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Title: Synthesis of 1,2-glycerol carbonate from carbon dioxide: The role of methanol in fluid phase equilibrium
Authors: Podila, S
Plasseraud, L
Cattey, H
Ballivet-Tkatchenko, D
Carrera, G V S M
Nunes da Ponte, M
Neuberg, S
Behr, A
Keywords: Glycerol
Glycerol carbonate
Carbon dioxide
Fluid phase equilibrium
Vapour-liquid equilibrium
Dibutyltin glycerolate
X-ray structure
Issue Date: Sep-2012
Publisher: NISCAIR-CSIR, India
Abstract: The effect of methanol on the synthesis of 1,2-glycerol carbonate from CO2 and glycerol is studied in the presence of Bu2Sn(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, CO2 behaves as an anti-solvent, separating methanol from glycerol, thus inhibiting the formation of 1,2-glycerol carbonate. Dimethyl carbonate is a side-product 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 one-dimensional polymeric chain.
Description: 1330-1338
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections:IJC-A Vol.51A(09-10) [September-October 2012]

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