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Dramatic Enhancement of Enone Epoxidation Rates in Nonionic Microemulsions by Thomas Wielpütz; Thomas Sottmann; Reinhard Strey; Friederike Schmidt; Albrecht Berkessel is a Chemistry article available to read on EtoBox.

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## Abstract The ability of microemulsions to dissolve polar and non‐polar components with a huge internal interface can overcome the reagent incompatibilities frequently encountered in organic reactions. We investigated model epoxidation reactions of α,β‐unsaturated enones and alkaline hydrogen peroxide in different nonionic microemulsions, both in the presence and absence of a phase‐transfer agent (PTA). The obtained reaction profiles were compared with those for the corresponding surfactant‐free two‐phase systems. In addition, we defined a time constant __τ__ as a measure for the rate of turnover. The epoxidation of __trans__‐chalcone using an __n__‐alkyl‐polyoxyethylene surfactant based microemulsion was fastest in the system with the PTA (__τ__=66 min) and slightly slower without the PTA (__τ__=77 min). It was still slower in the two‐phase system with a PTA (__τ__=114 min) and extremely sluggish without a phase‐transfer agent. With __n__‐alkyl β‐D‐glucopyranoside as the surfactant the conversion was twice as fast than in the former microemulsion systems, but the PTA did not accelerate the reaction further (__τ__=35 and 33 min). The epoxidation of vitamin K~3~, the second model

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Author

Thomas Wielpütz; Thomas Sottmann; Reinhard Strey; Friederike Schmidt; Albrecht Berkessel

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)

Published

2006

Language

EN

Field

Chemistry (Physical Sciences)