1867.] 



Homologous to Hydrocyanic Acid. 



151 



In a researcli made by Mr. Buckton and myself on the transformations 

 of the amides and nitriles under the influence of sulphuric acid, we re- 

 peatedly had occasion to prepare acetonitrile (cyanide of methyl) and 

 propionitrile (cyanide of ethyl) by the distillation of a sulphomethyiate or 

 sulphethylate with cyanide of potassium. In our paper we mention sub- 

 stances of a formidable odour which appeared in these reactions, and we 

 describe the efforts we made in order to isolate them. But as they are only 

 formed in small quantity, we had to give up the attempt. 



Mr. E.Meyer*, who has also been occupied with cyanide of ethyl, but who 

 employed another method of preparation, encountered the same bodies. By 

 acting on cyanide of silver with iodide of ethyl in sealed tubes, he obtained, 

 together with iodide of silver, an unstable compound of cyanide of silver 

 and cyanide of ethyl ; and there was formed in the same reaction a liquid 

 of an overwhelming odour. This latter, on distillation, presented the cha- 

 racters of a mixture from which it was impossible to isolate a product with 

 a constant boiling-point. "When treated with an acid the odour disappeared, 

 and the solution contained ethylamine which was identified by the analysis 

 of the platinum-salt. These are certainly the characters of the cyanides 

 formed by the action of chloroform on the primary monamines ; and it can- 

 not be doubted that Mr. Meyer has had in his hands the ethyl-term of the 

 series of cyanides which I am studying, both in the combination with cya- 

 nide of silver and in the complex liquid which accompanied it. 



If such results did not particularly attract the attention of chemists, 

 it was owing to the fact that the author failed in ascertaining the comple- 

 mentary product of ethylamine, namelj^, formic acid. Mr^ Meyer, besides, 

 states that his research remained unfinished ; and thus it will be under- 

 stood how experiments otherwise so carefully carried out should have fallen 

 into an oblivion from which neither the author nor any other chemist has 

 endeavoured to recal them during the many years which have elapsed since 

 their publication. 



In consequence of the examination of the bodies produced by the action 

 of chloroform on the primary monamines, these old experiments have ac- 

 quired a new interest ; and it appeared to me, for more than one reason, 

 that it would be desirable to repeat them, making use of the experience 

 gained by m^y late researches. 



For this purpose I have submitted cyanide of silver to the action of 

 several organic iodides. 



The iodides of methyl and ethyl act very slowly on cyanide of silver at 

 the ordinary temperature ; but the reaction takes place at the temperature 

 of boiling water. 



After a digestion of about ten hours, the transformation is complete ; a 

 brown solid matter is formed, having the appearance of paracyanogen, to- 

 gether with a yellowish oily layer possessing in a marked manner the odour 

 of the isomers of the nitriles. 



Journal fiir praktische Ghemie, vol. Ixvii. p. 147. 



