TRIPHENYLMETHANE, (C6H6)3CH

This article appears in Volume V27, Page 288 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: TOO-TUM

TRIPHENYLMETHANE, (C6H6)3CH , a hydrocarbon, important as being the parent substance of several

series

SERIES (a Latin word from serere, to join)

of exceedingly valuable dyestuffs, e.g. rosanilines and malachite greens derived from aminotriphenylmethanes, and aurins and phthaleins de-rived from oxytriphenylmethanes. It is obtained by condensing benzal chloride with mercury

diphenyl

DIPHENYL (phenyl benzene), C6H5

(

Kekule

KEKULE,
FRIEDRICH
- FRIEDRICH, JOHANN (1836— )
AUGUST (1829-1896)

and Franchimont, Ber., 1872, 5, p. 9c7-); from benzal chloride or benzotrichloride and zinc dust or

aluminium

ALUMINIUM (symbol Al; atomic weight 27.0)

chloride; from chloroform or carbon tetrachloride and benzene in the presence of

aluminium

ALUMINIUM (symbol Al; atomic weight 27.0)

chloride; and deamidating di- and tri-aminotriphenylmethane
with nitrous acid and alcohol (0. and E. Fischer, 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 white crystalline solid, melting at 92 and boiling at 358. It separates from benzene and thiophene with one molecule of the " solvent of crystallization." On oxidation it gives triphenylcarbinol, (C6H5)3COH, and reduction with hydriodic acid and red phosphorus gives benzene and

toluene

TOLUENE, or METHYLBENZENE

. It combines with 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 salt of the carbinol formed on oxidizing this substance is the valuable dye rosaniline.
Considerable

interest

INTEREST

is attached to the remarkable

series

SERIES (a Latin word from serere, to join)

of 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, silver or mercury. Triphenylmethane chloride yields triphenylmethyl; ditolylphenylmethyl and tritolylmethyl have also been prepared. They behave as unsaturated compounds, combining with oxygen to form peroxides and with the halogens to form triarylmethane halides. Triphenylmethyl also combines with

ethers

ETHERS

and esters, but the compounds so formed are unsaturated. In the solid state triphenyl is colourless, crystal-line and bimolecular. It was thought that it might be identical with hexaphenylethane, but the supposed

synthesis

SYNTHESIS (Gr. a6vOeacs, from avvrcBivac, to put together)

of this sub-stance by Ullmann and Borsum (Ber., 1902, 35, p. 2897) appeared to disprove this, although it showed that triphenylmethyl readily isomerized into their product, under the influence of catalysts. A.E. Tschitschibabin (Ber., 1908, 41, p. 2421), however, has shown that Ullmann and Borsum's preparation was para-benzhydroltetraphenylmethane (C6H5)2CHC6H4C(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 solution, whilst ditolylphenyl and tritolylmethyls give orange solutions which on warming turn to a violet and to a magenta, the changes being reversed on cooling. Several views have been published to explain this fact. A 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

Cone

CONE (Gr. Kwvos)

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

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