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Cascade Reductive Etherification of Bioderived Aldehydes over Zr‐Based Catalysts
Author(s) -
Shinde Suhas,
Rode Chandrashekhar
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201701275
Subject(s) - furfural , catalysis , chemistry , furan , transfer hydrogenation , organic chemistry , yield (engineering) , materials science , ruthenium , metallurgy
An efficient one‐pot catalytic cascade sequence has been developed for the production of value‐added ethers from bioderived aldehydes. Etherification of 5‐(hydroxymethyl)furfural with different aliphatic alcohols over acidic Zr–montmorillonite (Zr‐Mont) catalyst produced a mixture of 5‐(alkoxymethyl)furfural and 2‐(dialkoxymethyl)‐5‐(alkoxymethyl)furan. The latter was selectively converted back into 5‐(alkoxymethyl)furfural by treating it with water over the same catalyst. The synthesis of 2,5‐bis(alkoxymethyl)furan was achieved through a cascade sequence involving etherification, transfer hydrogenation, and re‐etherification over a combination of acidic Zr‐Mont and the charge‐transfer hydrogenation catalyst [ZrO(OH) 2 ]. This catalyst combination was further explored for the cascade conversion of 2‐furfuraldehyde into 2‐(alkoxymethyl)furan. The scope of this strategy was then extended for the reductive etherification of lignin‐derived arylaldehydes to obtain the respective benzyl ethers in >80 % yield. Additionally, the mixture of Zr‐Mont and ZrO(OH) 2 does not undergo mutual destruction, which was proved by recycling experiments and XRD analysis. Both the catalysts were thoroughly characterized using BET, temperature‐programmed desorption of NH 3 and CO 2 , pyridine‐FTIR, XRD, inductively coupled plasma optical emission spectroscopy, and X‐ray photoelectron spectroscopy techniques.