Abstract
The radical initiated addition of (3,5-di-tert. butyl-4-hydroxyphenyl)methane thiol (BHBM, I, R = H) to olefins and its behaviour as an antioxidant are found to be complementary processes. In a system initiated by tert. butyl hydroperoxide (TBH), the adduct process is found to predominate for [BHBM]/[TBH] > 1 whereas radical trapping/peroxidolytic antioxidant reactions occur at molar ratios <1. The antioxidant species have been shown to be sulphur acids, eliminated from the oxidation products of I together with the corresponding sulphonic acid which is stable under the conditions of the reaction.
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