Perfluoroalkyl ether sulfonic acid

Structural formula of F-53, the potassium salt of a PFESA

Perfluoroalkyl ether sulfonic acids (abbreviated as PFESAs) refers to compounds with the formula CF₃(CF₂)_mO(CF₂)_nSO₃H. Several are known. These compounds are members of the PFAS class of fluorocarbon-based surfactants. They were invented partly in response to the controversy over the persistence of PFAS.^[1] Some PFESAs can be prepared from hexafluoropropylene oxide.^[2]

Studies of PFESAs in lab mice have demonstrated comparatively higher hepatotoxicity than PFOS.^[3] Industrially, PFESAs are used in chromium plating and as a replacement for other PFAS in fluoropolymer manufacturing.^[4]

References

↑ Strynar, Mark; Dagnino, Sonia; McMahen, Rebecca; Liang, Shuang; Lindstrom, Andrew; Andersen, Erik; McMillan, Larry; Thurman, Michael; Ferrer, Imma; Ball, Carol (2015). "Identification of Novel Perfluoroalkyl Ether Carboxylic Acids (PFECAs) and Sulfonic Acids (PFESAs) in Natural Waters Using Accurate Mass Time-of-Flight Mass Spectrometry (TOFMS)". Environmental Science & Technology. 49 (19): 11622–11630. Bibcode:2015EnST...4911622S. doi:10.1021/acs.est.5b01215. PMID 26392038.
↑ Oppenheimer, Jossian; Hsung, Richard P.; Li, Hongyan; Lu, Ting; Wei, Yonggang (2007). "Hexafluoropropene Oxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289x.rn00768. ISBN 978-0-471-93623-7.
↑ Yao, Jingzhi; Pan, Yitao; Sheng, Nan; Su, Zhaoben; Guo, Yong; Wang, Jianshe; Dai, Jiayin (2020-11-03). "Novel Perfluoroalkyl Ether Carboxylic Acids (PFECAs) and Sulfonic Acids (PFESAs): Occurrence and Association with Serum Biochemical Parameters in Residents Living Near a Fluorochemical Plant in China". Environmental Science & Technology. 54 (21): 13389–13398. doi:10.1021/acs.est.0c02888.
↑ Zhang, Chuhui; Hopkins, Zachary R.; McCord, James; Strynar, Mark J.; Knappe, Detlef R. U. (2019). "Fate of Per- and Polyfluoroalkyl Ether Acids in the Total Oxidizable Precursor Assay and Implications for the Analysis of Impacted Water". Environmental Science & Technology Letters. 6 (11): 662–668. doi:10.1021/acs.estlett.9b00525. PMC 6944312. PMID 31909080.

[1] Strynar, Mark; Dagnino, Sonia; McMahen, Rebecca; Liang, Shuang; Lindstrom, Andrew; Andersen, Erik; McMillan, Larry; Thurman, Michael; Ferrer, Imma; Ball, Carol (2015). "Identification of Novel Perfluoroalkyl Ether Carboxylic Acids (PFECAs) and Sulfonic Acids (PFESAs) in Natural Waters Using Accurate Mass Time-of-Flight Mass Spectrometry (TOFMS)". Environmental Science & Technology. 49 (19): 11622–11630. Bibcode:2015EnST...4911622S. doi:10.1021/acs.est.5b01215. PMID 26392038.

[2] Oppenheimer, Jossian; Hsung, Richard P.; Li, Hongyan; Lu, Ting; Wei, Yonggang (2007). "Hexafluoropropene Oxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289x.rn00768. ISBN 978-0-471-93623-7.

[3] Yao, Jingzhi; Pan, Yitao; Sheng, Nan; Su, Zhaoben; Guo, Yong; Wang, Jianshe; Dai, Jiayin (2020-11-03). "Novel Perfluoroalkyl Ether Carboxylic Acids (PFECAs) and Sulfonic Acids (PFESAs): Occurrence and Association with Serum Biochemical Parameters in Residents Living Near a Fluorochemical Plant in China". Environmental Science & Technology. 54 (21): 13389–13398. doi:10.1021/acs.est.0c02888.

[4] Zhang, Chuhui; Hopkins, Zachary R.; McCord, James; Strynar, Mark J.; Knappe, Detlef R. U. (2019). "Fate of Per- and Polyfluoroalkyl Ether Acids in the Total Oxidizable Precursor Assay and Implications for the Analysis of Impacted Water". Environmental Science & Technology Letters. 6 (11): 662–668. doi:10.1021/acs.estlett.9b00525. PMC 6944312. PMID 31909080.

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