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

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

Authors

Joseph K.W. Lam

Sonia L. Repetto

Sonia Repetto sonia.repetto@uwe.ac.uk

Joseph K W Lam

Craig P. Butts



Abstract

© 2016 Repetto et al. 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.

Journal Article Type Article
Publication Date Jul 15, 2016
Journal Beilstein Journal of Organic Chemistry
Print ISSN 1860-5397
Electronic ISSN 1860-5397
Publisher Beilstein-Institut
Peer Reviewed Peer Reviewed
Volume 12
Pages 1467-1475
APA6 Citation Lam, J. K., Repetto, S. L., Repetto, S., Costello, J. F., Butts, C. P., Lam, J. K. W., & Ratcliffe, N. M. (2016). The hydrolysis of geminal ethers: A kinetic appraisal of orthoesters and ketals. Beilstein Journal of Organic Chemistry, 12, 1467-1475. https://doi.org/10.3762/bjoc.12.143
DOI https://doi.org/10.3762/bjoc.12.143
Keywords FDII, geminal ethers, kinetics
Publisher URL http://dx.doi.org/10.3762/bjoc.12.143

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