Science China Chemistry

, Volume 53, Issue 9, pp 1953–1956 | Cite as

One-step selective synthesis of branched 1-O-alkyl-glycerol/diglycerol monoethers by catalytic reductive alkylation of ketones

  • Yan Shi
  • Wissam Dayoub
  • Guo-Rong Chen
  • Marc Lemaire


Branched 1-O-alkyl glycerol and diglycerol monoethers were obtained in good yields and high selectivity by a straightforward catalytic reductive alkylation of glycerol with relevant ketones in the presence of 0.5 mol% of Pd/C under 10 bar of hydrogen pressure using a Brønsted acid as the co-catalyst.


glycerol monoether diglycerol monoether 1-O-alkylation Pd/C reduction 


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  1. 1.
    Pagliaro M, Ciriminna R, Kimura H, Rossi M, Della Pina A. From glycerol to value-add products. Angew Chem Int Ed, 2007, 46: 4434–4440CrossRefGoogle Scholar
  2. 2.
    Zhou CH, Beltramini JN., Fan YX, Lu GQ. Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem Soc Rev, 2008, 37: 527–549CrossRefGoogle Scholar
  3. 3.
    Vicente G, Martínez M, Aracil J. Integrated biodiesel production: A comparison of different homogeneous catalysts systems. Bioresource Technol, 2004, 92: 297–305CrossRefGoogle Scholar
  4. 4.
    Werpy T, Petersen G. Top Value Added Chemicals from Biomass. US Department of Energy (USDOE), 2004, Vol. 1Google Scholar
  5. 5.
    Review see: (a) Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F. Improved utilisation of renewable resources: New important derivatives of glycerol. Green Chem, 2008, 10: 13–30CrossRefGoogle Scholar
  6. 5 (b).
    Jérôme F, Pouilloux Y, Barrault J. Rational Design of solid catalysts for the selective use of glycerol as a natural organic building block. Chem Sus Chem, 2008, 1: 586–613Google Scholar
  7. 6 (a).
    Hazra AG, Chatterjee P. A nontoxic antitumour compound from the leaves of Bauhinia scandens characterized as 1-O-alkyl glycerol by gas-liquid chromatography and evaluation of its antitumour property by Brine Shrimp bioassay. Ind Crop Prod, 2008, 27: 39–43CrossRefGoogle Scholar
  8. 6 (b).
    Erdlenbruch B, Jendrossek V, Eibl H, Lakomek M, Transient and controllable opening of the blood-brain barrier to cytostatic and antibiotic agents by alkylglycerols in rats. Exp brain Res, 2000, 135: 417–422CrossRefGoogle Scholar
  9. 6 (c).
    Brohult AH, Brohult SFA. Oral alkyl glycerol ether improvement in radiation, radiomimetic, or cytostatic tumor therapies US patent 3432602, 1969-03-11Google Scholar
  10. 7 (a).
    Aoyama H, Ishii D. Hair straighteners containing keratin-reducing agents and glycerin monoethers and hair straightening method using them. JP Patent 2007045801, 2007-02-22Google Scholar
  11. 7 (b).
    Kao Corp. Hair preparations containing glycerol α-mono-ethers. JP Patent 58083606, 1983-05-19Google Scholar
  12. 7 (c).
    Inoue T, Tsukuda K, Morii T. Liquid cleaning agent composition. JP patent 11256198, 1999-09-21Google Scholar
  13. 7 (d).
    Kaburagi T, Ochiai Y, Okano Y, Masaki H. JP Patent 2007063140, 2007-03-15Google Scholar
  14. 7 (e).
    Shibuya T, Shimada Y, Hashimoto S, Antiseptic agents comprising glyceryl ethers and glycerin esters. JP Patent 2007254342, 2007-10-04Google Scholar
  15. 7 (f).
    Singh S, Bhadani A, Kamboj R, Synthesis of β-bromo glycerol monoethers from α-olefins. Ind Eng ChemRes, 2008, 47: 8090–8094CrossRefGoogle Scholar
  16. 8.
    Garman E, Murray JW. Heavy-atom derivatization. Acta Crystallogr D Biol Crystallogr, 2003, 59: 1903–1913CrossRefGoogle Scholar
  17. 9.
    Gu Y-L, Azzouzi A, Pouilloux Y, Jérôme F, Barrault J. Heterogeneously catalyzed etherification of glycerol: new pathways for transformation of glycerol to more valuable chemicals. Green Chem, 2008, 10: 164–167CrossRefGoogle Scholar
  18. 10 (a).
    Urata K, Yano S, Kawamata A, Takaishi N, Inamoto Y. A convenient synthesis of long-chain 1-O-alkyl glyceryl ethers. J Am Oil Chem Soc, 1988, 65: 1299–1302CrossRefGoogle Scholar
  19. 10 (b).
    Queste S, Bauduin P, Touraud D, Kunzb W, Aubry J-M. Short chain glycerol 1-monoethers — A new class of green solvo-surfactants. Green Chem, 2006, 8: 822–830CrossRefGoogle Scholar
  20. 11.
    Pariente S, Tanchoux N, Fajula F, Etherification of glycerol with ethanol over solid acid catalysts. Green Chem, 2008, 11: 1256–1261CrossRefGoogle Scholar
  21. 12 (a).
    Bethmont V, Fache F, Lemaire M. An alternative catalytic Method to the Williamson’s synthesis of ethers. Tetrahedron Lett, 1995, 36: 4235–4236CrossRefGoogle Scholar
  22. 12 (b).
    Fache F, Bethmont V, Jacquot L, Lemaire M, Reductive O- and N- alkylations. Alternative catalytic methods to nucleophilic substitution. Rec Trav Chim Pas-Bas, 1996, 115: 231–238CrossRefGoogle Scholar
  23. 13.
    Shi Y, Dayoub W, Favre-Réguillon A, Chen G-R, Lemaire M. Straightforward selective synthesis of linear 1-O-alkyl glycerol and di-glycerol monoethers. Tetrahedron Lett, 2009, 59: 6891–6893CrossRefGoogle Scholar
  24. 14.
    Fan J, Wan C, Wang Q, Gao L, Zheng X, Wang Z. Palladium catalyzed isomerization of alkenes: A pronounced influence of an o-phenol hydroxyl group. Org Bio Chem, 2009, 7: 3168–3172CrossRefGoogle Scholar

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© Science China Press and Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  • Yan Shi
    • 1
    • 2
  • Wissam Dayoub
    • 2
  • Guo-Rong Chen
    • 1
  • Marc Lemaire
    • 2
  1. 1.Laboratory for Advanced Materials and Institute of Fine ChemicalsEast China University of Science and TechnologyShanghaiChina
  2. 2.Laboratoire de Catalyse Synthèse et Environnement, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS, UMR5246Université Lyon 1VilleurbanneFrance

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