Use of functionalized superparamagnetic nanoparticles with Thiourea as heterogeneous catalysts in Petasis-Borono Mannich reaction

Ebrahimi Yazdanabdad, Tahereh; Forghaniha, Ali; Emtyazjoo, Mozhgan; Ramezani, Majid

Use of functionalized superparamagnetic nanoparticles with Thiourea as heterogeneous catalysts in Petasis-Borono Mannich reaction

Document Type : Original Research

Authors

T. Ebrahimi Yazdanabdad ¹

A. Forghaniha ¹

M. Emtyazjoo ²

M. Ramezani ¹

¹ Department of Chemistry, Faculty of Sciences, Arak Branch, Islamic Azad University, Arak, Iran.

² Department of Marine Biology, North Tehran Branch, Islamic Azad University, Tehran, Iran.

Abstract

Research Subject: In this study, Thiourea-functionalized super-paramagnetic nanoparticles were used as a heterogeneous catalyst in the Petasis-Borono Mannich reaction.

Research approach: In the first stage of this study, Fe₃O₄@SiO₂ nanoparticles were synthesized as spherical core-shell nanoparticles such that Fe₃O₄ particles were considered as the core. Then in the next step, the characteristics of surface functional groups, crystal structure, magnetic properties, size and surface appearance of nanoparticles and the process of functionalizing the structure in layers, using infrared spectroscopy (FT-IR), X-ray diffraction (XRD), vibrating sample magnetometer (VSM), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) were examined, identified and analyzed. Then, to evaluate the efficiency of the structure, it was used as a catalyst in the Borono-Mannich reaction of potassium potash. Infrared spectroscopy (FT-IR) and hydrogen nuclear magnetic resonance spectroscopy (HNMR) were used to investigate the structure of the products.

Main results: The IR spectroscopy results showed that the peaks appearing in 568 cm^-1 and 670 cm^-1 were related to iron-oxygen bond, the peaks in 1092 and 800-950 cm^-1 were related to silicon-oxygen bond, which indicates the formation of silicon layer on nanomagnetic particles and the validity of the reaction products. The results also showed that the amount of saturated magnetite in about 23 emu/g increased with increasing complex ligand. X-ray diffraction analysis showed that the index peaks of (2θ= 21.25˚, 37.29˚, 43.73˚, 52.56˚, 65.09˚, 69.73˚, 76.81˚) were realized and for certainty of the formation of the desired magnetic nanoparticles in crystalline phase were used. The results of SEM analysis showed the structure of nanoparticles in a spherical shape and EDX analysis confirmed the presence of elements in the structure which included sulfur. Also, the thermogravimetric analysis index showed approximately 7% decomposition coefficient. The first, second and third decomposition were observed 1% by weight (60°C), 5% by weight (200 to 300°C) and 1% by weight (350 to 700° C), respectively. The highest yield of 68% was measured with 40 mg catalyst in acetonitrile. The structure of thiourea was properly stabilized in a magnetic nanocatalyst.

Keywords

Petasis-Borono Mannich reaction

Fe3O4 particles

Thiourea

superparamagnetic nanoparticles

organocatalysts

Subjects

nano-catalyst

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