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http://dx.doi.org/10.7464/ksct.2010.16.4.239

Synthesis of a Fluorene Carbonate from Fluorenyl Epoxide Using Supercritical Carbon Dioxde  

Sim, Yun-Soo (Department of Chemistry Chemical Engineering, Yeungnam University)
Shim, Jae-Jin (School of Display and Chemical Engineering, Yeungnam University)
Ra, Choon-Sup (Department of Chemistry Chemical Engineering, Yeungnam University)
Publication Information
Clean Technology / v.16, no.4, 2010 , pp. 239-244 More about this Journal
Abstract
The carboxylation of the fluorenyl epoxide with a spiro framework, 9,9'-Bis(4-oxiranylmethoxyphenyl) fluorine (2) was catalyzed by some onium salts such as quaternary ammonium and phosphonium salts to produce the corresponding five-membered cyclic carbonate (3) in an efficient and environmentally benign fashion. The coupling reactions depend greatly on the kind of the halide anions and alkyl chain length of the onium salts. While the reaction was sensitive to the reaction temperature, the reaction trends suggest that the catalytic efficiency of the quaternary ammonium halides may correlate strongly with the melting points of the halides. The reactions using a catalytic amount (2 mol %) of quaternary ammonium bromide with an n-butyl chain at 75.9 bar of $CO_2$ and 393 K give the highest yield of the cyclic carbonate (92%).
Keywords
Spiro compound; Fluorene; Epoxide; Carbonate; Supercritical carbon dioxide; Green reaction;
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Times Cited By KSCI : 2  (Citation Analysis)
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