1868.] Aromatic Monamines into Acids richer in Carbon, 301 



amine of the naphthyl series. This substance, presenting an exclusively 

 scientific interest but a few years ago, is now produced on an industrial 

 scale. It is more especially a beautifully crystallized yellow colouring- 

 matter (Manchestery ellow), the dinitronaphthylic acid, discovered and 

 first employed as a dye by Dr. Martins, which is largely manufactured 

 from naphthylamine. The base occurring in commerce is far from being 

 pure. It is generally met with as a brown fused mass, containing more 

 or less resinous matter and, more particularly, a considerable amount of 

 naphthaline. The purification of the commercial product presents some 

 difficulties ; still tolerable crystals may be obtained by crystallization 

 from petroleum. 



For the object 1 had in view it was unnecessary to purify the naphthyl- 

 amine of commerce. The base was mixed with powdered oxalic acid in 

 such proportions as to produce the primary oxalate with an excess of free 

 oxahc acid. Four parts of naphthylamine and five parts of crystallized oxalic 

 acid were found to yield very satisfactory results. The operation had to 

 be performed upon rather a large scale. After some trials, a cyanide-of- 

 potassium pot, provided with a cover and bent tube, proved to be the most 

 convenient apparatus for distilling the mixture. At the commencement of 

 the operation water and naphthaline were evolved ; soon, however, an oily 

 liquid appeared, solidifying on cooling, and consisting of a mixture of naph- 

 thylformamide, naphthy lax amide y oxalate of naphthylamine, naphthylamine, 

 and naphthaline. This distillate was transferred to one of the large two- 

 necked stone-ware bottles which are used for condensing nitric acid, mixed 

 with concentrated hydrochloric acid, and submitted to the action of a power- 

 ful current of steam, care being taken to condense the steam by a spiral sur- 

 rounded with water. Together with the water large quantities of a dark- 

 brown, almost opaque oil, heavier than water, were thus obtained. For 

 this oil, which a more minute examination proved to be the compound I 

 was endeavouring to prepare, I propose, in accordance with its composi- 

 tion, the name of cyanide of naphthyl. It still contained appreciable 

 quantities of naphthaline. In the main, however, the reaction had taken 

 place exactly in the same manner as in the case of aniline and toluidine, 

 the deportment of which I have described in my previous paper*. 



In the first place, the primary oxalate of naphthylamine had been con- 

 verted into naphtylformamide, 



^^'nf + ^''h I N = c,,h,^|n + H,0 -F CO,, 



which, losing one molecule of water, had in the second stage of the opera- 

 tion furnished cyanide of naphthyl, 

 CHOI 



C,,H, N = C,JI,CN +H,0. 

 H J 



* Log. cit p. 336-338. 



VOL. XVI, 2 E 



