228 Messrs. Frankland and Buppa on the Action [Feb. 24, 



II. "On the successive Action of Sodium and Iodide of Ethyl 

 upon Acetic Ether." By E. Frankland, F.R.S., and B. F. 

 Duppa, Esq., F.R.S. Received January 13, 1870. 



In a paper by Mr. J. Alfred Wanklyn, bearing the above title, and pub- 

 lished in the Proceedings of the Royal Society, vol. xviii. p. 91, the 

 author refers to our memoir on the same subject printed in the Philo- 

 sophical Transactions for 18G6, vol. clvi. p. 37, and expresses his opinion 

 that our interpretation of the nature of the reaction must be erroneous 

 because it involves the disengagement of hydrogen. This opinion is founded 

 upon certain experiments which Mr. Wanklyn has himself made, and which 

 are described in the number of Liebig's * Annalen' for January 1869, and 

 in the Chemical Society's Journal, vol. ii. p. 371. 



In reference to this opinion we have to remark, first, that it is founded 

 upon experiments which differ essentially from our own ; and, second, that 

 even the results obtained in those experiments by the author do not warrant 

 the conclusion, at variance with ours, which he has drawn from them, 

 viz. that the evolution of hydrogen in this reaction is inadmissible. 



The reaction, the theoretical explanation of which Mr. Wanklyn seeks to 

 controvert, is described in the Philosophical Transactions, vol. clvi. p. 38, 

 as follows : — " When acetic ether is placed in contact with sodium it be- 

 comes hot, and a considerable quantity of gas is evolved, which, after being 

 passed first through alcohol and then through water, burns with a non- 

 luminous flame, and the products of combustion do not produce the slightest 

 turbidity on agitation with baryta- water. In fact the gas is pure hydrogen. 

 When the action is complete, the liquid solidifies on cooling to a mass 

 resembling yellow beeswax. By putting the sodium into the acetic ether 

 as just described, it is difficult to conduct the operation to completion, 

 owing to the liquid gradually assuming such a thick and pasty condition as 

 to prevent the further action of the sodium." Owing to the difficulty of 

 carrying the reaction far enough in this way we frequently employed a 

 modification of this process, which is minutely described in the same 

 memoir. The modification consisted in placing the sodium in a separate 

 vessel and causing the acetic ether to distil continuously over it ; thus 

 the portions of acetic ether still unacted upon were brought, again and 

 again, into contact with the sodium, whilst the non-volatile product of the 

 operation was retained in a lower vessel. As we acted upon several pounds 

 of acetic ether at once, the operation frequently lasted several days, and 

 during the whole time torrents of hydrogen were evolved. The tempera- 

 ture of the liquid in the distillation vessel was allowed to rise to 130° C, 

 and the amount of sodium consumed was not much less than one atom for 

 each molecule of acetic ether employed. 



We have made several attempts to determine quantitatively the volume 

 of hydrogen given off from a known weight of sodium, and also from a 

 know r n weight of acetic ether, but in neither operation could we obtain a 



