Perfluorooctanesulfonic acid

Perfluorooctanesulfonic acid (conjugate base perfluorooctanesulfonate) (PFOS) is an anthropogenic fluorosurfactant and global pollutant. PFOS was the key ingredient in Scotchgard, a fabric protector made by 3M, and numerous stain repellents. It was added to Annex B of the Stockholm Convention on Persistent Organic Pollutants in May 2009.[4] PFOS can be synthesized in industrial production or result from the degradation of precursors. PFOS levels that have been detected in wildlife are considered high enough to affect health parameters, and recently higher serum levels of PFOS were found to be associated with increased risk of chronic kidney disease in the general US population.[5] "This association was independent of confounders such as age, sex, race/ethnicity, body mass index, diabetes, hypertension, and serum cholesterol level."[5]

Perfluorooctanesulfonic acid
Names
Systematic IUPAC name
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluoro-1-octanesulfonic acid[1]
Other names
PFOS
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.015.618
EC Number
  • 217-179-8
KEGG
UNII
Properties
C8HF17O3S
Molar mass 500.13 g/mol
Boiling point 133 °C (271 °F; 406 K) at 6 torr
Acidity (pKa) <<0[2][3]
Hazards
GHS pictograms
GHS Signal word Danger
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
3
0
Related compounds
Related compounds
 Perfluorooctanoic acid (PFOA), Perfluorobutanesulfonic acid (PFBS), Perfluorooctanesulfonamide (PFOSA), Perfluorononanoic acid (PFNA)
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

History

In 1949, 3M began producing PFOS-based compounds by electrochemical fluorination resulting in the synthetic precursor perfluorooctanesulfonyl fluoride.[6] In 1968, organofluorine content was detected in the blood serum of consumers, and in 1976 it was suggested to be PFOA or a related compound such as PFOS.[7][8][9] In 1997, 3M detected PFOS in blood from global blood banks,[10] although the company's internal documents indicate knowledge of this decades earlier, dating from the 1970s.[11] In 1999, the U.S. Environmental Protection Agency began investigating perfluorinated compounds after receiving data on the global distribution and toxicity of PFOS, the key ingredient in Scotchgard.[12] For these reasons, and USEPA pressure,[13] the primary American producer of PFOS, 3M, announced, in May 2000, the phaseout of the production of PFOS, PFOA, and PFOS-related products.[14][11] PFOS and PFOS-related chemicals are currently produced in China.[15]

Advances in analytical chemistry in recent years have allowed the routine detection of low- and sub-ppb levels of PFOS in food, wildlife, and humans.

Synthesis

Two primary methods are used for the industrial scale production of PFOS: electrophilic (or electrochemical) fluorination (ECF) and telomerization. ECF is an electrolysis production method where a precursor of perfluorooctanesulfonyl fluoride is dispersed in a solution of hydrofluoric acid and electrified. This production method, whilst economic and mainly results in PFOS, also results in shorter chain perfluoroalkyl substances being formed. PFOS predominates in the resultant mixture, however, if the reaction is allowed to continue this begins to favor the production of shorter chain PFAS. A distinct isomer ratio has been observed in PFOS produced by ECF, in the order of 70% linear PFOS, 25% branched and 5% terminal; this is not a function of the production process but rather that the precursor also exhibits this isomer ratio. ECF was the means by which 3M produced PFOS up until May 2000 when the company announced a phaseout of fluorosurfactants.

Telomerisation involves constructing the PFOS molecule using short chain (often 2-carbon) moieties and adding a sulfonate group as a final step. This production process results in 100% linear PFOS. This production method, whilst cleaner and resulting in a much more pure product than ECF, is not known to have been widely used except for the production of reagent grade PFOS and analytical standards.

Properties

The C8F17 subunit of PFOS is hydrophobic and lipophobic, like other fluorocarbons, while the sulfonic acid/sulfonate group adds polarity. PFOS is an exceptionally stable compound in industrial applications and in the environment because of the effect of aggregate carbon–fluorine bonds. PFOS is a fluorosurfactant that lowers the surface tension of water more than that of hydrocarbon surfactants. Although attention is typically focused on the straight-chain isomer (n-PFOS), which is dominant in commercial mixtures and environmental samples, there are 89 linear and branched congeners that are expected to have different physical, chemical, and toxicological properties.[16][17][18][19][20][21][22][23]

Uses

Perfluorooctanesulfonic acid is usually used as the sodium or potassium salts.

  • PFOS was the key ingredient in Scotchgard, a fabric protector made by 3M, and numerous stain repellents.
  • 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.
  • PFOS compounds can also be found in some impregnation agents for textiles, paper, and leather; in wax, polishes, paints, varnishes, and cleaning products for general use; in metal surfaces, and carpets.
  • In the semiconductor industry, PFOS is used in multiple photolithographic chemicals including: photoacid generators (PAGs) and anti-reflective coatings (ARCs). It has been phased out in the European Union semiconductor industry due to health concerns.
  • In Skydrol, a hydraulic fluid used in commercial aviation.

The most important emission sources of PFOS are metal plating and fire-fighting foams.[24]

Health effects in humans and wildlife

According to a 2002 study by the Environmental Directorate of the OECD "PFOS is persistent, bioaccumulative and toxic to mammalian species."[25]

In 2008, it was shown to affect the immune system of male mice at a blood serum concentration of 91.5 parts per billion, raising the possibility that highly exposed people and wildlife are immunocompromised.[26] Chicken eggs dosed at 1 milligram per kilogram (or 1000 parts per billion) of egg weight developed into juvenile chickens with an average of ~150 parts per billion in blood serum—and showed brain asymmetry and decreased immunoglobulin levels.[27] Occupationally exposed individuals may have an average level of PFOS over 1000 parts per billion, and a small segment of individuals in the upper range of the general population may be over the 91.5 parts per billion level.[26] A variety of wildlife species have had PFOS levels measured in egg, liver, kidney, serum, and plasma samples and some of the highest recorded values as of January 2006 are listed below.[28]

Species Geography Year Sample PFOS (ppb)
Bald eagleMidwestern United States1990–93plasma2,200
Brandt's cormorantCalifornia, USA1997liver970
GuillemotBaltic Sea1997egg614
Carrion crowTokyo Bay, Japan2000liver464
Red-throated loonNorth Carolina, USA1998liver861
Polar bearSanikiluaq, Nunavut2002liver3,100
Harbor sealDutch Wadden Sea, Denmark2002muscle2,725
Bottlenose dolphinCharleston, South Carolina, USA2003plasma1,315
Common dolphinMediterranean Sea, Italy1998liver940
MinkMichigan, USA2000–01liver59,500

The levels observed in wild animals are considered sufficient to "alter health parameters".[29][30] In people, the highest exposures to PFOS in blood have been 12,830 parts per billion for occupational exposure and 656 parts per billion[31]—or possibly 1,656 parts per billion[32]—in a consumer.

In animal studies PFOS can cause cancer, delays in physical development, stunted growth, endocrine disruption, and neonatal mortality; Neonatal mortality might be the most dramatic result of laboratory animal tests with PFOS.[33] Female mice with blood levels of PFOS at ranges found in wildlife and humans demonstrated higher mortality when infected with influenza A.[34] PFOS reduces the birth size of animals;[35] in humans, correlations between PFOS levels and reduced fetal growth are inconsistent.[36]

PFOS is detected in the blood serum of almost all people in the U.S., and concentrations have been decreasing over time. In contrast, PFOS blood levels appear to be rising in China.[37] PFOS levels in pregnant women have been associated with preeclampsia.[38] Increased levels have been associated with altered thyroid hormone levels in adults[39] and an increased risk of elevated cholesterol.[40][41] Levels in US children aged 12–15 were associated with an increased risk (60% over the interquartile range) of attention deficit hyperactivity disorder (ADHD).[42] One 2009 study found that women with higher levels of PFOS and PFOA took longer to become pregnant than those with lower levels, suggesting that the chemicals may impair fertility.[43]

PFOS has been detected in municipal wastewater[44] and drinking water samples,[45] worldwide, at concentrations ranging between few ng/L and some μg/L. In a recent study assessing the risk due to the presence of polyfluorinated alkyl substances (PFASs) in drinking water, Risk Quotients values higher than 0.2 or 1 were calculated for PFOS for some age groups under specific scenarios.[46] Further research is needed on the field as well as for the monitoring and prioritization of this compound in drinking water.

Precursors

Volatile sulfonamide PFOS precursors include N-methyl perfluorooctane sulfonamidoethanol (N-MeFOSE), a carpet stain repellent, and N-ethyl perfluorooctane sulfonamidoethanol (N-EtFOSE), a paper treatment.[47] Perfluorooctanesulfonamide is a precursor.[48] About 50 precursors were named in the 2004 proposed Canadian ban on PFOS.[49] Later, the OECD came up with a document containing a list of 20 pages with potential precursors to PFOS.[50]

Regulation

In May 2009, PFOS was included in Annex B of the Stockholm Convention on persistent organic pollutants by the Fourth Conference of Parties.[4] In 2008 Canada proposed a ban on PFOS, only the second chemical proposed for a complete ban under the Canadian Environmental Protection Act.[51]

Based on an OECD study on PFOS[25] and a risk assessment by Europe's Scientific Committee on Health and Environmental Risks[52] the European Union practically banned the use of PFOS in finished and semi-finished products in 2006 (maximum content of PFOS: 0.005% by weight).[53] However, PFOS use for industrial applications (e.g. photolithography, mist suppressants for hard chromium plating, hydraulic fluids for aviation) was exempted. In 2009 this directive was incorporated into the REACH regulation.[54] In the summer of 2010 PFOS was added to the regulation on persistent organic pollutants and the threshold was lowered to max. 0.001% by weight (10 mg/kg).[55]

Using information gained through a Freedom of Information Act request, in May 2018 it became public that January 2018 emails between the EPA, the White House, and the Department of Health and Human Services showed a discussion on PFOS. The emails showed a decision to withhold results of a study of PFOS done by the Agency for Toxic Substances and Disease Registry. That study was planned for publication. The study shows that PFOS endangers human health at a lower level. That lower level, the EPA previously determined was safe.[56]

See also

References
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