Reaction of aliphatic tertiary amines with hydroperoxides

Trioctylamine acts as an antioxidant in fats at 70C but not at lower temperatures. A reactive antioxidant intermediate was sought. Dioctylhydroxylamine was obtained from the reaction of trioctylamine and t-butyl peroxide at 70C. The recrystallized product had antioxidant properties. About 0.1% existed as stable free radical by electron-spin resonance. Didecyl- and didodecylhydroxylamines were also synthesized from the corresponding tertiary amines. These and a sample of commercial diethylhydroxylamine also contained free radicals and possessed antioxidant activity.