478 Royal Society .— 



The mixture of iodides, when submitted to the action of potassa > 

 yields ammonia, ethylamine, diethylamine, and triethylaminc, the 

 hydrate of tetrethylammonium, which is liberated, splitting into 

 ethylene, triethylamine, and water. The separation of the three 

 ethyle-ammonias presents unusual difficulties. The differences between 

 their boiling-points being rather considerable, 



Ethylamine, boiling-point 18° 



Diethylamine, „ „ 57 0, 5 



Triethylamine, „ „ 91° 



it was thought that they might be readily separated by distillation. 

 Experiments made with very large cmantities showed, however, that 

 even after ten fractional distillations the bases were far from being 

 pure. 



After many unsuccessful attempts, I have found a simple and 

 elegant process by which the three ethyle-bases may be easily and 

 perfectly separated. This process consists in submitting the an- 

 hydrous mixture of the three bases to the action of anhydrous oxalate 

 of ethyle. By this treatment, ethylamine is converted into diethyl- 

 oxamide, a beautifully crystalline body very difficultly soluble in 

 water, diethylamine into ethyhoxamate of ethyle, a liquid boiling at a 

 very high temperature, whilst triethylamine is not affected by oxalic 

 ether 



By the action of oxalic ether upon ethylamine, two substances may 

 be formed, viz. ethyl-oxamate of ethyle and diethyl-oxamide. 



Oxalic Ether. Ethylamine. Ethyl-oxamate of ethyle. Alcohol. 



(c c :^}«^l rc t}T ((§ ?}^ +2 [ c 'H'}o]. 



Oxalic Ether. Ethylamine. Diethyl-oxamide. Alcohol. 



In practice it appears that the second of these compounds only is 

 produced. 



In the action of oxalate of ethyle upon diethylamine, two similar 

 phases may be distinguished capable of producing respectively 



Diethyl-oxamate of ethyle .... ^° 2 °^" ^ H £ *J ] 0, and 



(c 2 o 2 n 



Tetrethyl-oxamide (C 2 H 5 )„ >N„. 



(C a H a )J 



In practice the frst of these two compounds only is generated. 

 The action of oxalate of ethyle upon triethylamine might have in- 

 volved the formation of the secondary oxalate of tetrethylammonium, 



