Substituted Phthalic Anhydrides from Biobased Furanics: A New Approach to Renewable Aromatics.

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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Shanmugam Thiyagarajan, Homer C Genuino, Michał Śliwa, Jan C van der Waal, Ed de Jong, Jacco van Haveren, Bert M Weckhuysen, Pieter C A Bruijnincx, Daan S van Es. Substituted Phthalic Anhydrides from Biobased Furanics: A New Approach to Renewable Aromatics. ChemSusChem. 2015 Sep 21;8(18):3052-6

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PMID: 26235971

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