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

Raju Poreddy; Saravanamurugan Shunmugavel; Anders Riisager

doi:10.1007/s11244-015-0473-y

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

Raju Poreddy, Saravanamurugan Shunmugavel, Anders Riisager

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

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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.

Original language	English
Journal	Topics in catalysis
Volume	58
Issue number	14
Pages (from-to)	1053-1061
Number of pages	9
ISSN	1022-5528
DOIs	https://doi.org/10.1007/s11244-015-0473-y
Publication status	Published - 2015

Keywords

Solid-acid catalysis
Zeolites
Benzyl alcohol
Aromatic benzylation
Substituted anisole

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@article{1065da32c52042dfafd4c028c51f2062,

title = "Highly Selective Liquid-Phase Benzylation of Anisole with Solid-Acid Zeolite Catalysts",

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.",

keywords = "Solid-acid catalysis, Zeolites, Benzyl alcohol, Aromatic benzylation, Substituted anisole",

author = "Raju Poreddy and Saravanamurugan Shunmugavel and Anders Riisager",

year = "2015",

doi = "10.1007/s11244-015-0473-y",

language = "English",

volume = "58",

pages = "1053--1061",

journal = "Topics in Catalysis",

issn = "1022-5528",

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TY - JOUR

T1 - Highly Selective Liquid-Phase Benzylation of Anisole with Solid-Acid Zeolite Catalysts

AU - Poreddy, Raju

AU - Shunmugavel, Saravanamurugan

AU - Riisager, Anders

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

KW - Solid-acid catalysis

KW - Zeolites

KW - Benzyl alcohol

KW - Aromatic benzylation

KW - Substituted anisole

U2 - 10.1007/s11244-015-0473-y

DO - 10.1007/s11244-015-0473-y

M3 - Journal article

VL - 58

SP - 1053

EP - 1061

JO - Topics in Catalysis

JF - Topics in Catalysis

SN - 1022-5528

IS - 14

ER -