N-Nitrosodiphenylamine

Various nonvolatile nitrosamines were analyzed using HPLC-UV photolysis-CLD. This was applied for determination of V-nitrosamides in dried squid589 and N-nitrosodiphenylamine (278c) in treated apples590. 

C-polyaromatic hydrocarbons deoxyribonucleic acid environmental Protection Agency peroxy nitric acid nitric acid lipopolysaccharide nitrogen/Carbon isocynate radical N-nitrosodibuty lamine N-nitrosodiethylamine N-nitrosodiethanolamine N-nitrosodimethylamine N-nitrosodiphenylamine N-nitrosoethylmethylamine... 

An EPA method was created for measuring NDMA and six additional nitrosamines in drinking water (EPA Method 521) [55]. This method uses GC/ chemical ionization (CI)-MS/MS and enables the measurement of NDMA and six other nitrosamines (N-nitrosomethylethylamine, N-nitrosodiethylamine, N-nitroso-di-n-propylamine, N-nitroso-di- -butylamine, N-nitrosopyrrolidine, and N-nitrosopiperidine) in drinking water at detection limits ranging fi om 1.2 to 2.1 ng/L. A liquid chromatography (LC)/MS/MS method [56] can also be used to measure nine nitrosamines, including N-nitrosodiphenylamine, which is thermally unstable and cannot be measured using the EPA Method. 

ACGIH has not established a threshold limit value (TLV) for N-nitrosodiphenylamine. 

Toxicology. N-nitrosodiphenylamine (NDPhA) is an animal carcinogen and causes bladder tumors in male and female rats. 

Agency for Toxic Substances and Disease Registry (ATSDR) Toxicological Profile for N-nitrosodiphenylamine. pp 1-79. US Department of Health and Human Services, Public Health Service, 1993... 

National Cancer Institute Bioassay of N-Nitrosodiphenylamine for Possible Carcinogenicity. DHEW (NIH) Pub No 79-1720. Washington,... 

Cardy RH, Lijinsky W, Hilderbrandt PW Neoplastic and non-plastic urinary bladder lesions induced in Fischer 344 rats and B6C3F1, hybrid mice by N-nitrosodiphenylamine. Ectotoxicol Environ Safety 3 29-35, 1979... 

Thanks are due to the Editor of this volume for suggesting the similarity of N,N-disubstituted carbamoyl nitrites to the a-amino nitrite esters discussed above. When N,N-diphenyl carbamoyl chloride was refluxed with sodium nitrite in acetonitrile solution for 24 hours, N-nitrosodiphenylamine was produced in quantitative yield (M. Nakajima and J.-P. Anselme, unpublished results). The N,N-dibenzyl derivative underwent a similar reaction with nitrite. The mechanism shown in Fig. 13 was postulated to account for these transformations. 

The following compounds, with no observed carcinogenic activity, are not included in the table N-nitrosodiphenylamine, N-nitrosodicyclohexylamine, N-nitrosodiallylamine and N-nitrosodibenzylamine. Substituent constants (a ) are based on the following structure ... 

In a preliminary study we have recently reported (1) that the air in three rubber and tire industry plants was contaminated with several N-nitroso compounds. The compounds included N-nitrosomorpholine (NMOR), N-nitrosodimethylaminne (NDMA), and N-nitrosodiphenylamine (NDPhA). The latter compound is used as a vulcanization retarder, so its presence near processes employing it was not surprising. Bismorpholine-carbamylsulfonamide, a cross-linking accelerator used in rubber tires was found in tire factories and may be contaminated with NMOR. The source of the NDMA was not identified, but it could arise from nitrosation of amines which may be decomposition products of diamine based accelerators, as pointed out by Yeager, et al (2). 

Local exhaust improved-canopy inclosed on 3 sides Rubber formulation change n-nitrosodiphenylamine not used. 

N-Nitrosodiphenylamine (III) which is formed first, has been proved experimentally to be nearly as good a stabilizer as diphenylamine itself. Neither of the above substances gives powders an intense coloration. 

Davis and Ashdown devised methods for detecting these substances in powder. If the alcoholic extract from powder contains diphenylamine it forms a blue colour with ammonium persulphate N-nitrosodiphenylamine gives no coloration with this reagent. The intensity of the colour developed by a mixture of both substances evidently depends upon the concentration of diphenylamine. On the other hand N-nitrosodiphenylamine gives an intense blue coloration to concentrated sulphuric acid. 

Another test for N-nitrosodiphenylamine is based on the treatment of an alcoholic solution of this substance with a 1 % alcoholic solution of a-naphthylamine followed by heating, when it turns orange. 

It is generally agreed that powder in which diphenylamine is completely converted into N-nitrosodiphenylamine is suitable for storage. However, on the disappearance of N-nitrosodiphenylamine and its conversion into nitro compounds, the powder should be considered unsuitable for storage since it then lacks a stabilizer. 

Other more complex examples are known,156-167 of which some are tranquillizing, antiasthmatic, or analgesic.I56,I57J6S The parent triazolo-[4,5-b]pyridine 4 has also been made from 1,2-diaminopyridine with N-nitrosodiphenylamine.168 If N-substituted diaminopyridines are used, N-sub-stituted triazolopyridines can be obtained.I53,169 l8° Examples are provided by... 

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