Imperial College London
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Professor James Wilton-Ely

Faculty of Natural Sciences, Department of Chemistry

Professor of Inorganic Chemistry
 
 
 
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Contact

 

+44 (0)20 7594 9718j.wilton-ely Website

 
 
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Location

 

601bMolecular Sciences Research HubWhite City Campus

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Summary

 

Publications

Citation

BibTex format

@article{Al:2020:10.1021/acssuschemeng.9b06691,
author = {Al, Ghatta A and Wilton-Ely, JDET and Hallett, JP},
doi = {10.1021/acssuschemeng.9b06691},
journal = {ACS Sustainable Chemistry & Engineering},
pages = {2462--2471},
title = {Efficient formation of 2,5-diformylfuran (DFF) in ionic liquids at high substrate loadings and low oxygen pressure with separation through sublimation},
url = {http://dx.doi.org/10.1021/acssuschemeng.9b06691},
volume = {8},
year = {2020}
}
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RIS format (EndNote, RefMan)

TY  - JOUR
AB  - The oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF) using oxygen (1 atm) with a TEMPO and CuCl catalyst system is investigated using a range of imidazolium-based ionic liquids (ILs) and various bases at different HMF substrate loadings (10-50%). This represents the first example of HMF to DFF conversion in ionic liquid media under homogeneous catalysis conditions, revealing dramatic differences in performance between the ILs. In the non-coordinating, hydrophobic ionic liquid, [bmim][NTf2], 90% DFF yield is obtained at 5 mol% catalyst loading after 6 hours at 80 °C at a very high 40% HMF loading. Increasing the temperature to 100 °C leads to a lower yield, attributed to loss of volatile TEMPO from the reaction medium. A system using TEMPO and pyridine immobilized within the ionic liquid [bmim][NTf2] results in selective conversion of HMF to high purity DFF. It also allows the DFF formed to be isolated by sublimation in 81% yield before a further cycle is performed. Subsequent catalyst deactivation is probed by X-ray photoelectron spectroscopy (XPS). Synthesis from fructose in a two-step process achieves a 55% isolated DFF yield. This approach overcomes significant drawbacks previously reported for this transformation, such as solvent toxicity, separation and purification problems as well as the need for high oxygen pressures. Further oxidation of HMF with this system leads to a 62% yield of 5-formyl-2-furancarboxylic acid (FFCA). The separation of this compound can be achieved by sublimation of DFF followed by solvent extraction.
AU  - Al,Ghatta A
AU  - Wilton-Ely,JDET
AU  - Hallett,JP
DO  - 10.1021/acssuschemeng.9b06691
EP  - 2471
PY  - 2020///
SN  - 2168-0485
SP  - 2462
TI  - Efficient formation of 2,5-diformylfuran (DFF) in ionic liquids at high substrate loadings and low oxygen pressure with separation through sublimation
T2  - ACS Sustainable Chemistry & Engineering
UR  - http://dx.doi.org/10.1021/acssuschemeng.9b06691
UR  - https://pubs.acs.org/doi/10.1021/acssuschemeng.9b06691
UR  - http://hdl.handle.net/10044/1/76429
VL  - 8
ER  -
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