6:2 Fluorotelomer alcohol biotransformation in an aerobic river sediment system

Zhao, Lijie; Folsom, Patrick W.; Wolstenholme, Barry W.; Sun, Hongwen; Wang, Ning; Buck, Robert C.

doi:10.1016/j.chemosphere.2012.06.035

Cited by 83 publications

(100 citation statements)

References 31 publications

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“…Release of 6:2 FTOH from production application may steadily increase and, thus, become a predominant FTOH in the environment (Ritter 2010). A study of 6:2 FTOH biotransformation in an aerobic river sediment system has revealed that the primary biotransformation of 6:2 FTOH was rapid with a half-life time of <2 days and formed polyfluorinated acids after 100 days (Zhao et al 2013). Seawater concentrations determined in this work may suggest that FTOHs are mainly released from old FTOH-based (C≥10) products in use in Europe.…”

Section: Pfass In Seawatermentioning

confidence: 99%

Neutral poly- and perfluoroalkyl substances in air and seawater of the North Sea

Xie¹,

Zhao

Møller

et al. 2013

Environ Sci Pollut Res

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Concentrations of neutral poly-and perfluoroalkyl substances (PFASs), such as fluorotelomer alcohols (FTOHs), perfluoroalkane sulfonamides (FASAs), perfluoroalkane sufonamidoethanols (FASEs), and fluorotelomer acrylates (FTACs), have been simultaneously determined in surface seawater and the atmosphere of the North Sea. Seawater and air samples were taken aboard the German research vessel Heincke on the cruise 303 from 15 to 24 May 2009. The concentrations of FTOHs, FASAs, FASEs, and FTACs in the dissolved phase were 2.6-74, <0.1-19, <0.1-63, and <1.0-9.0 pg L −1 , respectively. The highest concentrations were determined in the estuary of the Weser and Elbe rivers and a decreasing concentration profile appeared with increasing distance from the coast toward the central part of the North Sea. Gaseous FTOHs, FASAs, FASEs, and FTACs were in the range of 36-126, 3.1-26, 3.7-19, and 0.8-5.6 pg m −3 , which were consistent with the concentrations determined in 2007 in the North Sea, and approximately five times lower than those reported for an urban area of Northern Germany. These results suggested continuous continental emissions of neutral PFASs followed by transport toward the marine environment.Air-seawater gas exchanges of neutral PFASs were estimated using fugacity ratios and the two-film resistance model based upon paired air-seawater concentrations and estimated Henry's law constant values. Volatilization dominated for all neutral PFASs in the North Sea. The air-seawater gas exchange fluxes were in the range of 2.5×10 3 -3.6×10 5 pg m −2 for FTOHs, 1.8 × 10 2 -1.0 × 10 5 pg m −2 for FASAs, 1.1 × 10 2 -3.0 × 10 5 pg m −2 for FASEs and 6.3×10 2 -2.0×10 4 pg m −2 for FTACs, respectively. These results suggest that the air-seawater gas exchange is an important process that intervenes in the transport and fate for neutral PFASs in the marine environment.

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Section: Pfass In Seawatermentioning

confidence: 99%

Neutral poly- and perfluoroalkyl substances in air and seawater of the North Sea

Xie¹,

Zhao

Møller

et al. 2013

Environ Sci Pollut Res

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“…Aeration is achieved by pumping ambient air into the headspace when the oxygen content is below 10%. One or two C18 SPE cartridges were inserted into the headspace as the conduit and to capture volatile parent and potential volatile transformation products [25,27]. To mimic continuous exchange of PFASs in surface soil or active sludge with surrounding air, flow-through systems using purge-and-trap methods were used to study 6:2 FTOH and 6:2 polyfluoroalkylphosphate biotransformation [26,28].…”

Section: Test Systemmentioning

confidence: 99%

“…For example, biotransformation of fluorotelomer-based substances often involves cleavage of functional groups (e.g., ester, ether, urethane) to form FTOHs, which are then further converted to FT aldehyde (FTAL), FT unsaturated carboxylic acids (FTUCAs), FT ketone and FT secondary alcohol (sFTOH), and x:3 fluorotelomer acids (F(CF2)nCH2CH2COOH, n = 3-7) [23,24]. Sediment/soil-bound residues formed from precursors and related transformation products with highly absorptive properties (e.g., FTOHs and x:3 acids) are not quantifiable without optimized sampleextraction methods and proper analytical procedures [25,26]. Furthermore, sophisticated analytical instrumentation, such as highresolution mass spectrometry (HRMS), is often needed to identify low levels of potential novel transformation products.…”

Section: Introductionmentioning

confidence: 99%

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Ruan

Lin

Wang

et al. 2015

TrAC Trends in Analytical Chemistry

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A B S T R A C TBiotransformation of polyfluoroalkyl precursors contributes in part to the perfluoroalkyl carboxylates and sulfonates detected in the global environment and biota. Robust sample preparation and sensitive analytical techniques for maximum analyte recovery are essential to identify and to quantify biotransformation products often present at low levels in environmental matrices and experimental systems. This critical review covers current sample-preparation and analytical methods, including extraction, concentration, clean-up and derivatization, mass spectrometry coupled to gas or liquid chromatography, and radioisotope labeling and tracking techniques. We also critically review methodologies for molecular structural elucidation and in-silico prediction of potential transformation products. We describe current knowledge gaps and challenges in studying novel alternative polyfluoroalkyl substances. We discuss future trends on utilizing advanced analytical techniques.

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“…PFHpA identity was confirmed by high-resolution mass spectrometry analysis along with other transformation products (see Figure SI-2 of the Supporting Information). It is worth noting that PFHpA was not detected in soil, sediment, and activated sludge dosed with 6:2 FTOH or 6:2 FTSA [F(CF 2 )CH 2 CH 2 SO 3 ], [19][20][21]24 further confirming that PFHpA did not come from 6:2 FTOH biotransformation. Even-number PFBA was not observed, and PFHxA accounted for 3.8 mol % by day 91 ( Figure 3B and Table 1), less than half of that in soil dosed with 6:2 FTOH.…”

Section: ■ Results and Discussionmentioning

confidence: 80%

“…The decreased 5:3 acid level after day 14 may reflect increased tendency for 5:3 acid to be bound to soil and was therefore more difficult to recover even with solvent extraction and postprocessing with base extraction and EnviCarb cleanup procedures. 20,35 Transient polyfluoroalkyl acids, such as 6:2 FTCA, 6:2 FTUCA, and 5:3 Uacid, were detected at low concentrations during 6:2 FTI biotransformation in soil ( Figure 3C), likely because of their fast further degradation to downstream biotransformation products, as was observed in 6:2 FTOHdosed soil. 19 Low levels of 6:2 FTOH (<1 mol %) were observed from days 1 to 58 in soil dosed with 6:2 FTI because of 6:2 FTOH subsequent rapid biotransformation.…”

Section: ■ Results and Discussionmentioning

confidence: 85%

Aerobic Soil Biotransformation of 6:2 Fluorotelomer Iodide

Ruan

Szostek

Folsom

et al. 2013

Environ. Sci. Technol.

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6:2 FTI [F(CF 2 ) 6 CH 2 CH 2 I] is a principal industrial raw material used to manufacture 6:2 FTOH [F(CF 2 ) 6 CH 2 CH 2 OH] and 6:2 FTOH-based products and could enter aerobic environments from possible industrial emissions where it is manufactured. This is the first study to assess 6:2 FTI aerobic soil biotransformation, quantify transformation products, and elucidate its biotransformation pathways. 6:2 FTI biotransformation led to 6:2 FTOH as a key intermediate, which was subsequently biotransformed to other significant transformation products, including PFPeA [F-(CF 2 ) 4 COOH, 20 mol % at day 91], 5:3 acid [F-(CF 2 ) 5 CH 2 CH 2 COOH, 16 mol %], PFHxA [F(CF 2 ) 5 COOH, 3.8 mol %], and 4:3 acid [F(CF 2 ) 4 CH 2 CH 2 COOH, 3.0 mol %]. 6:2 FTI biotransformation also led to a significant level of PFHpA [F(CF 2 ) 6 COOH, 16 mol % at day 91], perhaps via another putative intermediate, 6:2 FTUI [F(CF 2 ) 6 CHCHI],whose molecular identity and further biotransformation were not verified because of the lack of an authentic standard. Total recovery of the aforementioned per-and polyfluorocarboxylates accounted for 59 mol % of initially applied 6:2 FTI by day 91, in comparison to 56 mol % when soil was dosed with 6:2 FTOH, which did not lead to PFHpA. Thus, were 6:2 FTI to be released from its manufacture and undergo soil microbial biotransformation, it could form PFPeA, PFHpA, PFHxA, 5:3 acid, and 4:3 acid in the environment.

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6:2 Fluorotelomer alcohol biotransformation in an aerobic river sediment system

Cited by 83 publications

References 31 publications

Neutral poly- and perfluoroalkyl substances in air and seawater of the North Sea

Neutral poly- and perfluoroalkyl substances in air and seawater of the North Sea

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Aerobic Soil Biotransformation of 6:2 Fluorotelomer Iodide

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