Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 445891
Title Synthesis of Isoidide through Epimerization of Isosorbide using Ruthenium on Carbon
Author(s) Notre, J.E.L. le; Haveren, J. van; Es, D.S. van
Source ChemSusChem 6 (2013)4. - ISSN 1864-5631 - p. 693 - 700.
DOI http://dx.doi.org/10.1002/cssc.201200714
Department(s) Biobased Chemistry and Technology
Biobased Products
FBR Sustainable Chemistry & Technology
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2013
Keyword(s) dynamic kinetic resolution - chiral building-blocks - renewable resources - biodegradable polymers - secondary alcohols - catalytic isomerization - coating applications - succinic acid - polyesters - derivatives
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
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