Perfluorooctanesulfonamide

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Structural formula
Structural formula of perfluorooctanesulfonamide
General
Surname Perfluorooctanesulfonamide
other names
  • 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-1-octanesulfoamide
  • PFOSA
  • Perfluorooctyl sulfonamide
Molecular formula C 8 H 2 F 17 NO 2 S
Brief description

white solid

External identifiers / databases
CAS number 754-91-6
EC number 212-046-0
ECHA InfoCard 100.010.951
PubChem 69785
Wikidata Q7168162
properties
Molar mass 499.14 g mol −1
Physical state

firmly

Melting point

145-150 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 280-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Perfluorooctanesulfonamide ( PFOSA ) is a chemical compound that belongs to the perfluorinated and polyfluorinated alkyl compounds (PFAS).

In the environment, PFOSA can be converted to perfluorooctane sulfonate (PFOS).

presentation

PFOSA can be prepared by the reaction of perfluorooctanesulfonic acid halides with liquid ammonia or by a two-step reaction via azide , followed by a reduction by Zn / HCl .

use

N- alkyl-substituted perfluorooctanesulfonamides are used in photographic papers, in medical applications and in pesticides . PFOSA accumulates through the food chain ( bioaccumulation ). It is believed that PFOSA is the biologically active form of the insecticide sulfluramide ( N -ethyl perfluorooctanesulfomamide).

regulation

Since perfluorooctanesulfonamide falls under the definition “ Perfluorooctanesulfonic acid and its derivatives (PFOS) C 8 F 17 SO 2 X (X = OH, metal salts (O – M + ), halides , amides and other derivatives including polymers )”, it is subject to the EU and a far-reaching ban in Switzerland.

Individual evidence

  1. ↑ a b c d JK-Scientific: Perfluorooctanesulfonamide (PDF; 132 kB), accessed on December 27, 2019.
  2. ^ A b HJ Lehmler: Synthesis of environmentally relevant fluorinated surfactants — a review . In: Chemosphere . 58, No. 11, 2005, pp. 1471-1496. doi : 10.1016 / j.chemosphere.2004.11.078 . PMID 15694468 .
  3. ↑ Lehmler HJ, Rama Rao VV, Nauduri D, Vargo JD, Parkin S: Synthesis and Structure of Environmentally Relevant Perfluorinated Sulfonamides . In: J Fluor Chem . 128, No. 6, 2007, pp. 595-607. doi : 10.1016 / j.jfluchem.2007.01.013 . PMID 18516235 . PMC 2394736 (free full text).
  4. ↑ Patent application EP0021003B1 : Use of perfluoroalkanesulfonamide salts as surfactants. Registered on May 14, 1980 , published on February 9, 1983 , applicant: Bayer AG , inventor: Karl-Heinz Mitschke, Hans Niederprüm. ‌
  5. ↑ UBA Text 41/2007: Development and validation of a method for the determination of polyfluorinated organic substances in sea water, sediments and biota; Investigations into the occurrence of these pollutants in the North and Baltic Seas (PDF; 6.4 MB).
  6. ↑ AA Starkov KB Wallace: Structural determinants of fluorochemical-induced mitochondrial dysfunction . In: Toxicol. Sci. . 66, No. 2, 2002, pp. 244-252. doi : 10.1093 / toxsci / 66.2.244 . PMID 11896291 .
  7. ↑ Regulation (EU) 2019/1021 of the European Parliament and of the Council of June 20, 2019 on persistent organic pollutants (new version)
  8. ↑ Chemical Risk Reduction Ordinance , Appendix 1.16