IOWA ACADEMY OF SCIENCES. 121 



and analyzed one of them which boiled at 280° and melted 

 at 97°, and which they supposed, from the results of their 

 analysis, to be diphenyl ketone, but this substance, accord- 

 ing to Watts' Dictionary of Chemistry, page 474, boils at 

 305°, and melts at 48°. It is safe to say, however, that 

 none of these higher boiling substances have yet been 

 identified. 



The degree of heat employed should be as low as possi- 

 ble in order to obtain a large yield of phenyl ether. 

 There is also obtained a relatively larger amount of tarry 

 residue. When a high degree of heat is employed the 

 aluminum phenolate decomposes mostly into phenol and 

 the higher boiling substances. There results, however, 

 much less of the tarry residue. By heating the tiask as 

 uniformly as possible at the close of the operation and 

 carrying the distillation as far as possible, a porous residue 

 remains, w^hich can quite readily be removed from the 

 flask when cool; otherwise a hard asphalt- like residue 

 remains, which it is impossible to remove without sacrific- 

 ing the flask. 



Gladstone and Tribe estimated from their results that 

 one-half of the aluminum phenolate decomposed, on heat- 

 ing, into aluminum oxide and phenyl ether, according to 

 the following equation: 



2A1 (OCc Hs )3 Alo 0, + 3C6 H5 — — Ce H5. 



While the reaction probably goes on according to this 

 equation it would seem from their results as well as my 

 own, that this is too high an estimate. From having care- 

 fully gone over the work a number of times it would seem 

 that about one-fourth of the aluminum phenolate is 

 decomposed into aluminum oxide and phenyl ether at a 

 low heat. While this method did not yield quite the 

 results hoped for on reading the article of Gladstone and 

 Tribe, it still proved to be a very good method, and is 

 mucli more easily and quickly carried out than the Hirsch- 

 Hoffmeister method, and the materials are cheap. From 

 1,227 grams of aluminum phenolate I obtained over 200 

 grams of pure phenyl ether boiling between 249° — 251°, 



I A S 



