Supported Ionic Liquid on Silica Gel: A Novel Heterogeneous Catalyst for the Synthesis of α,β-Unsaturated Compounds

Document Type : Research Article

Author

Department of Chemical Engineering, Birjand University of Technology, Birjand, I.R. IRAN

Abstract

In this study, supported tris(hydroxymethyl)methane ammonium acetate ionic liquid on silica gel (SiO2-THMAA) was synthesized for the first time. SiO2-THMAA was prepared by the reaction of 3-chloropropylsilica with  tris(hydroxymethyl) aminomethane followed by ion exchange with acetate. SiO2-THMAA was characterized by FT-IR, BET, and elemental analysis. Also, to explore the catalytic activity of SiO2-THMAA in organic reactions, the synthesis of α,β-unsaturated compounds was investigated in the presence of SiO2-THMAA as a heterogeneous catalyst at room temperature. The desired products were produced in high yields and short times in mild reaction conditions. SiO2-THMAA was also recovered and reused after the three reaction cycle without a significant decrease in catalytic activity.

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References

[1] صحرایی، وهاب؛ قطبی، سیروس؛ تقی خانی، وحید؛ نظری، خداداد، بررسی ضریب فعالیت محلول‌های الکترولیتی و ضریب اسمزی مایع یونی ]4[BMIM][BF با استفاده از معادله حالتSAFT-MSA GV-، نشریه شیمی و مهندسی شیمی ایران، 31(1): 45 تا 54 (1391).
[2] Sheldon R., Catalytic Reactions in Ionic Liquids, Chem. Commun., 23: 2399-2407 (2001).
[3] Welton T., Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis, Chem. Rev., 99(8): 2071-2084 (1999).
[4] Seddon K.R., Ionic Liquids for Clean Technology, J. Chem. Tech. Biotech., 68(4): 351-356 (1997).
[5] Zhao D., Liao Y., Zhang Z., Toxicity of Ionic Liquids, Clean, 35(1): 42-48 (2007).
[6] Jiang W., Zheng D., Xun S., Qin Y., Lu Q., Zhu W., Li H., Polyoxometalate-Based Ionic Liquid Supported on Graphite Carbon Induced Solvent-Free Ultra-Deep Oxidative Desulfurization
of Model Fuels, Fuel, 190: 1-9 (2017).
[7] Isaad J., Achari A., Synthesis and Spectroscopic Characterization of Azoic Dyes Based on Pyrazolone Derivatives Catalyzed by an Acidic Ionic Liquid Supported on Silica-Coated Magnetite Nanoparticle, J. Mol. Struct., 1154: 557-564 (2018).
[8] Safaei Ghomi J., Zahedi S., Novel Ionic Liquid Supported on Fe3O4 Nanoparticles and Its Application as a Catalyst in Mannich Reaction Under Ultrasonic Irradiation, Ultrason. Sonochem., 34: 916-923 (2017).
[9] Cheng W., Chen X., Sun J., Wang J., Zhang S., SBA-15 Supported Triazolium-Based Ionic Liquids as Highly Efficient and Recyclable Catalysts for Fixation of CO2 with Epoxides, J. Catal., 200: 117-124 (2013).
[10] Hosseini Daragahi S.A., Mohebat R., Mosslemin M.S., Green and Eco-Friendly Synthesis of Quinoxalines by Brönsted Acidic Ionic Liquid Supported on Nano-SiO2 Under Solvent-Free Conditions, Org. Prep. Proced. Intern., 50(3): 301-313 (2018). 
[11] Corma A., From Microporous to Mesoporous Molecular Sieve Materials and Their Use in Catalysis, Chem. Rev., 97(6): 2373-2420 (1997).
[12] Armistead C.G., Tiler A.J., Hambelton F.H., Mitchell S.A., Hochey J.A., Surface Hydroxylation of Silica, J. Phys. Chem., 73(11): 3947-3953 (1969).
[13] نعلبندی، احمد؛ خلیلی، علی اصغر، اپوکسیداسیون روغن سویا توسط کاتالیست ناهمگن سیلیکا سولفوریک اسید، نشریه شیمی و مهندسی شیمی ایران، (3)33: 19 تا 29 (1393).
[14] Freeman F., Properties and Reactions of Ylidenemalononitriles, Chem. Rev., 80(4): 329-350 (1980).
[15] Volkova M.S., Jensen K.C., Lozinskaya N.A., Sosonyuk S.E., Proskurnina M.V., Mesecar A.D., Zefirov N.S., Synthesis of Novel МТ3 Receptor Ligands via an Unusual Knoevenagel Condensation, Bioorg. Med. Chem. Lett., 22(24): 7578-7581 (2012).
[16] Tietze L.F., Beifuss U., ''The Knoevenagel Reaction'' Trost (Ed.), "Comprehensive Organic Synthesis", Pergamon Press, Oxford, UK (1991).
[17] Franconetti A., Domínguez-Rodríguez P., Lara-García D., Prado-Gotor R., Cabrera-Escribano F., Native and Modified Chitosan-Based Hydrogels as Green Heterogeneous Organocatalysts for Imine-Mediated Knoevenagel Condensation, Appl. Catal. A: Gen., 517: 176-186 (2016).
[18] Dong X., Hui Y., Xie S., Zhang P., Zhou G., Xie Z., Schiff Base Supported MCM-41 Catalyzed the Knoevenagel Condensation in Water, RSC Adv., 3(10): 3222-3226 (2013).
[19] Rosati O., Lanari D., Scavo R., Persia D., Marmottini F., Nocchetti M., Curini M., Piermatti O., Zirconium Potassium Phosphate Methyl and/or Phenyl Phosphonates as Heterogeneous Catalysts for Knoevenagel Condensation Under Solvent Free Conditions, Microporous Mesoporous Mat.,  268:251-259 (2018).
[20] Yadav J.S., Reddy B.V.S., Basa A.K., Visali B., Narsaiah A.V., Nagaiah K., Phosphane‐Catalyzed Knoevenagel Condensation: A Facile Synthesis of α‐Cyanoacrylates and α‐Cyanoacrylonitriles, Eur. J. Org. Chem., 2004(3): 546-551 (2004).
[21] Wang D.Y., Xi G.H., Ma J.J., Wang C., Zhang X.C., Wang Q.Q., Condensation Reactions of Aromatic Aldehydes with Active Methylene Compounds Catalyzed by Alkaline Ionic Liquid, Synth. Commun., 41(20): 3060-3065 (2011).
[22] Yamashita K., Tanaka T., Hayashi M., Use of Isopropyl Alcohol as a Solvent in Ti(O-i-Pr)4-Catalyzed Knöevenagel Reactions, Tetrahedron, 61(33): 7981-7985 (2005).
[23] Wang D.Y., Xi G. H., Ma J. J., Wang C., Zhang X.C., Wang Q.Q., Condensation Reactions of Aromatic Aldehydes with Active Methylene Compounds Catalyzed by Alkaline Ionic Liquid, Synth. Commun., 41(5): 3060-3065 (2011).
[24] Appaturi J. N., Selvaraj M., Abdul Hamid S. B., Synthesis of 3-(2-furylmethylene)-2,4-Pentanedione Using DL-Alanine Functionalized MCM-41 Catalyst via Knoevenagel Condensation Reaction, Microporous Mesoporous Mat., 260: 260-269 (2018).
Nashrieh Shimi va Mohandesi Shimi Iran
Volume 40, Issue 3 - Serial Number 101
September 2021
Pages 83-88

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