Preparation of n-phenylbenzoquinone-imine and converting same in

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

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564271, 564434, C07C24902

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051892189

ABSTRACT:
N-phenylbenzoquinone-imine is prepared by oxidizing N-(4-hydroxyphenyl)aniline in a liquid, at least partially organic reaction medium, in the presence of a basic compound and, advantageously, a catalytically effective amount of at least one manganese, copper, cobalt and/or nickel compound; this imine can be reacted with an aliphatic or cycloaliphatic amine to produce an N-phenyl-N'-cycloalkyl-para-phenylene-diamine and an N-phenyl-N'-cycloalkyl-2,5-cyclohexadiene-1,4-diimine, such 1,4-diimine itself being easily reduced to the corresponding p-phenylenediamine.

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patent: 3984402 (1976-10-01), Kalopissis et al.
patent: 4045170 (1977-08-01), Kalopissis et al.
patent: 4968843 (1990-11-01), Cottman
Denisov et al. Izv. Akad. Nauk. SSSR, Ser. Khim., (10) 2217-23 (1988) (Abstract).
Albright, "Sulfoxarium Salt as Reagents for the Oxidation of Primary & Secondary Alcohols to Carbonyl Compounds", J. Org. Chem., vol. 39, No. 13, 1974 pp. 1977-1979.
Research Disclosure 2244 No. 173 (1978/09) "Process of Preparing Polyaniline Amines" (Gautier).

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