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http://dx.doi.org/10.5012/jkcs.2016.60.4.257

Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate  

Chirumarry, Sridhar (Department of Chemistry, Changwon National University)
Ko, Yohan (Department of Chemistry, Changwon National University)
Jang, Kiwan (Department of Physics, Changwon National University)
Shin, Dong-Soo (Department of Chemistry, Changwon National University)
Publication Information
Journal of the Korean Chemical Society / v.60, no.4, 2016 , pp. 257-260 More about this Journal
Abstract
A new perfluorobutyl substituted cyclic type disodium alkanesulfonate is designed, synthesized and characterized as alternative substance to perfluorooctane sulfonic acid (PFOS, 1), a well-known surfactant. Cylic type sulfonate was accomplished from commercially available 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol in four steps. Bio-degradable perfluorobutyl moiety was introduced from fluorous diol, which is symmetrically substituted amphiphile via installation of an intermediate trifluoromethanesulfonyl ester and easily manipulated by double displacement of triflate using potassium malonate and further reduction followed by nucleophilic ring opening are key reactions to get target disodium alkanesulfonate. The efficiency and simplicity in the synthesis of this material offer a new strategy to design PFOS alternatives.
Keywords
PFOS alternatives; Cyclic-type sulfonate; Semi-fluorinate surfactants; Gemini surfactant; Surface tension;
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