Global emission inventories for C4–C14 perfluoroalkyl carboxylic acid (PFCA) homologues from 1951 to 2030, part II: The remaining pieces of the puzzle

Environment International - Tập 69 - Trang 166-176 - 2014
Zhanyun Wang1, Ian T. Cousins2, Martin Scheringer1, Robert C. Buck3, Konrad Hungerbühler1
1Institute for Chemical and Bioengineering, ETH Zurich, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich, Switzerland
2Department of Applied Environmental Science (ITM), Stockholm University, SE-10691 Stockholm, Sweden
3E.I. du Pont de Nemours & Co. Inc., DuPont Chemicals and Fluoroproducts, 974 Centre Road, CRP 702-2211B, Wilmington, DE 19880-0702, USA

Tài liệu tham khảo

3M, 2000, Letter to US EPA Re: phase-out plan for POSF-based products (226-0600), 226, 1 3M, 2000, Voluntary use and exposure information profile: perfluorodecane sulfonate (226-0579), 226, 1 3M, 2000, Voluntary use and exposure information profile: perfluorooctanoic acid and salts (AR226-0595), 226, 1 3M, 2003, Letter to US EPA Re: environmental health and safety measures relating to perfluorooctanoic acid and its salts (PFOA) (226-1303), 226, 1 3M, 2008, 1 Ahrens, 2011, Wastewater treatment plant and landfills as sources of polyfluoroalkyl compounds to the atmosphere, Environ Sci Technol, 45, 8098, 10.1021/es1036173 Armitage, 2006, Modeling global-scale fate and transport of perfluorooctanoate emitted from direct sources, Environ Sci Technol, 40, 6969, 10.1021/es0614870 Armitage, 2009, Modeling the global fate and transport of perfluorooctanoic acid (PFOA) and perfluorooctanoate (PFO) emitted from direct sources using a multispecies mass balance model, Environ Sci Technol, 43, 1134, 10.1021/es802900n Armitage, 2009, Comparative assessment of the global fate and transport pathways of long-chain perfluorocarboxylic acids (PFCAs) and perfluorocarboxylates (PFCs) emitted from direct sources, Environ Sci Technol, 43, 5830, 10.1021/es900753y Asahi Atkinson, 1986, Kinetics and mechanisms of the gas-phase reactions of the hydroxyl radical with organic compounds under atmospheric conditions, Chem Rev, 86, 69, 10.1021/cr00071a004 Banks, 1994 Benskin, 2011, Source elucidation of perfluorinated carboxylic acids in remote alpine lake sediment cores, Environ Sci Technol, 45, 7188, 10.1021/es2011176 Benskin, 2012, Per- and polyfluoroalkyl substances in landfill leachate: patterns time trends and sources, Environ Sci Technol, 46, 11532, 10.1021/es302471n Bravo, 2010, Atmospheric chemistry of C4F9OC2H5 (HFE-7200) C4F9OCH3 (HFE-7100) C3F7OCH3 (HFE-7000) and C3F7CH2OH: temperature dependence of the kinetics of their reactions with OH radicals atmospheric lifetimes and global warming potentials, Phys Chem Chem Phys, 12, 5115, 10.1039/b923092k Broniatowski, 2008, Semifluorinated alkanes — primitive surfactants of fascinating properties, Adv Colloid Interf Sci, 138, 63, 10.1016/j.cis.2007.11.002 Bryce, 1964, Industrial and utilitarian aspects of fluorine chemistry, vol. V, 297 Buck, 2011, Perfluoroalkyl and polyfluoroalkyl substances in the environment: terminology classification and origins, Integr Environ Assess Manag, 7, 513, 10.1002/ieam.258 Busch, 2010, Polyfluoroalkyl compounds in landfill leachates, Environ Pollut, 158, 1467, 10.1016/j.envpol.2009.12.031 Carr, 2003, A kinetic and mechanistic study of the gas-phase reactions of OH radicals and Cl atoms with some halogenated acetones and their atmospheric implications, Phys Chem Chem Phys, 5, 3874, 10.1039/b304298g Cavalli, 1998, Atmospheric lifetimes infrared spectra and degradation products of a series of hydrofluoroethers, Atmos Environ, 32, 3767, 10.1016/S1352-2310(98)00106-X Chen, 2004, Rate constants for the gas‐phase reaction of CF3CF2CF2CF2CF2CHF2 with OH radicals at 250–430K, Int J Chem Kinet, 36, 26, 10.1002/kin.10170 Chen, 2011, Kinetics and mechanism of gas-phase reaction of CF3CF2CF2CF2CF2CF2CF2CF2H with OH radicals in an environmental reaction chamber at 253–328K, Chem Phys Lett, 501, 263, 10.1016/j.cplett.2010.12.009 Chen, 2011, Kinetics and mechanism of gas-phase reactions of n-C4F9OCH3 i-C4F9OCH3 n-C4F9OC(O)H and i-C4F9OC(O)H with OH radicals in an environmental reaction chamber at 253–328K, Chem Phys Lett, 514, 207, 10.1016/j.cplett.2011.08.049 Christensen, 1998, Atmospheric chemistry of HFE-7200 (C4F9OC2H5): reaction with OH radicals and fate of C4F9OCH2CH2O() and C4F9OCHO()CH3 radicals, J Phys Chem A, 102, 4839, 10.1021/jp981128u Clara, 2008, Emissions of perfluorinated alkylated substances (PFAS) from point sources — identification of relevant branches, Water Sci Technol, 58, 59, 10.2166/wst.2008.641 Coenders, 1992 Conder, 2008, Are PFCAs bioaccumulative? A critical review and comparison with regulatory criteria and persistent lipophilic compounds, Environ Sci Technol, 42, 995, 10.1021/es070895g Cousins, 2011, Reconciling measurement and modelling studies of the sources and fate of perfluorinated carboxylates, Environ Chem, 8, 339, 10.1071/EN10144 Dauchy, 2012, Relationship between industrial discharges and contamination of raw water resources by perfluorinated compounds. Part I: case study of a fluoropolymer manufacturing plant, Bull Environ Contam Toxicol, 89, 525, 10.1007/s00128-012-0704-x De Silva, 2009, Distribution of perfluorocarboxylate isomers in select samples from the North American environment, Environ Toxicol Chem, 28, 1801, 10.1897/08-500.1 Duncan, 2003 DuPont, 2007, 1 DuPont, 2008, 1 Dyneon ECHA (European Chemical Agency) ECHA (European Chemical Agency) Ellis, 2001, Thermolysis of fluoropolymers as a potential source of halogenated organic acids in the environment, Nature, 412, 321, 10.1038/35085548 Ellis, 2004, Degradation of fluorotelomer alcohols: a likely atmospheric source of perfluorinated carboxylic acids, Environ Sci Technol, 38, 3316, 10.1021/es049860w EU Commission (European Commission) Fielding, 1979, Chapter 11. Organofluorine surfactants and textile chemicals Filella, 2006, Daily weekly and seasonal relationships among VOCs NOx and O3 in a semi-urban area near Barcelona, J Atmos Chem, 54, 189, 10.1007/s10874-006-9032-z Fluoron, 2014 FMG, 2002, Presentation to EPA (226-1094), 226, 1 Francen VL. Patent: Surface film former to retard evaporation and extinguish hydrocarbon fires. US 1264681, 1972. Freberg, 2010, Occupational exposure to airborne perfluorinated compounds during professional ski waxing, Environ Sci Technol, 44, 7723, 10.1021/es102033k Frömel, 2010, Biodegradation of fluorinated alkyl substances, Rev Environ Contam Toxicol, 208, 161 Fuxin (Fuxin Heng Tong Fluorine Chemicals Co. Ltd) García, 2007, Products obtained in the fuel-rich combustion of PTFE at high temperature, J Anal Appl Pyrolysis, 80, 85, 10.1016/j.jaap.2007.01.004 Gebbink, 2013, Polyfluoroalkyl phosphate esters and perfluoroalkyl carboxylic acids in target food samples and packaging-method development and screening, Environ Sci Pollut Res, 20, 7949, 10.1007/s11356-013-1596-y Giesy, 2001, Global distribution of perfluorooctane sulfonate in wildlife, Environ Sci Technol, 35, 1339, 10.1021/es001834k Goto, 2002, Atmospheric chemistry of HFE-7500 [n-C3F7CF(OC2H5)CF(CF3)2]: reaction with OH radicals and Cl atoms and atmospheric fate of n-C3F7CF(OCHO)CF(CF3)2 and n-C3F7CF(OCH2CH2O)CF(CF3)2 radicals, Environ Sci Technol, 36, 2395, 10.1021/es0113798 Gramstad, 1957, 512. Perfluoroalkyl derivatives of sulphur. Part VI. Perfluoroalkanesulphonic acids CF3[CF2]nSO3H (n=1–7), J Chem Soc, 2640, 10.1039/JR9570002640 Holzapfel, 1966, Uses of fluorinated surfactants, Fette Seifen Anstrichmittel, 68, 837 Huang, 2010, Electro fluorination and its fine-fluorine production branches, Chem Prod Technol, 17, 1 Hurley, 2004, Atmospheric chemistry of fluorinated alcohols: reaction with Cl atoms and OH radicals and atmospheric lifetimes, J Phys Chem A, 108, 1973, 10.1021/jp0373088 Hurley, 2006, Atmospheric chemistry of n-CxF2x+1CHO (x=1, 2, 3, 4): fate of n-CxF2x+1C(O) radicals, J Phys Chem A, 110, 12443, 10.1021/jp064029m Huset, 2011, Quantitative determination of fluorochemicals in municipal landfill leachates, Chemosphere, 82, 1380, 10.1016/j.chemosphere.2010.11.072 Husted DR, Ahlbrecht AH. Patent: Fluorinated alcohols and acetate esters. US 2666797, 1954. Imbalzano, 1991, Combat corrosion with fluoroplastics and fluoroelastomers, Chem Eng Prog, 87, 69 Iwai, 2011, Toxicokinetics of ammonium perfluorohexanoate, Drug Chem Toxicol, 34, 341, 10.3109/01480545.2011.585162 Jackson, 2013, Polyfluorinated amides as a historical PFCA source by electrochemical fluorination of alkyl sulfonyl fluorides, Environ Sci Technol, 47, 382, 10.1021/es303152m Jackson, 2011, Atmospheric degradation of perfluoro-2-methyl-3-pentanone: photolysis hydrolysis and hydration, Environ Sci Technol, 45, 8030, 10.1021/es104362g Jackson, 2013, Atmospheric oxidation of polyfluorinated amides: historical source of perfluorinated carboxylic acids to the environment, Environ Sci Technol, 47, 4317, 10.1021/es400617v Kirk-Othmer, 2000 Kishikawa Y, Hashigaya A, Shibata N, Otsuka T. Patent: Industrial-scale manufacture of fluorocarboxylic acids esters and salts via fluorosulfinate salts. JP 2009040708, 2009. Krafft, 2009, Chemistry physical chemistry and uses of molecular fluorocarbon–hydrocarbon diblocks triblocks and related compounds—unique “apolar” components for self-assembled colloid and interface engineering, Chem Rev, 109, 1714, 10.1021/cr800260k Larsen, 2006, Method development for the determination of residual fluorotelomer raw materials and perfluorooctanoate in fluorotelomer-based products by gas chromatography and liquid chromatography mass spectrometry, J Chromatogr A, 1110, 117, 10.1016/j.chroma.2006.01.086 Lewis, 1947, Pyrolysis of polytetrafluoroethylene, J Am Chem Soc, 69, 1968, 10.1021/ja01200a039 Martin, 2010, PFOS or PreFOS? Are perfluorooctane sulfonate precursors (PreFOS) important determinants of human and environmental perfluorooctane sulfonate (PFOS) exposure?, J Environ Monit, 12, 1979, 10.1039/c0em00295j Matsuoka Y, Watanabe K, Kamiya K. Patent: Method for producing fluoropolymer using fluorocarboxylic acid compound. US 2010/0029878 A1, 2010. Millet G.H. Re: fluoropolymer incineration ECA; letter to Mr. Jim Willis US EPA (EPA-HQ-OPPT-2003-0071-0164); US EPA e-Docket 2005. Missio, 2010, Access to poly-fluorinated building blocks via electrochemical fluorination, 1 Miteni Möller, 2010, Distribution and sources of polyfluoroalkyl substances (PFAS) in the River Rhine watershed, Environ Pollut, 158, 3243, 10.1016/j.envpol.2010.07.019 Newsted, 2002, Predicted distribution and ecological risk assessment of a “segregated” hydrofluoroether in the Japanese environment, Environ Sci Technol, 36, 4761, 10.1021/es0257321 NICNAS, 2006 Nielsen, 1994, Atmospheric chemistry of HFC-143a: spectrokinetic investigation of the CF3CH2O2 radical its reactions with NO and NO2 and the fate of CF3CH2O, J Phys Chem, 98, 9518, 10.1021/j100089a026 OECD, 2009, 1 Olsen, 2003, Perfluorooctanesulfonate and other fluorochemicals in the serum of American Red Cross adult blood donors, Environ Health Perspect, 111, 1892, 10.1289/ehp.6316 Orkin, 1997, Rate constants for the reactions of OH with HFC-245cb (CH3CF2CF3) and some fluoroalkenes (CH2CHCF3, CH2CFCF3, CF2CFCF3, and CF2CF2), J Phys Chem A, 101, 9118, 10.1021/jp971994r Oyaro, 2003, Kinetic study of the OH reaction with the hydrofluoroethers C4F9OCH3 and C4F9OC2H5 by the relative rate method, Asian Chem Lett, 7, 119 Parsons, 2008, de Biodegradation of perfluorinated compounds, Rev Environ Contam Toxicol, 196, 53 Philips, 1957, The application of fluorochemicals to cotton fabrics to obtain oil and water repellent surfaces, Text Res J, 27, 369, 10.1177/004051755702700505 Picó, 2011, Perfluorinated compounds in food: a global perspective, Crit Rev Food Sci Nutr, 51, 605, 10.1080/10408391003721727 Place, 2012, Identification of novel fluorochemicals in aqueous film-forming foams used by the US military, Environ Sci Technol, 46, 7120, 10.1021/es301465n Plassmann, 2010, Trace analytical methods for semifluorinated n-alkanes in snow soil and air, Anal Chem, 82, 4551, 10.1021/ac1005519 Plassmann, 2011, Environmental occurrence and fate of semifluorinated n-alkanes in snow and soil samples from a ski area, Chemosphere, 85, 1458, 10.1016/j.chemosphere.2011.08.028 Prevedouros, 2006, Sources, fate and transport of perfluorocarboxylates, Environ Sci Technol, 40, 32, 10.1021/es0512475 Rattigan, 1994, Photochemical studies of 1,1,1,2 tetrafluoroethane (HFC 134a), J Chem Soc Faraday Trans, 90, 1819, 10.1039/ft9949001819 Rayne, 2009, Perfluoroalkyl sulfonic and carboxylic acids: a critical review of physicochemical properties levels and patterns in waters and wastewaters and treatment methods, J Environ Sci Health A Tox Hazard Subst Environ Eng, 44, 1145, 10.1080/10934520903139811 Russell, 2008, Investigation of the biodegradation potential of a fluoroacrylate polymer product in aerobic soils, Environ Sci Technol, 42, 800, 10.1021/es0710499 Russell, 2010, Evaluation of PFO formation from the biodegradation of a fluorotelomer-based urethane polymer product in aerobic soils, Polym Degrad Stab, 95, 79, 10.1016/j.polymdegradstab.2009.10.004 Russell, 2010, Comment on “degradability of an acrylate-linked fluorotelomer polymer in soil”, Environ Sci Technol, 44, 848, 10.1021/es902348w Schenker, 2008, Contribution of volatile precursor substances to the flux of perfluorooctanoate to the Arctic, Environ Sci Technol, 42, 3710, 10.1021/es703165m Scherer, 1970, vol. 14/2, 127 Seacat, 2004 Segal, 1958, Oil and water repellent treatments for cotton with fluorochemicals, Text Res J, 28, 233, 10.1177/004051755802800308 Sekiya, 2006, Evaluation and selection of CFC alternatives, Adv Flourine Sci, 1, 33, 10.1016/S1872-0358(06)01002-5 Simon, 1998, Chemical recycling of polytetrafluoroethylene by pyrolysis, Polym Degrad Stab, 62, 1, 10.1016/S0141-3910(97)00097-9 Sölch, 2012 Stemmler, 2010, Pathways of PFOA to the Arctic: variabilities and contributions of oceanic currents and atmospheric transport and chemistry sources, Atmos Chem Phys Discuss, 10, 11577 Sundström, 2012, Comparative pharmacokinetics of perfluorohexanesulfonate (PFHxS) in rats mice and monkeys, Reprod Toxicol, 33, 441, 10.1016/j.reprotox.2011.07.004 Taylor, 2009, 1 Telomer Research Program, 2002, Update presented to US EPA on 25 November 2002 (226-1141), 226, 1 Telomer Research Program, 2003 Tsai, 2005, An overview of environmental hazards and exposure risk of hydrofluorocarbons (HFCs), Chemosphere, 61, 1539, 10.1016/j.chemosphere.2005.03.084 Tsai, 2005, Environmental risk assessment of hydrofluoroethers (HFEs), J Hazard Mater, 119, 69, 10.1016/j.jhazmat.2004.12.018 Tsai, 2009, Environmental hazards and health risk of common liquid perfluoro-n-alkanes potent greenhouse gases, Environ Int, 35, 418, 10.1016/j.envint.2008.08.009 Turve RL, Jablonski EJ. Patent: Perfluoro compounds as foams for hydrocarbon fires. US 3258423, 1966. UNFCCC (United Nations Framework Convention on Climate Change) US EPA (United States Environmental Protection Agency), 2005, Final enforceable consent agreement and testing consent order for four formulated composites of fluoropolymer chemicals; export notification, Fed Regist, 70, 39630 US EPA (United States Environmental Protection Agency), 2012, Significant new use rules on certain chemical substances, PMN number P-03-567, Fed Regist, 77, 58677 US EPA (United States Environmental Protection Agency), 2009, 1 US EPA (United States Environmental Protection Agency), 2013 Vaalgamaa, 2011, Photochemical reactivity of perfluorooctanoic acid (PFOA) in conditions representing surface water, Sci Total Environ, 409, 3043, 10.1016/j.scitotenv.2011.04.036 Vestergren, 2009, Tracking the pathways of human exposure to perfluorocarboxylates, Environ Sci Technol, 43, 5565, 10.1021/es900228k Wallington, 1997, Atmospheric chemistry of HFE-7100 (C4F9OCH3): reaction with OH radicals UV spectra and kinetic data for C4F9OCH2 and C4F9OCH2O2 radicals and the atmospheric fate of C4F9OCH2O radicals, J Phys Chem A, 101, 8264, 10.1021/jp971353w Wallington, 2006, Formation of C7F15COOH (PFOA) and other perfluorocarboxylic acids during the atmospheric oxidation of 8:2 fluorotelomer alcohol, Environ Sci Technol, 40, 924, 10.1021/es051858x Wang, 2013, Fluorinated alternatives to long-chain perfluoroalkyl carboxylic acids (PFCAs) perfluoroalkane sulfonic acids (PFSAs) and their potential precursors, Environ Int, 60, 242, 10.1016/j.envint.2013.08.021 Wang, 2014, Global emission inventories for C4–C14 perfluoroalkyl carboxylic acid (PFCA) homologues from 1951 to 2030 part I: production and emissions from quantifiable sources, Environ Int, 69, 166, 10.1016/j.envint.2014.04.006 Wania, 2007, A global mass balance analysis of the source of perfluorocarboxylic acids in the Arctic Ocean, Environ Sci Technol, 41, 4529, 10.1021/es070124c Washington, 2009, Degradability of an acrylate-linked fluorotelomer polymer in soil, Environ Sci Technol, 43, 6617, 10.1021/es9002668 Washington, 2010, Response to comments on “degradability of an acrylate-linked fluorotelomer polymer in soil”, Environ Sci Technol, 44, 849, 10.1021/es902672q Willis, 2007, Re: fluoropolymer incineration ECA; letter to Lynne R. Harris Wolf, 2011 Yamada, 2005, Thermal degradation of fluorotelomer treated articles and related materials, Chemosphere, 61, 974, 10.1016/j.chemosphere.2005.03.025 Yamashita, 2004, Analysis of perfluorinated acids at parts-per-quadrillion levels in seawater using liquid chromatography–tandem mass spectrometry, Environ Sci Technol, 38, 5522, 10.1021/es0492541 Young, 2010, Atmospheric perfluorinated acid precursors: chemistry occurrence and impacts, Rev Environ Contam Toxicol, 208, 1 Young, 2007, Perfluorinated acids in Arctic snow: new evidence for atmospheric formation, Environ Sci Technol, 41, 3455, 10.1021/es0626234 Young, 2009, Atmospheric chemistry of CF3CF2H and CF3CF2CF2CF2H: kinetics and products of gas-phase reactions with Cl atoms and OH radicals infrared spectra and formation of perfluorocarboxylic acids, Chem Phys Lett, 473, 251, 10.1016/j.cplett.2009.04.001