Substance Identity

Information on the identity of perfluorooctanoic acid (PFOA) is presented in Table 1. PFOA is an anthropogenic compound with a chain length of eight carbons, seven of which are perfluorinated. It belongs to the broad class of chemicals known as perfluorocarboxylic acids (PFCAs), which, in turn, belong to the broader class of chemicals known as perfluoroalkyls (PFAs). The term “PFOA” may refer to the acid, its conjugate base or its principal salt forms (Table 2). The term PFOA is not interchangeable with commercial mixtures containing PFOA, as these mixtures are often not well characterized and could include any product that contains even a small amount of PFOA. PFOA may also be referred to as C8, as well as by other synonyms or trade names. A more detailed discussion of the identity, nomenclature and trade names of PFOA is provided in Ellis et al. (2004b). The most common commercially used salt form of PFOA is the ammonium salt, referred to as APFO (see chemical structure in Table 1).

Table 1. Substance Identity

Chemical Abstracts Service Registry Number (CAS RN) 335-67-1
Chemical name Perfluorooctanoic acid
National Chemical Inventories (NCI) names1

Octanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro- (TSCA)

Octanoic acid, pentadecafluoro- (AICS, ASIA-PAC, NDSL, NZloC, PICCS, SWISS)

Pentadecafluorooctanoic acid (ECL, EINECS, PICCS, REACH)

Perfluorooctanoic acid (ENCS)

Other names EF 201; Eftop EF-201; NSC 95114; Pentadecafluoro-1-octanoic acid; Pentadecafluoro-n-octanoic acid; Perfluorocaprylic acid; Perfluoro-1-heptanecarboxylic acid; Perfluoroheptanecarboxylic acid; n-Perfluorooctanoic acid
Chemical group Discrete organics
Major chemical class or use Perfluoroalkyls
Major chemical subclass Perfluorocarboxylic acids
Chemical formula C8HF15O2
Chemical structure (salt and acid form)

Chemical structure of Perfluorooctanoic acid (ammonium salt form)
Ammonium Salt

Chemical structure of Perfluorooctanoic acid (acid form)
Acid

SMILES2 FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)O
1 NCI 2009 : AICS (Australian Inventory of Chemical Substances); ASIA-PAC (Asia-Pacific Substances Lists); ECL (Korean Existing Chemicals List); EINECS (European Inventory of Existing Commercial Chemical Substances); ENCS (Japanese Existing and New Chemical Substances); NDSL(Non-Domestic Substances List (Canada)); NZIoC (New Zealand Inventory of Chemicals); PICCS (Philippine Inventory of Chemicals and Chemical Substances); REACH (Registration, Evaluation, Authorisation and Restriction of Chemicals (European Commission); SWISS (Swiss Giftliste 1 and Inventory of Notified New Substances); TSCA (Toxic Substances Control Act Chemical Substance Inventory).
2 Simplified Molecular Input Line Entry Specification

Environment Canada considered perfluoroalkyl compounds on the basis of expert judgement, chemical structures and biodegradation estimation modelling using CATABOL (c2004–2008) (Mekenyan et al. 2002). Using these approaches, the structures were analyzed for their potential to degrade to PFOA. CATABOL (c2004–2008) was trained on the basis of the Japanese Ministry of International Trade and Industry (MITI) biodegradation test results and predicts biodegradation over a period of 28 days. It is acknowledged that due to the limited perfluorinated degradation data in the training set, some degradation products generated by CATABOL (c2004–2008) may be of limited reliability. It should be noted that the degradation process will be longer for perfluorinated chemicals, but it is difficult to estimate how much longer, especially for high-molecular-weight substances such as oligomers and polymers.

Precursors to PFOA (Table 2) have been considered in this assessment; however, this list should not be considered exhaustive. A more complete list can be found under the Notice with respect to certain perfluoroalkyl and fluoroalkyl substances at: https://www.canadagazette.gc.ca/rp-pr/p1/2005/2005-01-15/pdf/g1-13903.pdf (PDF 2.2 MB). It should also be noted that some precursors to PFOA may also be considered as precursors to long-chain (C9-C20) perfluorocarboxylic acids. This assessment defines precursors as substances where the perfluorinated alkyl moiety has the formula CnF2n+1 (where n= 7 or 8) and is directly bonded to any chemical moiety other than a fluorine, chlorine or bromine atom.

Table 2. List of PFOA and its Principal Salts and Precursors1

Name CAS RN Molecular formula Listing (DSL or NDSL)
PFOA free acid (Octanoic acid, pentadecafluoro-) 335-67-1 C8HF15O2 NDSL
Perfluorooctanoate (PFO, conjugate base of the free acid) 45285-51-6 C8F15O2- Not listed
Branched perfluorooctanoic acid 90480-55-0 C8HF15O2 Not listed
Principal salts
PFOA ammonium salt (APFO, Octanoic acid, pentadecafluoro-, ammonium salt) 3825-26-1 C8F15O2-NH4+ DSL
Ammonium salt, linear/branched PFOA (Octanoic acid, pentadecafluoro-, branched, ammonium salt) 90480-56-1 C8F15O2-NH4+ Not listed
PFOA sodium salt 335-95-5 C8F15O2-Na+ NDSL
PFOA potassium salt 2395-00-8 C8F15O2-K+ Not listed
PFOA silver salt 335-93-3 C8F15O2-Ag+ NDSL
Potential precursors1
2-Propenoic acid, 2-methyl-, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl ester, polymer with 2-propenoic acid 53515-73-4 (C15H11F15O4)x DSL
Propanamide, 3-[(γ-ω-perfluoro-C4–10-alkyl)thio] derivatives 68187-42-8 NA DSL
Poly(difluoromethylene), a-fluoro-ω-[2- [[2-(trimethylammonio)ethyl]thio]ethyl]-, methyl sulfate 65530-57-6 NA DSL
Poly(difluoromethylene), a,a'-[phosphinicobis( oxy-2,1-ethanediyl)]bis[ω-fluoro- 65530-62-3 NA DSL
Poly(difluoromethylene), a-fluoro-ω-[2-(phosphonooxy)ethyl]- 65530-61-2 NA DSL
Thiols, C8-20, γ-ω-perfluoro, telomers with acrylamide 70969-47-0 NA DSL
Carbamic acid, [2-(sulfothio)ethyl]-, C-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) ester, monosodium salt 82199-07-3 NA DSL
Carbamic acid, [2-(sulphothio)ethyl]-, C-(γ-ω-perfluoro-C6–9-alkyl) esters, monosodium salts 95370-51-7 NA DSL
1,3-Propanediol, 2,2-bis[[(γ-ω-perfluoro-C4–10-alkyl)thio]methyl] derivatives, phosphates, ammonium salts 148240-85-1 NA NDSL
1,3-Propanediol, 2,2-bis[[(γ-ω-perfluoro-C6–12-alkyl)thio]methyl] derivatives, phosphates, ammonium salts 148240-87-3 NA NDSL
Thiols, C4–20, γ-ω-perfluoro, co-telomers with acrylic acid and acrylamide NA NA Not listed
1-Decanol, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro (or 1,1,2,2-tetrahydroperfluoro-1-decanol or 8:2 fluorotelomer alcohol) 678-39-7 C10F17H5O DSL
Octanoyl fluoride, pentadecafluoro- 335-66-0 C8F16O NDSL
Octanoic acid, pentadecafluoro-, methyl ester 376-27-2 C9H3F15O2 NDSL
Octanoic acid, pentadecafluoro-, ethyl ester 3108-24-5 C10H5F15O2 NDSL
8:2 Fluorotelomer acrylate polymers2 NA NA NA
1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iododecane (C8-2 iodide) 2043-53-0 NA NA
2-propenoic acid, 2-methyl-, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl methacrylate (C8-2 methacrylate) 1996-88-9 NA DSL
2-propenoic acid, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl acrylate (C8-2 acrylate) 27905-45-9 NA DSL
3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene (C8-2 olefin) 21652-58-4 NA NA
Phosphoric acid surfactants (e.g., 8:2 polyfluoroalkyl phosphoric acid diester or 8:2 diPAP)4 NA x:2 diPAP (F(CF2)xCH2CH2O)2P(O)OH NA
Perfluorooctylsulfonamides3 NA F[CF2]8SO2NRR’ where R and R’ can be CH2CH2OH, CH3, CH2CH3, or H NA
1,3-Propanediol, 2,2-bis[[(γ-ω-perfluoro-C10-20-alkyl)thio]methyl] derivs., phosphates, ammonium salts 148240-89-5 NA NDSL
Oxirane, methyl-, polymer with oxirane, mono[2-hydroxy-3-[( γ-ω-perfluoro-C8-20-alkyl)thio]propyl] ethers 183146-60-3 NA NDSL
Poly(difluoromethylene), a-fluoro-ω-(2-sulfoethyl)- 80010-37-3 NA NDSL
2-Propenoic acid, 3,3,4,4,5,5,6,
6,7,7,8,8,9,9,10,10,11,11,12,12,12-heneicosafluorododecyl ester, polymer with 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl 2-propenoate, alpha-
(2-methyl-1-1-oxo-2-2-propenyl)-omega-[(2-methyl-1-oxo-2-propenyl)oxy]poly(oxy-1, 2-ethanediyl), 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,
11,11,12,12,13,13,14,14,15,15,16,16,16-nonacosafluorohexadecyl 2-propenoate, octadecyl 2-propenoate, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,
10,11,11,12,12,13,13,14,14,14-pentacosafluorotetradecyl 2-propenoate and 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,
11,11,12,12,13,13,14,14,15,15,16,
16,17,17,18,18,18-tritriacontafluorooctadecyl 2-propenoate
116984-14-6 NA not listed
Pentanoic acid, 4,4-bis[(γ-ω-perfluoro-C8-20-alkyl)thio]derivs., compds. with diethanolamine 71608-61-2 NA NDSL
CAS RN, Chemical Abstracts Service Registry Number; DSL, Domestic Substances List; NA, not available; NDSL, Non-Domestic Substances List.
1 Precursors are as identified through CATABOL (c2004–2008), expert judgment, and literature and are non-exhaustive.
2 Van Zelm et al. (2008)
3 De Silva et el. (2009)
4 D’Eon and Mabury (2007)

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