Copper catalysed hydrolysis of acrylonitrile to acrylamide: Solvent effects

J. C. Lee; N. W. Cant; D. L. Trimm; M. S. Wainwright

doi:10.1016/S0166-9834(00)80734-4

Copper catalysed hydrolysis of acrylonitrile to acrylamide: Solvent effects

J. C. Lee^*, N. W. Cant, D. L. Trimm, M. S. Wainwright

^*Corresponding author for this work

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

3 Citations (Scopus)

Abstract

The effect of ethanol and dioxane as solvents for water on the hydrolysis of acrylonitrile to acrylamide in the presence of Raney copper catalysts has been investigated. Both solvents lower the rate but the reduction is somewhat greater for dioxane. The magnitude of the effect is best explained in terms of a Langmuir-Hinshelwood model in which both acrylonitrile and water are adsorbed. The added solvent inhibits reaction through competitive adsorption thus reducing the surface concentration of the two reactants. Substitution of ²H₂O changes the hydrolysis rate only slightly leading to the suggestion that the slow step is addition of water to acrylonitrile adsorbed by partial opening of the CN bond. The hydroxyimine species so formed then yields acrylonitrile by rearrangement.

Original language	English
Pages (from-to)	215-222
Number of pages	8
Journal	Applied Catalysis
Volume	57
Issue number	1
DOIs	https://doi.org/10.1016/S0166-9834(00)80734-4
Publication status	Published - 1990

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title = "Copper catalysed hydrolysis of acrylonitrile to acrylamide: Solvent effects",

abstract = "The effect of ethanol and dioxane as solvents for water on the hydrolysis of acrylonitrile to acrylamide in the presence of Raney copper catalysts has been investigated. Both solvents lower the rate but the reduction is somewhat greater for dioxane. The magnitude of the effect is best explained in terms of a Langmuir-Hinshelwood model in which both acrylonitrile and water are adsorbed. The added solvent inhibits reaction through competitive adsorption thus reducing the surface concentration of the two reactants. Substitution of 2H2O changes the hydrolysis rate only slightly leading to the suggestion that the slow step is addition of water to acrylonitrile adsorbed by partial opening of the CN bond. The hydroxyimine species so formed then yields acrylonitrile by rearrangement.",

author = "Lee, {J. C.} and Cant, {N. W.} and Trimm, {D. L.} and Wainwright, {M. S.}",

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AU - Lee, J. C.

AU - Cant, N. W.

AU - Trimm, D. L.

AU - Wainwright, M. S.

PY - 1990

Y1 - 1990

N2 - The effect of ethanol and dioxane as solvents for water on the hydrolysis of acrylonitrile to acrylamide in the presence of Raney copper catalysts has been investigated. Both solvents lower the rate but the reduction is somewhat greater for dioxane. The magnitude of the effect is best explained in terms of a Langmuir-Hinshelwood model in which both acrylonitrile and water are adsorbed. The added solvent inhibits reaction through competitive adsorption thus reducing the surface concentration of the two reactants. Substitution of 2H2O changes the hydrolysis rate only slightly leading to the suggestion that the slow step is addition of water to acrylonitrile adsorbed by partial opening of the CN bond. The hydroxyimine species so formed then yields acrylonitrile by rearrangement.

AB - The effect of ethanol and dioxane as solvents for water on the hydrolysis of acrylonitrile to acrylamide in the presence of Raney copper catalysts has been investigated. Both solvents lower the rate but the reduction is somewhat greater for dioxane. The magnitude of the effect is best explained in terms of a Langmuir-Hinshelwood model in which both acrylonitrile and water are adsorbed. The added solvent inhibits reaction through competitive adsorption thus reducing the surface concentration of the two reactants. Substitution of 2H2O changes the hydrolysis rate only slightly leading to the suggestion that the slow step is addition of water to acrylonitrile adsorbed by partial opening of the CN bond. The hydroxyimine species so formed then yields acrylonitrile by rearrangement.

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DO - 10.1016/S0166-9834(00)80734-4

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VL - 57

SP - 215

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JO - Applied Catalysis

JF - Applied Catalysis

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ER -

Copper catalysed hydrolysis of acrylonitrile to acrylamide: Solvent effects

Abstract

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