Issue 9, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
08 Jun 2013
Accepted
11 Jul 2013
First published
12 Jul 2013

Green Chem., 2013,15, 2540-2547

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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