Diphenylamine aniline manufacture

Diphenylamine is manufactured by the self-condensation of aniline in the presence of a small amount of a mineral acid, such as anhydrous hydrogen chloride, or Lewis acids, such as ferrous chloride or ammonium bromide. 

The use of certain vanadium compounds as catalysts has been increasing. Vanadium oxy trichloride is a catalyst in making ediylene-propylene rubber. Ammonium metavanadate and vanadium pentoxide aie used as oxidation catalysts, particularly in the production of polyamides, such as nylon, in the manufacture of H>S04 by the contact process, in the production of phdialic and maleic anhydrides, and in numerous other oxidation reactions, such as alcohol to acetaldehyde, anthracene to anthraquinone, sugar to oxalic acid, and diphenylamine to carbazole. Vanadium compounds have been used for many years 111 die ceramics field for enamels and glazes. Colors are produced by various combinations of vanadium oxide and silica, zirconia, zinc, lead, tin, selenium, and cadmium. Vanadium intermediate compounds also are used in the making of aniline Mack used by the dye industry... 

Spandex stretch fiber, based on polyurethanes, was developed by DuPont and appeared in 1962. From this time, polyurethanes would account for the greater part of demand for anilines. Aniline production alone had more than doubled, to over 100 million lbs. per year, between 1939 and 1957, in part to satisfy demand in products other than dyes. Half the US output was consumed in the production of rubber additives, mainly diphenylamine and cyclohexylamine, the latter used as a chain stopper in manufacture of polyurethanes (also as a boiler water additive and, in the US until banned in 1970, in the manufacture of cyclamate sweeteners). Other polymers, such as epoxy resins, relied on the bulk availability of various aromatic amines (Chapter 14). 

Arylation involves the reaction between amines and phenols, aryl halides and aryl amines, including aniline. In arylation, one reactant acts as solvent acidic catalysts and high temperatures are employed. Diphenylamine (A-phenylbenzeneamine, /V-phenylani-line) (8) is made by condensation of aniline in the presence of a small amount of mineral acid catalyst at around 300 °C catalytic reaction of chlorobenzene with aniline at high temperature and pressure and continuous vapor-phase catalytic condensation of aniline. It is a useful intermediate in azo dye manufacture. Crompton is the main US manufacturer of 8, producing 1.3 billion lbs. in 2000. Applications include as lube additives... 

Over half of the remaining market for products used in the processing of rubber is made up of antioxidants, antiozonants and stabilizers, either amino compounds or phenols. Aniline is used to manufacture vulcanization accelerators, antioxidants and antidegradants. Of the latter, several are A-substituted derivatives of p-phenylenediamine and octyl dipheny-lamine. Diphenylamines terminate free-radical reactions by donating the amino hydrogen, and are used to protect a wide range of polymers and elastomers. Many synthetic rubbers incorporate alkylated diphenylamine antioxidants. Other antioxidants include aryl amine resinous products from, e.g. condensation of aniline and acetone in the presence of... 

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