The hydrolysis of geminal ethers: A kinetic appraisal of orthoesters and ketals

Sonia L Repetto, James F Costello*, Craig P. Butts, Joseph K W Lam, Norman M Ratcliffe

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)
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A novel approach to protecting jet fuel against the effects of water contamination is predicated upon the coupling of the rapid hydrolysis reactions of lipophilic cyclic geminal ethers, with the concomitant production of a hydrophilic acyclic hydroxyester with de-icing properties (Fuel Dehydrating Icing Inhibitors - FDII). To this end, a kinetic appraisal of the hydrolysis reactions of representative geminal ethers was undertaken using a convenient surrogate for the fuel-water interface (D2 O/CD3 CN 1:4). We present here a library of acyclic and five/six-membered cyclic geminal ethers arranged according to their hydroxonium catalytic coefficients for hydrolysis, providing for the first time a framework for the development of FDII. A combination of 1H NMR, labelling and computational studies was used to assess the effects that may govern the observed relative rates of hydrolyses.

Original languageEnglish
Pages (from-to)1467-1475
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Early online date15 Jul 2016
Publication statusPublished - 15 Jul 2016


  • FDII
  • Geminal ethers
  • Kinetics

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