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Highly Selective Liquid-Phase Benzylation of Anisole with Solid-Acid Zeolite Catalysts

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Abstract

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.

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Acknowledgments

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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Authors and Affiliations

  1. Department of Chemistry, Centre for Catalysis and Sustainable Chemistry, Technical University of Denmark, Building 207, 2800, Kgs. Lyngby, Denmark

    Raju Poreddy, Shunmugavel Saravanamurugan & Anders Riisager

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  1. Raju Poreddy
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  2. Shunmugavel Saravanamurugan
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  3. Anders Riisager
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Correspondence to Anders Riisager.

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Poreddy, R., Saravanamurugan, S. & Riisager, A. Highly Selective Liquid-Phase Benzylation of Anisole with Solid-Acid Zeolite Catalysts. Top Catal 58, 1053–1061 (2015). https://doi.org/10.1007/s11244-015-0473-y

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  • DOI: https://doi.org/10.1007/s11244-015-0473-y

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