Transformation mechanism of benzophenone-4 in free chlorine promoted chlorination disinfection

Water Research

Volumn 47, Issue 16, 2013, Pages 6223-6233

  Xiao, Ming ^a,b   Wei, Dongbin ^a   Yin, Junxia ^a   Wei, Guohua ^a   Du, Yuguo ^a,b  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Benzophenone; Chlorination; Genotoxicity; UV filters

Indexed keywords

BANDPASS FILTERS; CARBOXYLATION; CHEMICALS REMOVAL (WATER TREATMENT); CHLORINE; CHLORINE COMPOUNDS; DISINFECTION; ESTERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KETONES; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; POTABLE WATER; SOLUTIONS; WASTEWATER RECLAMATION; WASTEWATER TREATMENT;

BENZOPHENONE; FREE AVAILABLE CHLORINES; FREE CHLORINE; GENOTOXICITIES; HIGH POTENTIAL; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; SULPHONIC ACIDS; TRANSFORMATION MECHANISMS; TREATMENT SYSTEMS; UV FILTER;

CHLORINATION;

BENZENE; BENZOPHENONE; CARBOXYL GROUP; CHLORINE; ESTER DERIVATIVE; SULISOBENZONE;

BIOTRANSFORMATION; CARBOXYLIC ACID; CHLORINATION; DISINFECTION; DRINKING WATER; ESTER; GENOTOXICITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR ANALYSIS; ORGANIC COMPOUND; OXIDATION; PH; ULTRAVIOLET RADIATION;

AQUEOUS SOLUTION; ARTICLE; CHLORINATION; DECARBOXYLATION; DISINFECTION; GAS CHROMATOGRAPHY; GENOTOXICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; KINETICS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PH; PRIORITY JOURNAL; REACTION ANALYSIS;

BENZOPHENONE; CHLORINATION; GENOTOXICITY; UV-FILTERS;

BENZOPHENONES; CHLORINE; HALOGENATION; WATER PURIFICATION;

EID: 84885475393     PISSN: 00431354     EISSN: 18792448     Source Type: Journal    
DOI: 10.1016/j.watres.2013.07.043     Document Type: Article

References (63)

1. Alvarez D.A., Petty J.D., Huckins J.N., Jones-Lepp T.L., Getting D.T., Goddard J.P., Manahan S.E. Development of a passive, in situ, integrative sampler for hydrophilic organic contaminants in aquatic environments. Environmental Toxicology and Chemistry 2004, 23:1640-1648.
2. Anichina J., Zhao Y.L., Hrudey S.E., Chrisle X., Li X.F. Electrospray ionization mass spectrometry characterization of interactions of newly identified water disinfection byproducts halobenzoquinones with oligodeoxynucleotides. Environmental Science and Technology 2010, 44:9557-9563.
3. APHA Standard Methods for the Examination of Water and Wastewater 1998, 1287. American Public Health Association, New York. twentieth ed.
4. Baeyer A., Villiger V. Einwirkung des Caro'schen Reagens auf Ketone. Berichte der deutschen chemischen Gesellschaft 1899, 32(3):3625-3633. (in Ger.).
5. Bolm C., Schlingloff G. Metal-catalysed enantiospecific aerobic oxidation of cyclobutanones. Journal of the Chemical Society - Chemical Communications 1995, 1247-1248.
6. Buth J.M., Arnold W.A., Mcneill K. Unexpected products and reaction mechanisms of the aqueous chlorination of cimetidine. Environmental Science and Technology 2007, 41:6228-6233.
7. Czaplicka M. Photo-degradation of chlorophenols in the aqueous solution. Journal of Hazardous Materials 2006, 134:45-59.
8. Deborde M., von Gunten U. Reactions of chlorine with inorganic and organic compounds during water treatment-kinetics and mechanisms: a critical review. Water Research 2008, 42:13-51.
9. DellaGreca M., Iesce M.R., Pistillo P., Previtera L., Temussi F. Unusual products of the aqueous chlorination of atenolol. Chemosphere 2009, 74:730-734.
10. Diaz-Cruz M.S., Llorca M., Barcelo D. Organic UV filters and their photodegradates, metabolites, and disinfection byproducts in the aquatic environment. Trends in Analytical Chemistry 2008, 27(10):873-887.
11. Dodd M.C., Huang C.H. Transformation of the antibacterial agent sulfamethoxazole in reactions with chlorine: kinetics, mechanisms, and pathways. Environmental Science and Technology 2004, 38:5607-5615.
12. European Commission (EC) Council Directive 76/768/EEC of 27 July 1976 and Its Successive Amendments 1976, http://europa.eu.int/eur-lex/en/lif/reg/en_ergister_133016.html.
13. US Food and Drug Administration (FDA) Sunscreen drug products for over-the-counter human use, 21 CFR Parts 310, 352, 700, and 740, RIN 0910-AA01 final monograph. Federal Register Rules and Regulations 1999, 64(98):27666-27693. Food and Drug Administration. http://www.fda.gov/ohrms/dockets/98fr/052199b.pdf.
14. Fent K., Zenker A., Rapp M. Widespread occurrence of estrogenic UV-filters in aquatic ecosystems in Switzerland. Environmental Pollution 2010, 158:1817-1824.
15. Fermin M.C., Bruno J.W. Oxygen atom transfer with niobocene ketenes, Baeyer-Villiger chemistry with unusual regioselectivities. Tetrahedron Letters 1993, 34(47):7545-7548.
16. French J.E. NTP Technical Report on Toxicity Studies of 2-hydroxy-4-methoxy-benzophenone 1992, National Toxicology Report No. 21, NIH Publication No. 92-3344.
17. Ghigo G., Tonachini G. From benzene to muconaldehyde: theoretical mechanistic investigation on some tropospheric oxidation channels. Journal of the American Chemical Society 1999, 121:8366-8372.
18. Gilbert E.E. Sulfonation and Related Reactions 1965, 1-529. Interscience Publishers, New York.
19. Giokas D.L., Salvador A., Chisvert A. UV filters: from sunscreens to human body and the environment. TRAC - Trends in Analytical Chemisty 2007, 26(5):360-374.
20. Horton J.A., Laura M.A., Kalbag S.M., Petterson R.C. Reaction of hypochlorous acid with ketones. A novel Baeyer-Villiger oxidation of cyclobutanone with hypochlorous acid. Journal of Organic Chemistry 1969, 34(11):3366-3368.
21. Hu J.Y., Aizawa T., Ookubo S. Products of aqueous chlorination of bisphenol A and their estrogenic activity. Environmental Science and Technology 2002, 36:1980-1987.
22. Hu J.Y., Cheng S.J., Aizawa T., Terao Y., Kunikane S. Products of aqueous chlorination of 17-beta-estradiol and their estrogenic activities. Environmental Science and Technology 2003, 37:5664-5670.
23. Hu J.Y., Jin X., Kunikane S., Aizawa T. Transformation of pyrene in aqueous chlorination in the presence and absence of bromide ion: kinetics, products, and their aryl hydrocarbon receptor-mediated activities. Environmental Science and Technology 2006, 40(2):487-493.
24. ISO (International Standard Organisation) Water Quality-determination of the Genotoxicity of Water and Waste Water Using the Umu-test 2000, 1-18. ISO 13829, ISO, Geneva. first ed.
25. Jencks W.P., Carriuolo J. Reactivity of nucleophilic reagents toward esters. Journal of the American Chemical Society 1960, 82:1778-1786.
26. Justine C., Sebastien A., Elisabeth S., Joll C.A., Heitz A., von Gunten U. Iodate and iodo-trihalomethane formation during chlorination of iodide-containing waters: role of bromide. Environmental Science and Technology 2012, 46:7350-7357.
27. Kawamura Y., Ogawa Y., Nishimura T., Kikuchi Y., Nishikawa J., Nishihara T., Tanamoto K. Estrogenic activities of UV stabilizers used in food contact plastics and benzophenone derivatives tested by the yeast two-hybrid assay. Journal of Health Science 2003, 49:205-212.
28. Kosaka K., Koshino H., Yoshida N., Kunikane S. Behaviour of pyrene and its decomposition by-products in chlorination. Journal of Water Supply Research Technology-AQUA 2010, 59:41-52.
29. Kupper T., Plagellat C., Brandli R.C., de Alencastro L.F., Grandjean D., Tarradellas J. Fate and removal of polycyclic musks, UV filters and biocides during wastewater treatment. Water Research 2006, 40:2603-2612.
30. Larson R.A., Rockwell A.L. Chlorofor, and cyclophenol production by decarboxylation of natural acids during aqueous chlorination. Environmental Science and Technology 1979, 13:325-329.
31. Lindstrom K., Nordin J. Gas chromatography-mass spectrometry of chlorophenols in spent bleach liquors. Journal of Chromatography A 1976, 128:13-26.
32. Liu Y.S., Ying G.G., Shareef A., Kookana R.S. Occurrence and removal of benzotriazoles and ultraviolet filters in a municipal wastewater treatment plant. Environmental Pollution 2012, 165:225-232.
33. Marchand A.P., Kumar V.S., Hariprakasha H.K. Synthesis of novel cage oxaheterocycles. Journal of Organic Chemistry 2001, 66:2072-2077.
34. Ministry of Health and Welfare (MHLW) Japanese Standards of Cosmetic Ingredients 2000, Ministry of Health and Welfare Notification No.331 of 2000, Japan.
35. Ministry of Environment (MOE) MOE's Perspectives on Endocrine Disrupting Effects of Substances - Strategic Programs on Environmental Endocrine Disruptors (SPEED'98) 2000, Japan. http://www.env.go.jp/chemi/end/endindex.html.
36. Ministry of Health (MOH) Hygienic Standard for Cosmetics Jan. 2007, Ministry of Health, China.
37. Morris J.C. The chemistry of aqueous chlorine in relation to water chlorination. Water Chlorination: Environmental Impact and Health Effects 1975, vol. 1:21-35. Ann Arbor Science Publishers, Michigan.
38. Negreira N., Canosa P., Rodríguez I., Ramil M., Rubi E., Cela R. Study of some UV filters stability in chlorinated water and identification of halogenated by-products by gas chromatography-mass spectrometry. Journal of Chromatography A 2008, 1178:206-214.
39. Negreira N., Rodríguez I., Rodil R., Cela R. Assessment of benzophenone-4 reactivity with free chlorine by liquid chromatography quadrupole time-of-flight mass spectrometry. Analytica Chimica Acta 2012, 743:101-110.
40. Norwood D.L., Johnson J.D., Christman R.F., Hass J.R., Bobenrieth M.J. Reactions of chlorine with selected aromatic models of aquatic humic material. Environmental Science and Technology 1980, 14:187-190.
41. Oda Y., Nakamura S., Oki I., Kato T., Shinagawa H. Evaluation of the new system (umu-test) for the detection of environmental mutagens and carcinogens. Mutation Research 1985, 147:219-229.
42. Onodera S., Udagawa T., Tabata M., Ishikura S., Suzuki S. Isotachophoretic determination of chlorinated carboxylic acids formed during chlorination of phenol with hypochlorite in dilute aqueous solution. Journal of Chromatography A 1984, 287:176-182.
43. Pinkston K.E., Sedlak D.L. Transformation of aromatic ether- and amine-containing pharmaceuticals during chlorine disinfection. Environmental Science and Technology 2004, 38:4019-4025.
44. Plagellat C., Kupper T., Furrer R., de Alencastro L.F., Grandjean D., Taradellas J. Concentrations and specific loads of UV filters in sewage sludge originating from a monitoring network in Switzerland. Chemosphere 2006, 62:915-925.
45. Poiger T., Buser H.-R., Balmer M.E., Bergqvist P.-A., Muller M.D. Occurrence of UV filter compounds from sunscreens in surface waters: regional mass balance in two Swiss lakes. Chemosphere 2004, 55(7):951-963.
46. Richardson S.D., Ternes T.A. Water analysis: emerging contaminants and current issues. Analytical Chemistry 2011, 83(12):4614-4648.
47. Richardson S.D., Plewa M.J., Wagner E.J., Schoeny R., DeMarini D.M. Occurrence, genotoxicity, and carcinogenicity of regulated and emerging disinfection by-products in drinking water: a review and roadmap for research. Mutation Research 2007, 636:178-242.
48. Rodil R., Quintana J.B., Lopez-Mahia P., Muniategui-Lorenzo S., Prada-Rodriguez D. Multiclass determination of sunscreen chemicals in water samples by liquid chromatography-tandem mass spectrometry. Analytical Chemistry 2008, 80:1307-1315.
49. Rodil R., Quintana J.B., López-Mahía P., Muniategui-Lorenzo S., Prada-Rodríguez D. Multi-residue analytical method for the determination of emerging pollutants in water by solid-phase extraction and liquid chromatography-tandem massspectrometry. Journal of Chromatography A 2009, 1216:2958-2969.
50. Roelandts R., Vanhee J., Bonamie A., Kerkhofs L., Degreef H. A survey of ultraviolet absorbers in commercially available sun products. International Journal of Dermatology 1983, 22(4):247-255.
51. Sakkas V.A., Giokas D.L., Lambropoulou D.A., Albanis T.A. Aqueous photolysis of the sunscreen agent octyl-dimethyl-p-aminobenzoic acid formation of disinfection by products in chlorinated swimming pool water. Journal of Chromatography A 2003, 1016:211-222.
52. Schlumpf M., Cotton B., Conscience M., Haller V., Steinmann B., Lichtensteiger W. Invitro and invivo estrogenicity of UV screens. Environmental Health Perspectives 2001, 109:239-244.
53. Stenback F. Local and systematic effects of commonly used cutaneous agents -lifetime studies of 16 mice and rabbits. Acta Pharmacologica et Toxicologica 1977, 41:417-431.
54. Therapeutic Goods Administration (TGA) Australian Regulatory Guidelines for OTC Medicines 2003, Therapeutic goods administration, Australia.
55. Tomson M.B., Dauchy J., Hutchins S., Curran C., Cook C.J., Ward C.H. Groundwater contamination by trace level organics from a rapid infiltration site. Water Research 1981, 15(9):1109-1116.
56. Vollmuth S., Zajc A., Niessner R. Formation of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans during the photolysis of pentachlorophenol-containing water. Environmental Science and Technology 1994, 28:1145-1149.
57. Wahie S., Lloyd J.J., Farr P.M. Sunscreen ingredients and labeling: a survey of products available in UK. Clinical and Experimental Dermatology 2007, 32:359-364.
58. Witz G., Zhang Z.H., Goldstein B.D. Reactive ring-opened aldehyde metabolites in benzene hematotoxicity. Environmental Health Perspectives 1996, 104(S6):1195-1199.
59. Wu Q.Y., Li Y., Hu H.Y., Sun Y.X., Zhao F.Y. Reduced effect of bromide on the genotoxicity in secondary effluent of a municipal wastewater treatment plant during chlorination. Environmental Science and Technology 2010, 44:4924-4929.
60. Yang X., Shang C. Chlorination byproduct formation in the presence of humic acid, model nitrogenous organic compounds, ammonia, and bromide. Environmental Science and Technology 2004, 38:4995-5001.
61. Zeiger E., Anderson B., Haworth S., Lawlor T., Mortelmans K., Speck W. Salmonella mutagenicity tests. 3. Results from the testing of 255 chemicals. Environmental Mutagenesis 1987, 9:1-109.
62. Zenker A., Schmutz H., Fent K. Simultaneous trace determination of nine organic UV-absorbing compounds (UV-filters) in environmental samples. Journal of Chromatography A 2008, 1202:64-74.
63. Zhao Y.L., Qin F., Boyd J.M., Anichina J., Li X.F. Characterization and determination of chloro- and bromo-benzoquinones as new chlorination disinfection byproducts in drinking water. Analytical Chemistry 2010, 82:4599-4605.