Perfluorooctanoic acid

Perfluorooctanoic acid
Perfluorooctanoic acid visible in an emulsion
Names
Preferred IUPAC name
Pentadecafluorooctanoic acid
Other names
Perfluorooctanoic acid, PFOA, C8, Perfluorooctanoate, PFO, Perfluorocaprylic acid, C8-PFCA, FC-143, F-n-octanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.817
EC Number
  • 206-397-9
PubChem CID
RTECS number
  • RH0781000
UNII
InChI
  • InChI=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) Y
    Key: SNGREZUHAYWORS-UHFFFAOYSA-N Y
  • 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)
    Key: SNGREZUHAYWORS-UHFFFAOYAQ
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
Properties
Chemical formula
 C8HF15O2
Molar mass 414.07 g/mol
Appearance White solid
Density 1.8 g/cm3[1]
Melting point 40 to 50 °C (104 to 122 °F; 313 to 323 K)[1]
Boiling point 189 to 192 °C (372 to 378 °F; 462 to 465 K)[1]
Solubility in water
 Soluble, 9.5 g/L (PFO)[2]
Solubility in other solvents Polar organic solvents
Acidity (pKa) ~0[3][4][5]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Strong acid, known carcinogen and persistent organic pollutant
GHS labelling:
Pictograms
Signal word
 Danger
Hazard statements
 H302, H318, H332, H351, H360, H362, H372
Precautionary statements
 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
NFPA 704 (fire diamond)
3
0
0
Safety data sheet (SDS) [1]
Related compounds
Related compounds
  • Perfluorooctanesulfonic acid (PFOS), Perfluorononanoic acid (PFNA),Perfluorooctanesulfonamide (PFOSA), Trifluoroacetic acid (TFA)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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.[6]

The International Agency for Research on Cancer (IARC) has classified PFOA as carcinogenic to humans.[7] 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".[8] They can also move through soils and contaminate drinking water sources and can build up (bioaccumulate) in fish and wildlife.[8] Residues have been detected in humans and wildlife.[8][9]

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.[10] 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.[6][11] 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).[12]: 2  Eight other companies agreed to gradually phase out the manufacturing of the chemical by 2015.[12]: 3 

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

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.[12]: 1 

In 2024 EPA published drinking water regulations for PFOA and five other PFAS.[13]

  1. ^ a b c d Record of Perfluorooctanoic acid in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 5 November 2008.
  2. ^ Cite error: The named reference Prevedouros2006 was invoked but never defined (see the help page).
  3. ^ Goss K. U. (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.
  4. ^ Cheng J, Psillakis E, Hoffmann MR, Colussi AJ (July 2009). "Acid dissociation versus molecular association of perfluoroalkyl oxoacids: Environmental implications". J. Phys. Chem. A. 113 (29): 8152–8156. Bibcode:2009JPCA..113.8152C. doi:10.1021/jp9051352. PMID 19569653. Archived from the original on 2020-04-12. Retrieved 2019-12-04.
  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. ^ a b Lemal DM (January 2004). "Perspective on fluorocarbon chemistry". J. Org. Chem. 69 (1): 1–11. doi:10.1021/jo0302556. PMID 14703372.
  7. ^ 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 (November 2023). "Carcinogenicity of perfluorooctanoic acid and perfluorooctanesulfonic acid". The Lancet. Oncology. 25 (1): 16–17. doi:10.1016/S1470-2045(23)00622-8. PMC 12183505. PMID 38043561. S2CID 265571186.
  8. ^ a b c "Per- and Polyfluorinated Substances (PFAS) Factsheet | National Biomonitoring Program | CDC". www.cdc.gov. 2022-05-03. Archived from the original on 2022-12-22. Retrieved 2024-04-12.
  9. ^ "Emerging chemical risks in Europe — 'PFAS' — European Environment Agency". www.eea.europa.eu. 16 December 2019. Archived from the original on 2024-07-12. Retrieved 2024-04-12.
  10. ^ Lindstrom AB, Strynar MJ, Libelo EL (2011-08-25). "Polyfluorinated Compounds: Past, Present, and Future". Environ. Sci. Technol. 45 (19): 7954–7961. Bibcode:2011EnST...45.7954L. doi:10.1021/es2011622. PMID 21866930.
  11. ^ Cite error: The named reference Salager2002 was invoked but never defined (see the help page).
  12. ^ a b c Emerging Contaminants Perfluorooctane Sulfonate (PFOS) and Perfluorooctanoic Acid (PFOA) (Report). EPA. March 2014. 505-F-14-001. Archived from the original on 2023-10-22. Retrieved 2017-11-12. Fact sheet.
  13. ^ United States Environmental Protection Agency (EPA), Washington, D.C. (April 26, 2024). "PFAS National Primary Drinking Water Regulation." Federal Register, 89 FR 32532
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