title: The hydrolysis of geminal ethers: a kinetic appraisal of orthoesters and ketals.
abstract: 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 (D2O/CD3CN 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 (1)H NMR, labelling and computational studies was used to assess the effects that may govern the observed relative rates of hydrolyses.
authors: Faculty of Applied Sciences, University of the West of England, Bristol, BS16 1QY, UK.
authors: Sonia L
authors: SL
authors: Repetto
authors: Faculty of Applied Sciences, University of the West of England, Bristol, BS16 1QY, UK.
authors: James F
authors: JF
authors: Costello
authors: School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK.
authors: Craig P
authors: CP
authors: Butts
authors: Airbus Operations Ltd., Filton, Bristol, BS34 7PA, UK.
authors: Joseph K W
authors: JK
authors: Lam
authors: Faculty of Applied Sciences, University of the West of England, Bristol, BS16 1QY, UK.
authors: Norman M
authors: NM
authors: Ratcliffe
keywords: FDII; geminal ethers; kinetics