Perfluorononanoic acid

Last updated
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
ECHA InfoCard 100.006.184 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-801-3
317302
PubChem CID
UNII
  • InChI=1S/C9HF17O2/c10-2(11,1(27)28)3(12,13)4(14,15)5(16,17)6(18,19)7(20,21)8(22,23)9(24,25)26/h(H,27,28) X mark.svgN
    Key: UZUFPBIDKMEQEQ-UHFFFAOYSA-N X mark.svgN
  • OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
Properties
C9HF17O2
Molar mass 464.08 g/mol
Appearancewhite crystalline powder
Melting point 59 to 62 °C (138 to 144 °F; 332 to 335 K) [1]
Boiling point 218 °C (424 °F; 491 K) [2]
9.5 g/L [3]
Solubility in other solventspolar organic solvents
Acidity (pKa)~0 [4] [5]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Strong acid and suspected carcinogen
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H302, H318, H332, H351, H360, H362, H372
P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P301+P312, P304+P312, P304+P340, P305+P351+P338, P308+P313, 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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

Related Research Articles

<span class="mw-page-title-main">Perfluorooctanoic acid</span> Perfluorinated carboxylic acid

Perfluorooctanoic acid is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in chemical processes and as a material feedstock. 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.

<span class="mw-page-title-main">Perfluorooctanesulfonic acid</span> Fluorosurfactant and persistent organic pollutant

Perfluorooctanesulfonic acid (PFOS) is a chemical compound having an eight-carbon fluorocarbon chain and a sulfonic acid functional group, and thus it is a perfluorosulfonic acid and a perfluoroalkyl substance (PFAS). It is an anthropogenic (man-made) fluorosurfactant, now regarded as a global pollutant. PFOS was the key ingredient in Scotchgard, a fabric protector made by 3M, and related stain repellents. The acronym "PFOS" refers to the parent sulfonic acid and to various salts of perfluorooctanesulfonate. These are all colorless or white, water-soluble solids. Although of low acute toxicity, PFOS has attracted much attention for its pervasiveness and environmental impact. It was added to Annex B of the Stockholm Convention on Persistent Organic Pollutants in May 2009.

<span class="mw-page-title-main">Microwave popcorn</span> Type of convenience food

Microwave popcorn is a convenience food consisting of unpopped popcorn in an enhanced, sealed paper bag intended to be heated in a microwave oven. In addition to the dried corn, the bags typically contain cooking oil with sufficient saturated fat to solidify at room temperature, one or more seasonings, and natural or artificial flavorings or both.

Scotchgard is a 3M brand of products, a stain repellent and durable water repellent applied to fabrics, upholstery, and carpets to protect them from stains. Scotchgard products typically rely on organofluorine chemicals as the main active ingredient along with petroleum distillate solvents.

Drinking water quality in the United States is generally safe. In 2016, over 90 percent of the nation's community water systems were in compliance with all published U.S. Environmental Protection Agency standards. Over 286 million Americans get their tap water from a community water system. Eight percent of the community water systems—large municipal water systems—provide water to 82 percent of the US population. The Safe Drinking Water Act requires the US EPA to set standards for drinking water quality in public water systems. Enforcement of the standards is mostly carried out by state health agencies. States may set standards that are more stringent than the federal standards.

Per- and polyfluoroalkyl substances are a group of synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain; there are 7 million such chemicals according to PubChem. PFAS came into use after the invention of Teflon in 1938 to make fluoropolymer coatings and products that resist heat, oil, stains, grease, and water. They are now used in products including waterproof fabric such as Nylon, yoga pants, carpets, shampoo, feminine hygiene products, mobile phone screens, wall paint, furniture, adhesives, food packaging, heat-resistant non-stick cooking surfaces such as Teflon, firefighting foam, and the insulation of electrical wire. PFAS are also used by the cosmetic industry in most cosmetics and personal care products, including lipstick, eye liner, mascara, foundation, concealer, lip balm, blush, and nail polish.

Fluorotelomer alcohols, or FTOHs, are fluorotelomers with an alcohol functional group. They are volatile precursors to perfluorinated carboxylic acids, such as PFOA and PFNA, and other compounds.

<span class="mw-page-title-main">Perfluorobutanesulfonic acid</span> Chemical compound

Perfluorobutanesulfonic acid (PFBS) is a PFAS chemical compound having a four-carbon fluorocarbon chain and a sulfonic acid functional group. It is stable and unreactive because of the strength of carbon–fluorine bonds. It can occur in the form of a colorless liquid or a corrosive solid. Its conjugate base is perfluorobutanesulfonate which functions as the hydrophobe in fluorosurfactants.

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

<span class="mw-page-title-main">Perfluorinated compound</span> Type of organic chemical

A perfluorinated compound (PFC) or perfluoro compound is an organofluorine compound that lacks C-H bonds. Many perfluorinated compounds have properties that are quite different from their C-H containing analogues. Common functional groups in PFCs are OH, CO2H, chlorine, O, and SO3H. Electrofluorination is the predominant method for PFC production. Due to their chemical stability, some of these perfluorinated compounds bioaccumulate.

Perfluoroalkyl carboxylic acids (PFCAs), or perfluorocarboxylic acids are compounds of the formula CnF(2n+1)CO2H that belong to the class of per- and polyfluoroalkyl substances. The simplest example is trifluoroacetic acid. These compounds are organofluorine analogues of ordinary carboxylic acids, but they are stronger by several pKa units and they exhibit great hydrophobic character. Perfluoroalkyl dicarboxylic acids (PFdiCAs) are also known, e.g. C2F4(CO2H)2.

Surflon S-111 is a commercial product consisting of perfluorinated carboxylic acids (PFCAs) in ammonium salt form. It is commonly used as a polymerization aid in the production of fluoropolymers.

<span class="mw-page-title-main">Perfluorooctanesulfonamide</span> Chemical compound

Perfluorooctanesulfonamide (PFOSA) is a synthetic organofluorine compound. It is a fluorocarbon derivative and a perfluorinated compound, having an eight-carbon chain and a terminal sulfonamide functional group. PFOSA, a persistent organic pollutant, was an ingredient in 3M's former Scotchgard formulation from 1956 until 2003, and the compound was used to repel grease and water in food packaging along with other consumer applications. It breaks down to form perfluorooctane sulfonate (PFOS). The perfluorooctanesulfonyl fluoride-based chemistry that was used to make sulfonamides like PFOSA was phased out by 3M in the United States (US) during 2000–2002 but it has grown in China by other producers.

<span class="mw-page-title-main">Perfluorobutanoic acid</span> Chemical compound

Perfluorobutanoic acid (PFBA) is a perfluoroalkyl carboxylic acid with the formula C3F7CO2H. As the perfluorinated derivative of butyric acid, this colourless liquid is prepared by electrofluorination of the corresponding butyryl fluoride.

<span class="mw-page-title-main">Perfluorooctanesulfonyl fluoride</span> Chemical compound

Perfluorooctanesulfonyl fluoride (POSF) is a synthetic perfluorinated compound with a sulfonyl fluoride functional group. It is used to make perfluorooctanesulfonic acid (PFOS) and PFOS-based compounds. These compounds have a variety of industrial and consumer uses, but POSF-derived substances ultimately degrade to form PFOS.

<span class="mw-page-title-main">FRD-903</span> Chemical compound

FRD-903 is a chemical compound that is among the class of per- and polyfluoroalkyl substances (PFASs). More specifically, this synthetic petrochemical is also described as a perfluoroalkyl ether carboxylic acid (PFECA) and a Fluorointermediate. It is not biodegradable and is not hydrolyzed by water.

GenX is a Chemours trademark name for a synthetic, short-chain organofluorine chemical compound, the ammonium salt of hexafluoropropylene oxide dimer acid (HFPO-DA). It can also be used more informally to refer to the group of related fluorochemicals that are used to produce GenX. DuPont began the commercial development of GenX in 2009 as a replacement for perfluorooctanoic acid, in response to legal action due to the health effects and ecotoxicity of PFOA.

Perfluorodecanoic acid (PFDA) is a fluorosurfactant and has been used in industry.

This timeline of events related to per- and polyfluoroalkyl substances (PFASs) includes events related to the discovery, development, manufacture, marketing, uses, concerns, litigation, regulation, and legislation, involving the human-made PFASs. The timeline focuses on some perfluorinated compounds, particularly perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) and on the companies that manufactured and marketed them, mainly DuPont and 3M. An example of PFAS is the fluorinated polymer polytetrafluoroethylene (PTFE), which has been produced and marketed by DuPont under its trademark Teflon. GenX chemicals and perfluorobutanesulfonic acid (PFBS) are organofluorine chemicals used as a replacement for PFOA and PFOS.

<span class="mw-page-title-main">Perfluorohexanesulfonic acid</span> Chemical compound

Perfluorohexanesulfonic acid (PFHxS) is a synthetic chemical compound. It is one of many compounds collectively known as per- and polyfluoroalkyl substances (PFASs). It is an anionic fluorosurfactant and a persistent organic pollutant with bioaccumulative properties. Although the use of products containing PFHxS and other PFASs have been banned or are being phased out in many jurisdictions, it remains ubiquitous in many environments and within the general population, and is one of the most commonly detected PFASs.

References

  1. ↑ "Perfluorononanoic acid 97%". Sigma-Aldrich. Retrieved 11 January 2009.
  2. ↑ "Perfluorononanoic acid". ChemicalBook. Archived from the original on 13 June 2018. Retrieved 11 January 2009.
  3. ↑ "Safety (MSDS) data for perfluorononanoic acid". PTCL Safety web site. Archived from the original on 1 April 2009. Retrieved 11 January 2009.
  4. ↑ Goss KU (July 2008). "The pKa values of PFOA and other highly fluorinated carboxylic acids". Environ. Sci. Technol. 42 (2): 456–458. Bibcode:2008EnST...42..456G. doi:10.1021/es702192c. PMID   18284146.
  5. ↑ Rayne S, Forest K (June 2010). "Theoretical studies on the pKa values of perfluoroalkyl carboxylic acids". J. Mol. Struct. (Theochem). 949 (1–3): 60–69. doi:10.1016/j.theochem.2010.03.003.
  6. ↑ Prevedouros K, Cousins IT, Buck RC, Korzeniowski SH (January 2006). "Sources, fate and transport of perfluorocarboxylates". Environ Sci Technol. 40 (1): 32–44. Bibcode:2006EnST...40...32P. doi:10.1021/es0512475. PMID   16433330. Supporting Information (PDF)
  7. ↑ PERFORCE — PERFLUORINATED ORGANIC COMPOUNDS IN THE EUROPEAN ENVIRONMENT (PDF). Institute for Biodiversity and Ecosystem Dynamics, Universiteit van Amsterdam. 2006-09-15. p. 18. Retrieved 2009-02-15.{{cite conference}}: CS1 maint: others (link)
  8. ↑ Henderson WM, Smith MA (February 2007). "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. doi: 10.1093/toxsci/kfl162 . PMID   17093205.
  9. ↑ Lists of PFOS, PFAS, PFOA, PFCA, related compounds and chemicals that may degrade to PFCA (PDF). 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. Retrieved 2008-09-19.{{cite conference}}: CS1 maint: others (link)
  10. 1 2 Salager, Jean-Louis (2002). FIRP Booklet # 300-A: Surfactants-Types and Uses (PDF). Universidad de los Andes Laboratory of Formulation, Interfaces Rheology, and Processes. p. 44. Archived from the original (PDF) on 2020-07-31. Retrieved 2008-09-07.
  11. ↑ "Fluorosurfactant — Structure / Function". Mason Chemical Company. Archived from the original on 5 July 2008. Retrieved 11 January 2009.
  12. 1 2 Fang X, Zhang L, Feng Y, Zhao Y, Dai J (October 2008). "Immunotoxic effects of perfluorononanoic acid on BALB/c mice". Toxicol. Sci. 105 (2): 312–21. doi: 10.1093/toxsci/kfn127 . PMID   18583369.
  13. ↑ Del Gobbo L, Tittlemier S, Diamond M, et al. (August 2008). "Cooking decreases observed perfluorinated compound concentrations in fish". Journal of Agricultural and Food Chemistry. 56 (16): 7551–9. doi:10.1021/jf800827r. PMID   18620413.
  14. ↑ Calafat AM, Wong LY, Kuklenyik Z, Reidy JA, Needham LL (November 2007). "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. doi:10.1289/ehp.10598. PMC   2072821 . PMID   18007991. Archived from the original on 2009-01-20. 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; Henriksen, Tine Brink (2015-10-01). "Serum perfluoroalkyl acids and time to pregnancy in nulliparous women". Environmental Research. 142: 535–541. Bibcode:2015ER....142..535B. doi:10.1016/j.envres.2015.08.007. PMID   26282225.
  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. PMC   2831917 . PMID   20123614.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  17. ↑ Houde M, Wells RS, Fair PA, et al. (September 2005). "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. Bibcode:2005EnST...39.6591H. doi:10.1021/es0506556. PMID   16190216.
  18. ↑ Muir, Derek. Biomonitoring of perfluoroalkyl acids: An overview of the global and temporal trend data (PDF). Fluoros. Environment Canada - National Water Research Institute. Retrieved 2009-01-11.
  19. ↑ "Water Pollution Continues At Famous Russian Lake". ScienceDaily. 25 March 2008. Retrieved 11 January 2009.
  20. ↑ Houde M, Martin JW, Letcher RJ, Solomon KR, Muir DC (June 2006). "Biological monitoring of polyfluoroalkyl substances: A review". Environ. Sci. Technol. 40 (11): 3463–73. Bibcode:2006EnST...40.3463H. doi:10.1021/es052580b. PMID   16786681. Supporting Information (PDF).
  21. ↑ "PFAS laws and Regulations". Washington, DC: United States Environmental Protection Agency (EPA). 2020-11-17.
  22. ↑ "Drinking Water Health Advisories for PFOA and PFOS". EPA. 2020-12-09.
  23. ↑ "Fact Sheet; PFOA & PFOS Drinking Water Health Advisories". November 2016. EPA 800-F-16-003.
  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.
  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.
  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. 50 N.J.R. 1939(a).
  27. ↑ Matheny, Keith (3 August 2020). "Michigan's drinking water standards for these chemicals now among toughest in nation". Detroit Free Press. Archived from the original on 31 January 2022. Retrieved 31 March 2022.
  28. ↑ "New state drinking water standards pave way for expansion of Michigan's PFAS clean-up efforts". Michigan.gov. 3 August 2020. Archived from the original on 3 January 2022. Retrieved 5 April 2022.
  29. ↑ "PFAS in food: EFSA assesses risks and sets tolerable intake". The European Food Safety Authority. September 17, 2020. Retrieved 17 October 2020.
  30. ↑ "Assembly Bill No. 2762". State of California. September 30, 2020. Retrieved 10 October 2020.
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