Debromination of polybrominated diphenyl ethers by nanoscale zerovalent iron: Pathways, kinetics, and reactivity

Environmental Science and Technology

Volumn 44, Issue 21, 2010, Pages 8236-8242

  Zhuang, Yuan ^a   Ahn, Sungwoo ^a   Luthy, Richard G ^a  

^a Stanford University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED COMPOUNDS; CORRESPONDING COMPOUNDS; DEBROMINATE; DEBROMINATION; DEGRADATION PATHWAYS; DESCRIPTORS; DIPHENYL ETHER; HEAT OF FORMATION; LOWEST UNOCCUPIED MOLECULAR ORBITAL; MULTI-STEP; NANOSCALE ZERO-VALENT IRON; PHENYL RINGS; POLYBROMINATED DIPHENYL ETHERS; PSEUDO-FIRST-ORDER REACTION; REACTION PROCESS; RELATIVE REACTION RATES;

BROMINE; DEGRADATION; ETHERS; MOLECULAR ORBITALS; NANOSTRUCTURED MATERIALS; ORGANIC COMPOUNDS; POLYACRYLATES; RATE CONSTANTS; THERMOCHEMISTRY;

REACTION KINETICS;

2,3,4 TRIBROMODIPHENYL ETHER; BROMINE; DIPHENYL ETHER; IRON; POLYBROMINATED DIPHENYL ETHER; UNCLASSIFIED DRUG;

BROMINE; DEGRADATION; IRON; PBDE; REACTION KINETICS;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DEBROMINATION; DEGRADATION KINETICS; NANOANALYSIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ENVIRONMENTAL POLLUTANTS; ENVIRONMENTAL REMEDIATION; FLAME RETARDANTS; HALOGENATED DIPHENYL ETHERS; HALOGENATION; IRON; KINETICS; METAL NANOPARTICLES;

EID: 78549256820     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es101601s     Document Type: Article

References (41)

1. Alaee, M.; Arias, P.; Sjodin, A.; Bergman, A. An overview of commercially used brominated flame retardants, their applications, their use patterns in different countries/regions and possible modes of release. Environ. Int. 2003, 29(6), 683-689.
2. Hites, R. A. Polybrominated diphenyl ethers in the environment and in people: A meta-analysis of concentrations. Environ. Sci. Technol. 2004, 38(4), 945-956.
3. Hale, R. C.; Alaee, M.; Manchester-Neesvig, J. B.; Stapleton, H. M.; Ikonomou, M. G. Polybrominated diphenyl ether flame retardants in the North American environment. Environ. Int. 2003, 29(6), 771-779.
4. Sellstrom, U.; De Wit, C. A.; Lundgren, N.; Tysklind, M. Effect of sewage-sludge application on concentrations of higherbrominated diphenyl ethers in soils and earthworms. Environ. Sci. Technol. 2005, 39(23), 9064-9070.
5. Ciparis, S.; Hale, R. C. Bioavailability of polybrominated diphenyl ether flame retardants in biosolids and spiked sediment to the aquatic oligochaete, Lumbriculus variegatus. Environ. Toxicol. Chem. 2005, 24(4), 916-925.
6. U. S. Department of Health and Human Services, Public Health Service Agency for Toxic Substances and Disease Registry. Toxicological Profile for Polybrominated Biphenyls and Polybrominated Diphenyl Ethers (PBBs and PBDEs); ATSDR: Atlanta, GA, 2004.
7. Li, X. Q.; Elliott, D. W.; Zhang, W. X. Zero-valent iron nanoparticles for abatement of environmental pollutants: Materials and engineering aspects. Crit. Rev. Solid State Mater. Sci. 2006, 31(4), 111-122.
8. Li, A.; Tai, C.; Zhao, Z. S.; Wang, Y. W.; Zhang, Q. H.; Jiang, G. B.; Hu, J. T. Debromination of decabrominated diphenyl ether by resin-bound iron nanoparticles. Environ. Sci. Technol. 2007, 41(19), 6841-6846.
9. Shih, Y. H.; Tai, Y. T. Reaction of decabrominated diphenyl ether by zerovalent iron nanoplarticles. Chemosphere 2010, 78(10), 1200-1206.
10. Keum, Y. S.; Li, Q. X. Reductive debromination of polybrominated diphenyl ethers byzerovalent iron. Environ. Sci. Technol. 2005, 39(7), 2280-2286.
11. Liu, Y. Q.; Majetich, S. A.; Tilton, R. D.; Sholl, D. S.; Lowry, G. V. TCE dechlorination rates, pathways, and efficiency of nanoscale iron particles with different properties. Environ. Sci. Technol. 2005, 39(5), 1338-1345.
12. Nurmi, J. T.; Tratnyek, P. G.; Sarathy, V.; Baer, D. R.; Amonette, J. E.; Pecher, K.; Wang, C. M.; Linehan, J. C.; Matson, D. W.; Penn, R. L.; et al. Characterization and properties of metallic iron nanoparticles: Spectroscopy, electrochemistry, and kinetics. Environ. Sci. Technol. 2005, 39(5), 1221-1230.
13. Schrick, B.; Blough, J. L.; Jones, A. D.; Mallouk, T. E. Hydrodechlorination of trichloroethylene to hydrocarbons using bimetallic nickel-iron nanoparticles. Chem. Mater. 2002, 14(12), 5140-5147.
14. Lowry, G. V.; Johnson, K. M. Congener-specific dechlorination of dissolved PCBs by microscale and nanoscale zerovalent iron in a water/methanol solution. Environ. Sci. Technol. 2004, 38(19), 5208-5216.
15. Sun, Y. P.; Li, X. Q.; Zhang, W. X.; Wang, H. P. A method for the preparation of stable dispersion of zero-valent iron nanoparticles. Colloid Surf., A 2007, 308 (1-3), 60-66.
16. Zhu, B. W.; Lim, T. T. Catalytic reduction of chlorobenzenes with Pd/Fe nanoparticles: Reactive sites, catalyst stability, particle aging, and regeneration. Environ. Sci. Technol. 2007, 41(21), 7523-7529.
17. Wang, C. B.; Zhang, W. X. Synthesizing nanoscale iron particles forrapidand complete dechlorination of TCE and PCBs. Environ. Sci. Technol. 1997, 31(7), 2154-2156.
18. Wang, Q.; Snyder, S.; Kim, J.; Choi, H. Aqueous ethanol modified nanoscale zerovalent iron in bromate reduction: Synthesis, characterization, and reactivity. Environ. Sci. Technol. 2009, 43(9), 3292-3299.
19. Ponder, S. M.; Darab, J. G.; Mallouk, T. E. Remediation of Cr (VI) and Pb (II) aqueous solutions using supported, nanoscale zerovalent iron. Environ. Sci. Technol. 2000, 34(12), 2564-2569.
20. Yak, H. K.; Wenclawiak, B. W.; Cheng, I. F.; Doyle, J. G.; Wai, C. M. Reductive dechlorination of polychlorinated biphenyls by zerovalent iron in subcritical water. Environ. Sci. Technol. 1999, 33(8), 1307-1310.
21. 0 particles supported on chitosan and silica. Chemosphere 2006, 65(7), 1137-1145.
22. Kim, Y. H.; Shin, W. S.; Ko, S. O. Reductive dechlorination of chlorinated biphenyls by palladized zero-valent metals. J. Environ. Sci. Health, A 2004, 39(5), 1177-1188.
23. Zeng, X.; Freeman, P. K.; Vasil'ev, Y. V.; Voinov, V. G.; Simonich, S. L.; Barofsky, D. F. Theoretical calculation of thermodynamic properties of polybrominated diphenyl ethers. J. Chem. Eng. Data 2005, 50(5), 1548-1556.
24. Rayne, S.; Ikonomou, M. G.; Whale, M. D. Anaerobic microbial and photochemical degradation of 4, 4′-dibromodiphenyl ether. Water Res. 2003, 37(3), 551-560.
25. Hakk, H.; Letcher, R. J. Metabolism in the toxicokinetics and fate of brominated flame retardants - a review. Environ. Int. 2003, 29(6), 801-828.
26. Eriksson, J.; Green, N.; Marsh, G.; Bergman, A. Photochemical decomposition of 15 polybrominated diphenyl ether congeners in methanol/water. Environ. Sci. Technol. 2004, 38(11), 3119-3125.
27. Haga, N.; Takayanagi, H. Mechanisms of the photochemical rearrangement of diphenyl ethers. J. Org. Chem. 1996, 61(2), 735-745.
28. Joo, S. H.; Feitz, A. J.; Waite, T. D. Oxidative degradation of the carbothioate herbicide, molinate, using nanoscale zero-valent iron. Environ. Sci. Technol. 2004, 38(7), 2242-2247.
29. Buser, H. R.; Rappe, C. Formation of polychlorinated dibenzofurans (PCDFs) from the pyrolysis of individual PCB isomers. Chemosphere 1979, 8(3), 157-174.
30. Minkin, V. I.; Mikhailov, I. E.; Dushenko, G. A.; Yudilevich, J. A.; Minyaev, R. M.; Zschunke, A.; Mugge, K. 1, 5-Sigmatropic Shifts of Bromine over a Cyclopentadiene Ring. J. Phys. Org. Chem. 1991, 4(1), 31-47.
31. Kamei, I.; Kogura, R.; Kondo, R. Metabolism of 4, 4′- dichlorobiphenyl bywhite-rot fungi Phanerochaete chrysosporium and Phanerochaete sp MZ142. Appl. Microbiol. Biotechnol. 2006, 72(3), 566-575.
32. Liu, J.; Hu, D. F.; Jiang, G.; Schnoor, J. L. In vivo biotransformation of 3, 3, 4, 4-tetrachlorobiphenyl by whole plants-Poplars and switchgrass. Environ. Sci. Technol. 2009, 43(19), 7503-7509.
33. Yak, H. K.; Lang, Q. Y.; Wai, C. M. Relative resistance of positional isomers of polychlorinated biphenyls toward reductive dechlorination by zerovalent iron in subcritical water. Environ. Sci. Technol. 2000, 34(13), 2792-2798.
34. Fu, Q. S.; Barkovskii, A. L.; Adriaens, P. Reductive transformation of dioxins: An assessment of the contribution of dissolved organic matter to dechlorination reactions. Environ. Sci. Technol. 1999, 33(21), 3837-3842.
35. Scherer, M. M.; Balko, B. A.; Gallagher, D. A.; Tratnyek, P. G. Correlation analysis of rate constants for dechlorination by zerovalent iron. Environ. Sci. Technol. 1998, 32(19), 3026-3033.
36. Liu, Y. Q.; Choi, H.; Dionysiou, D.; Lowry, G. V. Trichloroethene hydrodechlorination in water by highly disordered monometallic nanoiron. Chem. Mater. 2005, 17(21), 5315-5322.
37. Sohn, K.; Kang, S. W.; Ahn, S.; Woo, M.; Yang, S. K. Fe (0) nanoparticles for nitrate reduction: Stability, reactivity, and transformation. Environ. Sci. Technol. 2006, 40(17), 5514-5519.
38. 2 evolution and TCE dechlorination. Environ. Sci. Technol. 2006, 40(19), 6085-6090.
39. Hu, J. W.; Eriksson, L.; Bergman, A.; Jakobsson, E.; Kolehmainen, E.; Knuutinen, J.; Suontamo, R.; Wei, X. H. Molecular orbital studies on brominated diphenyl ethers. Part II - reactivity and quantitative structure-activity (property) relationships. Chemosphere 2005, 59(7), 1043-1057.
40. Zhao, Y. Y.; Tao, F. M.; Zeng, E. Y. Theoretical study on the chemical properties of polybrominated diphenyl ethers. Chemosphere 2008, 70(5), 901-907.
41. Karelson, M.; Lobanov, V. S.; Katritzky, A. R. Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev. 1996, 96(3), 1027-1043.