Studies on the formation of nitrosamines. VIII. The effects of ethanol, glucose and sucrose on nitrosation of secondary amines following alkalization of reaction mixture.

Abstract

When diethylamine (DEA) was reacted with sodium nitrite at pH 3 in the presence and absence of ethanol, glucose or sucrose, followed by alkalization with sodium hydroxide to terminate the reaction, nitrosodiethylamine (NDEA) formation was stimulated by the addition of ethanol, glucose or sucrose. However, these compounds had no effect on NDEA formation when the reaction was terminated by the addition of sulfamic acid. Further, when the mixed solution of sodium nitrite and ethanol, glucose or sucrose was first acidified to pH 3, next alkalized to pH 13, and then combined with DEA, NDEA was formed in proportion to the concentration of ethanol, glucose or sucrose. NDEA was also formed in the reaction of DEA and ethylnitrite in basic medium. It can be probably postulated that the corresponding nitrous acid ester is formed from sodium nitrite and ethanol, glucose or sucrose in acidic medium and nitrosates DEA in alkaline medium. It should be noted that apparent stimulation occurs in nitrosation of secondary amines in the presence of compounds having alcoholic hydroxyl groups when reaction is terminated by alkalization.