IIyan & Kenny — Action of Oxides of Nitrogen on Diphenylethyleneether. 309 



contained 45 g. of suspended solids, amongst which were some large colourless 

 prisms of oxalic acid (about 1 g.). The filtered solids were washed with water, 

 alcohol, and ether, and then reerystalUsed from xylene, from which about 

 1 g. of pure tetranitrodiphenylethyleneether, melting at 214° C, separated. 

 Aqueous potash extracted 0-3 g. of pure 2-4-dinitrophenol from the carbon 

 tetrachloride filtrate. A small amount of a reddish oily semi-crystalline 

 substance was also obtained, but was not further examined. 



3. Action of Nitric Acid on NitrodiphenyletJiyleneether. 



2-Nitrodiphenylethyleneether (2 g.) was added slowly to 5 parts nitric 

 acid (Sp. g. 1-51) with which it reacted energetically with formation of a 

 red solution, and, after a short time, with a separation of a crystalline solid. 

 The mixture was let remain at the temperature of the room for 2 days; 

 it was then poured into water, and the solid which separated was filtered and 

 dried. Alcohol separated from this a very small quantity of an oily body, 

 which was not further examined. By recrystallising the residue from xylene 

 it was separated into tetranitrodiphenylethyleneether, melting at 214° C, 

 and a more soluble crystalline solid, melting at 172° C. The latter substance 

 gave on analysis the following results : — 



0-137 g. substance gave 13-8 c.c. moist nitrogen at 16° C. and 764 m.m. 



corresponding to N 1189 

 Ci^HjiOsNj requires N 1203. 



The substance was therefore a trinitrodiphenylethyleneether. 



4. Action of Nitric Acid, on d-Nitrodiphenylethyleneether. 



3 g. of p-nitrodiphenylethyleneether were added slowly to 15 g. of nitric 

 (Sp. g. 151), and the mixture was allowed to remain overnight at the 

 temperature of the room. It was then poured into water, and the solid 

 which separated was filtered and washed with water, alcohol, and ether. It 

 weighed 2-9 g., and consisted of nearly pure tetranitrodiphenylethyleneether.- 

 A dark-coloured impure substance, melting between 140 and 160° C, was also 

 obtained, but the amount was insufficient for further examination. 



5. Action of Nitric Acid on 2-8-Dinitrodiphenylethyleneether. 



Nitration of the dinitro derivative, by a method analogous to that employed 

 above in the case of the 2-nitro derivative, gave a product from which we 

 isolated trinitrodiphenylethyleneether, melting at 172° C, and tetranitro- 

 diphenylethyleneether, melting at 214° C. 



6. Action of Nitric Acid on 410-DinitrodipJienylethyleneether. 



4-10-Dinitrodiphenyleneether (1 g.) was added to 5 parts of nitric acid 

 (Sp. g. 1-51), and the crystals which separated after about 3 hours were 

 removed, washed, dried, and recrystallised from xylene. About 095 g. of 

 tetranitrodiphenylethyleneether, melting at 214° C, were thus obtained. 

 When the nitric acid solution, which had been separated from the crystals, 

 was poured into water about 02 g. of the solid separated, and this, after 

 crystallisation from alcohol and xylene, melted between 185 and 210° C, 

 probably consisting of a mixture of the tetranitro compound with the 

 unchanged parent substance. 



