Chemistry:Perfluorononanoic acid

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Perfluorononanoic acid
Perfluorononanoic acid.svg
Perfluorononanoic acid 3D BS.png
Names
IUPAC name
Heptadecafluorononanoic acid
Other names
perfluoro-n-nonanoic acid, PFNA, perfluorononanoate, C9 PFCA
Identifiers
3D model (JSmol)
1897287
ChEBI
ChEMBL
ChemSpider
EC Number
  • 206-801-3
317302
UNII
Properties
C9HF17O2
Molar mass 464.08 g/mol
Appearance white crystalline powder
Melting point 59 to 62 °C (138 to 144 °F; 332 to 335 K)[4]
Boiling point 218 °C (424 °F; 491 K)[5]
9.5 g/L[1]
Solubility in other solvents polar organic solvents
Acidity (pKa) ~0[2][3]
Hazards
Main hazards Strong acid and suspected carcinogen
GHS pictograms GHS05: CorrosiveGHS07: HarmfulGHS08: Health hazard
GHS Signal word Danger
H302, H318, H332, H351, H360, H362, H372
P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P301+312, P304+312, P304+340, P305+351+338, P308+313, P310, P312, P314, P330, P405, P501
Related compounds
Related compounds
 Trifluoroacetic acid (TFA), Perfluorooctanoic acid (PFOA), Perfluorooctanesulfonic acid (PFOS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[6][7] 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.[8] Additionally, it is considered a probable degradation product of many other compounds.[9]

PFNA is the largest perfluorinated carboxylic acid surfactant. Fluorocarbon derivatives with terminal carboxylates are only surfactants when they possess five to nine carbons.[10] 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.[10][11] 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.[12] However, longer chain perfluorinated carboxylic acids (PFCAs) are considered more bioaccumulative and toxic.[13] PFNA is an agonist of the nuclear receptors PPARα and PPARγ.[12] 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.[14] and has also been found in human follicular fluid [15] 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.[16] 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.[17] PFNA has been detected in polar bears in concentrations over 400 parts per billion.[18] PFNA was the perfluorinated chemical measured in the highest concentration in Russian Baikal seals.[19] However, PFOS is the perfluorinated compound that dominates in most wildlife biomonitoring samples.[20]

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.[21] 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).[22] [23]

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.[24] The state had set a standard for PFNA in September 2018, with an MCL of 13 ppt.[25][26]

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.[27][28]

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.[29]

Product Restrictions

In 2020, a California bill was passed banning PFNA as an intentionally added ingredient from cosmetics.[30]

See also

References

  1. ↑ "Safety (MSDS) data for perfluorononanoic acid". PTCL Safety web site. http://msds.chem.ox.ac.uk/PE/perfluorononanoic_acid.html. 
  2. ↑ Goss KU (July 2008). "The pKa values of PFOA and other highly fluorinated carboxylic acids". Environ. Sci. Technol. 42 (2): 456–458. doi:10.1021/es702192c. PMID 18284146. Bibcode: 2008EnST...42..456G. 
  3. ↑ "Theoretical studies on the pKa values of perfluoroalkyl carboxylic acids". J. Mol. Struct. (Theochem) 949 (1–3): 60–69. June 2010. doi:10.1016/j.theochem.2010.03.003. 
  4. ↑ "Perfluorononanoic acid 97%". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=394459%7CALDRICH&N5=Product%20No.%7CBRAND_KEY&F=SPEC. 
  5. ↑ "Perfluorononanoic acid". ChemicalBook. http://www.chemicalbook.com/ChemicalProductProperty_EN.aspx?CBNumber=CB0211518. 
  6. ↑ "Sources, fate and transport of perfluorocarboxylates". Environ Sci Technol 40 (1): 32–44. January 2006. doi:10.1021/es0512475. PMID 16433330. Bibcode: 2006EnST...40...32P.  Supporting Information (PDF).
  7. ↑ "PERFORCE — PERFLUORINATED ORGANIC COMPOUNDS IN THE EUROPEAN ENVIRONMENT". Institute for Biodiversity and Ecosystem Dynamics, Universiteit van Amsterdam. 2006-09-15. pp. 18. http://www.science.uva.nl/perforce/Final%20reportA.pdf. Retrieved 2009-02-15. 
  8. ↑ "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. doi:10.1093/toxsci/kfl162. PMID 17093205. 
  9. ↑ "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. http://www.olis.oecd.org/olis/2006doc.nsf/LinkTo/NT00000F9A/$FILE/JT03231059.PDF. Retrieved 2008-09-19. 
  10. ↑ 10.0 10.1 Salager, Jean-Louis (2002). "FIRP Booklet # 300-A: Surfactants-Types and Uses". Universidad de los Andes Laboratory of Formulation, Interfaces Rheology, and Processes. pp. 44. http://nanoparticles.org/pdf/Salager-E300A.pdf. Retrieved 2008-09-07. 
  11. ↑ "Fluorosurfactant — Structure / Function". Mason Chemical Company. http://www.masonsurfactants.com/Products/Fluorosurfactant.htm. 
  12. ↑ 12.0 12.1 "Immunotoxic effects of perfluorononanoic acid on BALB/c mice". Toxicol. Sci. 105 (2): 312–21. October 2008. doi:10.1093/toxsci/kfn127. PMID 18583369. 
  13. ↑ "Cooking decreases observed perfluorinated compound concentrations in fish". Journal of Agricultural and Food Chemistry 56 (16): 7551–9. August 2008. doi:10.1021/jf800827r. PMID 18620413. 
  14. ↑ "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. doi:10.1289/ehp.10598. PMID 18007991. PMC 2072821. http://www.ehponline.org/members/2007/10598/10598.html. Retrieved 2009-01-11. 
  15. ↑ Bach, Cathrine Carlsen; Bech, Bodil Hammer; Nohr, Ellen Aagaard; Olsen, Jørn; Matthiesen, Niels Bjerregård; Bossi, Rossana; Uldbjerg, Niels; Bonefeld-Jørgensen, Eva Cecilie et al. (2015-10-01). "Serum perfluoroalkyl acids and time to pregnancy in nulliparous women". Environmental Research 142: 535–541. doi:10.1016/j.envres.2015.08.007. PMID 26282225. Bibcode: 2015ER....142..535B. 
  16. ↑ Nelson JW, Hatch EE, Webster, TF (2009). "Exposure to Polyfluoroalkyl Chemicals and Cholesterol, Body Weight, and Insulin Resistance in the General U.S. Population". Environ. Health Perspect. 118 (2): 197–202. doi:10.1289/ehp.0901165. PMID 20123614. 
  17. ↑ "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. doi:10.1021/es0506556. PMID 16190216. Bibcode: 2005EnST...39.6591H. 
  18. ↑ Muir, Derek. "Biomonitoring of perfluoroalkyl acids: An overview of the global and temporal trend data". Fluoros. Environment Canada - National Water Research Institute. http://www.chem.utoronto.ca/symposium/fluoros/pdfs/Fluoros-PFAbiomonitoring(Muir).pdf. Retrieved 2009-01-11. 
  19. ↑ "Water Pollution Continues At Famous Russian Lake". ScienceDaily. 25 March 2008. https://www.sciencedaily.com/releases/2008/03/080324103026.htm. 
  20. ↑ "Biological monitoring of polyfluoroalkyl substances: A review". Environ. Sci. Technol. 40 (11): 3463–73. June 2006. doi:10.1021/es052580b. PMID 16786681. Bibcode: 2006EnST...40.3463H.  Supporting Information (PDF).
  21. ↑ "PFAS laws and Regulations". Washington, DC: United States Environmental Protection Agency (EPA). 2020-11-17. https://www.epa.gov/pfas/pfas-laws-and-regulations. 
  22. ↑ "Drinking Water Health Advisories for PFOA and PFOS". EPA. 2020-12-09. https://www.epa.gov/ground-water-and-drinking-water/drinking-water-health-advisories-pfoa-and-pfos. 
  23. ↑ "Fact Sheet; PFOA & PFOS Drinking Water Health Advisories". November 2016. https://www.epa.gov/ground-water-and-drinking-water/supporting-documents-drinking-water-health-advisories-pfoa-and-pfos. 
  24. ↑ "Adoption of ground water quality standards and maximum contaminant levels for perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS)". Trenton, NJ: New Jersey Department of Environmental Protection (NJDEP). 2020-06-01. https://www.state.nj.us/dep/srp/srra/listserv_archives/2020/20200601_srra.html. 
  25. ↑ Fallon, Scott (2018-09-06). "New Jersey becomes first state to regulate dangerous chemical PFNA in drinking water". North Jersey Record (Woodland Park, NJ). https://www.northjersey.com/story/news/environment/2018/09/06/new-jersey-first-state-regulate-dangerous-chemical-pfna-pfoa/1210328002/. 
  26. ↑ "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". NJDEP. 2018-09-04. 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. 
  27. ↑ Matheny, Keith (3 August 2020). "Michigan's drinking water standards for these chemicals now among toughest in nation". https://www.freep.com/story/news/local/michigan/2020/08/03/tougher-pfas-standards-drinking-water-michigan/5574268002/. 
  28. ↑ "New state drinking water standards pave way for expansion of Michigan's PFAS clean-up efforts". 3 August 2020. https://www.michigan.gov/egle/0,9429,7-135--535602--,00.html. 
  29. ↑ "PFAS in food: EFSA assesses risks and sets tolerable intake". The European Food Safety Authority. September 17, 2020. https://www.efsa.europa.eu/en/news/pfas-food-efsa-assesses-risks-and-sets-tolerable-intake. 
  30. ↑ "Assembly Bill No. 2762". State of California. September 30, 2020. https://leginfo.legislature.ca.gov/faces/billTextClient.xhtml?bill_id=201920200AB2762. 

External links



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