Perfluorooctanesulfonyl fluoride

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Perfluorooctanesulfonyl fluoride
POSF molecule
Names
Preferred IUPAC name
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluorooctane-1-sulfonyl fluoride
Identifiers
3D model (
JSmol
)
Abbreviations POSF, PFOSF
ChemSpider
ECHA InfoCard
 100.005.638 Edit this at Wikidata
EC Number
  • 206-200-6
UNII
  • InChI=1S/C8F18O2S/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)29(26,27)28 ☒N
    Key: BHFJBHMTEDLICO-UHFFFAOYSA-N ☒N
  • InChI=1/C8F18O2S/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)29(26,27)28
    Key: BHFJBHMTEDLICO-UHFFFAOYAY
  • C(C(C(C(C(F)(F)S(=O)(=O)F)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)(F)F
Properties
C8F18O2S
Molar mass 502.12 g/mol
Boiling point 154 °C (309 °F; 427 K)[1]
Related compounds
Related compounds
 Perfluorooctanesulfonic acid (PFOS), Perfluorooctanesulfonamide (PFOSA), Perfluorooctanoic acid (PFOA), Perfluorobutanesulfonic acid (PFBS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Perfluorooctanesulfonyl fluoride (POSF) is a synthetic

perfluorinated compound with a sulfonyl fluoride functional group. It is used to make perfluorooctanesulfonic acid
(PFOS) and PFOS-based compounds. These compounds have a variety of industrial and consumer uses, but POSF-derived substances ultimately degrade to form PFOS.

Because of environmental concerns over PFOS, 3M ceased POSF use in 2002 and global production plummeted. However, Chinese production grew after 3M's phaseout. As of May 2009, POSF and PFOS are listed as persistent organic pollutants (POPs) included in Annex B of the Stockholm Convention.

Synthesis

POSF is synthesized by electrochemical fluorination of octanesulfonyl fluoride in anhydrous hydrogen fluoride by the equation:[2]

C8H17SO2F + 17 F− → C8F17SO2F + 17 H+ + 34 e−.

This

isomers, with ~70% linear.[2] POSF can also be obtained by ECF of the sulfonyl halide octanesulfonyl chloride.[2]

Production

In 1949, 3M began producing POSF by

better source needed] Before 2000, 3M was the largest global producer of POSF (mainly at their Decatur, AL and Antwerp facilities) and global production peaked at ~4500 tonnes per year.[3]

In 1999, the

perfluorinated compounds after receiving data on the global distribution and toxicity of PFOS, the key ingredient in Scotchgard.[5] For these reasons, and USEPA pressure,[6] the primary American producer of PFOS, 3M, announced, in May 2000, the phaseout of the production of PFOS, PFOA, and PFOS-related products.[7] 3M stated that they would have made the same decision regardless of USEPA pressure.[8]

Immediately after the 2000–2002 3M phaseout, production plummeted, but dominant and growing production shifted to China.[9] In 2004 Chinese production of PFOS-based compounds was estimated to be <50 tonnes.[9] In 2005 global production was estimated to be between 73 and 162 tonnes,[10] and by 2006 Chinese production was estimated at >200 tonnes.[9] Total historical global production was estimated at ~120,000 tonnes in 2009.[3]

Most, if not all industrially synthesized perfluorooctanesulfonyl derivatives, such as PFOS, have POSF as their precursor.[2]

Reactivity

POSF and POSF-based polymers degrade to form PFOS[11] which is not known to degrade by any environmental processes.[6] POSF hydrolysis in water, however, occurs slowly.[2]

POSF reacts with bases such as potassium hydroxide to form PFOS salts:[2]

C8F17SO2F + KOH → C8F17O2SO3−K+ + HF.

Upon treatment with sulfuric acid the sulfonic acid PFOS tetrahydrate is obtained.[2]

POSF also reacts with ammonia to form perfluorooctanesulfonamide:[2]

C8F17SO2F + NH3 → C8F17O2SNH2.

Sulfonamides and sulfonamidoethanols synthesized from POSF can in turn react to form a variety of different functional groups for different applications and products.[12]

Uses

Because of multiple

fluorosurfactants).[4] The main uses of chemical substances derived from POSF have been:[3]

The Stockholm Convention lists a variety of acceptable purposes and specific exemptions for POSF and PFOS (and it salts) including

International status

At the Fourth Conference of Parties, decision SC-4/17 put POSF, along with PFOS, in the Stockholm Convention on Persistent Organic Pollutants (Annex B) in May 2009.[14][15] As such, POSF is not "banned" but has approved uses and exemptions—along with a program (SC-4/19) in Annex B that encourages reduced production.[16][17]

Environmental concern

The POSF degradation product, PFOS, is the dominant perfluorinated compound detected in

biomonitoring studies,[18] where concentrations that have been detected are considered sufficient to "alter health parameters".[19][20]

See also

  • Organofluorine compounds

References

  1. ^ "Perfluoro-1-octanesulfonyl fluoride". National Institute of Standards and Technology. 1990. p. 1. Retrieved 10 July 2009.
  2. ^
    PMID 15694468
    .
  3. ^
    PMID 19238969
    .
  4. ^ a b (1999) 3M. 1999. The science of organic fluorochemistry. 3M Company, February 5, 1999. (PDF readily accessible via a Google search for the article title.)
  5. ^ Aziz Ullah. "The Fluorochemical Dilemma: What the PFOS/PFOA fuss is all about" Cleaning & Restoration. www.ascr.org, (October, 2006). Accessed October 25, 2008.
  6. ^ a b Lee, Jennifer 8. (15 April 2003). "E.P.A. Orders Companies to Examine Effects of Chemicals". The New York Times. Retrieved 15 May 2009.{{cite news}}: CS1 maint: numeric names: authors list (link)
  7. ^ 3M: "PFOS-PFOA Information: What is 3M Doing?" Archived 2008-09-22 at the Wayback Machine Accessed October 25, 2008.
  8. Business Week
    (3684): 96.
  9. ^
    PMID 19708337
    .
  10. Organisation for Economic Co-operation and Development
    . p. 10. Retrieved 30 August 2009.
  11. PMID 11999053
    .
  12. Organisation for Economic Co-operation and Development
    . 21 November 2002. p. 14.
  13. ^ "Report of the Conference of the Parties of the Stockholm Convention on Persistent Organic Pollutants on the work of its fourth meeting" (PDF). p. 67.
  14. ^ "Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty". Geneva: Stockholm Convention Secretariat. 8 May 2008.
  15. ^ "Report of the Conference of the Parties of the Stockholm Convention on Persistent Organic Pollutants on the work of its fourth meeting" (PDF). Geneva. 8 May 2009. p. 66.
  16. ^ "Report of the Conference of the Parties of the Stockholm Convention on Persistent Organic Pollutants on the work of its fourth meeting" (PDF). pp. 67–69.
  17. ^ "U.N. treaty expanded by 9 more chemicals: Participating nations get one year to decide on next steps". NBC News. Associated Press. 11 May 2009. Retrieved 5 September 2009.
  18. PMID 16786681. Supporting Information
    (PDF).
  19. doi:10.1016/j.reprotox.2008.11.016
    .
  20. ^ Peden-Adams et al. (June 2008). In PFAA Days II Archived 2011-07-26 at the Wayback Machine (PDF). p. 28.

External links

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