﻿Ethylene-sodium and of its Homologues. 179 



1*25 grm. sodium was dissolved in alcohol, and the product 

 dried at 196° C, 3 cubic centims. of iodide of ethyle added to it 

 and sealed up with it. The whole was then heated to from 120° C. 

 to 150° C. for about two hours. On opening the tube there 

 was a slight escape of gas. Water was then added to the pro- 

 duct, whereupon about 2 cubic centims. of light oil separated. 

 This oil proved to be common ether, boiling at 36° C, and 

 boiling to dryness at 40° C. The aqueous liquid was distilled, 

 and the distillate redistilled. To the second distillate a little 

 dry carbonate of potash was added, whereupon there formed two 

 layers, viz. an aqueous layer of carbonate and an oil. This oil 

 had the smell of the secondary alcohols, and was, I suppose, 

 secoudary butylic alcohol*. 



With the ethers of the fatty acids there is produced alcohol 

 and a salt of ethylene-sodium, e. g. 



C 2 H 4 Na\ n ^ C 2 H 5 1 n _ C 2 H 4 Na\ n C 2 H 5 \ n 

 H J U+ C 2 H 3 OJ U ~ C 2 H 3 J U II J U - 



A reaction of this kind has been observed with acetate of 

 ethyle, acetate of amyle, valerianate of ethyle, and benzoate of 

 ethyle. An analogous reaction has also been observed between 

 the hydrated oxide of amylene-sodium and valerianate of amyle. 

 There is every reason to believe that this reaction is perfectly 

 general, applicable to the hydrated oxides of all the olefine com- 

 pounds of sodium or potassium, and all the fatty and aromatic 

 ethers. 



Acetate of Ethylene-sodium. 



As just mentioned, this salt is produced by the action of 

 acetic ether on the hydrated oxide of ethylene-sodium. The re- 

 action appears to take place slowly even at 100° C.t At higher 



* Should further experiment confirm the indication here given, a very 

 important step in organic synthesis will have been taken — from ethylic to 

 isobutylic alcohol ', and in like manner a regular ascent of the series should 

 be practicable. 



t Owing to the occurrence of this reaction at 100° C, the attempts 

 made by various chemists to render acetic ether free from any alcohol with 

 which it might be contaminated by distilling it off sodium, ha\e had the 

 reverse result, and, continually producing alcohol, have rendered the ether 

 more impure. By the action of sodium on acetic ether there is produced 

 sodium-triacetyle and hydrated oxide of ethylene-sodium, which latter at- 

 tacks excess of acetic ether slowly at water-bath temperatures. A sample 

 of acetic ether which, from the mode of its preparation, must have been 

 originally almost, if not quite, free from alcohol, became, after several dis- 

 tillations off a small quantity of metallic sodium, charged with alcohol to 

 the extent of 15 per cent. This circumstance, which really no one can be 

 blamed for not expecting and providing against, has probably led Geuther, 

 Frankland, and Duppa astrav. 



N2 



