Chemistry:Perfluoroalkyl ether sulfonic acid

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

Perfluoroalkyl ether sulfonic acids (abbreviated as PFESAs) refers to compounds with the formula CF
3
(CF
2
)
m
O(CF
2
)
n
SO
3
H
. 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

  1. Strynar, Mark; Dagnino, Sonia; McMahen, Rebecca; Liang, Shuang; Lindstrom, Andrew; Andersen, Erik; McMillan, Larry; Thurman, Michael et al. (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. doi:10.1021/acs.est.5b01215. PMID 26392038. Bibcode2015EnST...4911622S. 
  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. PMID 31909080.