1868.] Aromatic Monamines into Acids richer in Car-bon. 303 



necessary to state that the difficultly soluble amide, when submitted to the 

 protracted action of boiling soda, is ultimately entirely converted into the 

 new acid. 



Of the three substances mentioned, the acid is by far the most interest- 

 ing, forming as it does the starting-point of a new group of compouwds, the 

 number and variety of which can scarcely be inferior to that of benzoic 

 acid. It thus became desirable to prepare the acid on a larger scale. For 

 this purpose it was not necessary to employ the nitrile or the amide in a 

 state of perfect purity. The crude nitrile had simply to be boiled for some 

 time with alcoholic soda, care being taken to condense the vapours, so as not 

 to lose any nitrile by evaporation. When ammonia w^as no longer evolved the 

 alcohol was boiled off, and the alkaline liquid filtered after cooling, whereby 

 small quantities of naphthylamine were separated. The brown liquid, when 

 decomposed by hydrochloric acid, furnished an abundant curdy precipitate, 

 consisting of the new acid. It was washed with cold water and recrystal- 

 lized partly from boiling water (in which it is very sparingly soluble), partly 

 from hot alcohol (by which it is copiously dissolved). Thus purified, the 

 new acid presents itself in the form of white needles, which fuse at 160° C. 

 Fused and resolidified, the new compound is heavier than water. When 

 heated beyond its fusing-point the new acid sublimes. The boiling-point 

 is considerably above 300°. The acid is nearly inodorous and tasteless ; 

 when heated it feebly evolves the odour of naphthaline ; its vapour, like 

 that of benzoic acid, irritates the respiratory organs. The solutions of this 

 acid have a distinct action upon litmus-paper, and decompose with facility 

 (more especially on heating) the alkaline carbonates. 



In accordance with a principle of nomenclature which I proposed 

 some time ago, I will designate the new acid by the name menaphthoxylic 

 or naphthaline-carboxylic acid. In this case the amide receives the name 

 menaphthoxylamide, the nitrile that of menapJithenylnitrile. 



I may be permitted briefly to mention some of the observations which, 

 in studying the new compound, I have already been able to collect. 



It has been stated that the nitrile fixes water with facility. It could not 

 he doubtful that in like manner it would also combine with sulphuretted 

 hydrogen. Indeed, when dissolved in alcoholic sulphide of ammonium, 

 and exposed for some hours to a temperature of 100°, the nitrile absorbs 

 one molecule of hydrosulphuric acid, being converted into a beautifully 

 crystalline body, easily soluble in alcohol, which fuses at 126°, and has the 

 composition 



This substance is menaphthosulphyl amide, corresponding to thioben- 

 zamide, the sulphuretted derivative of benzonitrile discovered by M, 

 Cahours. 



I have examined menaphthoxylic acid somewhat in detail. Like benzoic 

 acid, to w^hich it has a strongly marked family resemblance, it is a mono- 

 basic acid. The silver-salt is a white, scarcely crystalline precipitate, 



2 E 2 



