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 |
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Pages (from-to) | 5018-5022 |
Number of pages | 5 |
Journal | Tetrahedron |
Volume | 73 |
Issue number | 33 |
Early online date | 25 Jul 2017 |
DOIs | |
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