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Issue 7, 2012
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Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion

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Abstract

γ-Valerolactone (GVL) has been proposed as a sustainable liquid, and could be used for the production of hydrocarbons by using both homogeneous and heterogeneous catalytic systems. The selective reduction of levulinic acid (LA) to GVL is a key transformation for biorefinery concepts based on platform molecules. We report a detailed investigation of the conversion of LA to GVL using molecular hydrogen in the presence of a catalyst in situ generated from Ru(acac)3, and electronically and sterically characterized alkyl-bis(m-sulfonated-phenyl)- and dialkyl-(m-sulfonated-phenyl)phosphine (RnP(C6H4-m-SO3Na)3−n (n = 1 or 2; R = Me, Pr, iPr, Bu, Cp) ligands. The hydrogenation experiments were performed in the range of 5–100 bar H2 at 140 °C using 0.016 mol% catalyst and 5–20 eqv. of ligand. The effects of hydrogen pressure and Ru/ligand ratio on the LA conversion were determined. The nBuP(C6H4-m-SO3Na)2 (χ = 12.5, θTol = 153°) showed the highest activity achieving turnover numbers up to 6200 with a yield and selectivity higher than 99% in a solvent, chlorine and promoter free reaction mixture. The catalyst was successfully recycled for six consecutive runs without loss of activity. The characterization of sulfonated and non-sulfonated phosphines indicated that the sulfonation had no significant effect on the steric and electronic properties of the ligands.

Graphical abstract: Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion

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Publication details

The article was received on 20 Feb 2012, accepted on 30 Apr 2012 and first published on 30 Apr 2012


Article type: Paper
DOI: 10.1039/C2GC35503E
Citation: Green Chem., 2012,14, 2057-2065
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    Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion

    J. M. Tukacs, D. Király, A. Strádi, G. Novodarszki, Z. Eke, G. Dibó, T. Kégl and L. T. Mika, Green Chem., 2012, 14, 2057
    DOI: 10.1039/C2GC35503E

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