Synthesis of Isoidide through Epimerization of Isosorbide using Ruthenium on Carbon

J.E.L. le Notre, J. van Haveren, D.S. van Es

Research output: Contribution to journalArticleAcademicpeer-review

19 Citations (Scopus)

Abstract

A highly efficient procedure for obtaining resin-grade isoidide through catalytic epimerization of isosorbide using a ruthenium-on-carbon (Ru/C) catalyst is reported. A comprehensive reaction-parameter variation study involving substrate concentration, catalyst (type of metal, support, and loading), initial pH value, hydrogen pressure, solvent, and reaction temperature demonstrates that superior performance and high selectivity can be achieved. Epimerization of isosorbide in water (pH 8) at 220¿°C, under 40 bar of hydrogen, and using a Ru/C catalyst (5¿% Ru) for 2 h results in a thermodynamic equilibrium mixture containing 55¿% isoidide, 40¿% isosorbide, and 5¿% isomannide. In comparison with previously reported nickel-based catalysts, the Ru/C catalyst is advantageous because it is highly active (as low as 360 ppm Ru) and recyclable. High purity isoidide is obtained by high-vacuum distillation of an equilibrium mixture on a 200 g scale. The high substrate loading (50 wt¿% in water), high selectivity, and the possibility for substrate reuse makes this procedure highly atom efficient and therefore, highly attractive for industrial use
Original languageEnglish
Pages (from-to)693-700
JournalChemSusChem
Volume6
Issue number4
DOIs
Publication statusPublished - 2013

Keywords

  • dynamic kinetic resolution
  • chiral building-blocks
  • renewable resources
  • biodegradable polymers
  • secondary alcohols
  • catalytic isomerization
  • coating applications
  • succinic acid
  • polyesters
  • derivatives

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