Perfluorononanoic acid explained

Perfluorononanoic acid, or PFNA, is a synthetic perfluorinated carboxylic acid and fluorosurfactant that is also an environmental contaminant found in people and wildlife along with PFOS and PFOA.

Chemistry and properties

In acidic form it is a highly reactive strong acid. In its conjugate base form as a salt it is stable and commonly ion paired with ammonium. In the commercial product Surflon S-111 (CAS 72968-3-88) it is the primary compound present by weight. PFNA is used as surfactant for the production of the fluoropolymer polyvinylidene fluoride.[1] [2] It is produced mainly in Japan by the oxidation of a linear fluorotelomer olefin mixture containing F(CF2)8CH=CH2. It can also be synthesized by the carboxylation of F(CF2)8I. PFNA can form from the biodegradation of 8:2 fluorotelomer alcohol.[3] Additionally, it is considered a probable degradation product of many other compounds.[4]

PFNA is the largest perfluorinated carboxylic acid surfactant. Fluorocarbon derivatives with terminal carboxylates are only surfactants when they possess five to nine carbons.[5] Fluorosurfactants reduce the surface tension of water down to half of what hydrocarbon surfactants can by concentrating at the liquid-air interface due to the lipophobicity of fluorocarbons.[5] [6] PFNA is very stable and is not known to degrade in the environment by oxidative processes because of the strength of the carbon–fluorine bond and the electronegativity of fluorine.

Environmental and health concerns

Like the eight-carbon PFOA, the nine-carbon PFNA is a developmental toxicant and an immune system toxicant.[7] However, longer chain perfluorinated carboxylic acids (PFCAs) are considered more bioaccumulative and toxic.[8] PFNA is an agonist of the nuclear receptors PPARα and PPARγ.[7] In the years between 1999–2000 and 2003–2004, the geometric mean of PFNA increased from 0.5 parts per billion to 1.0 parts per billion in the US population's blood serum.[9] and has also been found in human follicular fluid [10] In a cross-sectional study of 2003–2004 US samples, a higher (13.9 milligram per deciliter) total cholesterol level was observed in when the highest quartile was compared to the lowest.[11] Non-HDL cholesterol (or "bad cholesterol") levels were also higher in samples with more PFNA.

In bottlenose dolphins from Delaware Bay, PFNA was the perfluorinated carboxylic acid measured in the highest concentration in blood plasma; it was found in concentrations well over 100 parts per billion.[12] PFNA has been detected in polar bears in concentrations over 400 parts per billion.[13] PFNA was the perfluorinated chemical measured in the highest concentration in Russian Baikal seals.[14] However, PFOS is the perfluorinated compound that dominates in most wildlife biomonitoring samples.[15]

Drinking water regulations

In the United States there are no federal drinking water standards for any of the perfluorinated alkylated substances as of late 2020.[16] The U.S. Environmental Protection Agency (EPA) published a non-enforceable health advisory for PFOA in 2016. The agency's health advisory level for the combined concentrations of PFOA and PFOS is 70 parts per trillion (ppt).[17] [18]

In June 2020 the State of New Jersey published a drinking water standard for PFOA, the first state to do so. Public water systems in New Jersey are required to meet a maximum contaminant level (MCL) standard of 14 ppt. The state also set a PFOS standard at 13 ppt.[19] The state had set a standard for PFNA in September 2018, with an MCL of 13 ppt.[20] [21]

In August 2020 the State of Michigan adopted drinking water standards for 5 previously unregulated PFAS compounds and lowered acceptable levels for 2 previously regulated compounds PFOS and PFOA to 16 ppt and 8 ppt respectively. PFNA has a MCL of 6 ppt.[22] [23]

Food Regulation

In 2020, the European Food Safety Authority added PFNA in its revised safety threshold for PFAS that accumulate in the body. They set the threshold for a group of four PFAS of a tolerable weekly intake of 4.4 nanograms per kilogram of body weight per week.[24]

Product Restrictions

In 2020, a California bill was passed banning PFNA as an intentionally added ingredient from cosmetics.[25]

See also

External links

Notes and References

  1. Prevedouros K, Cousins IT, Buck RC, Korzeniowski SH . Sources, fate and transport of perfluorocarboxylates. Environ Sci Technol. 40 . 1 . 32–44 . January 2006. 10.1021/es0512475 . 16433330. 2006EnST...40...32P. Supporting Information (PDF)
  2. PERFORCE - PERFLUORINATED ORGANIC COMPOUNDS IN THE EUROPEAN ENVIRONMENT. Institute for Biodiversity and Ecosystem Dynamics, Universiteit van Amsterdam. 2006-09-15 . 18. 2009-02-15.
  3. Henderson WM, Smith MA . Perfluorooctanoic acid and perfluorononanoic acid in fetal and neonatal mice following in utero exposure to 8–2 fluorotelomer alcohol. Toxicol. Sci. . 95 . 2 . 452–61 . February 2007. 17093205 . 10.1093/toxsci/kfl162 . free .
  4. Lists of PFOS, PFAS, PFOA, PFCA, related compounds and chemicals that may degrade to PFCA . Environment Directorate-Joint Meeting of the Chemicals Committee and the Working Party on Chemicals, Pesticides, and Biotechnology. Organisation for Economic Co-operation and Development. 2007-08-21 . 2008-09-19.
  5. Jean-Louis. Salager. FIRP Booklet # 300-A: Surfactants-Types and Uses. 44. Universidad de los Andes Laboratory of Formulation, Interfaces Rheology, and Processes. 2002. 2008-09-07. 2020-07-31. https://web.archive.org/web/20200731194249/http://nanoparticles.org/pdf/Salager-E300A.pdf. dead.
  6. Web site: Fluorosurfactant - Structure / Function . Mason Chemical Company . 11 January 2009 . dead . https://web.archive.org/web/20080705074650/http://www.masonsurfactants.com/Products/Fluorosurfactant.htm . 5 July 2008.
  7. Fang X, Zhang L, Feng Y, Zhao Y, Dai J . Immunotoxic effects of perfluorononanoic acid on BALB/c mice. Toxicol. Sci. . 105 . 2 . 312–21 . October 2008. 18583369 . 10.1093/toxsci/kfn127 . free .
  8. Del Gobbo L, Tittlemier S, Diamond M, etal . Cooking decreases observed perfluorinated compound concentrations in fish . Journal of Agricultural and Food Chemistry . 56 . 16 . 7551–9 . August 2008 . 18620413 . 10.1021/jf800827r.
  9. Calafat AM, Wong LY, Kuklenyik Z, Reidy JA, Needham LL . 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 . Environ. Health Perspect. . 115 . 11 . 1596–602 . November 2007 . 18007991 . 2072821 . 10.1289/ehp.10598 . 2009-01-11 . https://web.archive.org/web/20090120064652/http://www.ehponline.org/members/2007/10598/10598.html . 2009-01-20 . dead .
  10. Bach . Cathrine Carlsen . Bech . Bodil Hammer . Nohr . Ellen Aagaard . Olsen . Jørn . Matthiesen . Niels Bjerregård . Bossi . Rossana . Uldbjerg . Niels . Bonefeld-Jørgensen . Eva Cecilie . Henriksen . Tine Brink . 2015-10-01 . Serum perfluoroalkyl acids and time to pregnancy in nulliparous women . Environmental Research . 142 . 535–541 . 10.1016/j.envres.2015.08.007. 26282225 . 2015ER....142..535B .
  11. Nelson JW, Hatch EE, Webster, TF. Exposure to Polyfluoroalkyl Chemicals and Cholesterol, Body Weight, and Insulin Resistance in the General U.S. Population. Environ. Health Perspect.. 118. 2. 197–202. 2009. 20123614. 2831917. 10.1289/ehp.0901165.
  12. Houde M, Wells RS, Fair PA, etal . Polyfluoroalkyl compounds in free-ranging bottlenose dolphins (Tursiops truncatus) from the Gulf of Mexico and the Atlantic Ocean. Environ. Sci. Technol. . 39 . 17 . 6591–8 . September 2005. 16190216 . 10.1021/es0506556. 2005EnST...39.6591H.
  13. Derek . Muir. Biomonitoring of perfluoroalkyl acids: An overview of the global and temporal trend data. Fluoros . Environment Canada - National Water Research Institute . 2009-01-11.
  14. News: Water Pollution Continues At Famous Russian Lake . ScienceDaily. 25 March 2008 . 11 January 2009.
  15. Houde M, Martin JW, Letcher RJ, Solomon KR, Muir DC . Biological monitoring of polyfluoroalkyl substances: A review. . 40 . 11 . 3463–73 . June 2006. 16786681 . 10.1021/es052580b. 2006EnST...40.3463H. Supporting Information (PDF).
  16. Web site: PFAS laws and Regulations . . 2020-11-17 . United States Environmental Protection Agency (EPA) . Washington, DC.
  17. Web site: Drinking Water Health Advisories for PFOA and PFOS . 2020-12-09 . EPA.
  18. Web site: Fact Sheet; PFOA & PFOS Drinking Water Health Advisories . November 2016 . EPA 800-F-16-003.
  19. Web site: Adoption of ground water quality standards and maximum contaminant levels for perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) . 2020-06-01 . New Jersey Department of Environmental Protection (NJDEP) . Trenton, NJ.
  20. News: Fallon . Scott . New Jersey becomes first state to regulate dangerous chemical PFNA in drinking water . 2018-09-06 . North Jersey Record . Woodland Park, NJ.
  21. Web site: 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 . 2018-09-04 . NJDEP . 50 N.J.R. 1939(a).
  22. Web site: Matheny . Keith . 3 August 2020 . Michigan's drinking water standards for these chemicals now among toughest in nation . live . https://web.archive.org/web/20220131152306/https://eu.freep.com/story/news/local/michigan/2020/08/03/tougher-pfas-standards-drinking-water-michigan/5574268002/ . 31 January 2022 . 31 March 2022 . Detroit Free Press.
  23. Web site: 3 August 2020 . New state drinking water standards pave way for expansion of Michigan's PFAS clean-up efforts . live . https://web.archive.org/web/20220103083526/https://www.michigan.gov/egle/0,9429,7-135--535602--,00.html . 3 January 2022 . 5 April 2022 . Michigan.gov.
  24. Web site: PFAS in food: EFSA assesses risks and sets tolerable intake . The European Food Safety Authority . 17 October 2020 . September 17, 2020.
  25. Web site: Assembly Bill No. 2762 . State of California . 10 October 2020 . September 30, 2020.

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