Nitrosamines

Authored by: Pradyot Patnaik

Handbook of Environmental Analysis

Print publication date:  August  2017
Online publication date:  August  2017

Print ISBN: 9781498745611
eBook ISBN: 9781315151946
Adobe ISBN:

10.1201/9781315151946-40

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Abstract

Many nitrosamines may also contain other functional groups, instead of alkyl or aryl groups, such as alcohol. For example, in N-nitrosodiethanolamine, (HOCH2CH2)2N−N=O [1116-54-7], there are two ethanol substitutions on the nitrogen atom attached to the nitroso group. In general, nitrosamines are produced by the reaction of nitrite ion, NO 2 − or any nitrosating agent with a secondary or tertiary amine, R2NH or R3N. Thus, nitrate ion, NO 3 − that commonly occurs in many environmental matrices is susceptible to reduce first to nitrite and then to nitrosamine: nitrate → nitrite → nitrosamine. Nitrite ion and nitrous acid, HNO2 both are, however, weak nitrosating agents. The formation of nitrosamines therefore may involve the following steps: NO 2 − + H + → HNO 2 2 HNO 2 → N 2 O 3 ​ + H 2 O R 1 R 2 NH + N 2 O 3 → R 1 R 2 N ​ - ​ N ​ = ​ O

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