67 



product being formed, which in its turn may be converted into the 

 third and even into the fourth compound. The following equations 

 represent perhaps more correctly the final result of the several 

 changes which are accomplished in the reaction of ammonia on 

 iodide of ethyl. 



H,N+ C 2 H 5 I=[(C 2 H 5 )H 3 N]I 



2H 3 N + 2C 2 H 5 I = [(C. 2 H 5 ) 2 H 2 N]I + [H 4 N]I 



3 H 3 N + 3 C 2 H 5 I = [(C ; H 5 ) ;) H N] 1 + 2 ([H 4 N] I). 



4 H 3 N+4 C 2 H 4 I = [(C; H B ) 4 N] 1 + 3 ([H 4 N] I). 



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

 yields ammonia, ethylamine, diethylamine, and triethylamine, the 

 hydrate of tetrethylammonium, which is liberated, splitting into 

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

 ethyl-ammonias presents unusual difficulties. The differences between 

 their boiling-points being rather considerable, 



Ethylamine, boiling-point .............. 18 



Diethylamine, .............. 57'5 



Triethylamine, .............. 91 



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

 Experiments made with very large quantities 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 ethyl-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 ethyl. By this treatment, ethylamine is converted into die thy I- 

 oxamide, a beautifully crystalline body very difficultly soluble in 

 water, diethylamine into ethyl-oxamate of ethyl, 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 ethyl and diethyl-oxamide. 



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



