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Fluorotelomer

April 11, 2024

Fluorotelomers are fluorocarbon-based oligomers, or telomers, synthesized by telomerization.[1] Some fluorotelomers and fluorotelomer-based compounds are a source of environmentally persistent perfluorinated carboxylic acids such as PFOA and PFNA, while others are under extended investigation.

Types edit

There are many broad categories of fluorotelomers:[2][3][4]

  • Fluorotelomer alcohols (FTOH)
  • Fluorotelomer ethoxylates (FTEO)
  • Fluorotelomer fumarates
  • Fluorotelomer methacrylates (FTMAC)
  • Fluorotelomer sulphonates (FTS)

Manufacture edit

In the radical telomerization of fluorotelomer molecules, a variety of fluorinated alkenes can serve as unsaturated taxogens including tetrafluoroethylene, vinylidene fluoride, chlorotrifluoroethylene, and hexafluoropropene. However, many fluorotelomers, such as fluorotelomer alcohols, are fluorocarbon-based because they are synthesized from tetrafluoroethylene. In addition to alcohols, synthetic products include fluorotelomer iodides, olefins, and acrylate monomer.[5] Polymerized acrylate from iodide and alcohol monomers represent >80% of the global manufacture and use of fluorotelomer-based products.[5]

 
General (simplified) synthetis route of fluorotelomer-based urethane side-chain fluorinated polymers (SCFPs)[6]

Applications edit

Fluorotelomers are used in fire-fighting foams, grease-resistant food packaging, leather protectants and stain-resistant carpeting, textiles, anti-fogging sprays and wipes.[7] Fluorotelomers are applied to food contact papers for their lipophobicity, making paper resistant to absorbing oil from fatty foods.[8] Fluorotelomer coatings are used in microwave popcorn bags, fast food wrappers, candy wrappers, and pizza box liners.[9][2]

Environmental and health concerns edit

Fluorotelomers that contain PFOA precursors can be metabolized into, and degrade to, PFOA,[10][11] a persistent global contaminant found in people in the low-parts per billion range.[12] Toxicologists estimate microwave popcorn, because of the high heat and coated bag, could account for about 20% of the PFOA levels measured in an individual consuming 10 bags a year if 1% of the fluorotelomers are metabolized to PFOA.[13]

PFOA is also formed as an unintended byproduct in the production of fluorotelomers,[14] and is thus present in finished goods treated with fluorotelomers, including those intended for food contact. In a U.S. Food and Drug Administration (USFDA) study, fluorotelomer-based paper coatings (which can be applied to food contact paper in the concentration range of 0.4%) were found to contain 88,000–160,000 parts per billion PFOA, while microwave popcorn bags contained 6–290 parts per billion PFOA.[8]

Industry and government actions edit

In 2002 Burger King stopped using fluorotelomer coated boxes.[15]

After more than a year of negotiating with "telomer makers Asahi Glass, Clariant, Daikin America, and DuPont to perform degradation studies on 13 of their products", the U.S. Environmental Protection Agency (USEPA) and companies were not able to agree on terms.[16] Thus, in late June 2004 the USEPA announced it would perform the degradation studies itself, with an expected time to complete the studies of 1 year.[16] However, in a December 2005 deal with the USEPA over alleged withholdings, DuPont agreed to test nine of its fluorotelomer-based products' potential to break down into PFOA by 27 December 2008.[17] Yet, in late December 2008, the USEPA and DuPont filed a joint motion stating that DuPont needed additional time[17] to purify the products.[7] USEPA lawyers extended the deadline by three years, to 27 December 2011, in the last month of the Bush administration.[17]

In 2009 a 546-day USEPA study was published that estimated a degradation half-life for a fluorotelomer-based polymer in the range of 10–17 years.[18] This estimate was much shorter than the half-life estimated by a DuPont study.[19] Given this discrepancy, the USEPA undertook an extensive effort to develop methods for testing the degradation rate of commercial fluorotelomer-based polymers.[20] The USEPA then carried out studies with two DuPont polymers in four soils and water using these methods. These new studies reported half-life ranges for these commercial fluorotelomer-based polymers of 33 to 112 years, roughly consistent with EPA's 2009 estimate.[10][11]

References edit

  1. ^ Lehmler, HJ (March 2005). "Synthesis of environmentally relevant fluorinated surfactants—a review". Chemosphere. 58 (11): 1471–96. Bibcode:2005Chmsp..58.1471L. doi:10.1016/j.chemosphere.2004.11.078. PMID 15694468.
  2. ^ a b Oladipo, Gloria (5 January 2022). "High levels of toxic 'forever chemicals' found in anti-fogging sprays and wipes". The Guardian. Retrieved 5 January 2022.
  3. ^ van Hees, Patrick. "Analysis of the unknown pool of PFAS: Total Oxidizable Precursors (TOP), PFOS Precursor (PreFOS) and Telomer Degradation" (PDF). Eurofins. Retrieved 5 January 2022.
  4. ^ Herkert, Nicholas J.; Kassotis, Christopher D.; Zhang, Sharon; Han, Yuling; Pulikkal, Vivek Francis; Sun, Mei; Ferguson, P. Lee; Stapleton, Heather M. (5 January 2022). "Characterization of Per- and Polyfluorinated Alkyl Substances Present in Commercial Anti-fog Products and Their In Vitro Adipogenic Activity". Environmental Science & Technology. 56 (2): 1162–1173. Bibcode:2022EnST...56.1162H. doi:10.1021/acs.est.1c06990. PMC 8908479. PMID 34985261.
  5. ^ a b Prevedouros K, Cousins IT, Buck RC, Korzeniowski SH (January 2006). "Sources, fate and transport of perfluorocarboxylates". Environ Sci Technol. 40 (1): 32–44. Bibcode:2006EnST...40...32P. doi:10.1021/es0512475. PMID 16433330.
  6. ^ Synthesis Report on Understanding Side-Chain Fluorinated Polymers and Their Life Cycle (PDF). OECD. 2022.
  7. ^ a b Eder, Andrew (10 February 2009). "DuPont gets more time to test PFOA". Delaware Online.
  8. ^ a b Begley TH, White K, Honigfort P, Twaroski ML, Neches R, Walker RA (October 2005). "Perfluorochemicals: potential sources of and migration from food packaging". Food Addit Contam. 22 (10): 1023–31. doi:10.1080/02652030500183474. PMID 16227186. S2CID 44370267.
  9. ^ Weise, Elizabeth (16 November 2005). "Engineer: DuPont hid facts about paper coating". USA Today. Retrieved 19 September 2008.
  10. ^ a b Washington JW, Jenkins TM, Rankin K, Naile JE (2015). "Decades-Scale Degradation of Commercial, Side-Chain, Fluorotelomer-based Polymers in Soils & Water". Environ. Sci. Technol. 49 (2): 915–923. Bibcode:2015EnST...49..915W. doi:10.1021/es504347u. PMID 25426868.
  11. ^ a b Washington JW, Jenkins TM (2015). "Abiotic hydrolysis of fluorotelomer polymers as a source of perfluorocarboxylates at the global scale". Environ. Sci. Technol. 49 (24): 14129–14135. doi:10.1021/acs.est.5b03686. PMID 26526296.
  12. ^ Houde M, Martin JW, Letcher RJ, Solomon KR, Muir DC (June 2006). "Biological monitoring of polyfluoroalkyl substances: A review". Environ. Sci. Technol. 40 (11): 3463–73. Bibcode:2006EnST...40.3463H. doi:10.1021/es052580b. PMID 16786681.
  13. ^ Renner, Rebecca (January 2006). "It's in the microwave popcorn, not the Teflon pan". Environ Sci Technol. 40 (1): 4. Bibcode:2006EnST...40....4R. doi:10.1021/es062599u.
  14. ^ "Information on PFOA". DuPont. Retrieved 14 February 2009.
  15. ^ Sanford Lewis. "The Shareholder’s Right To Know More - 2007 Update: DuPont’s Market and Liability Exposures Continue from PFOA and Related Issues"[permanent dead link] DuPont Shareholders For Fair Value, April 2007. (Accessed September 10, 2008).
  16. ^ a b Cheryl Hogue (July 2004). "Fluorotelomers to the test: Unable to strike deal with industry, EPA to study degradation of chemicals". Chemical & Engineering News. 82 (27): 6. doi:10.1021/cen-v082n027.p006.
  17. ^ a b c Ward, Jr., Ken (7 February 2009). . The Charleston Gazette. Archived from the original on 16 July 2011. Retrieved 20 February 2009.
  18. ^ Washington JW, Ellington J, Jenkins TM, Evans JJ, Yoo H, Hafner SC (September 2009). "Degradability of an acrylate-linked, fluorotelomer polymer in soil". Environ. Sci. Technol. 43 (17): 6617–23. Bibcode:2009EnST...43.6617W. doi:10.1021/es9002668. PMID 19764226.
  19. ^ Renner R (September 2009). "Perfluoropolymer degrades in decades, study estimates". Environ. Sci. Technol. 43 (17): 6445. Bibcode:2009EnST...43.6445R. doi:10.1021/es9021238. PMID 19764197.
  20. ^ Washington JW, Naile JE, Jenkins TM, Lynch DG (2014). "Characterizing fluorotelomer & polyfluoroalkyl substances in new & aged fluorotelomer-based polymers for degradation studies with GC/MS & LC/MS/MS". Environ. Sci. Technol. 48 (10): 5762–69. doi:10.1021/es500373b. PMID 24749955.

External links edit

  • Perfluorooctanoic Acid (PFOA); Fluorinated Telomers enforceable consent agreement development

April 11, 2024
fluorotelomer, fluorocarbon, based, oligomers, telomers, synthesized, telomerization, some, fluorotelomers, fluorotelomer, based, compounds, source, environmentally, persistent, perfluorinated, carboxylic, acids, such, pfoa, pfna, while, others, under, extende. Fluorotelomers are fluorocarbon based oligomers or telomers synthesized by telomerization 1 Some fluorotelomers and fluorotelomer based compounds are a source of environmentally persistent perfluorinated carboxylic acids such as PFOA and PFNA while others are under extended investigation Contents 1 Types 2 Manufacture 3 Applications 4 Environmental and health concerns 5 Industry and government actions 6 References 7 External linksTypes editThere are many broad categories of fluorotelomers 2 3 4 Fluorotelomer alcohols FTOH Fluorotelomer ethoxylates FTEO Fluorotelomer fumarates Fluorotelomer methacrylates FTMAC Fluorotelomer sulphonates FTS Manufacture editIn the radical telomerization of fluorotelomer molecules a variety of fluorinated alkenes can serve as unsaturated taxogens including tetrafluoroethylene vinylidene fluoride chlorotrifluoroethylene and hexafluoropropene However many fluorotelomers such as fluorotelomer alcohols are fluorocarbon based because they are synthesized from tetrafluoroethylene In addition to alcohols synthetic products include fluorotelomer iodides olefins and acrylate monomer 5 Polymerized acrylate from iodide and alcohol monomers represent gt 80 of the global manufacture and use of fluorotelomer based products 5 nbsp General simplified synthetis route of fluorotelomer based urethane side chain fluorinated polymers SCFPs 6 Applications editFluorotelomers are used in fire fighting foams grease resistant food packaging leather protectants and stain resistant carpeting textiles anti fogging sprays and wipes 7 Fluorotelomers are applied to food contact papers for their lipophobicity making paper resistant to absorbing oil from fatty foods 8 Fluorotelomer coatings are used in microwave popcorn bags fast food wrappers candy wrappers and pizza box liners 9 2 Environmental and health concerns editFluorotelomers that contain PFOA precursors can be metabolized into and degrade to PFOA 10 11 a persistent global contaminant found in people in the low parts per billion range 12 Toxicologists estimate microwave popcorn because of the high heat and coated bag could account for about 20 of the PFOA levels measured in an individual consuming 10 bags a year if 1 of the fluorotelomers are metabolized to PFOA 13 PFOA is also formed as an unintended byproduct in the production of fluorotelomers 14 and is thus present in finished goods treated with fluorotelomers including those intended for food contact In a U S Food and Drug Administration USFDA study fluorotelomer based paper coatings which can be applied to food contact paper in the concentration range of 0 4 were found to contain 88 000 160 000 parts per billion PFOA while microwave popcorn bags contained 6 290 parts per billion PFOA 8 Industry and government actions editIn 2002 Burger King stopped using fluorotelomer coated boxes 15 After more than a year of negotiating with telomer makers Asahi Glass Clariant Daikin America and DuPont to perform degradation studies on 13 of their products the U S Environmental Protection Agency USEPA and companies were not able to agree on terms 16 Thus in late June 2004 the USEPA announced it would perform the degradation studies itself with an expected time to complete the studies of 1 year 16 However in a December 2005 deal with the USEPA over alleged withholdings DuPont agreed to test nine of its fluorotelomer based products potential to break down into PFOA by 27 December 2008 17 Yet in late December 2008 the USEPA and DuPont filed a joint motion stating that DuPont needed additional time 17 to purify the products 7 USEPA lawyers extended the deadline by three years to 27 December 2011 in the last month of the Bush administration 17 In 2009 a 546 day USEPA study was published that estimated a degradation half life for a fluorotelomer based polymer in the range of 10 17 years 18 This estimate was much shorter than the half life estimated by a DuPont study 19 Given this discrepancy the USEPA undertook an extensive effort to develop methods for testing the degradation rate of commercial fluorotelomer based polymers 20 The USEPA then carried out studies with two DuPont polymers in four soils and water using these methods These new studies reported half life ranges for these commercial fluorotelomer based polymers of 33 to 112 years roughly consistent with EPA s 2009 estimate 10 11 References edit Lehmler HJ March 2005 Synthesis of environmentally relevant fluorinated surfactants a review Chemosphere 58 11 1471 96 Bibcode 2005Chmsp 58 1471L doi 10 1016 j chemosphere 2004 11 078 PMID 15694468 a b Oladipo Gloria 5 January 2022 High levels of toxic forever chemicals found in anti fogging sprays and wipes The Guardian Retrieved 5 January 2022 van Hees Patrick Analysis of the unknown pool of PFAS Total Oxidizable Precursors TOP PFOS Precursor PreFOS and Telomer Degradation PDF Eurofins Retrieved 5 January 2022 Herkert Nicholas J Kassotis Christopher D Zhang Sharon Han Yuling Pulikkal Vivek Francis Sun Mei Ferguson P Lee Stapleton Heather M 5 January 2022 Characterization of Per and Polyfluorinated Alkyl Substances Present in Commercial Anti fog Products and Their In Vitro Adipogenic Activity Environmental Science amp Technology 56 2 1162 1173 Bibcode 2022EnST 56 1162H doi 10 1021 acs est 1c06990 PMC 8908479 PMID 34985261 a b Prevedouros K Cousins IT Buck RC Korzeniowski SH January 2006 Sources fate and transport of perfluorocarboxylates Environ Sci Technol 40 1 32 44 Bibcode 2006EnST 40 32P doi 10 1021 es0512475 PMID 16433330 Synthesis Report on Understanding Side Chain Fluorinated Polymers and Their Life Cycle PDF OECD 2022 a b Eder Andrew 10 February 2009 DuPont gets more time to test PFOA Delaware Online a b Begley TH White K Honigfort P Twaroski ML Neches R Walker RA October 2005 Perfluorochemicals potential sources of and migration from food packaging Food Addit Contam 22 10 1023 31 doi 10 1080 02652030500183474 PMID 16227186 S2CID 44370267 Weise Elizabeth 16 November 2005 Engineer DuPont hid facts about paper coating USA Today Retrieved 19 September 2008 a b Washington JW Jenkins TM Rankin K Naile JE 2015 Decades Scale Degradation of Commercial Side Chain Fluorotelomer based Polymers in Soils amp Water Environ Sci Technol 49 2 915 923 Bibcode 2015EnST 49 915W doi 10 1021 es504347u PMID 25426868 a b Washington JW Jenkins TM 2015 Abiotic hydrolysis of fluorotelomer polymers as a source of perfluorocarboxylates at the global scale Environ Sci Technol 49 24 14129 14135 doi 10 1021 acs est 5b03686 PMID 26526296 Houde M Martin JW Letcher RJ Solomon KR Muir DC June 2006 Biological monitoring of polyfluoroalkyl substances A review Environ Sci Technol 40 11 3463 73 Bibcode 2006EnST 40 3463H doi 10 1021 es052580b PMID 16786681 Renner Rebecca January 2006 It s in the microwave popcorn not the Teflon pan Environ Sci Technol 40 1 4 Bibcode 2006EnST 40 4R doi 10 1021 es062599u Information on PFOA DuPont Retrieved 14 February 2009 Sanford Lewis The Shareholder s Right To Know More 2007 Update DuPont s Market and Liability Exposures Continue from PFOA and Related Issues permanent dead link DuPont Shareholders For Fair Value April 2007 Accessed September 10 2008 a b Cheryl Hogue July 2004 Fluorotelomers to the test Unable to strike deal with industry EPA to study degradation of chemicals Chemical amp Engineering News 82 27 6 doi 10 1021 cen v082n027 p006 a b c Ward Jr Ken 7 February 2009 Bush EPA gave DuPont more time on key PFOA tests The Charleston Gazette Archived from the original on 16 July 2011 Retrieved 20 February 2009 Washington JW Ellington J Jenkins TM Evans JJ Yoo H Hafner SC September 2009 Degradability of an acrylate linked fluorotelomer polymer in soil Environ Sci Technol 43 17 6617 23 Bibcode 2009EnST 43 6617W doi 10 1021 es9002668 PMID 19764226 Renner R September 2009 Perfluoropolymer degrades in decades study estimates Environ Sci Technol 43 17 6445 Bibcode 2009EnST 43 6445R doi 10 1021 es9021238 PMID 19764197 Washington JW Naile JE Jenkins TM Lynch DG 2014 Characterizing fluorotelomer amp polyfluoroalkyl substances in new amp aged fluorotelomer based polymers for degradation studies with GC MS amp LC MS MS Environ Sci Technol 48 10 5762 69 doi 10 1021 es500373b PMID 24749955 External links editPerfluorooctanoic Acid PFOA Fluorinated Telomers enforceable consent agreement development Retrieved from https en wikipedia org w index php title Fluorotelomer amp oldid 1185559771, wikipedia, wiki, book, books, library,

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