Synthesis of monoglycerides by esterification of oleic acid with glycerol in heterogeneous catalytic process using tin-organic framework catalyst

Lik H. Wee, Tristan Lescouet, Julia Fritsch, Francesca Bonino, Marcus Rose, Zhijun Sui, Eva Garrier, Dirk Packet, Silvia Bordiga, Stefan Kaskel, Moti Herskowitz, David Farrusseng, Johan A. Martens

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

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.

Original languageEnglish
Pages (from-to)356-363
Number of pages8
JournalCatalysis Letters
Volume143
Issue number4
DOIs
StatePublished - 1 Apr 2013

Keywords

  • Esterification
  • Monoglycerides
  • Oleic acid
  • Tin-organic framework
  • tert-Butanol

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)

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