| Compound Name |
Perfluorooctane sulfonic acid (PFOS), its salts and perfluorooctane sulfonyl fluoride |
| Stockholm Annex code | I, IV |
| 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 B with acceptable purposes and specific exemptions (decision SC-4/17) |
| Year of Listing Decision |
2009 |
| Persistence |
N/A |
| Specific exemptions associated with its use |
Production: For the use below |
| Acceptable purposes associated with its use |
The current intentional use of PFOS is widespread and includes: electric and electronic parts, fire fighting foam, photo imaging, hydraulic fluids and textiles. Clothing treatments and coating for paper and cardboard packaging PFOS, together with PFOA, has also been used to make aqueous film forming foam (AFFF), a component of fire-fighting foams, and alcohol-type concentrate foams. Used as a photographic emulsifier Used as an aviation hydraulic fluids systems Mainly used as sealing agents and adhesives. |
| Conventions on POPs |
Stockholm Convention Convention on Long-Range Transboundary Air Pollution Rotterdam Convention Basel Convention |
| Name |
Perfluorooctane sulfonic acid (PFOS), its salts and perfluorooctane sulfonyl fluoride |
| Synonyms |
Perfluorooctane sulfonyl fluoride (PFOSF) Heptadecafluorooctane-1-sulfonyl fluoride Perfluorooctanesulfonyl fluoride Heptadecafluorooctanesulphonyl fluoride Perfluoro-1-octanesulfonyl fluoride N-Perfluorooctanesulfonyl fluoride Perfluorooctylsulfonylfluoride Heptadecafluorooctane-1-sulfonyl fluoride 1-Octanesulfonyl fluoride, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro- Perfluorooctyl sulfonyl chloride DTXSID5027140 |
| Structure | (F)S(=O)(=O)F)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)(F)F.png)
Molecular Formula:
C8F18O2S
|
| CAS Number | 307-35-7 |
| European Community (EC) Number | 206-200-6 |
| European Chemicals Agency (ECHA) | 206-200-6 |
| PubChem ID | 9388 |
| DSSTOX Substance ID | DTXSID5027140 |
| KEGG | C18142 |
| ChemSpider |
9019 |
| Similarity threshold | Name of Related Compound | DSSTox Substance ID | CAS Number | Molecular weight | Molecular formula |
|---|---|---|---|---|---|
| 1.0 | Perfluorobutanesulfonyl fluoride | DTXSID20861913 | 375-72-4 | 302 g/mol | C4F10O2S |
| 1.0 | Perfluoropentanesulfonyl fluoride | DTXSID50880137 | 375-81-5 | 352 g/mol | C5F12O2S |
| 1.0 | Perfluorohexanesulphonyl fluoride | DTXSID3059973 | 423-50-7 | 402 g/mol | C6F14O2S |
| 1.0 | Perfluoroheptanesulphonyl fluoride | DTXSID9059830 | 335-71-7 | 452 g/mol | C7F16O2S |
| 1.0 | Perfluorononanesulfonyl fluoride | DTXSID3071351 | 68259-06-3 | 552 g/mol | C9F20O2S |
| 1.0 | Perfluorodecanesulphonyl fluoride | DTXSID5059795 | 307-51-7 | 602 g/mol | C10F22O2S |
| 0.96 | Octafluorobutane-1,4-disulfonyl difluoride | DTXSID00559644 | 84246-31-1 | 366 g/mol | C4F10O4S2 |
| 0.96 | Dodecafluorohexane-1,6-disulfonyl difluoride | DTXSID40614988 | 144368-88-7 | 466 g/mol | C6F14O4S2 |
| 0.93 | 1,2,2,3,3,4-Hexafluorobutane-1,4-disulfonyl difluoride | DTXSID50557352 | 90127-84-7 | 330 g/mol | C4H2F8O4S2 |
| 0.93 | 1,2,2,3,3,4,4,5,5,6-Decafluorohexane-1,6-disulfonyl difluoride | DTXSID90511175 | 84933-50-6 | 430 g/mol | C6H2F12O4S2 |
| 0.88 | 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonyldifluoride | DTXSID30456354 | 82727-16-0 | 316 g/mol | C3F8O4S2 |
| 0.84 | 1,2,2,3-Tetrafluoropropane-1,3-disulfonyl difluoride | DTXSID40529780 | 90127-86-9 | 280 g/mol | C3H2F6O4S2 |
| 0.84 | Cyclohexanesulfonyl fluoride, decafluoro(1,1,2,2,2-pentafluoroethyl)- | DTXSID90880590 | 68156-06-9 | 464 g/mol | C8F16O2S |
| 0.83 | Cyclohexanesulfonyl fluoride, undecafluoro- | DTXSID0059875 | 355-03-3 | 364 g/mol | C6F12O2S |
| 0.82 | Cyclohexanesulfonyl fluoride, decafluoro(trifluoromethyl)- | DTXSID50880612 | 68318-34-3 | 414 g/mol | C7F14O2S |
| 0.81 | 2,2,3,3,4,4-Hexafluoro-4-(fluorosulfonyl)butanoyl fluoride | DTXSID80468003 | 83071-23-2 | 280 g/mol | C4F8O3S |
| Description | Reference | Article Link |
|---|---|---|
| Perfluorinated compounds (PFCs) comprise a large group of chemicals that have been produced about 50 years. PFCs are fully fluorinated chemicals, which are man-made with unique properties and have been recognized as a class of emerging, persistent contaminants. Carbon-fluorine bonds are among the strongest in organic chemistry. This stability makes these compounds practically nonbiodegradable and persistent in the environment. Perfluorinated sulfonates, such as perfluorooctane sulfonate (PFOS), and perfluorinated carboxylates, such as perfluorooctanoic acid (PFOA), are not reactive, resist hydrolysis and photolysis, and are not easily degraded in biological systems, making them persistent in the environment. The fluorocarbon part is hydrophobic, lipophilic, and hence nonpolar, whereas the “tail” sections of the molecules add polarity since they are hydrophilic and lipophobic. Both PFOS and PFOA are fluorosurfactants that can drastically lower the surface tension of water. These chemicals are produced for numerous applications in industrial processes and are used to make consumer products, such as water-, oil-, and stain-resistant coatings for clothing fabrics, leather, and carpets, and oil-resistant coatings for paper products for food contact. They are also used in surfactants, photographic emulsifier, aviation hydraulic fluids, fire-fighting foams, floor polishes, and insecticide formulations. During the last two decades several reports have surfaced concerning toxicity of PFOS and PFOA in both humans and wildlife. | Viberg and Eriksson. 2017. Chapter 43 - Perfluorooctane Sulfonate and Perfluorooctanoic Acid. | Link |
| Perfluorinated compounds (PFCs) have been extensively used in a variety of industry and consumer products, such as surfactants, lubricants, adhesives, refrigerants, herbicide, paper coating, fire retardants, pesticide, propellants, and insecticides over the past few years. Among these compounds, perfluorooctane sulfonate (PFOS) has been found to be predominant and the most extensively distributed member of PFCs family. Several studies have revealed that PFOS accumulates in both humans and wildlife species, due to the widespread use and its chemical property characterized by resistance to environmental and metabolic degradation. Pharmacokinetic studies have shown that once PFOS is absorbed, it distributes and accumulates in the serum and liver, but is poorly eliminated. In humans, a mean serum elimination half-life of approximately 8.7 years was recently estimated from retired production workers. Due to its bioaccumulative nature and potential toxicities, PFOS was added among persistent organic pollutants listed under the Stockholm Convention in 2009. | Yao and Ma. 2016. Chapter 9 - Organic Pollutant Perfluorooctane Sulfonate–Induced Lysosomal Membrane Permeabilization Blocks Autophagy Flux in Human Hepatoma Cells. | Link |
| Concerns regarding the environmental persistence and the potential for bioaccumulation of two anionic perfluorinated surfactants perfluorooctanesulfonate and perfluorooctanoic acid prompted the primary manufacturer to phase out their production. The decision by the primary manufacturer to reduce production of commercial products was due in part to the detection of PFOS concentrations (10-100 µg/L) in human blood samples from the United States, Japan, Europe, and China and in biota samples. The PFOS concentrations measured in a variety of biota and environmental samples have raised questions concerning the mechanism(s) for their widespread dissemination of PFOS. Perfluorinated surfactants are employed for industrial and commercial applications and are used in lubricants, paints, polishes, food packaging, and fire-fighting foams. PFOS is an important perfluorinated surfactant as well as a precursor to other perfluorinated surfactants. In 2000, the estimated annual U.S. production quantity of PFOS was 2,943,769 kg, and as a result of the primary manufacturer’s phase out, the anticipated 2003 annual U.S. PFOS production will be 0 kg. Perfluoroalkanesulfonate salts and perfluorocarboxylates are present in fire-fighting foam formulations, including aqueous film forming foams (AFFFs). AFFFs are proprietary mixtures used to extinguish hydrocarbon fuel fires and are often found where there are large volumes of flammable liquids and the potential for a fire exists. For example, AFFFs are found at U.S. military bases, fire departments, and airports. Other components of AFFFs include diethylene glycol butyl ether, hydrocarbon surfactants, and corrosion inhibitors. Years of employing AFFFs in a variety of situations has resulted in these fire-fighting foam components being directly released to the environment and the contamination of groundwater | Moody et al., 2002. Monitoring Perfluorinated Surfactants in Biota and Surface Water Samples Following an Accidental Release of Fire-Fighting Foam into Etobicoke Creek. | Link |
| Perfluorooctane sulphonate (PFOS) and perfluorooctanoic acid (PFOA) and related compounds are members of a large family of perfluorinated chemicals (PFCs). Although available for the last 50 years, PFCs have been increasingly used as surfactants in a number of industrial and consumer products, mainly to repel dirt, water and oils. Their use has included performance chemicals such as photographic film, surfactant in fire-fighting foams, surfactant for alkaline cleaners, emulsifiers in floor polish, mist suppressant for metal plating baths, surfactant for etching acids for circuit boards, pesticides, and dirt-repellent treatments for textiles (e.g. carpets, home furnishings and leather) and paper (e.g. food containers and masking tape). PFOS-related chemicals are manufactured from a precursor material known as perfluorooctanesulphonyl fluoride (POSF). It has been estimated that the total global production/use (from 1970 to 2002) has been 96 000 tonnes of POSF, with total global emissions being 650–2600 tonnes of POSF and 6.5–130 tonnes of PFOS. Most of the environmental release is to water (98%) and the remainder to air. They are immobile in soil and are non-biodegradable in, for example, activated sewage sludge. | Rumsby et al., 2009. Perfluorooctane sulphonate and perfluorooctanoic acid in drinking and environmental waters. | Link |
| Perfluorooctane sulfonate (PFOS) and perfluorooctanoate (PFOA) are synthetic fluorinated organic compounds (FOCs). Having unique chemical and physical characteristics such as both hydrophobic and oleophobic nature, these chemicals have been manufactured world wide since 1950s, and used for various products such as textiles, clothes, carpet, paper coating, cosmetics, waterproof agents, and firefighting foams | Jin et al., 2009. PFOS and PFOA in environmental and tap water in China. | Link |
| Perfluorooctane sulfonate (PFOS) has recently emerged as a priority environmental pollutant due to its widespread detection in biotas including both Arctic and Antarctic species and its persistent and bioaccumulative nature. As the calculated Henry’s law value for PFOS is 4.7 × 10-9 atm‚m3/mol, it is unlikely to enter into the atmosphere directly and undergo global dissemination. As such, it has been hypothesized that PFOS must be globally distributed via more volatile, neutral airborne contaminants that undergo long-range transport to remote areas and degrade to yield the free acid. The mechanisms by which these neutral contaminants enter the environment may include release during manufacturing and application processes, leaching from both consumer products and waste products in landfills due to abiotic and/or biotic degradation processes, and/or the release of residual materials in the final products. Similarly, perfluoroalkyl carboxylates (PFCAs) where equals have recently been observed in biota. Currently the only known source of PFCAs to the environment is the thermolyis of fluoropolymers; other possible sources include the degradation of polyfluorinated alcohols. | Stock et al., 2004. Polyfluorinated telomer alcohols and sulfonamides in the North American troposphere. | Link |
| Perfluorinated compounds such as perfluorooctane sulfonate (PFOS) and perfluorooctane acid (PFOA) have been recognized as emerging environmental pollutants because of their ubiquitous occurrence in the environment, biota and humans. | Suja et a., 2009. Contamination, bioaccumulation and toxic effects of perfluorinated chemicals (PFCs) in the water environment: a review paper. | Link |