Perfluorooctanesulfonyl fluoride

Structural formula
General
Surname	Perfluorooctanesulfonyl fluoride
other names	Heptadecafluorooctanesulfonyl fluoride POSF PFOSF
Molecular formula	C 8 F 18 O 2 S
Brief description	colorless liquid
External identifiers / databases
CAS number 307-35-7 EC number 206-200-6 ECHA InfoCard 100.005.638 PubChem 9388 ChemSpider 9019 Wikidata Q7168165
properties
Molar mass	502.12 g mol −1
Physical state	liquid
density	1.824 g cm −3 (25 ° C)
Melting point	−15.39 ° C
boiling point	154-155 ° C
Vapor pressure	<13 hPa (20 ° C)
Refractive index	1.301 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 314 P: 280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Perfluorooctanesulfonyl fluoride (POSF or PFOSF) is a synthetic chemical compound that belongs to the perfluorinated and polyfluorinated alkyl compounds (PFAS). It is used to make perfluorooctanesulfonic acid (PFOS) and PFOS-based compounds.

history

In 1949, 3M began producing POSF using electrochemical fluorination . From 1966 through the 1990s, 3M's production increased in line with the increased demand for POSF-based connections. Prior to 2000, 3M was the world's largest producer of POSF (mainly at its Decatur , Alabama and Antwerp plants ) and global production peaked at 4,500 tons per year. 3M stopped manufacturing and using POSF in 2002, and global production declined. Chinese production, however, grew.

At the 4th Conference of the Parties to the Stockholm Convention in May 2009 it was decided to include POSF together with PFOS and its salts in Appendix B of the substances restricted under this Convention.

Extraction and presentation

POSF is made by electrochemical fluorination of octanesulfonyl fluoride in anhydrous hydrogen fluoride :

${\displaystyle {\ce {C8H17SO2F + 17 F- -> C8F17SO2F + 17 H+ + 34 e-}}}$

This reaction leads to a 25% yield. The product obtained is impure; it is a mixture of linear (~ 70%) and branched (~ 30%) isomers . POSF can also be obtained by electrochemical fluorination of octanesulfonyl chloride .

use

POSF is used as an intermediate in the production of monomers and surfactants for textile treatment, paper chemicals and inert liquids. It is also the starting material in the production of sulfluramide .

Individual evidence

1. ↑ ^{a b c d e f g h i} data sheet Perfluoro-1-octanesulfonyl fluoride, 95% (sum of isomers) from Sigma-Aldrich , accessed on May 10, 2017 ( PDF ).
2. ^ ^{A b c} Paul AG, Jones KC, Sweetman AJ: A first global production, emission, and environmental inventory for perfluorooctane sulfonate . In: Environ. Sci. Technol. . 43, No. 2, 2009, pp. 386-392. doi : 10.1021 / es802216n . PMID 19238969 .
3. ↑ Wang T, Wang Y, Liao C, Cai Y, Jiang G: Perspectives on the Inclusion of Perfluorooctane Sulfonate into the Stockholm Convention on Persistent Organic Pollutants . In: Environ. Sci. Technol. . 43, No. 14, 2009, pp. 5171-5175. doi : 10.1021 / es900464a . PMID 19708337 .
4. ↑ Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty , press release, May 8, 2009.
5. ^ ^{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 .
6. ^ GWA Milne: Gardner's Commercially Important Chemicals Synonyms, Trade Names, and Properties . John Wiley & Sons, 2005, ISBN 0-471-73661-9 , p. 480.
7. ↑ John Löfstedt Gilljam, Juliana Leonel, Ian T. Cousins, Jonathan P. Benskin: Is Ongoing Sulfluramid Use in South America a Significant Source of Perfluorooctanesulfonate (PFOS)? Production Inventories, Environmental Fate, and Local Occurrence. In: Environ. Sci. Technol. 50, 2016, pp. 653-659, doi: 10.1021 / acs.est.5b04544 .