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image/svg+xml Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Closed Access logo, derived from PLoS Open Access logo. This version with transparent background. http://commons.wikimedia.org/wiki/File:Closed_Access_logo_transparent.svg Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Journal of the Ameri...arrow_drop_down
image/svg+xml Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Closed Access logo, derived from PLoS Open Access logo. This version with transparent background. http://commons.wikimedia.org/wiki/File:Closed_Access_logo_transparent.svg Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao
Journal of the American Oil Chemists Society
Article . 1995 . Peer-reviewed
License: Wiley Online Library User Agreement
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Antioxidant synergism between butylated hydroxyanisole and butylated hydroxytoluene

Authors: Kanji Omura;

Antioxidant synergism between butylated hydroxyanisole and butylated hydroxytoluene

Abstract

AbstractDecay of the 2,6‐di‐tert‐butyl‐4‐methylphenoxy radical [butylated hydroxytoluene (BHT)‐radical] in the presence of butylated hydroxyanisole (BHA) was investigated in 1,2‐dimethoxyethane with or without triethylamine. BHT‐radical was conveniently generated by dissociation of its unstable dimer in solution. The products were BHT, 3,3′‐di‐tert‐butyl‐5,5′‐dimethoxy‐2,2′‐dihydroxybiphenyl (BHA‐dimer), 2,6‐di‐tert‐butyl‐p‐quinone methide (QM), 1,2‐bis(3,5‐di‐tert‐butyl‐4‐hydroxyphenyl)ethane, and 3,3′,5,5′‐tetra‐tert‐butyl‐4,4′‐stilbenequinone. The reaction without added triethylamine gave larger quantities of the last two products and BHA (recovery), whereas the reaction with it provided larger quantities of the first two products. The marked difference in the product distribution can be accounted for by a series of reactions including reversible dehydrogenation of BHA with BHT‐radical, which generates 2‐tert‐butyl‐4‐methoxyphenoxy radical (BHA‐radical) and BHT, reversible dimerization of BHA‐radical, which affords an intermediarybis(cyclohexadienone), and spontaneous and base‐catalyzed prototropic rearrangement of the intermediate into BHA‐dimer. Products of coupling between BHT‐radical and BHA‐radical were not obtained. BHA was found to undergo facile acid‐catalyzed addition to QM, providing two isomericbis(hydroxyphenyl)methanes. The results help to elucidate the mechanism of antioxidant synergism between BHA and BHT and may suggest that the synergism can be affected by base or acid.

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
25
Top 10%
Top 10%
Average
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