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AssigneeUniroyal Chemical Company, Inc.
InventorsRussell Edward Malz, Gerard V. Smith, Mark Peter Ferrandino, Ruozhi Song, Chung-Yuan Lin, Franklin Herbert Barrows
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Processes of preparing para substituted phenylamines, such as, p-phenylenediamines, and particularly, p-aminodiphenylamine. One process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in specified proportions and within a specified temperature range, in the absence of oxygen, and in the presence of a homogeneous acid catalyst, such as hydrochloric acid. A second process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in the presence of a solid acid catalyst, such as acidic zeolite Y, under reaction conditions.
A process of preparing para substituted phenylamines comprising contacting phenylhydroxylamine, optionally substituted with at least one inert substituent, with a nucleophilic reagent, the molar ratio of nucleophilic reagent to phenylhydroxylamine ranging between about 2 and about 25, the contacting of the phenylhydroxylamine and nucleophilic reagent being conducted in the absence of oxygen and in the presence of a homogeneous acid catalyst at a temperature ranging from about 80.degree. C. to about 100.degree. C. such that a para substituted phenylamine, optionally correspondingly substituted with at least one inert substituent, is formed in a yield greater than about 15 weight percent.
A process of preparing p-aminodiphenylamine comprising contacting phenylhydroxylamine and aniline, the molar ratio of aniline to phenylhydroxylamine being between about 3 and about 20, the contacting being conducted in the absence of oxygen and in the presence of concentrated hydrochloric acid at a temperature in the range from about 80.degree. C. to about 100.degree. C. such that p-aminodiphenylamine is produced in a yield greater than about 50 weight percent.
Dependencies are inferred from the claim text.