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Synthesis of Bifunctional Phosphonium Salts Bearing Perfluorinated Side Chains and Their Application in the Synthesis of Cyclic Carbonates from Epoxides and CO2

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The synthesis of bifunctional phosphonium salts bearing perfluorinated side chains is reported. These salts were employed as catalysts in the synthesis of cyclic carbonates from CO2 and epoxides. The most efficient catalyst proved to be suitable for the synthesis of cyclic carbonates even at room temperature. The possibility of its recycling was investigated.


Abstract

The synthesis of three bifunctional phosphonium salts bearing perfluorinated side chains is reported. These compounds were employed as catalysts for the synthesis of cyclic carbonates from epoxides and CO2. The most efficient catalyst comprised a phenolic substructure and allowed the synthesis of various carbonates at room temperature and a CO2 pressure as low as 0.1 MPa. The reaction could be performed in perfluorodecalin which in some cases led to improved yields and facilitated the separation of the catalyst. Furthermore, the isolation from the reaction mixture and recyclability of two catalysts was evaluated. However, the activity of the recycled catalysts gradually decreases due to partial decomposition. In total 16 cyclic carbonates were prepared in yields up to 97%.

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