Dioxiranes generated in situ from pyruvates and oxone as environmentally friendly oxidizing agents for disinfection

Environmental Science and Technology

Volumn 40, Issue 2, 2006, Pages 625-630

  Wong, Man Kin ^a   Chan, Tak Chung ^a   Chan, Wai Yee ^b   Chan, Wing Kei ^a   Vrijmoed, Lilian L P ^b   O'Toole, Desmond K ^b   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b CITY UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; BACTERIOLOGY; FUNGI; OXIDATION; PH EFFECTS;

BACTERIAL ENDOSPORES; METHYL PYRUVATE; OXIDIZING AGENTS; PENICILLIUM CORYLOPHILUM;

KETONES;

BICARBONATE; DIOXIRANE DERIVATIVE; KETONE DERIVATIVE; OXIDIZING AGENT; PYRUVIC ACID DERIVATIVE; SODIUM PEROXIDE; UNCLASSIFIED DRUG;

BACTERIA; BACTERIOLOGY; FUNGI; KETONES; OXIDATION; PH EFFECTS;

DISINFECTION;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; BACILLUS CEREUS; BACTERIAL ENDOSPORE; BACTERIUM; DISINFECTION; ENVIRONMENT; FUNGUS; NONHUMAN; OXIDATION; PENICILLIUM; PENICILLIUM CORYLOPHILUM; REACTION ANALYSIS; STAPHYLOCOCCUS AUREUS; TEMPERATURE DEPENDENCE;

DISINFECTANTS; EPOXY COMPOUNDS; OXIDANTS; PENICILLIUM; PYRUVATES; STAPHYLOCOCCUS AUREUS; SULFURIC ACIDS;

BACILLUS CEREUS; BACTERIA (MICROORGANISMS); FUNGI; PENICILLIUM; PENICILLIUM CORYLOPHILUM; STAPHYLOCOCCUS; STAPHYLOCOCCUS AUREUS;

EID: 31144457506     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es050688l     Document Type: Article

References (34)

1. Disinfection, Sterilization, and Preservation, 5th ed.; Block, S. S., Ed.; Lippincott Williams & Wilkins: Philadelphia, 2001.
2. Principles and Practice of Disinfection, Preservation and Sterilization, 3rd ed.; Russell, A. D., Hugo, W. B., Ayliffe, G. A. J., Eds.; Blackwell Science: Oxford, 1999.
3. Metcalf and Eddy, Inc. Wastewater Engineering: Treatment and Reuse, 4th ed.; McGraw-Hill: Boston, 2003.
4. McDonnell, G.; Russell, D. Antiseptics and disinfectants: Activity, action, and resistance. Clin. Microbiol. Rev. 1999, 12, 147-179.
5. White, G. C. Handbook of Chlorination and Alternative Disinfectants, 4th ed.; Wiley: New York, 1999.
6. Dychdala, G. R. In Disinfection, Sterilization, and Preservation, 5th ed.; Block, S. S., Ed.; Lippincott Williams & Wilkins: Philadelphia, 2001; Chapter 7, p 135.
7. Rutala, W. A.; Weber, D. J. Uses of inorganic hypochlorite (bleach) in health-care facilities. Clin. Microbiol. Rev. 1997, 10, 597-610.
8. McDonnell, G., Pretzer, D. In Disinfection, Sterilization, and Preservation, 5th ed.; Block, S. S., Ed.; Lippincott Williams & Wilkins: Philadelphia, 2001; Chapter 20, p 431.
9. Mills, A.; Hunte, S. L. An overview of semiconductor photocatalysis. J. Photochem. Photobiol. 1997, A108 (1), 1-35.
10. Ince, N. H.; Belen, R. Aqueous phase disinfection with power ultrasound: Process kinetics and effect of solid catalysts. Environ. Sci. Technol. 2001, 35, 1885-1888.
11. Ching, W. K.; Colussi, A. J.; Sun, H. J.; Nealson, K. H.; Hoffmann, M. R. Escherichia coli disinfection by electrohydraulic discharges. Environ. Sci. Technol. 2001, 35, 4139-4144 and references therein.
12. Manolache, S.; Somers, E. B.; Wong, A. C. L.; Shamamian, V.; Denes, F. Dense medium plasma environments: A new approach for the disinfection of water. Environ. Sci. Technol. 2001, 35, 3780-3785.
13. Decon DF-200 was developed by Sandia National Laboratories (http://www.sandia.gov).
14. Wagner, G. W.; Yang, Y. C. Rapid nucleophilic oxidative decontamination of chemical warfare agents. Ind. Eng. Chem. Res. 2002, 41, 1925-1928.
15. Raber, E.; McGuire, R. Oxidative decontamination of chemical and biological warfare agents using L-Gel. J. Hazard. Mater. 2002, 93, 339-352.
16. Adam, W.; Curci, R.; Edwards, J. O. Dioxiranes-A new class of powerful oxidants. Acc. Chem. Res. 1989, 22, 205-211.
17. Murray, R. W. Chemistry of dioxiranes. 12. Dioxiranes. Chem. Rev. 1989, 89, 1187-1201.
18. Curci, R.; Dinoi, A.; Rubino, M. F. Dioxirane oxidations-Taming the reactivity-selectivity principle. Pure Appl. Chem. 1995, 67, 811-822.
19. Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Dioxirane epoxidation of alkenes. Org. React. 2002, 61, 219-516.
20. Shi, Y. Organocatalytic asymmetric epoxidation of olefins by chiral ketones. Acc. Chem. Res. 2004, 37, 488-496.
21. Yang, D. Ketone-catalyzed asymmetric epoxidation reactions. Acc. Chem. Res. 2004, 37, 497-505.
22. Yang, D.; Wong, M-K.; Cheung, K.-K.; Chan, E. W. C.; Xie, Y. Studies on triepoxide analogues of triptolide. Tetrahedron Lett. 1997, 38, 6865-6868.
23. Chan, W.-K.; Yu, W.-Y.; Che, C-M.; Wong, M.-K. A cyclodextrin-modified ketoester for stereoselective epoxidation of alkenes. J. Org. Chem. 2003, 68, 6576-6582.
24. Yang, D.; Wong, M-K.; Wang, X.-C.; Tang, Y.-C. Regioselective intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ. J. Am. Chem. Soc. 1998, 120, 6611-6612.
25. Wong, M.-K.; Chung, N.-W.; He, L.; Yang, D. Substituent effects on regioselective intramolecular oxidation of unactivated C-H bonds: Stereoselective synthesis of substituted tetrahydropyrans. J. Am. Chem. Soc. 2003, 125, 158-162.
26. Wong, M.-K.; Chung, N.-W.; He, L.; Wang, X.-C.; Yan, Z.; Tang, Y.-C.; Yang, D. Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ. J. Org. Chem. 2003, 68, 6321-6328.
27. Yang, D.; Wong, M.-K.; Yan, Z. Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ. J. Org. Chem. 2000, 65, 4179-4184.
28. http://www.dupont.com/oxone/applications/index.html.
29. http://www.antechh.com/frameset.html.
30. Anipsitakis, G. P.; Dionysiou, D. D. Degradation of organic contaminants in water with sulfate radicals generated by the conjunction of peroxymonosulfate with cobalt. Environ. Sci. Technol. 2003, 37, 4790-4797.
31. Cheung H.-Y.; Cui J.-X.; Sun S.-Q. Real-time monitoring of Bacillus subtilis endospore components by attenuated total reflection Fourier transform infrared spectroscopy during germination. Microbiology 1999, 145, 1043-1048.
32. Facile, N.; Barbeau, B.; Prévost, M.; Koudjonou, B. Evaluating bacterial aerobic spores as a surrogate for Giardia and Cryptosporidium inactivation by ozone. Water Res. 2000, 34, 3238-3246.
33. 2 symmetric chiral ketone for catalytic asymmetric epoxidation of unfunctionalized olefins. J. Am. Chem. Soc. 1996, 118, 491-492.
34. Adam, W.; Saha-Moller, C. R.; Ganeshpure, P. A. Synthetic applications of nonmetal catalysts for homogeneous oxidations. Chem. Rev. 2001, 101, 3499-3548.