The Reaction of t-Butyl Hydroperoxide with Some Phenols

Abstract

The phenolic antioxidant 2,6-di-t-butyl-£-cresol is converted by reaction with f-butyl hydroperoxide to 1-methyl-1-ibutylperoxy-3,5-di-/-butylcyclohexadiene-2,5-dione-4. This peroxide reacts with bromine in acetic acid to give in high yield 3,5-di-/-butyl-4-hydroxybenzaIdehyde.The efficiency of monohydric phenols as antioxidants varies widely with the type and position of substituents.2-4 Thus phenol itself, which has es-

Phenols as Antioxidants

“…Antiradical efficiency = AE = 1 EC 50 T EC 50 (28) In summary, these are some of the common techniques used to measure lipid peroxidation in the presence and absence of antioxidants, and to study antioxidants directly. There are other techniques, ranging from simple gas chromatographic analysis and measurement of amounts of unoxidized polyunsaturated fatty acids (PUFA) before and after oxidation 83 , to enzyme-mediated assay techniques such as the cyclooxygenase or glutathione peroxidase-based systems 64 .…”

Dihydric Phenols as Antioxidants in Isotactic Polypropylene

“…Great care must be taken in interpreting the results since the half-wave potentials are measured under conditions considerably different from those used to determine antioxidative activity. Other workers (8,30,38) have found a linear plot of logarithms of relative activities vs. redox potentials of antioxidants, which can be expected to occur by the same mechanism. If, however, greater differences can be applied in the action mechanism, the values of redox potentials are then important only for a preliminary judgment of the antioxidant activity: even then it is possible to find within the range of potential values predicted for active substances very weak antioxidants, as we ascertained, for example, when studying the activity of a series of hydroquinone derivatives in lard (29).…”

Interaction of 9-substituted anthracenes with oxidation systems tert-butylhydroperoxide-metal tert-butoxide

“…The reaction mixtures were kept for 2 days at 20°С, but the reaction products II-VIII were detected already after 3 h. As was preliminarily shown, alkylanthracenes do not react DOI: 10.1134/S1070363215060080 (1) with I under the given conditions. As the main products 9-methyl(phenyl)-9,10-dihydro-9,10-di-tert-butylperoxyanthracenes (II, III), 10-methyl(phenyl)-10tert-butylperoxy-9-anthrones (IV, V), 10-hydroxy-10methyl(phenyl)-9-anthrones (VI, VII) were isolated, while in the case of 9-MA also 9-methyl-10-hydro-9,10-epidioxyanthracene (VIII) was found ( Table 1).…”

“…Derivatives of this type were obtained in the reactions of radicals ROO • with some aromatic amines [7] and sterically hindered phenols [2,[8][9][10]. The reaction of hydroperoxide I with 9,10-dimethylanthracene in the presence of alkoxyderivatives of transition metals (acetylacetonates of cobalt, chromium, vanadium, tetra-tert-butoxychromium) is described [6,11].…”