Highly Selective Liquid-Phase Benzylation of Anisole with Solid-Acid Zeolite Catalysts
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Zeolites were evaluated as solid acid catalysts for the liquid-phase benzylation of anisole with benzyl alcohol, benzyl bromide, and benzyl chloride at 80 °C. Among the examined zeolites, H-mordenite-10 (H-MOR-10) demonstrated particular high activity (>99 %) and excellent selectivity (>96 %) to the monobenzylated products, ortho/para benzyl anisole, using benzyl alcohol as reagent (anisole/alcohol molar ratio = 28). Analogous reactions with benzyl halides resulted in lower yields of the desired monobenzylated products. The conversion of benzyl alcohol was confirmed to be proportional to the amount of added H-MOR-10, and the linear free-energy relationship relating the conversion of substituted benzyl alcohol and substituent constants as well as the orientation effect of substituents of anisole on the distribution of ortho/para/meta isomers was evaluated.
KeywordsSolid-acid catalysis Zeolites Benzyl alcohol Aromatic benzylation Substituted anisole
Financial support from the UNIK research initiative Catalysis for Sustainable Energy funded by the Danish Ministry of Science, Technology and Innovation is gratefully acknowledged.
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