Issue 8, 2022

Green solvent free epoxidation of olefins by a heterogenised hydrazone-dioxidotungsten(vi) coordination compound

Abstract

A new mononuclear tungsten coordination compound, [WO2L(CH3OH)] (1), was synthesized by the reaction of WCl6 and H2L (H2L = (E)-4-amino-N′-(5-bromo-2-hydroxybenzylidene)benzohydrazide) in methanol. Both the H2L and compound 1 were characterized by elemental analysis and UV-Vis, FT-IR and NMR spectroscopic methods. The molecular structure of compound 1 was also determined by single crystal X-ray analysis which confirmed the compound is a mononuclear coordination compound of cis-dioxidotungsten(VI) containing a free amine functionality on the ligand. Compound 1 was supported on propionyl chloride-functionalized silica gel by amidification reaction to obtain a heterogeneous catalyst. The obtained heterogeneous catalyst was characterized by FT-IR spectroscopy, thermal gravimetric analysis (TGA), diffuse-reflectance spectroscopy (DRS), X-ray diffraction analysis (XRD), energy-dispersive X-ray spectroscopy (EDX), X-ray photoelectron spectroscopy (XPS) and scanning electron microscopy (SEM) and its catalytic activity was investigated in the epoxidation of olefins with hydrogen peroxide under solvent free conditions. The catalyst was successfully recovered several times and the recovered catalyst was also characterized by various methods including FT-IR, DRS, TGA, SEM and EDX analyses. The results indicated this heterogeneous catalytic system is an effective and selective catalyst for epoxidation of olefins and can be reused several times without significant change in its catalytic activity.

Graphical abstract: Green solvent free epoxidation of olefins by a heterogenised hydrazone-dioxidotungsten(vi) coordination compound

Supplementary files

Article information

Article type
Paper
Submitted
20 dek 2021
Accepted
27 yan 2022
First published
09 fev 2022
This article is Open Access
Creative Commons BY license

RSC Adv., 2022,12, 4813-4827

Green solvent free epoxidation of olefins by a heterogenised hydrazone-dioxidotungsten(VI) coordination compound

N. Heydari, R. Bikas, M. Shaterian and T. Lis, RSC Adv., 2022, 12, 4813 DOI: 10.1039/D1RA09217K

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