Mrzewinski, Tadeusz published the artcileReactions of nitrogen dioxide with diphenylamine, Safety of Bis(4-nitrophenyl)amine, the publication is Biuletyn Wojskowej Akademii Technicznej imienia Jaroslawa Dabrowskiego (1964), 13(138), 59-67, database is CAplus.
An amount of 4.78-6.66 g. dry gaseous NO2, either O-free or containing 0.66-0.75 mol O per mol, was passed into a solution of 10 g. Ph2NH in 130 mL. C6H6, either without catalyst or with 0.01 mg. N,N-diphenyl-N’-picrylhydrazide (I), or with Bz2O2. The mixture was refluxed 0.5-3.5 h. at 20 or 77¡ã. The mixture was refluxed 0.5-3.5 h. at 20 or 77¡ã. The products were separated by means of fractional crystallization from acetone and were identified by determination of the m.p., mol. weight, and N content and also polarog. as weil as spectrophotometrically. The following products and yields were obtained, without catalysts at 20¡ã: N-nitroso-4-nitrodiphenylamine (II) 0.28 g. and N-nitrosodiphenylamine (III) in trace amount; with O at 20¡ã: II 0.20 g., III in trace amount, and diphenyldihydrophenazine (IV) 0.02 g.; with O at 77¡ã: II 0.15 and 2,4-dinitrodiphenylamine (V) 0.06 g.; with O and I at 20¡ã: II 0.70, III 0.10, V 0.30, 4,4′-dinitrodiphenylamine (VI) 0.22, 4-nitrodiphenylamine (VII) 0.10, and N,N’-bis(2,4-dinitrophenyl)benzidine (VIII) 0.90 g.; with O and I at 77¡ã: II and VI in trace amounts and V 0.20 g.; with 0.01 g. Bz2O2 at 20¡ã: II 0.84, III 0.41, V 0.42, VI 0.34, and N,N’-bis(4-nitrophenyl)benzidine (IX) 0.09 g.; with O and 0.01 g. of Bz2O2 during 3.5 h.: II 0.80, V 0.57, VI 0.31, VIII 0.15, IX 0.13, and 2,4,4′-trinitrodiphenylamine (X) 0.20 g.; with O and 0.10 g. Bz2O2 during 0.5 h.: II 0.64, V 0.50, VI 0.27, VII 0.19, IX 0.18, and X 0.32 g. A free-radical mechanism of the reaction is suggested according to the equation: Ph2NH + NO2 ¡ú Ph2N¡¤ + HNO2. The catalysts are considered to initiate the formation of radicals.
Biuletyn Wojskowej Akademii Technicznej imienia Jaroslawa Dabrowskiego published new progress about 1821-27-8. 1821-27-8 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Amine,Benzene, name is Bis(4-nitrophenyl)amine, and the molecular formula is C12H9N3O4, Safety of Bis(4-nitrophenyl)amine.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia