Use of high-resolution mass spectrometry to identify precursors and biodegradation products of perfluorinated and polyfluorinated compounds in end-user products
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- 作者：Atsushi Yamamoto (1) (2)
Hirotaka Hisatomi (1)
Tomoshige Ando (1)
Shusuke Takemine (3)
Tomoko Terao (2)
Toshiki Tojo (2)
Masahiro Yagi (4)
Daisuke Ono (5)
Hideya Kawasaki (1)
Ryuichi Arakawa (1) - 关键词：Perfluorinated compounds ; High ; resolution mass spectrometry ; Orbitrap ; Multidimensional chromatography ; Biodegradation ; Non ; target screening
- 刊名：Analytical and Bioanalytical Chemistry
- 出版年：2014
- 出版时间：July 2014
- 年：2014
- 卷：406
- 期：19
- 页码：4745-4755
- 全文大小：668 KB
- 参考文献：1. The Nine New POPs (2009) Secretariat of the Stockholm convention on persistent organic pollutants, United Nations Environment Programme, Geneva Switzerland. http://chm.pops.int/Programmes/NewPOPs/Publications/tabid/695/language/en-US/Default.aspx. Accessed 3 Mar 2013
2. Paul AG, Jones KC, Sweetman AJ (2009) A first global production, emission, and environmental inventory for perfluorooctane sulfonate. Environ Sci Technol 43:386鈥?92 CrossRef
3. de Voogt P (2010) Perfluorinated alkylated substances. Rev Environ Contam Toxicol Vol 208. Springer, Berlin
4. Fr枚mel T, Knepper TP (2012) In: Knepper TP and Lange FT (eds) Polyfluorinated chemicals and transformation products. Hdbk Env Chem Vol 17. Springer, Berlin
5. Kissa E (2001) Fluorinated surfactants and repellents, 2nd edn. CRC Press, New York
6. 3M Company (1999) Fluorochemical use, distribution and release overview. U.S. EPA administrative record AR226-0550
7. Ministry of Economy, Trade and Industry, Japan (2007) Fact-finding investigation about production and import of chemical substances. (in Japanese) http://www.meti.go.jp/statistics/sei/kagaku/index.html
8. DuPont (2005) DuPont global PFOA strategy. U.S. EPA administrative record AR226-1914
9. UNEP (2006) Report of the persistent organic pollutants review committee on the work of its second meeting Risk profile on perfluorooctane sulfonate. UNEP/POPS/POPRC.2/17/Add.5.
10. Martin JW, Asher BJ, Beesoon S, Benskin JP, Ross MS (2010) PFOS or PreFOS? Are perfluorooctane sulfonate precursors (PreFOS) important determinants of human and environmental perfluorooctane sulfonate (PFOS) exposure? J Environ Monit 12:1979鈥?004 CrossRef
11. D鈥檈on JC, Mabury SA (2011) Is indirect exposure a significant contributor to the burden of perfluorinated acids observed in humans? Environ Sci Technol 45:7974鈥?984 CrossRef
12. Russell MH, Berti WR, Szostek B, Buck RC (2008) Investigation of the biodegradation potential of a fluoroacrylate polymer product in aerobic soils. Environ Sci Technol 42:800鈥?07 CrossRef
13. Washington JW, Ellington J, Jenkins TM, Evans JJ, Yoo H, Hafner SC (2009) Degradability of an acrylate-linked, fluorotelomer polymer in soil. Environ Sci Technol 43:6617鈥?623 CrossRef
14. Opiteck GJ, Lewis KC, Jorgenson JW, Anderegg RJ (1997) Comprehensive on-line LC/LC/MS of proteins. Anal Chem 69:1518鈥?524 CrossRef
15. Julka S, Cortes H, Harfmann R, Bell B, Schweizer-Theobaldt A, Pursch M, Mondello L, Maynard S, West D (2009) Quantitative characterization of solid epoxy resins using comprehensive two-dimensional liquid chromatography coupled with electrospray ionization-time of flight mass spectrometry. Anal Chem 81:4271鈥?279 CrossRef
16. Hogenbooma AC, van Leerdama JA, de Voogt P (2009) Accurate mass screening and identification of emerging contaminants in environmental samples by liquid chromatography鈥揾ybrid linear ion trap Orbitrap mass spectrometry. J Chromatogr A 1216:510鈥?19 CrossRef
17. Hern谩ndez F, Sancho JV, Ib谩帽ez M, Abad E, Portol茅s T, Mattioli L (2012) Current use of high-resolution mass spectrometry in the environmental sciences. Anal Bioanal Chem 403:1251鈥?264 CrossRef
18. Trier X, Granby K, Christensen JH (2011) Tools to discover anionic and nonionic polyfluorinated alkyl surfactants by liquid chromatography electrospray ionisation mass spectrometry. J Chromatogr A 1218:7094鈥?104 CrossRef
19. Buck RC, Franklin J, Berger U, Conder JM, Cousins IT, de Voogt P, Jensen AA, Kannan K, Mabury SA, van Leeuwen SPJ (2011) Perfluoroalkyl and polyfluoroalkyl substances in the environment: terminology, classification, and origins. Integr Environ Assess Manag 7:513鈥?41 CrossRef
20. Allport DC, Gilbert DS, Outterside SM (2003) MDI & TDI: safety health and the environment. John Wiley and Sons, New York CrossRef
21. Terrier P, Douglas DJ (2010) Carbamino group formation with peptides and proteins studied by mass spectrometry. J Am Soc Mass Spectrom 21:1500鈥?505 CrossRef
22. Kumar MR, Prabhakar S, Reddy TJ, Vairamani M (2006) Generation of alkoxide anions from a series of aliphatic diols and alcohols and their ion鈥搈olecule reactions with carbon dioxide in the gas phase. Eur J Mass Spectrom 12:19鈥?4 CrossRef
23. Berger U, Langlois I, Oehmeb M, Kallenborna R (2004) Comparison of three types of mass spectrometer for high-performance liquid chromatography/mass spectrometry analysis of perfluoroalkylated substances and fluorotelomer alcohols. Eur J Mass Spectrom 10:579鈥?88 CrossRef
24. Schr枚der HF (2003) Determination of fluorinated surfactants and their metabolites in sewage sludge samples by liquid chromatography with mass spectrometry and tandem mass spectrometry after pressurised liquid extraction and separation on fluorine-modified reversed-phase solvents. J Chromatogr A 1020:131鈥?51 CrossRef
25. Kirsch P (2004) Modern fluoroorganic chemistry: synthesis, reactivity, applications. Wiley, New York CrossRef
26. Hol膷apek M, Jir谩sko R, L铆sa M (2010) Basic rules for the interpretation of atmospheric pressure ionization mass spectra of small molecules. J Chromatogr A 1217:3908鈥?921 CrossRef
27. Rhoads KR, Janssen EML, Luthy RG, Criddle CS (2008) Aerobic biotransformation and fate of N-ethyl perfluorooctane sulfonamidoethanol (N-EtFOSE) in activated sludge. Environ Sci Technol 42:2873鈥?878 CrossRef
28. Martin JW, Mabury SA, O鈥橞rien PJ (2005) Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepatocytes. Chem Biol Interact 155:165鈥?80 CrossRef
29. Fasano WJ, Sweeney LM, Mawn MP, Nabb DL, Szostek B, Buck RC, Gargas ML (2009) Kinetics of 8鈥? fluorotelomer alcohol and its metabolites, and liver glutathione status following daily oral dosing for 45聽days in male and female rats. Chem Biol Interact 180:281鈥?95 CrossRef
30. Wang N, Szostek B, Buck RC, Folsom PW, Sulecki LM, Gannon JT (2009) 8鈥? Fluorotelomer alcohol aerobic soil biodegradation: pathways, metabolites, and metabolite yields. Chemosphere 75:1089鈥?096 CrossRef
31. Fr枚mel T, Knepper TP (2010) Fluorotelomer ethoxylates: sources of highly fluorinated environmental contaminants part I: biotransformation. Chemosphere 80:1387鈥?392 CrossRef - 作者单位：Atsushi Yamamoto (1) (2)
Hirotaka Hisatomi (1)
Tomoshige Ando (1)
Shusuke Takemine (3)
Tomoko Terao (2)
Toshiki Tojo (2)
Masahiro Yagi (4)
Daisuke Ono (5)
Hideya Kawasaki (1)
Ryuichi Arakawa (1)
1. Kansai University, 3-3-35 Yamatecho, Suita, Osaka, 564-8680, Japan
2. Osaka City Institute of Public Health and Environmental Sciences, 8-34 Tojocho, Tenoji, Osaka, 543-0026, Japan
3. Hyogo Prefectural Institute of Environmental Science, 3-1-27 Yukihira, Suma, Kobe, Hyogo, 652-0037, Japan
4. Kobe Institute of Health, 4-6 Minatojima Nakamachi, Chuo, Kobe, Hyogo, 650-0046, Japan
5. Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto, Osaka, 536-8553, Japan - ISSN：1618-2650
文摘
Structural identification of perfluoroalkyl and polyfluoroalkyl substances found in end-user products and their biodegradation products was performed using ultra-high resolution mass spectrometry. Little attention has so far been paid to the environmental burden of perfluorooctane sulfonate and perfluorooctanoic acid from compounds with a molar mass of ~2,000. Analysis of end-user waterproofing and stain repellent products revealed the presence of numerous ions with molar masses ranging from 1,000 to 2,000 and complex mass spectra. Ultra-high resolution mass spectrometry determined the accurate mass of the observed ions, allowing the cleavage position and fragment structure to be determined. The precursor structures were determined based on reconstitution of the retrieved fragments. Products of fluorochemical manufacturers before voluntary regulation comprised compounds with plural perfluorooctyl chains. In the current product lines, compounds comprising perfluorobutyl chains were detected. Biodegradation tests using activated sludge revealed that biodegradation products consistent with those reported previously were generated even from complex end-user products. For example, the biodegradation test revealed the formation of N-ethyl perfluorooctane sulfonamido acetic acid and various fluorotelomer acids in the samples. The results of the present study suggest that the environmental burden of these compounds should be reevaluated.