Isosorbide bis(methyl carbonate) synthesis from isosorbide and dimethyl carbonate: the key role of dual basic–nucleophilic catalysts
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Author/sOchoa-Gómez, José R.; Lorenzo-Ibarreta, Leire; Diñeiro-García, Cristina; Gómez-Jiménez-Aberasturi, Olga
Isosorbide bis(methyl carbonate) (IBMC) is a scarcely studied green chemical with potential applications in the manufacturing of non-isocyanate polyurethanes and bisphenol A-free polycarbonates. Its synthesis by transesterification of isosorbide with dimethyl carbonate (DMC) is very negatively influenced by the presence of small amounts of acidic impurities in isosorbide when heterogeneous inorganic carbonates such as potassium and cesium carbonates are used as catalysts. In this paper it is shown that the problem can be solved by using homogeneous catalysts consisting of nitrogenated bases and superbases having a suitable dual nucleophilic–basic character and able to form a highly reactive acyl intermediate with the electrophilic reactant DMC. Cycloaliphatic secondary and tertiary amines, guanidines and amidines covering a nucleophilicity parameter (N) range between 13.58 and 20.58 in either acetonitrile or dichloromethane, and a pKa range in acetonitrile between 15.68 and 26.02 have ...