Azobenzoilid — Hydrurets qfBenzoyline and Azobenzoylin. 431 



taken ns the equivalent of nitrogen, we obtain the formula 

 (C 14 H 10 N 2 + N) + (C 14 H 10 W + H 2 .) This body is iso- 

 meric with azobenzoid, which is insoluble in aether, uncry- 

 stalline, but crystallizes after fusion, which the above body 

 does not. 



Azobenzoilid. — Purified bitter almond oil was distilled, and 

 the first eighth of the product mixed with ammonia; in three 

 weeks half of the oil had become solid ; aether extracted the 

 oily portion, the remainder was crystalline. It is insoluble in 

 alcohol, very little soluble in aether, is decomposed by distil- 

 lation, forms with nitric acid an oily substance. Formula 



C 14 H 11 N*. It is therefore isomeric with azobenzoid and 

 azobenzoidine. 



Hydruret of benzoyline is formed by treating hydruret of 

 azobenzoylin with hydrochloric acid ; a thick oily matter j§ 

 produced, which must be washed with boiling water and dried 

 until it is solid. It is colourless, inodorous, easily soluble in 

 alcohol and aether, is not decomposed by distillation ; forms 

 a compound with bromine. By the addition of ammonia to 

 its boiling alcoholic solution, hydruret of azobenzoylin is 

 formed. Formula C 14 H 12 O 2 . It is therefore isomeric with 

 hydruret of benzoyl. 



Hydruret of Azobenzoylin. — It has been mentioned above, 

 that in the process for procuring azobenzoidin by the action 

 of ammonia on almond oil, an oily matter, azobenzoyl, and a 

 substance in acicular crystals are produced. This mixture is 

 heated with alcohol until it boils, and hydrochloric acid added; 

 the whole is dissolved, except a small quantity of a crystalline 

 substance. The alcoholic solution deposits an oily matter on 

 evaporation ; this, when treated with ammonia, becomes solid 

 in a few minutes. The solid part must be quickly washed 

 with a mixture of alcohol and aether, by which a white sub- 

 stance is obtained, which may be purified by repeated recry- 

 stallization out of alcohol. It is colourless, inodorous, tolera- 

 bly soluble in boiling alcohol; the solution deposits it on 

 cooling in the form of long needles. It may be distilled with- 

 out decomposition, but is easily decomposed by hydrochloric 



acid. Formula C 14 H 12 N*". It is therefore isomeric with 

 hydrobenzamid, benzhydramid, and benzoinanud. The hy- 

 drobenzamid is easily soluble in aether, and crystallizes in 

 octahedrons. Benzhydramid is not decomposed by hydro- 

 chloric acid, and benzoinamid is distinguished by its almost 

 perfect insolubility. 



Laurent has discovered benzoyl (Liebig's benzil) in the 

 purified oil of bitter almonds. By treating almond oil with 



2 G2 



