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Synthesis of 1,2-glycerol carbonate from carbon dioxide: the role of methanol in fluid phase equilibrium
Publication . Podila, S.; Plasseraud, L.; Cattey, H.; Ballivet-Tkatchenko, D.; Carrera, G. V. S. M.; Nunes Da Ponte, M.; Neuberg, S.; Behr, A.; DQ - Departamento de Química; CQFB-REQUIMTE - Centro de Química Fina e Biotecnologia (Lab. Associado REQUIMTE); Scientific Publishers of India
The effect of methanol on the synthesis of 1,2-glycerol carbonate from CO2 and glycerol is studied in the presence of Bu 2Sn(OCH3)2, n-Bu2SnO, and tert-Bu2SnO. At 423 K, up to 2.7 mol% yield in glycerol carbonate, based on glycerol, could be obtained in the pressure range 14-20 MPa. Addition of acetonitrile promotes notably the yield to 7 mol%. Fluid phase equilibrium experiments with the ternary mixture CO2/glycerol/methanol show that the reaction takes place in a liquid phase where methanol dissolves glycerol, CO2, and the tin complexes. Above ∼0.6 mole fraction, CO 2 behaves as an anti-solvent, separating methanol from glycerol, thus inhibiting the formation of 1,2-glycerol carbonate. Dimethyl carbonate is a sideproduct of glycerol carbonation resulting mainly from transesterification between glycerol carbonate and methanol. Glycerol coordination to tin center is evidenced by the isolation of di-tert-Bu2Sn(1,2-glycerolate) complex. Its structure determination by single-crystal X-ray diffraction shows that the remaining OH group of glycerol promotes the formation of onedimensional polymeric chain.
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Fundação para a Ciência e a Tecnologia
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3599-PPCDT
Número da atribuição
ERA-CHEM/0001/2007