Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 498617
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.
DOI https://doi.org/10.1002/cssc.201500511
Department(s) FBR Sustainable Chemistry & Technology
Biobased Products
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2015
Keyword(s) aromatics - aromatization - Diels-Alder reaction - furans - hydrogenation
Abstract

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.

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