Impact of halides on the photoproduction of reactive intermediates from organic matter

Environmental Science and Technology

Volumn 47, Issue 24, 2013, Pages 13949-13956

  Glover, Caitlin M ^a   Rosario Ortiz, Fernando L ^a  

^a University of Colorado at Boulder   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOLVED ORGANIC MATTERS; EXCITED SINGLET STATE; FLUORESCENCE QUANTUM YIELD; FORMATION POTENTIAL; INTER-SYSTEM CROSSINGS; REACTIVE INTERMEDIATE; STEADY STATE CONCENTRATION; TRACE ORGANIC CONTAMINANTS;

BIOLOGICAL MATERIALS; CHLORINE COMPOUNDS; FLUORESCENCE; QUANTUM YIELD; QUENCHING; REACTION INTERMEDIATES;

EXCITED STATES;

AROMATIC HYDROCARBON; BENZENE; BROMIDE; CARBONYL DERIVATIVE; CHLORIDE; DISSOLVED ORGANIC MATTER; DISSOLVED OXYGEN; HALIDE; OXYGEN;

CONCENTRATION (COMPOSITION); DISSOLVED ORGANIC MATTER; HALIDE; HYDROXYL RADICAL; ORGANIC POLLUTANT; OXYGEN; PATHOGEN; WASTEWATER;

ARTICLE; FLUORESCENCE; HYDROXYLATION; QUANTUM YIELD; SUN EXPOSURE; SUNLIGHT; WASTE WATER;

BROMIDES; CHLORIDES; FLUORESCENCE; HALOGENS; HYDROXYL RADICAL; KINETICS; ORGANIC CHEMICALS; SINGLET OXYGEN; SPECTRUM ANALYSIS; SUNLIGHT;

EID: 84890737901     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es4026886     Document Type: Article

References (59)

1. Richardson, S. D.; Ternes, T. A. Water Analysis: Emerging Contaminants and Current Issues Anal. Chem. 2011, 83, 4614-4648
2. Blough, N. V.; Zepp, R. G. Reactive oxygen species in natural waters. In Active oxygen in chemistry; Foote, C. S.; Valentine, J. S.; Greenberg, A.; Liebman, J. F., Eds.; Springer, 1995; pp 280-333.
3. Schwarzenbach, R. P.; Gschswend, P. M.; Imboden, D. M. Environmental Organic Chemistry, 2 nd ed.; John Wiley & Sons, Inc., 2002.
4. Zepp, R. G.; Schlotzhauer, P. F.; Sink, R. M. Photosensitized transformations involving electronic energy transfer in natural waters: role of humic substances Environ. Sci. Technol. 1985, 19, 74-81
5. Canonica, S.; Hellrung, B.; Müller, P.; Wirz, J. Aqueous oxidation of phenylurea herbicides by triplet aromatic ketones Environ. Sci. Technol. 2006, 40, 6636-6641
6. Canonica, S.; Hellrung, B.; Wirz, J. Oxidation of Phenols by Triplet Aromatic Ketones in Aqueous Solution J. Phys. Chem. A 2000, 104, 1226-1232
7. 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, 1822-1831
8. Wayne, C. E.; Wayne, R. P. Photochemistry; Oxford University Press, 1996.
9. Hassett, J. P. Enhanced: Dissolved Natural Organic Matter as a Microreactor Science 2006, 311, 1723-1724
10. Canonica, S.; Freiburghaus, M. Electron-Rich Phenols for Probing the Photochemical Reactivity of Freshwaters Environ. Sci. Technol. 2001, 35, 690-695
11. Zepp, R. G.; Wolfe, N. L.; Baughman, G. L.; Hollis, R. C. Singlet oxygen in natural waters Nature 1977, 267, 421-423
12. Haag, W. R.; Hoigne, J.; Gassman, E.; Braun, A. M. Singlet oxygen in surface waters-Part I: Furfuryl alcohol as a trapping agent Chemosphere 1984, 13, 631-640
13. Alegría, A. E.; Ferrer, A.; Sepúlveda, E. Photochemistry of Water-soluble Quinones. Production of a Water-derived Spin Adduct Photochem. Photobiol. 1997, 66, 436-442
14. Alegría, A. E.; Ferrer, A.; Santiago, G.; Sepulveda, E.; Flores, W. Photochemistry of water-soluble quinones. Production of the hydroxyl radical, singlet oxygen and the superoxide io. J. Photochem. Photobiol. A: Chem. 1999, 127, 57-65
15. Vaughan, P. P.; Blough, N. V. Photochemical formation of hydroxyl radical by constituents of natural waters Environ. Sci. Technol. 1998, 32, 2947-2953
16. Pochon, A.; Vaughan, P. P.; Gan, D.; Vath, P.; Blough, N. V.; Falvey, D. E. Photochemical Oxidation of Water by 2-Methyl-1,4-benzoquinone: Evidence against the Formation of Free Hydroxyl Radical J. Phys. Chem. A 2002, 106, 2889-2894
17. Grebel, J.; Pignatello, J. J.; Mitch, W. A. Impact of halide ions on natural organic matter-sensitized photolysis of 17β-estradiol in saline waters Environ. Sci. Technol. 2012, 46, 120608155828001
18. Hem, J. D. Study and interpretation of the chemical characteristics of natural water; U.S. Geological Survey, 1985; Water supply paper 2254.
19. al Housari, F.; Vione, D.; Chiron, S.; Barbati, S. Reactive photoinduced species in estuarine waters. Characterization of hydroxyl radical, singlet oxygen and dissolved organic matter triplet state in natural oxidation processes Photochem. Photobiol. Sci. 2010, 9, 78
20. Grebel, J. E.; Pignatello, J. J.; Mitch, W. A. Effect of Halide Ions and Carbonates on Organic Contaminant Degradation by Hydroxyl Radical-Based Advanced Oxidation Processes in Saline Waters Environ. Sci. Technol. 2010, 44, 6822-6828
21. Liao, C.-H.; Kang, S.-F.; Wu, F.-A. Hydroxyl radical scavenging role of chloride and bicarbonate ions in the H2O2/UV Process Chemosphere 2001, 44, 1193-1200
22. Jammoul, A.; Dumas, S.; D'Anna, B.; George, C. Photoinduced oxidation of sea salt halides by aromatic ketones: a source of halogenated radicals Atmos. Chem. Phys 2009, 9, 4229-4237
23. Dorfman, L. M.; Taub, I. A.; Buhler, R. E. Pulse radiolysis studies. I Transient specta and reaction-rate constants in irradiated aqueous solutions of benzene J. Chem. Phys. 1962, 365-391
24. Grebel, J. E.; Pignatello, J. J.; Song, W.; Cooper, W. J.; Mitch, W. A. Impact of halides on the photobleaching of dissolved organic matter Mar. Chem. 2009, 115, 134-144
25. Parker, K. M.; Pignatello, J. J.; Mitch, W. A. Influence of ionic strength on triplet-state natural organic matter loss by energy transfer and electron transfer pathways Environ. Sci. Technol. 2013, 47, 10987-10994
26. Dong, M. M.; Rosario-Ortiz, F. L. Photochemical Formation of Hydroxyl Radical from Effluent Organic Matter Environ. Sci. Technol. 2012, 46, 3788-3794
27. Mostafa, S.; Rosario-Ortiz, F. L. Singlet oxygen formation from wastewater organic matter Environ. Sci. Technol. 2013, 47, 8179-8186
28. Canonica, S.; Kohn, T.; Mac, M.; Real, F. J.; Wirz, J.; von Gunten, U. Photosensitizer Method to Determine Rate Constants for the Reaction of Carbonate Radical with Organic Compounds Environ. Sci. Technol. 2005, 39, 9182-9188
29. Zhou, X.; Mopper, K. Determination of photochemically produced hydroxyl radicals in seawater and freshwater Mar. Chem. 1990, 30, 71-88
30. 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 Radical (OH/O-) in Aqueous Solution J. Phys. Chem. Ref. Data 1988, 17, 1-374
31. Murphy, K. R.; Butler, K. D.; Spencer, R. G. M.; Stedmon, C. A.; Boehme, J. R.; Aiken, G. R. Measurement of Dissolved Organic Matter Fluorescence in Aquatic Environments: An Interlaboratory Comparison Environ. Sci. Technol. 2010, 44, 9405-9412
32. Sharpless, C. M. Lifetimes of Triplet Dissolved Natural Organic Matter (DOM) and the Effect of NaBH 4Reduction on Singlet Oxygen Quantum Yields: Implications for DOM Photophysics Environ. Sci. Technol. 2012, 46, 4466-4473
33. Tratnyek, P. G.; Hoigne, J. Photo-oxidation of 2, 4, 6-trimethylphenol in aqueous laboratory solutions and natural waters: kinetics of reaction with singlet oxygen J. Photochem. Photobiol. A: Chem. 1994, 84, 153-160
34. Aguer, J.-P.; Tétégan, D.; Richard, C. Humic substances mediated phototransformation of 2,4,6-trimethylphenol: a catalytic reaction Photochem. Photobiol. Sci. 2005, 4, 451
35. Agilent Technologies Searchable Chromatography Library. Agilent Technologies. http://www.chem.agilent.com/en-US/Search/Library/Pages/ ChromatogramSearch.aspx.
36. Fletcher, A. N. Quinine sulfate as a fluorescence quantum yield standard Photochem. Photobiol. 1969, 9, 439-444
37. Geddes, C. D. Optical halide sensing using fluorescence quenching: theory, simulations and applications-a review Measure. Sci. Technol. 2001, 12, R53
38. Del Vecchio, R.; Blough, N. V. On the Origin of the Optical Properties of Humic Substances Environ. Sci. Technol. 2004, 38, 3885-3891
39. Vodacek, A.; Green, S. A.; Blough, N. V. An experimental model of the solar-stimulated fluorescence of chromophoric dissolved organic matter Limnol. Oceanogr. 1994, 39
40. Ma, J.; 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, 5395-5402
41. IHSS Database. Internation Humic Substances Society. http://www. humicsubstances.org/.
42. Peterson, B. M.; McNally, A. M.; Cory, R. M.; Thoemke, J. D.; Cotner, J. B.; McNeill, K. Spatial and Temporal Distribution of Singlet Oxygen in Lake Superior Environ. Sci. Technol. 2012, 46, 7222-7229
43. Dalrymple, R. M.; Carfagno, A. K.; Sharpless, C. M. Correlations between Dissolved Organic Matter Optical Properties and Quantum Yields of Singlet Oxygen and Hydrogen Peroxide Environ. Sci. Technol. 2010, 44, 5824-5829
44. Boehme, J. R.; Coble, P. G. Characterization of Colored Dissolved Organic Matter Using High-Energy Laser Fragmentation Environ. Sci. Technol. 2000, 34, 3283-3290
45. Whitehead, R. F.; de Mora, S.; Demers, S.; Gosselin, M.; Monfort, P.; Behzad, M. Interactions of Ultraviolet-B Radiation, Mixing, and Biological Activity on Photobleaching of Natural Chromophoric Dissolved Organic Matter: A Mesocosm Study Limnol. Oceanogr. 2000, 45, 278-291
46. Twardowski, M. S. Photobleaching of aquatic dissolved materials: Absorption removal, spectral alteration, and their interrelationship J. Geophys. Res. 2002, 107, 3091
47. de Bruyn, W. J.; Clark, C. D.; Pagel, L.; Takehara, C. Photochemical production of formaldehyde, acetaldehyde and acetone from chromophoric dissolved organic matter in coastal waters J. Photochem. Photobiol. A: Chem. 2011, 226, 16-22
48. Jammoul, A.; Dumas, S.; D'Anna, B.; George, C. Photoinduced oxidation of sea salt halides by aromatic ketones: a source of halogenated radicals Atmos. Chem. Phys. 2009, 9, 4229-4237
49. Clark, C. D.; Jimenez-Morais, J.; Jones, G., II; Zanardi-Lamardo, E.; Moore, C. A.; Zika, R. G. A time-resolved fluorescence study of dissolved organic matter in a riverine to marine transition zone Mar. Chem. 2002, 78, 1-15
50. Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Principles of Molecular Photochemistry: An Introduction; University Science Books: Sausalito, CA, 2009.
51. Bruccoleri, A.; Langford, C.; Arbour, C. Pulsed photo acoustic evaluation of intersystem crossing quantum yields in fulvic acid Env. Tech. 1990, 11, 169-172
52. Bruccoleri, A. G.; Pant, B. C.; Sharma, D. K.; Langford, C. H. Evaluation of Primary Photoproduct Quantum Yields in Fulvic Acid Environ. Sci. Technol. 1993, 889-894
53. Weishaar, J. L.; Aiken, G. R.; Bergamaschi, B. A.; Fram, M. S.; Fujii, R.; Mopper, K. Evaluation of Specific Ultraviolet Absorbance as an Indicator of the Chemical Composition and Reactivity of Dissolved Organic Carbon Environ. Sci. Technol. 2003, 37, 4702-4708
54. Page, S. E.; Arnold, W. A.; McNeill, K. Assessing the Contribution of Free Hydroxyl Radical in Organic Matter-Sensitized Photohydroxylation Reactions Environ. Sci. Technol. 2011, 45, 2818-2825
55. Bruccoleri, A.; Pant, B. C.; Sharma, D. K.; Langford, C. H.; Glover, C. Evaluation of Primary Photoproduct Quantum Yields in Fulvic Acid Environ. Sci. Technol. 1993, 27, 889-894
56. Matamoros, V.; Duhec, A.; Albaigés, J.; Bayona, J. M. Photodegradation of Carbamazepine, Ibuprofen, Ketoprofen and 17α-Ethinylestradiol in Fresh and Seawater Water Air Soil Pollut. 2008, 196, 161-168
57. Aranami, K.; Readman, J. W. Photolytic degradation of triclosan in freshwater and seawater Chemosphere 2007, 66, 1052-1056
58. Campbell, S.; David, M. D.; Woodward, L. A.; Li, Q. X. Persistence of carbofuran in marine sand and water Chemosphere 2004, 54, 1155-1161
59. Chiron, S.; Minero, C.; Vione, D. Photodegradation Processes of the Antiepileptic Drug Carbamazepine, Relevant To Estuarine Waters Environ. Sci. Technol. 2006, 40, 5977-5983