Modelling the photochemical fate of ibuprofen in surface waters

Water Research

Volumn 45, Issue 20, 2011, Pages 6725-6736

  Vione, Davide ^a   Maddigapu, Pratap Reddy ^a   De Laurentiis, Elisa ^a   Minella, Marco ^a   Pazzi, Marco ^a   Maurino, Valter ^a   Minero, Claudio ^a   Kouras, Sofia ^b   Richard, Claire ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Hydroxyl radical; Non steroidal anti inflammatory drug; PCCPs; Pharmaceuticals; Sensitised phototransformation; Singlet oxygen; Surface water photochemistry

Indexed keywords

AROMATIC COMPOUNDS; DRUG PRODUCTS; KETONES; PHOTOLYSIS; RATE CONSTANTS; SURFACE REACTIONS;

HYDROXYL RADICALS; NON-STEROIDAL ANTI-INFLAMMATORY DRUGS; PCCPS; PHOTOTRANSFORMATIONS; SINGLET OXYGEN; SURFACE WATER PHOTOCHEMISTRIES;

SURFACE WATERS;

ANTHRAQUINONE; CARBON DIOXIDE; CARBONIC ACID; DISSOLVED ORGANIC MATTER; HYDROXIDE; IBUPROFEN; RIBOFLAVIN; SURFACE WATER;

DISSOLVED ORGANIC MATTER; DRUG; HYDROXYL RADICAL; OXYGEN; PHOTOCHEMISTRY; SURFACE WATER; WATER POLLUTION;

ARTICLE; OXIDATION; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL; QUANTUM YIELD; ULTRAVIOLET B RADIATION;

EID: 81355151142     PISSN: 00431354     EISSN: 18792448     Source Type: Journal    
DOI: 10.1016/j.watres.2011.10.014     Document Type: Article

References (74)

1. Albinet A., Minero C., Vione D. UVA irradiation induces direct phototransformation of 2,4-dinitrophenol in surface water samples. Chemosphere 2010, 80(7):759-763.
2. Albinet A., Minero C., Vione D. Phototransformation processes of 2,4-dinitrophenol, relevant to atmospheric water droplets. Chemosphere 2010, 80(7):753-758.
3. Barbieri Y., Massad W.A., Díaz D.J., Sanz J., Amat-Guerri F., García N.A. Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: kinetics, mechanism and photoproducts. Chemosphere 2008, 73(4):564-571.
4. Bossmann S.H., Oliveros E., Kantor M., Niebler S., Bonfill A., Shahin N., Worner M., Braun A.M. New insights into the mechanisms of the thermal Fenton reactions occurring using different iron(II)-complexes. Water Science and Technology 2004, 49(4):75-80.
5. Bouillon R.C., Miller W.L. Photodegradation of dimethyl sulfide (DMS) in natural waters: Laboratory assessment of the nitrate-photolysis-induced DMS oxidation. Environmental Science and Technology 2005, 39(24):9471-9477.
6. Budac D., Wan P. Photodecarboxylation-Mechanism and synthetic utility. Journal of Photochemistry and Photobiology A: Chemistry 1992, 67(2):135-166.
7. -) in aqueous solution. Journal of Physical and Chemical Reference Data 1988, 17(3):1027-1284.
8. Camacho-Munoz M.D., Sanots J.L., Aparicio I., Alonso E. Presence of pharmaceutically active compounds in Donana Park (Spain) main watersheds. Journal of Hazardous Materials 2010, 177(1-3):1159-1162.
9. 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. Environmental Science & Technology 2005, 39(23):9182-9188.
10. Castiglioni S., Bagnati R., Fanelli R., Pomati F., Calamari D., Zuccato E. Removal of pharmaceuticals in sewage treatment plants in Italy. Environmental Science and Technology 2006, 40(1):357-363.
11. Chiron S., Minero C., Vione D. Occurrence of 2,4-dichlorophenol and of 2,4-dichloro-6-nitrophenol in the Rhône river delta (Southern France). Environmental Science and Technology 2007, 41(9):3127-3133.
12. Daneshvar A., Svanfelt J., Kronberg I., Weyhenmeyer G.A. Winter accumulation of acidic pharmaceuticals in a Swedish river. Environmental Science and Pollution Research 2010, 17(4):908-916.
13. de Graaf M.S., Vieno N.M., Kujawa-Roeleveld K., Zeeman G., Temmink H., Buisman C.J.N. Fate of hormones and pharmaceuticals during combined anaerobic treatment and nitrogen removal by partial nitritation-anammox in vacuum collected black water. Water Research 2011, 45(1):375-383.
14. De Lange H.J., Peeters E.T.H.M., Lurling M. Changes in ventilation and locomotion of Gammarus pulex (Crustacea, Amphipoda) in response to low concentrations of pharmaceuticals. Human and Ecological Risk Assessment 2009, 15(1):111-120.
15. Fernandez C., Gonzales-Doncel M., Pro J., Carbonell G., Tarazona J.V. Occurrence of pharmaceutically active compounds in surface waters of the Henares-Jarama-Tajo river system (Madrid, Spain) and a potential risk characterization. Science of the Total Environment 2010, 408(3):543-551.
16. Frank R., Klöpffer W. Spectral solar photon irradiance in Central Europe and the adjacent North Sea. Chemosphere 1988, 17(5):985-994.
17. Hatipoglu A., Vione D., Yalcin Y., Minero C., Cinar Z. Photo-oxidative degradation of toluene in aqueous media by hydroxyl radicals. Journal of Photochemistry and Photobiology A: Chemistry 2010, 215(1):59-68.
18. Haag W.R., Hoigné J., Gassman E., Braun A.M. Singlet oxygen in surface waters - part I: furfuryl alcohol as a trapping agent. Chemosphere 1984, 13(5-6):631-640.
19. Helenkar A., Sebok A., Zaray G., Molnar-Pearl I., Vasanits-Zsigrai A. The role of the acquisition methods in the analysis of the non-steroidal anti-inflammatory drugs in Danube River by gas chromatography - mass spectrometry. Talanta 2010, 82(2):600-607.
20. Hoigné J. Formulation and calibration of environmental reaction kinetics: Oxidations by aqueous photooxidants as an example. Aquatic Chemical Kinetics 1990, 43-70. Wiley, NY. W. Stumm (Ed.).
21. Islam S.D.M., Penzkofer A., Hegemann P. Quantum yield of triplet formation of riboflavin in aqueous solution and of flavin mononucleotide bound to the LOV1 domain of Phot1 from Chlamydomonas reinhardtii. Chemical Physics 2003, 291(1):97-114.
22. Jacobs L.E., Fimmen R.L., Chin Y.-P., Mash H.E., Weavers L.K. Fulvic acid mediated photolysis of ibuprofen in water. Water Research 2011, 45(15):4449-4458.
23. Kleywegt S., Pileggi V., Yang P., Hao C.Y., Zhao X.M., Rocks C., Thach S., Cheung P., Whitehead B. Pharmaceuticals, hormones and bisphenol A in untreated source and finished drinking water in Ontario, Canada and treatment efficiency. Science of the Total Environment 2011, 409(8):1481-1488.
24. Kouras, S., Amine-Khodja, A., Richard, C. Unpublished results.
25. Kuhn H.J., Braslavsky S.E., Schmidt R. Chemical actinometry. Pure and Applied Chemistry 2004, 76(12):2105-2146.
26. Lewandowski J., Putschew A., Schwesig D., Neumann C., Radke M. Fate of organic micropollutants in the hyporheic zone of a eutrophic lowland stream: results of a preliminary field study. Science of the Total Environment 2011, 409(10):1824-1835.
27. Lin A.Y.C., Reinhard M. Photodegradation of common environmental pharmaceuticals and estrogens in river water. Environmental Toxicology and Chemistry 2005, 24(6):1303-1309.
28. Loeff I., Treinin A., Linschitz H. Photochemistry of 9,10-anthraquinone-2-sulfonate in solution. 1. Intermediates and mechanism. Journal of Physical Chemistry 1983, 87(14):2536-2544.
29. 2 analysis. Water Research 2010, 44(7):2325-2335.
30. Mack J., Bolton J.R. Photochemistry of nitrite and nitrate in aqueous solution: a review. Journal of Photochemistry and Photobiology A: Chemistry 1999, 128(1-3):1-13.
31. Maddigapu P.R., Minero C., Maurino V., Vione D., Brigante M., Mailhot G. Enhancement by anthraquinone-2-sulphonate of the photonitration of phenol by nitrite: Implication for the photoproduction of nitrogen dioxide by coloured dissolved organic matter in surface waters. Chemosphere 2010, 81(11):1401-1406.
32. Maddigapu P.R., Vione D., Ravizzoli B., Minero C., Maurino V., Comoretto L., Chiron S. Laboratory and field evidence of the photonitration of 4-chlorophenol to 2-nitro-4-chlorophenol and of the associated bicarbonate effect. Environmental Science and Pollution Research 2010, 17(5):1063-1069.
33. Maddigapu P.R., Bedini A., Minero C., Maurino V., Vione D., Brigante M., Mailhot G., Sarakha M. The pH-dependent photochemistry of anthraquinone-2-sulfonate. Photochemical and Photobiological Sciences 2010, 9(3):323-330.
34. Maddigapu P.R., Minella M., Vione D., Maurino V., Minero C. Modeling phototransformation reactions in surface water bodies: 2,4-Dichloro-6-nitrophenol as a case study. Environmental Science and Technology 2011, 45(1):209-214.
35. Martell A.E., Smith R.M., Motekaitis R.J. Critically Selected Stability Constants of Metal Complexes Database, Version 4.0 1997.
36. Matamoros V., Duhec A., Albaiges J., Bayona J.M. Photodegradation of carbamazepine, ibuprofen, ketoprofen and 17-alpha-ethinylestradiol in fresh and seawater. Water, Air and Soil Pollution 2009, 196(1-4):161-168.
37. Maurino V., Borghesi D., Vione D., Minero C. Transformation of phenolic compounds upon UVA irradiation of anthraquinone-2-sulfonate. Photochemical and Photobiological Sciences 2008, 7(3):321-327.
38. Maurino V., Bedini A., Borghesi D., Vione D., Minero C. Phenol transformation photosensitised by quinoid compounds. Physical Chemistry Chemical Physics 2011, 10(4):601-609.
39. 2 and simulated solar irradiation. Water Research 2008, 42:585-594.
40. Méndez-Arriaga F., Esplugas S., Giménez J. Degradation of the emerging contaminant ibuprofen in water by photo-fenton. Water Research 2010, 44:589-595.
41. Miller J.S. Rose-Bengal sensitized photooxidation of 2-chlorophenol in water using solar simulated light. Water Research 2005, 39(2-3):412-422.
42. Minella M., Romeo F., Vione D., Maurino V., Minero C. Low to negligible photoactivity of lake-water matter in the size range from 0.1 to 5 μm. Chemosphere 2011, 83(11):1480-1485.
43. Moldovan Z., Chira R., Alder A.C. Environmental exposure of pharmaceuticals and musk fragrances in the Somes River before and after upgrading the municipal wastewater treatment plant Cluj-Napoca, Romania. Environmental Science and Pollution Research 2009, 16(Suppl. I):46-54.
44. Morasch B., Bonvin F., Reiser H., Grandjean D., de Alencastro L.F., Perazzolo C., Chevre N., Kohn T. Occurrence and fate of micropollutants in the Vidy Bay of Lake Geneva, Switzerland. Part II: Micropollutant removal between wastewater and raw drinking water. Environmental Toxicology and Chemistry 2010, 29(8):1658-1668.
45. 2 surface accumulation on photochemistry at the air-water interface of atmospheric droplets. Atmospheric Environment 2010, 44:4859-4866.
46. Oulton R.L., Kohn T., Cwiertny D.M. Pharmaceuticals and personal care products in effluent matrices: a survey of transformation and removal during wastewater treatment and implications for wastewater management. Journal of Environmental Monitoring 2010, 12(11):1956-1978.
47. Packer J.L., Werner J.J., Latch D.E., McNeill K., Arnold W.A. Photochemical fate of pharmaceuticals in the environment: naproxen, diclofenac, clofibric acid, and ibuprofen. Aquatic Sciences 2003, 65(4):342-351.
48. Pailler J.-Y., Krein A., Pfister L., Hoffmann L., Guignard C. Solid phase extraction coupled to liquid chromatography-tandem mass spectrometry analysis of sulfonamides, tetracyclines, analgesics and hormones in surface water and wastewater in Luxenbourg. Science of the Total Environment 2009, 407(16):4736-4743.
49. Parij N., Nagy A.M., Neve J. Linear and non linear competition plots in the deoxyribose assay for determination of rate constants for reaction of non steroidal anti-inflammatory drugs with hydroxyl radicals. Free Radical Research 1995, 23(6):571-579.
50. Peuravuori J., Pihlaja K. Phototransformation of selected pharmaceuticals under low-energy UVA-vis and powerful UVB-UVA irradiations in aqueous solutions - The role of natural dissolved organic chromophoric material. Analytical and Bioanalytical Chemistry 2009, 394(6):1621-1636.
51. Pomati F., Castiglioni S., Zuccato E., Fanelli R., Vigetti D., Rossetti C., Calamari D. Effects of a complex mixture of therapeutic drugs at environmental levels on human embryonic cells. Environmental Science and Technology 2006, 40(7):2442-2447.
52. Prousek J. Fenton chemistry in biology and medicine. Pure and Applied Chemistry 2007, 79(12):2325-2338.
53. Quinn B., Gagne F., Blaise C. The effects of pharmaceuticals on the regeneration of the cnidarian, Hydra attenuata. Science of the Total Environment 2008, 402(1):62-69.
54. Quinn B., Gagne F., Blaise C. Evaluation of the acute, chromic and teratogenic effects of a mixture of eleven pharmaceuticals on the cnidarian, Hydra attenuata. Science of the Total Environment 2009, 407(3):1072-1079.
55. 2 in liquid water as determined by time-resolved infrared luminescence measurements. Journal of the American Chemical Society 1982, 104(20):5541-5543.
56. Santos J.L., Aparicio I., Callejón L., Alonso E. Occurrence of pharmaceutically active compounds during 1-year period in wastewaters from four wastewater treatment plants in Seville (Spain). Journal of Hazardous Materials 2009, 164(2-3):1509-1516.
57. Szabó R.K., Megyeri Cs., Illés L., Gajda-Schrantz K., Mazellier P., Dombi A. Phototransformation of ibuprofen and ketoprofen in aqueous solutions. Chemosphere 2011, 84:1658-1663.
58. Teijon G., Candela L., Tamoh K., Molina-Diaz A., Fernandez-Alba A.R. Occurrence of emerging contaminants, priority substances (2008 105 CE) and heavy metals in treated wastewater and groundwater at Depurbaix facility (Barcelona, Spain). Science of the Total Environment 2010, 408(17):3584-3595.
59. Tiehm A., Schmidt N., Stieber M., Sacher F., Wolf L., Hoetzl H. Biodegradation of pharmaceutical compounds and their occurrence in the Jordan Valley. Water Resources Management 2011, 25(4):1195-1203.
60. Tixier C., Singer H.P., Oellers S., Müller S.R. Occurrence and fate of carbamazepine, clofibric acid, diclofenac, ibuprofen, ketoprofen, and naproxen in surface waters. Environmental Science and Technology 2003, 37(6):1061-1068.
61. Valcarcel Y., Alonso S.G., Rodriguez-Gil J.L., Maroto R.R., Gil A., Catala M. Analysis of the presence of cardiovascular and analgesic/anti-inflammatory/antipyretic pharmaceuticals in river- and drinking-water of the Madrid Region in Spain. Chemosphere 2011, 82(7):1062-1071.
62. •OH scavengers bicarbonate and carbonate. Water Research 2009, 43(18):4718-4728.
63. Vione D., Maurino V., Minero C., Carlotti M.E., Chiron S., Barbati S. Modelling the occurrence and reactivity of the carbonate radical in surface freshwater. Comptes Rendus Chimie 2009, 12(8):865-871.
64. 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 Research 2010, 44(20):6053-6062.
65. Waiser M.J., Humphries D., Tumber V., Holm J. Effluent-dominated streams. Part 2: presence and possible effects of pharmaceuticals and personal case products in wascana Creek, Saskatchewan, Canada. Environmental Toxicology and Chemistry 2011, 30(2):508-519.
66. Wang C.A., Shi H.L., Adams C.D., Gamagedara S., Stayton I., Timmons T., Ma Y.F. Investigation of pharmaceuticals in Missouri natural and drinking water using high performance liquid chromatography - tandem mass spectrometry. Water Research 2011, 45(4):1818-1828.
67. Wang L., Ying G.G., Zhao J.L., Yang X.B., Chen F., Tao R., Liu S., Zhou L.J. Occurrence and risk assessment of acidic pharmaceuticals in the yellow River, Hai River and Liao River of north China. Science of the Total Environment 2010, 408(16):3139-3147.
68. Wilkinson F., Brummer J. Rate constants for the decay and reactions of the lowest electronically excited singlet-state of molecular oxygen in solution. Journal of Physical and Chemical Reference Data 1981, 10(4):809-1000.
69. Yu C.P., Chu K.H. Occurrence of pharmaceuticals and personal care products along the West Prong little Pigeon River in east Tennessee, USA. Chemosphere 2009, 75(10):1281-1286.
70. 2. Water Research 2009, 43(6):1766-1774.
71. Zhang X., Oakes K.D., Ciu S.F., Bragg L., Servos M.R., Pawliszyn J. Tissue-specific in vivo bioconcentration of pharmaceuticals in rainbow trout (Oncorhynchus mykiss) using space-resolved solid-phase microextraction. Environmental Science and Technology 2010, 44(9):3417-3422.
72. Zhao J.L., Ying G.G., Wang L., Yang J.F., Yang X.B., Yang L.H., Li X. Determination of phenolic endocrine disrupting chemicals and acidic pharmaceuticals in surface waters of the Pearl Rivers in South China by gas chromatography-negative chemical ionization-mass spectrometry. Science of the Total Environment 2009, 407(2):962-974.
73. Zhao J.L., Ying G.G., Liu Y.S., Chen F., Yang J.F., Wang L., Yang X.B., Stauber J.L., Warne M.S. Occurrence and a screening-level risk assessment of human pharmaceuticals in the Pearl River system, South China. Environmental Toxicology and Chemistry 2010, 29(6):1377-1384.
74. Zuccato E., Castiglioni S., Fanelli R. Identification of the pharmaceuticals for human use contaminating the Italian aquatic environment. Journal of Hazardous Materials 2005, 122(3):205-209.