Epoxidation of alkenes with NaIO4 catalyzed by an efficient and reusable natural polymer-supported ruthenium(III) salophen catalyst

M Hatefi Ardakani,Z Pakdin-Parizi,S Saeednia,M Moghadam

doi:10.1007/s13738-015-0774-x

M Hatefi Ardakani, Z Pakdin-Parizi + Show 2 more

Open Access

https://doi.org/10.1007/s13738-015-0774-x

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Abstract

In the present study, preparation, characterization, and catalytic activity of Ru(salophen)Cl supported on chitosan were investigated. The prepared heterogeneous catalyst was characterized by diffuse reflectance UV–vis and FT-IR spectroscopic techniques, scanning electron microscopy, and neutron activation analysis. In this catalytic system, the effects of different solvents were studied in the epoxidation of cis-cyclooctene and CH3CN/H2O was found to be a better solvent. Also, the effects of oxygen donors such as NaIO4, H2O2, H2O2/urea(UHP), tert-BuOOH, NaClO, and Bu4NIO4 were studied in the epoxidation of cis-cyclooctene and NaIO4 was selected as an oxidant. The catalytic activity of this new heterogeneous catalyst in the epoxidation of cyclic and linear alkenes using NaIO4 as an oxidant in CH3CN/H2O at room temperature was studied. The obtained results led us to conclude that [Ru(salophen)Cl@ chitosan] is an efficient catalyst for the epoxidation of alkenes with NaIO4. The catalyst can be readily recovered simply by filtration and reused several times without any significant loss in its catalytic activity.

Highlights

Transition metal Schiff base complexes have been widely used as homogeneous or heterogeneous catalysts in various reactions such as aliphatic and aromatic hydroxylation, olefin epoxidation, and alcohol oxidation [1–27]
Chitosan is produced by N-deacetylation of chitin, which is obtained from crab or shrimp
The present paper describes the preparation, characterization, and catalytic activity of ruthenium(III) salophen supported on chitosan in the epoxidation of alkenes using sodium periodate at room temperature

Summary

Introduction

Transition metal Schiff base complexes have been widely used as homogeneous or heterogeneous catalysts in various reactions such as aliphatic and aromatic hydroxylation, olefin epoxidation, and alcohol oxidation [1–27]. Keywords Ru(III)salophen · Chitosan · Alkene epoxidation · Sodium periodate · Heterogeneous catalyst The present paper describes the preparation, characterization, and catalytic activity of ruthenium(III) salophen supported on chitosan in the epoxidation of alkenes using sodium periodate at room temperature. As far as we know, our study is the first to use chitosan as support for Ru(salophen)Cl complex in heterogeneous catalysis.

Results

Conclusion