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http://dx.doi.org/10.14478/ace.2019.1030

Accelerating Effects of Ultrasonic Irradiation on Reaction Rates for the Asymmetric Ring Opening Reaction of Epoxides  

Lee, Yae Won (Graduate School of Chemistry and Chemical Engineering, Inha University)
Park, Geun Woo (Graduate School of Chemistry and Chemical Engineering, Inha University)
Kim, Geon Joong (Graduate School of Chemistry and Chemical Engineering, Inha University)
Publication Information
Applied Chemistry for Engineering / v.30, no.3, 2019 , pp. 365-370 More about this Journal
Abstract
In this study, effects of the ultrasonic irradiation during the reaction process were investigated for the enantioselective kinetic resolution (EKR) reaction of racemic epoxides in the presence of chiral cobalt salen catalysts, as compared to that of using the conventional mechanical stirring. In order to compare catalytic activities, the chiral cobalt salen complexes having $AlCl_3-$, $BF_3-$ and nitrobenzenesulfonic acid (NBSA) were synthesized and used as catalysts, and then three kinds of the racemic epoxides such as ephichlorohydrine (ECH), epoxy phenoxypropane (EPP) and propylene oxide (PO) were used as reactants. In addition, EKR reactions have been performed using the water and methanol as nucleophiles, respectively. The unique contribution of ultrasonic irradiation as a powerful mixing medium was evaluated in this study to improve the kinetics in comparison to the conventional mechanical agitation during EKR reactions. The reaction time to obtain the highest 99 ee% became shorten more than that of above 60%, when the ultrasonic irradiation was used. This result may be interpreted by the cavitation effect of ultrasound in the solution, generating a powerful shear force for the very violent mixing.
Keywords
Asymmetric ring opening; Chiral epoxide; Ultrasonication; Salen catalyst;
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Times Cited By KSCI : 1  (Citation Analysis)
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