Phenolic antioxidants inhibit the triplet-induced transformation of anilines and sulfonamide antibiotics in aqueous solution

Environmental Science and Technology

Volumn 46, Issue 10, 2012, Pages 5455-5462

  Wenk, Jannis ^a,b   Canonica, Silvio ^a  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACCELERATED DEGRADATION; AROMATIC AMINES; DIAGNOSTIC TOOLS; DISSOLVED ORGANIC MATTERS; MICROMOLAR CONCENTRATION; PHENOLIC ANTIOXIDANT; PHOTO-INDUCED; SUBSTITUTED PHENOL; WATER CONTAMINANTS;

AMIDES; ANILINE; PHOTOSENSITIZERS; REACTION INTERMEDIATES; SOLUTIONS; SULFUR COMPOUNDS;

PHENOLS;

2 ACETONAPHTHONE; ANILINE; ANTIOXIDANT; DISSOLVED ORGANIC MATTER; PHENOL; PHOTOSENSITIZING AGENT; SULFONAMIDE; UNCLASSIFIED DRUG;

ANTIBIOTICS; ANTIOXIDANT; AQUEOUS SOLUTION; BIODEGRADATION; CONCENTRATION (COMPOSITION); DISSOLVED ORGANIC MATTER; INHIBITION; INHIBITOR; OXIDATION; PHENOLIC COMPOUND; TRANSFORMATION;

AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; DEGRADATION; IRRADIATION; OXIDATION; STEADY STATE;

ANILINE COMPOUNDS; ANTI-BACTERIAL AGENTS; ANTIOXIDANTS; ENVIRONMENT; KINETICS; LIGHT; MODELS, CHEMICAL; NAPHTHALENES; PHENOLS; SOLUTIONS; SULFADIAZINE; SULFAMETHOXAZOLE; SULFONAMIDES; WATER POLLUTANTS, CHEMICAL;

EID: 84861121093     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es300485u     Document Type: Article

References (45)

1. Canonica, S. Oxidation of aquatic organic contaminants induced by excited triplet states Chimia 2007, 61 (10) 641-644
2. Zepp, R. G.; Cline, D. M. Rates of direct photolysis in aquatic environment Environ. Sci. Technol. 1977, 11 (4) 359-366
3. Richard, C.; Canonica, S. Aquatic phototransformation of organic contaminants induced by coloured dissolved organic matter. In The Handbook of Environmental Chemistry; Hutzinger, O., Ed.; 2005; Vol. 2, Part M, pp 299-323.
4. Hoigné, J. Formulation and calibration of environmental reaction kinetics: Oxidations by aqueous photooxidants as an example. In Aquatic Chemical Kinetics: Reaction Rates of Processes in Natural Waters; Stumm, W., Ed.; Wiley-Interscience: New York, 1990; pp 43-70.
5. Brezonik, P. L.; Fulkerson-Brekken, J. Nitrate-induced photolysis in natural waters: Controls on concentrations of hydroxyl radical photo-intermediates by natural scavenging agents Environ. Sci. Technol. 1998, 32 (19) 3004-3010
6. Westerhoff, P.; Mezyk, S. P.; Cooper, W. J.; Minakata, D. Electron pulse radiolysis determination of hydroxyl radical rate constants with Suwannee River fulvic acid and other dissolved organic matter isolates Environ. Sci. Technol. 2007, 41 (13) 4640-4646
7. Larson, R. A.; Zepp, R. G. Reactivity of the carbonate radical with aniline derivatives Environ. Toxicol. Chem. 1988, 7 (4) 265-274
8. 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 (23) 9182-9188
9. Canonica, S.; Laubscher, H. U. Inhibitory effect of dissolved organic matter on triplet-induced oxidation of aquatic contaminants Photochem. Photobiol. Sci. 2008, 7 (5) 547-551
10. 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
11. Aeschbacher, M.; Sander, M.; Schwarzenbach, R. P. Novel electrochemical approach to assess the redox properties of humic substances Environ. Sci. Technol. 2010, 44 (1) 87-93
12. Aeschbacher, M.; Graf, C.; Schwarzenbach, R. P.; Sander, M. Antioxidant properties of humic substances. Environ. Sci. Technol. 2012, in press; DOI 10.1021/es300039h.
13. Peretyazhko, T.; Sposito, G. Reducing capacity of terrestrial humic acids Geoderma 2006, 137 (1-2) 140-146
14. Malcolm, R. L. The uniqueness of humic substances in each of soil, stream and marine environments Anal. Chim. Acta 1990, 232 (1) 19-30
15. Ritchie, J. D.; Perdue, E. M. Proton-binding study of standard and reference fulvic acids, humic acids, and natural organic matter Geochim. Cosmochim. Acta 2003, 67 (1) 85-96
16. Foti, M. C. Antioxidant properties of phenols J. Pharm. Pharmacol. 2007, 59 (12) 1673-1685
17. Shahidi, F.; Janitha, P. K.; Wanasundara, P. D. Phenolic antioxidants Crit. Rev. Food Sci. Nutr. 1992, 32 (1) 67-103
18. Kolpin, D. W.; Furlong, E. T.; Meyer, M. T.; Thurman, E. M.; Zaugg, S. D.; Barber, L. B.; Buxton, H. T. Pharmaceuticals, hormones, and other organic wastewater contaminants in US streams, 1999-2000: A national reconnaissance Environ. Sci. Technol. 2002, 36 (6) 1202-1211
19. Garcia-Galan, M. J.; Diaz-Cruz, M. S.; Barcelo, D. Determination of 19 sulfonamides in environmental water samples by automated on-line solid-phase extraction-liquid chromatography-tandem mass spectrometry (SPE-LC-MS/MS) Talanta 2010, 81 (1-2) 355-366
20. Boreen, A. L.; Arnold, W. A.; McNeill, K. Photochemical fate of sulfa drugs in the aquatic environment: Sulfa drugs containing five-membered heterocyclic groups Environ. Sci. Technol. 2004, 38 (14) 3933-3940
21. 2 extrusion photoproduct Environ. Sci. Technol. 2005, 39 (10) 3630-3638
22. Guerard, J. J.; Chin, Y. P.; Mash, H.; Hadad, C. M. Photochemical fate of sulfadimethoxine in aquaculture waters Environ. Sci. Technol. 2009, 43 (22) 8587-8592
23. Ryan, C. C.; Tan, D. T.; Arnold, W. A. Direct and indirect photolysis of sulfamethoxazole and trimethoprim in wastewater treatment plant effluent Water Res. 2011, 45 (3) 1280-1286
24. Kramer, J. B.; Canonica, S.; Hoigné, J.; Kaschig, J. Degradation of fluorescent whitening agents in sunlit natural waters Environ. Sci. Technol. 1996, 30 (7) 2227-2234
25. Halladja, S.; ter Halle, A.; Aguer, J. P.; Boulkamh, A.; Richard, C. Inhihition 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
26. Vione, D.; Khanra, S.; Das, R.; Minero, C.; Maurino, V.; Brigante, M.; Mailhot, G. Effect of dissolved organic compounds on the photodegradation of the herbicide MCPA in aqueous solution Water Res. 2010, 44 (20) 6053-6062
27. Richard, C.; Grabner, G. Mechanism of phototransformation of phenol and derivatives in aqueous solution. In The Handbook of Environmental Chemistry; Hutzinger, O., Ed.; Springer: Berlin, Germany, 1999; Vol. 2, Part L, pp 217-240.
28. Grabner, G.; Richard, C. Mechanisms of direct photolysis of biocides based on halogenated phenols and anilines. In The Handbook of Environmental Chemistry; Hutzinger, O., Ed.; Springer: Berlin, Germany, 2005; Vol. 2, Part M, pp 161-192.
29. Scully, F. E., Jr.; Hoigné, J. Rate constants for reactions of singlet oxygen with phenols and other compounds in water Chemosphere 1987, 16 (4) 681-694
30. Faust, B. C.; Hoigné, J. Sensitized photooxidation of phenols by fulvic acid and in natural waters Environ. Sci. Technol. 1987, 21 (10) 957-964
31. Tratnyek, P. G.; Hoigné, J. Photooxidation of 2,4,6- trimethylphenol in aqueous laboratory solutions and natural waters: kinetics of reaction with singlet oxygen J. Photochem. Photobiol., A 1994, 84 (2) 153-160
32. Canonica, S.; Jans, U.; Stemmler, K.; Hoigné, J. Transformation kinetics of phenols in water: Photosensitization by dissolved natural organic material and aromatic ketones Environ. Sci. Technol. 1995, 29 (7) 1822-1831
33. Canonica, S.; Freiburghaus, M. Electron-rich phenols for probing the photochemical reactivity of freshwaters Environ. Sci. Technol. 2001, 35 (4) 690-695
34. Richard, C.; Trubetskaya, O.; Trubetskoj, O.; Reznikova, O.; Afanas'eva, G.; Aguer, J. P.; Guyot, G. Key role of the low molecular size fraction of soil humic acids for fluorescence and photoinductive activity Environ. Sci. Technol. 2004, 38 (7) 2052-2057
35. 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
36. Loeff, I.; Rabani, J.; Treinin, A.; Linschitz, H. Charge-transfer and reactivity of nπ* and ππ* organic triplets, including anthraquinonesulfonates, in interactions with inorganic anions: A comparative study based on classical Marcus theory J. Am. Chem. Soc. 1993, 115 (20) 8933-8942
37. Jonsson, M.; Lind, J.; Eriksen, T. E.; Merényi, G. Redox and acidity properties of 4-substituted aniline radical cations in water J. Am. Chem. Soc. 1994, 116, 1423-1427
38. Li, C.; Hoffman, M. Z. One-electron redox potentials of phenols in aqueous solution J. Phys. Chem. B 1999, 103, 6653-6656
39. Qin, L.; Tripathi, G. N. R.; Schuler, R. H. Radiation chemical studies of the oxidation of aniline in aqueous solution Z. Naturforsch., A: Phys. Sci. 1985, 40 (10) 1026-1039
40. Jonsson, M.; Lind, J.; Reitberger, T.; Eriksen, T. E.; Merényi, G. Redox chemistry of substituted benzenes. The one-electron reduction potentials of methoxy-substituted benzene radical cations J. Phys. Chem. 1993, 97, 11278-11282
41. Merényi, G.; Lind, J. Anilinyl Radicals. In N-centered radicals; Alfassi, Z. B., Ed.; Wiley: 1998; p 715.
42. 2 J. Phys. Chem. 1986, 90 (6) 1193-1198
43. 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
44. Lucarini, M.; Pedulli, G. F. Free radical intermediates in the inhibition of the autoxidation reaction Chem. Soc. Rev. 2010, 39 (6) 2106-2119
45. Jonsson, M.; Lind, J.; Reitberger, T.; Eriksen, T. E.; Merényi, G. Free radical combination reactions involving phenoxyl radicals J. Phys. Chem. 1993, 97, 8229-8233