N-Nitrosodiphenylamine

Chemical properties

N-Nitrosodiphenylamine is a yellow to orangebrown crystalline solid. Soluble in acetone, benzene, ethyl acetate, dichloromethane, carbon tetrachloride, ether and carbon disulfide, soluble in hot alcohol, slightly soluble in gasoline, insoluble in water. In the hydrochloric acid methanol solution, a shift reaction can occur, and it can be transformed into p-nitrosodiphenylamine.

The Uses of N-Nitrosodiphenylamine

N-Nitrosodiphenylamine is the N-nitroso analogue of diphenylamine that was once used as a rubber additive but is no longer due to undesirable carcinogenic effects (1). N-Nitrosodiphenylamine may have potential carcinogenic activity and is currently classified as a probable carcinogen by EPA with genetic toxicity (2,3). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.

Definition

ChEBI: N-Nitrosodiphenylamine is a member of phenylhydrazines. It is an industrial compound that formerly used as a vulcanization retarder in the rubber industry.

General Description

N-nitrosodiphenylamine appears as yellow to brown or orange powder or flakes or a black solid. Insoluble in water and denser in water. Hence sinks in water. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

N-Nitrosodiphenylamine may be sensitive to moisture at elevated temperatures in strongly acidic solutions. May react vigorously with oxidizing agents. May undergo trans-nitrosation reactions with secondary amines .

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition N-Nitrosodiphenylamine emits toxic fumes of nitrogen oxides.

Fire Hazard

Flash point data for N-Nitrosodiphenylamine are not available; however, N-Nitrosodiphenylamine is probably combustible.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by ingestion. An eye irritant. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. Dangerous fire hazard when exposed to heat, flame, or oxidzing materials. Can react vigorously with oxidizing materials. When heated to decomposition it emits highly toxic fumes of NOx,. See also NITROSAMINES.

Potential Exposure

N-Nitrosodiphenylamine is not a naturally occurring substance; it is a man-made chemical that is no longer produced in the United States. It was used in the manufacture of plastics, resins, rubber and synthetic textiles; to help control processes involved in making rubber products, such as tires and mechanical goods; however, in the early 1980s, the United States manufacturers stopped producing N-nitrosodiphenylamine because new and more efficient chemicals were found to replace its uses. In addition, the use of N-nitrosodiphenylamine had several undesirable side effects which do not occur with the replacement chemicals.

Carcinogenicity

Two feeding experiments with NDPhA in rats were totally negative (no tumors). One used daily doses of 120 mg/kg body weight to a total dose of 65 g/kg, and another used a lower dose for only 53 weeks. Another experiment involved larger groups of rats and mice and higher doses. In mice, after 2 years, there was occasional hyperplasia of the bladder mucosa, but no tumors; in rats given 4000 mg NDPhA/kg diet for 2 years, 16/45 males and 40/49 females had transitional cell carcinomas of the bladder. IARC classified NDPhA as not classifiable as to carcinogenicity in humans (Group 3).

Environmental Fate

Chemical/Physical. At temperatures greater than 85 °C, technical grades may decompose to nitrogen oxides (IARC, 1978). N-Nitrosodiphenylamine will not hydrolyze because it does not contain a hydrolyzable functional group (Kollig, 1993).
At influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 510, 120, 91, and 38 mg/g, respectively (Dobbs and Cohen, 1980).

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with reducing agents may form hydrazine; hydrogen bromide. Light sensitive; rapidly decomposes.

Waste Disposal

Burn in admixture with flammable solvent in furnace equipped with afterburner and scrubber.

References

[1] Peng, Xiuying et al. “Electrochemical sensor for facile detection of trace N-nitrosodiphenylamine based on poly(diallyldimethylammonium chloride)-stabilized graphene/platinum nanoparticles.” New Journal of Chemistry 2 (2018): 820–826.