Ester hydrolysis: Conditions for acid autocatalysis and a kinetic switch

Tamás Bánsági; Annette F. Taylor

doi:10.1016/j.tet.2017.05.049

Ester hydrolysis: Conditions for acid autocatalysis and a kinetic switch

Tamás Bánsági, Annette F. Taylor

Department of Chemistry

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

24 Citations (SciVal)

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.

Original language	English
Pages (from-to)	5018-5022
Number of pages	5
Journal	Tetrahedron
Volume	73
Issue number	33
Early online date	25 Jul 2017
DOIs	https://doi.org/10.1016/j.tet.2017.05.049
Publication status	Published - 17 Aug 2017

Bibliographical note

Funding Information:
The authors acknowledge support from EPSRC grant EP/K030574/2.

Publisher Copyright:
© 2017

Funding

The authors acknowledge support from EPSRC grant EP/K030574/2.

Keywords

Acid-base catalysis
Autocatalysis
Ester hydrolysis
Kinetic modelling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2017.05.049

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title = "Ester hydrolysis: Conditions for acid autocatalysis and a kinetic switch",

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.",

keywords = "Acid-base catalysis, Autocatalysis, Ester hydrolysis, Kinetic modelling",

author = "Tam{\'a}s B{\'a}ns{\'a}gi and Taylor, \{Annette F.\}",

note = "Funding Information: The authors acknowledge support from EPSRC grant EP/K030574/2. Publisher Copyright: {\textcopyright} 2017",

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doi = "10.1016/j.tet.2017.05.049",

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T1 - Ester hydrolysis

T2 - Conditions for acid autocatalysis and a kinetic switch

AU - Bánsági, Tamás

AU - Taylor, Annette F.

PY - 2017/8/17

Y1 - 2017/8/17

N2 - 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.

AB - 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.

KW - Acid-base catalysis

KW - Autocatalysis

KW - Ester hydrolysis

KW - Kinetic modelling

UR - https://www.scopus.com/pages/publications/85019579529

U2 - 10.1016/j.tet.2017.05.049

DO - 10.1016/j.tet.2017.05.049

M3 - Article

AN - SCOPUS:85019579529

SN - 0040-4020

VL - 73

SP - 5018

EP - 5022

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Ester hydrolysis: Conditions for acid autocatalysis and a kinetic switch

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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