Treatment of aromatic amines with gas mixtures derived from the

Details Treatment of aromatic amines with gas mixtures derived from the Treatment of aromatic amines with gas mixtures derived from the

1975-11-25

1977-04-26

Higel, Floyd D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260141, 260205, 260576, 423235, 423245, 423403, C01B 2126, C07C11300, C07C11500

Patent

active

040200523

ABSTRACT:
1,3-Diaryl triazenes, e.g., 1,3-diphenyltriazene, intermediates in the synthesis of aromatic diamines, e.g., p-phenylenediamine, are prepared by catalytically oxidizing ammonia, and subsequently the resulting nitric oxide, with a gas comprising diluted molecular oxygen, e.g., air, so as to produce a gas mixture containing dilute NO.sub.x, i.e., NO.sub.2 preferably admixed with NO, x being (1 + n), wherein n is the NO.sub.2 fraction of the NO.sub.x ; and contacting the gas mixture, preferably at a temperature in the range of about from 25.degree. to 350.degree. C., with excess primary aromatic monoamine, e.g., aniline, so as to result in a monoamine temperature in the range of about from 25.degree. to 90.degree. C., preferably 40.degree. to 60.degree. C., during contact. Highest yields of triazene are obtained when the x in NO.sub.x is about from 1.3 to 1.7, and the amount of NO.sub.x gas mixture contacted with the monoamine and the time of contact are such that at least about 60% by weight of the monoamine remains unconsumed. A gas mixture temperature just prior to gas contact with the liquid monoamine in the range of about from 110.degree. to 275.degree. C. is more preferred under certain circumstances.

REFERENCES:
patent: 2133037 (1938-10-01), Moyer
patent: 2894942 (1959-07-01), Hydro et al.
Filippuichev et al, Chemical Abstracts, vol. 28, 3720, 7-8 (1934).
Sutcliffe et al, Chemical Abstracts, vol. 69, No. 87957p (1968).
Houben-Weyl, "Methoden der Organischen Chemie", vol. X/3, p. 712 (1965).
Remy, "Treatise on Inorganic Chemistry", vol. I, pp. 598 and 599 (1956).

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