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Synthesis of Monoglycerides by Esterification of Oleic Acid with Glycerol in Heterogeneous Catalytic Process Using Tin–Organic Framework Catalyst

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Abstract

Selective synthesis of monoglycerides by esterification of glycerol with fatty acids is a difficult reaction because of immiscibility of reagents and the formation of di- and tri-glyceride by-products. In this work a heterogeneous catalytic process was conceived in which the reactant mixture was homogenized using tert-butanol solvent. Candidate catalysts were screened in the reaction of oleic acid with glycerol. While under such reaction conditions zeolites were rather inactive, metal–organic frameworks and, especially, tin–organic frameworks were found promising. A tin–organic framework (Sn–EOF) was most active and achieved ≥98 % monoglyceride selectivity at 40 % conversion in catalyzing esterification of oleic acid with glycerol at a low reaction temperature of 150 °C. Leaching of tin from Sn–EOF catalyst was suppressed by limiting the amount of oleic acid in the starting mixture. Characterization of the acid sites of Sn–EOF by pyridine-chemisorption and FTIR revealed Lewis acidity to be responsible for the catalytic activity.

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Acknowledgments

The authors gratefully acknowledge financial support from the EU FP-7 Framework NANOMOF project under grant agreement CP-IP 228604-2. JAM acknowledges the Flemish government for long-term structural funding (Methusalem).

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Authors and Affiliations

  1. Centre for Surface Chemistry and Catalysis, KU Leuven, Kasteelpark Arenberg 23, Heverlee, B3001, Belgium

    Lik H. Wee & Johan A. Martens

  2. Institut de Recherche sur la Catalyse et l’Environnement de Lyon (IRCELYON), CNRSC, University Lyon 1, 2 Av. Albert Einstein, 69626, Villeurbanne, France

    Tristan Lescouet & David Farrusseng

  3. Department for Inorganic Chemistry, Dresden University of Technology, 01062, Dresden, Germany

    Julia Fritsch, Marcus Rose & Stefan Kaskel

  4. Department of Chemistry, NIS Centre of Excellence, University of Turin, Via P. Giuria 7, 10125, Turino, Italy

    Francesca Bonino & Silvia Bordiga

  5. Department of Chemistry, INSTM Reference Center, University of Turin, Via Quarello 11, 10135, Turino, Italy

    Francesca Bonino & Silvia Bordiga

  6. Blechner Center for Industrial Catalysis and Process Development, Ben-Gurion University of the Negev, Beer-Sheva, Israel

    Zhijun Sui & Moti Herskowitz

  7. Novance, Rue les rives de l’Oise, Venette, B.P. 20609, 60206, Compiegne Cedex, France

    Eva Garrier & Dirk Packet

Authors
  1. Lik H. Wee
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  2. Tristan Lescouet
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  3. Julia Fritsch
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  5. Marcus Rose
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  6. Zhijun Sui
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  7. Eva Garrier
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  8. Dirk Packet
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  9. Silvia Bordiga
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  10. Stefan Kaskel
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  11. Moti Herskowitz
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  12. David Farrusseng
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  13. Johan A. Martens
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Corresponding author

Correspondence to Johan A. Martens.

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Wee, L.H., Lescouet, T., Fritsch, J. et al. Synthesis of Monoglycerides by Esterification of Oleic Acid with Glycerol in Heterogeneous Catalytic Process Using Tin–Organic Framework Catalyst. Catal Lett 143, 356–363 (2013). https://doi.org/10.1007/s10562-013-0970-1

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  • DOI: https://doi.org/10.1007/s10562-013-0970-1

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