256 Dr. Hofmann on the Mustard Oil of the Ethyl Series, [Feb. 13, 



I almost wonder now that the experiments performed in the phenyl 

 series, and soon afterwards also in the naphthyl series, were not even then 

 extended to the ethylic compounds and their homologues — the more so since 

 the study of the action of bisulphide of carbon upon amylamine and ethyl- 

 amine had, so to say, supplied me with the material for the inquiry. When 

 contemplated in the light of the recent observations, these experiments 

 acquired an increased interest ; for I could no longer doubt that the reaction, 

 which had yielded me the sulphocyanide of phenyl, when appropriately 

 applied to the derivatives of methylic, ethylic, and amylic alcohols, would 

 put me into possession of the compounds isomeric with the sulphocyanic 

 ethers which I was anxious to procure. Experiment has not failed to 

 confirm my anticipations. 



Experimerds in the Ethyl series. 



The general character of the action of bisulphide of carbon upon ethyl- 

 amine I had examined when more minutely investigating the behaviour of 

 amylamine under the influence of the bisulphide*. I have resumed the 

 inquiry, which has furnished me the following results : — 



On adding bisulphide of carbon to an alcoholic solution of ethylamine, 

 the liquid becomes more or less heated, according to the concentration of 

 the solution. The liquid turns neutral, and yields on evaporation an oily 

 compound, which after some time solidifies into a mass of splendid tabular 

 crystals. This compound fuses at 103°, and then retains the liquid con- 

 dition even when cooled to the ordinary temperature. When gently heated, 

 the salt is volatihzed, partly, at all events, without decomposition. These 

 crystals are the ethylamine-salt of ethyl- sulphocarbamic acid. 



, rc,H, 1 N 1 + c s - K^^>" HN] I g 



The salt is readily soluble both in water and in alcohol. Addition of soda 

 disengages ethylamine, giving rise to the formation of ethylsulphocarba- 

 mate of sodium. Hydrochloric acid decomposes the salt with separation 

 of the acid, which collects in oily drops on the surface of the liquid, gra- 

 dually solidifying to a mass of fatty crystals. Excess of hydrochloric acid 

 dissolves these crystals, bisulphide of carbon being evolved, and a salt of 

 ethylamine remaining behind. 



Under the protracted influence of heat ethylsulphocarbamate of ethyl- 

 amine is thoroughly decomposed. 



Even at the temperature of boiling water, torrents of sulphuretted hy- 

 drogen are disengaged ; the transformation is rapidly accomplished when 

 the alcoholic solution is heated under pressure to 110° or 120°. On eva- 

 porating the alcoholic liquid after the evolution of sulphuretted hydrogen 

 has ceased, an oily liquid remains behind, which also crystallizes after some 

 time. These crystals fuse at 77° ; they are likewise soluble in alcohol, 



*Proc. of the Roy. Soe. vol. ix. p. 591 (1860). 



