308 Scientific Proceedings, Royal Dublin Society. 



The substance melting at 214° C, which is sparingly soluble in most 

 solvents, is therefore tetranitrodiphenylethyleueether. When heated on the 

 water-bath with aqueous, or still better with alcoholic potash, it slowly 

 decomposed with formation of 24 dinitrophenol. 



(c) In Glacial Acetic Acid Solution. — 1, 2, 3, 4, and 6 molecular amounts 

 of nitric acid (Sp. g. 1-52) were added respectively to 5 flasks, each of which 

 contained 5 g. of diphenylethyleneether dissolved in 400 g. of glacial acetic 

 acid. The mixtures were aUowed to remain in the stoppered flasks for 10 

 weeks. From the solutions, which were colourless or faintly orange, the 

 diphenylethyleneether was in each case recovered unchanged. 



In another experiment 24 molecular amounts of nitric acid were added 

 to a flask containing 2-5 g. of the ether dissolved in 200 g. of glacial 

 acetic acid. The mixture became warm and the colour of the solution changed 

 through orange, green, purple, and violet, to brown in the course of a few 

 days. The deep-brown solution was examined after 9 weeks, and from 

 it, in addition to the parent ether, only a small quantity of a green oil 

 was obtained. 



(cZ) In Carbon 2' etr a chloride Solution. — Solutions of 5 g. of ethylenediphenyl- 

 ether in 200 g. of carbon tetrachloride to which 1, 2, 3, 4, and 6 molecular 

 amounts of nitric acid (Sp. g. 152) had been added rapidly turned dark-brown. 

 The colour then gradually became lighter, and finally, after about 3 weeks, it 

 was in all these cases light-orange. 



(1) The solution to which 1 molecular amount of nitric acid had been 

 added was filtered, after remaining at the temperature of the room for 

 18 weeks, from a small amount (015 g.) of a suspended solid, which proved 

 to be a mixture of tetranitrodiphenylethyleneether with oxalic acid and a 

 minute quantity of a lower melting (140-150° C.) fraction, which probably 

 contained 4- 10-dinitrodiphenylethyleneether. 



From the carbon teti'achloride filtrate 2-4-dinitrophenol was extracted 

 with alkali, and by evaporating the carbon tetrachloride we got about 4-3 g. 

 of iinchanged diphenylethyleneether. 



(2) From the solution to which 2 molecular amounts of nitric acid had 

 been added, 38 g. of the oi-iginal ether were recovered, together with small 

 amounts of oxalic acid. 



The tetranitro compound, which was probably also formed in the reaction, 

 was not isolated. 



(3) The solid suspended in the solution to which 3 molecular amounts 

 of nitric acid had been added, and which, like the last, had been allowed 

 to remain at the temperature of the room for 23 weeks, weighed 12 g., and 

 consisted of tetranitrodiphenylethyleneether, with some oxalic acid. From 

 the carbon tetrachloride filtrate 3 g. of the original ether and 08 of dinitro- 

 phenol were isolated. A small amount of a reddish oily substance obtained 

 probably contained 4-10-dinitrodiphenylethyleneether. 



(4) The solution to which 4 molecular amounts of nitric acid had been 

 added was allowed to remain at the temperature of the room for 11 weeks. 

 Prom it 2-4-dinitrophenol and oxalic acid in larger amounts than those got 

 in the last experiment were isolated. Rather more than 1 g. of tetranitro- 

 diphenjdethyleneether and 13 g. of the original ether were also obtained, 

 together with a reddish oily substance similar to that mentioned in the last 

 experiment. 



(5) The solution to which 6 molecular amounts of nitric acid had been added 

 on short standing (3 weeks) gave a tarry mass, from which the original 

 ether, 2-4-8-10-tetranitrodiphenylethyleneether and 2-4-dinitrophenol, were 

 isolated. "When the action was allowed to progress for 25 weeks the solution 



