Selectivity Control in the Tandem Aromatization of Bio‐Based Furanics Catalyzed by Solid Acids and Palladium

Bio‐based furanics can be aromatized efficiently by sequential Diels–Alder (DA) addition and hydrogenation steps followed by tandem catalytic aromatization. With a combination of zeolite H‐Y and Pd/C, the hydrogenated DA adduct of 2‐methylfuran and maleic anhydride can thus be aromatized in the liqu...

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Vydáno v:ChemSusChem Ročník 10; číslo 1; s. 277 - 286
Hlavní autoři: Genuino, Homer C., Thiyagarajan, Shanmugam, van der Waal, Jan C., de Jong, Ed, van Haveren, Jacco, van Es, Daan S., Weckhuysen, Bert M., Bruijnincx, Pieter C. A.
Médium: Journal Article
Jazyk:angličtina
Vydáno: Germany Wiley Subscription Services, Inc 10.01.2017
John Wiley and Sons Inc
Témata:
acidity
Acids
Adducts
Anhydrides
biomass
Carbon - chemistry
Catalysis
Catalysts
Coupling
Furans - chemistry
Hydrogen-Ion Concentration
Hydrogenation
Palladium
Palladium - chemistry
Petrochemicals industry
Porosity
Selectivity
Steam
Zeolites
Zeolites - chemistry
palladium
biomass
acidity
zeolites
hydrogenation
ISSN:1864-5631, 1864-564X, 1864-564X
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Shrnutí:Bio‐based furanics can be aromatized efficiently by sequential Diels–Alder (DA) addition and hydrogenation steps followed by tandem catalytic aromatization. With a combination of zeolite H‐Y and Pd/C, the hydrogenated DA adduct of 2‐methylfuran and maleic anhydride can thus be aromatized in the liquid phase and, to a certain extent, decarboxylated to give high yields of the aromatic products 3‐methylphthalic anhydride and o‐ and m‐toluic acid. Here, it is shown that a variation in the acidity and textural properties of the solid acid as well as bifunctionality offers a handle on selectivity toward aromatic products. The zeolite component was found to dominate selectivity. Indeed, a linear correlation is found between 3‐methylphthalic anhydride yield and the product of (strong acid/total acidity) and mesopore volume of H‐Y, highlighting the need for balanced catalyst acidity and porosity. The efficient coupling of the dehydration and dehydrogenation steps by varying the zeolite‐to‐Pd/C ratio allowed the competitive decarboxylation reaction to be effectively suppressed, which led to an improved 3‐methylphthalic anhydride/total aromatics selectivity ratio of 80 % (89 % total aromatics yield). The incorporation of Pd nanoparticles in close proximity to the acid sites in bifunctional Pd/H‐Y catalysts also afforded a flexible means to control aromatic products selectivity, as further demonstrated in the aromatization of hydrogenated DA adducts from other diene/dienophile combinations. Balancing act: A balance between the acidity and porosity of H‐Y zeolites and efficient coupling with a Pd catalyst is essential for the selective conversion of bio‐based furanics to renewable aromatic chemicals.
Bibliografie:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1864-5631
1864-564X
1864-564X
DOI:10.1002/cssc.201600776