Oxidation of flame retardant tetrabromobisphenol a by aqueous permanganate: Reaction kinetics, brominated products, and pathways

Environmental Science and Technology

Volumn 48, Issue 1, 2014, Pages 615-623

  Pang, Su Yan ^a   Jiang, Jin ^b   Gao, Yuan ^b   Zhou, Yang ^b   Huangfu, Xiaoliu ^b   Liu, Yongze ^b   Ma, Jun ^b  

^a HARBIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b HARBIN INSTITUTE OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSPRAY IONIZATION; FLAME RETARDANTS; ISOTOPES; MANGANESE; MASS SPECTROMETRY; OXIDATION; RATE CONSTANTS; REACTION INTERMEDIATES; REACTION KINETICS;

BROMINATED FLAME RETARDANTS; ONE-ELECTRON OXIDATION; POTASSIUM PERMANGANATE; PRODUCT ION SPECTRA; QUADRUPOLE MASS SPECTROMETRY; SECOND-ORDER RATE CONSTANTS; SELECTIVE DETECTION; TETRABROMOBISPHENOL A;

MANGANESE REMOVAL (WATER TREATMENT);

MANGANESE; PERMANGANATE POTASSIUM; TETRABROMOBISPHENOL A; FLAME RETARDANT; FRESH WATER; POLYBROMINATED BIPHENYL; WASTE WATER; WATER POLLUTANT;

AQUEOUS SOLUTION; BROMINE COMPOUND; MANGANESE; OXIDATION; PH; PHENOLIC COMPOUND; POTASSIUM; REACTION KINETICS; WASTEWATER;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; ELECTRON; ELECTRON TRANSPORT; ELECTROSPRAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; QUADRUPOLE MASS SPECTROMETRY; REACTION ANALYSIS; WASTE WATER MANAGEMENT; ANALYSIS; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; KINETICS; OXIDATION REDUCTION REACTION; PROCEDURES; WASTE WATER; WATER MANAGEMENT; WATER POLLUTANT;

FLAME RETARDANTS; FRESH WATER; KINETICS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYBROMINATED BIPHENYLS; POTASSIUM PERMANGANATE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; WASTE WATER; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

EID: 84891817110     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es4041094     Document Type: Article

References (49)

1. de Wit, C. A. An overview of brominated flame retardants in the environment Chemosphere 2002, 46, 583-624
2. Law, R. J.; Allchin, C. R.; de Boer, J.; Covaci, A.; Herzke, D.; Lepom, P.; Morris, S.; Tronczynski, J.; de Wit, C. A. Levels and trends of brominated flame retardants in the European environment Chemosphere 2006, 64, 187-208
3. Birnbaum, L. S.; Staskal, D. F. Brominated flame retardants: Cause for concern Environ. Health Perspect. 2004, 112, 9-17
4. Morris, S.; Allchin, C. R.; Zegers, B. N.; Haftka, J. J. H.; Boon, J. P.; Belpaire, C.; Leonards, P. E. G.; van Leeuwen, S. P. J.; de Boer, J. Distribution and fate of HBCD and TBBPA brominated flame retardants in north sea estuaries and aquatic food webs Environ. Sci. Technol. 2004, 38, 5497-5504
5. Osako, M.; Kim, Y.; Sakai, S. Leaching of brominated flame retardants in leachate from landfills in Japan Chemosphere 2004, 57, 1571-1579
6. Kitamura, S.; Jinno, N.; Ohta, S.; Kuroki, H.; Fujimoto, N. Thyroid hormonal activity of the flame retardants tetrabromobisphenol A and tetrachlorobisphenol A Biochem. Biophys. Res. Commun. 2002, 293, 554-559
7. Kitamura, S.; Suzuki, T.; Sanoh, S.; Kohta, R.; Jinno, N.; Sugihara, K.; Yoshihara, S.; Fujimoto, N.; Watanabe, H.; Ohta, S. Comparative study of the endocrine-disrupting activity of bisphenol A and 19 related compounds Toxicol. Sci. 2005, 84, 249-259
8. Olsen, C. M.; Meuseen-Elholm, E. T. M.; Samuelsen, M.; Holme, J. A.; Hongslo, J. K. Effects of the environmental estrogens bisphenol A, tetrachlorobisphenol A, tetrabromobisphenol A, 4-hydroxybiphenyl and 4,42-dihydroxybiphenyl on estrogen receptor binding, cell proliferation and regulation of estrogen sensitive proteins in the human breast cancer cell line MCF-7 Pharmacol. Toxicol. 2003, 92, 180-188
9. Lin, K.; Liu, W.; Gan, J. Reaction of tetrabromobisphenol A (TBBPA) with manganese dioxide: Kinetics, products, and pathways Environ. Sci. Technol. 2009, 43, 4480-4486
10. Feng, Y.; Colosi, L. M.; Gao, S.; Huang, Q.; Mao, L. Transformation and removal of tetrabromobisphenol A from water in the presence of natural organic matter via laccase-catalyzed reactions: Reaction rates, products, and pathways Environ. Sci. Technol. 2013, 47, 1001-1008
11. Xu, J.; Meng, W.; Zhang, Y.; Li, L.; Guo, C. Photocatalytic degradation of tetrabromobisphenol A by mesoporous BiOBr: efficacy, products and pathways Appl. Catal., B 2011, 107, 355-362
12. Zhang, Y.; Liang, X.; Zhong, Y.; Zhu, J.; Zhu, S.; Yuan, P.; He, H.; Zhang, J. Heterogeneous UV/Fenton degradation of TBBPA catalyzed by titanomagnetite: Catalyst characterization, performance and degradation products Water Res. 2012, 46, 4633-4644
13. 4 as a heterogeneous catalyst of peroxymonosulfate Appl. Catal., B 2013, 153-162
14. Jiang, J.; Pang, S.-Y.; Ma, J.; Liu, H. Oxidation of phenolic endocrine disrupting chemicals by potassium permanganate in synthetic and real waters Environ. Sci. Technol. 2012, 46, 1774-1781
15. VI, and ozone) and non-selective oxidants (hydroxyl radical) Water Res. 2010, 44, 555-566
16. Hu, L.; Martin, H. M.; Arce-Bulted, O.; Sugihara, M. N.; Keating, K. A.; Strathmann, T. J. Oxidation of carbamazepine by Mn(VII) and Fe(VI): Reaction kinetics and mechanism Environ. Sci. Technol. 2009, 43, 509-515
17. Waldemer, R. H.; Tratnyek, P. G. Kinetics of contaminant degradation by permanganate Environ. Sci. Technol. 2006, 40, 1055-1061
18. Ma, J.; Graham, N.; Li, G. Effect of permanganate preoxidation in enhancing the coagulation of surface water-laboratory case studies J. Water Supply Res. Technol.-AQUA 1997, 46, 1-10
19. Chen, J.-J.; Yeh, H.-H. The mechanisms of potassium permanganate on algae removal Water Res. 2005, 39, 4420-4428
20. Hu, L.; Martin, H.; Strathmann, T. J. Oxidation kinetics of antibiotics during water treatment with potassium permanganate Environ. Sci. Technol. 2010, 44, 6416-6422
21. Hu, L.; Stemig, A. M.; Wammer, K. H.; Strathmann, T. J. Oxidation of antibiotics during water treatment with potassium permanganate: Reaction pathways and deactivation Environ. Sci. Technol. 2011, 45, 3635-3642
22. Jiang, J.; Pang, S.-Y.; Ma, J. Oxidation of triclosan by permanganate (Mn(VII)): Importance of ligands and in situ formed manganese oxides Environ. Sci. Technol. 2009, 43, 8326-8331
23. Jiang, J.; Pang, S.-Y.; Ma, J. Role of ligands in permanganate oxidation of organics Environ. Sci. Technol. 2010, 44, 4270-4275
24. Zhang, X.; Talley, J. W.; Boggess, B.; Ding, G.; Birdsell, D. Fast selective detection of polar brominated disinfection byproducts in drinking water using precursor ion scans Environ. Sci. Technol. 2008, 42, 6598-6603
25. Zhai, H.; Zhang, X. Formation and decomposition of new and unknown polar brominated disinfection byproducts during chlorination Environ. Sci. Technol. 2011, 45, 2194-2201
26. Fasfous, I. I.; Radwanl, E. S.; Dawoud, J. N. Kinetics, equilibrium and thermodynamics of the sorption of tetrabromobisphenol A on multiwalled carbon nanotubes Appl. Surf. Sci. 2010, 256, 7246-7252
27. Lee, Y.; Zimmermann, S. G.; Kieu, A. T.; von Gunten, U. Ferrate (Fe(VI)) application for municipal wastewater treatment: A novel process for simultaneous micropollutant oxidation and phosphate removal Environ. Sci. Technol. 2009, 43, 3831-3838
28. 4. Ph.D. Thesis, New Mexico State University, Las Cruces, NM, 1999.
29. Elovitz, M.; Fish, W. Redox interactions of Cr(VI) and substituted phenols: Products and mechanism Environ. Sci. Technol. 1995, 29, 1933-1943
30. Pan, Y.; Zhang, X. Four groups of new aromatic halogenated disinfection byproducts: Effect of bromide concentration on their formation and speciation in chlorinated drinking water Environ. Sci. Technol. 2013, 47, 1265-1273
31. Xiao, F.; Zhang, X.; Zhai, H.; Lo, I. M. C.; Tipoe, G. L.; Yang, M.; Pan, Y.; Chen, G. New halogenated disinfection byproducts in swimming pool water and their permeability across skin Environ. Sci. Technol. 2012, 46, 7112-7119
32. Ding, G.; Zhang, X.; Yang, M.; Pan, Y. Formation of new brominated disinfection byproducts during chlorination of saline sewage effluents Water Res. 2013, 47, 2710-2718
33. Deborde, M.; Rabouan, S.; Mazellier, P.; Duguet, J.-P.; Legube, B. Oxidation of bisphenol A by ozone in aqueous solution Water Res. 2008, 42, 4299-4308
34. Li, C.; Li, X.-Z.; Graham, N.; Gao, N.-Y. The aqueous degradation of bisphenol A and steroid estrogens by ferrate Water Res. 2008, 42, 109-120
35. Lin, K.; Liu, W.; Gan, J. Oxidative removal of bisphenol A by manganese dioxide: efficacy, products, and pathways Environ. Sci. Technol. 2009, 43, 3860-3864
36. Huang, Q.; Weber, W. J., Jr. Transformation and removal of bisphenol A from aqueous phase via peroxidase-mediated oxidative coupling reactions: Efficacy, products, and pathways Environ. Sci. Technol. 2005, 39, 6029-6036
37. Zhang, J.; Sun, B.; Guan, X. Oxidative removal of bisphenol A by permanganate: Kinetics, pathways and influences of co-existing chemicals Sep. Purif. Technol. 2013, 107, 48-53
38. Bender, M.; Maccrehan, W. A. Transformation of Acetaminophen by Chlorination Produces the Toxicants 1,4-Benzoquinone and N-Acetyl-p-benzoquinone Imine Environ. Sci. Technol. 2006, 40, 516-522
39. Xagoraraki, I.; Hullman, R.; Song, W.; Li, H.; Voice, T. Effect of pH on degradation of acetaminophen and production of 1,4-benzoquinone in water chlorination J. Water Supply Res. Technol. -Aqua 2008, 381-390
40. Sarr, D. H.; Kazunga, C.; Charles, M. J.; Pavlovich, J. G.; Aitken, M. D. Decomposition of Tetrachloro-1,4-benzoquinone (p-Chloranil) in Aqueous Solution Environ. Sci. Technol. 1995, 29, 2735-2740
41. Zhu, B. Z.; Kalyanaraman, B.; Jiang, G. Molecular mechanism for metal-independent production of hydroxyl radicals by hydrogen peroxide and halogenated quinines Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 17575-17578
42. Zhao, Y.; 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 Anal. Chem. 2010, 82, 4599-4605
43. Huang, R.; Wang, W.; Qian, Y.; Boyd, J. M.; Zhao, Y.; Li, X.-F. Ultra pressure liquid chromatography-negative electrospray ionization mass spectrometry determination of twelve halobenzoquinones at ng/L levels in drinking water Anal. Chem. 2013, 85, 4520-4529
44. Wu, Q.; Shi, H.; Adams, C. D.; Timmons, T.; Ma, Y. Oxidative removal of selected endocrine-disruptors and pharmaceuticals in drinking water treatment systems, and identification of degradation products of triclosan Sci. Total Environ. 2012, 439, 18-25
45. Zhang, H.; Huang, C.-H. Oxidative transformation of triclosan and chlorophene by manganese oxides Environ. Sci. Technol. 2003, 37, 2421-2430
46. Yang, B.; Ying, G.-G.; Zhao, J.-L.; Zhang, L.-J.; Fang, Y.-X.; Nghiem, L. D. Oxidation of triclosan by ferrate Reaction kinetics, products identification and toxicity evaluation J. Hazard. Mater. 2011, 186, 227-235
47. Chen, X. J.; Richard, J.; Liu, Y. L.; Dopp, E.; Tuerk, J.; Bester, K. Ozonation products of triclosan in advanced wastewater treatment Water Res. 2012, 46, 2247-2256
48. Bruchajzer, E.; Szymanska, J. A.; Piotrowski, J. K. Acute and subacute nephrotoxicity of 2-bromophenol in rats Toxicol. Lett. 2002, 134, 245-252
49. Bull, R. J.; Reckhow, D. A.; Rotello, V.; Bull, O. M.; Kim, J. Use of Toxicological and Chemical Models to Prioritize DBP Research; American Water Works Association Research Foundation and American Water Works Association: Denver, CO, 2006.