Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Fabrication of a New Magnetic Zeolite-Y Nanocatalyst Functionalized with N-methylimidazolium chloride Ionic Liquid and Its Application in the Three-Component and Green Synthesis of 2-amino-4H-benzo- and Naphtho- pyrans

Document Type : Research Article

Authors
Department of Chemistry, Faculty of Basic Sciences, Payam Noor University, Tehran, Iran
Abstract
In this research, at first, nanoporous zeolite-NaY was functionalized through reaction with 3-chloropropyltriethoxysilane (organic linker) and then with N-methylimidazole group. Then magnetic nanoparticles (Fe3O4) were formed and stabilized under ultrasonic energy conditions on the surface and internal pores of zeolite-Y (1-MeIm IL@ZY-Fe3O4). The structure of zeolite-ionic liquid prepared as a magnetic nanohybrid using the techniques of FTIR, FESEM, EDS, TGA, BET, XRD and VSM instrumental analyses were identified and confirmed. At the next step, its catalytic performance in the synthesis of a number of 4-aryl-2-amino benzopyran (chromene) or 4-aryl-2-amino naphthopyran (benzochromene) derivatives was investigated through the three-component condensation reaction of aromatic aldehydes, malononitrile and dimedone or β-naphthol, at ambient temperature and aqueous medium. The advantages of this method include the use of cheap, safe and reusable nanocatalyst, easy separation of the heterogeneous catalyst from the reaction medium with the using of a magnet, short reaction time, high yield, easy and fast separation of the product, and the use of non-toxic water solvent, that has made this method in simplicity, be in the scope of "green chemistry". 
Keywords

Subjects


[1] Lu J., Toy P.H., Organic Polymer Supports for Synthesis and for Reagent and Catalyst Immobilization. Chem. Rev., 109(2): 815-838 (2009).
[3] Moshoeshoe M., Nadiye-Tabbiruka M.S., Obuseng V., A Review of the Chemistry, Structure, Properties and Applications of Zeolites. Am. J. Mater. Sci. 7: 196-221 (2017).
[4] Liang J., Liang Z., Zou R., Zhao Y., Heterogeneous Catalysis in Zeolites, Mesoporous Silica, and Metal–Organic Frameworks. Adv. Mater. 29: 1701139 (2017).
[5] Li Y., Li L., Yu J., Applications of Zeolites in Sustainable Chemistry. Chem. 3: 928-949 (2017).
[8] زهرا سیدزاده.، مهدی کلهر.، سید احمد میرشکرایی.، قاسم رضانژاد.، نانو زئولیت-Y عامل دار شده با یون­ های سولفونیک اسید و کلسیم: ساخت و بررسی عملکرد کاتالیستی آن در سنتز چهارجزئی مشتق­ های بنزایمیدازولو پیریمیدو پیریمیدین­ ها، نشریه شیمی و مهندسی شیمی ایران، 41(4): ۱-۱۲ (۱401).
[14] Kalhor M., Banibairami S., Mirshokraie S.A., Ni@zeolite-Y Nanoporous; a Valuable and Efficient Nanocatalyst for the Synthesis of N-Benzimidazole-1,3-Thiazolidinones. Green Chem. Lett. Rev. 11: 334-344 (2018).
[18] Song H., Li R., Jin F., Li Z., Chen J., Efficient and Reusable Zeolite-immobilized Acidic Ionic Liquids for the Synthesis of Polyoxymethylene Dimethyl Ethers. Mol. Catal., 455: 179-187 (2018).
[21] Rossi L.M., Costa N.J., Silva F.P., Wojcieszak R., Magnetic Nanomaterials in Catalysis: Advanced Catalysts for Magnetic Separation and Beyond. Green Chem., 16: 2906-2933 (2014).
[22] Neuberger T., Schöpf B., Hofmann H., Hofmann M., Von Rechenberg B., Superparamagnetic Nanoparticles for Biomedical Applications: Possibilities and Limitations of a New Drug Delivery System. J. Magn. Magn. Mater., 293(1): 483-496 (2005).
[23] رضا علیزاده.، سوده عابدینی.، غلامرضا نبی بیدهندی.، قاسم عموعابدینی.، حذف فلز سرب از پساب صنایع باتری‌سازی با استفاده از نانوذرات مغناطیسی آهن، نشریه شیمی و مهندسی شیمی ایران، 30(1): 71-77 (۱390).
[25] Pankhurst Q.A., Connolly J., Jones S.K., Dobson J., Applications of Magnetic Nanoparticles in Biomedicine. Journal of Physics D: Applied Physics, 36: R167 (2003).
[26] Lim C.W., Lee I.S., Magnetically Recyclable Nanocatalyst Systems for the Organic Reactions. Nano Today, 5: 412-434 (2010).
[29] Ellis G.P., The Chemistry of Heterocyclic Compounds in Chromenes, Chromanes, and Chromones. ed. by A. Weissberger, EC Taylor (1977).
[31] Gourdeau H., Leblond L., Hamelin B., Desputeau C., Dong K., Kianicka I., Custeau D., Bourdeau C., Geerts L., Cai S.X., Drewe J., Labrecque D., Kasibhatla S., Tseng B., Antivascular and Antitumor Evaluation of 2-Amino-4-(3-Bromo-4,5-Dimethoxy-Phenyl)-3-Cyano-4H-Chromenes, a Novel Series of Anticancer Agents. Mol. Cancer Ther., 3: 1375-1383 (2004).
[33] Yang F., Wang H., Jiang L., Yue H., Zhang H., Wang Z., Wang L., A Green and One-pot Synthesis of Benzo[g]chromene Derivatives Through a Multi-component Reaction Catalyzed by Lipase. RSC Advances, 5: 5213-5216 (2015).
[36] Sharghi H., Razavi S.F., Aberi M., Sabzalizadeh F., Karbalaei-Heidari H.R., Nanostructured Coumarin-Based Cobalt Complex as an Efficient, Heterogeneous and Recyclable Catalyst for the Three-Component Synthesis of Benzo [b] Pyran and 3, 4-dihydropyrano [c] Chromene Derivatives. Journal of the Iranian Chemical Society, 18: 1-15 (2021).
[37] Muhammad S., Ali F. I., Javed M.N., Wasim A.A., Bari A., Rafique F., Hashmi I. A., Effect of Supramolecular Polymeric Aggregation in Room Temperature Ionic Liquids (RTILs) on Catalytic Activity in the Synthesis of 4H-chromene Derivatives and Knoevenagel Condensation. Journal of Molecular Liquids, 322: 114503 (2020).
[38] مسعود مختاری.، محمد نیک پسند.، سنتز تک ظرفی تتراهیدروکرومنوکرومن دی اون­ها با استفاده از 3-کربوکسی -1-سولفوپیریدینیوم کلرید به عنوان کاتالیست. نشریه شیمی و مهندسی شیمی ایران، 38(2): 69-76 (1398).
[39] Azizi Amiri M., Firouzzadeh P.G., Tajbakhsh M., Asghari, S., Copper-amine Complex Immobilized on Nano NaY Zeolite as a Recyclable Nanocatalyst for the Environmentally Friendly Synthesis of 2-Amino-4H-Chromenes. Appl. Organomet. Chem., 36: E6886 (2022).
[40] Mobinikhaledi A., Ahadi N., Haseli M., The Use of MnCoFe2O4@GT@Cu Magnetic Nanoparticles in the Synthesis of Benzopyrans. Org. Prep. Proced. Int., 54: 465-472 (2022).
[41] Kalhor M., Bigdeli M., Mirshokraie S.A., Moghanian H., ZnO@zeolite-Y Mesoporous as an Eco-friendly and Efficient Nanocatalyst in the Three-Component Synthesis of 2-Amino-Benzochromenes. Org. Chem. Res., 6: 219-232 (2020).
[42] Perez-Pariente J., Martens J.A., Jacobs P.A., Crystallization Mechanism of Zeolite Beta from (TEA)2O, Na2O and K2O Containing Aluminosilicate Gels. Appl. Catal. 31: 35-64 (1987).
[43] Endang P.S., Rahadian A.R., Ulva T.I.M., Alvin R.W., Rendy M.I., Nurul W., The MnO2/Zeolite NaY Catalyzed Oxidation of CO Emission in Catalytic Converter System. Mater. Sci. Forum. 964: 199-208 (2019).
[44] Xu H., Tong N., Cui L., Lu Y., Gu H., Preparation of Hydrophilic Magnetic Nanospheres with high Saturation Magnetization. Journal of Magnetism and Magnetic Materials, 311: 125-130 (2007).
[45] Shirini F., Abedini M., Zarrabzadeh S., Seddighi M., Efficient Synthesis of 4H-Pyran Derivatives Using a Polymeric Catalyst Based on PVP. J. Iran. Chem. Soc. 12: 2105–2113 (2015).
[48] متین اسدی.، سپیده احسانی فر.، مسعود مختاری.،  سنتز تک ظرف مشتقات تتراهیدرو[b] پیران و پیرانوپیرازول­ها با استفاده از آمونیوم فلوئورید، نشریه شیمی و مهندسی شیمی ایران، 38(2): ۱۰۶-۹۷ (1398).