Biotransformation of AFFF Component 6:2 Fluorotelomer Thioether Amido Sulfonate Generates 6:2 Fluorotelomer Thioether Carboxylate under Sulfate-Reducing Conditions

Yi, Shan; Harding-Marjanovic, Katie C.; Houtz, Erika F.; Gao, Ying; Lawrence, Jennifer E.; Nichiporuk, Rita V.; Iavarone, Anthony T.; Zhuang, Wei-Qin; Hansen, Martin; Field, Jennifer A.; Sedlak, David L.; Alvarez-Cohen, Lisa

doi:10.1021/acs.estlett.8b00148

Title: Biotransformation of AFFF Component 6:2 Fluorotelomer Thioether Amido Sulfonate Generates 6:2 Fluorotelomer Thioether Carboxylate under Sulfate-Reducing Conditions

Full Record
Other Related Research

Abstract

The fate of per- and polyfluoroalkyl substances (PFASs) in aqueous film-forming foams (AFFFs) under anaerobic conditions has not been well characterized, leaving major gaps in our understanding of PFAS fate and transformation at contaminated sites. In this study, the biotransformation of 6:2 fluorotelomer thioether amido sulfonate (6:2 FtTAoS), a component of several AFFF formulations, was investigated under sulfate-reducing conditions in microcosms inoculated with either pristine or AFFF-impacted solids. To identify the transformation products, we used high-resolution mass spectrometry and employed suspect-screening and nontargeted compound identification methods. These analyses demonstrated that 6:2 FtTAoS was transformed primarily to a stable polyfluoroalkyl compound, 6:2 fluorotelomer thioether propionate (6:2 FtTP). It did not undergo further reactions to produce the perfluoroalkyl carboxylates and fluorotelomer sulfonates and carboxylates that were observed during aerobic transformations. Here, the 6:2 FtTP was recalcitrant to biotransformation, indicating the stability of the thioether group under sulfate-reducing conditions. The total oxidizable precursor (TOP) assay was used to assess the presence of other PFASs. Although nearly all of the PFAS mass initially present was recovered from the pristine microcosms, only 67% of the initial PFAS mass was recovered from the contaminated microcosms, suggesting the formation of volatile biotransformation products or those that couldmore » not be detected by the TOP assay.« less

Authors:

^[1]; Harding-Marjanovic, Katie C. ^[2]; Houtz, Erika F. ^[3]; Gao, Ying ^[4]; Lawrence, Jennifer E. ^[1]; Nichiporuk, Rita V. ^[1]; Iavarone, Anthony T. ^[1]; Zhuang, Wei-Qin ^[5];

^[6]; Field, Jennifer A. ^[7];

^[1]; Alvarez-Cohen, Lisa ^[8]

Univ. of California, Berkeley, CA (United States)
Exponent, Pasadena, CA (United States)
Arcadis, San Francisco, CA (United States)
Chinese Academy of Forestry, Beijing (China)
Univ. of Auckland (New Zealand)
Aarhus Univ. (Denmark)
Oregon State Univ., Corvallis, OR (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)

Publication Date:: Wed Apr 04 00:00:00 EDT 2018

Research Org.:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Org.:: USDOE Office of Science (SC)

OSTI Identifier:: 1479405

Grant/Contract Number:: AC02-05CH11231

Resource Type:: Accepted Manuscript

Journal Name:: Environmental Science & Technology Letters (Online)

Additional Journal Information:: Journal Name: Environmental Science & Technology Letters (Online); Journal Volume: 5; Journal Issue: 5; Journal ID: ISSN 2328-8930

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

Subject:: 54 ENVIRONMENTAL SCIENCES

Citation Formats


                    Yi, Shan, Harding-Marjanovic, Katie C., Houtz, Erika F., Gao, Ying, Lawrence, Jennifer E., Nichiporuk, Rita V., Iavarone, Anthony T., Zhuang, Wei-Qin, Hansen, Martin, Field, Jennifer A., Sedlak, David L., and Alvarez-Cohen, Lisa. Biotransformation of AFFF Component 6:2 Fluorotelomer Thioether Amido Sulfonate Generates 6:2 Fluorotelomer Thioether Carboxylate under Sulfate-Reducing Conditions.  United States: N. p., 2018. 
Web.  doi:10.1021/acs.estlett.8b00148.

Copy to clipboard


                    Yi, Shan, Harding-Marjanovic, Katie C., Houtz, Erika F., Gao, Ying, Lawrence, Jennifer E., Nichiporuk, Rita V., Iavarone, Anthony T., Zhuang, Wei-Qin, Hansen, Martin, Field, Jennifer A., Sedlak, David L., & Alvarez-Cohen, Lisa. Biotransformation of AFFF Component 6:2 Fluorotelomer Thioether Amido Sulfonate Generates 6:2 Fluorotelomer Thioether Carboxylate under Sulfate-Reducing Conditions.  United States.  https://doi.org/10.1021/acs.estlett.8b00148

Copy to clipboard


                    Yi, Shan, Harding-Marjanovic, Katie C., Houtz, Erika F., Gao, Ying, Lawrence, Jennifer E., Nichiporuk, Rita V., Iavarone, Anthony T., Zhuang, Wei-Qin, Hansen, Martin, Field, Jennifer A., Sedlak, David L., and Alvarez-Cohen, Lisa. Wed .  
"Biotransformation of AFFF Component 6:2 Fluorotelomer Thioether Amido Sulfonate Generates 6:2 Fluorotelomer Thioether Carboxylate under Sulfate-Reducing Conditions".  United States.  https://doi.org/10.1021/acs.estlett.8b00148.  https://www.osti.gov/servlets/purl/1479405.

Copy to clipboard


                    
@article{osti_1479405,

  title        = {Biotransformation of AFFF Component 6:2 Fluorotelomer Thioether Amido Sulfonate Generates 6:2 Fluorotelomer Thioether Carboxylate under Sulfate-Reducing Conditions},

  author       = {Yi, Shan and Harding-Marjanovic, Katie C. and Houtz, Erika F. and Gao, Ying and Lawrence, Jennifer E. and Nichiporuk, Rita V. and Iavarone, Anthony T. and Zhuang, Wei-Qin and Hansen, Martin and Field, Jennifer A. and Sedlak, David L. and Alvarez-Cohen, Lisa},

  abstractNote = {The fate of per- and polyfluoroalkyl substances (PFASs) in aqueous film-forming foams (AFFFs) under anaerobic conditions has not been well characterized, leaving major gaps in our understanding of PFAS fate and transformation at contaminated sites. In this study, the biotransformation of 6:2 fluorotelomer thioether amido sulfonate (6:2 FtTAoS), a component of several AFFF formulations, was investigated under sulfate-reducing conditions in microcosms inoculated with either pristine or AFFF-impacted solids. To identify the transformation products, we used high-resolution mass spectrometry and employed suspect-screening and nontargeted compound identification methods. These analyses demonstrated that 6:2 FtTAoS was transformed primarily to a stable polyfluoroalkyl compound, 6:2 fluorotelomer thioether propionate (6:2 FtTP). It did not undergo further reactions to produce the perfluoroalkyl carboxylates and fluorotelomer sulfonates and carboxylates that were observed during aerobic transformations. Here, the 6:2 FtTP was recalcitrant to biotransformation, indicating the stability of the thioether group under sulfate-reducing conditions. The total oxidizable precursor (TOP) assay was used to assess the presence of other PFASs. Although nearly all of the PFAS mass initially present was recovered from the pristine microcosms, only 67% of the initial PFAS mass was recovered from the contaminated microcosms, suggesting the formation of volatile biotransformation products or those that could not be detected by the TOP assay.},

  doi          = {10.1021/acs.estlett.8b00148},

  journal      = {Environmental Science & Technology Letters (Online)},

  number       = 5,

  volume       = 5,

  place        = {United States},

  year         = {Wed Apr 04 00:00:00 EDT 2018},

  month        = {Wed Apr 04 00:00:00 EDT 2018}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (DOE)

Publisher's Version of Record

https://doi.org/10.1021/acs.estlett.8b00148

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 36 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Similar Records in DOE PAGES and OSTI.GOV collections:

Aerobic Biotransformation of Fluorotelomer Thioether Amido Sulfonate (Lodyne) in AFFF-Amended Microcosms

Journal Article Harding-Marjanovic, Katie C. ; Houtz, Erika F. ; Yi, Shan ; ... - Environmental Science and Technology

The aerobic biotransformation pathways of 4:2, 6:2, and 8:2 fluorotelomer thioether amido sulfonate (FtTAoS) were characterized by determining the fate of the compounds in soil and medium microcosms amended with an aqueous film-forming foam (AFFF) solution. The biotransformation of FtTAoS occurred in live microcosms over approximately 40 days and produced 4:2, 6:2, and 8:2 fluorotelomer sulfonate (FtS), 6:2 fluorotelomer unsaturated carboxylic acid (FtUCA), 5:3 fluorotelomer carboxylic acid (FtCA), and C₄ to C₈ perfluorinated carboxylic acids (PFCAs). Two biotransformation products corresponding to singly and doubly oxygenated forms of 6:2 FtTAoS were also identified through high resolution mass spectrometry (MS) analysis andmore »« less
Cited by 165
https://doi.org/10.1021/acs.est.5b01219

Full Text Available
Impacts of divalent cations (Mg²⁺ and Ca²⁺) on PFAS bioaccumulation in freshwater macroinvertebrates representing different foraging modes

Journal Article Lewis, Asa J. ; Yun, Xiaoyan ; Lewis, Max G. ; ... - Environmental Pollution

Per- and polyfluoroalkyl substances (PFAS) have extensively contaminated freshwater aquatic ecosystems where they can be transported in water and partition to sediment and biota. In this paper, three freshwater benthic macroinvertebrates with different foraging modes were exposed to environmentally relevant concentrations of eight perfluoroalkyl carboxylates (PFCA), three perfluoroalkyl sulfonates (PFSA), and three fluorotelomer sulfonates (FTS) at varying divalent cation concentrations of magnesium (Mg²⁺) and calcium (Ca²⁺). Divalent cations can impact PFAS partitioning to solids, especially to sediments, at higher concentrations. Sediment dwelling worms (Lumbriculus variegatus), epibenthic grazing snails (Physella acuta), and sediment-dwelling filter-feeding bivalves (Elliptio complanata) were selected due tomore »« less
https://doi.org/10.1016/j.envpol.2023.121938
Survey of PFAS Treatment Technologies

Technical Report Lenear, Raina ; Chang, A.

Per- and polyfluoroalkyl substances (PFAS) are a group of manufactured chemicals that have caught the attention of many governmental agencies and researchers. These chemicals are highly stable and possess hydrophobic properties that lead to the widespread use of PFAS in aqueous film forming foams, and household products such as carpets, paper and non-stick cookware (Prevedouros et al., 2006). Regulatory and health advisories have focused determining a lifetime drinking water health advisory of 70 ng/L for PFOA and PFOS (USEPA, 2016). Other PFASs may be present in the environment, along with PFOA and PFOS, due to product manufacturing processes (Prevedouros etmore »« less
https://doi.org/10.2172/1650453

Full Text Available
Bioaccumulation of per- and polyfluoroalkyl substances by freshwater benthic macroinvertebrates: Impact of species and sediment organic carbon content

Journal Article Yun, Xiaoyan ; Lewis, Asa J. ; Stevens-King, Galen ; ... - Science of the Total Environment

Per- and polyfluoroalkyl substances (PFAS) in aquatic environments have caused global concern due to their persistence, toxicity, and potential bioaccumulation of some compounds. As an important compartment of the aquatic ecosystem, sediment properties impact PFAS partitioning between aqueous and solid phases, but little is known about the influence of sediment organic carbon content on PFAS bioaccumulation in benthic organisms. In this study, three freshwater benthic macroinvertebrates – worms (Lumbriculus variegatus), mussels (Elliptio complanata) and snails (Physella acuta) – were exposed for 28 days to PFAS spiked synthetic sediment equilibrated with a synthetic surface water. Using microcosms, sediment organic carbon contentmore »« less
https://doi.org/10.1016/j.scitotenv.2022.161208
Application of electron beam technology to decompose persistent emerging drinking water contaminants: poly- and perfluoroalkyl substances (PFAS) and 1,4-Dioxane

Technical Report Venkatesan, Arjun K. ; Cooper, Charles ; Paquette, Doug ; ...

Poly- and perfluoroalkyl substances (PFAS) and 1,4-dioxane are persistent emerging contaminants that are currently under consideration for federal and state-specific regulations in drinking water. Both PFAS and 1,4-dioxane are highly resistant to degradation and are not effectively removed by conventional drinking water treatment systems. Results from the Unregulated Contaminant Monitoring Rule 3 survey showed that >540 sites across the nation are contaminated with both PFAS and 1,4-dioxane. Hence, there is a need to identify technologies that can effectively remove both these contaminants. Water treatment via electron beam (e-beam) has been proven effective at treating a wide range of contaminants, includingmore »« less
https://doi.org/10.2172/1837061

Full Text Available

Similar Records