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TRIPHENYLMETHANE, (C6H6)3CH

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Originally appearing in Volume V27, Page 288 of the 1911 Encyclopedia Britannica.
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TRIPHENYLMETHANE, (See also:C6H6)3CH , a See also:hydrocarbon, important as being the See also:parent substance of several See also:series of exceedingly valuable dyestuffs, e.g. rosanilines and See also:malachite greens derived from aminotriphenylmethanes, and aurins and phthaleins de-rived from oxytriphenylmethanes. It is obtained by condensing benzal chloride with See also:mercury See also:diphenyl (See also:Kekule and Franchimont, Ber., 1872, 5, p. 9c7-); from benzal chloride or benzotrichloride and See also:zinc dust or See also:aluminium chloride; from See also:chloroform or See also:carbon tetrachloride and See also:benzene in the presence of aluminium chloride; and deamidating di- and tri-aminotriphenylmethane with nitrous See also:acid and See also:alcohol (0. and E. See also:Fischer, See also:Ann., 1881, 206, p. 152). The last reaction is most important, for it established the connexion between this hydrocarbon and the rosanilines. Triphenylmethane is a See also:white crystalline solid, melting at 92° and boiling at 358°. It separates from benzene and thiophene with one See also:molecule of the " solvent of See also:crystallization." On oxidation it gives triphenylcarbinol, (See also:C6H5)3C•OH, and reduction with hydriodic acid and red See also:phosphorus gives benzene and See also:toluene. It combines with See also:potassium to give (C6H5)3CK, which with carbon dioxide gives potassium triphenylacetate, (C6H5)3C CO2K. Fuming nitric acid gives a paratrinitro substitution derivative which on reduction gives paraleucaniline; the See also:salt of the carbinol formed on oxidizing this substance is the valuable dye rosaniline. Considerable See also:interest is attached to the remarkable series of See also:hydrocarbons obtained by Gomberg (Ber., 1900, 33, p. 3150, et seq.) by acting on triphenylmethane chloride (from triphenylmethane carbinol and phosphorus pentachloride, or from carbon tetra-chloride and benzene in the presence of aluminium chloride) and its homologues with zinc, See also:silver or mercury.

Triphenylmethane chloride yields triphenylmethyl; ditolylphenylmethyl and tritolylmethyl have also been prepared. They behave as unsaturated compounds, combining with See also:

oxygen to See also:form peroxides and with the See also:halogens to form triarylmethane halides. Triphenylmethyl also combines with See also:ethers and See also:esters, but the compounds so formed are unsaturated. In the solid See also:state triphenyl is colourless, crystal-See also:line and bimolecular. It was thought that it might be identical with hexaphenylethane, but the supposed See also:synthesis of this sub-stance by See also:Ullmann and Borsum (Ber., 1902, 35, p. 2897) appeared to disprove this, although it showed that triphenylmethyl readily isomerized into their product, under the See also:influence of catalysts. A.E. Tschitschibabin (Ber., 1908, 41, p. 2421), however, has shown that Ullmann and Borsum's preparation was See also:para-benzhydroltetraphenylmethane (C6H5)2CH•See also:C6H4•C(C6H5)3; and the view that solid triphenylmethyl is hexaphenylethane has much in its favour. Another remarkable fact is that these substances yield coloured solutions in organic solvents; triphenylmethyl gives a yellow See also:solution, whilst ditolylphenyl and tritolylmethyls give See also:orange solutions which on warming turn to a See also:violet and to a See also:magenta, the changes being reversed on cooling. Several views have been published to explain this fact. A See also:summary is given by Tschitschibabin (Journ. prak.

Chem., 1907 (ii.), 74, p. 340). It appears probable that the solutions contain a quinonoid modification (ssee Gomberg and See also:

Cone, Ann., 1909, 370, p. 142).

End of Article: TRIPHENYLMETHANE, (C6H6)3CH

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