P-nitrosodiphenylamine

Montmorillonite KIO clay and its various cation-exchanged forms have been found to promote the formation of an unexpected product, p-nitrosodiphenylamine, from iV-phenylhydroxylamine, rather than the typical Bamberger products. A Bamberger rearrangement has been shown to occur during the metabolism of 2,4,6-trinitrotoluene... 

With mineral acids, including nitric acid produced by the decomposition of powder, the N-nitroso compound undergoes rearrangement to form p-nitrosodiphenylamine (IV). This substance is readily oxidized to p-nitrodiphenylamine (V). Furthermore, the higher nitrated products, i.e. dinitro derivatives (VI) and (VII) and trinitro derivatives (VIII) may be formed in powder. Davis and Ashdown isolated 2,4,4 -tri-nitrodiphenylamine from American pyrocollodion powder by heating a sample in a closed vessel for 240 days at a temperature of 65°C. At the end of the heating period brown nitric oxides were given off by the powder. 

Methylphenylnitrosoamine E thylpheny Ln itrosoamine Nitrosobenzene o-Nitrosotoluene. m-Nitrosotoluene. p-Nitrosotoluene. a-Nitrosonaphthalene. p-Nitrosophenol. a-Nitroso-P-naphthol. 4-Nitroso- a-naphthol pNitrosoNNdimethylaniline p-Nitroso -NN diethylani line. p-Nitroso-N-methylaniline p-Nitroso-Nethylaniline p-Nitrosodiphenylamine... 

Benzeneamine, N-hydroxy-N-nitroso,ammonium salt NItrilotrlacetic acid 4,4 -Thiodianillne Ethyl acrylate Butyl acrylate Ethyleneimine (Aziridine) p-NItrosodiphenylamine Calcium cyanamide Hydrazine Aldrin... 

The first change which takes place in storage of DPhA contg proplnts is the formation of Diphenyl-H-nitrosamine, CgH(j.N(NO).CgH.(j. The presence of this compd (which is as good a stabilizer as DPhA itself) was proven in all proplnts which were not too old or which had not suffered profound decompn. If any mineral acid is present it undergoes a tautomeric change with the formation of p-Nitrosodiphenylamine, CgHj.NH.CgH 4.NO. 

A serious disadvantage of conventional antioxidants is their loss from the polymer matrix either by solvent extraction or volatility, resulting in loss of the useful life of the products via degradation or embrittlement (I). This disadvantage is surmounted by chemically attaching the antioxidant to the polymer. The recent literature describes several methods and techniques to accomplish this (2). For example, aromatic nitroso compounds (p-nitrosodiphenylamine or N,N-diethyl-p-nitrosoaniline) bind to rubber when an allylic hydrogen is present (3). 

Benzenamine, 4-nitroso-N-phenyl-. See p-Nitrosodiphenylamine Benzenamine, N-nitroso-N-phenyl-. See Nitrosodiphenylamine... 

Diphenylamine, 4,4 -dioctyl-. See p,p -Dioctyldiphenylamine Diphenylamine, 4-isopropoxy-. See p-Isopropoxy diphenylamine Diphenylamine, a-methylstyrenated. See 4,4 -Dicumyl diphenylamine Diphenylamine, 2-nitro-. See 2-Nitrodiphenylamine Diphenylamine, 4-nitroso-. See p-Nitrosodiphenylamine Diphenylamine, N-nitroso-. See... 

Nitrosodiphenylamine. See p-Nitrosodiphenylamine N-Nitrosodiphenylamine. See Nitrosodiphenylamine p-Nitrosodiphenylamine CAS 156-10-5 EINECS/ELINCS 205-848-7 Synonyms Benzenamine, 4-nitroso-N-phenyl- Diphenylamine, 4-nitroso- 4-N itrosodi phenyl am i ne 4-N itroso-N-phenylaniline p-Nitroso-N-phenylaniline 4-N itroso-N-phenyl benzenam i ne N-Phenyl-p-nitrosoaniline... 

Phenylnitrobenzene. See 2-Nitro-1,1 -biphenyl Phenyl 2-nitrophenylamine. See 2-Nitrodiphenylamine N-Phenyl-p-nitrosoaniline. See p-Nitrosodiphenylamine Phenyloxirane 1-Phenyloxirane 2-Phenyloxirane. See Styrene oxide Phenyl paraben... 

C12H10N2O Azoxybenzene Nitrosodiphenylamine p-Nitrosodiphenylamine C12H10N2O2 2-Nitrodiphenylamine 4-Nitrodiphenylamine Solvent orange 1 C12H10N2O5S Na Acid orange 6... 

Pieryl ddoride add. comp. m.p. 63-4°. N-NUroso diphenylnitiosamine. C42H10ON2. MW, 198. Yelbw plates. M.p. -5°. Sol. warm EtOH, warm CgHg. Ale. HCl —> p-nitrosodiphenylamine. 

Of the derivatives of p-phenylenediamine, the most effective are the N, N -di-alkyl derivatives, in which the alltyl possesses a branched hydrocarbon chain on the carbon closest to the nitrogen atom [235]. They are usually produced by reductive allq lation of p-nitroaniline, p-phenyl-enediamine, p-nitrodiphenylamine, p-nitrosodiphenylamine, or p-amino-diphenylamine with aldehydes and ketones [236-252] with hydrogen at a temperature of 100-250°C and a pressure from 5 to 200 atm in the presence of catalysts. Copper-chromium catalysts (mixtures of oxides of the metals chromium, copper, barium, etc.) [241, 242, 245-247, 249, 250], iodine in the presence of HCl, HBr, or HI [253, 254], Pt/C [245, 252], and Raney nickel [244] are most often used as the catalysts. 

A soln. of p-nitrosodiphenylamine in NaOH-soln. cooled, the air replaced by Ng, evacuated, shaken and treated with nitric oxide until absorption is complete Na-p-(N-nitrosohydroxylamino)-N-nitrosodiphenylamine. Y 58%. F. e. s. M. J. Danzig and S. R. Riccitiello, J. Org. Chem. 27, 686 (1962). 

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