| Compound Name |
Perfluorooctanoic acid (PFOA), its salts and PFOA-related compounds |
| Stockholm Annex code | I |
| Key |
Annex I to the regulation are subject to prohibition (with specific exemptions) on manufacturing, placing on the market and use; Annex II to the regulation are subject to restriction on manufacturing, placing on the market and use; Annex III to the regulation are subject to release reduction provisions; and Annex IV to the regulation are subject to waste management provisions. Note that for some substances listed in Annex I, specific exemptions on the prohibition of their use, manufacturing and placing on the market may apply. |
| Classification |
Intentional |
| Category |
Listed under Annex A with specific exemptions (decision SC-9/12) |
| Year of Listing Decision |
2001 |
| Persistence |
PFOA has an average elimination half-life of about 3 years in humans. The half life os some PFOAs is estimated to be between 2 to 10 years. |
| Specific exemptions associated with its use |
Still being produced in some countries worldwide. |
| Acceptable purposes associated with its use |
PFOA is chiefly used as a material feedstock to produce its salts, which are used in the production of fluoropolymers and fluoroelastomers. It is also used as a industrial surfactant in the emulsion polymerization of fluoropolymers PFOA also has several industrial applications, that include apparel, carpeting, floor wax, upholstery, textiles, fire fighting foam and sealants. |
| Conventions on POPs |
Stockholm Convention Convention on Long-Range Transboundary Air Pollution Rotterdam Convention Basel Convention |
| Name |
Perfluorooctanoic acid (PFOA), its salts and PFOA-related compounds |
| Synonyms |
Perfluorooctanoic acid Pentadecafluorooctanoic acid Octanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro- 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctanoic acid Acide pentadecafluorooctanoique Perfluorooctanoic acid (PFOA) Pentadecafluorooctanoic acid CAS 335-67-1 Perfluoroheptanecarboxylic acid Perfluorooctanoic acid, 96% Pentadecafluoro-n-octanoic acid |
| Structure | (C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O.png)
Molecular Formula:
C8HF15O2
|
| CAS Number | 335-67-1 |
| European Community (EC) Number | 206-397-9 |
| European Chemicals Agency (ECHA) | 206-397-9 |
| PubChem ID | 9554 |
| DSSTOX Substance ID | DTXSID8031865 |
| KEGG | N/A |
| ChemSpider |
9180 |
| Similarity threshold | Name of Related Compound | DSSTox Substance ID | CAS Number | Molecular weight | Molecular formula |
|---|---|---|---|---|---|
| 1.0 | Perfluorooctanesulfonamide | DTXSID3038939 | 754-91-6 | 499 g/mol | C8H2F17NO2S |
| 1.0 | Perfluoropentanoate | DTXSID00892487 | 45167-47-3 | 263 g/mol | C5F9O2 |
| 1.0 | Perfluoropentanoic acid | DTXSID6062599 | 2706-90-3 | 264 g/mol | C5HF9O2 |
| 1.0 | Perfluorohexanoate | DTXSID20892484 | 92612-52-7 | 313 g/mol | C6F11O2 |
| 1.0 | Perfluorohexanoic acid | DTXSID3031862 | 307-24-4 | 314 g/mol | C6HF11O2 |
| 1.0 | Undecafluorohexan(2H)oic acid | DTXSID90892719 | NOCAS_892719 | 315 g/mol | C6DF11O2 |
| 1.0 | Perfluoroheptanoate | DTXSID60892483 | 120885-29-2 | 363 g/mol | C7F13O2 |
| 1.0 | Perfluoroheptanoic acid | DTXSID1037303 | 375-85-9 | 364 g/mol | C7HF13O2 |
| 1.0 | Perfluorooctanoate ion(1-) | DTXSID40892486 | 45285-51-6 | 413 g/mol | C8F15O2 |
| 1.0 | Pentadecafluoro(1-13C)octanoic acid | DTXSID70892570 | 864071-09-0 | 415 g/mol | C7CHF15O2 |
| Description | Reference | Article Link |
|---|---|---|
| Perfluoroalkyl and polyfluoroalkyl substances (PFASs) are manufactured organic chemicals in which the hydrogen atoms in the alkyl chain of the parent compound are completely (prefix: per-) or partially (prefix: poly-) replaced by fluorine atoms. Polyfluorinated substances have the potential to be degraded into perfluoroalkyl substances by biological or abiotic processes. PFAS molecule includes a hydrophilic functional head and a hydrophobic tail of varying carbon length. PFASs are often divided into long-chain PFASs and short-chain PFASs. The former refers to perfluoroalkyl carboxylic acids (PFCAs) with seven and more fluorinated carbons and perfluoroalkyl sulfonates (PFSAs) with six and more fluorinated carbons, and substances that have the potential to be degraded to long-chain perfluoroalkyl acids (PFAAs). | Buck et al., 2011. Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology, classification, and origins. | Link |
| The perfluoroalkyl acids (PFAA) are a family of perfluorinated chemicals that consist of a carbon backbone typically 4–14 in length and a charged functional moiety (primarily carboxylate, sulfonate, or phosphonate). The two most widely known PFAAs contain an eight-carbon backbone and include perfluorooctanoic acid (PFOA) and perfluorooctane sulfate (PFOS). It should be noted that PFAAs are different from another class of perfluorocarbons, the perfluoroalkanes, which are primarily used clinically for oxygenation and respiratory ventilation. PFAAs are relatively contemporary chemicals, being in use only in the past half century, and until recently, have been considered biologically inactive. | Lau et al., 2007. Perfluoroalkyl Acids: A Review of Monitoring and Toxicological Findings | Link |
| Perfluorooctanoic Acid (PFOA) is a synthetic chemical discovered in the mid-20th century by a well established chemical company. The term PFOA is used to describe not only the carboxylic acid C8HF15O2, but also a family of perfluorinated chemicals including perfluorooctanoic salts. PFOA is also sometimes referred to as gC8h which the amount of carbon chains found the molecule. Widespread interest in the health impacts of PFOA has been sparked due to recent media attention to this chemical and EPA scrutiny of PFOA. This paper was written to inform the reader about PFOAis chemical composition, historical use and production, known toxicity, and actions taken by the EPA and state agencies regarding regulations. | Moore. 2010. Overview Of Perfluorooctanoic Acid | Link |
| Perfluorooctanoic acid (PFOA) (conjugate base perfluorooctanoate)—also known colloquially as C8—is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in chemical processes and as a material feedstock, and is a health concern and subject to regulatory action and voluntary industrial phase-outs. PFOA is considered a surfactant, or fluorosurfactant, due to its chemical structure consisting of a perfluorinated, n-octyl "tail group" and a carboxylate "head group". The head group can be described as hydrophilic while the fluorocarbon tail is both hydrophobic and lipophobic. The tail group is inert and does not interact strongly with polar or non-polar chemical moieties; the head group is reactive and interacts strongly with polar groups, specifically water. The "tail" is hydrophobic due to being non-polar and lipophobic because fluorocarbons are less susceptible to the London dispersion force than hydrocarbons | Wikipedia: Perfluorooctanoic acid. Accessed on 14 October 2020 | Link |
| Perfluorooctanoic acid (‘PFOA’), its salts and PFOA-related substances have some specific properties such as high friction resistance, dielectricality, resistance to heat and chemical agents, and low surface energy. They are used in a wide variety of applications such as in the fluoropolymer and fluoroelastomer production, as surfactants in fire fighting foams, and in textile and paper production to provide water, grease, oil and/or dirt repellency. PFOA is identified as a persistent, bioaccumulative and toxic substance (‘PBT’) and was included in the Candidate List of Substances of Very High Concern (‘SVHC’) in 2013. PFOA-related substances are substances that, based on their molecular structure, are considered to have the potential to degrade or be transformed to PFOA | ChemSafetyPRO: Perfluorooctanoic acid (PFOA), its salts and PFOA-related substances. Accessed 14 October 2020 | Link |
| Perfluorooctane sulfonic acid [PFOS, C8F17SO3H] and perfluorooctanoic acid [PFOA, C7F15COOH] are among the most prominent organic pollutants in the environment, biota and human serum. The compounds are highly persistent and can undergo long-distance transport. The bioaccumulation potential and toxicity demonstrated in laboratory animals suggest a cause of great concern for the environment and human health. . Due to the wide global distribution and hazardous properties of PFOS and PFOA, manufacturing and use of the compounds and related perfluoroalkyl and polyfluoroalkyl substances (PFAS) have been reduced or restricted in recent years. PFOS was phased out of production during 2000–2002 in North America, banned in European countries, and was included in the Stockholm Convention on Persistent Organic Pollutants as an Annex B substance. Even though the total global PFOS production has fallen compared to the years prior to 2002, PFOS production has increased dramatically in China since 2003. Through a global stewardship program, PFOA and its longer chained homologues and chemical precursors are on track to be phased out by 2015 by major manufacturers. As the direct emissions of PFOA and PFOS have been declining in recent years, various PFASs that eventually are converted into PFOS, PFOA and other perfluoroalkyl acids (PFAA) are now key factors for determining the exposure and effect of PFASs. Subsequently, a primary research interest is to what extent the concentrations of perfluoroalkyl carboxylic acids [PFCA, CnF2n + 1COOH] and sulfonic acids [PFSA, CnF2n + 1SO3H], in particular PFOS and PFOA, originate from the breakdown of non-fluorinated functionalities, or even polyfluoroalkyl and perfluoroalkyl moieties in the environment. | Liu and Mejia-Avendano. 2013. Microbial degradation of polyfluoroalkyl chemicals in the environment: A review | Link |
| PFOA (Penta-decafluoro-octanoic acid), its salts and PFOA-related compounds fall within a family of perfluoroalkyl and polyfluoroalkyl substances (PFASs). PFASs consist of carbon chains of different lengths where the hydrogen atoms are completely (perfluorinated) or partly (polyfluorinated) substituted by fluorine atoms. The very stable bond between carbon and fluorine is only breakable with high energy input. Therefore, perfluorinated acids such as PFOA are not degradable in the environment. Certain polyfluorinated substances can be degraded to persistent perfluorinated substances such as PFOA under environmental conditions and are therefore precursors. Those PFASs, which can be degraded to PFOA in the environment, are referred to as PFOA-related compounds | GreenFacts: Perfluorooctanoic acid (PFOA). Accessed 14 October 2020 | Link |