384 [Jan. 8, 



The brown distillate contains a large proportion of aniline which 

 has escaped decomposition, and which may be readily separated by 

 treatment of the distillate with an acid. On rectifying the portion of 

 the oil which is insoluble in acid, the thermometer becomes stationary 

 at 80, when a colourless transparent liquid distils, possessing all the 

 properties of benzol ; it was identified, moreover, by transformation 

 into nitrobenzol and aniline. The thermometer then rapidly rises, 

 becoming stationary again at between 190 and 195; a limpid oil 

 lighter than water passes over, which by its odour is at once recog- 

 nized as benzonitrile*. To remove every doubt, this oil was boiled 

 with an alcoholic solution of potash, when torrents of ammonia were 

 evolved, benzoate of potassium remaining as a residue. The benzoic 

 acid was separated from the salt by addition of hydrochloric acid, 

 and converted into the silver- salt, which was identified by analysis. 



The formation, under these circumstances, of benzonitrile is pro- 

 bably due to a reaction at a higher temperature between aniline and 

 the hydrocyanic acid generated during the destruction of another 

 portion of this substance, 



C 6 H 7 N+HCN=C 7 H 5 N+H 3 N. 



The action of heat upon aniline gives rise, in addition, to the forma- 

 tion of small quantities of a crystalline indifferent substance, and an 

 oily base boiling at a very high temperature ; the nature of both 

 these substances I have not yet determined. 



The transformation of aniline into benzonitrile is thus seen to be 

 far from elegant ; and if it have any claims to notice, it is merely 

 because there are at present comparatively few reactions known which 

 permit a passage from a hydrocarbon, CwH 2 w 6, to an acid, 



Cw+lH 2 w 6O 2 . 



This transformation may possibly be used for the production of 

 several of the higher terms of the series of aromatic acids which have 

 not yet been obtained. 



* I have lately had an opportunity of observing that benzonitrile solidifies in a 

 mixture of solid carbonic acid k and ether. The beautifully crystalline mass fuses 

 again at 17. 



