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Ester hydrolysis: conditions for acid autocatalysis and a kinetic switch

Ester hydrolysis: conditions for acid autocatalysis and a kinetic switch
Ester hydrolysis: conditions for acid autocatalysis and a kinetic switch
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.
0040-4020
5018-5022
Bánsági, Tamás
3984187d-60fd-47f2-b6cb-f312dcedadae
Taylor, Annette F.
08028a29-428d-4732-b6b1-f7a93389b386
Bánsági, Tamás
3984187d-60fd-47f2-b6cb-f312dcedadae
Taylor, Annette F.
08028a29-428d-4732-b6b1-f7a93389b386

Bánsági, Tamás and Taylor, Annette F. (2017) Ester hydrolysis: conditions for acid autocatalysis and a kinetic switch. Tetrahedron, 73 (33), 5018-5022. (doi:10.1016/j.tet.2017.05.049).

Record type: Article

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.

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More information

Accepted/In Press date: 12 May 2017
e-pub ahead of print date: 13 May 2017
Published date: 25 July 2017
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Identifiers

Local EPrints ID: 499316
URI: http://eprints.soton.ac.uk/id/eprint/499316
DOI: doi:10.1016/j.tet.2017.05.049
ISSN: 0040-4020
PURE UUID: 1dac11ed-5243-45fe-8d5f-6c3904d42084
ORCID for Tamás Bánsági: ORCID iD orcid.org/0009-0000-0279-2353
ORCID for Annette F. Taylor: ORCID iD orcid.org/0000-0003-0071-8306

Catalogue record

Date deposited: 17 Mar 2025 17:30
Last modified: 18 Mar 2025 03:15

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Contributors

Author: Tamás Bánsági ORCID iD
Author: Annette F. Taylor ORCID iD

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