Author: Thiyagarajan, S.; Genuino, H.C.; Sliwa, M.; van der Waal, J.C.; de Jong, E.; van Haveren, J.; Weckhuysen, B.M.; Bruijnincx, P.C.A.; van Es, D.S.
Description: A novel route for the production of renewable aromatic chemicals, particularly substituted phthalic acid anhydrides, is presented. The classical two-step approach to furanics-derived aromatics via Diels-Alder (DA) aromatization has been modified into a three-step procedure to address the general issue of the reversible nature of the intermediate DA addition step. The new sequence involves DA addition, followed by a mild hydrogenation step to obtain a stable oxanorbornane intermediate in high yield and purity. Subsequent one-pot, liquid-phase dehydration and dehydrogenation of the hydrogenated adduct using a physical mixture of acidic zeolites or resins in combination with metal on a carbon support then allows aromatization with yields as high as 84 % of total aromatics under relatively mild conditions. The mechanism of the final aromatization reaction step unexpectedly involves a lactone as primary intermediate.
Subject headings: Biomass; Furans/chemistry; Green Chemistry Technology/methods; Hydrogenation; Phthalic Anhydrides/chemistry; Diels-Alder reaction; aromatics; aromatization; furans; hydrogenation
Subject headings:
Publication year: 2015
Journal or book title: ChemSusChem
Volume: 8
Issue: 18
Pages: 3052-3056
Find the full text :Â https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cssc.201500511
Find more like this one (cited by): https://scholar.google.com/scholar?cites=13591134216128466455&as_sdt=1000005&sciodt=0,16&hl=en
Type: Journal Article
Serial number: 2314