Enhanced photoproduction of hydrogen peroxide by humic substances in the presence of phenol electron donors

Environmental Science and Technology

Volumn 48, Issue 21, 2014, Pages 12679-12688

  Zhang, Yi ^a   Simon, Kelli A ^a   Andrew, Andrea A ^a   Del Vecchio, Rossana ^b   Blough, Neil V ^a  

^a University of Maryland   (United States)

^b UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; HYDROGEN PEROXIDE; KETONES; OXIDATION; OXYGEN; PEROXIDES; THERMOMECHANICAL PULPING PROCESS;

2 ,4 ,6-TRIMETHYLPHENOL; AROMATIC KETONES; BOROHYDRIDE REDUCTIONS; ENHANCEMENT FACTOR; EXCITED TRIPLET STATE; HUMIC SUBSTANCES; PHOTOPRODUCTIONS; SECONDARY REACTIONS;

PHENOLS;

BENZOPHENONE; DISSOLVED ORGANIC MATTER; HYDROGEN PEROXIDE; KETONE; OXYGEN; PHENOL DERIVATIVE; QUINONE DERIVATIVE; RADICAL; SODIUM BOROHYDRIDE; SUPEROXIDE; 2,4,6-TRIMETHYLPHENOL; CRESOL; HUMIC SUBSTANCE; PHENOL;

CONCENTRATION (COMPOSITION); ELECTRON; ENZYME ACTIVITY; HUMIC SUBSTANCE; HYDROGEN PEROXIDE; ORGANIC COMPOUND; PHENOL;

ARTICLE; CHEMOLUMINESCENCE; ELECTRON; ELECTRON DONOR; HUMIC SUBSTANCE; OLIGOMERIZATION; OXIDATION REDUCTION POTENTIAL; PHOTODYNAMICS; PHOTOPRODUCTION; QUANTUM YIELD; STOICHIOMETRY; ANALYSIS; CHEMISTRY; KINETICS; LIGHT; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; QUANTUM THEORY; REGRESSION ANALYSIS; RIVER;

CRESOLS; ELECTRONS; HUMIC SUBSTANCES; HYDROGEN PEROXIDE; KETONES; KINETICS; LEAST-SQUARES ANALYSIS; LIGHT; OXIDATION-REDUCTION; OXYGEN; PHENOL; PHOTOCHEMICAL PROCESSES; QUANTUM THEORY; RIVERS;

EID: 84908592675     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es5035798     Document Type: Article

References (59)

1. Van Baalen, C.; Marler, J. E. Occurrence of hydrogen peroxide in sea water Nature 1966, 211 (5052) 951-951
2. Baxter, R. M.; Carey, J. H. Evidence for photochemical generation of superoxide ion in humic waters Nature 1983, 306 (5943) 575-576
3. Kok, G. L. Measurements of hydrogen peroxide in rainwater Atmos. Environ. (1967) 1980, 14 (6) 653-656
4. Cooper, W. J.; Zika, R. G. Photochemical formation of hydrogen peroxide in surface and ground waters exposed to sunlight Science 1983, 220 (4598) 711-712
5. Draper, W. M.; Crosby, D. G. The photochemical generation of hydrogen peroxide in natural waters Arch. Environ. Contam. Toxicol. 1983, 12 (1) 121-126
6. Cooper, W. J.; Zika, R. G.; Petasne, R. G.; Plane, J. M. Photochemical formation of hydrogen peroxide in natural waters exposed to sunlight Environ. Sci. Technol. 1988, 22, 1156-60
7. Blough, N. V.; Zepp, R., Reactive oxygen species innatural waters. In In Active oxygen in Chemistry, Foote, C. S.; Valentine, J. S.; Greenberg, A.; Liebman, J. F., Eds.; Ed. Champman and Hall: New York, 1995; Vol. New York pp 280-333.
8. Cooper, W. J.; Zika, R. G.; Petasne, R. G.; Fischer, A. M. Sunlight-induced photochemistry of humic substances in natural waters: Major reactive species Adv. Chem. Ser. 1989, 219, 333-62
9. OSullivan, D. W.; Neale, P. J.; Coffin, R. B.; Boyd, T. J.; Osburn, C. L. Photochemical production of hydrogen peroxide and methylhydroperoxide in coastal waters Mar. Chem. 2005, 97 (1-2) 14-33
10. Goldstone, J. V.; Voelker, B. M. Chemistry of superoxide radical in seawater: CDOM associated sink of superoxide in coastal waters Environ. Sci. Technol. 2000, 34 (6) 1043-1048
11. Garg, S.; Rose, A. L.; Waite, T. D. Photochemical production of superoxide and hydrogen peroxide from natural organic matter Geochim. Cosmochim. Acta 2011, 75 (15) 4310-4320
12. Sharpless, C. M.; Blough, N. V. The importance of charge-transfer interactions in determining chromophoric dissolved organic matter (CDOM) optical and photochemical properties Environ. Sci.: Process. Impacts 2014, 16, 654-671
13. Kieber, D. J.; Miller, G. W.; Neale, P. J.; Mopper, K. Wavelength and temperature-dependent apparent quantum yields for photochemical formation of hydrogen peroxide in seawater Environ. Sci.: Process. Impacts 2014, 16 (4) 777-791
14. Powers, L. C.; Miller, W. L. Blending remote sensing data products to estimate photochemical production of hydrogen peroxide and superoxide in the surface ocean Environ. Sci.: Process. Impacts 2014, 16 (4) 792-806
15. Heller, M. I.; Croot, P. L. Superoxide decay as a probe for speciation changes during dust dissolution in Tropical Atlantic surface waters near Cape Verde Mar. Chem. 2011, 126, 37-55
16. Moffett, J. W.; Zika, R. G. Reaction kinetics of hydrogen peroxide with copper and iron in seawater Environ. Sci. Technol. 1987, 21, 804-10
17. Vermilyea, A. W.; Voelker, B. M. Photo-fenton reaction at near neutral pH Environ. Sci. Technol. 2009, 43 (18) 6927-6933
18. Rose, A. L.; Waite, T. D. Role of superoxide in the photochemical reduction of iron in seawater Geochim. Cosmochim. Acta 2006, 70 (15) 3869-3882
19. Aguer, J.-P.; Tetegan, D.; Richard, C. Humic substances mediated phototransformation of 2,4,6-trimethylphenol: A catalytic reaction Photochem. Photobiol. Sci. 2005, 4 (6) 451-453
20. Zhan, M.; Yang, X.; Xian, Q.; Kong, L. Photosensitized degradation of bisphenol A involving reactive oxygen species in the presence of humic substances Chemosphere 2006, 63 (3) 378-386
21. Wenk, J.; von Gunten, U.; Canonica, S. Effect of dissolved organic matter on the transformation of contaminants induced by excited triplet states and the hydroxyl radical Environ. Sci. Technol. 2011, 45 (4) 1334-1340
22. -) decay in the Eastern Tropical North Atlantic Environ. Sci. Technol. 2013, 47 (18) 10249-10256
23. Petasne, R. G.; Zika, R. G. Fate of superoxide in coastal sea water Nature 1987, 325 (6104) 516-518
24. Heller, M. I.; Croot, P. L. Superoxide decay kinetics in the Southern Ocean Environ. Sci. Technol. 2010, 44, 191-196
25. Micinski, E.; Ball, L. A.; Zafiriou, O. C. Photochemical oxygen activation: Superoxide radical detection and production rates in the Eastern Caribbean J. Geophys. Res. 1993, 98, 2299-2306
26. Cory, R. M.; McNeill, K.; Cotner, J. P.; Amado, A.; Purcell, J. M.; Marshall, A. G. Singlet oxygen in the coupled photochemical and biochemical oxidation of dissolved organic matter Environ. Sci. Technol. 2010, 44 (10) 3683-3689
27. Wang, W.; Zafiriou, O. C.; Chan, I. Y.; Zepp, R. G.; Blough, N. V. Production of hydrated electrons from photoionization of dissolved organic matter in natural waters Environ. Sci. Technol. 2007, 41 (5) 1601-1607
28. Zepp, R. G.; Braun, A. M.; Hoigne, J.; Leenheer, J. A. Photoproduction of hydrated electrons from natural organic solutes in aquatic environments Environ. Sci. Technol. 1987, 21, 485-90
29. Thomas-Smith, T. E.; Blough, N. V. Photoproduction of hydrated electron from constituents of natural waters Environ. Sci. Technol. 2001, 35 (13) 2721-2726
30. Zhang, Y.; Del Vecchio, R.; Blough, N. V. Investigating the mechanism of hydrogen peroxide photoproduction by humic substances Environ. Sci. Technol. 2012, 46 (21) 11836-11843
31. Canonica, S.; Jans, U.; Stemmler, K.; Hoigne, J. Transformation kinetics of phenols in water: Photosensitization by dissolved natural organic material and aromatic ketones Environ. Sci. Technol. 1995, 29 (7) 1822-1831
32. Golanoski, K. S.; Fang, S.; Del Vecchio, R.; Blough, N. V. Investigating the mechanism of phenol photooxidation by humic substances Environ. Sci. Technol. 2012, 46 (7) 3912-3920
33. Halladja, S.; ter Halle, A.; Aguer, J.-P.; Boulkamh, A.; Richard, C. Inhibition of humic substances mediated photooxygenation of furfuryl alcohol by 2,4,6-trimethylphenol. evidence for reactivity of the phenol with humic triplet excited states Environ. Sci. Technol. 2007, 41 (17) 6066-6073
34. Canonica, S.; Freiburghaus, M. Electron-rich phenols for probing the photochemical reactivity of freshwaters Environ. Sci. Technol. 2001, 35 (4) 690-695
35. Canonica, S.; Hellrung, B.; Müller, P.; Wirz, J. Aqueous oxidation of phenylurea herbicides by triplet aromatic ketones Environ. Sci. Technol. 2006, 40 (21) 6636-6641
36. Canonica, S.; Hellrung, B.; Wirz, J. Oxidation of phenols by triplet aromatic ketones in aqueous solution J. Phys. Chem. A 2000, 104 (6) 1226-1232
37. Canonica, S. Oxidation of aquatic organic contaminants induced by excited triplet states Chimia 2007, 61 (10) 641-644
38. Anastasio, C.; Faust, B. C.; Rao, C. J. Aromatic carbonyl compounds as aqueous-phase photochemical sources of hydrogen peroxide in acidic sulfate aerosols, fogs, and clouds. 1. Non-phenolic methoxybenzaldehydes and methoxyacetophenones with reductants (phenols) Environ. Sci. Technol. 1997, 31 (1) 218-232
39. Smith, J. D.; Sio, V.; Yu, L.; Zhang, Q.; Anastasio, C. Secondary Organic Aerosol Production from Aqueous Reactions of Atmospheric Phenols with an Organic Triplet Excited State. Environ. Sci. Technol. 2013, 48 (2) 1049-1057
40. De Laurentiis, E.; Maurino, V.; Minero, C.; Vione, D.; Mailhot, G.; Brigante, M. Could triplet-sensitised transformation of phenolic compounds represent a source of fulvic-like substances in natural waters? Chemosphere 2013, 90 (2) 881-884
41. De Laurentiis, E.; Minella, M.; Maurino, V.; Minero, C.; Brigante, M.; Mailhot, G.; Vione, D. Photochemical production of organic matter triplet states in water samples from mountain lakes, located below or above the tree line Chemosphere 2012, 88 (10) 1208-1213
42. Boyle, E. S.; Guerriero, N.; Thiallet, A.; Del Vecchio, R.; Blough, N. V. Optical properties of humic substances and CDOM: Relation to structure Environ. Sci. Technol. 2009, 43 (7) 2262-2268
43. Kujawinski, E. B.; Del Vecchio, R.; Blough, N. V.; Klein, G. C.; Marshall, A. G. Probing molecular-level transformations of dissolved organic matter: Insights on photochemical degradation and protozoan modification of DOM from electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry Mar. Chem. 2004, 92 (1-4) 23-37
44. Ma, J. H.; Del Vecchio, R.; Golanoski, K. S.; Boyle, E. S.; Blough, N. V. Optical properties of humic substances and CDOM: Effects of borohydride reduction Environ. Sci. Technol. 2010, 44 (14) 5395-5402
45. Baluha, D. R.; Blough, N. V.; Del Vecchio, R. Selective mass labeling for linking the optical properties of chromophoric dissolved organic matter to structure and composition via ultrahigh resolution electrospray ionization mass spectrometry Environ. Sci. Technol. 2013, 47 (17) 9891-9897
46. Aeschbacher, M.; Sander, M.; Schwarzenbach, R. P. Novel electrochemical approach to assess the redox properties of humic substances Environ. Sci. Technol. 2010, 44, 87-93
47. Miller, G. W.; Morgan, C. A.; Kieber, D. J.; King, D. W.; Snow, J. A.; Heikes, B. G.; Mopper, K.; Kiddle, J. J. Hydrogen peroxide method intercomparision study in seawater Mar. Chem. 2005, 97 (1-2) 4-13
48. 2 in natural waters using acridinium ester chemiluminescence: Method development and optimization using a kinetic model Anal. Chem. 2007, 79 (11) 4169-4176
49. 4 titration Anal. Chem. 1994, 66, 2921-5
50. 4 reduction on singlet oxygen quantum yields: Implications for DOM photophysics Environ. Sci. Technol. 2012, 46, 4466-4473
51. dAlessandro, N.; Bianchi, G.; Fang, X.; Jin, F.; Schuchmann, H.-P.; von Sonntag, C. Reaction of superoxide with phenoxyl-type radicals J. Chem. Soc., Perkin Trans. 2 2000, 9) 1862-1867
52. - Radicals in aqueous solution J. Phys. Chem. Ref. Data 1985, 14 (4) 1041-1100
53. Lardinois, O. M. Reactions of bovine liver catalase with superoxide radicals and hydrogen peroxide Free Rad. Res. 1995, 22 (3) 251-274
54. Kozmér, Z.; Arany, E.; Alapi, T.; Takács, E.; Wojnárovits, L.; Dombi, A. Determination of the rate constant of hydroperoxyl radical reaction with phenol Radiat. Phys. Chem. 2014, 102 (0) 135-138
55. René, A.; Abasq, M.-L.; Hauchard, D.; Hapiot, P. How do phenolic compounds react toward superoxide ion? A simple electrochemical method for evaluating antioxidant capacity Anal. Chem. 2010, 82 (20) 8703-8710
56. Perri, M. J.; Seitzinger, S.; Turpin, B. J. Secondary organic aerosol production from aqueous photooxidation of glycolaldehyde: Laboratory experiments Atmos. Environ. 2009, 43 (8) 1487-1497
57. Canonica, S.; Hoigné, J. Enhanced oxidation of methoxy phenols at micromolar concentration photosensitized by dissolved natural organic material Chemosphere 1995, 30 (12) 2365-2374
58. Lind, J.; Shen, X.; Eriksen, T. E.; Merenyi, G. The one-electron reduction potential of 4-substituted phenoxyl radicals in water J. Am. Chem. Soc. 1990, 112 (2) 479-482
59. Jonsson, M.; Lind, J.; Reitberger, T.; Eriksen, T. E.; Merenyi, G. Free radical combination reactions involving phenoxyl radicals J. Phys. Chem. 1993, 97 (31) 8229-8233