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

Dáire J. Cott; Kirk J. Ziegler; Vincent P. Owens; Jeremy D. Glennon; Andrew E. Graham; Justin D. Holmes

doi:10.1039/b408327j

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

Dáire J. Cott^*, Kirk J. Ziegler, Vincent P. Owens, Jeremy D. Glennon, Andrew E. Graham, Justin D. Holmes

^*Corresponding author for this work

Faculty of Computing, Engineering and Science

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

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.

Original language	English
Pages (from-to)	105-110
Number of pages	6
Journal	Green Chemistry
Volume	7
Issue number	2
DOIs	https://doi.org/10.1039/b408327j
Publication status	Published - Feb 2005

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title = "Diels-Alder reactions between maleic anhydride and furan derivatives in supercritical CO2",

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. ",

author = "Cott, {D{\'a}ire J.} and Ziegler, {Kirk J.} and Owens, {Vincent P.} and Glennon, {Jeremy D.} and Graham, {Andrew E.} and Holmes, {Justin D.}",

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doi = "10.1039/b408327j",

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T1 - Diels-Alder reactions between maleic anhydride and furan derivatives in supercritical CO2

AU - Cott, Dáire J.

AU - Ziegler, Kirk J.

AU - Owens, Vincent P.

AU - Glennon, Jeremy D.

AU - Graham, Andrew E.

AU - Holmes, Justin D.

PY - 2005/2

Y1 - 2005/2

N2 - 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.

AB - 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.

U2 - 10.1039/b408327j

DO - 10.1039/b408327j

M3 - Article

AN - SCOPUS:14644416624

SN - 1463-9262

VL - 7

SP - 105

EP - 110

JO - Green Chemistry

JF - Green Chemistry

IS - 2

ER -

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

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