Catalysis of the knoevenagel reaction by gamma-aminopropylsilica

D J  Macquarrie; J H  Clark; A  Lambert; J E G  Mdoe; A  Priest

doi:10.1016/S1381-5148(97)00089-8

Catalysis of the knoevenagel reaction by gamma-aminopropylsilica

D J Macquarrie, J H Clark, A Lambert, J E G Mdoe, A Priest

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The Knoevenagel reaction can be catalysed by gamma-aminopropylsilica. Reactions are rapid and essentially quantitative with small amounts of catalyst. A range of aldehydes and ketones can be reacted successfully, the only exceptions being very bulky ketones. The reaction is very dependent on the efficient removal of water, which leads to faster reaction rates and to much higher conversions. The choice of solvent is also extremely important, with nonpolar solvents such as cyclohexane being optimal. Less polar, higher boiling solvents are significantly less effective, even at much higher reaction temperatures. Catalyst poisoning is slow and appears to be due to amide formation on the surface.

Original language	English
Pages (from-to)	153-158
Number of pages	6
Journal	Reactive and Functional Polymers
Volume	35
Issue number	3
DOIs	https://doi.org/10.1016/S1381-5148(97)00089-8
Publication status	Published - Dec 1997

Keywords

green chemistry
silica
base catalysis
solvent effects
knoevenagel
BASE CATALYSTS

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10.1016/S1381-5148(97)00089-8

Cite this

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title = "Catalysis of the knoevenagel reaction by gamma-aminopropylsilica",

abstract = "The Knoevenagel reaction can be catalysed by gamma-aminopropylsilica. Reactions are rapid and essentially quantitative with small amounts of catalyst. A range of aldehydes and ketones can be reacted successfully, the only exceptions being very bulky ketones. The reaction is very dependent on the efficient removal of water, which leads to faster reaction rates and to much higher conversions. The choice of solvent is also extremely important, with nonpolar solvents such as cyclohexane being optimal. Less polar, higher boiling solvents are significantly less effective, even at much higher reaction temperatures. Catalyst poisoning is slow and appears to be due to amide formation on the surface.",

keywords = "green chemistry, silica, base catalysis, solvent effects, knoevenagel, BASE CATALYSTS",

author = "Macquarrie, {D J} and Clark, {J H} and A Lambert and Mdoe, {J E G} and A Priest",

year = "1997",

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AU - Macquarrie, D J

AU - Clark, J H

AU - Lambert, A

AU - Mdoe, J E G

AU - Priest, A

PY - 1997/12

Y1 - 1997/12

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AB - The Knoevenagel reaction can be catalysed by gamma-aminopropylsilica. Reactions are rapid and essentially quantitative with small amounts of catalyst. A range of aldehydes and ketones can be reacted successfully, the only exceptions being very bulky ketones. The reaction is very dependent on the efficient removal of water, which leads to faster reaction rates and to much higher conversions. The choice of solvent is also extremely important, with nonpolar solvents such as cyclohexane being optimal. Less polar, higher boiling solvents are significantly less effective, even at much higher reaction temperatures. Catalyst poisoning is slow and appears to be due to amide formation on the surface.

KW - green chemistry

KW - silica

KW - base catalysis

KW - solvent effects

KW - knoevenagel

KW - BASE CATALYSTS

U2 - 10.1016/S1381-5148(97)00089-8

DO - 10.1016/S1381-5148(97)00089-8

M3 - Article

SN - 1381-5148

VL - 35

SP - 153

EP - 158

JO - Reactive and Functional Polymers

JF - Reactive and Functional Polymers

IS - 3

ER -