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Issue 9, 2013
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Single pot conversion of furfuryl alcohol to levulinic esters and γ-valerolactone in the presence of sulfonic acid functionalized ILs and metal catalysts

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Abstract

Ionic liquids functionalized with acidic anions, HSO4, ClSO3H, PTSA, TFA (MIm), HSO4 and TFA (NMP) were found to efficiently (99% conversion) catalyze the alcoholysis of furfuryl alcohol (FAL) in the presence of methanol, ethanol, n-butanol and isopropyl alcohol (IPA) to the corresponding levulinic acid esters under mild temperature (90–130 °C) conditions. The extended alkyl chain length of [MIm] using 1,4-butane sultone enhanced the Brønsted acidity of [BMIm-SH][HSO4] catalyst resulting into the highest selectivity of >95% to Me-LA. An increase in both temperature and catalyst concentration increased the furfuryl alcohol conversion and selectivity to levulinate esters. In contrast, an increase in the substrate concentration from 5 to 15% caused a decrease in Me-LA selectivity due to accumulation of intermediate ethers of furfuryl alcohol. Using a combination of [BMIm-SH][HSO4] and 5% Ru/C catalyst, direct conversion of FAL to γ-valerolactone (GVL) is shown for the first time. A complete conversion of FAL with the highest selectivity of 68% to GVL could be achieved under optimum conditions while higher Ru loading enhanced the GVL selectivity to 94% in the hydrogenation step of this tandem approach. Our catalyst system could be efficiently recycled five times retaining the original activity and selectivity levels.

Graphical abstract: Single pot conversion of furfuryl alcohol to levulinic esters and γ-valerolactone in the presence of sulfonic acid functionalized ILs and metal catalysts

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Publication details

The article was received on 08 Jun 2013, accepted on 11 Jul 2013 and first published on 12 Jul 2013


Article type: Paper
DOI: 10.1039/C3GC41098F
Citation: Green Chem., 2013,15, 2540-2547
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    Single pot conversion of furfuryl alcohol to levulinic esters and γ-valerolactone in the presence of sulfonic acid functionalized ILs and metal catalysts

    A. M. Hengne, S. B. Kamble and C. V. Rode, Green Chem., 2013, 15, 2540
    DOI: 10.1039/C3GC41098F

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