Nitrosation


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Nitrosation

 

replacement of a hydrogen atom in organic compounds by a nitroso group, —N═O. Nitroso compounds, R—N═O, nitrosoamines, RRʹN—N═0, and oximes are formed as a result of nitrosation. For example;

RRʹCHNO2 → RRʹC(NO2)NO

Nitrosating agents, include nitrous acid, HNO2; its esters, RONO; nitrosyl chloride, NOCl; and nitrogen oxides. The active agent in nitrosation is the nitrosonium cation, NO+, which is formed, for example, upon action of strong acids on nitrosating agents.

Nitrosation is used in industry for the production of cyclohex-anone oxime (an intermediate in the production of caprolactam) and of α-diketones and α-amino acids.

Nitrosation was first accomplished by V. Meyer.

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Although there is inadequate human evidence for carcinogenicity, there is sufficient evidence from experimental animals for the carcinogenicity of nitrite in combination with amines or amides, and ingested nitrate under conditions that result in endogenous nitrosation has been classified as probably carcinogenic to humans (IARC 2010).
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Intake of nitrate from drinking water and dietary sources may cause increased exposure to N-nitroso compounds through endogenous nitrosation (Mirvish, 1995).
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