Bánsági, T. and Taylor, A.F. orcid.org/0000-0003-0071-8306 (2017) Ester hydrolysis: Conditions for acid autocatalysis and a kinetic switch. Tetrahedron, 73 (33). pp. 5018-5022. ISSN 0040-4020
Abstract
Autocatalysis can be used to obtain a sharp switch in state after a programmable time lag. Here, autocatalysis driven by acid concentration during the dissolution and hydrolysis of solid esters was investigated. In a generic model of the process, conditions were identified for observation of a kinetic switch with the introduction of an inhibitor species, bicarbonate, to delay the onset of autocatalysis. The kinetic profiles from the hydrolysis of two esters, d-gluconic acid δ-lactone and dl-lactide, were examined and evidence for dissolution-limited acid autocatalysis was obtained with lactide.
Metadata
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Copyright, Publisher and Additional Information: | © 2017 Elsevier. This is an author produced version of a paper subsequently published in Tetrahedron. Uploaded in accordance with the publisher's self-archiving policy. Article available under the terms of the CC-BY-NC-ND licence (https://creativecommons.org/licenses/by-nc-nd/4.0/) | ||||
Keywords: | Autocatalysis; Ester hydrolysis; Acid-base catalysis; Kinetic modelling | ||||
Dates: |
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Institution: | The University of Sheffield | ||||
Academic Units: | The University of Sheffield > Faculty of Engineering (Sheffield) > Department of Chemical and Biological Engineering (Sheffield) | ||||
Funding Information: |
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Depositing User: | Symplectic Sheffield | ||||
Date Deposited: | 23 May 2017 09:39 | ||||
Last Modified: | 13 May 2018 00:38 | ||||
Published Version: | https://doi.org/10.1016/j.tet.2017.05.049 | ||||
Status: | Published | ||||
Publisher: | Elsevier | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1016/j.tet.2017.05.049 |