DOI: 10.1246/bcsj.49.1632. Retardation of Autoxidation in the Presence of Water, Alcohols and Carboxylic Acids

Retardation of Autoxidation in the Presence of Water, Alcohols and Carboxylic Acids

10.1246/bcsj.49.1632

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract The oxidation of alcohols and α-substituted toluenes in water, methanol and acetic acid was studied at 60–70 °C in the presence of 0.040 M AIBN. The rate of oxidation of alcohol, kp/(2kt)1⁄2, considerably increases when the alcohol is diluted with an inert solvent. The rate remarkably decreases with the addition of water, methanol or various carboxylic acids. However in the presence of tetralyl hydroperoxide, viz., when the hydroperoxyl radical is replaced by the tetralyl peroxyl radical, no further inhibition effect due to water, methanol or carboxylic acids is observed. The rate of oxidation of 1,4-cyclohexadiene decreases with the addition of water or acetic acid. However in the presence of 0.20 M tetralyl hydroperoxide, no further inhibition effect is observed. The rate of oxidation of 1-phenylethanol decreases with the addition of benzoic acid but not with that of methylbenzoate. The rate of oxidation of (2-chloroethyl) benzene, ethylbenzene and isopropylbenzene does not decrease with the addition of 0.224 M acetic acid, but that of N,N-dimethylbenzylamine, N,N-diethylbenzylamine, benzyl alcohol, 1-phenylethanol and methyl benzyl ether decreases. It is concluded that hydroperoxyl and alkylperoxyl radicals with α-substituents such as hydroxyl, carbonyl, alkoxyl or amino groups undergo deactivation due to hydrogen bonding with water, alcohols and carboxylic acids.

Bibliography

Ukegawa, K., & Kamiya, Y. (1976). Retardation of Autoxidation in the Presence of Water, Alcohols and Carboxylic Acids. Bulletin of the Chemical Society of Japan, 49(6), 1632â1637.

Authors 2

Koji Ukegawa (first)
Yoshio Kamiya (additional)

References 21 Referenced 8

10.1021/ar50013a001
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10.1021/ja01066a014
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10.1139/v63-295
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10.1246/bcsj.40.583
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10.1139/v67-131
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Dates

Type	When
Created	19 years, 1 month ago (July 19, 2006, 10:45 p.m.)
Deposited	1 year, 7 months ago (Jan. 16, 2024, 11:22 p.m.)
Indexed	1 year, 7 months ago (Jan. 17, 2024, 7:02 p.m.)
Issued	49 years, 2 months ago (June 1, 1976)
Published	49 years, 2 months ago (June 1, 1976)
Published Online	19 years, 4 months ago (April 19, 2006)
Published Print	49 years, 2 months ago (June 1, 1976)

Funders 0

None

BibTeX

@article{Ukegawa_1976, title={Retardation of Autoxidation in the Presence of Water, Alcohols and Carboxylic Acids}, volume={49}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.49.1632}, DOI={10.1246/bcsj.49.1632}, number={6}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Ukegawa, Koji and Kamiya, Yoshio}, year={1976}, month=jun, pages={1632–1637} }

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