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Olefin epoxidation with tert-butyl hydroperoxide catalyzed by functionalized polymer-supported copper(II) Schiff base complex

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Abstract

A new polymer-supported Cu(II) Schiff base complex has been synthesized and characterized by elemental (including metal) analysis, FT-IR spectroscopy, UV–Vis diffuse reflectance spectroscopy, thermogravimetric analysis, and scanning electron microscopy. The catalytic performance of this complex was evaluated in the epoxidation of styrene in acetonitrile/N,N-dimethylformamide (9:1) mixture with 70% tert-butyl hydroperoxide as an oxidizing agent under liquid phase reaction conditions for selective synthesis of styrene oxide. Suitable reaction conditions have been optimized by considering the effects of various reaction parameters such as temperature, reaction time, solvent, oxidant, catalyst amount, and styrene to hydroperoxide molar ratio for the maximum conversion of styrene as well as selectivity of styrene oxide. We have also investigated the epoxidation reaction of various olefins under the optimized reaction conditions. Comparison between catalytic activities of the polymer-supported Cu(II) Schiff base complex and its homogeneous analogue showed that the polymer-supported catalyst was more active. This heterogeneous complex was reused for five times. The selectivity of the heterogeneous catalyst does not change even after five times of reusing.

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Acknowledgments

S.M.I. acknowledges the Department of Science and Technology (DST), Council of Scientific and Industrial Research (CSIR), and University Grant Commission (UGC), New Delhi, India for funding.

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Authors and Affiliations

  1. Department of Chemistry, University of Kalyani, Kalyani, Nadia, 741235, WB, India

    Sk Manirul Islam, Anupam Singha Roy, Paramita Mondal, Manir Mobarok, Brindaban Roy, Noor Salam, Sumantra Paul & Sanchita Mondal

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  1. Sk Manirul Islam
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  2. Anupam Singha Roy
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Correspondence to Sk Manirul Islam.

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Islam, S.M., Roy, A.S., Mondal, P. et al. Olefin epoxidation with tert-butyl hydroperoxide catalyzed by functionalized polymer-supported copper(II) Schiff base complex. Monatsh Chem 143, 815–823 (2012). https://doi.org/10.1007/s00706-011-0641-0

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