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Cinnamic acid derivatives, especially esters, were examined as antioxidant in the autoxidation of styrene initiated by azo-bis-isobutyronitrile. A few o-hydroxy-cinnamic acid esters exhibited superior activities of antioxidants to 2,6-di-tert-butyl-4-methylphenol (BHT) which often is used as a standard substrate of phenolic antioxidants. In some cases, the rate constant k inh of a reaction between the ester and peroxy radicals was remarkably higher, for example, about 6 times higher than that of BHT. It was also found, furthermore, that the ester can arrest about four peroxy radicals, notwithstanding that BHT can trap, at highest, only two peroxy radicals. The alcoholic moiety of the ester little affected directly the activity as antioxidant, but the moiety provided a possibility to function as a light absorber similar to the one of benzophenone-type.

Cinnamic Acid Derivatives. (Part 1). Proposal as New Phenolic Antioxidants.