450 MM. Lieben and Bauer on Chlorinated Ethers. 



the purpose, as it seemed likely that the action of the zinc com- 

 pound would extend only to the chlorine, and not to the oxygen 

 (as it might be presupposed to do in the case of the chlorine deri- 

 vatives of the alcohols, fatty acids, aldehydes, &c.) . 



It was desirable to start with the lowest ethers and the first 

 chlorine substitution-products. Unfortunately it was found that 

 the preparation of monochlorinated methylic ether was attended 

 with such difficulties that it was advisable to start with mono- 

 chlorinated ethylic ether*, and a lengthened and tedious investi- 

 gation of this body was necessary in order to clear up its con- 

 stitution. 



This investigation showed that the chlorine is very probably 

 unsymmetrically divided between the ether radicals contained in 



the ether; so that the formula ™ tt 5 > O must be assigned to 



it. Hence it will be necessary for the future to assign to this 

 body the name bichlorinated ether, while that of quadrichlorinated 

 ether must be given to the body G 4 H 6 CI 4 0, discovered by 

 Malaguti. 



In conjunction with Bauer t, Lieben had obtained a body 

 Q6 H 13 CI O by the action of zincethyle on chlorinated ether ; and 

 to this body, which might be called ethylochlorinated ether, the 



rational formula ^2115 f is to be assigned. 



When concentrated hydriodic acid acts upon this body, the 

 chlorine is mainly replaced by hydrogen, and along with hydro- 

 chloric acid, free iodine, and some secondary products there is 

 obtained a heavy oil containing iodide of ethyle, ethylated chlo- 

 ride of ethyle, and iodized iodide of ethyle. This latter has not 

 only the composition, but it has also the boiling-point of Wurtz's 

 iodide of butyle. It acts at ordinary temperatures on acetate of 

 silver, and yields an extremely odoriferous ether, the ethylated 

 acetate of ethyle, and, on the other hand, a gas which can be con- 

 densed to a liquid by a freezing-mixture, and which in all proba- 

 bility is butylene. Ethylated acetate of ethyle, treated with potash, 

 yields ethylated ethylic alcohol, similar in its properties to the 

 butylic alcohol which Wurtz obtained from the fusel-oil of beet- 

 root. Yet the new body is rather identical with the body called 

 hydrate of butylene, and is only isomeric with normal butylic 

 alcohol. 



In the previously cited investigation, Lieben and Bauer ob- 

 tained a body in which both atoms of chlorine in chlorinated 

 ether were replaced by ethyle, and which they called biethylic 



» Phil. Mag. S. 4. vol. xxiv. p. 305. f Ibid. 



