₂
在甲醇存在下,其中 R¹ 选自由具有 1 至 20 个碳原子的烷基、具有 6 至 8 个碳原子的环烷基和结构式如下的基团组成的基团组:
其中 R² 可以相同或不同,且独立地选自氢和具有 1 个碳原子的烷基组成的基团组,R³ 选自具有 1 至 12 个碳原子的烷基组成的基团组,n 为 0 至 6 的整数。