Bioprocess and Biosystems Engineering

, Volume 33, Issue 9, pp 1059–1065 | Cite as

Biosynthesis of glycerol carbonate from glycerol by lipase in dimethyl carbonate as the solvent

Original Paper

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.

Keywords

Dimethyl carbonate Glycerol Glycerol carbonate Lipase Transesterification 

References

  1. 1.
    Werpy T, Peterson G (2004) Top value added chemicals from biomass. US Department of Energy, Oak RidgeGoogle Scholar
  2. 2.
    Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F (2008) Improved utilisation of renewable resources: new important derivatives of glycerol. Green Chem 10:13–30CrossRefGoogle Scholar
  3. 3.
    Rokicki G, Rakoczy P, Parzuchowski P, Sobiecki M (2005) Hyperbranched aliphatic polyethers obtained from environmentally benign monomer: glycerol carbonate. Green Chem 7:529–539CrossRefGoogle Scholar
  4. 4.
    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 37:527–549CrossRefGoogle Scholar
  5. 5.
    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 1999Google Scholar
  6. 6.
    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 257:149–153CrossRefGoogle Scholar
  7. 7.
    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 146:757–760CrossRefGoogle Scholar
  8. 8.
    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 49:75–78CrossRefGoogle Scholar
  9. 9.
    Cave GWV, Raston CL, Scotta JL (2001) Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. Chem Commun 21:2159–2169CrossRefGoogle Scholar
  10. 10.
    Berger M, Laumen K, Schneider MP (1992) Enzymatic esterification of glycerol I. Lipase-catalyzed synthesis of regioisomerically pure 1, 3-sn-diacylglycerols. JAOCS 69:955–960CrossRefGoogle Scholar
  11. 11.
    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 74:77–85CrossRefGoogle Scholar
  12. 12.
    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 16:478–484CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  1. 1.Department of Chemical Engineering, Industrial Liaison Research InstituteKyung Hee UniversityYonginRepublic of Korea

Personalised recommendations