Quantum-Mechanical Studies on Oxidation Potentials and Antioxidizing Action of Phenolic Compounds.

Fueno, Takayuki; Ree, Taikyue; Eyring, Henry

doi:10.1021/j150581a034

Cited by 39 publications

(19 citation statements)

References 3 publications

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“…The relationship of the relative activity to E0 is demonstrated in Figure 6. The activity decreases in the potential range 753-780 mv., lying in the range usually given for active antioxidants (6,11,12,14,18,21,24,29) with increasing half-wave potential; a similar relationship can be observed by comparing the series of 4-alkyl derivatives of pyrocatechol, substituted by methyl and tertiary alkyl groups (Figure 4) and the series of monohydric, differently substi tuted phenols (6,14).…”

Section: ) For 4-alkylpyrocatecholssupporting

confidence: 71%

Dihydric Phenols as Antioxidants in Isotactic Polypropylene

Pospı́šil

Taimr

Kotulák

1968

Advances in Chemistry

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The activity of the 4-alkylpyrocatechols (Ia), 3-alkylpyrocatechols (Ib), 3,5-dialkylpyrocatechoh (Ic), 3,6-dialkylpyrocatechols (II), 4,5-dialkylpyrocatechols (III), 3,4,6-trialkylpyrocatechol (IV), and 4,5-and 4,6-dialkyl-2-alkoxyphenols (V and VI) was studied in isotactic polypropylene at 180 ± 0.1°C. The rehtive activities A r were correlated with substituent constants and redox potentials. In the Ia series the activity of 4-n-alkyl derivatives exceeded that of 4-tert-alkyl derivatives. The length of the main alkyl chain in Ia and Ib and the steric effects in the latter exerted a specific favorable influence. In agreement with these effects, 3-tertalkyl-5-methyl derivatives are the most active compounds in Series Ic; compounds with other combinations of alkyls are weaker antioxidants as are the isomeric substances II and III or compound IV. Etherification of one hydroxyl group exerts an unfavorable effect; influences of substitution in 2-alkoxyphenols (V and VI) are generally the same as in the pyrocatechols I-III. *ΊΓ*ο stabilize polypropylene against oxidation by atmospheric oxygen, A phenolic mononuclear and polynuclear antioxidants containing one hydroxyl group on the aromatic nucleus are used successfully. Thus far the behavior of antioxidants having the structure of polyhydric phenols has not been studied extensively for stabilizing polyolefins. We have systematically observed the properties of dihydric mononuclear phenols with the structure of pyrocatechol and hydroquinone in isotactic poly-169 Downloaded by MICHIGAN STATE UNIV on February 18, 2015 |

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Section: ) For 4-alkylpyrocatecholssupporting

confidence: 71%

Dihydric Phenols as Antioxidants in Isotactic Polypropylene

Pospı́šil

Taimr

Kotulák

1968

Advances in Chemistry

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“…This fact led Fueno, et al (1959) to conclude that in each oxidation the rate determining step involves abstraction of one electron from the highest occupied orbital. Thus, the easier it is to form a radical, the faster the reaction should be.…”

Section: Nonreactive Sorbatesmentioning

confidence: 99%

Irreversible adsorption of phenolic compounds by activated carbons

Grant¹,

King²

1988

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“…Reduction peaks for calculating the apparent redox potentials (E1 2) were not observed. The Ep values suggested the glucosides were similar in electrochemical (redox) reactivity; 12,16) or rather, α Arb was slightly more reactive than β Arb, which did not agree with the experimental results on the enzyme specificity (Fig. 6).…”

Section: Oxidation Potential and Reactivity Of Arbs With Peroxidasesmentioning

confidence: 70%