Perfluorooctanoic acid

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Structural formula
Structural formula of perfluorooctanoic acid
General
Surname Perfluorooctanoic acid
other names
  • PFOA
  • Pentadecafluorooctanoic acid
Molecular formula C 8 HF 15 O 2
Brief description

white solid with a pungent odor

External identifiers / databases
CAS number 335-67-1
EC number 206-397-9
ECHA InfoCard 100.005.817
PubChem 9554
Wikidata Q418348
properties
Molar mass 414.07 g mol −1
Physical state

firmly

density

1.8 g cm −3 

Melting point

54.3 ° C 

boiling point

192.4 ° C 

Vapor pressure

0.69 hPa (20 ° C)

solubility

poor in water (3.4 g l −1 at 20 ° C)

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

danger

H and P phrases H: 302 + 332-318-351-360D-362-372
P: 201-260-263-280-305 + 351 + 338 + 310-308 + 313
Authorization procedure under REACH

of particular concern : toxic for reproduction ( CMR ), persistent, bioaccumulative and toxic ( PBT )

MAK

5 µg m −3 ( inhalable dust ) 

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

Perfluorooctanoic acid ( abbreviation PFOA ) is a perfluorocarboxylic acid , i. H. a completely fluorinated carboxylic acid , which belongs to the per- and polyfluorinated alkyl compounds (PFAS). It has oil and water repellent (amphiphobic) properties and thus acts as a surfactant .

properties

The high stability and resistance of perfluorooctanoic acid under the most varied of conditions make it suitable for various applications. Perfluorooctanoic acid is now a widespread substance in the environment because it is both persistent and bioaccumulative .

use

Perfluorooctanoic acid (in the form of ammonium perfluorooctanoate (APFO)) was mainly used as an aid ( emulsifier ) for the production of polymers such as polytetrafluoroethylene (at Chemours : Teflon). The substitutes ADONA ( Dyneon ) or the ammonium salt of HFPO-DA / GenX (Chemours) are now used in these processes .

Exposure

PFOA can be released into the environment or the human body as a contaminant or degradation product of fluorochemicals. The most important sources of emissions include dirt and water-repellent carpets and textiles as well as fire-fighting foam ( AFFF ).

In the drinking water in the Rhein-Ruhr -region concentrations were detected up to 500 ng / l. This pollution was caused by contaminated manure applied to agricultural fields .

In November 2006, Greenpeace detected concentrations of PFOA in the Alz below the Gendorf industrial park in the municipality of Burgkirchen ad Alz. They are said to exceed those in the Rhine by 10,000 times. Clariant and Dyneon work with fluorochemicals in the industrial park . At that time, the industrial park Werk Gendorf had a permit to introduce 1000 μg / l perfluorinated surfactants into the Alz.

A comparable problem is the contamination of drinking water in Mittelbaden (region between Baden-Baden and Rastatt) with perfluorinated and polyfluorinated chemicals . Here, too, the contamination of arable land with compost containing PFAS was identified as a source. The previously used solution of cleaning drinking water using activated carbon filters is complex and expensive.

Hazard and risk assessment

In addition to its longevity and its ability to accumulate in organisms, perfluorooctanoic acid is hardly excreted from the human body. Studies (tests on rodents and epidemiological studies on factory workers) have indicated properties that are harmful to the liver , toxic to reproduction and carcinogenic .

In February 2006, the US Environmental Protection Agency (EPA) signed a voluntary agreement with the major fluoropolymer manufacturers to eliminate PFOA emissions from manufacturing and product contamination by 2015. It was stated that this was a precautionary measure without any general risk to humans or the environment and that there was no cause for concern with regard to consumer products. In numerous cases, the manufacturer DuPont was sentenced to compensation for damage to health caused by PFOA; the environmental attorney Robert Bilott , who the plaintiffs z. In some cases she had represented in class actions and initiated extensive investigations, was awarded the Right Livelihood Award (Alternative Nobel Prize) in 2017 .

The German Federal Institute for Risk Assessment has also classified health risks for humans as unlikely due to the usual concentrations in food. In connection with the fish caught in the Alz, the Bavarian State Office for Health and Food Safety published a toxicological assessment in 2008. The European Food Safety Authority reduced the tolerable weekly intake (TWI) to 6 ng per kg body weight and week in December 2018. It has been found that exposure of a significant proportion of the population is higher than this value. In the case of fish from the Ochtum , consumption is not recommended due to the high pollution.

The Royal Institute voor Volksgezondheid en Milieu suggested based on the Water Framework Directive as annual average EQS a value of 48 ng · L -1 before. For the maximum permissible concentration values ​​of 2800 ng · l −1 (fresh water) and 560 ng · l −1 (salt water) were suggested.

The Federal Institute for Risk Assessment (BfR) is concerned with the question of whether the use of fluorotelomer alcohols (FTOH) can lead to contamination with PFOA. FTOH are used for the production of water- and fat-repellent coatings that are used in food packaging (e.g. baking paper , pizza boxes, popcorn packaging), but also for carpets and car seats . Apparently, PFOA can migrate from these packages into food as a contaminant or degradation product. According to the BfR, perfluorooctanoic acid should not be tolerated in food in the long term.

In 2013, the Risk Assessment Committee (RAC) classified it as category 1B toxic to reproduction, which became legally binding with the 5th ATP . Based on this, perfluorooctanoic acid was also included in the candidate list of substances of very high concern under REACH in 2013 . In June 2017 the EU Commission concluded a restriction procedure against PFOA and precursor substances. Accordingly, since July 4, 2020, PFOA may no longer be manufactured and placed on the market. In mixtures, the upper limit for PFOA is 25 ppb and for PFOA precursors is 1000 ppb. There are exemptions for occupational safety textiles and fire extinguishing foam.

PFOA was nominated for inclusion in the Stockholm Convention in 2015 and included in Appendix A (elimination) in May 2019. As a result, the regulations in the EU were moved from Annex XVII of the REACH regulation to the EU POP regulation and adapted.

Individual evidence

  1. ↑ a b c d e f g h i Entry on perfluorooctanoic acid in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  2. ↑ Entry on Pentadecafluorooctanoic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers and / or distributors can expand the harmonized classification and labeling .
  3. ↑ Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.
  4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 335-67-1 or perfluorooctanoic acid ), accessed on November 2, 2015.
  5. ↑ Gloria B. Post, Perry D. Cohn, Keith R. Cooper: Perfluorooctanoic acid (PFOA), an emerging drinking water contaminant: A critical review of recent literature . Environmental Research 2012, 116, 93-117; doi: 10.1016 / j.envres.2012.03.007 .
  6. ↑ External identifiers or database links for ammonium perfluorooctanoate: CAS number: 3825-26-1, EC number: 223-320-4, ECHA InfoCard: 100.021.202 , GESTIS substance database : 115708 , PubChem : 62525 , ChemSpider : 56299 , Wikidata : Q26841285 .
  7. ↑ Office of Research & Development: Identification and occurrence of novel cyclic and polymeric perfluoroalkyl ethers (PFECAs) downstream of the fluoropolymer manufacturing plants. Retrieved July 22, 2020 (English).
  8. ↑ Steven C. Gordon: Toxicological evaluation of ammonium 4,8-dioxa-3H-perfluorononanoate, a new emulsifier to replace ammonium perfluorooctanoate in fluoropolymer manufacturing . In: Regulatory Toxicology and Pharmacology . tape 59 , no. 1 , February 2011, p. 64-80 , doi : 10.1016 / j.yrtph.2010.09.008 .
  9. ↑ Rijksinstituut voor Volksgezondheid en Milieu : Evaluation of substances used in the GenX technology by Chemours, Dordrecht , 2016 ( PDF ).
  10. ↑ Swiss Federal Office for the Environment (2009): Substance flow analysis for Switzerland -Perfluorinated surfactants perfluorooctanesulfonate (PFOS) and perfluorooctanoic acid (PFOA) , 2009.
  11. ↑ ES&T Science News (2006): Perfluorinated surfactants contaminate German waters , doi: 10.1021 / es062811u .
  12. ^ WDR: Case of environmental crime - drinking water contaminated with the chemical PFT ( Memento from November 28, 2006 in the Internet Archive ) .
  13. ↑ Bavarian river poisoned with chemicals - carcinogenic industrial chemicals in the Alz and Gendorfer drinking water . Greenpeace press release of November 9, 2006.
  14. ↑ Bavaria SPD - Working Group on Environmental Issues and Health: Chemicals in the Alz: Environmental scandal tolerated by the authorities?
  15. ↑ News. Retrieved October 29, 2017 .
  16. ^ Frankfurter Allgemeine Zeitung GmbH: Environmental scandal: where did that stuff come from? September 4, 2016. Retrieved October 29, 2017 .
  17. ↑ PFC scandal in Mittelbaden: question of guilt remains unresolved | Karlsruhe | SWR news . In: swr.online . ( swr.de [accessed October 29, 2017]).
  18. ^ Frankfurter Allgemeine Zeitung GmbH: Contaminated groundwater: Who is to blame? February 13, 2017. Retrieved October 29, 2017 .
  19. ^ The first: The broadcast of October 29, 2016 - W for knowledge. October 29, 2016. Retrieved October 29, 2017 .
  20. ↑ a b c d BfR: Health risks from PFOS and PFOA in food are unlikely according to the current state of scientific knowledge. (PDF; 383 kB) BfR opinion 004/2009 of September 11, 2008.
  21. ↑ Robert Bilott (USA) | The Right Livelihood Award. Retrieved September 26, 2017 (American English).
  22. ↑ LfU: Toxicological assessment of PFOA and PFOS in fish from the Alz ( Memento from December 2, 2013 in the Internet Archive )
  23. ↑ 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 .
  24. ↑ Final report on the examination of fish in Lower Saxony's Ochtum for perfluorinated alkyl substances (PFAS) in 2019. (PDF; 1 MB) In: laves.niedersachsen.de . 2019, accessed December 19, 2019 .
  25. ↑ EMJ Verbruggen, PNH Wassenaar, CE Smit: Water quality standards for PFOA - A proposal in accordance with the methodology of the Water Framework Directive , RIVM Letter report 2017-0044, doi: 10.21945 / RIVM-2017-0044 .
  26. ^ The Teflon Toxin - DuPont and the Chemistry of Deception
  27. ↑ BfR opinion of October 27, 2005: Perfluorochemicals in papers and cardboard boxes for food packaging (PDF; 52 kB) .
  28. ↑ Umweltmagazin.de: REACH: EU confirms particularly worrying properties for chemicals in outdoor clothing from June 24, 2013.
  29. ↑ Regulation (EU) 2017/1000 of the Commission of 13 June 2017 amending Annex XVII of Regulation (EC) No. 1907/2006 of the European Parliament and of the Council on the Registration, Evaluation, Authorization and Restriction of Chemicals (REACH) Perfluorooctanoic acid (PFOA), its salts and PFOA precursor compounds . In: Official Journal of the European Union . L 150, June 14, 2017, page 14ff.
  30. ↑ Proposal to list pentadecafluorooctanoic acid (CAS No: 335-67-1, PFOA, perfluorooctanoic acid), its salts and PFOA-related compounds in Annexes A, B and / or C to the Stockholm Convention on Persistent Organic Pollutants . UNEP / POPS / POPRC.11 / 5. 2015 (English, pops.int ).
  31. ↑ 2019 Meetings of the Conferences of the Parties to the Basel, Rotterdam and Stockholm Conventions
  32. ↑ Regulation (EU) 2020/784 of the Commission of April 8, 2020 amending Annex I of Regulation (EU) 2019/1021 of the European Parliament and of the Council with regard to the inclusion of perfluorooctanoic acid (PFOA), its salts and PFOA precursor compounds

literature

Web links