Expeditious Synthesis of Dianionic-Headed 4-Sulfoalkanoic Acid Surfactants

Abstract

4-Sulfoalkanoic acids are a class of important dianionic-headed surfactants. Various 4-sulfoalkanoic acids with straight C8, C10, C12, C14, C16, and C18 chains were synthesized expeditiously through the radical addition of methyl 2-((ethoxycarbonothioyl)thio)acetate to linear terminal olefins and subsequent oxidation with peroxyformic acid. This is a useful and convenient strategy for the synthesis of dianionic-headed surfactants with a carboxylic acid and sulfonic acid functionalities in the head group region.

Discovery of the RAFT/MADIX Process: Mechanistic Insights and Polymer Chemistry Implications

“…The 1-alkene coproduct of the metathesis can serve to prepare surfactants by addition of a xanthate bearing a polar moiety. This is exemplified by addition of succinic xanthate 104 to 1-dodecene 103 , which leads finally to surfactant molecule 106 where the hydrophilicity of the polar succinic head has been reinforced by direct oxidation of the xanthate group in adduct 105 into a sulfonic acid by a combination of hydrogen peroxide and formic acid . The direct introduction of a naked succinic acid motif onto an unactivated alkene is remarkable and could prove valuable for the synthesis of polyimides.…”

“…This is exemplified by addition of succinic xanthate 104 to 1-dodecene 103, which leads finally to surfactant molecule 106 where the hydrophilicity of the polar succinic head has been reinforced by direct oxidation of the xanthate group in adduct 105 into a sulfonic acid by a combination of hydrogen peroxide and formic acid. 43 The direct introduction of a naked succinic acid motif onto an unactivated alkene is remarkable and could prove valuable for the synthesis of polyimides. Indeed, the ability to perform additions with a free carboxylic acid is a hallmark of radical chemistry that is not well appreciated by synthetic organic chemists at large.…”

Erratum: Jiang, J.; et al. Expeditious Synthesis of Dianionic-Headed 4-Sulfoalkanoic Acid Surfactants. Molecules 2017, 22, 640

“…The authors wish to make the following change to their paper [ 1 ]. The name of the first author is incorrectly reported to be ‘Jianghui Jiang’.…”