Process for preparing 4-aminodiphenylamines

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

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C07C20900

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active

061405388

ABSTRACT:
A process for preparing an optionally substituted 4-aminodiphenylamine comprising reacting an optionally substituted aniline and an optionally substituted nitrobenzene in the presence of water and a base while controlling the water content so as to ensure a molar ratio of water to the base charged of not less than about 4:1 at the start of the coupling reaction and not less than about 0.6:1 at the end of the coupling reaction to produce 4-nitrodiphenylamine and/or 4-nitrosodiphenylamine and/or salts thereof. The coupling reaction is followed by a hydrogenation reaction where the coupling reaction product is hydrogenated in the presence of a hydrogenation catalyst and added water so as to ensure a molar ratio of total water to base of at least about 4:1 at the end of hydrogenation. Aqueous and organic phases are obtained and the optionally substituted 4-aminodiphenylamine recovered from the organic phase.

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patent: 5840982 (1998-11-01), Reynolds et al.
Catalytic Hydrogenation Reactions--The Effect of Water on Catalyst Activity, 2 pgs.
Research Disclosure, Process for N-Alkyl-N-Aryl-p-Phenylenediamines, Mar. 1998, No. 407,2 pgs.
J. Chem. Soc., Chem. Commun., Heterogeneous Catalytic Transfer Hydrogenation of 4-Nitrodiphenylamine to p-Phenylenediamines, 1988, pp. 1275-1276.

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