Dioxiranes Generated in Situ from Pyruvates and Oxone as Environmentally Friendly Oxidizing Agents for Disinfection

Wong, Man Leung; Chan, Tak Chung; Chan, Wai Yee; Chan, Wing Kei; Vrijmoed, L. L. P.; O’Toole, Desmond K.; Ming, Chi

doi:10.1021/es050688l

Cited by 12 publications

(4 citation statements)

References 28 publications

(35 reference statements)

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“…Peroxomonosulfate ion (HSO 5 − ), the anion of Caro’s acid (H 2 SO 5 ), is considered an inexpensive and environmentally friendly oxidant in several different applications. − In addition to high general reactivity, its main advantage over hydrogen peroxide is easier handling. It is available on a large scale in the form of a reasonably stable solid, which is commercially sold under the brand name Oxone (2KHSO 5 ·KHSO 4 ·K 2 SO 4 ).…”

Section: Introductionmentioning

confidence: 99%

One- Versus Two-Electron Oxidation with Peroxomonosulfate Ion: Reactions with Iron(II), Vanadium(IV), Halide Ions, and Photoreaction with Cerium(III)

et al. 2009

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The kinetics of the redox reactions of the peroxomonosulfate ion (HSO(5)(-)) with iron(II), vanadium(IV), cerium(III), chloride, bromide, and iodide ions were studied. Cerium(III) is only oxidized upon illumination by UV light and cerium(IV) is produced in a photoreaction with a quantum yield of 0.33 +/- 0.03. Iron(II) and vanadium(IV) are most probably oxidized through one-electron transfer producing sulfate ion radicals as intermediates. The halide ions are oxidized in a formally two-electron process, which most likely includes oxygen-atom transfer. Comparison with literature data suggests that the activation entropies might be used as indicators distinguishing between heterolytic and homolytic cleavage of the peroxo bond in the redox reactions of HSO(5)(-).

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Section: Introductionmentioning

confidence: 99%

One- Versus Two-Electron Oxidation with Peroxomonosulfate Ion: Reactions with Iron(II), Vanadium(IV), Halide Ions, and Photoreaction with Cerium(III)

et al. 2009

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“…2005). A dioxirane formed from methyl pyruvate and Oxone TM has also been recently reported to kill spores of B. cereus (Wong et al. 2006).…”

Section: Resultsmentioning

confidence: 99%

“…Previous work has shown that spores of Bacillus atrophaeus, a close relative of B. subtilis, are killed effectively by DMDO (Wallace et al 2005). A dioxirane formed from methyl pyruvate and Oxone TM has also been recently reported to kill spores of B. cereus (Wong et al 2006). Bacillus subtilis spores were also killed by DMDO ( Fig.…”

Section: Killing Of Spores Of Different Strains By Dmdomentioning

confidence: 86%

Mechanisms of killing of spores of Bacillus subtilis by dimethyldioxirane

et al. 2006

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Aims: To determine the mechanisms of Bacillus subtilis spore resistance to and killing by a novel sporicide, dimethyldioxirane (DMDO) that was generated in situ from acetone and potassium peroxymonosulfate at neutral pH. Methods and Results: Spores of B. subtilis were effectively killed by DMDO. Rates of killing by DMDO of spores lacking most DNA protective α/β‐type small, acid‐soluble spore proteins (α−β− spores) or the major DNA repair protein, RecA, were very similar to that of wild‐type spore killing. Survivors of wild‐type and α−β− spores treated with DMDO also exhibited no increase in mutations. Spores lacking much coat protein due either to mutation or chemical decoating were much more sensitive to DMDO than were wild‐type spores, but were more resistant than growing cells. Wild‐type spores killed with this reagent retained their large pool of dipicolinic acid (DPA), and the survivors of spores treated with DMDO were sensitized to wet heat. The DMDO‐killed spores germinated with nutrients, albeit more slowly than untreated spores, but germinated faster than untreated spores with dodecylamine. The killed spores were also germinated by very high pressures and by lysozyme treatment in hypertonic medium, but many of these spores lysed shortly after their germination, and none of these treatments were able to revive the DMDO‐killed spores. Conclusions: DMDO is an effective reagent for killing B. subtilis spores. The spore coat is a major factor in spore resistance to DMDO, which does not kill spores by DNA damage or by inactivating some component needed for spore germination. Rather, this reagent appears to kill spores by damaging the spore's inner membrane in some fashion. Significance and Impact of the Study: This work demonstrates that DMDO is an effective decontaminant for spores of Bacillus species that can work under mild conditions, and the killed spores cannot be revived. Evidence has also been obtained on the mechanisms of spore resistance to and killing by this reagent.

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“…The examination of reactions using Oxone compared to others could also be interesting. On one hand, it is considered to be environmentally friendly ,− , and on the other, the mass charge in relation to most substrates is large , because the molecular weight relative to the amount of oxygen it delivers is high.…”

Section: Discussionmentioning

confidence: 99%

Oxidation Numbers, Oxidants, and Redox Reactions: Variants of the Electrophilic Bromination of Alkenes and Variants of the Application of Oxone

et al. 2010

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Oxidation-state and donor−acceptor concepts are important areas in the chemical education. Student worksheets containing problems that emphasize oxidation numbers, redox reactions of organic compounds, and stoichiometric reaction equations are presented. All of the examples are incorporated under one unifying topic: the production of vicinal dibromides. Recent synthetic approaches use redox systems to generate bromine in situ to minimize hazards associated with molecular bromine. They illustrate how a range of oxidants can be applied to brominate the alkenes. The oxidant Oxone, also called Caroat or Curox, is examined. In addition to the solutions, the worksheets contain supporting information to help the students solve the problems. Thus, students are able to work independently with the material.

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Dioxiranes Generated in Situ from Pyruvates and Oxone as Environmentally Friendly Oxidizing Agents for Disinfection

Cited by 12 publications

References 28 publications

One- Versus Two-Electron Oxidation with Peroxomonosulfate Ion: Reactions with Iron(II), Vanadium(IV), Halide Ions, and Photoreaction with Cerium(III)

One- Versus Two-Electron Oxidation with Peroxomonosulfate Ion: Reactions with Iron(II), Vanadium(IV), Halide Ions, and Photoreaction with Cerium(III)

Mechanisms of killing of spores of Bacillus subtilis by dimethyldioxirane

Oxidation Numbers, Oxidants, and Redox Reactions: Variants of the Electrophilic Bromination of Alkenes and Variants of the Application of Oxone

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