Perfluorooctanoic acid

{{short description|Perfluorinated carboxylic acid}}

{{cs1 config|name-list-style=vanc}}

{{Chembox

| Watchedfields = changed

| verifiedrevid = 464184850

| Name = Perfluorooctanoic acid

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageFile = Perfluorooctanoic acid.svg

| ImageClass = skin-invert-image

| ImageSize =

| ImageFile2 = PFOA-3D.png

| ImageClass2 = bg-transparent

| ImageFile3 = Perfluorooctanoic acid in beaker.png

| PIN = Pentadecafluorooctanoic acid

| ImageCaption3 = Perfluorooctanoic acid visible in an emulsion

| OtherNames = Perfluorooctanoic acid, PFOA, C8, Perfluorooctanoate, PFO, Perfluorocaprylic acid, C8-PFCA, FC-143, F-n-octanoic acid

| Section1 = {{Chembox Identifiers

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 35549

|SMILES = FC(F)(C(F)(F)C(=O)O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 9180

|InChI = 1/C8HF15O2/c9-2(10,1(24)25)3(11,12)4(13,14)5(15,16)6(17,18)7(19,20)8(21,22)23/h(H,24,25)

|InChIKey = SNGREZUHAYWORS-UHFFFAOYAQ

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 172988

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C8HF15O2/c9-2(10,1(24)25)3(11,12)4(13,14)5(15,16)6(17,18)7(19,20)8(21,22)23/h(H,24,25)

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = SNGREZUHAYWORS-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 335-67-1

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 947VD76D3L

|EINECS = 206-397-9

|PubChem = 9554

|RTECS = RH0781000

}}

| Section2 = {{Chembox Properties

|Formula = C8HF15O2

|MolarMass = 414.07 g/mol

|Appearance = White solid

|Density = 1.8 g/cm3{{GESTIS|ZVG=493012|CAS=335-67-1|Name=Perfluorooctanoic acid|Date=5 November 2008}}

|Solubility = Soluble, 9.5 g/L (PFO)

|Solvent = other solvents

|SolubleOther = Polar organic solvents

|MeltingPtC = 40 to 50

|MeltingPt_ref =

|BoilingPtC = 189 to 192

|BoilingPt_ref =

|pKa = ~0{{cite journal | author =Goss K. U. | title =The pKa values of PFOA and other highly fluorinated carboxylic acids | journal =Environ. Sci. Technol. | volume =42 |issue=2 |pages=456–458 |date=July 2008 | pmid =18284146 |doi=10.1021/es702192c| bibcode =2008EnST...42..456G}}{{cite journal | vauthors =Cheng J, Psillakis E, Hoffmann MR, Colussi AJ | title =Acid dissociation versus molecular association of perfluoroalkyl oxoacids: Environmental implications | journal =J. Phys. Chem. A | volume =113 | issue =29 | pages =8152–8156 | date =July 2009 | doi =10.1021/jp9051352 | pmid =19569653 | url =https://figshare.com/articles/Acid_Dissociation_versus_Molecular_Association_of_Perfluoroalkyl_Oxoacids_Environmental_Implications/2841688 | bibcode =2009JPCA..113.8152C | access-date =2019-12-04 | archive-date =2020-04-12 | archive-url =https://web.archive.org/web/20200412012725/https://figshare.com/articles/Acid_Dissociation_versus_Molecular_Association_of_Perfluoroalkyl_Oxoacids_Environmental_Implications/2841688 | url-status =live }}{{cite journal| vauthors=Rayne S, Forest K | title =Theoretical studies on the pKa values of perfluoroalkyl carboxylic acids | journal =J. Mol. Struct. (Theochem) | volume =949|issue=1–3 |pages=60–69 |date=June 2010 | doi =10.1016/j.theochem.2010.03.003}}

}}

| Section7 = {{Chembox Hazards

|ExternalSDS =

|MainHazards = Strong acid, known carcinogen and persistent organic pollutant

|GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}

|HPhrases = {{H-phrases|302|318|332|351|360|362|372}}

|PPhrases = {{P-phrases|201|202|260|261|263|264|270|271|280|281|301+312|304+312|304+340|305+351+338|308+313|310|312|314|330|405|501}}

|GHSSignalWord = danger

|NFPA-H = 3

|NFPA-F = 0

|NFPA-R = 0

}}

| Section8 = {{Chembox Related

|OtherFunction_label = compounds

|OtherFunction = {{ubli|Perfluorooctanesulfonic acid (PFOS), Perfluorononanoic acid (PFNA),Perfluorooctanesulfonamide (PFOSA), Trifluoroacetic acid (TFA)}}

}}

}}

Perfluorooctanoic acid (PFOA; conjugate base perfluorooctanoate; also known colloquially as C8, from its chemical formula C8HF15O2) is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in chemical processes and as a chemical precursor. PFOA is considered a surfactant, or fluorosurfactant, due to its chemical structure, which consists of a perfluorinated, n-heptyl "tail group" and a carboxylic acid "head group". The head group can be described as hydrophilic while the fluorocarbon tail is both hydrophobic and lipophobic.{{cite journal|author=Lemal DM|date=January 2004|title=Perspective on fluorocarbon chemistry |journal=J. Org. Chem. |volume=69 |issue=1 |pages=1–11 |doi=10.1021/jo0302556 |pmid=14703372}}

The International Agency for Research on Cancer (IARC) has classified PFOA as carcinogenic to humans.{{cite journal |vauthors=Zahm S, Bonde JP, Chiu WA, Hoppin J, Kanno J, Abdallah M, Blystone CR, Calkins MM, Dong GH, Dorman DC, Fry R, Guo H, Haug LS, Hofmann JN, Iwasaki M, Machala M, Mancini FR, Maria-Engler SS, Møller P, Ng JC, Pallardy M, Post GB, Salihovic S, Schlezinger J, Soshilov A, Steenland K, Steffensen IL, Tryndyak V, White A, Woskie S, Fletcher T, Ahmadi A, Ahmadi N, Benbrahim-Tallaa L, Bijoux W, Chittiboyina S, de Conti A, Facchin C, Madia F, Mattock H, Merdas M, Pasqual E, Suonio E, Viegas S, Zupunski L, Wedekind R, Schubauer-Berigan MK |date=November 2023 |title=Carcinogenicity of perfluorooctanoic acid and perfluorooctanesulfonic acid |journal=The Lancet. Oncology |volume=25 |issue=1 |pages=16–17 |doi=10.1016/S1470-2045(23)00622-8 |pmid=38043561 |s2cid=265571186|url=https://research.birmingham.ac.uk/en/publications/7651d868-53db-4aeb-8158-86f7c4482230 }} PFOA is one of many synthetic organofluorine compounds collectively known as per- and polyfluoroalkyl substances (PFASs). Many PFAS such as PFOS, PFOA are a concern because they do not break down via natural processes and are commonly described as persistent organic pollutants or "forever chemicals".{{Cite web |date=2022-05-03 |title=Per- and Polyfluorinated Substances (PFAS) Factsheet {{!}} National Biomonitoring Program {{!}} CDC |url=https://www.cdc.gov/biomonitoring/PFAS_FactSheet.html |access-date=2024-04-12 |website=www.cdc.gov |language=en-us |archive-date=2022-12-22 |archive-url=https://web.archive.org/web/20221222184801/https://www.cdc.gov/biomonitoring/PFAS_FactSheet.html |url-status=live }} They can also move through soils and contaminate drinking water sources and can build up (bioaccumulate) in fish and wildlife. Residues have been detected in humans and wildlife.{{Cite web |title=Emerging chemical risks in Europe — 'PFAS' — European Environment Agency |url=https://www.eea.europa.eu/publications/emerging-chemical-risks-in-europe |access-date=2024-04-12 |website=www.eea.europa.eu |date=16 December 2019 |language=en |archive-date=2024-07-12 |archive-url=https://web.archive.org/web/20240712004800/https://www.eea.europa.eu/publications/emerging-chemical-risks-in-europe |url-status=live}}

PFOA is used in several industrial applications, including carpeting, upholstery, apparel, floor wax, textiles, fire fighting foam and sealants. PFOA serves as a surfactant in the emulsion polymerization of fluoropolymers and as a chemical precursor for the synthesis of perfluoroalkyl-substituted compounds, polymers, and polymeric materials. PFOA has been manufactured since the 1940s in industrial quantities.{{cite journal |last1=Lindstrom |first1=Andrew B. |last2=Strynar |first2=Mark J. |last3=Libelo |first3=E. Laurence |date=2011-08-25 |title=Polyfluorinated Compounds: Past, Present, and Future |journal=Environ. Sci. Technol. |volume=45 |issue=19 |pages=7954–7961 |doi=10.1021/es2011622|pmid=21866930 |bibcode=2011EnST...45.7954L }} It is also formed by the degradation of precursors such as some fluorotelomers. PFOA is used as a surfactant because it can lower the surface tension of water more than hydrocarbon surfactants while having exceptional stability due to having perfluoroalkyl tail group. The stability of PFOA is desired industrially but is a cause of concern environmentally.

The primary manufacturer of perfluorooctanesulfonic acid (PFOS), 3M, began a production phase-out in 2002 in response to concerns expressed by the U.S. Environmental Protection Agency (EPA).{{rp|2}} Eight other companies agreed to gradually phase out the manufacturing of the chemical by 2015.{{rp|3}}

By 2014, EPA had listed PFOA and perfluorooctanesulfonates (salts of perfluorooctanesulfonic acid, PFOS) as emergent contaminants:

{{blockquote|PFOA and PFOS are extremely persistent in the environment and resistant to typical environmental degradation processes. [They] are widely distributed across the higher trophic levels and are found in soil, air and groundwater at sites across the United States. The toxicity, mobility and bioaccumulation potential of PFOS and PFOA pose potential adverse effects for the environment and human health.{{cite report |date=March 2014 |title=Emerging Contaminants Perfluorooctane Sulfonate (PFOS) and Perfluorooctanoic Acid (PFOA) |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100LTG6.txt |publisher=EPA |id=505-F-14-001 |access-date=2017-11-12 |archive-date=2023-10-22 |archive-url=https://web.archive.org/web/20231022044502/https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100LTG6.txt |url-status=live }} Fact sheet.{{rp|1}}}}

In 2024 EPA published drinking water regulations for PFOA and five other PFAS.United States Environmental Protection Agency (EPA), Washington, D.C. (April 26, 2024). "PFAS National Primary Drinking Water Regulation." Federal Register, {{USFR|89|32532}}

History

3M (then the Minnesota Mining and Manufacturing Company) began producing PFOA by electrochemical fluorination in 1947.{{cite journal |vauthors=Prevedouros K, Cousins IT, Buck RC, Korzeniowski SH | title =Sources, fate and transport of perfluorocarboxylates |journal=Environ. Sci. Technol. |volume=40 |issue=1 |pages=32–44 |date=January 2006 |doi =10.1021/es0512475 |pmid=16433330| bibcode =2006EnST...40...32P }} Starting in 1951, DuPont purchased PFOA from 3M for use in the manufacturing of specific fluoropolymers—commercially branded as Teflon—but DuPont internally referred to PFOA as C8.{{cite journal |vauthors=Emmett EA, Shofer FS, Zhang H, Freeman D, Desai C, Shaw LM | title =Community exposure to perfluorooctanoate: relationships between serum concentrations and exposure sources |journal=J. Occup. Environ. Med. |volume=48 |issue=8 |pages=759–70 |date=August 2006 |pmid=16902368 |pmc=3038253 |doi=10.1097/01.jom.0000232486.07658.74}}{{Cite web| series = PubChem| work = National Center for Biotechnology Information| title = Perfluorooctanoic acid| access-date = 2019-09-30| url = https://pubchem.ncbi.nlm.nih.gov/compound/9554| archive-date = 2023-05-10| archive-url = https://web.archive.org/web/20230510220839/https://pubchem.ncbi.nlm.nih.gov/compound/9554| url-status = live}}

In 1968, organofluorine content was detected in the blood serum of consumers, and in 1976 it was suggested to be PFOA or a related compound such as PFOS.{{cite journal |vauthors=Kennedy GL, Butenhoff JL, Olsen GW, etal | title =The toxicology of perfluorooctanoate |journal=Crit. Rev. Toxicol. |volume=34 |issue=4 |pages=351–84 |year=2004 |pmid =15328768 |doi=10.1080/10408440490464705| s2cid =8873920 }}{{cite journal |vauthors=Giesy JP, Kannan K |title=Perfluorochemical surfactants in the environment |journal =Environ. Sci. Technol. |volume=36 |issue=7 |pages=146A–152A |date=April 2002 |pmid =11999053 |doi=10.1021/es022253t |doi-access=free |bibcode=2002EnST...36..146G }}{{cite journal |vauthors=Lau C, Butenhoff JL, Rogers JM |title=The developmental toxicity of perfluoroalkyl acids and their derivatives |journal=Toxicol. Appl. Pharmacol. |volume=198 |issue=2 |pages=231–41 |date=July 2004 |pmid=15236955 |doi=10.1016/j.taap.2003.11.031 |bibcode=2004ToxAP.198..231L |url=https://zenodo.org/record/1259371 |access-date=2019-08-03 |archive-date=2023-04-13 |archive-url=https://web.archive.org/web/20230413101401/https://zenodo.org/record/1259371 |url-status=live }}

In 1999, EPA ordered companies to examine the effects of perfluorinated chemicals after receiving data on the global distribution and toxicity of PFOS.{{cite journal |last=Ullah |first=Aziz |title=The Fluorochemical Dilemma: What the PFOS/PFOA fuss is all about |journal=Cleaning & Restoration |date=October 2006 |url=https://www.restorationindustry.org/buyersguide/FlurochemicalsOct06.pdf |access-date=2008-09-24 |archive-date=2009-03-25 |archive-url=https://web.archive.org/web/20090325050930/https://www.restorationindustry.org/buyersguide/FlurochemicalsOct06.pdf |url-status=live }} For these reasons, and EPA pressure,{{cite news |first=Jennifer 8. |last=Lee |author-link=Jennifer 8. Lee |title=E.P.A. Orders Companies to Examine Effects of Chemicals |work=The New York Times |date=15 April 2003 |access-date=15 May 2009 |url=https://www.nytimes.com/2003/04/15/science/epa-orders-companies-to-examine-effects-of-chemicals.html?pagewanted=2 |archive-date=3 July 2021 |archive-url=https://web.archive.org/web/20210703082951/https://www.nytimes.com/2003/04/15/science/epa-orders-companies-to-examine-effects-of-chemicals.html?pagewanted=2 |url-status=live }} in May 2000, 3M announced the phaseout of the production of PFOA, PFOS, and PFOS-related products—the company's best-selling repellent.{{cite web |url=http://solutions.3m.com/wps/portal/3M/en_US/PFOS/PFOA/Information/Action |title=3M United States: PFOS PFOA: What is 3M Doing? |publisher=3M Company |access-date=2009-01-05 |url-status=dead |archive-url=https://web.archive.org/web/20141210020455/http://solutions.3m.com/wps/portal/3M/en_US/PFOS/PFOA/Information/Action |archive-date=2014-12-10 }} 3M stated that they would have made the same decision regardless of EPA pressure.{{cite journal |last=Weber |first=Joseph |title=3M's Big Cleanup – Why it decided to pull the plug on its best-selling stain repellent |journal=Business Week |issue=3684 |page=96 |date=2000-06-05}}

Because of the 3M phaseout, in 2002, DuPont built its own plant in Fayetteville, North Carolina, to manufacture the chemical.{{cite news | first=Ken Jr. | last=Ward |title=DuPont finds high C8 in Chinese workers |work=The Charleston Gazette |date=7 November 2008 |access-date=6 January 2009 |url=http://sundaygazettemail.com/News/200811060596?page=1&build=cache |archive-url=https://web.archive.org/web/20090224111523/http://sundaygazettemail.com/News/200811060596?page=1&build=cache |archive-date=2009-02-24 |url-status=dead }} The chemical has received attention due to litigation from the PFOA-contaminated community around DuPont's Washington Works facility in Washington, West Virginia, along with EPA focus. In 2004, ChemRisk—an "industry risk assessor" that had been contracted by Dupont, reported that over 1.7 million pounds of C8 had been "dumped, poured and released" into the environment from Dupont's Parkersburg, West Virginia-based Washington Works plant between 1951 and 2003.{{Cite web| last = Mordock| first = Jeff| title = Taking on DuPont: Illnesses, deaths blamed on pollution from W. Va. plant| work = Delaware Online| access-date = September 30, 2019| url = https://www.delawareonline.com/story/news/2016/04/01/dupont-illnesses-deaths-c8/81151346/| date = April 1, 2016| archive-date = December 11, 2022| archive-url = https://web.archive.org/web/20221211121120/https://www.delawareonline.com/story/news/2016/04/01/dupont-illnesses-deaths-c8/81151346/| url-status = live}}

Research on PFOA has demonstrated ubiquity, animal-based toxicity, and some associations with human health parameters and potential health effects. Additionally, advances in analytical chemistry in recent years have allowed the routine detection of low- and sub-parts per billion levels of PFOA in a variety of substances. In 2013, Gore-Tex eliminated the use of PFOAs in the manufacture of its weatherproof functional fabrics.{{cite web|url=http://news.gorefabrics.com/en_gb/enterprise/innovation/gore-completes-elimination-of-pfoa-from-raw-material-of-its-functional-fabrics/|title=GORE completes elimination of PFOA from raw material of its functional fabrics: GORE-TEX Products Newsroom|publisher=Gore Fabrics|access-date=13 August 2015|archive-date=29 March 2019|archive-url=https://web.archive.org/web/20190329225556/http://news.gorefabrics.com/en_gb/enterprise/innovation/gore-completes-elimination-of-pfoa-from-raw-material-of-its-functional-fabrics/|url-status=live}} Major companies producing PFOA signed with the Global PFOA Stewardship Program with the goal of elimination of PFOA by 2015.{{Cite web|url=https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/fact-sheet-20102015-pfoa-stewardship-program|title=Fact Sheet: 2010/2015 PFOA Stewardship Program|last=US EPA|first=OCSPP|date=2016-05-10|website=US EPA|language=en|access-date=2019-10-21|archive-date=2018-12-08|archive-url=https://web.archive.org/web/20181208160450/https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/fact-sheet-20102015-pfoa-stewardship-program|url-status=live}} Since then it has been eliminated from the production of non-stick materials used in cookware. GenX has been introduced as a replacement for PFOA, but in a 2015 study which tested the effects on rats, GenX caused many of the same health problems as PFOA, but required much higher concentrations. This is because GenX (C3) is a short chain alternative to PFOA. GenX also has a significantly shorter half-life than PFOA so it is not as bio-persistent as PFOA or other long chain perfluorinated chemicals.{{cite journal |last1=Caverly Rae |first1=JM |last2=Craig |first2=Lisa |last3=Stone |first3=Theodore W. |last4=Frame |first4=Steven R. |last5=Buxton |first5=L. William |last6=Kennedy |first6=Gerald L. |title=Evaluation of chronic toxicity and carcinogenicity of ammonium 2,3,3,3-tetrafluoro-2-(heptafluoropropoxy)-propanoate in Sprague–Dawley rats |date=2015 |journal=Toxicology Reports |volume=2 |pages=939–949 |doi=10.1016/j.toxrep.2015.06.001|pmid=28962433 |pmc=5598527 |bibcode=2015ToxR....2..939C }}

=Robert Bilott investigation=

In the Autumn of 2000, lawyer Robert Bilott, a partner at Taft Stettinius & Hollister, won a court order forcing DuPont to share all documentation related to PFOA. This included 110,000 files, consisting of confidential studies and reports conducted by DuPont scientists over decades. By 1993, DuPont understood that "PFOA caused cancerous testicular, pancreatic and liver tumors in lab animals" and the company began to investigate alternatives. However, because products manufactured with PFOA were such an integral part of DuPont's earnings, $1 billion in annual profit, they chose to continue using PFOA.{{cite news |url=https://www.nytimes.com/2016/01/10/magazine/the-lawyer-who-became-duponts-worst-nightmare.html?_r=0 |title=The Lawyer Who Became DuPont's Worst Nightmare |date=6 January 2016 |access-date=8 January 2016 |author=Rich, Nathaniel |work=New York Times |archive-date=9 January 2016 |archive-url=https://web.archive.org/web/20160109110502/http://www.nytimes.com/2016/01/10/magazine/the-lawyer-who-became-duponts-worst-nightmare.html?_r=0 |url-status=live }} Bilott learned that both "3M and DuPont had been conducting secret medical studies on PFOA for more than four decades", and by 1961 DuPont was aware of hepatomegaly in mice fed with PFOA.{{cite conference |first=Gerald J. |last=Arneson |title=Toxicity of Teflon Dispersing Agents |publisher=DuPont, Polychemicals Department, Research & Development Division, Experimental Station |date=November 1961 |url=http://www.defendingscience.org/case_studies/upload/1961-memo.pdf |access-date=2008-09-21 |archive-url=https://web.archive.org/web/20061002054129/http://www.defendingscience.org/case_studies/upload/1961-memo.pdf |archive-date=2006-10-02 |url-status=dead }}{{cite web |url=http://www.defendingscience.org/case_studies/perfluorooctanoic-acid.cfm |title=Case Studies in Science Policy: Perfluorooctanoic Acid |access-date=2008-12-19 |last=Clapp |first=Richard |author2=Polly Hoppin |author3=Jyotsna Jagai |author4=Sara Donahue |publisher=Project on Scientific Knowledge and Public Policy (SKAPP) |url-status=dead |archive-url=https://web.archive.org/web/20090301012304/http://www.defendingscience.org/case_studies/perfluorooctanoic-acid.cfm |archive-date=2009-03-01 }}

Bilott exposed how DuPont had been knowingly polluting water with PFOAs in Parkersburg, West Virginia, since the 1980s. In the 1980s and 1990s, researchers investigated the toxicity of PFOA. Regarding a secret agreement between 3M and the government of Jersey (UK) to not perform group testing of residents and to help 3M avoid a class action, Billott told The Guardian: “I’ve not seen something like this where there’s an agreement to try to help the company against claims by others, Particularly if it’s something affecting public health and safety or research.”

For his work in the exposure of the contamination, Bilott received several awards including The Right Livelihood Award in 2017.{{cite web |url=http://www.rightlivelihoodaward.org/laureates/robert-bilott/ |title=Robert Bilott, The Right Livelihood Award |publisher=The Right Livelihood Award |access-date=24 January 2018 |archive-date=6 June 2021 |archive-url=https://web.archive.org/web/20210606120115/https://www.rightlivelihoodaward.org/laureates/robert-bilott/ |url-status=live }} In film, this battle with DuPont has been depicted in the documentary The Devil We Know{{cite web |url=https://www.democracynow.org/2018/1/23/dupont_vs_the_world_chemical_giant |title=DuPont vs. the World: Chemical Giant Covered Up Health Risks of Teflon Contamination Across Globe |publisher=Democracy Now! |access-date=24 January 2018 |archive-date=16 October 2023 |archive-url=https://web.archive.org/web/20231016051026/https://www.democracynow.org/2018/1/23/dupont_vs_the_world_chemical_giant |url-status=live }} and the legal thriller Dark Waters.

Synthesis

PFOA has two main synthesis routes, electrochemical fluorination (ECF) and telomerization. The ECF route sees octanoyl chloride (the acid chloride of octanoic acid) reacted with hydrofluoric acid.{{cite encyclopedia |doi=10.1002/0471238961.0612211519012221.a01 |encyclopedia=Kirk-Othmer Encyclopedia of Chemical Technology |year=2000 |last1=Savu |first1=Patricia M. |title=Fluorinated Higher Carboxylic Acids |isbn=978-0-471-23896-6}} Multiple products are formed by ECF with the target acid fluoride F(CF2)7COF being produced as only 10–15% of the yield, while the main products are perfluorinated cyclic ether isomers, including FC-75. This acid fluoride is hydrolyzed to yield PFOA as a mixture of straight-chain (78%), terminally branched (13%), and internally branched (9%) molecules, because ECF induces rearrangements in the carbon tail of the acid chloride. ECF also results in production wastes.{{cite conference |first=Helen |last=Goeden |date=June 2008 |title=Issues and Needs for PFAA Exposure and Health Research: A State Perspective |conference=PFAA Days II |conference-url=http://pfaadays-epa.com |others=Minnesota Department of Health |location=U.S. EPA – Research Triangle Park |url=http://www.health.state.mn.us/divs/eh/hazardous/topics/pfcs/pfaapresent.pdf |access-date=2008-12-02 |url-status=dead |archive-url=https://web.archive.org/web/20110726102740/http://www.health.state.mn.us/divs/eh/hazardous/topics/pfcs/pfaapresent.pdf |archive-date=2011-07-26 }} 3M synthesized ECF PFOA at their Cottage Grove, Minnesota facility from 1947 to 2002 and was the world's largest producer. ECF production continues on a smaller scale in Europe and Asia.

PFOA is also synthesized by the telomerization represented below, where the telogen is the organoiodine compound and the taxogen is the tetrafluoroethylene.{{cite journal |last =Lehmler |first=H. J. |title=Synthesis of environmentally relevant fluorinated surfactants—a review |journal=Chemosphere |volume=58 |issue=11 |pages=1471–1496 |year=2005 |pmid=15694468 |doi=10.1016/j.chemosphere.2004.11.078 |bibcode=2005Chmsp..58.1471L }} Each step is an addition reaction where the carbon-iodine bond of the telogen is added across the carbon-carbon double bond of the unsaturated taxogen, resulting in the formation of a new telogen.

:CF3CF2I + F2C=CF2 → CF3CF2CF2CF2I

:CF3(CF2)3I + F2C=CF2 → CF3(CF2)5I

:CF3(CF2)5I + F2C=CF2 → CF3(CF2)7I

The product is oxidized by SO3 to form PFOA. Since each addition produces a new teleomer, fluorotelomers like these form with varying length chains containing an even number of carbon atoms, depending on reaction conditions. Typically, most products within will contain between two and six taxogens (that is, from CF3(CF2)5I to CF3(CF2)13I). After oxidation, distillation is used to separate PFOA from the other perfluorinated carboxylic acids. The telomerization synthesis of PFOA was pioneered by DuPont, and is not well suited to the laboratory. PFOA formed by telomerization is completely linear, in contrast to the mixture of structures formed by ECF.

Applications

PFOA has widespread applications. In 1976, PFOA was reported as a water and oil repellent "in fabrics and leather and in the production of floor waxes and waxed papers";{{cite journal |vauthors=Ylinen M, Hanhijärvi H, Peura P, Rämö O |title =Quantitative gas chromatographic determination of perfluorooctanoic acid as the benzyl ester in plasma and urine |journal =Arch. Environ. Contam. Toxicol. |volume=14 |issue=6 |pages=713–7 |date=November 1985 |pmid =4073944 |doi=10.1007/BF01055778|bibcode =1985ArECT..14..713Y |s2cid =33348790 }} however, it is believed that paper is no longer treated with perfluorinated compounds, but with fluorotelomers with less than 0.1% PFOA.{{cite web |title=PFOA in Norway TA-2354/2007 |page=6 |publisher=Norwegian Pollution Control Authority |year=2007 |url=http://www.sft.no/publikasjoner/2354/ta2354.pdf |access-date=6 April 2009 }}{{dead link|date=March 2018 |bot=InternetArchiveBot |fix-attempted=yes }} The compound is also used in "insulators for electric wires, planar etching of fused silica", fire fighting foam,{{cite web |url=http://www2.dupont.com/PFOA/en_US/ |title=Information on PFOA |publisher=DuPont |access-date=23 May 2009 |archive-date=24 May 2009 |archive-url=https://web.archive.org/web/20090524053639/http://www2.dupont.com/PFOA/en_US/ |url-status=dead }} and outdoor clothing.{{cite news |url=https://www.theguardian.com/environment/2009/oct/11/outdoor-clothing-ethical-living |title=Do environmentally friendly outdoor jackets exist? |access-date=25 October 2009 |date=11 October 2009 |last=Siegle |first=Lucy |work=The Observer |location=London |archive-date=12 July 2024 |archive-url=https://web.archive.org/web/20240712004758/https://www.theguardian.com/environment/2009/oct/11/outdoor-clothing-ethical-living |url-status=live }} As a protonated species, the acid form of PFOA was the most widely used perfluorocarboxylic acid used as a reactive intermediate in the production of fluoroacrylic esters.{{cite journal |vauthors=Kudo N, Kawashima Y | title =Toxicity and toxicokinetics of perfluorooctanoic acid in humans and animals |journal=J. Toxicol. Sci. |volume=28 |issue=2 |pages=49–57 |date=May 2003 |pmid =12820537 |doi=10.2131/jts.28.49|doi-access=free }}{{cite journal |vauthors=Kudo N, Suzuki-Nakajima E, Mitsumoto A, Kawashima Y | title =Responses of the liver to perfluorinated fatty acids with different carbon chain length in male and female mice:in relation to induction of hepatomegaly, peroxisomal beta-oxidation and microsomal 1-acylglycerophosphocholine acyltransferase |journal=Biol. Pharm. Bull. |volume=29 |issue=9 |pages=1952–7 |date=September 2006 |pmid =16946516 |doi=10.1248/bpb.29.1952|doi-access=free }}

File:ADONA-2D-skeletal.png

As a salt, its dominant use is as an emulsifier for the emulsion polymerization of fluoropolymers such as PTFE, polyvinylidene fluoride, and fluoroelastomers.{{cite conference |first=Martha |last=Sandy |title=Petition for Expedited CIC Consideration of Perfluorooctanic Acid (PFOA) |publisher=State of California, Office of Environmental Health Hazard Assessment, Cancer Toxicology and Epidemiology Section, Reproductive and Cancer Hazard Assessment Branch |url=http://www.oehha.ca.gov/Prop65/public_meetings/pdf/PFOACIC%20Slides121206.pdf |access-date=2008-09-27 |archive-date=2008-10-26 |archive-url=https://web.archive.org/web/20081026203445/http://www.oehha.ca.gov/prop65/public_meetings/pdf/PFOACIC%20Slides121206.pdf |url-status=live }}{{cite journal |vauthors=Lau C, Anitole K, Hodes C, Lai D, Pfahles-Hutchens A, Seed J | title =Perfluoroalkyl acids: a review of monitoring and toxicological findings |journal=Toxicol. Sci. |volume=99 |issue=2 |pages=366–94 |date=October 2007 |pmid=17519394 |doi=10.1093/toxsci/kfm128 |doi-access=free }} For this use, 3M subsidiary Dyneon has a replacement emulsifer{{cite journal |doi=10.1021/cen-v086n033.p026 |author=Michael McCoy |title=Dyneon Phasing Out Perfluorooctanoate |journal=Chemical & Engineering News |volume=86 |issue=46 |page=26 |date=November 2008 |url=http://pubs.acs.org/isubscribe/journals/cen/86/i46/html/8646busc7.html |access-date=2009-05-16 |archive-date=2024-07-12 |archive-url=https://web.archive.org/web/20240712004759/https://cen.acs.org/? |url-status=live |url-access=subscription }} despite DuPont stating PFOA is an "essential processing aid".{{cite web |url=http://www2.dupont.com/Teflon/en_US/keyword/pfoa.html?src=search_us_pfoa |title=Learn More About DuPont Teflon |publisher=DuPont |access-date=16 May 2009 |archive-date=28 September 2011 |archive-url=https://web.archive.org/web/20110928204123/http://www2.dupont.com/Teflon/en_US/keyword/pfoa.html?src=search_us_pfoa |url-status=dead }} In the past PFOA was used in the production of Gore-Tex{{cite journal |last =Renner |first=Rebecca |title=Concerns over common perfluorinated surfactant |journal=Environ. Sci. Technol. |volume =37 |issue=11 |pages=201A–2A |date=June 2003 |pmid=12831000 |doi=10.1021/es032467q|bibcode=2003EnST...37..201R |doi-access=free }} as it is PTFE-based. In PTFE processing, PFOA is in aqueous solution and forms micelles that contain tetrafluoroethylene and the growing polymer.{{cite encyclopedia |author1=G. Siegemund |author2=W. Schwertfeger |author3=A. Feiring |author4=B. Smart |author5=F. Behr |author6=H. Vogel |author7=B. McKusick | encyclopedia =Ullmann's Encyclopedia of Industrial Chemistry | title =Fluorine Compounds, Organic |year=2005 |publisher=Wiley-VCH |location=Weinheim}} PFOA can be used to stabilize fluoropolymer and fluoroelastomer suspensions before further industrial processing and in ion-pair reversed-phase liquid chromatography it can act as an extraction agent.{{cite journal |author=EPA |title=Premanufacture Notification Exemption for Polymers; Amendment of Polymer Exemption Rule to Exclude Certain Perfluorinated Polymers; Proposed Rule |journal=Federal Register |volume=71 |issue=44 |page=11490 |date=7 March 2006 |url=http://edocket.access.gpo.gov/2006/pdf/06-2152.pdf |access-date=17 July 2010 |archive-date=5 May 2009 |archive-url=https://web.archive.org/web/20090505003138/http://edocket.access.gpo.gov/2006/pdf/06-2152.pdf |url-status=live }} PFOA also finds uses in electronic products and as an industrial fluorosurfactant.{{cite conference |first =Jean-Louis |last =Salager |title =FIRP Booklet # 300-A: Surfactants-Types and Uses |page =44 |publisher =Universidad de los Andes Laboratory of Formulation, Interfaces Rheology, and Processes |year =2002 |url =http://nanoparticles.org/pdf/Salager-E300A.pdf |access-date =2008-09-07 |archive-date =2020-07-31 |archive-url =https://web.archive.org/web/20200731194249/http://nanoparticles.org/pdf/Salager-E300A.pdf |url-status =dead }}

In a 2009 EPA study of 116 products, purchased between March 2007 and May 2008 and found to contain at least 0.01% fluorine by weight, the concentrations of PFOA were determined. Concentrations shown below range from not detected, or ND, (with the detection limit in parentheses) to 6750 with concentrations in nanograms of PFOA per gram of sample (parts per billion) unless stated otherwise.

class="wikitable"
Product

! Range, ng/g

Pre-treated carpetingND (<1.5) to 462
Carpet-care liquids19 to 6750
Treated apparel5.4 to 161
Treated upholstery0.6 to 293
Treated home textiles3.8 to 438
Treated non-woven medical garments46 to 369
Industrial floor wax and wax removers7.5 to 44.8
Stone, tile, and wood sealants477 to 3720
Membranes for apparel0.1 to 2.5 ng/cm2
Food contact paperND (<1.5) to 4640
Dental floss/tapeND (<1.5) to 96.7
Thread sealant tapeND (<1.5) to 3490
PTFE cookwareND (<1.5) to 4.3

Global occurrence and sources

PFOA contaminates every continent.{{cite journal |author=Betts KS |title=Perfluoroalkyl acids: what is the evidence telling us? |journal=Environ. Health Perspect. |volume=115 |issue=5 |pages=A250–6 |date=May 2007 |pmid=17520044 |doi=10.1289/ehp.115-a250 |pmc =1867999}} Two of the most common types (PFOS and PFOA) were phased out of production in the United States (US) in 2002 and 2015 respectively, but are still present in some imported products. PFOA and PFOS are found in every American person's blood stream in the parts per billion range, though those concentrations have decreased by 70% for PFOA and 84% for PFOS between 1999 and 2014, which coincides with the end of the production and phase out of PFOA and PFOS in the US.{{cite web |url=http://www.mwra.com/01news/2019/2019-11-PFAS-fact-sheet.pdf |title=PFAS Fact Sheet |access-date=31 March 2020 |archive-date=6 August 2020 |archive-url=https://web.archive.org/web/20200806090038/http://www.mwra.com/01news/2019/2019-11-PFAS-fact-sheet.pdf |url-status=live }} PFOA has been detected in the central Pacific Ocean at low parts per quadrillion ranges, and at low parts per trillion (ppt) levels in coastal waters.{{cite journal |vauthors=Yamashita N, Kannan K, Taniyasu S, Horii Y, Petrick G, Gamo T | title =A global survey of perfluorinated acids in oceans |journal=Mar. Pollut. Bull. |volume=51 |issue=8–12 |pages=658–68 |year=2005 |pmid =15913661 |doi =10.1016/j.marpolbul.2005.04.026| bibcode =2005MarPB..51..658Y }} Due to the surfactant nature of PFOA, it has been found to concentrate in the top layers of ocean water.{{cite journal |last=Renner |first=Rebecca |title =Aerosols complicate PFOA picture |journal=Environ. Sci. Technol. |volume=42 |issue=11 |page=3908 |date=June 2008 |doi=10.1021/es087117o |pmid=18589941|bibcode=2008EnST...42.3908R |doi-access=free }} PFOA is detected widely in surface waters, and is present in numerous mammals, fish, and bird species. PFOA is in the blood or vital organs of Atlantic salmon, swordfish, striped mullet, gray seals, common cormorants, Alaskan polar bears, brown pelicans, sea turtles, sea eagles, Midwestern bald eagles, California sea lions and Laysan albatrosses on Sand Island, a wildlife refuge on Midway Atoll, in the middle of the North Pacific Ocean, about halfway between North America and Asia. Because PFAS are ubiquitous in households, consumer products, food, and the environment generally, some trace levels reflecting this ubiquitous broad use of these compounds will make their way into the wastewater and solid waste streams.{{cite web |title=PFAS FACTSHEET |url=https://casaweb.org/wp-content/uploads/2020/01/National-PFAS-Receivers-Factsheet.pdf |access-date=12 July 2024 |archive-date=29 February 2024 |archive-url=https://web.archive.org/web/20240229155817/https://casaweb.org/wp-content/uploads/2020/01/National-PFAS-Receivers-Factsheet.pdf |url-status=live }}

However, wildlife has much less PFOA than humans, unlike PFOS{{cite journal |vauthors=Houde M, Martin JW, Letcher RJ, Solomon KR, Muir DC |title=Biological monitoring of polyfluoroalkyl substances: A review |journal=Environ. Sci. Technol. |volume=40 |issue=11 |pages=3463–73 |date=June 2006 |pmid=16786681 |doi=10.1021/es052580b|bibcode=2006EnST...40.3463H }} and other longer perfluorinated carboxylic acids;{{cite journal |vauthors=Butt CM, Berger U, Bossi R, Tomy GT |title=Levels and trends of poly- and perfluorinated compounds in the arctic environment |journal=Sci Total Environ |volume=408 |issue=15 |pages=2936–65 |date=May 2010 |pmid=20493516 |doi=10.1016/j.scitotenv.2010.03.015|bibcode=2010ScTEn.408.2936B }} in wildlife, PFOA is not as bioaccumulative as longer perfluorinated carboxylic acids.{{cite journal |vauthors=Conder JM, Hoke RA, De Wolf W, Russell MH, Buck RC |title=Are PFCAs bioaccumulative? A critical review and comparison with regulatory criteria and persistent lipophilic compounds |journal=Environ. Sci. Technol. |volume=42 |issue=4 |pages=995–1003 |date =February 2008 |pmid=18351063 |doi=10.1021/es070895g|bibcode=2008EnST...42..995C }} Municipal wastewater and landfill leachates are considered as important sources of PFOA to the environment.{{cite journal | author = Arvaniti O.S., Stasinakis A.S. | year = 2015 | title = Review on the occurrence, fate and removal of perfluorinated compounds during wastewater treatment | journal = Science of the Total Environment | volume = 524–525 | pages = 81–92 | doi = 10.1016/j.scitotenv.2015.04.023 | bibcode = 2015ScTEn.524...81A | pmid = 25889547 }}{{cite journal | author = Nika M.C., Ntaiou K., Elytis K., Thomaidi V.S., Gatidou G., Kalantzi O.I., Thomaidis N.S., Stasinakis A.S. | year = 2020 | title = Wide-scope target analysis of emerging contaminants in landfill leachates and risk assessment using RQ methodology | url = https://www.sciencedirect.com/science/article/abs/pii/S0304389420304829 | journal = Journal of Hazardous Materials | volume = 394 | page = 122493 | doi = 10.1016/j.jhazmat.2020.122493 | pmid = 32240898 | s2cid = 214766390 | access-date = 2020-04-04 | archive-date = 2021-04-17 | archive-url = https://web.archive.org/web/20210417091055/https://www.sciencedirect.com/science/article/abs/pii/S0304389420304829 | url-status = live | url-access = subscription }}

Most industrialized nations have average PFOA blood serum levels ranging from 2 to 8 parts per billion;{{cite journal |vauthors=Vestergren R, Cousins IT |title =Tracking the pathways of human exposure to perfluorocarboxylates |journal=Environ. Sci. Technol. |volume=43 |issue=15 |pages=5565–75 |date=August 2009

| pmid =19731646 |doi=10.1021/es900228k|bibcode =2009EnST...43.5565V }} the highest consumer sub-population identified was in Korea—with about 60 parts per billion. In Peru,{{cite journal |vauthors=Calafat AM, Needham LL, Kuklenyik Z, Reidy JA, Tully JS, Aguilar-Villalobos M, Naeher LP | title =Perfluorinated chemicals in selected residents of the American continent |journal=Chemosphere |volume=63 |issue=3 |pages=490–6 |date=April 2006

|pmid=16213555 |doi=10.1016/j.chemosphere.2005.08.028| bibcode =2006Chmsp..63..490C }} Vietnam,{{cite journal |vauthors=Harada KH, Yang HR, Moon CS, Hung NN, Hitomi T, Inoue K, Niisoe T, Watanabe T, Kamiyama S, Takenaka K, Kim MY, Watanabe K, Takasuga T, Koizumi A |title=Levels of perfluorooctane sulfonate and perfluorooctanoic acid in female serum samples from Japan in 2008, Korea in 1994–2008 and Vietnam in 2007–2008 |journal=Chemosphere |volume=79 |issue=3 |pages=314–9 |date =April 2010 |pmid=20149408 |doi=10.1016/j.chemosphere.2010.01.027|bibcode=2010Chmsp..79..314H }} and Afghanistan{{cite journal |vauthors=Hemat H, Wilhelm M, Völkel W, Mosch C, Fromme H, Wittsiepe J | title =Low serum levels of perfluorooctanoic acid (PFOA), perfluorooctane sulfonate (PFOS) and perfluorohexane sulfonate (PFHxS) in children and adults from Afghanistan |journal=Sci. Total Environ. |volume=408 |issue=16 |pages=3493–5 |date=July 2010 |pmid=20471065 |doi=10.1016/j.scitotenv.2010.04.040| bibcode =2010ScTEn.408.3493H }} blood serum levels have been recorded to be below one part per billion. In 2003–2004 99.7% of Americans had detectable PFOA in their serum with an average of about 4 parts per billion,{{cite journal |vauthors=Calafat AM, Wong LY, Kuklenyik Z, Reidy JA, Needham LL |title=Polyfluoroalkyl chemicals in the U.S. population: data from the National Health and Nutrition Examination Survey (NHANES) 2003–2004 and comparisons with NHANES 1999–2000 |journal=Environ. Health Perspect. |volume=115 |issue=11 |pages=1596–602 |date=November 2007 |pmid=18007991 |pmc=2072821 |doi=10.1289/ehp.10598|bibcode=2007EnvHP.115.1596C }} and concentrations of PFOA in US serum have declined by 25% in recent years.{{cite journal |last=Renner |first=Rebecca |title=PFOS phaseout pays off |journal=Environ. Sci. Technol. |volume=42 |issue=13 |page=4618 |year=2008 |doi=10.1021/es0871614 |pmid=18677976|bibcode=2008EnST...42.4618R |doi-access=free }} Despite a decrease in PFOA, the longer perfluorinated carboxylic acid PFNA is increasing in the blood of US consumers. PFAS are also found in paper mill residuals, digestates, composts, and soils. Given the ubiquity of PFAS, and the comparative background levels which may be found in wastewater, biosolids, and leachates, setting requirements near analytical detection limits on these sources may not provide a discernable benefit to protecting public health.

= Industrial sources =

PFOA is released directly from industrial sites. For example, the estimate for the DuPont Washington Works facility is a total PFOA emissions of 80,000 pounds (lbs) in 2000 and 1,700 pounds in 2004. A 2006 study, with two of four authors being DuPont employees, estimated about 80% of historical perfluorocarboxylate emissions were released to the environment from fluoropolymer manufacture and use. PFOA can be measured in water from industrial sites other than fluorochemical plants. PFOA has also been detected in emissions from the carpet industry,{{cite news |last1=Fuchs |first1=Erin |first2=Pam |last2=Sohn |title=Study finds high levels of stain-resistance ingredient in Conasauga River |work=Chattanooga Times Free Press |date=10 February 2008 |access-date=4 October 2008 |url=http://www.timesfreepress.com/news/2008/feb/10/epa-finds-high-levels-stain-resistance-ingredient |url-status=dead |archive-url=https://web.archive.org/web/20081006075739/http://www.timesfreepress.com/news/2008/feb/10/epa-finds-high-levels-stain-resistance-ingredient |archive-date=6 October 2008 }} paper{{cite journal |vauthors=Clara M, Scheffknecht C, Scharf S, Weiss S, Gans O |title=Emissions of perfluorinated alkylated substances (PFAS) from point sources—identification of relevant branches |journal=Water Sci. Technol. |volume=58 |issue=1 |pages=59–66 |year=2008 |pmid=18653937 |doi=10.2166/wst.2008.641|doi-access=free |bibcode=2008WSTec..58...59C }} and electronics industries.{{cite journal |vauthors=Lin AY, Panchangam SC, Lo CC |title=The impact of semiconductor, electronics and optoelectronic industries on downstream perfluorinated chemical contamination in Taiwanese rivers |journal=Environ. Pollut. |volume=157 |issue=4 |pages=1365–72 |date=April 2009| pmid =19117653 |doi=10.1016/j.envpol.2008.11.033 |bibcode=2009EPoll.157.1365L }} The most important emission sources are carpet and textile protection products, as well as fire-fighting foams.{{cite web |url=https://www.bafu.admin.ch/uw-0922-e |title=Substance flow analysis for Switzerland: Perfluorinated surfactants perfluorooctanesulfonate (PFOS) and perfluorooctanoic acid (PFOA) |year=2009 |publisher=The Swiss Federal Office for the Environment (FOEN) |access-date=4 November 2010 |archive-date=12 July 2024 |archive-url=https://web.archive.org/web/20240712004809/https://www.bafu.admin.ch/bafu/en/home/topics/chemicals/publications-studies/publications/substance-flow-analysis.html |url-status=live }}

= Precursors =

File:8-2 FTOH.svg, (8:2 FTOH), degrades environmentally to PFOA]]

PFOA can form as a breakdown product from a variety of precursor molecules. In fact, the main products of the fluorotelomer industry, fluorotelomer-based polymers, have been shown to degrade to form PFOA and related compounds, with half-lives of decades, both biotically{{cite journal |vauthors=Washington JW, Jenkins TM, Rankin K, Naile JE |title=Decades-Scale Degradation of Commercial, Side-Chain, Fluorotelomer-based Polymers in Soils & Water |journal=Environ. Sci. Technol. |volume=49 |issue=2 |pages=915–923 |year=2015 |doi=10.1021/es504347u |pmid=25426868|bibcode=2015EnST...49..915W }} and by simple abiotic reaction with water.{{cite journal |vauthors=Washington JW, Jenkins TM | title =Abiotic hydrolysis of fluorotelomer polymers as a source of perfluorocarboxylates at the global scale | journal=Environ. Sci. Technol. |volume=49 | issue =24 |pages=14129–14135 |year=2015 |doi=10.1021/acs.est.5b03686 |pmid=26526296}} It has been argued that fluorotelomer-based polymers already produced might be major sources of PFOA globally for decades to come. Other precursors that degrade to PFOA include 8:2 fluorotelomer alcohol (F(CF2)8CH2CH2OH), polyfluoroalkyl phosphate surfactants (PAPS),{{cite journal |last =Renner |first=Rebecca |title =PFOA in people |journal =Environ. Sci. Technol. |volume=41 |issue=13 |pages=4497–500 |year=2007 |doi =10.1021/es0725697 |pmid=17695887|bibcode=2007EnST...41.4497R |doi-access=free }} and possibly N-EtFOSE alcohol (F(CF2)8SO2N(Et)CH2CH2OH).{{cite journal

|vauthors=D'eon JC, Hurley MD, Wallington TJ, Mabury SA |title=Atmospheric chemistry of N-methyl perfluorobutane sulfonamidoethanol, C4F9SO2N(CH3)CH2CH2OH: kinetics and mechanism of reaction with OH |journal =Environ. Sci. Technol. |volume=40 |issue=6 |pages=1862–8 |date=March 2006 |pmid =16570609 |doi=10.1021/es0520767|bibcode=2006EnST...40.1862D }} When PTFE (Teflon) is degraded by heat (pyrolysis) it can form PFOA as a minor product.{{cite journal |vauthors=Ellis DA, Mabury SA, Martin JW, Muir DC | title =Thermolysis of fluoropolymers as a potential source of halogenated organic acids in the environment |journal =Nature |volume=412 |issue=6844 |pages=321–4 |date=July 2001 |pmid=11460160 |doi=10.1038/35085548| bibcode =2001Natur.412..321E | s2cid =4405763 }}{{cite journal |vauthors=Ellis DA, Martin JW, Muir DC, Mabury SA | title =The use of 19F NMR and mass spectrometry for the elucidation of novel fluorinated acids and atmospheric fluoroacid precursors evolved in the thermolysis of fluoropolymers |journal =Analyst |volume=128 |issue=6 |pages=756–64 |date=June 2003 |pmid=12866900 |doi=10.1039/b212658c| bibcode =2003Ana...128..756E }} The Organisation for Economic Co-operation and Development (OECD) has compiled a list of 615 chemicals that have the potential to break down into perfluorocarboxylic acids (PFCA) including PFOA.{{cite conference |title=Lists of PFOS, PFAS, PFOA, PFCA, related compounds and chemicals that may degrade to PFCA |conference=Environment Directorate-Joint Meeting of the Chemicals Committee and the Working Party on Chemicals, Pesticides, and Biotechnology |others=Organisation for Economic Co-operation and Development |date=2007-08-21 |url=http://www.olis.oecd.org/olis/2006doc.nsf/LinkTo/NT00000F9A/$FILE/JT03231059.PDF |access-date=2008-09-19 |archive-date=2008-09-07 |archive-url=https://web.archive.org/web/20080907104224/http://www.olis.oecd.org/olis/2006doc.nsf/LinkTo/NT00000F9A/$FILE/JT03231059.PDF |url-status=dead }} However, not all 615 have the potential to break down to form PFOA.

A majority of waste water treatment plants (WWTPs) that have been tested output more PFOA than is input, and this increased output has been attributed to the biodegradation of fluorotelomer alcohols.{{cite journal

|vauthors=Schultz MM, Higgins CP, Huset CA, Luthy RG, Barofsky DF, Field JA | title =Fluorochemical mass flows in a municipal wastewater treatment facility |journal =Environ. Sci. Technol.

| volume =40 |issue=23 |pages=7350–7 |date=December 2006 |pmid=17180988 |pmc=2556954 |doi=10.1021/es061025m}} A current PFOA precursor concern are fluorotelomer-based polymers; fluorotelomer alcohols attached to hydrocarbon backbones via ester linkages may detach and be free to biodegrade to PFOA.{{cite journal |last=Renner |first=Rebecca |title =Do perfluoropolymers biodegrade into PFOA? |journal=Environ. Sci. Technol. |volume =42 |issue=3 |pages=648–50 |year=2008 |doi =10.1021/es087093l |pmid=18323078|bibcode=2008EnST...42..648R |doi-access=free }}

= Sources to people =

Food,{{cite journal |vauthors=Schecter A, Colacino J, Haffner D, Patel K, Opel M, Päpke O, Birnbaum L | title =Perfluorinated Compounds, Polychlorinated Biphenyl, and Organochlorine Pesticide Contamination in Composite Food Samples from Dallas, Texas | journal =Environ. Health Perspect. |volume = 118|issue= 6|pages= 796–802| year=2010 |doi=10.1289/ehp.0901347 |pmc =2898856 |pmid =20146964}} drinking water, outdoor air, indoor air,{{cite journal |vauthors=Langer V, Dreyer A, Ebinghaus R |title=Polyfluorinated compounds in residential and nonresidential indoor air |journal=Environ. Sci. Technol. |volume=44 |issue=21 |pages=8075–81 |date=November 2010 |pmid=20925396 |doi=10.1021/es102384z|bibcode=2010EnST...44.8075L }} dust, and food packagings{{cite journal |vauthors=D'eon JC, Mabury SA |title=Exploring Indirect Sources of Human Exposure to Perfluoroalkyl Carboxylates (PFCAs): Evaluating Uptake, Elimination and Biotransformation of Polyfluoroalkyl Phosphate Esters (PAPs) in the Rat |journal=Environ Health Perspect |volume= 119|issue= 3|pages= 344–350|year=2010 |pmid= 21059488|doi=10.1289/ehp.1002409 |pmc=3059997}} are all implicated as sources of PFOA to people. However, it is unclear which exposure routes dominate{{cite journal|author=Renner R|date=December 2008|title=EPA finds record PFOS, PFOA levels in Alabama grazing fields|journal=Environ. Sci. Technol.|volume=43|issue=5|pages=1245–6|doi=10.1021/es803520c|pmid=19350885|doi-access=free}} because of data gaps. When water is a source, blood levels are approximately 100 times higher than drinking water levels.{{cite web |first=Gloria |last=Post |author2=Stern, Alan |author3=Murphy, Eileen |title=Guidance for PFOA in Drinking Water at Pennsgrove Water Supply Company |url=http://www.state.nj.us/dep/watersupply/pfoa_dwguidance.pdf |publisher=New Jersey Department of Environmental Protection; Division of Science, Research and Technology |page=2 |access-date=7 June 2009 |archive-date=4 June 2011 |archive-url=https://web.archive.org/web/20110604175928/http://www.state.nj.us/dep/watersupply/pfoa_dwguidance.pdf |url-status=live }}{{cite web |first = Mark |last = Johnson |title = Evaluation of Methodologies for Deriving Health-Based Values for PFCs in Drinking Water |url = http://www.health.state.mn.us/divs/eh/hazardous/topics/pfcworkshop0507/pfcs_cdcatsdr.pdf |publisher = Agency for Toxic Substances and Disease Registry |pages = 20, 37 |access-date = 7 June 2009 |archive-url = https://web.archive.org/web/20110726103300/http://www.health.state.mn.us/divs/eh/hazardous/topics/pfcworkshop0507/pfcs_cdcatsdr.pdf |archive-date = 2011-07-26 |url-status = dead }}

People who lived in the PFOA-contaminated area around DuPont's Washington Works facility were found to have higher levels of PFOA in their blood from drinking water. The highest PFOA levels in drinking water were found in the Little Hocking water system, with an average concentration of 3.55 parts per billion during 2002–2005. Individuals who drank more tap water, ate locally grown fruits and vegetables, or ate local meat, were all associated with having higher PFOA levels. Residents who used water carbon filter systems had lower PFOA levels.

In Jersey, UK, 18% of residents of an area were found to have elevated levels of PFOA, downstream from 3M fire retardant tests in weekly fire-service practice from the 1960s to the mid 1990s. {{Cite news |last1=Hosea |first1=Leana |last2=Salvidge |first2=Rachel |date=2025-01-16 |title=Bloodletting recommended for Jersey residents after PFAS contamination |url=https://www.theguardian.com/uk-news/2025/jan/16/bloodletting-recommended-for-jersey-residents-after-pfas-contamination |access-date=2025-01-17 |work=The Guardian |language=en-GB |issn=0261-3077}} Bloodletting is used for these residents at a cost of $4500 per patient. The potatoes of the island were found to contain 10x the EU limit of PFOS.

== Food contact surfaces ==

File:Popcorn bag popped.jpgs.]]

PFOA is also formed as an unintended byproduct in the production of fluorotelomers{{cite web |url =http://www2.dupont.com/PFOA/en_US/ |title =Information on PFOA |publisher =DuPont |access-date =14 February 2009 |archive-date =24 May 2009 |archive-url =https://web.archive.org/web/20090524053639/http://www2.dupont.com/PFOA/en_US/ |url-status =dead }} and is present in finished goods treated with fluorotelomers, including those intended for food contact. Fluorotelomers are applied to food contact papers because they are lipophobic: they prevent oil from soaking into the paper from fatty foods. Also, fluorotelomers can be metabolized into PFOA.{{cite journal |last=Renner |first=Rebecca |title =It's in the microwave popcorn, not the Teflon pan |journal =Environ. Sci. Technol. |volume =40 |issue=1 |page=4 |date=January 2006 |doi =10.1021/es062599u|bibcode=2006EnST...40....4R |doi-access=free }} In a U.S. Food and Drug Administration (USFDA) study, lipophobic 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 before application, while the oil from microwave popcorn bags contained 6–290 parts per billion PFOA after heating.{{cite journal |vauthors=Begley TH, White K, Honigfort P, Twaroski ML, Neches R, Walker RA |title=Perfluorochemicals: potential sources of and migration from food packaging |journal =Food Addit. Contam. |volume=22 |issue=10 |pages=1023–31 |date=October 2005 |pmid =16227186 |doi=10.1080/02652030500183474|s2cid=44370267 }} Toxicologists estimate that microwave popcorn 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.

In 2008 as news stories began to raise concerns about PFOA in microwaved popcorn, Dan Turner, DuPont's global public relations chief, said, "I serve microwave popcorn to my three-year-old." Five years later, journalist Peter Laufer wrote to Turner to ask if his child was still eating microwave popcorn. "I am not going to comment on such a personal inquiry", Turner replied.{{cite book |last = Laufer |first=Peter |title=Organic: A Journalist's Quest to Discover the Truth behind Food Labeling |publisher=Lyons Press |year=2014 |pages=142–143 |isbn=978-0-7627-9071-5}}[https://www.linkedin.com/pub/dan-turner/0/741/100 Dan Turner, LinkedIn]{{dead link|date=October 2017}}, retrieved 9/26/15.

Fluorotelomer coatings are used in fast food wrappers, candy wrappers, and pizza box liners.{{cite news |first=Elizabeth |last=Weise |title=Engineer: DuPont hid facts about paper coating |work=USA Today |date=16 November 2005 |access-date=19 September 2008 |url=https://www.usatoday.com/money/companies/management/2005-11-16-dupont-usat_x.htm |archive-date=24 July 2008 |archive-url=https://web.archive.org/web/20080724125026/http://www.usatoday.com/money/companies/management/2005-11-16-dupont-usat_x.htm |url-status=live }} PAPS, a type of paper fluorotelomer coating, and PFOA precursor, is also used in food contact papers.

Despite DuPont's assertion that "cookware coated with DuPont Teflon non-stick coatings does not contain PFOA",{{cite news |title =Teflon firm faces fresh lawsuit |url =http://news.bbc.co.uk/2/hi/business/4697939.stm |work =BBC News |date =19 July 2005 |access-date =24 January 2009 |archive-date =29 November 2008 |archive-url =https://web.archive.org/web/20081129211034/http://news.bbc.co.uk/2/hi/business/4697939.stm |url-status =live }} residual PFOA was also detected in finished PTFE products including PTFE cookware (4–75 parts per billion). However, PFOA levels ranged from undetectable (<1.5) to 4.3 parts per billion in a more recent study.{{cite web |url=http://nepis.epa.gov/Adobe/PDF/P100EA62.pdf |vauthors=Guo Z, Liu X, Krebs KA |date=March 2009 |title=Perfluorocarboxylic Acid Content in 116 Articles of Commerce |page=40 |publisher=EPA |access-date=2013-08-24 |archive-date=2024-07-12 |archive-url=https://web.archive.org/web/20240712004802/http://nepis.epa.gov/Adobe/PDF/P100EA62.pdf |url-status=live }} Also, non-stick cookware is heated—which should volatilize PFOA; PTFE products that are not heated, such as PTFE sealant tape, had higher (1800 parts per billion) levels detected.{{cite web |title=PFOA in Norway TA-2354/2007 |page=18 |publisher=Norwegian Pollution Control Authority |year=2007 |url=http://www.sft.no/publikasjoner/2354/ta2354.pdf |access-date=29 August 2009 }}{{dead link|date=March 2018 |bot=InternetArchiveBot |fix-attempted=yes }} Overall, PTFE cookware is considered an insignificant exposure pathway to PFOA.{{cite journal |vauthors=Trudel D, Horowitz L, Wormuth M, Scheringer M, Cousins IT, Hungerbühler K | title =Estimating consumer exposure to PFOS and PFOA |journal=Risk Anal. |volume =28 |issue=2 |pages=251–69 |date=April 2008 |pmid =18419647 |doi=10.1111/j.1539-6924.2008.01017.x| bibcode =2008RiskA..28..251T | s2cid =10777081 }}{{cite web |url =http://www.consumerreports.org/cro/home-garden/kitchen/cookware-bakeware-cutlery/nonstick-pans-6-07/overview/0607_pans_ov_1.htm |title=Nonstick pans: Nonstick coating risks |work=Consumer Reports |access-date=4 July 2009}}

== Potential path: sludge to food ==

PFOA and PFOS were detected in "very high" (low parts per million) levels in agricultural fields for grazing beef cattle and crops{{cite news | first=Ken Jr. | last=Ward |title =EPA's C8 advisory does not address long-term risks |work =The Charleston Gazette |date =17 January 2009 |access-date =8 February 2009 |url =http://wvgazette.com/News/200901160363?page=1&build=cache |archive-url =https://web.archive.org/web/20110624155925/http://wvgazette.com/News/200901160363?page=1&build=cache |archive-date =2011-06-24 |url-status =dead }} around Decatur, Alabama.{{cite journal |vauthors=Washington JW, Yoo H, Ellington JJ, Jenkins TM, Libelo EL | title = Concentrations, distribution and persistence of perfluoroalkylates in sludge-applied soils near Decatur, Alabama, USA | journal=Environ. Sci. Technol. |volume=44 | issue = 22 |pages=8390–8396 |year=2010 |doi=10.1021/es1003846 |pmid=20949951| bibcode = 2010EnST...44.8390W }} The approximately 5000 acres of land were fertilized with "treated municipal sewage sludge, or biosolids". PFOA was also detected in fodder grass grown in these soils{{cite journal |vauthors=Yoo H, Washington JW, Jenkins TM, Ellington JJ | title = Quantitative determination of perfluorochemicals and fluorotelomer alcohols in plants from biosolid-amended fields using LC/MS/MS and GC/MS | journal=Environ. Sci. Technol. |volume=45 | issue = 19 |pages=7985–7990 |year=2011 |doi=10.1021/es102972m |pmid=21247105| bibcode = 2011EnST...45.7985Y }} and the blood of the cattle feeding on this grass.{{cite news |first=Scott |last=Finn |title=Bush EPA sets so-called safe level of C8 in drinking water |url=http://www.wvpubcast.org/newsarticle.aspx?id=7516 |work=West Virginia Public Broadcasting |date=15 January 2009 |access-date=18 January 2009 |archive-date=20 January 2009 |archive-url=https://web.archive.org/web/20090120100934/http://www.wvpubcast.org/newsarticle.aspx?id=7516 |url-status=dead }} The water treatment plant received process wastewater from a nearby perfluorochemical manufacturing plant. 3M says they managed their own wastes, but Daikin America "discharged process wastewater to the municipal waste treatment plant". If traced to meat, it would be the first time perfluorochemicals were traced from sludge to food. However, the USDA reported—with a detection limits of 20 parts per billion—non-detectable levels for both PFOA and PFOS in cattle muscle tissue.{{cite web |url=http://www.epa.gov/region4/water/PFCindex.html |title=Perfluorochemical Contamination of Biosolids Near Decatur, Alabama |publisher=EPA |access-date=12 June 2010 |archive-date=2 April 2010 |archive-url=https://web.archive.org/web/20100402004411/http://www.epa.gov/region4/water/PFCindex.html |url-status=live }}

== Household dust ==

PFOA is frequently found in household dust, making it an important exposure route for adults, but more substantially, children. Children have higher exposures to PFOA through dust compared to adults.{{Cite journal|last1=Haug|first1=Line S.|last2=Huber|first2=Sandra|last3=Becher|first3=Georg|last4=Thomsen|first4=Cathrine|date=May 2011|title=Characterisation of human exposure pathways to perfluorinated compounds — Comparing exposure estimates with biomarkers of exposure|journal=Environment International|volume=37|issue=4|pages=687–693|doi=10.1016/j.envint.2011.01.011|issn=0160-4120|pmid=21334069|bibcode=2011EnInt..37..687H |hdl=10852/12717 |hdl-access=free}} Hand-to-mouth contact and proximity to high concentrations of dust make them more susceptible to ingestion, and increases PFOA exposure.{{Cite journal|last1=Anderson|first1=Janet K.|last2=Luz|first2=Anthony L.|last3=Goodrum|first3=Philip|last4=Durda|first4=Judi|date=April 2019|title=Perfluorohexanoic acid toxicity, part II: Application of human health toxicity value for risk characterization|journal=Regulatory Toxicology and Pharmacology|volume=103|pages=10–20|doi=10.1016/j.yrtph.2019.01.020|pmid=30634020|issn=0273-2300|doi-access=free}} One study showed significant positive associations were recognized between dust ingestion and PFOA serum concentrations. However, an alternate study found exposure due to dust ingestion was associated with minimal risk.{{Cite journal|last1=Washburn|first1=Stephen T.|last2=Bingman|first2=Timothy S.|last3=Braithwaite|first3=Scott K.|last4=Buck|first4=Robert C.|last5=Buxton|first5=L. William|last6=Clewell|first6=Harvey J.|last7=Haroun|first7=Lynne A.|last8=Kester|first8=Janet E.|last9=Rickard|first9=Robert W.|date=June 2005|title=Exposure Assessment and Risk Characterization for Perfluorooctanoate in Selected Consumer Articles|journal=Environmental Science & Technology|volume=39|issue=11|pages=3904–3910|doi=10.1021/es048353b|pmid=15984763|issn=0013-936X|bibcode=2005EnST...39.3904W}}

==Menstrual pads==

In 2024 it was reported that a brand of menstrual pad was found to contain PFOA.{{cite web | url=http://www.theguardian.com/environment/2024/nov/02/toxic-pfas-menstrual-pads-carefree-edgewell | title=Toxic PFAS in menstrual pads harm reproductive health, advocates says | work=The Guardian | date=2 November 2024 | vauthors = Perkins T }}

Regulatory status

= Drinking water and products =

In April 2024 EPA issued a final drinking water rule for PFOA, PFOS, GenX, PFBS, PFNA, and PFHxS. Public water systems must remove these six PFAS to near-zero levels by 2027. Grant funding is available from EPA to assist utilities in water testing and development of treatment systems.{{cite news |url=https://www.nytimes.com/2024/04/10/climate/epa-pfas-drinking-water.html |title=E.P.A. Says 'Forever Chemicals' Must Be Removed From Tap Water |first=Lisa |last=Friedman | newspaper=The New York Times | date=April 10, 2024 |url-access=limited}}{{Cite news |url=https://www.nbcnews.com/health/health-news/epa-limits-pfas-chemicals-drinking-water-first-time-rcna147000 | title=EPA imposes first national limits on 'forever chemicals' in drinking water | first=Aria | last=Bendix | work=NBC News | date=April 10, 2024}}{{Cite press release |url=https://www.epa.gov/newsreleases/biden-harris-administration-finalizes-first-ever-national-drinking-water-standard | title=Biden-Harris Administration Finalizes First-Ever National Drinking Water Standard to Protect 100M People from PFAS Pollution |publisher=EPA |date=April 10, 2024}}

The State of New Jersey published drinking water standards for PFOA and PFOS in 2020.{{cite web |title=Adoption of ground water quality standards and maximum contaminant levels for perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) |url=https://www.state.nj.us/dep/srp/srra/listserv_archives/2020/20200601_srra.html |date=2020-06-01 |publisher=New Jersey Department of Environmental Protection (NJDEP) |location=Trenton, NJ |access-date=2021-02-14 |archive-date=2021-06-25 |archive-url=https://web.archive.org/web/20210625164516/https://www.state.nj.us/dep/srp/srra/listserv_archives/2020/20200601_srra.html |url-status=live }} A standard for PFNA was published in 2018. This was the first state to publish PFAS standards in the absence of federal regulations.{{cite news |last=Fallon |first=Scott |title=New Jersey becomes first state to regulate dangerous chemical PFNA in drinking water |url=https://www.northjersey.com/story/news/environment/2018/09/06/new-jersey-first-state-regulate-dangerous-chemical-pfna-pfoa/1210328002/ |date=2018-09-06 |work=North Jersey Record |location=Woodland Park, NJ |access-date=2021-02-14 |archive-date=2020-11-29 |archive-url=https://web.archive.org/web/20201129081254/https://www.northjersey.com/story/news/environment/2018/09/06/new-jersey-first-state-regulate-dangerous-chemical-pfna-pfoa/1210328002/ |url-status=live }} See U.S. state government actions.

In 2018 the State of New York adopted drinking water standards of 10 ppt for PFOA and 10 ppt for PFOS, the most stringent such standards in the United States. The standards apply to public water systems and took effect in 2019 after a public comment period.{{cite web |title=Drinking Water Quality Council Recommends Nation's Most Protective Maximum Contaminant Levels for Three Unregulated Contaminants in Drinking Water |url=https://www.health.ny.gov/press/releases/2018/2018-12-18_drinking_water_quality_council_recommendations.htm |date=2018-12-18 |publisher=New York State Department of Health |location=Albany, NY |id=Press release |access-date=2018-12-19 |archive-date=2018-12-20 |archive-url=https://web.archive.org/web/20181220231115/https://www.health.ny.gov/press/releases/2018/2018-12-18_drinking_water_quality_council_recommendations.htm |url-status=live }}

Using information gained through a Freedom of Information Act request, in May 2018 it was learned that January 2018 emails between the EPA, the Office of Management and Budget, the Department of Defense, and the Department of Health and Human Services showed an effort to suppress the release of a draft report on the toxicology of PFOS and PFOA done by the Agency for Toxic Substances and Disease Registry. The report found that these chemicals endanger human health at a far lower level than EPA has previously called safe.{{cite web|last1=Snider|first1=Annie|title=White House, EPA headed off chemical pollution study|url=https://www.politico.com/story/2018/05/14/emails-white-house-interfered-with-science-study-536950|website=Politico|date=14 May 2018|access-date=May 20, 2018|archive-date=16 May 2018|archive-url=https://web.archive.org/web/20180516023718/https://www.politico.com/story/2018/05/14/emails-white-house-interfered-with-science-study-536950|url-status=live}} After media accounts of the effort surfaced, the regional EPA administrator for Colorado denied that EPA had anything to do with suppressing the report.{{cite news |last1=Benevento |first1=Doug |title=Response to PFAS contamination is coordinated and effective |url=https://www.denverpost.com/2018/06/22/response-to-pfas-contamination-is-coordinated-and-effective/ |access-date=22 June 2018 |work=The Denver Post |date=22 June 2018 |archive-date=23 June 2018 |archive-url=https://web.archive.org/web/20180623033312/https://www.denverpost.com/2018/06/22/response-to-pfas-contamination-is-coordinated-and-effective/ |url-status=live }} The report was released on June 21, 2018.{{cite web |title=Availability of Draft Toxicological Profile: Perfluoroalkyls |url=https://www.federalregister.gov/documents/2018/06/21/2018-13385/availability-of-draft-toxicological-profile-perfluoroalkyls |website=Federal Register |access-date=22 June 2018 |date=22 June 2018 |archive-date=23 June 2018 |archive-url=https://web.archive.org/web/20180623061231/https://www.federalregister.gov/documents/2018/06/21/2018-13385/availability-of-draft-toxicological-profile-perfluoroalkyls |url-status=live }}

The new ATSDR analysis derives provisional Minimal Risk Levels (MRLs) of 3x10−6 mg/kg/day for PFOA and 2x10−6 mg/kg/day for PFOS during intermediate exposure.{{cite book |last1=Agency for Toxic Substances and Disease Registry (ATSDR) |title=Toxicological profile for Perfluoroalkyls. (Draft for Public Comment) |date=21 June 2018 |publisher=U.S. Department of Health and Human Services, Public Health Service |location=Atlanta, GA |page=34 |url=https://www.atsdr.cdc.gov/toxprofiles/tp200.pdf |access-date=22 June 2018 |archive-date=12 July 2024 |archive-url=https://web.archive.org/web/20240712004803/https://www.atsdr.cdc.gov/toxprofiles/tp200.pdf |url-status=live }} The European Food Safety Authority opinion sets a provisional tolerable weekly intake (TWI) of 6 x10−6 mg/kg body weight per week for PFOA.{{cite journal |last1=ESFA Panel on Contaminants in the Food Chain |title=Risk to human health related to the presence of perfluorooctane sulfonic acid and perfluorooctanoic acid in food |journal=EFSA Journal |date=2018 |volume=16 |issue=12 |page=5194 |doi=10.2903/j.efsa.2018.5194 |pmid=32625773 |pmc=7009575 |doi-access=free }}

= California and food packaging =

An attempt to regulate PFOA in food packaging occurred in the US state of California in 2008. A bill, sponsored by State Senator Ellen Corbett and the Environmental Working Group, was passed in the house and senate that would have banned PFOA, PFOS, and seven or more related fluorinated carbon compounds in food packaging starting in 2010,{{cite news |title=Chemical Used to Make Non-Stick Coatings Harmful to Health |work=Environment News Service |date=13 May 2008 |access-date=19 October 2008 |url=http://www.ens-newswire.com/ens/may2008/2008-05-13-093.asp |archive-date=6 July 2008 |archive-url=https://web.archive.org/web/20080706103027/http://www.ens-newswire.com/ens/may2008/2008-05-13-093.asp |url-status=live }}{{cite journal |last=Hogue |first=Cheryl |title=California Chemical Legislation: State's new laws on chemicals could presage federal action |journal=Chemical & Engineering News |volume=86 |issue=36 |page=9 |date=September 2008 |url=http://pubs.acs.org/cen/news/86/i36/8636notw5.html |access-date=2009-02-15 |archive-date=2008-10-26 |archive-url=https://web.archive.org/web/20081026095527/http://pubs.acs.org/cen/news/86/i36/8636notw5.html |url-status=live }} but the bill was vetoed by Governor Schwarzenegger.{{cite news|title=Calif. law establishes chemical review |work=San Francisco Chronicle |agency=Associated Press |date=29 September 2008 |access-date=15 February 2009 |url=http://www.sfgate.com/cgi-bin/article.cgi?f=/n/a/2008/09/29/state/n121857D71.DTL&type=health |archive-url=https://archive.today/20121209103816/http://www.sfgate.com/cgi-bin/article.cgi?f=/n/a/2008/09/29/state/n121857D71.DTL&type=health |url-status=dead |archive-date=9 December 2012 }} The bill would have affected fluorochemical manufacturers outside of the state. Schwarzenegger said the compound should be reviewed by the newly established, and more comprehensive, state program.

= Fluorotelomers =

{{Main|Fluorotelomer}}

Fluorotelomer-based products have been shown to degrade to PFOA over periods of decades; these studies could lead EPA to require DuPont and others to reformulate products with a value over $1 billion.{{cite journal |author=Stokstad E |title=Environmental research—DuPont settlement to fund test of potential toxics

|journal=Science |volume=311 |issue=5757 |pages=26–7 |date=January 2006 |pmid=16400117 |doi=10.1126/science.311.5757.26a |s2cid =45472256|doi-access=free }}

Health effects

{{medref|section|date=February 2025}}

= Toxicology =

PFOA is a possible carcinogen, a possible liver toxicant, a possible developmental toxicant, and a possible immune system toxicant, and also exerts hormonal effects including alteration of thyroid hormone levels at very high concentrations. Animal studies show developmental toxicity from reduced birth size, physical developmental delays, endocrine disruption, and neonatal mortality.{{cite journal |author=Betts K |title=PFOS and PFOA in humans: new study links prenatal exposure to lower birth weight |journal=Environ. Health Perspect. |volume=115 |issue=11 |pages=A550 |date=November 2007 |pmid=18007977 |pmc=2072861 |doi=10.1289/ehp.115-a550a}} PFOA alters lipid metabolism.

In 2008, PFOA has been described as a member of a group of "classic non-genotoxic carcinogens".{{cite journal |vauthors=Upham BL, Park JS, Babica P, Sovadinova I, Rummel AM, Trosko JE, Hirose A, Hasegawa R, Kanno J, Sai K | title =Structure-activity-dependent regulation of cell communication by perfluorinated fatty acids using in vivo and in vitro model systems |journal=Environ. Health Perspect. |volume=117 |issue=4 |pages=545–51 |date=April 2009 |pmid =19440492 |pmc=2679597 |doi=10.1289/ehp.11728| bibcode =2009EnvHP.117..545U }} However, a provisional German assessment notes that a 2005 study found PFOA to be genotoxic via a peroxisome proliferation pathway that produced oxygen radicals in HepG2 cells, and a 2006 study demonstrated the induction and suppression of a broad range of genes; therefore, it states that the indirect genotoxic (and thus carcinogenic) potential of PFOA cannot be dismissed.{{cite web |title=Assessment of PFOA in the drinking water of the German Hochsauerlandkreis |url=http://www.umweltbundesamt.de/uba-info-presse-e/hintergrund/pft-in-drinking-water.pdf |publisher=Drinking Water Commission (Trinkwasserkommission) of the German Ministry of Health at the Federal Environment Agency |pages=2–3 |access-date=12 June 2009 |url-status=dead |archive-url=https://web.archive.org/web/20101105041624/http://www.umweltbundesamt.de/uba-info-presse-e/hintergrund/pft-in-drinking-water.pdf |archive-date=5 November 2010 }} As of November 2023, the International Agency for Research on Cancer (IARC) has classified PFOA as carcinogenic to humans (Group 1) based on “sufficient” evidence for cancer in animals and “strong” mechanistic evidence in exposed humans.

An additional study has shown PFOA to be developmentally toxic, hepatotoxic, immunotoxic, and to have negative effects of thyroid hormone production.

= Human data =

PFOA is resistant to degradation by natural processes such as metabolism, hydrolysis, photolysis, or biodegradation and has been found to persist in the environment. PFOA is found in environmental and biological fluids as the anion perfluorooctanoate.{{cite journal|vauthors=Cheng J, Psillakis E, Hoffmann MR, Colussi AJ|year=2009|title=Acid Dissociation versus Molecular Association of Perfluoroalkyl Oxoacids: Environmental Implications|journal=J. Phys. Chem. A|volume=113|issue=29|pages=8152–6|doi=10.1021/jp9051352|pmid=19569653|url=https://authors.library.caltech.edu/15048/2/jp9051352_si_001.pdf|bibcode=2009JPCA..113.8152C|access-date=2019-08-03|archive-date=2024-07-12|archive-url=https://web.archive.org/web/20240712004804/https://authors.library.caltech.edu/15048/2/jp9051352_si_001.pdf|url-status=live}} PFOA can be absorbed from ingestion and can penetrate skin. The acid headgroup of PFOA enables binding to proteins with fatty acid or hormone substrates such as serum albumin, liver fatty acid-binding protein, and the nuclear receptors PPARα and possibly CAR.{{cite journal|vauthors=Cheng X, Klaassen CD|date=November 2008|title=Perfluorocarboxylic acids induce cytochrome P450 enzymes in mouse liver through activation of PPAR-alpha and CAR transcription factors|journal=Toxicol. Sci.|volume=106|issue=1|pages=29–36|doi=10.1093/toxsci/kfn147|pmc=2563145|pmid=18648086}}

In animals, PFOA is mainly present in the liver, blood, and kidneys. PFOA does not accumulate in fat tissue, unlike traditional organohalogen persistent organic pollutants. In humans, PFOA has an average elimination half-life of about three years.{{cite journal |vauthors=Bartell SM, Calafat AM, Lyu C, Kato K, Ryan PB, Steenland K |date=February 2010 |title=Rate of decline in serum PFOA concentrations after granular activated carbon filtration at two public water systems in Ohio and West Virginia|journal=Environ. Health Perspect. |volume=118 |issue=2 |pages=222–8 |doi=10.1289/ehp.0901252 |pmc=2831921 |pmid=20123620|bibcode=2010EnvHP.118..222B }}{{cite journal |vauthors=Steenland K, Fletcher T, Savitz DA |year=2010 |title=Epidemiologic Evidence on the Health Effects of Perfluorooctanoic Acid (PFOA)|journal=Environ. Health Perspect. |volume=118 |issue=8 |pages=1100–8 |doi=10.1289/ehp.0901827 |pmc=2920088 |pmid=20423814|bibcode=2010EnvHP.118.1100S }}{{cite journal |vauthors=Brede E, Wilhelm M, Göen T, Müller J, Rauchfuss K, Kraft M, Hölzer J |date=June 2010 |title=Two-year follow-up biomonitoring pilot study of residents' and controls' PFC plasma levels after PFOA reduction in public water system in Arnsberg, Germany |journal=Int J Hyg Environ Health |volume=213 |issue=3 |pages=217–23 |doi=10.1016/j.ijheh.2010.03.007 |pmid=20488749|bibcode=2010IJHEH.213..217B }} Because of this long half-life, PFOA has the potential to bioaccumulate.

The levels of PFOA exposure in humans vary widely. While an average American might have 3 or 4 parts per billion of PFOA present in their blood serum,{{cite journal |vauthors=Olsen GW, Mair DC, Church TR, etal |title =Decline in perfluorooctanesulfonate and other polyfluoroalkyl chemicals in American Red Cross adult blood donors, 2000–2006 |journal=Environ. Sci. Technol. |volume=42 |issue=13 |pages=4989–95 |date=July 2008 |pmid =18678038 |doi=10.1021/es800071x|bibcode =2008EnST...42.4989O |doi-access=free }} individuals occupationally exposed to PFOA have had blood serum levels over 100,000 parts per billion (100 parts per million or 0.01%) recorded.{{cite journal

|vauthors=Olsen GW, Burris JM, Burlew MM, Mandel JH | title =Plasma cholecystokinin and hepatic enzymes, cholesterol and lipoproteins in ammonium perfluorooctanoate production workers |journal =Drug Chem. Toxicol.|volume =23 |issue=4 |pages=603–20 |date=November 2000 |pmid =11071397 |doi=10.1081/DCT-100101973| s2cid =30289350 }} While no amount of PFOA in humans is legally recognized as harmful, DuPont was "not satisfied" with data showing their Chinese workers accumulated an average of about 2,250 parts per billion of PFOA in their blood from a starting average of around 50 parts per billion less than a year prior.

== Consumers ==

Single cross-sectional studies on consumers have been published noting multiple associations. Blood serum levels of PFOA were associated with an increased time to pregnancy—or "infertility"—in a 2009 study.{{cite journal |vauthors=Fei C, McLaughlin JK, Lipworth L, Olsen J |title=Maternal levels of perfluorinated chemicals and subfecundity |journal=Hum. Reprod. |volume=24 |issue=5 |pages=1200–1205 |date=January 2009 |pmid=19176540 |doi=10.1093/humrep/den490 |doi-access=free }} PFOA exposure was associated with decreased semen quality,{{cite journal |vauthors=Joensen UN, Bossi R, Leffers H, Jensen AA, Skakkebaek NE, Jørgensen N |title=Do perfluoroalkyl compounds impair human semen quality? | journal =Environ. Health Perspect. |volume=117 |issue=6 |pages=923–7 |date=June 2009 |pmid=19590684 |pmc=2702407 |doi=10.1289/ehp.0800517|bibcode=2009EnvHP.117..923J }} increased serum alanine aminotransferase levels,{{cite journal |vauthors=Lin CY, Lin LY, Chiang CK, Wang WJ, Su YN, Hung KY, Chen PC |title=Investigation of the Associations Between Low-Dose Serum Perfluorinated Chemicals and Liver Enzymes in US Adults |journal=Am. J. Gastroenterol. |volume=105 |issue=6|pages=1354–63 |date=December 2009 |pmid=20010922 |doi=10.1038/ajg.2009.707 |s2cid=9787611}} and increased occurrence of thyroid disease.{{cite journal |vauthors=Melzer D, Rice N, Depledge MH, Henley WE, Galloway TS |title=Association Between Serum Perfluoroctanoic Acid (PFOA) and Thyroid Disease in the NHANES Study |journal=Environ. Health Perspect. |volume=118 |issue=5 |pages=686–92 |year=2010 |pmid=20089479 |pmc=2866686 |doi=10.1289/ehp.0901584}} In a study of 2003–2004 US samples, a higher (9.8 milligram per deciliter) total cholesterol level was observed when the highest quartile was compared to the lowest.{{cite journal |vauthors= Nelson JW, Hatch EE, Webster TF |title= Exposure to Polyfluoroalkyl Chemicals and Cholesterol, Body Weight, and Insulin Resistance in the General U.S. Population |journal= Environ. Health Perspect. |volume= 118 |issue= 2 |pages= 197–202 |year= 2009 |pmid= 20123614 |pmc= 2831917 |doi= 10.1289/ehp.0901165 }} Along with other related compounds, PFOA exposure was associated with an increased risk of attention deficit hyperactivity disorder (ADHD) in a study of US children aged 12–15.{{cite journal |vauthors=Hoffman K, Webster TF, Weisskopf MG, Weinberg J, Vieira VM |title =Exposure to Polyfluoroalkyl Chemicals and Attention Deficit Hyperactivity Disorder in U.S. Children Aged 12–15 Years |journal=Environ. Health Perspect. |volume=118|issue=12 |pages=1762–7 |year=2010 |pmid= 20551004 |pmc=3002197 |doi=10.1289/ehp.1001898}} In a paper presented at the 2009 annual meeting of the International Society of Environmental Epidemiology,{{cite news |author=Ken Ward Jr. |url=http://blogs.wvgazette.com/watchdog/2009/11/03/pfoa-linked-to-adhd-and-hormone-disruption-in-kids/ |title=PFOA linked to ADHD and hormone disruption in kids |work=Blogs @ The Charleston Gazette |access-date=8 November 2009 |archive-date=7 November 2009 |archive-url=https://web.archive.org/web/20091107111756/http://blogs.wvgazette.com/watchdog/2009/11/03/pfoa-linked-to-adhd-and-hormone-disruption-in-kids/ |url-status=live }} PFOA appeared to act as an endocrine disruptor by a potential mechanism on breast maturation in young girls.{{cite journal |title=Perfluorooctanoic acid (PFOA) and Pubertal Maturation in Young Girls |vauthors=Pinney SM, Windham GC, Biro FM, Kushi LH, Yaghjyan L, Calafat A, Kato K, Succop P, Brown MK, Hernick A, Bornschein R |journal=Epidemiology |doi=10.1097/01.ede.0000362949.30847.cb |volume=20 |number=6 |pages=S80 |year=2009 |doi-access=free }} A C8 Science Panel status report noted an association between exposure in girls and a later onset of puberty.{{cite web |url=http://www.c8sciencepanel.org/pdfs/Status_Report_C8_and_puberty_27Sept2010.pdf |title=Patterns of age of puberty among children in the Mid-Ohio Valley in relation to Perfluorooctanoic Acid (PFOA) and Perfluorooctane Sulfonate (PFOS) |work=C8 Science Panel |access-date=21 October 2010 |archive-date=21 December 2010 |archive-url=https://web.archive.org/web/20101221232034/http://www.c8sciencepanel.org/pdfs/Status_Report_C8_and_puberty_27Sept2010.pdf |url-status=live }}

;Other impacts on exposure in utero

PFOA exposure on thyroid function has also been a topic of concern, and has found to negatively impact thyroid stimulating hormone even at low levels when exposed during fetal development.{{Cite journal |last1=Kato |first1=Shizue |last2=Itoh |first2=Sachiko |last3=Yuasa |first3=Motoyuki |last4=Baba |first4=Toshiaki |last5=Miyashita |first5=Chihiro |last6=Sasaki |first6=Seiko |last7=Nakajima |first7=Sonomi |last8=Uno |first8=Akiko |last9=Nakazawa |first9=Hiroyuki |date=September 2016 |title=Association of perfluorinated chemical exposure in utero with maternal and infant thyroid hormone levels in the Sapporo cohort of Hokkaido Study on the Environment and Children's Health |journal=Environmental Health and Preventive Medicine |volume=21 |issue=5 |pages=334–344 |doi=10.1007/s12199-016-0534-2 |issn=1347-4715 |pmc=5305986 |pmid=27137816|bibcode=2016EHPM...21..334K }} PFOA is also shown to have obesogenic effects, and an experimental study found a positive correlation to low-dose prenatal exposure of PFOA and prevalence of overweight and high waist circumference in females at age 20.{{Cite journal |last1=Halldorsson |first1=Thorhallur I. |last2=Rytte r|first2=Dorte |last3=Haug |first3=Line Småstuen |last4=Bech |first4=Bodil Hammer |last5=Danielsen |first5=Inge |last6=Becher |first6=Georg |last7=Henriksen |first7=Tine Brink |last8=Olsen |first8=Sjurdur F. |date=May 2012 |title=Prenatal Exposure to Perfluorooctanoate and Risk of Overweight at 20 Years of Age: A Prospective Cohort Study|journal=Environmental Health Perspectives |volume=120 |issue=5 |pages=668–673 |doi=10.1289/ehp.1104034|issn=0091-6765 |pmc=3346773 |pmid=22306490|bibcode=2012EnvHP.120..668H }} A correlation between in utero PFOA exposure and mental performance has yet to be established, as many studies have resulted in insignificant results. For example, a study conducted near Parkersburg, West Virginia did not find a significant association between in utero PFOA exposure and performance of math skills or reading performance in children ages 6 to 12 living in the PFOA-contaminated water district.{{Cite journal |last1=Stein |first1=Cheryl R. |last2=Savitz |first2=David A. |last3=Bellinger |first3=David C. |date=July 2013|title=Perfluorooctanoate and neuropsychological outcomes in children |journal=Epidemiology |volume=24 |issue=4 |pages=590–599 |doi=10.1097/EDE.0b013e3182944432 |issn=1531-5487 |pmc=4020323 |pmid=23680941}} Based on a cohort study conducted in the Mid-Ohio Valley, no clear association was found between prenatal exposure to PFOA and birth defects, although a possible association with brain defects was observed and requires further research and assessment.{{Cite journal |last1=Stein |first1=Cheryl R. |last2=Savitz |first2=David A .|last3=Elston |first3=Beth |last4=Thorpe |first4=Phoebe G. |last5=Gilboa |first5=Suzanne M. |date=August 2014 |title=Perfluorooctanoate exposure and major birth defects |journal=Reproductive Toxicology |volume=47 |pages=15–20 |doi=10.1016/j.reprotox.2014.04.006 |pmid=24803403 |pmc=4117925|bibcode=2014RepTx..47...15S }}

Extrapolated epidemiological data suggests a slight association between PFOA exposure and low birth weight.{{Cite journal |last1=Negri |first1=Eva |last2=Metruccio |first2=Francesca |last3=Guercio |first3=Valentina |last4=Tosti |first4=Luca |last5=Benfenati |first5=Emilio |last6=Bonzi |first6=Rossella |last7=La Vecchia |first7=Carlo |last8=Moretto |first8=Angelo |date=2017-02-15 |title=Exposure to PFOA and PFOS and fetal growth: a critical merging of toxicological and epidemiological data |journal=Critical Reviews in Toxicology|volume=47|issue=6|pages=489–515|doi=10.1080/10408444.2016.1271972|pmid=28617200|s2cid=1447174|issn=1040-8444}} This was consistent based on blood levels of PFOA metabolites regardless of the geographic residence of subjects. Generally, the findings among human fetuses exposed to the chemical were considerably less drastic than what was seen in mice studies. Because of this, studies linking exposure to low birth weight can be considered inconclusive. PFOA exposure in the Danish general population was not associated with an increased risk of prostate, bladder, pancreatic, or liver cancer.{{cite journal |vauthors=Eriksen KT, Sørensen M, McLaughlin JK, Lipworth L, Tjønneland A, Overvad K, Raaschou-Nielsen O |date=April 2009 |title=Perfluorooctanoate and perfluorooctanesulfonate plasma levels and risk of cancer in the general Danish population |journal=J. Natl. Cancer Inst. |volume=101 |issue=8 |pages=605–9 |doi=10.1093/jnci/djp041|pmid=19351918|doi-access=free}} Maternal PFOA levels were not associated with an offspring's increased risk of hospitalization due to infectious diseases,{{cite journal |vauthors=Fei C, McLaughlin JK, Lipworth L, Olsen J |date=November 2010 |title=Prenatal exposure to PFOA and PFOS and risk of hospitalization for infectious diseases in early childhood |journal=Environ. Res.|volume=110|issue=8 |pages=773–7 |doi=10.1016/j.envres.2010.08.004 |pmid=20800832 |bibcode=2010ER....110..773F}} behavioral and motor coordination problems,{{cite journal |vauthors=Fei C, Olsen J |year=2010 |title=Prenatal Exposure to Perfluorinated Chemicals and Behavioral or Coordination Problems at Age 7|journal=Environ. Health Perspect. |volume=119 |issue=4 |pages=573–578 |doi=10.1289/ehp.1002026 |pmc=3080943 |pmid=21062688}} or delays in reaching developmental milestones.{{cite journal |vauthors=Fei C, McLaughlin JK, Lipworth L, Olsen J |date=October 2008 |title=Prenatal exposure to perfluorooctanoate (PFOA) and perfluorooctanesulfonate (PFOS) and maternally reported developmental milestones in infancy|journal=Environ. Health Perspect. |volume=11 6|issue=10 |pages=1391–5 |doi=10.1289/ehp.11277 |pmc=2569100|pmid=18941583|bibcode=2008EnvHP.116.1391F }}

== Employees and DuPont exposed community ==

In 2010, the three members of the C8 Science Panel{{Cite web|url=http://www.c8sciencepanel.org/|title=C8 Science Panel Website|website=www.c8sciencepanel.org|access-date=2008-10-19|archive-date=2019-06-18|archive-url=https://web.archive.org/web/20190618160631/http://www.c8sciencepanel.org/|url-status=live}} published a review of the epidemiological evidence on PFOA exposure in Environmental Health Perspectives. Insufficient evidence exists to conclude PFOA causes adverse health effects in humans, but consistent evidence exists on associations with higher cholesterol and uric acid. Whether or not these potential effects result in an increase in cardiovascular disease is unknown.{{cite journal |vauthors=Steenland K, Tinker S, Frisbee S, Ducatman A, Vaccarino V |title=Association of perfluorooctanoic acid and perfluorooctane sulfonate with serum lipids among adults living near a chemical plant |journal=Am. J. Epidemiol. |volume=170 |issue=10 |pages=1268–78 |date=November 2009

|pmid=19846564 |doi=10.1093/aje/kwp279|doi-access=free }} Further data on the 69,030 member cohort{{cite journal |vauthors=Frisbee SJ, Brooks AP, Maher A, Flensborg P, Arnold S, Fletcher T, Steenland K, Shankar A, Knox SS, Pollard C, Halverson JA, Vieira VM, Jin C, Leyden KM, Ducatman AM |title=The C8 health project: design, methods, and participants |journal=Environ. Health Perspect. |volume=117 |issue=12 |pages=1873–82 |date=December 2009 |pmid=20049206 |pmc=2799461 |doi=10.1289/ehp.0800379|bibcode=2009EnvHP.117.1873F }} that is being studied by the panel is scheduled for release through 2012.{{cite web |url=http://www.c8sciencepanel.org/timeline.html |title=Timeline |publisher=C8 Science Panel |access-date=9 June 2011 |archive-url=https://web.archive.org/web/20110604043253/http://www.c8sciencepanel.org/timeline.html |archive-date=2011-06-04 |url-status=dead}}{{Obsolete source|reason= this material needs updating, the results should be out|date=March 2021}} A 2011 epidemiological study demonstrated "probable link" between PFOA and kidney cancer, testicular cancer, thyroid disease, high cholesterol, pre-eclampsia and ulcerative colitis.{{cite web |url=http://www.c8sciencepanel.org/prob_link.html |title=C8 Science Panel Website |publisher=C8sciencepanel.org |access-date=2016-01-09 |archive-date=2013-04-14 |archive-url=https://archive.today/20130414091736/http://www.c8sciencepanel.org/prob_link.html |url-status=live }}

Facial birth defects, an effect observed in rat offspring, occurred with the children of two out of seven female DuPont employees from the Washington Works facility from 1979 to 1981.{{cite news |first=Amy |last=Cortese |title=DuPont, Now in the Frying Pan |work=The New York Times |page=3 |date=8 August 2004 |access-date=30 December 2008 |url=https://www.nytimes.com/2004/08/08/business/dupont-now-in-the-frying-pan.html |archive-date=12 July 2024 |archive-url=https://web.archive.org/web/20240712004807/https://www.nytimes.com/2004/08/08/business/dupont-now-in-the-frying-pan.html |url-status=live }} Bucky Bailey is one of the affected individuals; DuPont, however, does not accept any liability from the toxicity of PFOA.{{cite news |first=Chris |last=Summers |title=Teflon's sticky situation |work=BBC News |date=7 October 2004 |access-date=30 December 2008 |url=http://news.bbc.co.uk/2/hi/uk_news/magazine/3697324.stm |archive-date=30 November 2008 |archive-url=https://web.archive.org/web/20081130235249/http://news.bbc.co.uk/2/hi/uk_news/magazine/3697324.stm |url-status=live }} While 3M sent DuPont results from a study that showed birth defects to rats administered PFOA and DuPont moved the women out of the Teflon production unit, subsequent animal testing led DuPont to conclude there was no reproductive risk to women, and they were returned to the production unit.{{cite report |title=Biomonitoring: EPA Needs to Coordinate Its Research Strategy and Clarify Its Authority to Obtain Biomonitoring Data |id=GAO-09-353 |url=http://www.gao.gov/new.items/d09353.pdf |publisher=US Government Accountability Office |pages=19–20 |date=April 2009 |access-date=19 June 2009 |archive-date=21 May 2011 |archive-url=https://web.archive.org/web/20110521144202/http://www.gao.gov/new.items/d09353.pdf |url-status=live }} However, data released in March 2009 on the community around DuPont's Washington Works plant showed "a modest, imprecise indication of an elevation in risk ... above the 90th percentile ... based on 12 cases in the uppermost category", which was deemed "suggestive of a possible relationship" between PFOA exposure and birth defects.{{cite web |url=http://www.c8sciencepanel.org/pdfs/Status_Report_C8_and_Pregnancy_Outcomes_March2009.pdf |title=Relationship of perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS) with pregnancy outcome among women with elevated community exposure to PFOA |publisher=C8 Science Panel |access-date=27 June 2009 |archive-date=21 December 2010 |archive-url=https://web.archive.org/web/20101221233338/http://www.c8sciencepanel.org/pdfs/Status_Report_C8_and_Pregnancy_Outcomes_March2009.pdf |url-status=live }}{{cite web |url=http://www.c8sciencepanel.org/study_results.html |title=C8 Study Results – Status Reports |publisher= C8 Science Panel |access-date=27 June 2009 |archive-url=https://web.archive.org/web/20081121040735/http://www.c8sciencepanel.org/study_results.html |archive-date=2008-11-21 |url-status=dead}}

Legal actions

= International action: Stockholm Convention =

PFOA was proposed for listing under the Stockholm Convention on Persistent Organic Pollutants in 2015, and on May 10, 2019, PFOA, its salts, and PFOA-related compounds were added to Annex A of the Stockholm Convention by the Conference of the Parties.{{Cite web|title=Stockholm Convention COP.9 – Meeting documents|url=http://chm.pops.int/TheConvention/ConferenceoftheParties/Meetings/COP9/tabid/7521/Default.aspx|access-date=2021-01-14|website=chm.pops.int|archive-date=2021-01-17|archive-url=https://web.archive.org/web/20210117163636/http://chm.pops.int/TheConvention/ConferenceoftheParties/Meetings/COP9/tabid/7521/Default.aspx|url-status=live}} Several hundred salts and precursors of PFOA fall within the scope of the restriction.{{Cite web |date=2022 |others=UNEP/POPS/POPRC.17/INF/14/Rev.1 |title=Updated indicative list of substances covered by the listing of perfluorooctanoic acid (PFOA), its salts and PFOA-related compounds |url=http://chm.pops.int/TheConvention/POPsReviewCommittee/Meetings/POPRC17/Overview/tabid/8900/ctl/Download/mid/24942/Default.aspx?id=21&ObjID=30053 |website=pops.int |access-date=2022-10-22 |archive-date=2022-10-22 |archive-url=https://web.archive.org/web/20221022184634/http://chm.pops.int/TheConvention/POPsReviewCommittee/Meetings/POPRC17/Overview/tabid/8900/ctl/Download/mid/24942/Default.aspx?id=21&ObjID=30053 |url-status=live }}{{cite web|title=PFAS and Fluorinated Compounds in PubChem Tree|periodical=PubChem Classification Browser|publisher=NCBI|url=https://pubchem.ncbi.nlm.nih.gov/classification/#hid=120|url-status=live|format=|access-date=2022-10-21|archive-url=https://web.archive.org/web/20221021075138/https://pubchem.ncbi.nlm.nih.gov/classification/#hid=120|archive-date=2022-10-21|date=|year=|language=|pages=|quote=}} → Regulatory PFAS collections → PFOA and related substances A few specific exemptions remained. Among them is a time-bound exemption for PFOA in fire-fighting foam.

= U.S. federal government actions =

In 2002, a panel of toxicologists, including several from EPA, proposed a level of 150 ppb for drinking water in the PFOA contaminated area around DuPont's Washington Works plant. This initially proposed level was much higher than any known environmental concentration and was over 2,000 times the level EPA eventually settled on for the drinking water health advisory.

In July 2004, EPA filed a suit against DuPont alleging "widespread contamination" of PFOA near the Parkersburg, West Virginia plant "at levels exceeding the company's community exposure guidelines;" the suit also alleged that "DuPont had—over a 20 year period—repeatedly failed to submit information on adverse effects (in particular, information on liver enzyme alterations and birth defects in offspring of female Parkersburg workers)."

In October 2005, a USFDA study was published revealing PFOA and PFOA precursor chemicals in food contact and PTFE products.

On January 25, 2006, EPA announced a voluntary program with several chemical companies to reduce PFOA and PFOA precursor emissions by the year 2015.{{cite web |url=http://www.epa.gov/opptintr/pfoa/pubs/pfoastewardship.htm |title=2010/15 PFOA Stewardship Program; PFOA and Fluorinated Telomers |publisher=EPA |access-date=19 September 2008 |url-status=dead |archive-url=https://web.archive.org/web/20081027061359/http://www.epa.gov/opptintr/pfoa/pubs/pfoastewardship.htm |archive-date=27 October 2008}}

On February 15, 2005, EPA's Science Advisory Board (SAB) voted to recommended that PFOA should be considered a "likely human carcinogen".{{cite journal |author =Renner R |title=Scientists hail PFOA reduction plan |journal=Environ. Sci. Technol. |volume=40 |issue=7 |pages=2075–6 |year=2006 |doi=10.1021/es062654z |pmid =16646434 |last2=Christen |first2=Kris |doi-access=free }}

On May 26, 2006, EPA's SAB addressed a letter to Administrator Stephen L. Johnson. Three-quarters of advisers thought the stronger "likely to be carcinogenic" descriptor was warranted, in opposition to EPA's own PFOA hazard descriptor of "suggestive evidence of carcinogenicity, but not sufficient to assess human carcinogenic potential".{{cite conference |title=SAB Review of EPA's Draft Risk Assessment of Potential Human Health Effects Associated with PFOA and Its Salts |publisher=EPA Science Advisory Board |date=2006-05-30 |url=http://yosemite.epa.gov/sab/sabproduct.nsf/A3C83648E77252828525717F004B9099/$File/sab_06_006.pdf |page=2 |access-date=2008-09-21 |archive-date=2008-10-26 |archive-url=https://web.archive.org/web/20081026190006/http://yosemite.epa.gov/sab/SABPRODUCT.NSF/A3C83648E77252828525717F004B9099/$File/sab_06_006.pdf |url-status=live }}

On November 21, 2006, EPA ordered DuPont to offer alternative drinking water or treatment for public or private water users living near DuPont's Washington Works plant in West Virginia (and in Ohio), if the level of PFOA detected in drinking water is equal to or greater than 0.5 parts per billion. This measure sharply lowered the previous action level of 150 parts per billion that was established in March 2002.{{cite web |publisher=EPA |title=Fact Sheet: EPA, DuPont Agree on Measures to Protect Drinking Water Near the DuPont Washington Works |author=Mid-Atlantic Enforcement |url=http://www.epa.gov/region03/enforcement/dupont_factsheet.html |date=10 May 2007 |access-date=11 May 2008 |archive-url=https://web.archive.org/web/20080118114054/http://www.epa.gov/region03/enforcement/dupont_factsheet.html |archive-date=18 January 2008 |url-status=dead}}

According to a May 23, 2007, Environmental Science & Technology Online article, U.S. Food and Drug Administration research regarding food contact papers as a potential source of PFOA to humans is ongoing.

In November 2007, the Centers for Disease Control and Prevention (CDC) published data on PFOA concentrations comparing 1999–2000 vs. 2003–2004 NHANES samples.

In October 2021 the EPA proposed to designate PFOA and PFOS as hazardous substances in its PFAS Strategic Roadmap.RIN [https://www.reginfo.gov/public/do/eAgendaViewRule?RIN=2050-AH09 2050-AH09] {{Webarchive|url=https://web.archive.org/web/20220926034957/https://www.reginfo.gov/public/do/eAgendaViewRule?RIN=2050-AH09 |date=2022-09-26 }}EPA. "Addressing PFOA and PFOS in the Environment: Potential Future Regulation Pursuant to the Comprehensive Environmental Response, Compensation, and Liability Act and the Resource Conservation and Recovery Act." Rulemaking Docket [https://www.regulations.gov/docket/EPA-HQ-OLEM-2019-0341 EPA-HQ-OLEM-2019-0341] {{Webarchive|url=https://web.archive.org/web/20220926034956/https://www.regulations.gov/docket/EPA-HQ-OLEM-2019-0341 |date=2022-09-26 }} In September 2022 the EPA proposed to designate as hazardous substances under the Superfund Comprehensive Environmental Response, Compensation, and Liability Act of 1980 (CERCLA).

In 2024 EPA published drinking water regulations for PFOA and five other PFAS.

= U.S. state government actions =

{{Duplication|dupe=Perfluorooctanoic acid#Regulatory status|section=y|othersections=y}}

== New Jersey ==

In 2007 the New Jersey Department of Environmental Protection (NJDEP) announced that it found PFOA at "elevated levels in the system's drinking water near DuPont's massive Chambers Works chemical plant".{{cite journal |last1=Renner |first1=Rebecca |last2=Cooney |first2=Catherine M. |last3=Pelley |first3=Janet |last4=Chatterjee |first4=Rhitu |last5=Lubick |first5=Naomi |last6=Engelhaupt |first6=Erika |title=New Jersey dives into PFOA water guidance |journal=Environ. Sci. Technol. |volume=41 |issue=10 |pages=3395–6 |date=May 2007|pmid =17547148 |doi=10.1021/es072532m|doi-access=free }}

In 2018 the state published a drinking water standard for PFNA. Public water systems in New Jersey are required to meet a maximum contaminant level (MCL) standard of 13 ppt.{{cite web |title=Maximum Contaminant Levels (MCLs) for Perfluorononanoic Acid and 1,2,3-Trichloropropane; Private Well Testing for Arsenic, Gross Alpha Particle Activity, and Certain Synthetic Organic Compounds |url=https://advance.lexis.com/api/document/collection/administrative-codes/id/5T61-TR60-01XC-F17T-00008-00?cite=50%20N.J.R.%201939(a)&context=1000516 |date=2018-09-04 |publisher=NJDEP |id=50 N.J.R. 1939(a) |access-date=2021-02-14 |archive-date=2021-10-06 |archive-url=https://web.archive.org/web/20211006204818/https://signin.lexisnexis.com/lnaccess/app/signin?back=https%3A%2F%2Fadvance.lexis.com%3A443%2Flaapi%2Fdocument%3Fcite%3D50%2BN.J.R.%2B1939%28a%29%26context%3D1000516%26collection%3Dadministrative-codes%26id%3D5T61-TR60-01XC-F17T-00008-00&aci=la |url-status=live }}

In 2019 New Jersey filed lawsuits against the owners of two plants that had manufactured PFASs (the Chambers Works and the Parlin plant in Sayreville), and two plants that were cited for water pollution from other chemicals. The companies cited are DuPont, Chemours and 3M.{{cite web |title=AG Grewal, DEP Commissioner Announce 4 New Environmental Lawsuits Focused on Contamination Allegedly Linked to DuPont, Chemours, 3M |url=https://www.nj.gov/oag/newsreleases19/pr20190327a.html |date=2019-03-27 |publisher=New Jersey Office of the Attorney General |location=Totowa, NJ |id=Press release |access-date=2021-02-14 |archive-date=2021-01-13 |archive-url=https://web.archive.org/web/20210113223236/https://www.nj.gov/oag/newsreleases19/pr20190327a.html |url-status=live }}

In 2020 the NJDEP set a PFOA standard at 14 ppt and a PFOS standard at 13 ppt.

== New York ==

In 2018 the New York State Department of Health adopted drinking water standards of 10 ppt for PFOA and 10 ppt for PFOS, effective in 2019 after a public comment period.

== Michigan ==

In November 2017, the Michigan PFAS Action Response Team (MPART) was created to address growing pollution concerns after multiple sites contaminated by PFAS were identified. MPART is a multi-agency team tasked with investigating PFAS contamination sites and sources in the state, protecting drinking water, enhancing interagency communication and keeping the public informed.{{Cite web |last=Ellison |first=Garret |date=2017-11-13 |title=Michigan creates multi-agency PFAS pollution response team |url=https://www.mlive.com/news/2017/11/michigan_pfas_response_team.html |archive-url=https://web.archive.org/web/20220401003525/https://www.mlive.com/news/2017/11/michigan_pfas_response_team.html |archive-date=2022-04-01 |access-date=2022-04-23 |website=MLive}}

In January 2018, Michigan established a legally enforceable groundwater cleanup level of 70 ppt for both PFOA and PFOS. Two science advisory committees were also created and joined MPART to "coordinate and review medical and environmental health, PFAS science and develop evidence-based recommendations".{{Cite web |date=2018-01-10 |title=Michigan abruptly sets PFAS cleanup rules |url=https://www.mlive.com/news/2018/01/michigan_pfos_pfoa_part_201_cr.html |access-date=2022-03-27 |website=mlive |language=en |archive-date=2021-12-22 |archive-url=https://web.archive.org/web/20211222125321/https://www.mlive.com/news/2018/01/michigan_pfos_pfoa_part_201_cr.html |url-status=live }}

In August 2020, the Michigan Department of Environment, Great Lakes, and Energy adopted stricter drinking water standards in the form of MCLs, lowering acceptable levels from the 2018 enforceable groundwater cleanup levels of 70 ppt to 8 ppt for PFOA and 16 ppt for PFOS and adding MCLs for 5 previously unregulated PFAS compounds PFNA, PFHxA, PFHxS, PFBS, and HFPO-DA.{{Cite web |date=3 August 2020 |title=New state drinking water standards pave way for expansion of Michigan's PFAS clean-up efforts |url=https://www.michigan.gov/egle/0,9429,7-135--535602--,00.html |url-status=live |archive-url=https://web.archive.org/web/20220103083526/https://www.michigan.gov/egle/0,9429,7-135--535602--,00.html |archive-date=3 January 2022 |access-date=6 April 2022 |website=Michigan.gov}}{{Cite web |last=Matheny |first=Keith |date=3 August 2020 |title=Michigan's drinking water standards for these chemicals now among toughest in nation |url=https://www.freep.com/story/news/local/michigan/2020/08/03/tougher-pfas-standards-drinking-water-michigan/5574268002/ |url-status=live |archive-url=https://web.archive.org/web/20220131152306/https://eu.freep.com/story/news/local/michigan/2020/08/03/tougher-pfas-standards-drinking-water-michigan/5574268002/ |archive-date=31 January 2022 |access-date=31 March 2022 |website=Detroit Free Press}}

== Minnesota ==

In 2007, the Minnesota Department of Health lowered its Health Based Value for PFOA in drinking water from 1.0 ppb to 0.5 ppb,{{cite web |author= |date=2007-03-01 |title=Health officials issue new health guidelines for PFOA, PFOS |url=http://www.health.state.mn.us/news/pressrel/pfc030107.html |url-status=dead |archive-url=https://web.archive.org/web/20070814205017/http://health.state.mn.us/news/pressrel/pfc030107.html |archive-date=2007-08-14 |publisher=Minnesota Department of Health |id=News Release}} where "the sources are landfilled industrial wastes from a 3M manufacturing plant".

= European action =

PFOA contaminated waste was incorporated into soil improver and spread on agricultural land in Germany, leading to PFOA drinking water contamination of up to 0.519 parts per billion.{{cite journal |title =Perfluorinated surfactants contaminate German waters—Mislabeled waste in fertilizer leads to a water scandal |journal =Environ. Sci. Technol. |date =2006-12-01

| volume =40 |issue=23 |pages=7108–14 |doi =10.1021/es062811u |author1=Anke Schaefer |author2=Barbara Booth |author3=Naomi Lubick |author4=Kellyn S. Betts |doi-access=free }}{{cite journal |vauthors=Skutlarek D, Exner M, Färber H |title=Perfluorinated surfactants in surface and drinking waters |journal=Environ. Sci. Pollut. Res. Int. |volume=13 |issue=5 |pages=299–307 |date=September 2006 |pmid=17067024 |url=http://www.scientificjournals.com/sj/espr/Abstract/ArtikelId/8685 |doi=10.1065/espr2006.07.326 |bibcode=2006ESPR...13..299E |s2cid=95762541 |access-date=2008-10-04 |archive-url=https://web.archive.org/web/20080905132725/http://www.scientificjournals.com/sj/espr/Abstract/ArtikelId/8685 |archive-date=2008-09-05 |url-status=dead |url-access=subscription }} The German Federal Environmental Agency issued guidelines for the sum of PFOA and PFOS concentrations in drinking water: 0.1 parts per billion for precaution and 0.3 parts per billion for a threshold.{{cite journal |vauthors=Roos PH, Angerer J, Dieter H, Wilhelm M, Wölfle D, Hengstler JG |date=January 2008 |title=Perfluorinated compounds (PFC) hit the headlines: meeting report on a satellite symposium of the annual meeting of the German Society of Toxicology |journal=Arch. Toxicol. |volume=82 |issue=1 |pages=57–9 |bibcode=2008ArTox..82...57R |doi=10.1007/s00204-007-0225-2 |pmid=17687546 |s2cid=8653328}} Residents were found to have a 6–8 factor increase of PFOA serum levels over unexposed Germans, with average PFOA concentrations in the 22–27 parts per billion range. An expert panel concluded that "concentrations were considered too low to cause overt adverse health effects in the exposed population".

In the Netherlands, after questions by members of Parliament, the minister of Environment ordered a study into the potential exposure to PFOA of people living in the vicinity of the DuPont factory in Dordrecht. The report was published in March 2016 and concluded that "prior to 2002 residents were exposed to levels of PFOA at which health effects could not be ruled out".{{Cite web|url=http://rivm.nl/Documenten_en_publicaties/Wetenschappelijk/Rapporten/2016/maart/Risicoschatting_emissie_PFOA_voor_omwonenden_Locatie_DuPont_Chemours_Dordrecht_Nederland|title=Risicoschatting emissie PFOA voor omwonenden : Locatie: DuPont/Chemours, Dordrecht, Nederland|website=rivm.nl|access-date=2016-08-31|archive-date=2016-09-15|archive-url=https://web.archive.org/web/20160915200720/http://rivm.nl/Documenten_en_publicaties/Wetenschappelijk/Rapporten/2016/maart/Risicoschatting_emissie_PFOA_voor_omwonenden_Locatie_DuPont_Chemours_Dordrecht_Nederland|url-status=live}} As a result of this, the government commissioned several further studies, including blood tests and measurements in drinking water.

PFOA was identified as a PBT substance in the EU in 2013. It was then included in the candidate list of substances of very high concern. In 2017, PFOA, its salts and PFOA-related substances were added to annex XVII (restriction) of the REACH Regulation.[https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=OJ:L:2017:150:FULL Official Journal of the European Union, L 150] {{Webarchive|url=https://web.archive.org/web/20180823042115/https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=OJ:L:2017:150:FULL |date=2018-08-23 }}, 14 June 2017.

The EU adopted the listing of PFOA in Annex A of the Stockholm Convention with Commission Delegated Regulation (EU) 2020/784 of 8 April 2020 and introduced a limit value of 0,025 mg/kg for PFOA including its salts, and at 1 mg/kg for the individual PFOA-related compounds or a combination of those compounds.{{Citation|title=Commission Delegated Regulation (EU) 2020/784 of 8 April 2020 amending Annex I to Regulation (EU) 2019/1021 of the European Parliament and of the Council as regards the listing of perfluorooctanoic acid (PFOA), its salts and PFOA-related compounds (Text with EEA relevance) |date=2020-06-15 |url=http://data.europa.eu/eli/reg_del/2020/784/oj/eng|issue=32020R0784 |access-date=2021-01-14}} They also included some specific exemptions. Among them is a time-bound exemption for PFOA in fire-fighting foam.

= Australian action =

On August 10, 2016, Australian litigation funder IMF Bentham announced an agreement to fund a class action led by the law firm Gadens against the Australian Department of Defence for economic losses to homeowners, fishers, and farmers resulting from the use of aqueous film forming foam (containing PFOA) at RAAF Base Williamtown.{{cite web |url=https://www.linkedin.com/pulse/imf-announces-williamtown-pfos-pfoa-contamination-class-oliver-gayner |title=Press Release: Williamtown Contamination Class Action |last1=Gayner |first1=Oliver |date=2016-08-10 |website=LinkedIn |publisher=IMF Bentham |access-date=2016-08-22 |archive-date=2021-11-04 |archive-url=https://web.archive.org/web/20211104133011/https://www.linkedin.com/pulse/imf-announces-williamtown-pfos-pfoa-contamination-class-oliver-gayner |url-status=live }}

See also

References

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