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Fuchsine

FUCHSINE, or Magenta, a red dye-stuff consisting of a mixture of the hydrochlorides or acetates of pararosaniline and rosaniline. It was obtained in 1856 by J. Natanson (Ann., 1856, 98, p. 297) by the action of ethylene chloride on aniline, and by A.W. Hofmann in 1858 from aniline and carbon tetrachloride. It is prepared by oxidizing "aniline for red" (a mixture of aniline and ortho- and para-toluidine) with arsenic acid (H. Medlock, Dingler's Poly. Jour., 1860, 158, p. 146); by heating aniline for red with nitrobenzene, concentrated hydrochloric acid and iron (Coupier, Ber., 1873, 6, p. 423); or by condensing formaldehyde with aniline and ortho-toluidine and oxidizing the mixture. It forms small crystals, showing a brilliant green reflex, and is soluble in water and alcohol with formation of a deep red solution. It dyes silk, wool and leather direct, and cotton after mordanting with tannin and tartar emetic (see Dyeing). An aqueous solution of fuchsine is decolorized on the addition of sulphurous acid, the easily soluble fuchsine sulphurous acid being formed. This solution is frequently used as a test reagent for the detection of aldehydes, giving, in most cases, a red coloration on the addition of a small quantity of the aldehyde.

The constitution of the fuchsine bases (pararosaniline and rosaniline) was determined by E. and O. Fischer in 1878 (Ann., 1878, 194, p. 242); A.W. Hofmann having previously shown that oxidation of pure aniline alone or of pure toluidine yielded no fuchsine, whilst oxidation of a mixture of aniline and para-toluidine gave rise to the fine red dye-stuff para-fuchsine (pararosaniline hydrochloride)

CH3·C6H4NH2 + 2C6H5NH2 + 3O = HO·C(C6H4NH2)3 + 2H2O.
Colour base (pararosaniline).
HO·C(C6H4NH2)3·HCl = H2O + (H2N·C6H4)2C : C6H4 : NH2Cl.
Pararosaniline hydrochloride.

A. Rosenstiehl (Jahres., 1869, p. 693) found also that different rosanilines were obtained according to whether ortho- or para-toluidine was oxidized with aniline; and he gave the name rosaniline to the one obtained from aniline and ortho-toluidine, reserving the term pararosaniline for the other. E. and O. Fischer showed that these compounds were derivatives of triphenylmethane and tolyldiphenylmethane respectively. Pararosaniline was reduced to the corresponding leuco compound (paraleucaniline), from which by diazotization and boiling with alcohol, the parent hydrocarbon was obtained

(H2N·C5H4)2C : C6H4:NH2Cl → HC(C6H4NH2·HCl)3 → HC(C6H4N2Cl3) → HC(C6H5)3.
Pararosaniline hydrochloride. Paraleucaniline. Triphenylmethane.

The reverse series of operations was also carried out by the Fischers, triphenylmethane being nitrated, and the nitro compound then reduced to triaminotriphenylmethane or paraleucaniline, which on careful oxidation is converted into the dye-stuff. A similar series of reactions was carried out with rosaniline, which was shown to be the corresponding derivative of tolyldiphenylmethane.

The free pararosaniline, C19H19N3O, and rosaniline, C20H21N3O, may be obtained by precipitating solutions of their salts with a caustic alkali, colourless precipitates being obtained, which crystallize from hot water in the form of needles or plates. The position of the amino groups in pararosaniline was determined by the work of H. Caro and C. Graebe (Ber., 1878, II, p. 1348) and of E. and O. Fischer (Ber., 1880, 13, p. 2204) as follows: Nitrous acid converts pararosaniline into aurin, which when superheated with water yields para-dioxybenzophenone. As the hydroxyl groups in aurin correspond to the amino groups in pararosaniline, two of these in the latter compound must be in the para position. The third is also in the para position; for if benzaldehyde be condensed with aniline, condensation occurs in the para position, for the compound formed may be converted into para-dioxybenzophenone,

C6H5CHO → C6H5CH(C6H4NH2)2 → C6H5CH(C6H4OH)2 → CO(C6H4OH)2;

but if para-nitrobenzaldehyde be used in the above reaction and the resulting nitro compound NO2.C6H4.CH(C6H4NH2)2 be reduced, then pararosaniline is the final product, and consequently the third amino group occupies the para position. Many derivatives of pararosaniline and rosaniline are known, in which the hydrogen atoms of the amino groups are replaced by alkyl groups; this has the effect of producing a blue or violet shade, which becomes deeper as the number of groups increases (see Dyeing).

Note - this article incorporates content from Encyclopaedia Britannica, Eleventh Edition, (1910-1911)

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