BENZOIC ACID. 327 



Benzoyl chloride, C 6 IF.COC1. Is produced by the 

 action of phosphorus chloride on ben zoic acid ; and of 

 chlorine on oil of bitter almonds. Colorless oil, boil 

 ing at 199, of an exceedingly pungent odor. Is de 

 composed by water and by contact with moist air, 

 yielding benzoic and hydrochloric acids. Distilled 

 with bromides, iodides, or cyanides, it yields benzoyl 

 bromide, iodide, and cyanide, all of which are crystal 

 lizing compounds. Heated with an excess of phosphorus 

 pentachloride, it is converted into benzotrichloride, 

 C 6 H 5 .CC1 3 (p. 275). 



Benzamide, C 6 IF.CO.NH 2 . Is formed by continued 

 action of ammonia on ethyl benzoate or benzoic anhy 

 dride ; and by bringing benzoyl chloride together with 

 concentrated aqueous ammonia or dry ammonium 

 carbonate. Colorless, lustrous crystals ; fuses at 125; 

 and sublimes without decomposition. But slightly so 

 luble in cold water, easily soluble in hot water and in 

 alcohol. 



Benzhydroxamic acid, C IF.CO.NOH.H. Is ob 

 tained by the action of benzoyl chloride on an aqueous 

 solution of hydroxylamine hydrochlorate, which is 

 saturated with sodium carbonate. Colorless rhombic 

 crystals. Comparatively difficultly soluble in cold 

 water (44J parts at 6), much more readily in warm 

 water, very easily in alcohol. Has an acid reaction ; 

 fuses at 124-1 25, and decomposes at a higher tempera 

 ture suddenly and violently. By heating with dilute 

 hydrochloric or sulphuric acid, it is decomposed into 

 benzoic acid and hydroxylamine salt. Monobasic acid ; 

 yields crystallizing salts. 



Dibenzhydroxamic acid, (C 6 H 5 .CO) 2 Is T OH. Is 

 formed together with the preceding compound in the 

 described reaction. Lustrous, rhombic crystals. Al 

 most insoluble in water, difficultly soluble in cold alco 

 hol, more readily in hot, very slightly in ether. Has 

 an acid reaction, fuses at 145-146, and decomposes 



