نمک مغناطیسی روی هیدروژن فسفو تنگستیک اسید: یک کاتالیزور کارآمد برای سنتز تک ظرف مشتقات H4-پیران ها

نوع مقاله : مقاله علمی پژوهشی

نویسندگان

1 گروه شیمی-دانشکده علوم پایه-دانشگاه شهرکرد - شهرکرد- ایران

2 گروه شیمی-دانشکده علوم پایه- دانشگاه شهرکرد- شهرکرد- ایران

3 گروه شیمی دانشکده علوم پایه دانشگاه شهرکرد شهرکرد ایران

چکیده

چکیده
در این تحقیق، کاتالیزگر مغناطیسی نمک روی هیدروژن فسفوتنگستیک اسید (ZnHPMo12O40) با جایگزینی پروتو‌‌ن‌ها در H3PW12O40 با کاتیون‌های فلز روی به-عنوان یک کاتالیزگر قابل بازیافت سنتز شد. ساختار و بافت کاتالیزگر سنتز شده با استفاده از طیف‌سنجی مادون قرمز تبدیل فوریه (FT-IR)، تجزیه و تحلیل حرارت سنجی (TGA)، آنالیز سطح BETمیکروسکوپ الکترونی روبشی (SEM) و آنالیز مغناطیس سنجی ارتعاشی (VSM) شناسایی شد. این کاتالیزگر مؤثر و قابل بازیافت با موفقیت برای سنتز H4-پیران‌ها استفاده شد. نتایج نشان داد که کاتالیزگر مغناطیسی روی هیدروژن فسفوتنگستیک اسید فعالیت کاتالیزی خوبی داشته و فرآورده‌های مورد نظر با بازده خوب تا عالی به-دست آمدند. فعالیت خوب کاتالیزگر نمک هتروپلی اسید در ارتباط نزدیک با سطح ویژه بالا و هم‌افزایی خصلت برونستد و لویس اسیدی آن می‌باشد. کاتالیزگر پایداری خوبی داشته و می‌توان آن را شش بار بدون کاهش چشمگیری در فعالیت در واکنش استفاده کرد.

کلیدواژه‌ها

موضوعات


عنوان مقاله [English]

Magnetic Zinc hydrogen salt of phosphotungstic acid: an efficient catalyst for the one-pot synthesis of 4-H pyrans derivatives

نویسندگان [English]

  • Mahdieh Sajadi 1
  • Ahmad Reza Momeni 2
  • Heshmatallah Samimi 3
1 Department of Chemistry, Faclty of Science. Shahrekord University, Shahrekord, Iran
2 Department of chemistry, Faculty of science, Shahrekord University, Shahrekord, Iran
3 Department of Chemistry, Faculty of Scinces, Shahrekord University, shahrekord, Iran
چکیده [English]

Abstract
In this study, a magnetic catalyst of phosphutangetic acid salt (ZnHPMo12O40) was prepared by substitution of protons in H3PW12O40 with zinc metal cations as a recyclable catalyst. The structural and morphology of the prepared catalysts was investigated using Fourier transform infrared spectroscopy (FT-IR), differential thermal gravimetric analysis (TGA), BET surface analysis emission scanning electron microscopy (SEM) and vibrating sample magnetometry (VSM). The prepared catalyst was successfully used as an efficient and recyclable catalyst for the synthesis of 4H-pyrans. The results showed that the magnetic zinc phosphotangestic acid catalyst exhibited good catalytic activity under optimum reaction conditions and the desired products were obtained in good to excellent yields. The good activity of the zinc salt of heteropoly acid catalyst was closely related to its high specific surface area, and the synergistic effects of Lewis and Brønsted acidity. The catalyst stability was good and it can be reused six times without significant loss activity in reaction.

کلیدواژه‌ها [English]

  • Keywords: 4H-pyrans
  • zinc hydrogen phosphutangetic acid salt
  • magnetic catalyst
  • heteropoly acid

This is an open access article under the CC-BY-SA 4.0 license.( https://creativecommons.org/licenses/by-sa/4.0/)

[1] Kozhevnikov, I.V. (1995). Heteropoly acids and related compounds as catalysts for fine chemical synthesis. Catalysis Reviews - Science and Engineering, 37(2), 311-352.
[2] Maksimov, G.M. (1995). Advances in the synthesis of polyoxometalates and in the study of heteropolyacids. Russian Chemical Reviews,  64(5),  445-462.
[3]  Tran, Q. V., Truong, T. H., Hung, T. Q., Doan, H. V., Pham, X. N., Le, N. T. H., & Nguyen, V. T. (2020). Preparation and testing of ceasium Brønsted ion-exchanged Al-SBA-15 supported heteropoly acid as heterogeneous catalyst in the fructone fragrancy synthesis. Journal of Porous Materials, 27(5), 1745-1754.
[4] Nikseresht, A., & Aderang, E. (2021). Encapsulation of phosphotungstic acid in the nanostructure of metal-organic framework as a heterogonous catalyst used for Fries rearrangement of O-acyloxy benzenes in para-situation. Applied Chemistry, 16(61), 25-38. (in persion)
[5] Mojaverian Kermani, A., Ahmadpour, A., & Rohani Bastami, T. (2021). Synthesis of Dawson Hetero-Polyoxometalate/Activated Carbon Composite and evaluation of its catalytic application for Oxidative removal of Dibenzothiophene. Applied Chemistry, 16(60), 63-78. (in persion)
[6] Taghdiri, M., & Dadari Doolabi, S. (2023). Modification of Magnetic Activated Carbon Nanoparticles with Phosphotungstate for Photocatalytic Application under Sunlight, and Visible, Irradiation. Applied Chemistry, 18(66), 45-62. (in persion)
[7] Popa, A., Sasca, V., Bajuk-Bogdanović, D., & Holclajtner-Antunović, I. (2016). Acidic nickel salts of Keggin type heteropolyacids supported on SBA-15 mesoporous silica. Journal of Porous Materials, 23(1), 211-223.
[8] Kefayati, H., Tajalirad, F., & Shariati, S. (2022). Functionalization of Fe3O4 nanoparticles with propylaminopyridine and its use as an efficient catalyst in the synthesis of novel 4, 8-dihydro-1H-pyrimido [1, 2-a] pyrimidines. Applied Chemistry17(63), 123-134. (in persion)
[9] Cheng, T., Zhang, D., Li, H., & Liu, G. (2014). Magnetically recoverable nanoparticles as efficient catalysts for organic transformations in aqueous medium. Green Chemistry16(7), 3401-3427.
[10] Hudson, R., Feng, Y., Varma, R. S., & Moores, A. (2014). Bare magnetic nanoparticles: sustainable synthesis and applications in catalytic organic transformations. Green Chemistry,16(10), 4493-4505.
[11] Safari, J., & Zarnegar, Z. (2013). A magnetic nanoparticle-supported sulfuric acid as a highly efficient and reusable catalyst for rapid synthesis of amidoalkyl naphthols. Journal of Molecular Catalysis A: Chemical, 379, 269-276.
[12] Perrella, F. W., Chen, S. F., Behrens, D. L., Kaltenbach, R. F. I., & Seitz, S. P. (1994). Phospholipase C inhibitors: a new class of agents. Journal of Medicinal Chemistry, 37(14), 2232-2237.
[13] Schiller, R., Tichotová, L., Pavlík, J., Buchta, V., Melichar, B., Votruba, I., & Pour, M. (2010). 3, 5-Disubstituted pyranone analogues of highly antifungally active furanones: conversion of biological effect from antifungal to cytostatic. Bioorganic & Medicinal Chemistry, 20(24), 7358-7360.
[14] Bisht, S. S., Jaiswal, N., Sharma, A., Fatima, S., Sharma, R., Rahuja, N., & Tripathi, R. P. (2011). A convenient synthesis of novel pyranosyl homo-C-nucleosides and their antidiabetic activities. Carbohydrate Research346(10), 1191-1201.
[15] Ebrahimipour, S. Y., Khosravan, M., Castro, J., Nejad, F. K., Dusek, M., & Eigner, V. (2018). Synthesis and structure elucidation of a novel mixed-ligand Cu (II) Schiff base complex and its catalytic performance for the synthesis of 2-amino-4H-pyrans and tetrahydro-4H-chromenes. Polyhedron146, 73-80.
[16] Bihani, M., Bora, P. P., Bez, G., & Askari, H. (2013). Amberlyst A21: A reusable solid catalyst for green synthesis of pyran annulated heterocycles at room temperature. Comptes Rendus Chimie,16(5), 419-426.
[17] Maleki, B., Reiser, O., Esmaeilnezhad, E., & Choi, H. J. (2019). SO3H-dendrimer functionalized magnetic nanoparticles (Fe3O4@ DNH (CH2)4SO3H): Synthesis, characterization and its application as a novel and heterogeneous catalyst for the one-pot synthesis of polyfunctionalized pyrans and polyhydroquinolines. Polyhedron162, 129-141.
[18] Kharbangar, I., Rohman, M. R., Mecadon, H., & Myrboh, B. (2012). KF-Al2O3 as an Efficient and Recyclable Basic Catalyst for the Synthesis of 4H-Pyran-3-carboxylates and 5-Acetyl-4H-pyrans. Int. Journal of Organic Chemistry, 2(3), 282.
[19] Rakhtshah, J., Salehzadeh, S., Zolfigol, M. A., & Baghery, S. (2017). Mn (III)–pentadentate Schiff base complex supported on multi‐walled carbon nanotubes as a green, mild and heterogeneous catalyst for the synthesis of tetrahydrobenzo [b] pyrans via tandem Knoevenagel–Michael cyclocondensation reaction. Applied organometallic chemistry, 31(9), e3690.
[20] Heravi, M. M., Mirzaei, M., Beheshtiha, S. Y. S., Zadsirjan, V., Mashayekh Ameli, F., & Bazargan, M. (2018). H5BW12O40 as a green and efficient homogeneous but recyclable catalyst in the synthesis of 4H‐Pyrans via multicomponent reaction. Applied organometallic chemistry, 32(9), e4479.
[21] Honarmand, M., Tzani, A., & Detsi, A. (2019). Synthesis of novel multi-OH functionalized ionic liquid and its application as dual catalyst-solvent for the one-pot synthesis 4H-pyrans. Journal of molecular liquids, 290, 111358.
[22] Balaji, S., Guda, R., Mandal, B. K., Kasula, M., Ubba, E., & Khan, F. R. N. (2021). Green synthesis of nano-titania (TiO2 NPs) utilizing aqueous Eucalyptus globulus leaf extract: applications in the synthesis of 4 H-pyran derivatives. Research on Chemical Intermediates, 47, 3919-3931.
[23] Khoshdel, M. A., Shirini, F., Langarudi, M. S. N., Zabihzadeh, M., & Biglari, M. (2021). Three-component synthesis of 4 H-pyran scaffolds accelerated by a gabapentin-based natural deep eutectic solvent. New Journal of Chemistry, 45(6), 3138-3149.
[24] Shabani, N., Heravi, M. R. P., Babazadeh, M., Ghasemi, E., Amini, M., & Robertson, C. (2022). 2-Aminoisoindoline-1, 3-Dione-Functionalized Fe3O4/Chloro-Silane Core-Shell Nanoparticles as Reusable Catalyst: An Efficient Heterogeneous Magnetic Nanoparticles for Synthesis of 4 H-Pyran Derivatives through Multicomponent Reaction. Polycyclic Aromatic Compounds, 42(7), 4561-4577.
[25] Heravi, M. R. P., Aghamohammadi, P., & Vessally, E. (2022). Green synthesis and antibacterial, antifungal activities of 4H-pyran, tetrahydro-4H-chromenes and spiro2-oxindole derivatives by highly efficient Fe3O4@ SiO2@ NH2@ Pd (OCOCH3)2 nanocatalyst. Journal of Molecular Structure, 1249, 131534.
[26] Zeng, Q., Huang, X., Liu, M., Yu, Z., & Xiao, Y. (2022). Synthesis of Trifluoromethylated 4 H-Pyran and 4 H-Thiopyran via Divergent Reaction of β-CF3-1, 3-Enynes with β-Ketothioamides. Organic Letters, 24(44), 8186-8191.
[27] Maleki, R., Koukabi, N., & Kolvari, E. (2018). Fe3O4‐Methylene diphenyl diisocyanate‐guanidine (Fe3O4–4, 4′‐MDI‐Gn): A novel superparamagnetic powerful basic and recyclable nanocatalyst as an efficient heterogeneous catalyst for the Knoevenagel condensation and tandem Knoevenagel‐Michael‐cyclocondensation reactions. Applied organometallic chemistry, 32(1), e3905.
[28] Pizzio, L. R., & Blanco, M. N. (2003). Isoamyl acetate production catalyzed by H3PW12O40 on their partially substituted Cs or K salts. Applied Catalysis A: General, 255(2), 265-277.
[29] Alharbi, K., Alharbi, W., Kozhevnikova, E. F., & Kozhevnikov, I. V. (2016). Deoxygenation of ethers and esters over bifunctional Pt–heteropoly acid catalyst in the gas phase. ACS catalysis, 6(3), 2067-2075.