Activation of Peroxymonosulfate by Benzoquinone: A Novel Nonradical Oxidation Process

Environmental Science and Technology

Volumn 49, Issue 21, 2015, Pages 12941-12950

  Zhou, Yang ^a   Jiang, Jin ^a   Gao, Yuan ^a   Ma, Jun ^a   Pang, Su Yan ^b   Li, Juan ^a   Lu, Xue Ting ^b   Yuan, Li Peng ^b  

^a HARBIN INSTITUTE OF TECHNOLOGY   (China)

^b HARBIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE; ELECTROPHILE; HYDROXYL RADICAL; NATURAL ORGANIC MATTER; ORGANIC MATTER; OXYGEN; PEROXYMONOSULFATE; SINGLET OXYGEN; SULFAMETHOXAZOLE; SULFATE; UNCLASSIFIED DRUG; BENZOQUINONE DERIVATIVE; PEROXIDE; SULFATE RADICAL; WATER POLLUTANT;

BIODEGRADATION; CATALYSIS; OXIDATION; PH; REACTION KINETICS;

ARTICLE; CONTROLLED STUDY; DECOMPOSITION; DEGRADATION; ELECTRON SPIN RESONANCE; ELECTROPHILICITY; OXIDATION; PH; CATALYSIS; CHEMISTRY; KINETICS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION REDUCTION REACTION; PROCEDURES; WATER MANAGEMENT; WATER POLLUTANT;

BENZOQUINONES; CATALYSIS; CHROMATOGRAPHY, LIQUID; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN-ION CONCENTRATION; HYDROXYL RADICAL; KINETICS; MASS SPECTROMETRY; OXIDATION-REDUCTION; PEROXIDES; SULFAMETHOXAZOLE; SULFATES; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

EID: 84946782578     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/acs.est.5b03595     Document Type: Article

References (68)

1. 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 (20) 4790-4797 10.1021/es0263792
2. Ahmad, M.; Teel, A. L.; Watts, R. J. Mechanism of persulfate activation by phenols Environ. Sci. Technol. 2013, 47 (11) 5864-5871 10.1021/es400728c
3. Yuan, S. H.; Liao, P.; Alshawabkeh, A. N. Electrolytic manipulation of persulfate reactivity by iron electrodes for trichloroethylene degradation in groundwater Environ. Sci. Technol. 2014, 48 (1) 656-663 10.1021/es404535q
4. Neta, P.; Huie, R. E.; Ross, A. B. Rate constants for reactions of inorganic radicals in aqueous solution J. Phys. Chem. Ref. Data 1988, 17 (3) 1027-1284 10.1063/1.555808
5. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. Critical Review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (•OH/•O-) in aqueous solution J. Phys. Chem. Ref. Data 1988, 17 (2) 513-886 10.1063/1.555805
6. 2, and UV/PDS Environ. Sci. Technol. 2015, 49 (5) 3056-3066 10.1021/es504799n
7. Xie, P. C.; Ma, J.; Liu, W.; Zou, J.; Yue, S. Y.; Li, X. C.; Wiesner, M. R.; Fang, J. Y. Removal of 2-MIB and geosmin using UV/persulfate: Contributions of hydroxyl and sulfate radicals Water Res. 2015, 69, 223-233 10.1016/j.watres.2014.11.029
8. Lutze, H. V.; Bircher, S.; Rapp, I.; Kerlin, N.; Bakkour, R.; Geisler, M.; Von Sonntag, C.; Schmidt, T. C. Degradation of chlorotriazine pesticides by sulfate radicals and the influence of organic matter Environ. Sci. Technol. 2015, 49 (3) 1673-1680 10.1021/es503496u
9. Anipsitakis, G. P.; Dionysiou, D. D. Radical generation by the interaction of transition metals with common oxidants Environ. Sci. Technol. 2004, 38 (13) 3705-3712 10.1021/es035121o
10. Guan, Y. H.; Ma, J.; Li, X. C.; Fang, J. Y.; Chen, L. W. Influence of pH on the formation of sulfate and hydroxyl radicals in the UV/Peroxymonosulfate system Environ. Sci. Technol. 2011, 45 (21) 9308-9314 10.1021/es2017363
11. 4 spinel in water: Efficiency, stability, and mechanism Environ. Sci. Technol. 2013, 47 (6) 2784-2791 10.1021/es304721g
12. 2-based in situ chemical oxidation Environ. Sci. Technol. 2012, 46 (2) 1055-1062 10.1021/es203612d
13. Furman, O. S.; Teel, A. L.; Watts, R. J. Mechanism of base activation of persulfate Environ. Sci. Technol. 2010, 44 (16) 6423-6428 10.1021/es1013714
14. Fang, G. D.; Gao, J.; Dionysiou, D. D.; Liu, C.; Zhou, D. M. Activation of persulfate by quinones: Free radical reactions and implication for the degradation of PCBs Environ. Sci. Technol. 2013, 47 (9) 4605-4611 10.1021/es400262n
15. Zhu, B. Z.; Zhao, H. T.; Kalyanaraman, B.; Frei, B. Metal-independent production of hydroxyl radicals by halogenated quinones and hydrogen peroxide: An ESR spin trapping study Free Radical Biol. Med. 2002, 32 (5) 465-473 10.1016/S0891-5849(01)00824-3
16. Zhu, B. Z.; Kalyanaraman, B.; Jiang, G. B. Molecular mechanism for metal-independent production of hydroxyl radicals by hydrogen peroxide and halogenated quinones Proc. Natl. Acad. Sci. U. S. A. 2007, 104 (45) 17575-17578 10.1073/pnas.0704030104
17. Jakober, C. A.; Riddle, S. G.; Robert, M. A.; Destaillats, H.; Charles, M. J.; Green, P. G.; Kleeman, M. J. Quinone Emissions from Gasoline and Diesel Motor Vehicles Environ. Sci. Technol. 2007, 41 (13) 4548-4554 10.1021/es062967u
18. Aeschbacher, M.; Graf, C.; Schwarzenbach, R. P.; Sander, M. Antioxidant properties of humic substances Environ. Sci. Technol. 2012, 46 (9) 4916-4925 10.1021/es300039h
19. Siqueira, J. O.; Nair, M. G.; Hammerschmidt, R.; Safir, G. R.; Putnam, A. R. Significance of phenolic compounds in plant-soil-microbial systems Crit. Rev. Plant Sci. 1991, 10 (1) 63-121 10.1080/07352689109382307
20. Cory, R. M.; McKnight, D. M. Fluorescence spectroscopy reveals ubiquitous presence of oxidized and reduced quinones in dissolved organic matter Environ. Sci. Technol. 2005, 39 (21) 8142-8149 10.1021/es0506962
21. Doong, R.; Chiang, H. Transformation of carbon tetrachloride by thiol reductants in the presence of quinone compounds Environ. Sci. Technol. 2005, 39 (19) 7460-7468 10.1021/es047956k
22. Royer, R. A.; Burgos, W. D.; Fisher, A. S.; Unz, R. F.; Dempsey, B. A. Enhancement of biological reduction of hematite by electron shuttling and Fe(II) complexation Environ. Sci. Technol. 2002, 36 (9) 1939-1946 10.1021/es011139s
23. Duesterberg, C. K.; Waite, T. D. Kinetic modeling of the oxidation of p-hydroxybenzoic acid by Fentons reagent: Implications of the role of quinones in the redox cycling of iron Environ. Sci. Technol. 2007, 41 (11) 4103-4110 10.1021/es0628699
24. Chen, R. Z.; Pignatello, J. J. Role of quinone intermediates as electron shuttles in Fenton and photoassisted Fenton oxidations of aromatic compounds Environ. Sci. Technol. 1997, 31 (8) 2399-2406 10.1021/es9610646
25. Jiang, J.; Bauer, I.; Paul, A.; Kappler, A. Arsenic redox changes by microbially and chemically formed semiquinone radicals and hydroquinones in a humic substance model quinone Environ. Sci. Technol. 2009, 43 (10) 3639-3645 10.1021/es803112a
26. Dodd, M. C.; Huang, C. H. Transformation of the antibacterial agent sulfamethoxazole in reactions with chlorine: kinetics, mechanisms, and pathways Environ. Sci. Technol. 2004, 38 (21) 5607-5615 10.1021/es035225z
27. Ma, J.; Jiang, J.; Pang, S.; Guo, J. Adsorptive fractionation of humic acid at air-water interfaces Environ. Sci. Technol. 2007, 41 (14) 4959-4964 10.1021/es070238o
28. 18O-labeled linoleic acid hydroperoxide and monomol light emission measurements J. Am. Chem. Soc. 2003, 125 (20) 6172-6179 10.1021/ja029115o
29. Huber, M. M.; Korhonen, S.; Ternes, T. A.; von Gunten, U. Oxidation of pharmaceuticals during water treatment with chlorine dioxide Water Res. 2005, 39 (15) 3607-3617 10.1016/j.watres.2005.05.040
30. Wang, Y. R.; Le Roux, J.; Zhang, T.; Croué, J. Formation of brominated disinfection byproducts from natural organic matter isolates and model compounds in a sulfate radical-based oxidation process Environ. Sci. Technol. 2014, 48 (24) 14534-14542 10.1021/es503255j
31. Lee, J.; Mackeyev, Y.; Cho, M.; Li, D.; Kim, J. H.; Wilson, L. J.; Alvarez, P. J. J. Photochemical and antimicrobial properties of novel C60 derivatives in aqueous systems Environ. Sci. Technol. 2009, 43 (17) 6604-6610 10.1021/es901501k
32. Corey, E. J.; Taylor, W. C. A study of the peroxidation of organic compounds by externally generated singlet oxygen molecules J. Am. Chem. Soc. 1964, 86 (18) 3881-3882 10.1021/ja01072a062
33. Turro, N. J.; Chow, M. F. Mechanism of thermolysis of endoperoxides of aromatic compounds. Activation parameters, magnetic field, and magnetic isotope effects J. Am. Chem. Soc. 1981, 103 (24) 7218-7224 10.1021/ja00414a029
34. Pang, S. Y.; Jiang, J.; Gao, Y.; Zhou, Y.; Huangfu, X.; Liu, Y. Z.; Ma, J. Oxidation of flame retardant tetrabromobisphenol a by aqueous permanganate: Reaction kinetics, brominated products, and pathways Environ. Sci. Technol. 2014, 48 (1) 615-623 10.1021/es4041094
35. Gulkowska, A.; Sander, M.; Hollender, J.; Krauss, M. Covalent binding of sulfamethazine to natural and synthetic humic acids: Assessing laccase catalysis and covalent bond stability Environ. Sci. Technol. 2013, 47 (13) 6916-6924 10.1021/es3044592
36. Weber, E. J.; Spidle, D. L.; Thorn, K. A. Covalent binding of aniline to humic substances. 1. Kinetic studies Environ. Sci. Technol. 1996, 30 (9) 2755-2763 10.1021/es9509341
37. Evans, D. F.; Upton, M. W. Studies on singlet oxygen in aqueous solution. Part 3. The decomposition of peroxy-acids J. Chem. Soc., Dalton Trans. 1985, 6) 1151-1153 10.1039/dt9850001151
38. Ball, D. L.; Edwards, J. O. The kinetics and mechanism of the decomposition of Caros acid. I J. Am. Chem. Soc. 1956, 78 (6) 1125-1129 10.1021/ja01587a011
39. Rodgers, M. A. J. Solvent-induced deactivation of singlet oxygen: Additivity relationships in nonaromatic solvents J. Am. Chem. Soc. 1983, 105 (20) 6201-6205 10.1021/ja00358a001
40. Kellogg, E. W.; Fridovich, I. Superoxide, hydrogen peroxide, and singlet oxygen in lipid peroxidation by a xanthine oxidase system J. Biol. Chem. 1975, 250 (22) 8812-8817
41. Gsponer, H. E.; Previtali, C. M.; García, N. A. Kinetics of the photosensitized oxidation of polychlorophenols in alkaline aqueous solution Toxicol. Environ. Chem. 1987, 16 (1) 23-37 10.1080/02772248709357245
42. Moan, J.; Wold, E. Detection of singlet oxygen production by ESR Nature 1979, 279, 450-451 10.1038/279450a0
43. Li, H. R.; Wu, L. Z.; Tung, C. H. Reactions of singlet oxygen with olefins and sterically hindered amine in mixed surfactant vesicles J. Am. Chem. Soc. 2000, 122 (11) 2446-2451 10.1021/ja9917161
44. Song, B.; Wang, G. L.; Tan, M. Q.; Yuan, J. L. A Europium(III) complex as an efficient singlet oxygen luminescence probe J. Am. Chem. Soc. 2006, 128 (41) 13442-13450 10.1021/ja062990f
45. Lee, J.; Hong, S.; Mackeyev, Y.; Lee, C.; Chung, E.; Wilson, L. J.; Kim, J. H.; Alvarez, P. J. J. Photosensitized oxidation of emerging organic pollutants by tetrakis C60 Aminofullerene-Derivatized silica under visible light irradiation Environ. Sci. Technol. 2011, 45 (24) 10598-10604 10.1021/es2029944
46. 1 g)] production in the reaction of linoleic acid hydroperoxide with peroxynitrite J. Am. Chem. Soc. 2003, 125 (15) 4510-4517 10.1021/ja029262m
47. Montgomery, R. E. Catalysis of peroxymonosulfate reactions by ketones J. Am. Chem. Soc. 1974, 96 (25) 7820-7821 10.1021/ja00832a040
48. Edwards, J. O.; Pater, R. H.; Curclf, R.; Furia, F. D. On the formation and reactivity of dioxirane intermediates in the reaction of peroxoanions with organic substrates∗ Photochem. Photobiol. 1979, 30 (1) 63-70 10.1111/j.1751-1097.1979.tb07116.x
49. Lange, A.; Brauer, H. D. On the formation of dioxiranes and of singlet oxygen by the ketone-catalysed decomposition of Caros acid J. Chem. Soc., Perkin Trans. 2 1996, 5) 805-811 10.1039/p29960000805
50. Gallopo, A. R.; Edwards, J. O. Kinetics and mechanism of the oxidation of pyridine by Caros acid catalyzed by ketones J. Org. Chem. 1981, 46 (8) 1684-1688 10.1021/jo00321a032
51. Kruk, J.; Trebst, A. Plastoquinol as a singlet oxygen scavenger in photosystem II Biochim. Biophys. Acta, Bioenerg. 2008, 1777 (2) 154-162 10.1016/j.bbabio.2007.10.008
52. Krieger-Liszkay, A.; Fufezan, C.; Trebst, A. Singlet oxygen production in photosystem II and related protection mechanism Photosynth. Res. 2008, 98 (1-3) 551-564 10.1007/s11120-008-9349-3
53. Alegría, A. E.; Ferrer, A.; Santiago, G.; Sepúlveda, E.; Flores, W. Photochemistry of water-soluble quinones. Production of the hydroxyl radical, singlet oxygen and the superoxide ion J. Photochem. Photobiol., A 1999, 127 (1-3) 57-65 10.1016/S1010-6030(99)00138-0
54. Kurien, K. C.; Robins, P. A. Photolysis of aqueous solutions of p-benzoquinone: A spectrophotometric investigation J. Chem. Soc. B 1970, 855-859 10.1039/j29700000855
55. Zhao, Y. L.; Anichina, J.; Lu, X. F.; Bull, R. J.; Krasner, S. W.; Hrudey, S. E.; Li, X. F. Occurrence and formation of chloro- and bromo-benzoquinones during drinking water disinfection Water Res. 2012, 46 (14) 4351-4360 10.1016/j.watres.2012.05.032
56. Sarr, D. H.; Kazunga, C.; Charles, M. J.; Pavlovich, J. G.; Aitken, M. D. Decomposition of tetrachloro-1,4-benzoquinone (p-chloranil) in aqueous solution Environ. Sci. Technol. 1995, 29 (11) 2735-2740 10.1021/es00011a006
57. Imashiro, R.; Seki, M. A catalytic asymmetric synthesis of chiral glycidic acid derivatives through chiral Dioxirane-Mediated catalytic asymmetric epoxidation of cinnamic acid derivatives J. Org. Chem. 2004, 69 (12) 4216-4226 10.1021/jo049893u
58. Wu, X. Y.; She, X. G.; Shi, Y. Highly enantioselective epoxidation of α,β-unsaturated esters by chiral dioxirane J. Am. Chem. Soc. 2002, 124 (30) 8792-8793 10.1021/ja020478y
59. Adam, W.; Curci, R.; Edwards, J. O. Dioxiranes: A new class of powerful oxidants Acc. Chem. Res. 1989, 22 (6) 205-211 10.1021/ar00162a002
60. Kim, H.; Kim, W.; Mackeyev, Y.; Lee, G.; Kim, H. J.; Tachikawa, T.; Hong, S.; Lee, S.; Kim, J.; Wilson, L. J.; Majima, T.; Alvarez, P. J. J.; Choi, W.; Lee, J. Selective oxidative degradation of organic pollutants by singlet oxygen-mediated photosensitization: Tin porphyrin versus C60 aminofullerene systems Environ. Sci. Technol. 2012, 46 (17) 9606-9613 10.1021/es301775k
61. Fang, G. D.; Gao, J.; Liu, C.; Dionysiou, D. D.; Wang, Y.; Zhou, D. M. Key role of persistent free radicals in hydrogen peroxide activation by biochar: Implications to organic contaminant degradation Environ. Sci. Technol. 2014, 48 (3) 1902-1910 10.1021/es4048126
62. Lee, H.; Lee, H.; Jeong, J.; Lee, J.; Park, N.; Lee, C. Activation of persulfates by carbon nanotubes: Oxidation of organic compounds by nonradical mechanism Chem. Eng. J. 2015, 266 (0) 28-33 10.1016/j.cej.2014.12.065
63. Moor, K. J.; Snow, S. D.; Kim, J. H. Differential photoactivity of aqueous [C60] and [C70] fullerene aggregates Environ. Sci. Technol. 2015, 49 (10) 5990-5998 10.1021/acs.est.5b00100
64. Fujii, M.; Imaoka, A.; Yoshimura, C.; Waite, T. D. Effects of molecular composition of natural organic matter on ferric iron complexation at circumneutral pH Environ. Sci. Technol. 2014, 48 (8) 4414-4424 10.1021/es405496b
65. Kang, S.; Choi, W. Oxidative degradation of organic compounds using zero-valent iron in the presence of natural organic matter serving as an electron shuttle Environ. Sci. Technol. 2009, 43 (3) 878-883 10.1021/es801705f
66. Redman, A. D.; Macalady, D. L.; Ahmann, D. Natural organic matter affects arsenic speciation and sorption onto hematite Environ. Sci. Technol. 2002, 36 (13) 2889-2896 10.1021/es0112801
67. Cervantes, F. J.; Bok, F. A. M. D.; Duong-Dac, T.; Stams, A. J. M.; Lettinga, G.; Field, J. A. Reduction of humic substances by halorespiring, sulphate-reducing and methanogenic microorganisms Environ. Microbiol. 2002, 4 (1) 51-57 10.1046/j.1462-2920.2002.00258.x
68. Stevenson, F. J. Humus chemistry: genesis, composition, reactions; John Wiley & Sons Press: New York, 1994.