Ester hydrolysis: Conditions for acid autocatalysis and a kinetic switch

Tamás Bánsági, Annette F. Taylor

Research output: Contribution to journalArticlepeer-review

19 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 languageEnglish
Pages (from-to)5018-5022
Number of pages5
JournalTetrahedron
Volume73
Issue number33
Early online date25 Jul 2017
DOIs
Publication statusPublished - 17 Aug 2017

Bibliographical note

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

Publisher Copyright:
© 2017

Keywords

  • Acid-base catalysis
  • Autocatalysis
  • Ester hydrolysis
  • Kinetic modelling

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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