326 Scientific Proceedings^ Royal Dublin Society. 



Trinitrodiphenylene oxide is almost insoluble in ligroin, slightly soluble 

 in alcohol, somewhat soluble in benzene or glacial acetic acid, and readily 

 soluble in acetone. 



(c) Tetranitrodiphenylene Oxide. — 2 g. of 'dinitrodiphenylene oxide was 

 dissolved in a mixture of 10 c.c. of fuming nitric acid and 10 c.c. of concentrated 

 sulphuric acid. The mixture was heated for several hours on the water-bath, 

 a small quantity of colourless crystals being deposited during the course of 

 the experiment. The product was poured into water, and the white solid 

 deposited was washed with water, and dried. The residue left after washing 

 with hot benzene crystallised from xylene as colourless plates, melting at 283° C, 

 which gave on analysis the following results : — 



01075 g. substance gave 14-7 c.c. moist nitrogen at 16° C. and 770 m.m. 



corresponding to N 16-3 

 Ci^H.OgN, requires N 161. 



Tetranitrodiphenylene oxide is veiy slightly soluble in alcohol, somewhat 

 more soluble in benzene, and readUj^ soluble in hot acetic acid, xylene, or acetone. 



Summary. 



1. Diphenylene oxide interacts with nitrogen peroxide or nitric acid much 

 less readily than diphenylnitrosamine. 



2. Nitrogen peroxide vapour converted diphenylene oxide into its dinitro 

 derivative. Nitrogen peroxide in solution in glacial acetic acid, gave the 

 mononitro compound; in carbon tetrachloride it gave the mononitro and the 

 dinitro derivatives. 



3. Fuming nitric acid converted the oxide into its mononitro and its diniti'O 

 derivatives. In cold dilute solution in glacial acetic acid the acid had scarcely 

 any action on the oxide, but in carbon tetrachloride the mononitro compound 

 was formed. This body was also produced by the action of fuming nitric 

 acid on a hot solution of the oxide in glacial acetic acid. 



4. Dinitrodiphenylene oxide was readily produced by the action of fuming 

 nitric acid on a solution of mononitrodiphenylene oxide in glacial acetic acid. 



5. Trinitro- and tetranitrodiphenylene oxides were both formed by the action 

 of fuming nitric acid on the mononitro compound. The tetranitro derivative 

 was also readily obtained by the action of a mixture of fuming nitric acid and 

 concentrated sulphuric acid on dinitrodiphenylene oxide. 



In conclusion we wish to state that the above research was undertaken at 

 the request of the Research Section of Nobel's Explosives Company, and that 

 we are also indebted to the Department of Scientific and Industrial Research 

 for a grant in aid of the investigation. 



