Oxidative degradation of decabromodiphenyl ether (BDE 209) by potassium permanganate: Reaction pathways, kinetics, and mechanisms assisted by density functional theory calculations

Environmental Science and Technology

Volumn 49, Issue 7, 2015, Pages 4209-4217

  Shi, Jiaqi ^a   Qu, Ruijuan ^a   Feng, Mingbao ^a   Wang, Xinghao ^a   Wang, Liansheng ^a   Yang, Shaogui ^a   Wang, Zunyao ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; MOLECULAR ORBITALS; ORGANIC POLLUTANTS; OXIDATION; POTASSIUM; REACTION KINETICS;

DECABROMODIPHENYL ETHERS (BDE209); FRONTIER ELECTRON DENSITIES; FRONTIER MOLECULAR ORBITALS; HYDROXYLATED POLYBROMINATED DIPHENYL ETHERS; OXIDATIVE DEGRADATION; POTASSIUM PERMANGANATE; PSEUDO FIRST-ORDER KINETICS; THEORETICAL CALCULATIONS;

DENSITY FUNCTIONAL THEORY;

FERRIC OXIDE; HYDROXYL RADICAL; IRON OXIDE; MAGNETITE NANOPARTICLE; NALIDIXIC ACID; DECABROMOBIPHENYL ETHER; DIPHENYL ETHER DERIVATIVE; PERMANGANATE POTASSIUM; POLLUTANT;

BIODEGRADATION; CHEMICAL BONDING; ETHER; OXIDATION; REACTION KINETICS; SULFURIC ACID;

ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; COLORIMETRY; CONTROLLED STUDY; DEGRADATION; FENTON REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MOLECULAR WEIGHT; OXIDATION; PARTICLE SIZE; REACTION ANALYSIS; SOLID PHASE EXTRACTION; SURFACE PROPERTY; TRANSMISSION ELECTRON MICROSCOPY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; WASTE WATER MANAGEMENT; X RAY ABSORPTION SPECTROSCOPY; X RAY DIFFRACTION; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; KINETICS; OXIDATION REDUCTION REACTION; POLLUTANT;

ENVIRONMENTAL POLLUTANTS; HALOGENATED DIPHENYL ETHERS; HYDROXYLATION; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POTASSIUM PERMANGANATE;

EID: 84926444282     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es505111r     Document Type: Article

References (65)

1. Chen, C.; Chen, J. W.; Zhao, H. X.; Xie, Q.; Yin, Z. Q.; Ge, L. K. Levels and patterns of polybrominated diphenyl ethers in childrens plasma from Dalian, China Environ. Int. 2010, 36, 163-167
2. Chiuchiolo, A. L.; Dickhut, R. M.; Cochran, M. A.; Ducklow, H. W. Persistent organic pollutants at the base of the Antarctic marine food web Environ. Sci. Technol. 2004, 38, 3551-3557
3. de Wit, C. A.; Alaee, M.; Muir, D. C. G. Levels and trends of brominated flame retardants in the Arctic Chemosphere 2006, 64, 209-233
4. Hassanin, A.; Breivik, K.; Meijer, S. N.; Steinnes, E.; Thomas, G. O.; Jones, K. C. PBDEs in European background soils: Levels and factors controlling their distribution Environ. Sci. Technol. 2004, 38, 738-745
5. He, W.; Qin, N.; Kong, X. Z.; Liu, W. X.; He, Q. S.; Ouyang, H. L.; Wang, Q. M.; Yang, B.; Yang, C.; Jiang, Y. J.; Xu, F. L. Polybrominated diphenyl ethers (PBDEs) in the surface sediments and suspended particulate matter (SPM) from Lake Chaohu, a large shallow Chinese lake Sci. Total Environ. 2013, 463-464, 1163-1173
6. Martin, M.; Lam, P.; Richardson, B. An Asian quandary: Where have all of the PBDEs gone? Mar. Pollut. Bull. 2004, 49, 375-382
7. Schecter, A.; Päpke, O.; Tung, K. C.; Staskal, D.; Birnbaum, L. Polybrominated diphenyl ethers contamination of United States food Environ. Sci. Technol. 2004, 38, 5306-5311
8. Venkatesan, A. K.; Halden, R. U. Brominated flame retardants in U.S. biosolids from the EPA national sewage sludge survey and chemical persistence in outdoor soil mesocosms Water Res. 2014, 55, 133-142
9. Darnerud, P. O. Toxic effects of polybrominated diphenyl ethers in man and in wildlife Environ. Int. 2003, 29, 841-853
10. Gaylor, M. O.; Harvey, E.; Hale, R. C. Polybrominated diphenyl ether (PBDE) accumulation by earthworms (Eisenia fetida) exposed to biosolids-, polyurethane foam microparticle-, and penta-BDE-Amended soils Environ. Sci. Technol. 2013, 47, 13831-13839
11. Muirhead, E. K.; Skillman, A. D.; Hook, S. E.; Schultz, I. R. Oral exposure of PBDE-47 in fish: Toxicokinetics and reproductive effects in Japanese medaka (Oryzias latipes) and fathead minnows (Pimephales promelas) Environ. Sci. Technol. 2006, 40, 523-528
12. Hooper, K.; McDonald, T. A. The PBDEs: An emerging environmental challenge and another reason for breastmilk monitoring programs Environ. Health Perspect. 2000, 108, 387-392
13. Mai, B. X.; Chen, S. J.; Luo, X. J.; Chen, L. G.; Yang, Q. S.; Sheng, G. Y.; Peng, P. G.; Fu, J. M.; Zeng, E. Y. Distribution of polybrominated diphenyl ethers in sediments of the Pearl River Delta and adjacent South China Sea Environ. Sci. Technol. 2005, 39, 3521-3527
14. Hayakawa, K.; Takatsuki, H.; Watanabe, I.; Sakai, S. Polybrominated diphenyl ethers (PBDEs), polybrominated dibenzo- p -dioxins/dibenzofurans (PBDD/Fs) and monobromo-polychlorinated dibenzo- p -dioxins/dibenzofurans (MoBPXDD/Fs) in the atmosphere and bulk deposition in Kyoto, Japan Chemosphere 2004, 57, 343-356
15. Ohta, S.; Nakao, T.; Nishimura, H.; Okumura, T.; Aozasa, O.; Miyata, H. Contamination levels of PBDEs, TBBPA, PCDDs/DFs, PBDDs/DFs and PXDDs/DFs in the environment of Japan Organohalogen Compd. 2002, 57, 57-60
16. Christensen, J. R.; MacDuffee, M.; Macdonald, R. W.; Whiticar, M.; Ross, P. S. Persistent organic pollutants in British Columbia grizzly bears: Consequence of divergent diets Environ. Sci. Technol. 2005, 39, 6952-6960
17. Thuresson, K.; Bergman, A.; Jakobsson, K. Occupational exposure to commercial decabromodiphenyl ether in workers manufacturing or handling flame-retarded rubber Environ. Sci. Technol. 2005, 39, 1980-1986
18. Zhu, W.; Liu, L.; Zou, P.; Xiao, L.; Yang, L. Y. Effect of decabromodiphenyl ether (BDE 209) on soil microbial activity and bacterial community composition World J. Microbiol. Biotechnol. 2010, 26, 1891-1899
19. Kierkegaard, A.; Balk, L.; Tjarnlund, U.; de Wit, C. A.; Jansson, B. Dietary uptake and biological effects of decabromodiphenyl ether in rainbow trout (Oncorhynchus mykiss) Environ. Sci. Technol. 1999, 33, 1612-1617
20. National Toxicology Program. Toxicology and Carcinogenesis Studies of Decabromodiphenyl Oxide (CAS No. 1163-19-5) in F344/N Rats and B6C3F1 Mice (Feed Studies); National Toxicology Program: Research Triangle Park, NC, 1986; NTP TR 309, http://ntp.niehs.nih.gov/ntp/htdocs/LT-rpts/tr309.pdf.
21. Garcia-Reyero, N.; Escalon, B. L.; Prats, E. K.; Stanley, J.; Thienpont, B.; Melby, N. L.; Barón, E.; Eljarrat, E.; Barceló, D.; Mestres, J.; Babin, P. J.; Perkins, E. J.; Raldúa, D. Effects of BDE-209 contaminated sediments on zebrafish development and potential implications to human health Environ. Int. 2014, 63, 216-223
22. Huang, H. L.; Zhang, S. Z.; Christie, P.; Wang, S.; Xie, M. Behavior of decabromodiphenyl ether (BDE-209) in the soil-plant system: Uptake, translocation, and metabolism in plants and dissipation in soil Environ. Sci. Technol. 2010, 44, 663-667
23. Eriksson, J.; Green, N.; Marsh, G.; Bergman, Å. Photochemical decomposition of 15 polybrominated diphenyl ether congeners in methanol/water Environ. Sci. Technol. 2004, 38, 3119-3125
24. Eriksson, J.; Eriksson, L.; Marsh, G.; Bergman, Å. A one step synthesis of all nona-brominated diphenyl ethers Organohalogen Compd. 2003, 61, 191-194
25. Luo, S.; Yang, S. G.; Xue, Y. G.; Liang, F.; Sun, C. Two-stage reduction/subsequent oxidation treatment of 2,2′,4,4′-tetrabromodiphenyl ether in aqueous solutions: Kinetic, pathway and toxicity J. Hazard. Mater. 2011, 192, 1795-1803
26. Rayne, S.; Ikonomou, M. G.; Whale, M. D. Anaerobic microbial and photochemical degradation of 4,4′-dibromodiphenyl ether Water Res. 2003, 37, 551-560
27. Van den Steen, E.; Covaci, A.; Jaspers, V. L. B.; Dauwe, T.; Voorspoels, S.; Eens, M.; Pinxten, R. Accumulation, tissue-specific distribution and debromination of decabromodiphenyl ether (BDE 209) in European starlings (Sturnus vulgaris) Environ. Pollut. 2007, 148, 648-653
28. European Chemicals Bureau. European Union Risk Assessment Report: Bis(pentabromophenyl) Ether; European Chemicals Bureau: Ispra, Italy, 2002; Vol. 17, 20402 EN.
29. 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
30. VI, and ozone) and non-selective oxidants (hydroxyl radical) Water Res. 2010, 44, 555-566
31. Bastos, P. M.; Eriksson, J.; Green, N.; Bergman, Å. A standardized method for assessment of oxidative transformations of brominated phenols in water Chemosphere 2008, 70, 1196-1202
32. Pang, S.-Y.; Jiang, J.; Gao, Y.; Zhou, Y.; Huangfu, X. L.; Liu, Y. Z.; Ma, J. Oxidation of flame retardant tetrabromobisphenol A by aqueous permanganate: Reaction kinetics, brominated products, and pathways Environ. Sci. Technol. 2014, 48, 615-623
33. 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
34. Hu, L. H.; 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
35. Hummers, S.; Offeman, R. Preparation of graphitic oxide J. Am. Chem. Soc. 1958, 80, 1339-1339
36. Ebert, J.; Bahadir, M. Formation of PBDD/F from flame-retarded plastic materials under thermal stress Environ. Int. 2003, 29, 711-716
37. Weber, R.; Kuch, B. Relevance of BFRs and thermal conditions on the formation pathways of brominated and brominated-chlorinated dibenzodioxins and dibenzofurans Environ. Int. 2003, 29, 699-710
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, M. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
39. Becke, A. D. Density-functional exchange-energy approximation with correct asymptotic behavior Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100
40. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785-789
41. 2 aqueous solution: Kinetics using design of experiments and mechanism by HPLC/MS/MS J. Environ. Sci. 2013, 25, 1680-1686
42. Fukui, K.; Yonezawa, T.; Shingu, H. A molecular orbital theory of reactivity in aromatic hydrocarbons J. Chem. Phys. 1952, 20, 722
43. Wang, J. T.; Wang, Y. M.; Zhang, B. S.; Hu, Q. M.; Pang, M. L. Organic Chemistry, 2 nd ed.; Nankai University Press: Tianjin, China, 2008.
44. 2 catalysts Appl. Catal., B 2008, 77, 255-263
45. Lomnicki, S.; Lichtenberger, J.; Xu, Z. T.; Waters, M.; Kosman, J.; Amiridis, M. D. Catalytic oxidation of 2,4,6-trichlorophenol over vanadia/titania-based catalysts Appl. Catal., B 2003, 46, 105-119
46. Christiansson, A.; Eriksson, J.; Teclechiel, D.; Bergman, A. Identification and quantification of products formed via photolysis of decabromodiphenyl ether Environ. Sci. Pollut. Res. Int. 2009, 16, 312-321
47. International Labor Organization (ILO). Phenols and phenolic compounds. Encyclopaedia of Occupational Health and Safety; ILO: Geneva, Switzerland, 2011; http://www.ilo.org/iloenc/part-xviii/guide-to-chemicals/item/1060-phenols-And-phenolic-compounds.
48. Choi, K. I.; Lee, S. H.; Osako, M. Leaching of brominated flame retardants from TV housing plastics in the presence of dissolved humic matter Chemosphere 2009, 74, 460-466
49. Hakk, H.; Letcher, R. J. Metabolism in the toxicokinetics and fate of brominated flame retardants-A review Environ. Int. 2003, 29, 801-828
50. Anna, M.; Heldur, H. Decabromodiphenyl ether in the rat: Absorption, distribution, metabolism, and excretion Drug Metab. Dispos. 2003, 31, 900-907
51. Yu, M.; Liu, J. Y.; Wang, T.; Sun, J. T.; Liu, R. Z.; Jiang, G. B. Metabolites of 2,4,4′-tribrominated diphenyl ether (BDE-28) in pumpkin after in vivo and in vitro exposure Environ. Sci. Technol. 2013, 47, 13494-13501
52. Orn, U.; Klasson-Wehler, E. Metabolism of 2,2′,4,4′-tetrabromodiphenyl ether in rat and mouse Xenobiotica 1998, 28, 199-211
53. Yu, Z. Q.; Zheng, K. W.; Ren, G. F.; Zheng, Y. Y.; Ma, S. T.; Peng, P. G.; Wu, M. H.; Sheng, G. Y.; Fu, J. M. Identification of hydroxylated octa- and nona-bromodiphenyl ethers in human serum from electronic waste dismantling workers Environ. Sci. Technol. 2010, 44, 3979-3985
54. Stapleton, H. M.; Alaee, M.; Letcher, R. J.; Baker, J. E. Debromination of the flame retardant decabromodiphenyl ether by juvenile carp (Cyprinus carpio) following dietary exposure Environ. Sci. Technol. 2004, 38, 112-119
55. Qiu, X. H.; Mercado-Feliciano, M.; Bigsby, R. M.; Hites, R. A. Measurement of polybrominated diphenyl ethers and metabolites in mouse plasma after exposure to a commercial pentabromo diphenyl ether mixture Environ. Health Perspect. 2007, 115, 1052-1058
56. Dingemans, M. M. L.; de Groot, A.; van Kleef, R. G. D. M.; Bergman, A.; van den Berg, M.; Vijverberg, H. P. M.; Westerink, R. H. S. Hydroxylation increases the neurotoxic potential of BDE-47 to affect exocytosis and calcium homeostatis in PC12 cells Environ. Health Perspect. 2008, 116, 637-643
57. Dzhabiev, T. S.; Denisov, N. N.; Moiseev, D. N.; Shilov, A. E. Formation of ozone during the reduction of potassium permanganate in sulfuric acid solutions Russ. J. Phys. Chem. 2005, 79, 1755-1760
58. Atkinson, R.; Aschmann, S. M. Hydroxyl radical production from the gas-phase reactions of ozone with a series of alkenes under atmospheric conditions Environ. Sci. Technol. 1993, 27, 1357-1363
59. Kaur, H.; Halliwell, B. Aromatic hydroxylation of phenylalanine as an assay for hydroxyl radicals: Measurement of hydroxyl radical formation from ozone and in blood from premature babies using improved HPLC methodology Anal. Biochem. 1994, 220, 11-15
60. Anna, M.; Heldur, H. Decabromodiphenyl ether in the rat: Absorption, distribution, metabolism, and excretion Drug Metab. Dispos. 2003, 31, 900-907
61. Kuo, Y.; Sepúlveda, M. S.; Sutton, T. M. Bioaccumulation and biotransformation of decabromodiphenyl ether and effects on daily growth in juvenile lake whitefish (Coregonus clupeaformis) Ecotoxicology 2010, 19, 751-760
62. Palm, W. U.; Raimo, K.; Wiebke, S.; Wolfgang, R.; Cornelius, Z. Photochemical reactions of brominated diphenyl ethers in organic solvents and adsorbed on silicon dioxide suspension in aqueous suspension Organohalogen Compd. 2004, 66, 4104-4109
63. Jiang, D. E.; Sumpter, B. G.; Dai, S. Unique chemical reactivity of a graphene nanoribbons zigzag edge J. Chem. Phys. 2007, 126, 134701
64. Yang, X.; Liu, H.; Hou, H. F.; Flamm, A.; Zhang, X. S.; Wang, Z. Y. Studies of thermodynamic properties and relative stability of a series of polyfluorinated dibenzo- p -dioxins by density functional theory J. Hazard. Mater. 2010, 181, 969-974
65. Yu, W. N.; Hu, J. T.; Xu, F.; Sun, X. Y.; Gao, R.; Zhang, Q. Z.; Wang, W. X. Mechanism and direct kinetics study on the homogeneous gas-phase formation of PBDD/Fs from 2-BP, 2,4-DBP, and 2,4,6-TBP as precursors Environ. Sci. Technol. 2011, 45, 1917-1925