2021 Volume 40 Issue 1
Article Contents

ZHANG Hongna, WEN Bei, ZHANG Shuzhen. Environmental occurrence and biotransformation of perfluoroalkyl carboxylic acid precursors: Fluorotelomer alcohols[J]. Environmental Chemistry, 2021, (1): 65-82. doi: 10.7524/j.issn.0254-6108.2020020101
Citation: ZHANG Hongna, WEN Bei, ZHANG Shuzhen. Environmental occurrence and biotransformation of perfluoroalkyl carboxylic acid precursors: Fluorotelomer alcohols[J]. Environmental Chemistry, 2021, (1): 65-82. doi: 10.7524/j.issn.0254-6108.2020020101

Environmental occurrence and biotransformation of perfluoroalkyl carboxylic acid precursors: Fluorotelomer alcohols

  • Corresponding author: WEN Bei, bwen@rcees.ac.cn
  • Received Date: 01/02/2020
    Fund Project: Supported by the National Natural Science Foundation of China (21537005, 21806134, 41671465).
  • Perfluorocarboxylic acids (PFCAs) have received great regulatory attention from the government and international organizations due to their environmental persistence, bioaccumulation and potential toxicity. With the effective reduction of their production and emission in recent years, exploring the indirect sources of PFCAs has become increasingly important. Fluorotelomer alcohols (FTOHs) are important raw materials used to produce fluoropolymers and fluorosurfactants, which have been incorporated into a variety of consumer and industrial products. Moreover, FTOHs are also primary biotransformation intermediates of multiple fluorotelomer-based substances. Degradation of FTOHs has been widely considered as an additional source of PFCAs in the environment and biological species. After entering the environment, FTOHs can undergo long-range transport and can be transformed into polyfluorinated intermediates, and finally oxidized to different carbon-chain lengths of PFCAs. Recent studies also showed that polyfluorinated intermediate metabolites of FTOHs exhibited higher biotoxicity than PFCAs. Therefore, to accurately reveal the environmental and health risks of FTOHs, it is essential to understand their environmental levels and biotransformation routes. In this paper, the sources and physicochemical properties of FTOHs were introduced, the analytical methods and environmental occurrence of FTOHs were reviewed, and the biotransformation processes and toxic mechanisms of FTOHs were analyzed.
  • 加载中
  • [1] PREVEDOUROS K, COUSINS I T, BUCK R C, et al. Sources, fate and transport of perfluorocarboxylates[J]. Environmental Science & Technology, 2006, 40(1):32-44.

    Google Scholar Pub Med

    [2] LINDSTROM A B, STRYNAR M J, LIBELO E L. Polyfluorinated compounds:Past, present, and future[J]. Environmental Science & Technology, 2011, 45(19):7954-7961.

    Google Scholar Pub Med

    [3] KRAFFT M P, RIESS J G. Per- and polyfluorinated substances (PFASs):Environmental challenges[J]. Current Opinion in Colloid & Interface Science, 2015, 20(3):192-212.

    Google Scholar Pub Med

    [4] BENBRAHIM-TALLAA L, LAUBY-SECRETAN B, LOOMIS D, et al. Carcinogenicity of perfluorooctanoic acid, tetrafluoroethylene, dichloromethane, 1,2-dichloropropane, and 1,3-propane sultone[J]. Lancet Oncology, 2014, 15(9):924-925.

    Google Scholar Pub Med

    [5] UNEP. Listing of perfluorooctanoic acid (PFOA), its salts and PFOA-related compounds; UNEP/POP/COP.9/SC-9/12[EB/OL].[2019-12-16]. http://chm.pops.int/TheConvention/ConferenceoftheParties/Meetings/COP9/tabid/7521/Default.aspx.

    Google Scholar Pub Med

    [6] FROMEL T, KNEPPER T P. Biodegradation of fluorinated alkyl substances[J]. Reviews of Environmental Contamination and Toxicology, 2010, 208:161-177.

    Google Scholar Pub Med

    [7] NILSSON H, KARRMAN A, ROTANDER A, et al. Biotransformation of fluorotelomer compound to perfluorocarboxylates in humans[J]. Environment International, 2013, 51:8-12.

    Google Scholar Pub Med

    [8] YUAN G, PENG H, HUANG C, et al. Ubiquitous occurrence of fluorotelomer alcohols in eco-friendly paper-made food-contact materials and their implication for human exposure[J]. Environmental Science & Technology, 2016, 50(2):942-950.

    Google Scholar Pub Med

    [9] D'EON J C, MABURY S A. Is indirect exposure a significant contributor to the burden of perfluorinated acids observed in humans?[J]. Environmental Science & Technology, 2011, 45(19):7974-7984.

    Google Scholar Pub Med

    [10] YOUNG C J, FURDUI V I, FRANKLIN J, et al. Perfluorinated acids in Arctic snow:New evidence for atmospheric formation[J]. Environmental Science & Technology, 2007, 41(10):3455-3461.

    Google Scholar Pub Med

    [11] SHOEIB M, HARNER T, VLAHOS P. Perfluorinated chemicals in the Arctic atmosphere[J]. Environmental Science & Technology, 2006, 40(24):7577-7583.

    Google Scholar Pub Med

    [12] DE SILVA A O, MABURY S A. Isolating isomers of perfluorocarboxylates in polar bears (Ursus maritimus) from two geographical locations[J]. Environmental Science & Technology, 2004, 38(24):6538-6545.

    Google Scholar Pub Med

    [13] WANG X, HALSALL C, CODLING G, et al. Accumulation of perfluoroalkyl compounds in Tibetan Mountain snow:Temporal patterns from 1980 to 2010[J]. Environmental Science & Technology, 2014, 48(1):173-181.

    Google Scholar Pub Med

    [14] BENSKIN J P, PHILLIPS V, ST. LOUIS V L, et al. Source elucidation of perfluorinated carboxylic acids in remote alpine lake sediment cores[J]. Environmental Science & Technology, 2011, 45(17):7188-7194.

    Google Scholar Pub Med

    [15] WANG N, SZOSTEK B, BUCK R C, et al. Fluorotelomer alcohol biodegradation-Direct evidence that perfluorinated carbon chains breakdown[J]. Environmental Science & Technology, 2005, 39(19):7516-7528.

    Google Scholar Pub Med

    [16] LIU J, LEE L S, NIES L F, et al. Biotransformation of 8:2 fluorotelomer alcohol in soil and by soil bacteria isolates[J]. Environmental Science & Technology, 2007, 41(23):8024-8030.

    Google Scholar Pub Med

    [17] CARMOSINI N, LEE L S. Partitioning of fluorotelomer alcohols to octanol and different sources of dissolved organic carbon[J]. Environmental Science & Technology, 2008, 42(17):6559-6565.

    Google Scholar Pub Med

    [18] DINGLASAN-PANLILIO M J A, MABURY S A. Significant residual fluorinated alcohols present in various fluorinated materials[J]. Environmental Science & Technology, 2006, 40(5):1447-1453.

    Google Scholar Pub Med

    [19] LIU J, LEE L S. Effect of fluorotelomer alcohol chain length on aqueous solubility and sorption by soils[J]. Environmental Science & Technology, 2007, 41(15):5357-5362.

    Google Scholar Pub Med

    [20] LIU J, LEE L S. Solubility and sorption by soils of 8:2 fluorotelomer alcohol in water and cosolvent systems[J]. Environmental Science & Technology, 2005, 39(19):7535-7540.

    Google Scholar Pub Med

    [21] STOCK N L, ELLIS D A, DELEEBEECK L, et al. Vapor pressures of the fluorinated telomer alcohols-Limitations of estimation methods[J]. Environmental Science & Technology, 2004, 38(6):1693-1699.

    Google Scholar Pub Med

    [22] ARP H P H, NIEDERER C, GOSS K U. Predicting the partitioning behavior of various highly fluorinated compounds[J]. Environmental Science & Technology, 2006, 40(23):7298-7304.

    Google Scholar Pub Med

    [23] OECD. Preliminary lists of PFOS, PFAS, PFOA and related compounds and chemicals that may degrade to PFCA[J]. OECD Papers, 2006, 6(11):158-351.

    Google Scholar Pub Med

    [24] D'EON J C, CROZIER P W, FURDUI V I, et al. Observation of a commercial fluorinated material, the polyfluoroalkyl phosphoric acid diesters, in human sera, wastewater treatment plant sludge, and paper fibers[J]. Environmental Science & Technology, 2009, 43(12):4589-4594.

    Google Scholar Pub Med

    [25] LEE H, D'EON J, MABURY S A. Biodegradation of polyfluoroalkyl phosphates as a source of perfluorinated acids to the environment[J]. Environmental Science & Technology, 2010, 44(9):3305-3310.

    Google Scholar Pub Med

    [26] CHEN M, GUO T, HE K, et al. Biotransformation and bioconcentration of 6:2 and 8:2 polyfluoroalkyl phosphate diesters in common carp (Cyprinus carpio):Underestimated ecological risks[J]. Science of the Total Environment, 2019, 656:201-208.

    Google Scholar Pub Med

    [27] DASU K, LIU J, LEE L S. Aerobic soil biodegradation of 8:2 fluorotelomer stearate monoester[J]. Environmental Science & Technology, 2012, 46(7):3831-3836.

    Google Scholar Pub Med

    [28] BUTT C M, MUIR D C, MABURY S A. Biotransformation of the 8:2 fluorotelomer acrylate in rainbow trout. 1. In vivo dietary exposure[J]. Environmental Toxicology and Chemistry, 2010, 29(12):2726-2735.

    Google Scholar Pub Med

    [29] BUTT C M, YOUNG C J, MABURY S A, et al. Atmospheric chemistry of 4:2 fluorotelomer acrylate C4F9CH2CH2OC(O)CH=CH2:Kinetics, mechanisms, and products of chlorine-atom- and OH-radical-initiated oxidation[J]. Journal of Physical Chemistry A, 2009, 113(13):3155-3161.

    Google Scholar Pub Med

    [30] WANG N, LIU J, BUCK R C, et al. 6:2 Fluorotelomer sulfonate aerobic biotransformation in activated sludge of waste water treatment plants[J]. Chemosphere, 2011, 82(6):853-858.

    Google Scholar Pub Med

    [31] SHAW D M J, MUNOZ G, BOTTOS E M, et al. Degradation and defluorination of 6:2 fluorotelomer sulfonamidoalkyl betaine and 6:2 fluorotelomer sulfonate by Gordonia sp. strain NB4-1Y under sulfur-limiting conditions[J]. Science of the Total Environment, 2019, 647:690-698.

    Google Scholar Pub Med

    [32] RUAN T, SZOSTEK B, FOLSOM P W, et al. Aerobic soil biotransformation of 6:2 fluorotelomer iodide[J]. Environmental Science & Technology, 2013, 47(20):11504-11511.

    Google Scholar Pub Med

    [33] RUAN T, WANG Y W, WANG T, et al. Presence and partitioning behavior of polyfluorinated iodine alkanes in environmental matrices around a fluorochemical manufacturing plant:Another possible source for perfluorinated carboxylic acids?[J]. Environmental Science & Technology, 2010, 44(15):5755-5761.

    Google Scholar Pub Med

    [34] RANKIN K, LEE H, TSENG P J, et al. Investigating the biodegradability of a fluorotelomer-based acrylate polymer in a soil-plant microcosm by indirect and direct analysis[J]. Environmental Science & Technology, 2014, 48(21):12783-12790.

    Google Scholar Pub Med

    [35] RUSSELL M H, BERTI W R, SZOSTEK B, et al. Investigation of the biodegradation potential of a fluoroacrylate polymer product in aerobic soils[J]. Environmental Science & Technology, 2008, 42(3):800-807.

    Google Scholar Pub Med

    [36] LI L, LIU J, HU J, et al. Degradation of fluorotelomer-based polymers contributes to the global occurrence of fluorotelomer alcohol and perfluoroalkyl carboxylates:A combined dynamic substance flow and environmental fate modeling analysis[J]. Environmental Science & Technology, 2017, 51(8):4461-4470.

    Google Scholar Pub Med

    [37] SZOSTEK B, PRICKETT K B. Determination of 8:2 fluorotelomer alcohol in animal plasma and tissues by gas chromatography-mass spectrometry[J]. Journal of Chromatography B, 2004, 813(1/2):313-321.

    Google Scholar Pub Med

    [38] MARTIN J W, MUIR D C G, MOODY C A, et al. Collection of airborne fluorinated organics and analysis by gas chromatography/chemical ionization mass spectrometry[J]. Analytical Chemistry, 2002, 74(3):584-590.

    Google Scholar Pub Med

    [39] ELLINGTON J J, WASHINGTON J W, EVANS J J, et al. Analysis of fluorotelomer alcohols in soils:Optimization of extraction and chromatography[J]. Journal of Chromatography A, 2009, 1216(28):5347-5354.

    Google Scholar Pub Med

    [40] YOO H, WASHINGTON J W, ELLINGTON J J, et al. Concentrations, distribution, and persistence of fluorotelomer alcohols in sludge-applied soils near Decatur, Alabama, USA[J]. Environmental Science & Technology, 2010, 44(22):8397-8402.

    Google Scholar Pub Med

    [41] YOO H, WASHINGTON J W, JENKINS T M, et al. Quantitative determination of perfluorochemicals and fluorotelomer alcohols in plants from biosolid-amended fields using LC/MS/MS and GC/MS[J]. Environmental Science & Technology, 2011, 45(19):7985-7990.

    Google Scholar Pub Med

    [42] RIEDEL T P, LANG J R, STRYNAR M J, et al. Gas-phase detection of fluorotelomer alcohols and other oxygenated per- and polyfluoroalkyl substances by chemical ionization mass spectrometry[J]. Environmental Science & Technology Letters, 2019, 6(5):289-293.

    Google Scholar Pub Med

    [43] SZOSTEK B, PRICKETT K B, BUCK R C. Determination of fluorotelomer alcohols by liquid chromatography/tandem mass spectrometry in water[J]. Rapid Communications in Mass Spectrometry, 2006, 20(19):2837-2844.

    Google Scholar Pub Med

    [44] ZHANG S, SZOSTEK B, MCCAUSLAND P K, et al. 6:2 and 8:2 Fluorotelomer alcohol anaerobic biotransformation in digester sludge from a WWTP under methanogenic conditions[J]. Environmental Science & Technology, 2013, 47(9):4227-4235.

    Google Scholar Pub Med

    [45] ZHAO L, FOLSOM P W, WOLSTENHOLME B W, et al. 6:2 Fluorotelomer alcohol biotransformation in an aerobic river sediment system[J]. Chemosphere, 2013, 90(2):203-209.

    Google Scholar Pub Med

    [46] NABB D L, SZOSTEK B, HIMMELSTEIN M W, et al. In vitro metabolism of 8-2 fluorotelomer alcohol:Interspecies comparisons and metabolic pathway refinement[J]. Toxicological Sciences, 2007, 100(2):333-344.

    Google Scholar Pub Med

    [47] BERGER U, LANGLOIS I, OEHME M, et al. Comparison of three types of mass spectrometer for high-performance liquid chromatography/mass spectrometry analysis of perfluoroalkylated substances and fluorotelomer alcohols[J]. European Journal of Mass Spectrometry, 2004, 10(5):579-588.

    Google Scholar Pub Med

    [48] ZHANG H, WEN B, HU X, et al. Determination of fluorotelomer alcohols and their degradation products in biosolids-amended soils and plants using ultra-high performance liquid chromatography tandem mass spectrometry[J]. Journal of Chromatography A, 2015, 1404:72-80.

    Google Scholar Pub Med

    [49] PENG H, HU K, ZHAO F, et al. Derivatization method for sensitive determination of fluorotelomer alcohols in sediment by liquid chromatography-electrospray tandem mass spectrometry[J]. Journal of Chromatography A, 2013, 1288:48-53.

    Google Scholar Pub Med

    [50] WONG F, SHOEIB M, KATSOYIANNIS A, et al. Assessing temporal trends and source regions of per- and polyfluoroalkyl substances (PFASs) in air under the Arctic Monitoring and Assessment Programme (AMAP)[J]. Atmospheric Environment, 2018, 172:65-73.

    Google Scholar Pub Med

    [51] JAHNKE A, BERGER U, EBINGHAUS R, et al. Latitudinal gradient of airborne polyfluorinated alkyl substances in the marine atmosphere between Germany and South Africa (53°N-33°S)[J]. Environmental Science & Technology, 2007, 41(9):3055-3061.

    Google Scholar Pub Med

    [52] LI J, DEL VENTO S, SCHUSTER J, et al. Perfluorinated compounds in the Asian atmosphere[J]. Environmental Science & Technology, 2011, 45(17):7241-7248.

    Google Scholar Pub Med

    [53] AHRENS L, SHOEIB M, HARNER T, et al. Wastewater treatment plant and landfills as sources of polyfluoroalkyl compounds to the atmosphere[J]. Environmental Science & Technology, 2011, 45(19):8098-8105.

    Google Scholar Pub Med

    [54] TIAN Y, YAO Y, CHANG S, et al. Occurrence and phase distribution of neutral and ionizable per- and polyfluoroalkyl substances (PFASs) in the atmosphere and plant leaves around landfills:A case study in Tianjin, China[J]. Environmental Science & Technology, 2018, 52(3):1301-1310.

    Google Scholar Pub Med

    [55] KIM S K, SHOEIB M, KIM K S, et al. Indoor and outdoor poly- and perfluoroalkyl substances (PFASs) in Korea determined by passive air sampler[J]. Environmental Pollution, 2012, 162:144-150.

    Google Scholar Pub Med

    [56] SHOEIB M, HARNER T, WEBSTER G M, et al. Indoor sources of poly- and perfluorinated compounds (PFCS) in Vancouver, Canada:Implications for human exposure[J]. Environmental Science & Technology, 2011, 45(19):7999-8005.

    Google Scholar Pub Med

    [57] NILSSON H, KARRMAN A, ROTANDER A, et al. Inhalation exposure to fluorotelomer alcohols yield perfluorocarboxylates in human blood?[J]. Environmental Science & Technology, 2010, 44(19):7717-7722.

    Google Scholar Pub Med

    [58] STRYNAR M J, LINDSTROM A B. Perfluorinated compounds in house dust from Ohio and North Carolina, USA[J]. Environmental Science & Technology, 2008, 42(10):3751-3756.

    Google Scholar Pub Med

    [59] XIE Z, ZHAO Z, MOLLER A, et al. Neutral poly- and perfluoroalkyl substances in air and seawater of the North Sea[J]. Environmental Science and Pollution Research, 2013, 20(11):7988-8000.

    Google Scholar Pub Med

    [60] MAHMOUD M A M, KÄRRMAN A, OONO S, et al. Polyfluorinated telomers in precipitation and surface water in an urban area of Japan[J]. Chemosphere, 2009, 74(3):467-472.

    Google Scholar Pub Med

    [61] BACH C, BOITEUX V, HEMARD J, et al. Simultaneous determination of perfluoroalkyl iodides, perfluoroalkane sulfonamides, fluorotelomer alcohols, fluorotelomer iodides and fluorotelomer acrylates and methacrylates in water and sediments using solid-phase microextraction-gas chromatography/mass spectrometry[J]. Journal of Chromatography A, 2016, 1448:98-106.

    Google Scholar Pub Med

    [62] TANIYASU S, KANNAN K, SO M K, et al. Analysis of fluorotelomer alcohols, fluorotelomer acids, and short- and long-chain perfluorinated acids in water and biota[J]. Journal of Chromatography A, 2005, 1093(1/2):89-97.

    Google Scholar Pub Med

    [63] SINCLAIR E, KANNAN K. Mass loading and fate of perfluoroalkyl surfactants in wastewater treatment plants[J]. Environmental Science & Technology, 2006, 40(5):1408-1414.

    Google Scholar Pub Med

    [64] ZHANG T, SUN H, GERECKE A C, et al. Comparison of two extraction methods for the analysis of per- and polyfluorinated chemicals in digested sewage sludge[J]. Journal of Chromatography A, 2010, 1217(31):5026-5034.

    Google Scholar Pub Med

    [65] CHEN H, PENG H, YANG M, et al. Detection, occurrence, and fate of fluorotelomer alcohols in municipal wastewater treatment plants[J]. Environmental Science & Technology, 2017, 51(16):8953-8961.

    Google Scholar Pub Med

    [66] WASHINGTON J W, YOO H, ELLINGTON J J, et al. Concentrations, distribution, and persistence of perfluoroalkylates in sludge-applied soils near Decatur, Alabama, USA[J]. Environmental Science & Technology, 2010, 44(22):8390-8396.

    Google Scholar Pub Med

    [67] XU Z, LI L, HENKELMANN B, et al. Occurrence of fluorotelomer alcohols at two Alpine summits:Sources, transport and temporal trends[J]. Environmental Chemistry, 2017, 14(4):215-223.

    Google Scholar Pub Med

    [68] XIE Z, WANG Z, MI W, et al. Neutral poly-/perfluoroalkyl substances in air and snow from the Arctic[J]. Scientific Reports, 2015, 5(1):8912.

    Google Scholar Pub Med

    [69] BOSSI R, VORKAMP K, SKOV H. Concentrations of organochlorine pesticides, polybrominated diphenyl ethers and perfluorinated compounds in the atmosphere of North Greenland[J]. Environmental Pollution, 2016, 217:4-10.

    Google Scholar Pub Med

    [70] YAO Y, CHANG S, SUN H, et al. Neutral and ionic per- and polyfluoroalkyl substances (PFASs) in atmospheric and dry deposition samples over a source region (Tianjin, China)[J]. Environmental Pollution, 2016, 212:449-456.

    Google Scholar Pub Med

    [71] HEYDEBRECK F, TANG J, XIE Z, et al. Emissions of per- and polyfluoroalkyl substances in a textile manufacturing plant in China and their relevance for workers' exposure[J]. Environmental Science & Technology, 2016, 50(19):10386-10396.

    Google Scholar Pub Med

    [72] SCHLUMMER M, GRUBER L, FIEDLER D, et al. Detection of fluorotelomer alcohols in indoor environments and their relevance for human exposure[J]. Environment International, 2013, 57/58:42-49.

    Google Scholar Pub Med

    [73] LIU W, TAKAHASHI S, SAKURAMACHI Y, et al. Polyfluorinated telomers in indoor air of Japanese houses[J]. Chemosphere, 2013, 90(5):1672-1677.

    Google Scholar Pub Med

    [74] HAUG L S, HUBER S, SCHLABACH M, et al. Investigation on per- and polyfluorinated compounds in paired samples of house dust and indoor air from Norwegian homes[J]. Environmental Science & Technology, 2011, 45(19):7991-7998.

    Google Scholar Pub Med

    [75] PADILLA-SÁNCHEZ J A, PAPADOPOULOU E, POOTHONG S, et al. Investigation of the best approach for assessing human exposure to poly- and perfluoroalkyl substances through indoor air[J]. Environmental Science & Technology, 2017, 51(21):12836-12843.

    Google Scholar Pub Med

    [76] SHA B, DAHLBERG A-K, WIBERG K, et al. Fluorotelomer alcohols (FTOHs), brominated flame retardants (BFRs), organophosphorus flame retardants (OPFRs) and cyclic volatile methylsiloxanes (cVMSs) in indoor air from occupational and home environments[J]. Environmental Pollution, 2018, 241:319-330.

    Google Scholar Pub Med

    [77] FRASER A J, WEBSTER T F, WATKINS D J, et al. Polyfluorinated compounds in serum linked to indoor air in office environments[J]. Environmental Science & Technology, 2012, 46(2):1209-1215.

    Google Scholar Pub Med

    [78] ZHENG G, BOOR B E, SCHREDER E, et al. Indoor exposure to per- and polyfluoroalkyl substances (PFAS) in the childcare environment[J]. Environmental Pollution, 2020, 258:113714.

    Google Scholar Pub Med

    [79] YAO Y, ZHAO Y, SUN H, et al. Per- and polyfluoroalkyl substances (PFASs) in indoor air and dust from homes and various microenvironments in China:Implications for human exposure[J]. Environmental Science & Technology, 2018, 52(5):3156-3166.

    Google Scholar Pub Med

    [80] WANG N, SZOSTEK B, FOLSOM P W, et al. Aerobic biotransformation of C-14-labeled 8-2 telomer B alcohol by activated sludge from a domestic sewage treatment plant[J]. Environmental Science & Technology, 2005, 39(2):531-538.

    Google Scholar Pub Med

    [81] WANG N, SZOSTEK B, BUCK R C, et al. 8-2 Fluorotelomer alcohol aerobic soil biodegradation:Pathways, metabolites, and metabolite yields[J]. Chemosphere, 2009, 75(8):1089-1096.

    Google Scholar Pub Med

    [82] DINGLASAN M J A, YE Y, EDWARDS E A, et al. Fluorotelomer alcohol biodegradation yields poly- and perfluorinated acids[J]. Environmental Science & Technology, 2004, 38(10):2857-2864.

    Google Scholar Pub Med

    [83] KIM M H, WANG N, MCDONALD T, et al. Biodefluorination and biotransformation of fluorotelomer alcohols by two alkane-degrading Pseudomonas strains[J]. Biotechnology and Bioengineering, 2012, 109(12):3041-3048.

    Google Scholar Pub Med

    [84] LI F, SU Q, ZHOU Z, et al. Anaerobic biodegradation of 8:2 fluorotelomer alcohol in anaerobic activated sludge:Metabolic products and pathways[J]. Chemosphere, 2018, 200:124-132.

    Google Scholar Pub Med

    [85] 何娜, 周萌, 汪磊, 等. 6-2氟调醇在活性污泥中的降解[J]. 环境科学学报, 2013, 33(2):383-388. HE N, ZHOU M, WANG L, et al. Biodegradation of 6-2 fluorotelomer alchol in activated sludge[J]. Acta Scientiae Circumstantiae, 2013, 33(2):383-388(in Chinese).

    Google Scholar Pub Med

    [86] ZHANG S, MERINO N, WANG N, et al. Impact of 6:2 fluorotelomer alcohol aerobic biotransformation on a sediment microbial community[J]. Science of the Total Environment, 2017, 575:1361-1368.

    Google Scholar Pub Med

    [87] LIU J, WANG N, BUCK R C, et al. Aerobic biodegradation of[C-14] 6:2 fluorotelomer alcohol in a flow-through soil incubation system[J]. Chemosphere, 2010, 80(7):716-723.

    Google Scholar Pub Med

    [88] LIU J, WANG N, SZOSTEK B, et al. 6-2 Fluorotelomer alcohol aerobic biodegradation in soil and mixed bacterial culture[J]. Chemosphere, 2010, 78(4):437-444.

    Google Scholar Pub Med

    [89] WASHINGTON J W, ELLINGTON J J, JENKINS T M, et al. Degradability of an acrylate-linked, fluorotelomer polymer in soil[J]. Environmental Science & Technology, 2009, 43(17):6617-6623.

    Google Scholar Pub Med

    [90] LIOU J S C, SZOSTEK B, DERITO C M, et al. Investigating the biodegradability of perfluorooctanoic acid[J]. Chemosphere, 2010, 80(2):176-183.

    Google Scholar Pub Med

    [91] WANG N, BUCK R C, SZOSTEK B, et al. 5:3 Polyfluorinated acid aerobic biotransformation in activated sludge via novel "one-carbon removal pathways"[J]. Chemosphere, 2012, 87(5):527-534.

    Google Scholar Pub Med

    [92] KIM M H, WANG N, CHU K H. 6:2 Fluorotelomer alcohol (6:2 FTOH) biodegradation by multiple microbial species under different physiological conditions[J]. Applied Microbiology and Biotechnology, 2014, 98(4):1831-1840.

    Google Scholar Pub Med

    [93] LIU J, AVENDANO S M. Microbial degradation of polyfluoroalkyl chemicals in the environment:A review[J]. Environment International, 2013, 61:98-114.

    Google Scholar Pub Med

    [94] HAGEN D F, BELISLE J, JOHNSON J D, et al. Characterization of fluorinated metabolites by a gas chromatographic-helium microwave plasma detector-The biotransformation of 1H,1H,2H,2H-perfluorodecanol to perfluorooctanoate[J]. Analytical Biochemistry, 1981, 118(2):336-343.

    Google Scholar Pub Med

    [95] FASANO W J, CARPENTER S C, GANNON S A, et al. Absorption, distribution, metabolism, and elimination of 8-2 fluorotelomer alcohol in the rat[J]. Toxicological Sciences, 2006, 91(2):341-355.

    Google Scholar Pub Med

    [96] FASANO W J, SWEENEY L M, MAWN M P, et al. Kinetics of 8-2 fluorotelomer alcohol and its metabolites, and liver glutathione status following daily oral dosing for 45 days in male and female rats[J]. Chemico-Biological Interactions, 2009, 180(2):281-295.

    Google Scholar Pub Med

    [97] HIMMELSTEIN M W, SEREX T L, BUCK R C, et al. 8:2 Fluorotelomer alcohol:A one-day nose-only inhalation toxicokinetic study in the Sprague-Dawley rat with application to risk assessment[J]. Toxicology, 2012, 291(1/3):122-132.

    Google Scholar Pub Med

    [98] MARTIN J W, MABURY S A, O'BRIEN P J. Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepatocytes[J]. Chemico-Biological Interactions, 2005, 155(3):165-180.

    Google Scholar Pub Med

    [99] MARTIN J W, CHAN K, MABURY S A, et al. Bioactivation of fluorotelomer alcohols in isolated rat hepatocytes[J]. Chemico-Biological Interactions, 2009, 177(3):196-203.

    Google Scholar Pub Med

    [100] RAND A A, MABURY S A. Covalent binding of fluorotelomer unsaturated aldehydes (FTUALs) and carboxylic acids (FTUCAs) to proteins[J]. Environmental Science & Technology, 2013, 47(3):1655-1663.

    Google Scholar Pub Med

    [101] RAND A A, MABURY S A. Protein binding associated with exposure to fluorotelomer alcohols (FTOHs) and polyfluoroalkyl phosphate esters (PAPs) in rats[J]. Environmental Science & Technology, 2014, 48(4):2421-2429.

    Google Scholar Pub Med

    [102] RUSSELL M H, HIMMELSTEIN M W, BUCK R C. Inhalation and oral toxicokinetics of 6:2 FTOH and its metabolites in mammals[J]. Chemosphere, 2015, 120:328-335.

    Google Scholar Pub Med

    [103] BUTT C M, MUIR D C G, MABURY S A. Elucidating the pathways of poly- and perfluorinated acid formation in rainbow trout[J]. Environmental Science & Technology, 2010, 44(13):4973-4980.

    Google Scholar Pub Med

    [104] BRANDSMA S H, SMITHWICK M, SOLOMON K, et al. Dietary exposure of rainbow trout to 8:2 and 10:2 fluorotelomer alcohols and perfluorooctanesulfonamide:Uptake, transformation and elimination[J]. Chemosphere, 2011, 82(2):253-258.

    Google Scholar Pub Med

    [105] ZHANG H, WEN B, HU X, et al. Uptake, translocation, and metabolism of 8:2 fluorotelomer alcohol in soybean (Glycine max L. Merrill)[J]. Environmental Science & Technology, 2016, 50(24):13309-13317.

    Google Scholar Pub Med

    [106] ZHANG H, WEN B, HUANG H, et al. Biotransformation of 6:2 fluorotelomer alcohol by the whole soybean (Glycine max L. Merrill) seedlings[J]. Environmental Pollution, 2020, 257:113513.

    Google Scholar Pub Med

    [107] ZHAO S, ZHU L. Uptake and metabolism of 10:2 fluorotelomer alcohol in soil-earthworm (Eisenia fetida) and soil-wheat (Triticum aestivum L.) systems[J]. Environmental Pollution, 2017, 220:124-131.

    Google Scholar Pub Med

    [108] FROMME H, TITTLEMIER S A, VÖLKEL W, et al. Perfluorinated compounds-Exposure assessment for the general population in western countries[J]. International Journal of Hygiene and Environmental Health, 2009, 212(3):239-270.

    Google Scholar Pub Med

    [109] NILSSON H, KÄRRMAN A, WESTBERG H, et al. A time trend study of significantly elevated perfluorocarboxylate levels in humans after using fluorinated ski wax[J]. Environmental Science & Technology, 2010, 44(6):2150-2155.

    Google Scholar Pub Med

    [110] DUAN Y, SUN H, YAO Y, et al. Distribution of novel and legacy per-/polyfluoroalkyl substances in serum and its associations with two glycemic biomarkers among Chinese adult men and women with normal blood glucose levels[J]. Environment International, 2020, 134:105295.

    Google Scholar Pub Med

    [111] LI Z M, GUO L H, REN X M. Biotransformation of 8:2 fluorotelomer alcohol by recombinant human cytochrome P450s, human liver microsomes and human liver cytosol[J]. Environmental Science-Processes & Impacts, 2016, 18:538-546.

    Google Scholar Pub Med

    [112] DAGNINO S, STRYNAR M J, MCMAHEN R L, et al. Identification of biomarkers of exposure to FTOHs and PAPs in humans using a targeted and nontargeted analysis approach[J]. Environmental Science & Technology, 2016, 50(18):10216-10225.

    Google Scholar Pub Med

    [113] LADICS G S, KENNEDY G L, O'CONNOR J, et al. 90-Day oral gavage toxicity study of 8-2 fluorotelomer alcohol in rats[J]. Drug and Chemical Toxicology, 2008, 31(2):189-216.

    Google Scholar Pub Med

    [114] LADICS G S, STADLER J C, MAKOVEC G T, et al. Subchronic toxicity of a fluoroalkylethanol mixture in rats[J]. Drug and Chemical Toxicology, 2005, 28(2):135-158.

    Google Scholar Pub Med

    [115] KUDO N, IWASE Y, OKAYACHI H, et al. Induction of hepatic peroxisome proliferation by 8-2 telomer alcohol feeding in mice:Formation of perfluorooctanoic acid in the liver[J]. Toxicological Sciences, 2005, 86(2):231-238.

    Google Scholar Pub Med

    [116] WANG X, KONG B, HE B, et al. 8:2 Fluorotelomer alcohol causes immunotoxicity and liver injury in adult male C57BL/6 mice[J]. Environmental Toxicology, 2019, 34(2):141-149.

    Google Scholar Pub Med

    [117] MYLCHREEST E, LADICS G S, MUNLEY S M, et al. Evaluation of the reproductive and developmental toxicity of a fluoroalkylethanol mixture[J]. Drug and Chemical Toxicology, 2005, 28(2):159-175.

    Google Scholar Pub Med

    [118] MARAS M, VANPARYS C, MUYLLE F, et al. Estrogen-like properties of fluorotelomer alcohols as revealed by MCF-7 breast cancer cell proliferation[J]. Environmental Health Perspectives, 2006, 114(1):100-105.

    Google Scholar Pub Med

    [119] VANPARYS C, MARAS M, LENJOU M, et al. Flow cytometric cell cycle analysis allows for rapid screening of estrogenicity in MCF-7 breast cancer cells[J]. Toxicology in Vitro, 2006, 20(7):1238-1248.

    Google Scholar Pub Med

    [120] ISHIBASHI H, YAMAUCHI R, MATSUOKA M, et al. Fluorotelomer alcohols induce hepatic vitellogenin through activation of the estrogen receptor in male medaka (Oryzias latipes)[J]. Chemosphere, 2008, 71(10):1853-1859.

    Google Scholar Pub Med

    [121] LIU C, DU Y, ZHOU B. Evaluation of estrogenic activities and mechanism of action of perfluorinated chemicals determined by vitellogenin induction in primary cultured tilapia hepatocytes[J]. Aquatic Toxicology, 2007, 85(4):267-277.

    Google Scholar Pub Med

    [122] WANG X, ZHOU C, HE B, et al. 8:2 Fluorotelomer alcohol causes G1 cell cycle arrest and blocks granulocytic differentiation in HL-60 cells[J]. Environmental Toxicology, 2019, 34(5):666-673.

    Google Scholar Pub Med

    [123] KONG B, WANG X, HE B, et al. 8:2 Fluorotelomer alcohol inhibited proliferation and disturbed the expression of pro-inflammatory cytokines and antigen-presenting genes in murine macrophages[J]. Chemosphere, 2019, 219:1052-1060.

    Google Scholar Pub Med

    [124] LIU C, YU L, DENG J, et al. Waterborne exposure to fluorotelomer alcohol 6:2 FTOH alters plasma sex hormone and gene transcription in the hypothalamic-pituitary-gonadal (HPG) axis of zebrafish[J]. Aquatic Toxicology, 2009, 93(2/3):131-137.

    Google Scholar Pub Med

    [125] LIU C, DENG J, YU L, et al. Endocrine disruption and reproductive impairment in zebrafish by exposure to 8:2 fluorotelomer alcohol[J]. Aquatic Toxicology, 2010, 96(1):70-76.

    Google Scholar Pub Med

    [126] LIU C, ZHANG X, CHANG H, et al. Effects of fluorotelomer alcohol 8:2 FTOH on steroidogenesis in H295R cells:Targeting the cAMP signalling cascade[J]. Toxicology and Applied Pharmacology, 2010, 247(3):222-228.

    Google Scholar Pub Med

    [127] LOVELESS S E, FINLAY C, EVERDS N E, et al. Comparative responses of rats and mice exposed to linear/branched, linear, or branched ammonium perfluorooctanoate (APFO)[J]. Toxicology, 2006, 220(2/3):203-217.

    Google Scholar Pub Med

    [128] PERKINS R G, BUTENHOFF J L, JR K G, et al. 13-Week dietary toxicity study of ammonium perfluorooctanoate (APFO) in male rats[J]. Drug and Chemical Toxicology, 2004, 27(4):361-378.

    Google Scholar Pub Med

    [129] PHILLIPS M M, DINGLASAN-PANLILIO M J, MABURY S A, et al. Fluorotelomer acids are more toxic than perfluorinated acids[J]. Environmental Science & Technology, 2007, 41(20):7159-7163.

    Google Scholar Pub Med

    [130] RAND A A, ROONEY J P, BUTT C M, et al. Cellular toxicity associated with exposure to perfluorinated carboxylates (PFCAs) and their metabolic precursors[J]. Chemical Research in Toxicology, 2014, 27(1):42-50.

    Google Scholar Pub Med

    [131] SHI G, CUI Q, PAN Y, et al. 6:2 Fluorotelomer carboxylic acid (6:2 FTCA) exposure induces developmental toxicity and inhibits the formation of erythrocytes during zebrafish embryogenesis[J]. Aquatic Toxicology, 2017, 190:53-61.

    Google Scholar Pub Med

  • 加载中
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

Article Metrics

Article views(4884) PDF downloads(166) Cited by(0)

Access History

Environmental occurrence and biotransformation of perfluoroalkyl carboxylic acid precursors: Fluorotelomer alcohols

Fund Project: Supported by the National Natural Science Foundation of China (21537005, 21806134, 41671465).

Abstract: Perfluorocarboxylic acids (PFCAs) have received great regulatory attention from the government and international organizations due to their environmental persistence, bioaccumulation and potential toxicity. With the effective reduction of their production and emission in recent years, exploring the indirect sources of PFCAs has become increasingly important. Fluorotelomer alcohols (FTOHs) are important raw materials used to produce fluoropolymers and fluorosurfactants, which have been incorporated into a variety of consumer and industrial products. Moreover, FTOHs are also primary biotransformation intermediates of multiple fluorotelomer-based substances. Degradation of FTOHs has been widely considered as an additional source of PFCAs in the environment and biological species. After entering the environment, FTOHs can undergo long-range transport and can be transformed into polyfluorinated intermediates, and finally oxidized to different carbon-chain lengths of PFCAs. Recent studies also showed that polyfluorinated intermediate metabolites of FTOHs exhibited higher biotoxicity than PFCAs. Therefore, to accurately reveal the environmental and health risks of FTOHs, it is essential to understand their environmental levels and biotransformation routes. In this paper, the sources and physicochemical properties of FTOHs were introduced, the analytical methods and environmental occurrence of FTOHs were reviewed, and the biotransformation processes and toxic mechanisms of FTOHs were analyzed.

Reference (131)

Catalog

    /

    DownLoad:  Full-Size Img  PowerPoint