Fluorinated [beta]-sultones as Precursors to Fluorinated Sulfonic Acids, and New Fluorosulfonyl Containing Monomers/Polymers

• Main Author: Mohtasham, Javid
• Format: Others
• Published: PDXScholar 1989
• Subjects: Fluorine compounds; Sulfonic acids; Esters; Chemistry; Environmental Sciences
• Online Access: https://pdxscholar.library.pdx.edu/open_access_etds/1250; https://pdxscholar.library.pdx.edu/cgi/viewcontent.cgi?article=2249&context=open_access_etds

Sulfur trioxide (SO₃) adds to fluoroolefins of the form RCF=CF₂, (where R = F, SF₅, CF₃, CF₃OCF₂, CF₂=CF(CF₂)₂, CF₃(CF₂)₃O, CF₃O(CF₂)₂OCF₂, or CH₂ClCHClCH₂), yielding the fluorinated [beta]-sultones, RCFCF₂OSO₂. In the case of CF₃(CF₂)₃OCF=CF₂, a reverse addition occurs, giving the sultone, CF₃(CF₂)₃CF₂2OCFCF₂SO₂O. The fluoro [beta]-sultones are capable of undergoing different reactions, such as rearrangement, hydrolysis, esterification, and polymerization. These reactions, will result in the formation of compounds containing the fluorosulfonyl grouping (SO₂F); it is this group that yields the corresponding sulfonic acid upon base/acid treatment. The addition of sodium bisulfite to CF₃CF= CF₂ and CF₃(CF₂)₄CF=CF₂ in the presence of (C₆H₅CO)₂O₂ and Na₂B₄O₇·10H₂O was also studied to produce the corresponding sulfonic acid hydrates of the general formula, R[subscript f]CFHCF₂SO₃H·nH₂O. These acids were prepared, and thus, tested as possible fuel cell electrolytes. Infrared, ¹H and ¹⁹F nuclear magnetic resonance and mass spectra, as well as elemental analyses, will be presented in order to support the proposed structures for the resulted compounds.