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ANILINE, PHENYLAMINE, or AMINOBENZENE, (C6H5NH2), an organic base first obtained from the destructive distillation of indigo in 1826 by O. Unverdorben (Pogg. Ann., 1826, 8, p. 397), who named it crystalline. In 1834, F. Runge (Pogg. Ann., 1834, 31, p. 65; 32, p. 331) isolated from coal-tar a substance which produced a beautiful blue colour on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the [v.02 p.0048] indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit nīla, dark-blue, and nīlā, the indigo plant. About the same time N.N. Zinin found that on reducing nitrobenzene, a base was formed which he named benzidam. A. W. von Hofmann investigated these variously prepared substances, and proved them to be identical, and thenceforth they took their place as one body, under the name aniline or phenylamine. Pure aniline is a basic substance of an oily consistence, colourless, melting at -8° and boiling at 184° C. On exposure to air it absorbs oxygen and resinifies, becoming deep brown in colour; it ignites readily, burning with a large smoky flame. It possesses a somewhat pleasant vinous odour and a burning aromatic taste; it is a highly acrid poison.

Aniline is a weak base and forms salts with the mineral acids. Aniline hydrochloride forms large colourless tables, which become greenish on exposure; it is the "aniline salt" of commerce. The sulphate forms beautiful white plates. Although aniline is but feebly basic, it precipitates zinc, aluminium and ferric salts, and on warming expels ammonia from its salts. Aniline combines directly with alkyl iodides to form secondary and tertiary amines; boiled with carbon disulphide it gives sulphocarbanilide (diphenyl thio-urea), CS(NHC6H5)2, which may be decomposed into phenyl mustard-oil, C6H5CNS, and triphenyl guanidine, C6H5N: C(NHC6H5)2. Sulphuric acid at 180° gives sulphanilic acid, NH2.C6H4.SO3H. Anilides, compounds in which the amino group is substituted by an acid radical, are prepared by heating aniline with certain acids; antifebrin or acetanilide is thus obtained from acetic acid and aniline. The oxidation of aniline has been carefully investigated. In alkaline solution azobenzene results, while arsenic acid produces the violet-colouring matter violaniline. Chromic acid converts it into quinone, while chlorates, in the presence of certain metallic salts (especially of vanadium), give aniline black. Hydrochloric acid and potassium chlorate give chloranil. Potassium permanganate in neutral solution oxidizes it to nitrobenzene, in alkaline solution to azobenzene, ammonia and oxalic acid, in acid solution to aniline black. Hypochlorous acid gives para-amino phenol and para-amino diphenylamine (E. Bamberger, Ber., 1898, 31, p. 1522).

The great commercial value of aniline is due to the readiness with which it yields, directly or indirectly, valuable dyestuffs. The discovery of mauve in 1858 by Sir W. H. Perkin was the first of a series of dyestuffs which are now to be numbered by hundreds. Reference should be made to the articles DYEING, FUCHSINE, SAFRANINE, INDULINES, for more details on this subject. In addition to dyestuffs, it is a starting-product for the manufacture of many drugs, such as antipyrine, antifebrin, &c. Aniline is manufactured by reducing nitrobenzene with iron and hydrochloric acid and steam-distilling the product. The purity of the product depends upon the quality of the benzene from which the nitrobenzene was prepared. In commerce three brands of aniline are distinguished—aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and para-toluidines; and aniline oil for safranine, which contains aniline and ortho-toluidine, and is obtained from the distillate (échappés) of the fuchsine fusion. Monomethyl and dimethyl aniline are colourless liquids prepared by heating aniline, aniline hydro-chloride and methyl alcohol in an autoclave at 220°. They are of great importance in the colour industry. Monomethyl aniline boils at 193-195°; dimethyl aniline at 192°.

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