Organophosphorus antioxidants: Part X—Mechanism of antioxidant action of aryl phosphites and phosphonites at higher temperatures

Schwetlick, K.; Pionteck, Jürgen; Winkler, Anja; Hähner, Ulrike; Kroschwitz, Herbert; Habicher, Wolf D.

doi:10.1016/0141-3910(91)90077-5

Cited by 52 publications

(21 citation statements)

References 7 publications

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“…Additionally, 2,4-ditert-butyl phenol (2,4-DTBP) during the degradation test was found. It was known that 2,4-DTBP could be used for pesticide production (Schwetlick et al 1991).…”

Section: Pf Intermediate Metabolite Detectionmentioning

confidence: 99%

Profenofos insecticide degradation by novel microbial consortium and isolates enriched from contaminated chili farm soil

Siripattanakul‐Ratpukdi

Vangnai

Sangthean

et al. 2014

Environ Sci Pollut Res

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Profenofos (PF) is one of the heavily used organophosphorus pesticides (OPPs) of which its contamination is ubiquitous in an agricultural area. This study aims to acquire and characterize PF-degrading bacterial cultures from contaminated soil. OPP degradation by the novel isolates was then investigated. The experiment was performed at the initial PF concentration of 20 mg/L. The result showed that the enriched consortium comprised three predominant PF-degrading strains designated as PF1, PF2, and PF3. The isolates (PF1, PF2, and PF3) were characterized as Pseudomonas plecoglossicida, Pseudomonas aeruginosa, and P. aeruginosa, respectively. A consortium and all isolates could utilize PF as a sole carbon source with PF removal of more than 90% via a hydrolysis process. The bacterial growth and PF degradation rates followed the first-order kinetic reaction with the rates of 0.4 to 2.7/h and 0.15 to 1.96/h, respectively. Additional carbon supplement deteriorated PF biodegradation. The enriched cultures were also capable for degrading chlorpyrifos and dicrotophos pesticides (33-73% removal). The results indicated that the consortium and isolates are efficient for PF and other OPP degradation and have potential for PF remediation.

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“…Additionally, 2,4-ditert-butyl phenol (2,4-DTBP) during the degradation test was found. It was known that 2,4-DTBP could be used for pesticide production (Schwetlick et al 1991).…”

Section: Pf Intermediate Metabolite Detectionmentioning

confidence: 99%

Profenofos insecticide degradation by novel microbial consortium and isolates enriched from contaminated chili farm soil

Siripattanakul‐Ratpukdi

Vangnai

Sangthean

et al. 2014

Environ Sci Pollut Res

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“…In terms of their functionality for effective polymer stabilization, better results were obtained by the use of combined systems of hydrolysable and non-hydrolysable phosphates [6]. Hindered phenols released during hydrolysis form synergistic mixtures with either the parent phosphite, or its intermediate hydrolysis products and these contribute to the overall stabilization performance through chain terminating mechanisms [6,7]. Hydrolysis products were also found to be active processing stabilizers themselves by preventing discoloration and enhancing melt stabilization of the polymer [8].…”

Section: Introductionmentioning

confidence: 90%

Atmospheric pressure photoionization mass spectrometry as a tool for the investigation of the hydrolysis reaction mechanisms of phosphite antioxidants

Papanastasiou

McMahon

Allen

et al. 2008

International Journal of Mass Spectrometry

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“…In addition to hydrolysis, oxidation of the phosphorus compounds by hydroperoxides (equation 1) and peroxyl radicals (equation 2 ) takes place in the course of reaction giving the corresponding phosph(on)ates (10). The ratio of oxidation to hydrolysis depends on the oxidazibility of the particular substrate and on the reaction conditions (temperature).…”

Section: VIIImentioning

confidence: 99%

Organophosphorus antioxidants action mechanisms and new trends

Schwetlick

Habicher

1995

Angew. Makromol. Chem.

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Phosphite and phosphonite esters can act as antioxidants by three basic mechanisms depending on their structure. the nature of the substrate to be stabilized and the reaction conditions. AN phosph(0n)ites are hydroperoxidedecomposing secondary antioxidants. Their efficiency in hydroperoxide reduction decreases in the order phosphonites > alkylphosphites > arylphosphites > hindered arylphosphites. Five-membered cyclic phosphites are capable of decomposing hydroperoxides catalytically due to the formation of acidic hydrogen phosphates by hydrolysis and peroxidolysis in the course of reaction. Hindered aryl phosphites can act as chain-breaking primary antioxidants being substituted by alkoryl radicals and releasing hindered aryloryl radicals which terminate the radical chain oxidation. At ambient temperatures, the chain-breaking antioxidant activity of a v l phosphites is lower than that of hindered phenols. because the rate of their reaction with peroxyl radicals and their stoichiometric inhibition factors are lower than those of phenols. In oxidizing media at medium temperatures, however, hydrolysis of aryl phosph(0n)ites takes place giving hydrogen phosph(0n)ites and phenols which are effective chain-breaking antioxidants, 2,2,6,6-TetramethyI-and 1,2,2,6,6-Pentamethylpiperidinyl phosphites and phosphonites (HAS phosph(on)ites) surpass many common phosphites, phenols and HALS compounds as stabiiilizers in the thermo-and photo-oxidation ofpolymers. Their superior eflciency is probably due to an intramolecular synergistic action of the HALS and the phosph(on)i te moieties of their molecules.

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Organophosphorus antioxidants: Part X—Mechanism of antioxidant action of aryl phosphites and phosphonites at higher temperatures

Cited by 52 publications

References 7 publications

Profenofos insecticide degradation by novel microbial consortium and isolates enriched from contaminated chili farm soil

Profenofos insecticide degradation by novel microbial consortium and isolates enriched from contaminated chili farm soil

Atmospheric pressure photoionization mass spectrometry as a tool for the investigation of the hydrolysis reaction mechanisms of phosphite antioxidants

Organophosphorus antioxidants action mechanisms and new trends

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