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V. " Notes of Researches on the Poly-Ammonias." No. V. 

 Action of Bichloride of Carbon on Aniline. By A. W. 

 HOFMANN, Ph.D., F.R.S. &c. Received June 17, 1858. 



In two former notes I have described the deportment of aniline as 

 the prototype of primary monamines with the bromine- and chlorine- 

 compounds of biatomic and triatomic radicals. It was found that 

 under the influence of these agents, two equivalents of aniline coalesce 

 to a more complex molecule, retaining the chemical character of the 

 constituents ; the action of bibromide of ethylene and chloroform 

 producing respectively 



Diethylene-diphenyl-diamine C M H 18 N 2 = ( & S 4 V'j N a . 



(C 2 H)'" 

 Formyl-diphenyl-diamine . . C 26 H 12 N 2 = 1 (C 12 H 5 ) 2 I N 2 . 



The result of these experiments led me to examine the behaviour 

 of aniline under the influence of organic chlorides containing even a 

 larger number of chlorine equivalents. The agent selected was the 

 body well known by the name of bichloride of carbon, t. e. tetra- 

 chlorinetted marsh-gas, or chloroform, in which the residuary 

 equivalent of hydrogen is replaced by chlorine. 



Aniline and bichloride of carbon do not act upon each other at the 

 common temperature ; at the temperature of boiling water a change 

 is perceptible, but even after several days' exposure the reaction is 

 far from being complete. On submitting, however, a mixture of 

 3^ parts by weight of aniline and 1 part of bichloride of carbon, 

 both in the anhydrous state, for about thirty hours to a temperature 

 of 1 70 C., the liquid will be found to be converted into a black 

 mass, either soft and viscid, or hard and brittle, according to time 

 and temperature. 



This black mass, which adheres firmly to the tubes in which the 

 reaction has been accomplished, is a mixture of several bodies. On 

 exhausting with water, a portion dissolves, while a more or less solid 

 resin remains behind. 



The aqueous solution yields, on addition of potassa, an oily preci- 

 pitate containing a considerable portion of unchanged aniline ; on 

 boiling this precipitate with dilute potassa in a retort, the aniline 

 distils over, whilst a viscid oil remains behind, which gradually 



