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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 60, Number 4
JKCSEZ 60(4)
August 20, 2016 

 
Title
Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate
Author
Sridhar Chirumarry, Yohan Ko, Kiwan Jang, Dong Soo Shin*
Keywords
PFOS alternatives, Cyclic-type sulfonate, Semi-fluorinate surfactants, Gemini surfactant, Surface tension
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.
Page
257 - 260
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