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Issue 1, 2014
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Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride

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Abstract

A route to renewable phthalic anhydride (2-benzofuran-1,3-dione) from biomass-derived furan and maleic anhydride (furan-2,5-dione) is investigated. Furan and maleic anhydride were converted to phthalic anhydride in two reaction steps: Diels–Alder cycloaddition followed by dehydration. Excellent yields for the Diels–Alder reaction between furan and maleic-anhydride were obtained at room temperature and solvent-free conditions (SFC) yielding 96% exo-4,10-dioxa-tricyclo[5.2.1.0]dec-8-ene-3,5-dione (oxanorbornene dicarboxylic anhydride) after 4 h of reaction. It is shown that this reaction is resistant to thermal runaway because of its reversibility and exothermicity. The dehydration of the oxanorbornene was investigated using mixed-sulfonic carboxylic anhydrides in methanesulfonic acid (MSA). An 80% selectivity to phthalic anhydride (87% selectivity to phthalic anhydride and phthalic acid) was obtained after running the reaction for 2 h at 298 K to form a stable intermediate followed by 4 h at 353 K to drive the reaction to completion. The structure of the intermediate was determined. This result is much better than the 11% selectivity obtained in neat MSA using similar reaction conditions.

Graphical abstract: Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride

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Supplementary files

Article information


Submitted
14 Aug 2013
Accepted
11 Oct 2013
First published
14 Oct 2013

This article is Open Access

Green Chem., 2014,16, 167-175
Article type
Paper

Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride

E. Mahmoud, D. A. Watson and R. F. Lobo, Green Chem., 2014, 16, 167
DOI: 10.1039/C3GC41655K

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