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A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics
Author(s) -
Thiyagarajan Shanmugam,
Genuino Homer C.,
van der Waal Jan C.,
de Jong Ed,
Weckhuysen Bert M.,
van Haveren Jacco,
Bruijnincx Pieter C. A.,
van Es Daan S.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509346
Subject(s) - aromatization , dehydrogenation , catalysis , chemistry , maleic anhydride , organic chemistry , solvent , toluene , calcination , zeolite , adduct , polymer , copolymer
Renewable aromatics can be conveniently synthesized from furanics by introducing an intermediate hydrogenation step in the Diels–Alder (DA) aromatization route, to effectively block retro‐DA activity. Aromatization of the hydrogenated DA adducts requires tandem catalysis, using a metal‐based dehydrogenation catalyst and solid acid dehydration catalyst in toluene. Herein it is demonstrated that the hydrogenated DA adducts can instead be conveniently converted into renewable aromatics with up to 80 % selectivity in a solid‐phase reaction with shorter reaction times using only an acidic zeolite, that is, without solvent or dehydrogenation catalyst. Hydrogenated adducts from diene/dienophile combinations of (methylated) furans with maleic anhydride are efficiently converted into renewable aromatics with this new route. The zeolite H‐Y was found to perform the best and can be easily reused after calcination.