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A Two Phase System for Clean and High Yield Synthesis of Furylmethane Derivatives over -SO3H Functionalized Ionic Liquids

Abstract

We report here a new and effective unique two-phase reaction system for high yield production of tri(furyl)methane from furfural and furan. This strategy included acidic aqueous phase (water + -SO3H functionalized IL) and furan phase which significantly suppressed polymer formation thereby increased the yield of tri(furyl)methane. Furan served as a reactant as well as an extraction solvent for the recovery of the condensation products. For the comparision purpose different -SO3H functionalized ionic liquids were prepared and evaluted their performances in condensation of furan and furfural. Ionic liquids with alkyl chain linkers were found to be more effective and acidic than that of imidazolium linked N-sulfonic acids. In addition to that, increase in carbon chain length between imidazole/tri-ethylamine/pyridine and -SO3H, increases the catalytic activity of respective ionic liquids. Among the several preapered ionic liquids, strong acidic imidazolium based butylsulfonic acid (6) showed the best activity with a maximum of 84% yield of condensation product. This strategy offers significantly high yield production of condensation products of furan and furfural as compared to the traditional mineral acid route. The activity and stability of the -SO3H functionalized IL was confirmed by its successful seven recycles without loss of the activity. This new strategy was then extended successfully for the condensation of furan derivatives (e.g. furan and 2-methylfuran) with several different aldehydes, ketones and alcohols.

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Publication details

The article was received on 06 Jun 2017, accepted on 13 Jul 2017 and first published on 14 Jul 2017


Article type: Paper
DOI: 10.1039/C7GC01654A
Citation: Green Chem., 2017, Accepted Manuscript
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    A Two Phase System for Clean and High Yield Synthesis of Furylmethane Derivatives over -SO3H Functionalized Ionic Liquids

    S. H. Shinde and C. V. Rode, Green Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7GC01654A

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