The role of phenols in catalysis of nitrosamine formation

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Abstract
Phenolic compounds which can potentially form C‐nitroso derivatives by reaction with nitrite can act as catalysts on the formation of an N‐nitrosamine from nitrite and a secondary amine. Using a gas chromatographic technique, this effect has been measured for di‐ and trihydric phenols and for a number of naturally occurring phenolic compounds in the case of N‐nitrosodiethylamine (NDEA) formation. The kinetics for this catalytic effect have been studied in detail with dinitrosoresorcinol and two possible mechanisms have been suggested. In addition, it has been shown that a number of naturally occurring phenols catalyse the formation of NDEA under alkaline conditions and such catalysis can lead to the artifactual formation of nitrosamines during their analysis.