





Decomposition of Aniline by Nitrous Acid. 373 



agine,* has however, pointed out the action of nitric acid contain- 

 ing nitrous acid, as a means of effecting this decomposition in 

 bodies which like that substance had hitherto resisted all agents ; 

 and he has shown moreover, that benzamid and butryamid are 

 easily decomposed with the liberation of their respective acids, 

 when a current of nitric oxyd gas is passed through their solutions 

 in nitric acid. 



Led by these considerations, I was desirous of submitting to 

 the action of nitrous acid, some of the organic alkaloids, and 

 I selected aniline as the one most convenient for the purpose ; 

 Hoifman has shown that the compound of ammonia and phenol 

 is slowly converted into this alkaloid with the elimination of 

 water, when exposed in sealed tubes to a high temperature, and 

 it was to be expected, if this plan of research proved successful, 

 that phenol might be regenerated. Accordingly, some pure ani- 

 line obtained by the distillation of indigo with hydrate of potassa 

 and carefully rectified, was dissolved in nitric acid ; the saturated 

 solution of the nitrate thus obtained, was mixed with half its 



volume of nitric acid, sp. gr. 1*25, and three or four volumes of 



water. The gas evolved by the action of heated nitric acid upon 

 mercury, was then passed through the cold liquid ; but no action 

 was perceived, and the orange-red fumes of nitrous acid passed 

 off into the air. The solution was then heated to about 170° F., 

 and again submitted to the action of the nitric oxyd ; immediate 

 absorption and a violent action ensued ; the whole liquid efferv- 

 esced from the escape of a colorless, inodorous gas, which had 

 the characters of nitrogen. The liquid, which before was trans- 

 parent, grew brownish and turbid, and soon an oily film appeared 

 on its surface. When the effervescence had ceased, and the odor 

 of nitrous acid announced that the reaction vvas complete, the 

 liquid was cooled and agitated with ether; the etherial solution 

 decanted, filtered and evaporated at a gentle heat, left an oily 

 liquid which was nearly equal in volume to the aniline employed. 

 It was brownish colored, and possessed in the highest degree 

 the peculiar odor of castoreum, with an acrid, caustic taste. It 

 was more dense than water, and soluble to a small extent in that 

 liquid, to which it imparted its own smoky flavor; a splinter of 

 pine wood, moistened with this solution and then dipped in nitric 

 a ctd, assumed on drying a characteristic blue color, changing to 

 a dark brown. The oil was readily soluble in a solution of caus- 

 tic potash, and was precipitated unchanged from this solution, 

 oy hydrochloric acid. Boiled with a solution of nitrate of silver, 

 the salt was reduced and metallic silver precipitated. The action 

 °f strong nitric acid was violent ; on boiling the mixture as long 

 as red fumes appeared, an acid was obtained which gave with 



Chim 



Second Series, VoL VIII, No. 24.— Nov., 1849. 4S 



