Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate 


Vol. 60,  No. 4, pp. 257-260, Aug.  2016
10.5012/jkcs.2016.60.4.257


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  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.

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  Cite this article

[IEEE Style]

S. Chirumarry, Y. Ko, K. Jang, D. S. Shin, "Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate," Journal of the Korean Chemical Society, vol. 60, no. 4, pp. 257-260, 2016. DOI: 10.5012/jkcs.2016.60.4.257.

[ACM Style]

Sridhar Chirumarry, Yohan Ko, Kiwan Jang, and Dong Soo Shin. 2016. Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate. Journal of the Korean Chemical Society, 60, 4, (2016), 257-260. DOI: 10.5012/jkcs.2016.60.4.257.

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ISSN(Print) 1017-2548
ISSN(Online) 2234-8530