Issue 2, 2005
From the journal:

Green Chemistry

Diels–Alder reactions between maleic anhydride and furan derivatives in supercritical CO2

Dáire J. Cott,a   Kirk J. Ziegler,a   Vincent P. Owens,a   Jeremy D. Glennon,a   Andrew E. Grahamb  and  Justin D. Holmes*a  

* Corresponding authors

a Department of Chemistry and the Supercritical Fluid Centre, University College Cork, Cork, Ireland
E-mail: j.holmes@ucc.ie
Fax: +353 (0)21 4274097
Tel: +353 (0)21 4903608

b Department of Chemistry, University of Wales Swansea, Swansea, UK

Abstract

A comparative analysis of the reactions between maleic anhydride and furan derivatives is presented in near and supercritical carbon dioxide and traditional organic solvents. Reaction kinetics were monitored by UV-vis absorbance spectroscopy in conjunction with an optimization technique which greatly simplified the experimental approach. In all of the reactions studied, supercritical carbon dioxide proved to facilitate a rate enhancement over conventional organic solvents. The reaction between maleic anhydride and furfuryl alcohol at 69 bar and 35 °C was found to proceed 10 times faster in CO2 compared to reactions carried out in diethyl ether. All kinetic results were obtained from reactions undertaken in true homogeneous one phase fluid systems. The results achieved further indicate the potential of using carbon dioxide as a medium to carry out such chemical transformations through more environmentally acceptable processes.

Graphical abstract: Diels–Alder reactions between maleic anhydride and furan derivatives in supercritical CO2

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Article information

DOI
https://doi.org/10.1039/B408327J
Article type
Paper
Submitted
02 Jun 2004
Accepted
03 Dec 2004
First published
10 Jan 2005

Green Chem., 2005,7, 105-110

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Diels–Alder reactions between maleic anhydride and furan derivatives in supercritical CO2

D. J. Cott, K. J. Ziegler, V. P. Owens, J. D. Glennon, A. E. Graham and J. D. Holmes, Green Chem., 2005, 7, 105 DOI: 10.1039/B408327J

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