The Immobilized Cu-Ni-Fe-Cr Layered Double Hydroxide on Silica-Layered Magnetite as a Reusable Mesoporous Catalyst for Convenient Conversion of Epoxides to 1,2-Diacetates

: pp. 279 - 287
Faculty of Science and Chemistry, Urmia University
Faculty of Science and Chemistry, Urmia University

In this study, $Cu-Ni-Fe-Cr$ layered double hydroxide (LDH) immobilized on silica layered magnetite $({Fe}_{3}{O}_{4}@{SiO}_{2}@Cu-Ni-Fe-Cr \,  LDH)$ was investigated towards ring opening of diverse epoxides with acetic anhydride to afford vic-diacetates within 15–40 min in high yields. Reusability of the nano-LDH was also studied for 6 consecutive cycles without the significant loss of catalytic activity.

  1. Zeynizadeh, B.; Gilanizadeh, M. Green and Highly Efficient Approach for the Reductive Coupling of Nitroarenes to Azoxya-renes Using the New Mesoporous Fe3O4@SiO2@Co-Zr-Sb Cata-lyst. Res. Chem. Intermed. 2020, 46, 2969-2984.
  2. Zeynizadeh, B.; Gilanizadeh, M. Synthesis and Characterization of a Magnetic Graphene Oxide/Zn-Ni-Fe Layered Double Hydrox-ide Nanocomposite: An Efficient Mesoporous Catalyst for the Green Preparation of Biscoumarins. New J. Chem. 2019, 43, 18794-18804.
  3. Gilanizadeh, M.; Zeynizadeh, B. Synthesis and Characterization of the Immobilized Ni-Zn-Fe Layered Double Hydroxide (LDH) on Silica-Coated Magnetite as a Mesoporous and Magnetically Reusable Catalyst for the Preparation of Benzylidenemalononitriles and Bisdimedones (Tetraketones) under Green Conditions. New J. Chem. 2018, 42, 8553-8566.
  4. Gilanizadeh, M.; Zeynizadeh, B. Binary Copper and Iron Oxides Immobilized on Silica-Layered Magnetite as a New Reusable Heterogeneous Nanostructure Catalyst for the Knoevenagel Condensation in Water. Res. Chem. Intermed. 2018, 44, 6053-6070.
  5. Gilanizadeh, M.; Zeynizadeh, B.; Gholamiyan E. Green Formy-lation of Alcohols Catalyzed by Magnetic Nanoparticles of the Core-Shell Fe3O4@SiO2-SO3H. Iran. J. Sci. Technol. T. A Sci. 2019, 43, 819-827.
  6. Zeynizadeh, B.; Gholamiyan, E.; Gilanizadeh, M. Magnetically Recoverable CuFe2O4 Nanoparticles as an Efficient Heterogeneous Catalyst for Green Formylation of Alcohols. Curr. Chem. Lett. 2018, 7, 121-130.
  7. Gilanizadeh, M.; Zeynizadeh, B. Cascade Synthesis of Fused Polycyclic Dihydropyridines by Ni-Zn-Fe Hydrotalcite (HT) Im-mobilized on Silica-coated Magnetite as Magnetically Reusable Nanocatalyst. Res. Chem. Intermed. 2019, 45, 2811-2825.
  8. [8] Rives, V. Layered Double Hydroxides: Present and Future; Nova Science Publishers: New York, 2001.
  9. Mandal, S.; Mayadevi, S. Adsorption of Fluoride Ions by Zn-Al Layered Double Hydroxides. Appl. Clay Sci. 2008, 40, 54-62.
  10. Goh, K.-H.; Lim, T.-T.; Dong, Z. Application of Layered Double Hydroxides for Removal of Oxyanions: A Review. Water Res. 2008, 42, 1343-1368.
  11. Lee, W.F.; Chen, Y.-C. Effect of Hydrotalcite on the Physical Properties and Drug-release Behavior of Nanocomposite Hydrogels Based on Poly[acrylic Acid-co-poly(ethylene glycol) Methyl ETher Acrylate] Gels. J. Appl. Polym. Sci. 2004, 94, 692-699.
  12. Evans, D.G.; Duan, X. Preparation of Layered Double Hydroxides and their Applications as Additives in Polymers, as Precursors to Magnetic Materials and in Biology and Medicine. ChemComm 2006, 485-496
  13. Chang, Y.-C.; Chang, S.-W.; Chen, D.-H. Magnetic Chitosan Nanoparticles: Studies on Chitosan Binding and Adsorption of Co(II) Ions. React. Funct. Polym. 2006, 66, 335-341.
  14. Abu-Reziq, R.; Alper, H.; Wang, D.; Post, M.L. Metal Supported on Dendronized Magnetic Nanoparticles:  Highly Selective Hydroformylation Catalysts. J. Am. Chem. Soc. 2006, 128, 5279-5282.
  15. Zhang, D.-H.; Li, G.-D.; Li, J.-H.; Chen, J.-S. One-Pot Synthesis of Ag-Fe3O4 Nanocomposite: A Magnetically Recyclable and Efficient Catalyst for Epoxidation of Styrene. ChemComm 2008, 29, 3414-3416.
  16. Gawande, M.B.; Branco, P.S.; Varma, R.S. Nano-Magnetite (Fe3O4) as a Support for Recyclable Catalysts in the Development of Sustainable Methodologies. Chem. Soc. Rev. 2013, 42, 3371-3393.
  17. Shylesh, S.; Schünemann, V.; Thiel, W.R. Magnetically Sepa-rable Nanocatalysts: Bridges between Homogeneous and Heteroge-neous Catalysis. Angew. Chem. Int. Ed. 2010, 49, 3428-3459.
  18. Shokouhimehr, M.; Piao, Y.; Kim J.; Jang, Y.; Hyeon, T. A Magnetically Recyclable Nanocomposite Catalyst for Olefin Epoxi-dation. Angew. Chem. Int. Ed. 2007, 46, 7039-7043.
  19. [Lu, A.-H.; Salabas, E.L.; Schuth, F. Magnetic Nanoparticles: Synthesis, Protection, Functionalization, and Application. Angew. Chem. Int. Ed. 2007, 46, 1222-1244.
  20. Jacobsen, E.; Pfaltz, A.; Yamamoto, H. Comprehensive Asym-metric Catalysis; SpringerVerlag: Berlin Heidelberg, 1999.
  21. Yudin, A. Aziridines and Epoxides in Organic Synthesis; Wi-ley-VCH: Weinheim, 2006.
  22. Ramesh, P.; Niranjan Reddy, V.L.; Venugopal, D.; Subrahmanyam, M.; Venkateswarlu, Y. Zeolite Catalyzed RIng Opening of Epoxides to Acetylated Diols with Acetic Anhydride. Synth. Commun. 2001, 31, 2599-2604.
  23. Azizi, N.; Mirmashhori, B.; Saidi, M.R. Lithium Perchlorate Promoted Highly Regioselective Ring Opening of Epoxides under Solvent-Free Conditions. Catal. Commun. 2007, 8, 2198-2203.
  24. Gilanizadeh, M.; Zeynizadeh, B. 4Å Molecular Sieves Catalyzed Ring-Opening of Epoxides to 1,2-Diacetates with Acetic Anhydride. Curr. Chem. Lett. 2015, 4, 153-158.
  25. Gilanizadeh, M.; Zeynizadeh, B. Heterogeneous Acidic and Eco-Friendly Reagents for Mild and Convenient Conversion of Epoxides to 1,2-Diacetates. J. Chem. Res. 2016, 40, 296-298.
  26. Zeynizadeh, B.; Gilanizadeh, M.; Mohammad Aminzadeh, F. A highly Efficient Protocol for Regioselective Ring-Opening of Epoxides with Alcohols, Water, Acetic Acid, and Acetic Anhydride Catalyzed by SbF3. Phosphorus, Sulfur Silicon Relat. Elem. 2016, 191, 1051-1056.
  27. Moghadam, M.; Mohammadpoor-Baltork, I.; Tangestaninejad, S.; Mirkhani, V.; Shariati, L.; Babaghanbari, M.; Zarea, M. Zirconyl Triflate, [ZrO(OTf)2], as a New and Highly Efficient Catalyst for Ring-Opening of Epoxides. J. Iran. Chem. Soc. 2009, 6, 789-799.
  28. Gilanizadeh, M.; Zeynizadeh, B. Direct Transformation of Epoxides to 1,2-Diacetates with Ac2O/B(OH)3 System. J. Chem. Soc. Pak. 2015, 37, 1234-1238.
  29. Das, B.; Saidi Reddy, V.; Tehseen, F. A Mild, Rapid and Highly Regioselective Ring-Opening of Epoxides and Aziridines with Acetic Anhydride under Solvent-Free Conditions Using Ammonium-12-molybdophosphate. Tetrahedron Lett. 2006, 47, 6865-6868.
  30. Gilanizadeh, M.; Zeynizadeh, B. Facile Conversion of Epox-ides to 1,2-Diacetates with NAOAC 3H2O/AC2O System. Iran. J. Chem. Chem. Eng. 2016, 35, 25-29.
  31. Fogassy, G.; Pinel, C.; Gelbard, G. Solvent-Free Ring Opening Reaction of Epoxides Using Quaternary Ammonium Salts as Catalyst. Catal. Commun. 2009, 10, 557-560.
  32. Fan, R.-H.; Hou, X.-L. Tributylphosphine-Catalyzed Ring-Opening Reaction of Epoxides and Aziridines with Acetic Anhydride. Tetrahedron Lett. 2003, 44, 4411-4413.
  33. Dalpozzo, R.; De Nino, A.; Nardi, M.; Russo, B.; Procopio, A. 1,2-Diacetates by Epoxide Ring Opening Promoted by Erbium(III) Triflate. ARKIVOC 2006, vi, 67-73.
  34. Yadollahi, B.; Kabiri Esfahani, F. Efficient Preparation of vic-Diacetates from Epoxides and Acetic Anhydride in the Presence of Iron(III)-substituted Polyoxometalate as Catalyst. Chem. Lett. 2007, 36, 676-677.
  35.  Taghavi, S.A.; Moghadam, M.; Mohammadpoor-Baltork, I.; Tangestaninejad, S.; Mirkhani, V.; Khosropour, A.R.; Ahmadi, V. Investigation of the Catalytic Activity of an Electron-Deficient Va-nadium(IV) Tetraphenylporphyrin: A New, Highly Efficient and Reusable Catalyst for Ring-Opening of Epoxides. Polyhedron 2011, 30, 2244-2252.
  36. Gilanizadeh, M.; Zeynizadeh, B. Synthesis of Magnetic Fe3O4@SiO2@Cu-Ni-Fe-Cr LDH: An Efficient and Reusable Mesoporous Catalyst for Reduction and One-Pot Reductive-Acetylation of Nitroarenes. J. Iran Chem. Soc. 2018, 15, 2821-2837.
  37. Liu, X.; Ma, Z.; Xing, J.; Liu, H. Preparation and Characteriza-tion of Amino-Silane Modified Superparamagnetic Silica Nanos-pheres. J. Magn. Magn. Mater. 2004, 270, 1-6.
  38. Zhang, Y.; Zeng, G.-M.; Tang, L.; Huang, D.-L.; Jiang, X.-Y.; Chen, Y.-N. A Hydroquinone Biosensor Using Modified Core-Shell Magnetic Nanoparticles Supported on Carbon Paste Electrode. Biosens. Bioelectron. 2007, 22, 2121-2126.
  39. Busetto, C.; Del Piero, G.; Manara, G.; Trifirò, F.; Vaccari A. Catalysts for Low-Temperature Methanol Synthesis. Preparation of Cu-Zn-Al Mixed Oxides via Hydrotalcite-Like Precursors. J. Catal. 1984, 85, 260-266.
  40. Li, G.-Y.; Jiang, Y.-R.; Huang, K.-L.; Ding, P.; Yao, L.-L. Kinetics of Adsorption of Saccharomyces Cerevisiae Mandelated Dehydrogenase on Magnetic Fe3O4-Chitosan Nanoparticles. Colloids Surf. A Physicochem. Eng. Asp. 2008, 320, 11-18.
  41. Lopez, J.A.; González, F.; Bonilla, F.A.; Zambrano, G.; Gómez, M.E. Synthesis and Characterization of Fe3O4 Magnetic Nanofluid. Rev. Latinoam. Metal. Mater. 2010, 30, 60-66.