Sur L'influence de la Composition et de la Configuration des Acides Gras Insaturés Isomères sur la Vitesse de L'oxydation par L'acide Peracétique

Smit, W.; Böéseken, J.

doi:10.1002/recl.19300490711

Cited by 12 publications

(2 citation statements)

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“…Several studies have investigated the possible oxidation of organic compounds by PAA and reported that PAA reactivity with respect to organic compounds is very selective. ,,− ,,− Overall, the oxidation mechanism of organic compounds by PAA is the transfer of a single oxygen atom from PAA to electron-rich sites on the compound. PAA reactivity is highly affected by the electron-withdrawing or electron-donating character of the substituents of organic compounds.…”

Section: Reactivity Of Organic Compounds With Respect To Paamentioning

confidence: 99%

“…128 The rate constants for reaction of alkenes with PAA were reported from 3.2 × 10 −6 to 3.7 × 10 −2 M −1 s −1 (Table 2) by four early studies. 46,118,119,126 The reaction rates of PAA with alkenes should be enhanced by an increase in the electron density at the point of attack. Thus, the introduction of neighboring electron-donating groups accelerates the reaction of alkenes with PAA.…”

Section: Reactivity Of Organic Compounds Withmentioning

confidence: 99%

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Reactivity of Peracetic Acid with Organic Compounds: A Critical Review

2020

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As an emerging oxidant and disinfectant, peracetic acid (PAA) has increasingly been used in wastewater treatment and the food and medical industries and has attracted greater research interest. To better understand reactions initiated by PAA, this paper is among the first to comprehensively review the reactivity of PAA with respect to organic compounds of various structures. The reactivities of PAA with respect to 123 organic compounds are compiled from the literature and new experiments, and possible reaction pathways and products are discussed. Overall, PAA is an electrophile with high selectivity in reaction. The second-order rate constants of PAA oxidation of organic compounds vary by nearly 10 orders of magnitude, from 3.2 × 10 −6 to >1.0 × 10 5 M −1 s −1 , which are much larger than those of H 2 O 2 coexisting in PAA solutions. Electron-donating groups of compounds increase the reactivity with respect to PAA, evidenced by the strong negative correlations between rate constants and substituent constants [Hammett (σ) or Taft (σ*)] of compounds. Sulfur moieties show exceptionally high reactivity with respect to PAA. Limited studies have shown that generally oxygen-added reaction products are formed from PAA oxidation. This critical review provides a useful foundation for advancing our understanding of the fate of organic compounds in wastewater treatment including PAA and identifies further research needs to evaluate a broader range of compounds and their oxidation products and toxicity.

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Section: Reactivity Of Organic Compounds With Respect To Paamentioning

confidence: 99%

Section: Reactivity Of Organic Compounds Withmentioning

confidence: 99%

Reactivity of Peracetic Acid with Organic Compounds: A Critical Review

2020

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Epoxidation and Hydroxylation of Ethylenic Compounds with Organic Peracids*One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.

Swern

2011

Organic Reactions

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Oxiranes and alpha‐glycols can be prepared from olefins by a variety of methods. One of the most important and generally applicable of these is the oxidation of ethylenic compounds with organic peracids. Depending on the peracid employed and/or operating conditions either an oxirane or an alpha‐glycol can be obtained in good yield. It is important to note that the oxidation step both in epoxidation and hydroxylation reactions with organic peracids is the conversion of the olefin to the oxirane.

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Böeseken Oxidation

2010

Comprehensive Organic Name Reactions and Reagents

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The transformation of the α,β‐unsaturated carbonyl compounds into enol esters or aromatic carbonyl molecules (benzaldehys or phenyl ketones) into phenol esters via oxygen insertion from the alkaline oxidation by peracids is known as Böeseken oxidation. The migration of an alkyl or aryl group to an electron‐deficient oxygen atom has been indicated and the migratory aptitude of groups from ketone under alkaline peroxide oxidation is found in the order of primary alkyl >secondary alkyl > methyl and phenyl. This reaction has been found to prepare different phenols, enol esters and aldehydes.

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Sur L'influence de la Composition et de la Configuration des Acides Gras Insaturés Isomères sur la Vitesse de L'oxydation par L'acide Peracétique

Cited by 12 publications

References 1 publication

Reactivity of Peracetic Acid with Organic Compounds: A Critical Review

Reactivity of Peracetic Acid with Organic Compounds: A Critical Review

Epoxidation and Hydroxylation of Ethylenic Compounds with Organic Peracids*One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.

Böeseken Oxidation

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