Jump to main content
Jump to site search
SCHEDULED MAINTENANCE Close the message box

Maintenance work is planned for Monday 16 August 2021 from 07:00 to 23:59 (BST).

Website performance may be temporarily affected and you may not be able to access some PDFs or images. If this does happen, refreshing your web browser should resolve the issue. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 10, 2012

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

Author affiliations

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

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements