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Issue 10, 2012
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Organocatalytic upgrading of the key biorefining building block by a catalytic ionic liquid and N-heterocyclic carbenes

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Abstract

The present study of rapid degradation of the key biorefining building block 5-hydroxymethylfurfural (HMF) in an ionic liquid (IL), 1-ethyl-3-methylimidazolium acetate ([EMIM]OAc), has led to highly selective and efficient upgrading of HMF to 5,5′-di(hydroxymethyl)furoin (DHMF), a promising C12 kerosene/jet fuel intermediate. This HMF upgrading reaction is carried out under industrially favourable conditions (i.e., ambient atmosphere and 60–80 °C), catalyzed by N-heterocyclic carbenes (NHCs), and complete within 1 h; this process selectively produces DHMF with yields up to 98% (by HPLC or NMR) or 87% (unoptimized, isolated yield). Mechanistic studies have yielded four lines of evidence that support the proposed carbene catalytic cycle for this upgrading transformation catalyzed by the acetate IL and NHCs.

Graphical abstract: Organocatalytic upgrading of the key biorefining building block by a catalytic ionic liquid and N-heterocyclic carbenes

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Article information


Submitted
10 Aug 2012
Accepted
04 Sep 2012
First published
12 Sep 2012

Green Chem., 2012,14, 2738-2746
Article type
Paper

Organocatalytic upgrading of the key biorefining building block by a catalytic ionic liquid and N-heterocyclic carbenes

D. (D. J.) Liu, Y. Zhang and E. Y.-X. Chen, Green Chem., 2012, 14, 2738
DOI: 10.1039/C2GC36265A

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