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 iss...

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Veröffentlicht in:ChemSusChem Jg. 8; H. 18; S. 3052 - 3056
Hauptverfasser: Thiyagarajan, Shanmugam, Genuino, Homer C., Śliwa, Michał, van der Waal, Jan C., de Jong, Ed, van Haveren, Jacco, Weckhuysen, Bert M., Bruijnincx, Pieter C. A., van Es, Daan S.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Weinheim WILEY-VCH Verlag 21.09.2015
WILEY‐VCH Verlag
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Schlagworte:
aromatics
aromatization
Biomass
Diels-Alder reaction
furans
Furans - chemistry
Green Chemistry Technology - methods
Hydrogenation
Phthalic Anhydrides - chemistry
aromatics
aromatization
Diels-Alder reaction
hydrogenation
furans
ISSN:1864-5631, 1864-564X, 1864-564X
Online-Zugang:Volltext
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Zusammenfassung: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. Er zit een Aldertje onder het gras: The classical two‐step approach to furanics‐derived aromatics, via Diels–Alder (DA) aromatization, is modified into a three‐step procedure to avoid retro‐DA reactions. The new sequence involves a mild hydrogenation step to obtain a stable oxanorbornane intermediate. Subsequent dehydration and dehydrogenation using a physical mixture of acidic zeolites or resins in combination with metal on a carbon support then gives high yields of aromatics under relatively mild conditions.
Bibliographie:ark:/67375/WNG-HSL4J67Q-6
ArticleID:CSSC201500511
Netherlands Organization for Scientific Research (NWO)
istex:AB8ECE7A61591ABF6FCF9B7B94777183A59A08DA
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1864-5631
1864-564X
1864-564X
DOI:10.1002/cssc.201500511