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Immobilized magnetic copper hydrazone complexes for oxidation of styrene to benzaldehyde by tert-butylhydroxyperoxide: an experimental and theoretical approach

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Abstract

New copper hydrazone complexes [CuL1(OAc)](OAc), and [CuL2(OAc)], (L1and HL2 = Schiff base of benzhydrazide with 2-pyridine and 2-hydroxy 3-methoxy benzaldehyde, respectively) were synthesized. The heterogeneous nanocatalysts were obtained through immobilization of homogenous catalyst on magnetic nanoparticles (Fe3O4@SiO2@CPTMS). Characterization of heterogeneous nanocatalysts was performed by different techniques including FTIR, XRD and SEM. The catalytic behavior of homogenous and heterogeneous nanocatalysts were evaluated for oxidation of olefins. Comparing the catalytic behavior of homogenous and heterogeneous confirm that heterogeneous catalysts were more efficient than homogenous catalysts. Based on results, the function of Fe3O4@SiO2@CPTMS/[CuL1(OAc)](OAc) and Fe3O4@SiO2@CPTMS/[CuL2(OAc)] was notable for oxidation of styrene with 98%, 93% conversion and 81%, 68% selectivity towards benzaldehyde, respectively. By coupling Fe3O4 with hydrazone complexes not only can separate the catalysts from reaction medium easily, but also achieve to higher recyclability (up to four cycles). Moreover, to further assist the experimental studies, a comprehensive theoretical calculations are also performed by using density functional theory (DFT) calculations.

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Acknowledgements

The authors acknowledged the research council of Alzahra University for their financial support.

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  1. Department of Inorganic Chemistry, Faculty of Chemistry, Alzahra University, P.O. Box 1993893973, Tehran, Iran

    Maryam Lashanizadegan, Nasimeh Habibi, Hoda Mirzazadeh & Mina Ghiasi

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Lashanizadegan, M., Habibi, N., Mirzazadeh, H. et al. Immobilized magnetic copper hydrazone complexes for oxidation of styrene to benzaldehyde by tert-butylhydroxyperoxide: an experimental and theoretical approach. Reac Kinet Mech Cat 135, 3223–3242 (2022). https://doi.org/10.1007/s11144-022-02304-9

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