Process for producing diphenylamines or N,N'-diphenylphenylenedi

Details Process for producing diphenylamines or N,N'-diphenylphenylenedi Process for producing diphenylamines or N,N'-diphenylphenylenedi

1988-09-14

1989-10-03

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564398, 564434, C07C 8506, C07C 8508, C07C 8758

Patent

active

048718750

ABSTRACT:
Diphenylamines or N,N'-diphenyl-phenylenediamines can be obtained by heat-reacting an aniline or a phenylenediamine with preferably an excess of a phenol in an amount of 4 to 20 moles per mole of the aniline or phenylenediamine in the presence of a hydrogen transfer catalyst and a cyclohexanone corresponding to said phenol.
The excess phenol used in the reaction undergoes reduction in the reaction system to form a cyclohexanone, which in turn reacts with the aniline or phenylenediamine to form a Schiff base and is thus consumed. The Schiff base forms the intended product by means of a dehydrogenation reaction, and the hydrogen evolved at this time reduces the phenol to form a cyclohexanone.
The phenol present in excess thus becomes in the system a solvent, a starting material for the cyclohexanone, and an acceptor of the hydrogen that forms as a by-product at the time of formation of the intended product. Hence, it becomes possible to obtain the intended product at a high selectivity from the anilines and phenylenediamines.
The process of this invention is an advantageous process for the industrial production of especially the nuclearly substituted diphenylamines.

REFERENCES:
patent: 3219704 (1965-11-01), Wilder et al.
patent: 3272865 (1966-09-01), Barker
patent: 3931298 (1976-01-01), Wollensak
patent: 4431841 (1984-02-01), Malz et al.
patent: 4480127 (1984-10-01), Becker et al.
patent: 4804783 (1989-02-01), Nagata et al.
Methoden der Organischen Chemie, vol. X1/1, pp. 112-122.

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