Kinetics and quantitative structure-activity relationship study on the degradation reaction from perfluorooctanoic acid to trifluoroacetic acid

International Journal of Molecular Sciences

Volumn 15, Issue 8, 2014, Pages 14153-14165

  Gong, Chen ^a   Sun, Xiaomin ^a   Zhang, Chenxi ^a   Zhang, Xue ^a   Niu, Junfeng ^b  

^a SHANDONG UNIVERSITY   (China)

^b BEIJING NORMAL UNIVERSITY   (China)

Author keywords

Electrochemical degradation; PFOA; Quantitative structure activity relationship; Rate constants

Indexed keywords

PERFLUOROOCTANOIC ACID; TRIFLUOROACETIC ACID; FLUOROCARBON; OCTANOIC ACID DERIVATIVE;

ARTICLE; CANONICAL VARIATIONAL TRANSITION STATE THEORY; DECARBOXYLATION; DEGRADATION KINETICS; ELECTROCHEMICAL ANALYSIS; ENERGY TRANSFER; KINETICS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REACTION ANALYSIS; RICE RAMSPERGER KASSEL MARCUS THEORY; SMALL CURVATURE TUNNELING; TEMPERATURE; THERMODYNAMICS; TRANSITION STATE; CHEMISTRY; ELECTROCHEMISTRY;

CAPRYLATES; ELECTROCHEMISTRY; FLUOROCARBONS; KINETICS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TRIFLUOROACETIC ACID;

EID: 84930719114     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms150814153     Document Type: Article

References (40)

1. Hori, H.; Hayakawa, E.; Einaga, H.; Kutsuna, S.; Koike, K.; Ibusuki, T.; Kiatagawa, H.; Arakawa, R. Decomposition of environmentally persistent perfluorooctanoic acid in water by photochemical approaches. Environ. Sci. Technol. 2004, 38, 6118-6124.
2. Renner, R. Growing concern over perfluorinated chemicals. Environ. Sci. Technol. 2001, 35, 154A-160A.
3. Giesy, J.P.; Kannan, K. Global distribution of perfluorooctane sulfonate in wildlife. Environ. Sci. Technol. 2001, 35, 1339-1342.
4. Schultz, M.M.; Barofsky, D.F.; Field, J.A. Fluorinated alkyl surfactants. Environ. Eng. Sci. 2003, 20, 487-501.
5. DeWitt, J.C.; Copeland, C.B.; Strynar, M.J.; Luebke, R.W. Perfluorooctanoic acid-induced immunomodulation in adult C57BL/6J or C57BL/6N female mice. Environ. Health Perspect. 2008, 116, 644-650.
6. Lin, H.; Niu, J.; Ding, S.; Zhang, L. Electrochemical degradation of perfluorooctanoic acid (PFOA) by Ti/SnO2-Sb, Ti/SnO2-Sb/PbO2 and Ti/SnO2-Sb/MnO2 anodes. Water Res. 2012, 46, 2281-2289.
7. Loganathan, B.G.; Sajwan, K.S.; Sinclair, E.; Senthil Kumar, K.; Kannan, K. Perfluoroalkyl sulfonates and perfluorocarboxylates in two wastewater treatment facilities in Kentucky and Georgia. Water Res. 2007, 41, 4611-4620.
8. Guo, R.; Sim, W.J.; Lee, E.S.; Lee, J.H.; Oh, J.E. Evaluation of the fate of perfluoroalkyl compounds in wastewater treatment plants. Water Res. 2010, 44, 3476-3486.
9. Loos, R.; Locoro, G.; Comero, S.; Contini, S.; Schwesig, D.; Werres, F.; Balsaa, P.; Gans, O.; Weiss, S.; Blaha, L.; et al. Pan-European survey on the occurrence of selected polar organic persistent pollutants in ground water. Water Res. 2010, 44, 4115-4126.
10. Falandysz, J.; Taniyasu, S.; Gulkowska, A.; Yamashita, N.; Schulte-Oehlmann, U. Is fish a major source of fluorinated surfactants and repellents in humans living on the Baltic Coast? Environ. Sci. Technol. 2006, 40, 748-751.
11. Keller, J.M.; Kannan, K.; Taniyasu, S.; Yamashita, N.; Day, R.D.; Arendt, M.D.; Segars, A.L.; Kucklick, J.R. Perfluorinated compounds in the plasma of loggerhead and Kemp's ridley sea turtles from the southeastern coast of the United States. Environ. Sci. Technol. 2005, 39, 9101-9108.
12. Moriwaki, H.; Takagi, Y.; Tanaka, M.; Tsuruho, K.; Okitsu, K.; Maeda, Y. Sonochemical decomposition of perfluorooctane sulfonate and perfluorooctanoic acid. Environ. Sci. Technol. 2005, 39, 3388-3392.
13. Berthiaume, J.; Wallace, K.B. Perfluorooctanoate, perflourooctanesulfonate, and N-ethyl perfluorooctanesulfonamido ethanol; peroxisome proliferation and mitochondrial biogenesis. Toxicol. Lett. 2002, 129, 23-32.
14. Olsen, G.W.; Logan, P.W.; Hansen, K.J.; Simpson, C.A.; Burris, J.M.; Burlew, M.M.; Vorarath, P.P.; Venkateswarlu, P.; Schumpert, J.C.; Mandel, J.H. An occupational exposure assessment of a perfluorooctanesulfonyl fluoride production site: Biomonitoring. AIHA J. 2003, 64, 651-659.
15. Sanderson, H.; Boudreau, T.M.; Mabury, S.A.; Cheong, W.J.; Solomon, K.R. Ecological impact and environmental fate of perfluorooctane sulfonate on the zooplankton community in indoor microcosms. Environ. Toxicol. Chem. 2002, 21, 1490-1496.
16. Hines, E.P.; White, S.S.; Stanko, J.P.; Gibbs-Flournoy, E.A.; Lau, C.; Fenton, S.E. Phenotypic dichotomy following developmental exposure to perfluorooctanoic acid (PFOA) in female CD-1 mice: Low doses induce elevated serum leptin and insulin, and overweight in mid-life. Mol. Cell. Endocrinol. 2009, 304, 97-105.
17. Kennedy, G.L.; Butenhoff, J.L.; Olsen, G.W.; O'Connor, J.C.; Seacat, A.M.; Perkins, R.G.; Biegel, L.B.; Murphy, S.R.; Farrar, D.G. The toxicology of perfluorooctanoate. Crit. Rev. Toxicol. 2004, 34, 351-384.
18. Lau, C.; Anitole, K.; Hodes, C.; Lai, D.; Pfahles-Hutchens, A.; Seed, J. Perfluoroalkyl acids: A review of monitoring and toxicological findings. J. Toxicol. Sci. 2007, 99, 366-394.
19. US EPA. Revised Draft Hazard Assessment of Perfluorooctanoic Acid and Its Salts. Available online: http://www.fluoridealert.org/wp-content/pesticides/pfoa.epa.nov.4.2002.pdf (accessed on 4 November 2002).
20. Järnberg, U.; Holmström, K.; van Bavel, B. Perfluoroalkylated Acids and Related Compounds (PFAS) in the Swedish Environment-Chemistry. Available online http://www.diva-portal.org/smash/ get/diva2:657980/FULLTEXT01.pdf (accessed on 1 May 2007).
21. Hoffman, K.; Webster, T.F.; Bartell, S.M.; Weisskopf, M.G.; Fletcher, T.; Vieira, V.M. Private drinking water wells as a source of exposure to perfluorooctanoic acid (PFOA) in communities surrounding a fluoropolymer production facility. Environ. Health Perspect. 2011, 119, 92-97.
22. Ochiai, T.; Moriyama, H.; Nakata, K.; Murakami, T.; Koide, Y.; Fujishima, A. Electrochemical and photocatalytic decomposition of perfluorooctanoic acid with a hybrid reactor using a boron-doped diamond electrode and TiO2 photocatalyst. Chem. Lett. 2011, 40, 682-683.
23. Zhuo, Q.; Deng, S.; Yang, B.; Huang, J.; Yu, G. Efficient electrochemical oxidation of perfluorooctanoate using a Ti/SnO2-Sb-Bi anode. Environ. Sci. Technol. 2011, 45, 2973-2979.
24. Ochiai, T.; Lizuka, Y.; Nakata, K.; Murakami, T.; Tryk, D.A.; Fujishima, A.; Koide, Y.; Morito, Y. Efficient electrochemical decomposition of perfluorocarboxylic acids by the use of a boron-doped diamond electrode. Diam. Relat. Mater. 2011, 20, 64-67.
25. Niu, J.; Lin, H.; Gong, C.; Sun, X. Theoretical and experimental insights into the electrochemical mineralization mechanism of perfluorooctanoic acid. Environ. Sci. Technol. 2013, 47, 14341-14349.
26. Niu, J.; Lin, H.; Xu, J.; Wu, H.; Li, Y. Electrochemical mineralization of perfluorocarboxylic acids (PFCAs) by Ce-doped modified porous nanocrystalline PbO2 film electrode. Environ. Sci. Technol. 2012, 46, 10191-10198.
27. Zhang, Q.; Zhang, R.; Gu, Y. Kinetics and mechanism of O (3P) reaction with CH3CHF2: A theoretical study. J. Phys. Chem. A 2004, 108, 1064-1068.
28. Zhang, Q.; Zhang, R.; Chan, K.; Bello, I. Ab initio and variational transition state approach to β-C3N4 formation: Kinetics for the reaction of CH3NH2 with H. J. Phys. Chem. A 2005, 109, 9112-9117.
29. Sun, T.; Zhang, Q.; Qu, X.; Wang, W. Mechanism and direct dynamics studies for the reaction of monoethylsilane EtSiH3 with atomic O (3P). Chem. Phys. Lett. 2005, 407, 527-532.
30. Zhao, Y.; Truhlar, D.G. Hybrid meta density functional theory methods for thermochemistry, thermochemical kinetics, and noncovalent interactions: The MPW1B95 and MPWB1K models and comparative assessments for hydrogen bonding and van der Waals interactions. J. Phys. Chem. A 2004, 108, 6908-6918.
31. Hehre, W.; Ditchfield, R.; Pople, J. Theoretical investigations on the solvation process. J. Chem. Phys. 1972, 56, 2557-2562.
32. Zheng, J.J.; Zhao, Y.; Truhlar, D.G. The DBH24/08 database and its use to assess electronic structure model chemistries for chemical reaction barrier heights. J. Chem. Theory Comput. 2009, 5, 808-821.
33. Frisch, M.; Trucks, G.; Schlegel, H.; Scuseria, G.; Robb, M.; Cheeseman, J.; Zakrzewski, V.; Montgomery, J., Jr.; Stratmann, R.; Burant, J.; et al. Gaussian 03, Revision E.01. Available online: http://www.gaussian.com/g_misc/g03/citation_g03.htm (accessed on 11 June 2003).
34. Corchado, J.C.; Chuang, Y.Y.; Fast, P.L.; Hu, W.P.; Liu, Y.P.; Lynch, G.C.; Nguyen, K.A.; Jackels, C.F.; Fernandez Ramos, A.; Ellingson, B.A.; et al. POLYRATE Version 9.7; University of Minnesota: Minneapolis, MN, USA, 2007.
35. Miller, W.H. Tunneling corrections to unimolecular rate constants, with application to formaldehyde. J. Am. Chem. Soc. 1979, 101, 6810-6814.
36. Zhang, Q.; Yu, W.; Zhang, R.; Zhou, Q.; Gao, R.; Wang, W. Quantum chemical and kinetic study on dioxin formation from the 2, 4, 6-TCP and 2, 4-DCP precursors. Environ. Sci. Technol. 2010, 44, 3395-3403.
37. Qu, X.; Wang, H.; Zhang, Q.; Shi, X.; Xu, F.; Wang, W. Mechanistic and kinetic studies on the homogeneous gas-phase formation of PCDD/Fs from 2, 4, 5-trichlorophenol. Environ. Sci. Technol. 2009, 43, 4068-4075.
38. Gong, C.; Sun, X.; Zhang, C. The atmospheric chemical reaction of 4-tert-butylphenol initiated by OH radicals. Environ. Chem. 2013, 10, 111-119.
39. Hou, H.; Wang, B. Ab initio study of the reaction of propionyl (C2H5CO) radical with oxygen (O2). J. Chem. Phys. 2007, 127, 054306.
40. Rogers, D.; Hopfinger, A.J. Application of genetic function approximation to quantitative structure-activity relationships and quantitative structure-property relationships. J. Chem. Inf. Comput. Sci. 1994, 34, 854-866.