Author: Mahmoud, E.; Watson, D.A.; Lobo, R.F.
Description: 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.
Subject headings: Renewable; Phthalic anhydride; Furan; Maleic anhydride; Biomass
Publication year: 2014
Journal or book title: Green Chem.
Volume: 16
Issue: 1
Pages: 167-175
Find the full text : https://pubs.rsc.org/en/content/articlehtml/2014/gc/c3gc41655k
Find more like this one (cited by): https://scholar.google.com/scholar?cites=16008703908006025160&as_sdt=1000005&sciodt=0,16&hl=en
Type: Journal Article
Serial number: 2347