10 THE ROYAL SOCIETY OF CANADA 



compounds obtained as described in 1 1 lb and I lie. Its solubilities 

 are the same as these. 



(b) The product recrystallized from Alcohol is a dark brown 

 powder melting at 179-80°. It is soluble in Acetone, slightly soluble 

 in Ether, but insoluble in Carbon Tetrachloride. The properties of 

 this compound agree with those described of Bis. -2, 4 — tetranitrodi- 

 phenylamine.^ 



III. The nitration of diphenylamine was carried out with diffi- 

 culty. One molecular proportion of diphenylamine was placed in a 

 large beaker, surrounded by ice water, and eight molecular proportions 

 of Nitric Acid were added. The acid was slowly poured in, stirring 

 at intervals, thoroughly cooled, and water was then added. The 

 product was washed with warm water until free from acid. 



(a) The portion soluble in hot nitrobenzene was precipitated 

 by the addition of Ethyl Alcohol to the solvent. It melts above 250°. 

 It is slightly soluble in Ether, Acetone, Chloroform and Alcohol, 

 insoluble in Petroleum Ether and Carbon Tetrachloride. Analysis 

 shows it to be a tetranitrodiphenylamine ; found C.41-20, calculated 

 C.41-29. The 2,4,6,2' — and 2,4,6,3' — tetranitrodiphenylamines were 

 prepared from Picryl Chloride and ortho- and meta-nitraniline 

 respectively. "Beilstein" describes the 2,4,6,2' — ■ compound as 

 melting "near 220°"; we found it to be 233-4° (approximately as 

 given by Richter). The melting points of a mixture of each of these 

 compounds with the above substance proved that the latter is not 

 identical with either. 



(b) (c) One of the products of nitration is soluble in Ethyl Ace- 

 tate and can be precipitated from this solvent by Petroleum Ether. 

 Xylene extracts a substance which is identical with that soluble in 

 Ethyl Acetate. These two are identical with that described under 

 I la. The melting points of the several mixtures are as follows: 



Alone: lia 190-1°, Illb, 191-2°, IIIc, 190-1°. 

 Mixed: Ila + IIIb, 191-2°. Ila + IIIc. 191°. 

 Illb + IIIc, 191°. 

 Ila-flllb-flllc, 191°. 

 All three compounds give the same red colour reaction with 

 warm Sodium Hydroxide. All are insoluble in Ether, Petroleum 

 Ether and Carbon Tetrachloride; slightly soluble in Alcohol and 

 Chloroform; soluble in Acetone. 



(d) The remaining portion is insoluble in Xylene, Ether and Carbon 

 Tetrachloride, it is slightly soluble, however, in both Acetic Anhy- 

 dride and Ethyl Alcohol. The yield was poor, and time did not 



'Hager, Ber. 17, 2629. 



