|Title||Substituted Phthalic Anhydrides from Biobased Furanics : A New Approach to Renewable Aromatics|
|Author(s)||Thiyagarajan, Shanmugam; Genuino, Homer C.; ͆Sliwa, Michał; Waal, J.C. Van Der; Jong, Ed de; Haveren, Jacco van; Weckhuysen, Bert M.; Bruijnincx, Pieter C.A.; Es, D.S. Van|
|Source||ChemSusChem 8 (2015)18. - ISSN 1864-5631 - p. 3052 - 3056.|
FBR Sustainable Chemistry & Technology
|Publication type||Refereed Article in a scientific journal|
|Keyword(s)||aromatics - aromatization - Diels-Alder reaction - furans - hydrogenation|
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.