Abstract
Different types of microemulsion formulations have been explored as reaction medium for the ring opening of a lipophilic epoxide, 1,2-epoxyoctane, with sodium hydrogen sulfite. In two-phase systems without surfactant or phase-transfer reagent the reaction is very sluggish. Microemulsions based on alcohol ethoxylate proved to be efficient reaction media, giving almost complete conversion of epoxide to hydroxysulfonate in 2 h at 75°C. A microemulsion based on the anionic surfactant sodium dodecylsulfate gave a slower rate of epoxide consumption. In addition, the dodecylsulfate anion took an active part in the reaction, competing with the hydrogen sulfite ion as ring-opening reagent. Reactions were also carried out in Winsor III systems based on alcohol ethoxylate. Compared with the one-phase system, reaction in the Winsor III system was slow, probably due to unfavourable partitioning of the reagents between the middle-phase microemulsion, where the reaction occurs, and the excess oil and water phases. An attempt was made to increase the reaction rate in the Winsor III system by addition of a phase-transfer agent, tetrabutylammonium hydrogen sulfate. The phase transfer agent gave only a marginal accelerating effect, however.
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