تهیه و شناسایی نانوکاتالیست مغناطیسی NiFe2O4/Cu(OH)2و استفاده از آن در سنتز تک ظرفی β-کلرو استات‌ها از اپوکسیدها

عیسوی, روناک

تهیه و شناسایی نانوکاتالیست مغناطیسی NiFe2O4/Cu(OH)2و استفاده از آن در سنتز تک ظرفی β-کلرو استات‌ها از اپوکسیدها

نوع مقاله : مقاله پژوهشی

نویسنده

روناک عیسوی

دانشگاه پیام نور

چکیده

:نانوذرات مغناطیسی فریت نیکل با استفاده از نمک نیترات آهن هیدراته سه ظرفیتی و سولفات نیکل در حضور باز قوی NaOH و نمک NaCl، به روش حالت جامد سنتز و سپس، در دماهای بالا کلسینه شد. برای جلوگیری از اکسید شدن و متراکم شدن و همچنین، بهمنظور افزایش تعداد گروههای عاملی در سطح نانوکاتالیست، نانوذرات NiFe₂O₄با هیدروکسید مس در محیط بازی وارد واکنش شدو نانوچندسازه مغناطیسی NiFe₂O₄/Cu(OH)₂ بهدست آمد. نانوذرات مغناطیسی سنتز شده پس از تأیید ساختار با استفاده از روشهای VSM، FT-IR ،EDS،SEM ، TEM و XRD بهعنوان کاتالیست جدید در تبدیل تک ظرفی و مؤثر اپوکسیدهای مختلف دارای استخلافهای آریلی، آلیلی و آلکیلی به β-کلرو استرهای متناظر در حضور کلرید نیکل و استیک انیدرید در دمای اتاق تحت شرایط بدون حلال مورد استفاده قرار گرفت. سنتز β-کلرو استرها در گسترهی زمانی 32-10دقیقه با بازده 96-80 درصد انجام شد. نانوکاتالیست مغناطیسی با استفاده از یک آهنربای ساده به آسانی از محیط واکنش بازیافت شده و با حفظ ویژگی مغناطیسی و کاتالیزوری در چرخههای متوالی مورد استفاده مجدد قرار گرفت.

کلیدواژه‌ها

اپوکسید

β-کلرو استات

NiFe2O4/Cu(OH)2

نانوکاتالیزور مغناطیسی

بدون حلال

20.1001.1.24235628.1400.8.2.5.6

عنوان مقاله English

Preparation and characterization of NiFe2O4/Cu(OH)2 magnetic nanocatalyst and its use in one-pot synthesis of β-chloroacetates from epoxides

نویسنده English

Ronak Eisavi

Payame Noor University

[1] K. G. Watson, Y. M. Fung, M. Gredley, G. J. Bird, W. R. Jackson, H. Gountzos, B. R. Matthews, “Asymmetric syntheses of (+)-diltiazem hydrochloride,” Journal of the Chemical Society, Chemical Communications, 15, 1018-1019, 1990.

[2] J. Beger, “Präparative aspekte elektrophiler dreikomponentenreaktionen mit alkenen,” Journal für Praktische Chemie, 333, 677–698, 1991.

[3] S. Hamaguchi, T. Ohashi, K. Watanabe, “Lipase-catalyzed stereoselective hydrolysis of 2-acyloxy-3-chloropropyl p-toluenesulfonate,” Agricultural and Biological Chemistry, 50, 375–380, 1986.

[4] R. C. Larock, “Comprehensive organic transformations,” A Guide to functional Group preparations, Wiley-VCH, New York, 1999.

[5] J. R., Williams, J. C., Boehm, “The syntheses of 3β-steroidal diacylglyceryl sulfides,” Sulfoxides, and Sulfones, Steroids, 60, 321–323 1995.

[6] J. Prades, S. S. Funari, P. V. Escriba, F. Barcelo, “Effects of unsaturated fatty acids and triacylglycerols on phosphatidylethanolamine membrane structure,” Journal of Lipid Research, 44, 1720–1727, 2003.

[7] Y. Iwasaki, T. Yamane, “Enzymatic synthesis of structured lipids,” Journal of Molecular Catalysis B: Enzymatic, 10, 129–140, 2000.

[8] T. Ren, D. Liu, “Synthesis of cationic lipids from 1,2,4-butanetriol,” Tetrahedron Letters, 40, 209–212, 1999.

[9] M. Kurz, G. K. E. Scriba, “Drug–phospholipid conjugates as potential prodrugs: Synthesis, characterization, and degradation by pancreatic phospholipase A₂,” Chemistry and Physics of Lipids, 107, 143–157, 2000.

[10] N. Iranpoor, B. Zeynizadeh, “Efficient and regioselective conversion of epoxides into vicinal chloroesters with TiCl₄ and imidazole in ethyl acetate,” Journal of Chemical Research, (S) 582–583, 1998.

[11] S. D. Stamatov, J. Stawinski, “Regioselective and Stereospecific halosilylating cleavage of the oxirane system of glycidol derivatives as an efficient strategy to C2‐O‐functionalized C3‐vicinal halohydrins,” European Journal of Organic Chemistry, 2008, 2635–2643, 2008.

[12] J. F. Costello, J. Lam, N. M. Ratcliffe, S. L. Repetto, “A stereospecific one-pot synthesis of β-chloro esters via the Bicl₃catalysed O-acylative cleavage of crowded epoxides”, Journal of Chemical Research, 39, 324–325, 2015.

[13] J. E. Backvall, M. W. Young, K. B. Sharpless, “Vicinal acetoxychlorination of olefins by chromyl chloride in acetyl chloride,” Tetrahedron Letters, 18, 3523–3526, 1977.

[14] J. Iqbal, M. Amin Khan, R. R. Srivastava, “Cobalt catalysed regioselective cleavage of oxiranes with acylchlorides,” Tetrahedron Letters, 29, 4985–4986, 1988.

[15] I. Shibata, A. Baba, H. Matsuda, “Regioselective ring cleavage of oxiranes catalyzed by organotin halide - triphenylphosphine complex,” Tetrahedron Letters, 27, 3021–3024 1986.

[16] P. Gros, P. Le Perchec, J. P. Senet, “Reaction of epoxides with chlorocarbonylated compounds catalyzed by hexaalkylguanidinium chloride,” Journal of Organic Chemistry, 59, 4925–4930, 1994.

[17] N. Azizi, B. Mirmashhori, M. R. Saidi, “Lithium perchlorate promoted highly regioselective ring opening of epoxides under solvent-free conditions,” Catalysis Communications, 8, 2198–2203, 2007.

[18] S. Bhar, B. C. Ranu, “Zinc-promoted selective cleavage of ethers in presence of acyl chloride,” Journal of Organic Chemistry, 60, 745–747, 1995.

[19] V. Suresh, N. Suryakiran, Y. Venkateswarlu, “A mild and efficient synthesis of chloroesters by the cleavage of cyclic and acyclic ethers using Bi(NO₃)₃·5H₂O as a catalyst under solvent-free conditions,” Canadian Journal of Chemistry, 85, 1037–1040, 2007.

[20] T. Oriyama, A. Ishiwata, Y. Hori, T. Yatabe, N. Hasumi, G. Koga, “Highly regioselective tin-mediated ring-opening of 2,3-epoxy alcohol derivatives with trimethylsilyl halide,” Synlett, 10, 1004–1006, 1995.

[21] G. Aghapour, R. Hatefipour, “Catalyst-free, direct, high regio-and chemoselective conversion of epoxides to vicinal haloesters under mild, neutral, and solvent-free conditions,” Synthetic Communications, 43, 1030–1040, 2013.

[22] M. T. Maghsoodlou, R. Heydari, F. Mohamadpour, “Fe₂O₃ as an environmentally benign natural catalyst for one-pot and solvent-free synthesis of spiro-4H-pyran derivatives,” Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 36, 31–38, 2017.

[23] A. K. Gupta, M. Gupta, “Synthesis and surface engineering of iron oxide nanoparticles for biomedical applications,” Biomaterials, 26, 3995–4021, 2005.

[24] Q. A. Pankhurst, J. Connolly, S. K. Jones, J. Dobson, “Applications of magnetic nanoparticles in biomedicine,” J. Physics. D: Applied. Physics, 36, R167–181, 2003.

[25] T. Neuberger, B. Schöpf, H. Hofmann, M. Hofmann, B. Rechenberg, “Superparamagnetic nanoparticles for biomedical applications: possibilities and limitations of a new drug delivery system,” Journal of Magnetism and Magnetic Materials, 293, 483–496, 2005.

[26] D. L. Graham, H. A. Ferreira, P. P. Freitas, “Magnetoresistive-based biosensors and biochips,” Trends Biotechnol., 22, 455–462, 2004.

[27] A.‐H. Lu, E. L. Salabas, F. Schüth, “Magnetic nanoparticles: synthesis, protection, functionalization, and application,” Angewandte Chemie International Edition, 46, 1222–1244, 2007.

[28] S. Shylesh, V. Schünemann, W. R. Thiel, “Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis,” Angewandte Chemie International Edition in English, 49, 3428–3459, 2010.

[29] V. Polshettiwar, R. S. Varma, “Green chemistry by nano-catalysis,” Green Chemistry, 12, 743–754, 2010.

[30] R. Eisavi, S. Ghadernejad, B. Zeynizadeh, F. Mohammad Aminzadeh, “Magnetically separable nano CuFe₂O₄: an efficient and reusable heterogeneous catalyst for the green synthesis of thiiranes from epoxides with thiourea,” Journal of Sulfur Chemistry, 37, 537–545, 2016.

[31] R. Eisavi, F. Ahmadi, B. Ebadzade, S. Ghadernejad, “A green method for solvent-free conversion of epoxides to thiiranes using NH₄SCN in the presence of NiFe₂O₄ and MgFe₂O₄ magnetic nanocatalysts,” Journal of Sulfur Chemistry, 38, 614, 2017.

[32] S. Hassanzadeh, R. Eisavi, M. Abbasian, “Preparation and characterization of magnetically separable MgFe₂O₄/Mg(OH)₂ nanocomposite as an efficient heterogeneous catalyst for regioselective one‐pot synthesis of β‐chloroacetates from epoxides,” Applied Organometallic Chemistry, 32, e4520, 2018.

[33] R. Eisavi, S. Alifam, “ZnFe₂O₄ nanoparticles: a green and recyclable magnetic catalyst for fast and regioselective conversion of epoxides to vicinal hydroxythiocyanates using NH₄SCN under solvent-free conditions,” Phosphorus, Sulfur, and Silicon and the Related Elements, 193, 211–217, 2017.

[34] S. Hassanzadeh, R. Eisavi, M. Abbasian, “Green synthesis of thiiranes from epoxides catalyzed by magnetically separable CuFe₂O₄/Mg(OH)₂ nanocomposite in water under benign conditions,” Journal of Sulfur Chemistry, 40, 240-255, 2019.

[35] R. Eisavi, A. Karimi, “CoFe₂O₄/Cu(OH)₂ magnetic nanocomposite: an efficient and reusable heterogeneous catalyst for one-pot synthesis of b-hydroxy-1,4-disubstituted- 1,2,3-triazoles from epoxides,” RSC Advances, 9, 29873–29887, 2019.

[36] B. Xu, S. Senthilkumar, W. Zhong, Z. Shen, C. Lu, X. Liu, “Magnetic core–shell Fe₃O₄@Cu₂O and Fe₃O₄@Cu₂O–Cu materials as catalysts for aerobic oxidation of benzylic alcohols assisted by TEMPO and N-methylimidazole,” RSC Advances, 10, 26142-26150, 2020.

[37] B. Zeynizadeh, S. Rahmani, H. Tizhoush, “The immobilized Cu nanoparticles on magnetic montmorillonite (MMT@Fe₃O₄@Cu): As an efficient and reusable nanocatalyst for reduction and reductive-acetylation of nitroarenes with NaBH₄,” Polyhedron, 175, 114201-111424, 2020.

[38] H. Zheng, J. Huang, T. Zhou, Y. Jiang, Y. Jiang, M. Gao, Y. Liu, “Recyclable magnetic Cu/CuFe₂O₄ nanocomposites for the rapid degradation of 4-NP, ” Catalysts, 10, 1437-1447 2020.

[39] Z. P. Sun, L. Liu, D.Z. Jia, W. Pan, “Simple synthesis of CuFe₂O₄ nanoparticles as gas-sensing materials,” Sensors and Actuators B: Chemical, 125, 144-148, 2007.

[40] M. Gharagozlou, “Influence of calcination temperature on structural and magnetic properties of nanocomposites formed by Co-ferrite dispersed in sol-gel silica matrix using tetrakis(2-hydroxyethyl) orthosilicate as precursor,” Chemistry Central Journal, 5, 1-7, 2011.

[41] L. Wang, K. Zhang, Z. Hu, W. Duan, F. Cheng, J. Chen, “Porous CuO Nanowires as the Anode of Rechargeable Na-ion Batteries,” Nano Res.,7, 199-208, 2014.