Surflon S-111

Image:Perfluorononanoic acid.svg, the predominant compound present in Surflon S-111]]

Surflon S-111 (CAS 72968-3-88) is a commercial product consisting of perfluorinated carboxylic acids (PFCAs) in ammonium salt form. It is commonly used as a polymerization aid in the production of fluoropolymers.{{cite conference

|title = PFOA in Norway TA-2354/2007

|pages = 74–75

|publisher = Norwegian Pollution Control Authority

|date = 2007

|url = http://www.sft.no/publikasjoner/2354/ta2354.pdf

|accessdate = 2009-04-06

}}{{Dead link|date=June 2018 |bot=InternetArchiveBot |fix-attempted=no }}

The dominant chemical compound is perfluorononanoic acid (PFNA) at 74% by weight, followed by the 11 carbon perfluoroundecanoic acid (20%), and the 13 carbon perfluorotridecanoic acid (5%).{{cite journal

|vauthors=Prevedouros K, Cousins IT, Buck RC, Korzeniowski SH

|title=Sources, fate and transport of perfluorocarboxylates

|journal=Environ Sci Technol

|volume=40 |issue=1 |pages=32–44 |date=January 2006

|doi=10.1021/es0512475 |pmid=16433330}} [http://pubs.acs.org/doi/suppl/10.1021/es0512475/suppl_file/es0512475.pdf Supporting Information] (PDF).

Surflon S-111 is synthesized in Japan by oxidizing a mixture of fluorotelomer olefins. Fluorotelomer olefins are synthesized using a telomerization of tetrafluoroethylene taxogens (monomers),{{cite journal

|last=Lehmler |first=HJ

|title=Synthesis of environmentally relevant fluorinated surfactants—a review

|journal=Chemosphere |volume=58 |issue=11 |pages=1471–96 |date=Mar 2005

|doi=10.1016/j.chemosphere.2004.11.078 |pmid=15694468 }} followed by an ethylene insertion. The olefin is oxidized, removing one carbon to yield products with an odd number of carbons with even-lengthed fluorocarbon chains plus a carboxylic acid group. As the fluorotelomer olefins are dominated by F(CF₂)₈CH=CH₂,{{cite conference

|title=PERFORCE — PERFLUORINATED ORGANIC COMPOUNDS IN THE EUROPEAN ENVIRONMENT

|others=Institute for Biodiversity and Ecosystem Dynamics, Universiteit van Amsterdam

|date=2006-09-15

|url=http://www.science.uva.nl/perforce/Final%20reportA.pdf |pages=18

|accessdate=2009-02-15}} PFNA is the major PFCA product.

Surflon S-111 "is described as Fatty acids, C7-C13, perfluoro, ammonium salts".