Section III, 1918 [7] Trans. R.S.C. 



Constitution of Certain Polynitro Compounds. 



By J. Bishop Tingle and Walter Albert Lawrance.* 



Presented by Dr. R. F. Ruttan, F.R.S.C. 



(Read May Meeting, 1918.) 



Bishop Tingle and Blank,^ in the course of their investigation of 

 the action of nitrating agents on a number of iV-acyl anilines, obtained 

 two compounds by the nitration of Picranilid and one by the action 

 of Nitric Acid on Diphenylamine; they did not describe them. 



Bishop Tingle and Burke ^ found all three to ba tetranitrodi- 

 phenylamines; but they did not identify them. 



The object of the present research was to identify these com- 

 pounds. 



I. The product obtained by the action of Nitric and Oxalic 

 Acids on Picranilid is a bright lemon-yellow, granular powder, which, 

 after recrystalizing twice from alcohol, melted at 2 15°» 5. Analysis 

 shows it to be a tetranitrodiphenylamine. All attempts to hydrolyze ' 

 this compound failed. The 2,4,6,4' — tetranitrodiphenylamine was 

 then prepared. This, after purifying with alcohol, had an M.P. of 216°. 

 A mixture of these two melted at 216°; a proof of their identity. 

 Thus the product of the above nitration is 2,4,6,4' — tetranitrodi- 

 phenylamine, C6H2(N02)3NH(C6H4N02). 



II. Trichloracetic and Nitric Acids act upon Picranilid forming 

 two compounds; (a) one which is soluble in Benzene and (b) a second 

 soluble in Alcohol. 



(a) The product soluble in Benzene was recrystallized twice 

 from this solvent. It is a light-brown, crystalline substance melting 

 at 190-1°, and is soluble in Sodium Hydroxide, developing a dark 

 red colour when warmed. The melting point and colour reaction 

 agree with those of the compound described in the literature as being 

 probably symmetrical.^, ^ It is identical with substances des- 

 scribed under Illb and IIIc. 



•Dissertation submitted in part requirement for the 'Master of Arts Degree by 

 Walter Albert Lawrance, B.A., (McMaster). 



^Journal of the American Chemical Society, 30, 1411. 

 ^Journal of the American Chemical Society, 31, 1315, 

 ^Austin, Ber. 7, 1247; Wedekind, Ber. 33, 432. 

 *Beilstein, II, 340. 



