Abstract
Glycerol carbonate was synthesized from renewable glycerol and dimethyl carbonate using lipase in solvent-free reaction system in which excess dimethyl carbonate played as the reaction medium. A variety of lipases have been tested for their abilities to catalyze transesterification reaction, and Candida antartica lipase B and Novozyme 435 exhibited higher catalytic activities. The silica-coated glycerol with a 1:1 ratio was supplied to prevent two-phase formation between hydrophobic dimethyl carbonate and hydrophilic glycerol. Glycerol carbonate was successfully synthesized with more than 90% conversion from dimethyl carbonate and glycerol with a molar ratio of 10 using Novozyme 435-catalyzed transesterification at 70 °C. The Novozyme 435 [5% (w/w) and 20% (w/w)] and silica gel were more than four times recycled with good stability in a repeated batch operation for the solvent-free synthesis of glycerol carbonate.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Werpy T, Peterson G (2004) Top value added chemicals from biomass. US Department of Energy, Oak Ridge
Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F (2008) Improved utilisation of renewable resources: new important derivatives of glycerol. Green Chem 10:13–30
Rokicki G, Rakoczy P, Parzuchowski P, Sobiecki M (2005) Hyperbranched aliphatic polyethers obtained from environmentally benign monomer: glycerol carbonate. Green Chem 7:529–539
Zhou CH, Beltramini JB, Fan YX, Lu GQ (2008) Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem Soc Rev 37:527–549
Hensen H, Loehl T, Tesmann H, Kahre J (1999) Surface-active composition, especially cosmetics, containing glycerol carbonate as emulsifier. EP Patent DE 19756454, 17 June 1999
Aresta M, Dibenedetto A, Nocito F, Pastore C (2006) A study on the carboxylation of glycerol to glycerol carbonate with carbon dioxide: the role of the catalyst, solvent and reaction conditions. J Mol Catal A Chem 257:149–153
Yoo JW, Mouloungui Z (2003) Catalytic carbonylation of glycerin by urea in the presence of zinc mesoporous system for the synthesis of glycerol carbonate. Stud Surf Sci Catal 146:757–760
Kim YH, Lee H, Yoon DY, Song BK (2007) Lipase-catalyzed synthesis of glycerol carbonate from renewable glycerol and dimethyl carbonate through transesterification. J Mol Catal B Enzym 49:75–78
Cave GWV, Raston CL, Scotta JL (2001) Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. Chem Commun 21:2159–2169
Berger M, Laumen K, Schneider MP (1992) Enzymatic esterification of glycerol I. Lipase-catalyzed synthesis of regioisomerically pure 1, 3-sn-diacylglycerols. JAOCS 69:955–960
Castillo E, Dossat V, Marty A, Condoret JS, Combes D (1997) The role of silica gel in lipase-catalyzed esterification reactions of high-polar substrates. JAOCS 74:77–85
Stevenson DE, Stanley RA, Furneaux RH (1994) Near-quantitative production of fatty acid alkyl esters by lipase-catalyzed alcoholysis of fats and oils with adsorption of glycerols by silica gel. Enzyme Microb Technol 16:478–484
Acknowledgments
This work was supported by a grant from the Kyung Hee University in 2009 (KHU-20090750). The scholarship for K. H. Lee was supported by Graduate School of Kyung Hee University.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Lee, K.H., Park, CH. & Lee, E.Y. Biosynthesis of glycerol carbonate from glycerol by lipase in dimethyl carbonate as the solvent. Bioprocess Biosyst Eng 33, 1059–1065 (2010). https://doi.org/10.1007/s00449-010-0431-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00449-010-0431-9