Perfluorooctanesulfonic acid

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Structural formula
Structure of perfluorooctanesulfonic acid
General
Surname Perfluorooctanesulfonic acid
other names
  • PFOS
  • Perfluorooctanesulfonic acid
  • Heptadecafluorooctane-1-sulfonic acid
Molecular formula
  • C 8 HF 17 O 3 S (acid)
  • C 8 F 17 O 3 S - (anion)
External identifiers / databases
CAS number
  • 1763-23-1 (acid)
  • 45298-90-6 (anion)
EC number 217-179-8
ECHA InfoCard 100.015.618
PubChem 74483
Wikidata Q902094
properties
Molar mass
  • 500.13 g mol −1 (acid)
  • 499.12 g mol −1 (anion)
Physical state

firmly

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 05 - Corrosive 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 302 + 332-314-351-360D-362-372-411
P: 201-263-273-281-308 + 313
MAK

Switzerland: 0.01 mg m −3 (measured as inhalable dust )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Perfluorooctanesulfonic acid (anion perfluorooctanesulfonate or PFOS for short ) is a chemical compound from the group of perfluorinated and polyfluorinated alkyl compounds (PFAS). Usually it is or has been offered commercially as the potassium, lithium, ammonium, diethanolammonium or tetraethylammonium salt. In 2009, PFOS was included as a pollutant in Appendix B of the Stockholm Convention .

history

In 1953, Patsy O'Connell Sherman (1930–2008) accidentally discovered the cleaning effect of a fluoropolymer at 3M . Together with Samuel Smith (1927-2005), perfluorooctanesulfonate was brought to product maturity by 1956.

Extraction and presentation

This article or the following section is not adequately provided with supporting documents ( e.g. individual evidence ). Information without sufficient evidence could be removed soon. Please help Wikipedia by researching the information and including good evidence.

PFOS can be produced by micro-polymerization of tetrafluoroethylene . The reaction is controlled in such a way that chains with six carbon atoms are formed. An ethylene molecule is added to this intermediate product and then converted to the sulfonate .

properties

The specialty of PFOS is that the perfluorinated group is non-polar, whereas the polar anionic group is hydrophilic . It is therefore a surfactant .

Dome model of the perfluorooctane sulfonate. On the left the non-polar perfluorinated chain; on the right the negatively charged, polar sulfonate group.

PFOS is environmentally persistent, bioaccumulative and toxic to mammals. For this reason, all German chemical companies stopped producing PFOS worldwide in 2002 and reformulated many products to use the shorter-chain perfluorobutane sulfonic acid (PFBS).

use

PFOS was mainly used to impregnate materials such as textiles, carpets and paper in a grease, oil and water-proof manner (3M Scotchgard ). In addition, it was and is used in chrome plating , in analog photography , in older fire-fighting foams ( AFFF ) and in hydraulic fluids for the aerospace industry.

PFOS continues to be emitted into the environment. The main sources are metal processing (chrome plating) and fire-fighting foams.

proof

The reliable qualitative and quantitative detection of PFOS in different test materials succeeds after adequate sample preparation by coupling the HPLC with the mass spectrometry .

Limit values

In December 2018, EFSA reduced the tolerable weekly intake (TWI) to 13 ng per kg body weight and week. It has been found that exposure of a significant proportion of the population is higher than this value.

According to the Water Framework Directive , the annual average environmental quality standards are 0.65 ng · l −1 for inland surface water and 0.13 ng · l −1 for other surface water. The environmental quality standard for biota (fish) is 9.1 μg kg −1 wet weight.

Occurrence in the environment

In summer 2006, high PFOS values ​​were measured in the Rhine and the Ruhr . Sewage sludge from Belgium that was incorrectly declared brought the substances to Germany. Investigations revealed that farmers were being paid to spread the contaminated sewage sludge on their fields. From there, components found their way into groundwater and river water.

2012 were originally in the lake Stoiber mill north of Munich airport and in Lindacher See the north airfield Ingolstadt / Manching detected elevated levels of various perfluorinated surfactants, including PFOS (1 ug / l, limit: 0.3 g / l).

In 2015, increased levels of various perfluorinated surfactants (3 µg / l), including PFOS, were detected in the Birkensee bathing lake east of Nuremberg . A bathing ban was temporarily issued.

In 2019, the authorities warned against frequent consumption of fish from the Moosach .

The US Department of Defense announced in November 2019 that it had identified other locations that have been contaminated with PFOS or PFOA via the 401 previously named.

In April 2020, the Lower Saxony Ministry of Consumer Protection advised against the regular consumption of Lower Saxony river fish in a consumption recommendation. When fish samples were examined, the median PFOS concentrations in the muscle tissue of the fish was 7.8 μg / kg.

Prohibition

The European Parliament decided in October 2006 to restrict the use of PFOS to a few areas of application. The "Directive 2006/122 / EC of the European Parliament and of the Council" came into force on December 27, 2006 through publication in the Official Journal of the European Union (2006 / L 372).

At the 4th Conference of the Parties to the Stockholm Convention (Geneva, May 4-8, 2009) it was decided to include PFOS in Appendix B of the substances restricted under this Convention.

See also

Individual evidence

  1. ↑ a b entry to perfluorooctane sulfonic acid in the GESTIS Bank of IFA , accessed on February 1, 2016(JavaScript required) .
  2. ↑ Entry on perfluorooctane sulfonic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 9, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
  3. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values , accessed on November 2, 2015.
  4. ↑ External identifiers or database links for potassium perfluorooctanesulfonate: CAS number: 2795-39-3, EC number: 220-527-1, ECHA InfoCard: 100.018.661 , GESTIS substance database : 113462 , PubChem : 23669238 , ChemSpider : 68535 , Wikidata : Q27276914 .
  5. ↑ External identifiers of or database links to lithium perfluorooctane sulfonate: CAS number: 29457-72-5, EC number: 249-644-6, ECHA InfoCard: 100.045.117 , GESTIS substance database : 137396 , PubChem : 23677927 , ChemSpider : 118370 , Wikidata : Q27251563 .
  6. ↑ External identifiers or database links for ammonium perfluorooctane sulfonate: CAS number: 29081-56-9, EC number: 249-415-0, ECHA InfoCard: 100.044.908 , GESTIS substance database : 137199 , PubChem : 15607692 , ChemSpider : 107238 , Wikidata : Q72443080 .
  7. ↑ External identifiers of or database links to diethanolammonium perfluorooctanesulfonate: CAS number: 70225-14-8, EC number: 274-460-8, ECHA InfoCard: 100.067.670 , GESTIS substance database : 159177 , PubChem : 112394 , ChemSpider : 100740 , Wikidata : Q81985372 .
  8. ↑ External identifiers or database links for tetraethylammonium perfluorooctane sulfonate: CAS number: 56773-42-3, EC number: 260-375-3, ECHA InfoCard: 100.054.869 , GESTIS substance database : 146734 , PubChem : 92531 , ChemSpider : 83538 , Wikidata : Q72481197 .
  9. ↑ Press Release - COP4 - Geneva, 8 May 2009: Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty
  10. ^ Fascinating facts about the invention of Scotchgard ™ by Patsy Sherman and Sam Smith in 1956.
  11. ↑ Patent US2732398 : Fluorocarbon sulfonic acids and derivatives. Applied on August 9, 1954 , published January 24, 1956 , Applicant: Minnesota Mining & Manufacturing, Inventor: Thomas J. Brice, Paul W. Trott (citation: "The n-perfluorooctane compounds, which have a normal chain of eight perfluorinated carbon atoms, CF 3 (CF 2 ) 7 - , are of particular noteworthy value as surface active agents and as starting compounds for making surface active compounds. "). ‌
  12. ↑ Press release of the VCI of October 6, 2005: Data and facts on the substance list of the WWF blood test (PDF; 33 kB)
  13. ↑ Substance flow analysis for Switzerland - Perfluorinated surfactants perfluorooctanesulfonate (PFOS) and perfluorooctanoic acid (PFOA). Federal Office for the Environment, 2009.
  14. ↑ F. Pérez, M. Llorca, M. Köck-Schulmeyer, B. Skrbić, LS Oliveira, K. da Boit Martinello, NA Al-Dhabi, I. Antić, M. Farré, D. Barceló: Assessment of perfluoroalkyl substances in food items at global scale. In: Environ Res. 135C, 1 Oct 2014, pp. 181-189. PMID 25282275
  15. ↑ Z. Lu, L. Song, Z. Zhao, Y. Ma, J. Wang, H. Yang, H. Ma, M. Cai, G. Codling, R. Ebinghaus, Z. Xie, JP Giesy: Occurrence and trends in concentrations of perfluoroalkyl substances (PFASs) in surface waters of eastern China. In: Chemosphere. 119C, Sep 11, 2014, pp. 820-827. PMID 25218980
  16. ↑ EFSA Panel on Contaminants in the Food Chain (CONTAM), Helle Katrine Knutsen, Jan Alexander, Lars Barregård et al .: Risk to human health related to the presence of perfluorooctane sulfonic acid and perfluorooctanoic acid in food . In: EFSA Journal . tape 16 , no. December 12 , 2018, doi : 10.2903 / j.efsa.2018.5194 .
  17. ↑ https://eur-lex.europa.eu/legal-content/DE/TXT/?uri=CELEX:32013L0039
  18. ^ Case of environmental crime - drinking water contaminated with the chemical PFT ( Memento from November 28, 2006 in the Internet Archive ). In: WDR . 2006.
  19. ↑ ES&T Science News: Perfluorinated surfactants contaminate German waters. 2006. doi: 10.1021 / es062811u .
  20. ↑ Is fire fighting foam from the airport the reason? Chemical alarm in the Stoibermühlsee. tz, July 25, 2012
  21. ↑ PFT in Birkensee: bathing ban remains in place. ( Memento of November 29, 2015 in the Internet Archive ) BR, August 28, 2015
  22. ↑ Birgit Grundner, Rüdiger Kronthaler: PFOS-contaminated fish in the Moosach: Warning against consumption. In: br.de . August 8, 2019, accessed September 23, 2019 .
  23. ^ The list of military sites with suspected 'forever chemicals' contamination has grown
  24. ↑ Update of the consumption recommendation for fish | Nds. Ministry of Food, Agriculture and Consumer Protection. Retrieved April 18, 2020 .
  25. ↑ Official Journal of the European Union: DIRECTIVE 2006/122 / EC OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of December 12, 2006 on the thirtieth amendment to Directive 76/769 / EEC of the Council on the approximation of the laws and regulations of the member states on marketing restrictions and Use of certain dangerous substances and preparations (perfluorooctane sulfonates) (PDF) . December 27, 2006 / L 372.
  26. ↑ Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty , press release, May 8, 2009.

Web links