Imidazolium Chloride Immobilized Fly Ash as a Heterogenized Organocatalyst for Esterification Reaction under Microwave Irradiation Heating

Document Type: Research Article

Authors

Department of Pure and Applied Chemistry, University of Kota, Kota, 324005, Rajasthan, INDIA

Abstract

An efficient solventless one-pot procedure for the synthesis of imidazolium-based ionic liquid under microwave irradiation is described in which 1-methylimidazole was modified by organosilane (3-chloropropyl triethoxysilane). This ionic liquid 1-methyl-3-[(triethoxysilyl)propyl]imidazolium chloride (TMICl) is immobilized on Mechanically activated Fly Ash (MFA) by co-condensation method to develop an active organocatalyst (TMICl/MFA). The mechanical activation has generated significant number of silanol groups suitable for immobilizing ionic liquids. For characterization of various materials, different techniques viz, XRD, FTIR, SEM-EDX, TGA, BET surface area, H1NMR are used. The prepared TMICl/MFA exhibited high catalytic activity for a series of microwave assisted esterification of aliphatic alcohols and salicylic acid for four successive reaction cycles under optimized conditions.

Keywords

Main Subjects

References

[1] Welton T., Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis, Chem. Rev., 99(8): 2071-2084 (1999).

[2] Picquet M., Poinsot D., Stutzmann S., Tkatchenko I., Tommasi I., Wasserscheid P., Zimmermann J., Ionic Liquids: Media for Better Molecular Catalysis, Top. Catal., 29(3): 139-143 (2004).

[3] Liu B.Y., Han J., Dong J.F., Wei F., Cheng Y., Application of Ionic Liquid-Anchored Catalyst or Reagent to Organic Synthesis, Chin. J. Org. Chem., 27(10): 1236-1243 (2007).

[4] Cozzi F., Immobilization of Organic Catalysts: When, Why, and How, Adv. Synth. Catal., 348(12‐13): 1367-1390 (2006).

[5] Li P.H., Li B.L., Hu H.C., Zhao X.N., Zhang Z.H., Ionic Liquid Supported on Magnetic Nanoparticles as Highly Efficient and Recyclable Catalyst for the Synthesis of β-Keto Enol Ethers, Catal. Commun., 46: 118-122 (2014).

[6] Breitenlechner S., Fleck M., Müller T. E., Suppan A., Solid Catalysts on the Basis of Supported Ionic Liquids and Their use in Hydroamination Reactions, J. Mol. Catal. A: Chem., 214(1): 175-179
(2004).

[7] Kim D.W., Chi D.Y., Polymer‐Supported Ionic Liquids: Imidazolium Salts as Catalysts for Nucleophilic Substitution Reactions Including Fluorinations, Angew. Chem. Int. Ed., 43(4): 483-485 (2004).

[8] Riisager A., Fehrmann R., Flicker S., van Hal R., Haumann M., Wasserscheid P., Very Stable and Highly Regioselective Supported Ionic‐Liquid‐Phase (SILP) Catalysis: Continuous‐Flow Fixed‐Bed Hydroformylation of Propene, Angew. Chem. Int. Ed., 44(5): 815-819 (2005).

[9] Mehnert C.P., Supported Ionic Liquid Catalysis, Chem. Eur. J., 11(1): 50-56 (2005).

[10] Shi F., Zhang Q., Li D., Deng Y., Silica‐Gel‐Confined Ionic Liquids: A New Attempt for the Development of Supported Nanoliquid Catalysis, Chem. Eur. J., 11(18): 5279-5288 (2005).

[11] Wang F., Zhang Z., Yang J., Wang L., Lin Y., Wei Y., Immobilization of Room Temperature Ionic Liquid (RTIL) on Silica Gel for Adsorption Removal of Thiophenic Sulfur Compounds from Fuel, Fuel, 107: 394-399 (2013).

[12] Qiao K., Hagiwara H., Yokoyama C., Acidic Iionic Liquid Modified Silica Gel as Novel Solid Catalysts for Esterification and Nitration Reactions, J. Mol. Catal. A: Chem., 246: 65–69 (2006).

[13] Földes R.S., The Use of Supported Acidic Ionic Liquids in Organic Synthesis, Mol., 19: 8840-8884 (2014).

[14] Chrobok A., Baj S., Pudło W., Jarzębski A., Supported Hydrogensulfate Ionic Liquid Catalysis in Baeyer–Villiger Reaction, Appl. Catal. A: Gen., 366(1):  22-28 (2009).

[15] Sefat M. N., Saberi D., Niknam K., Preparation of Silica-Based Ionic Liquid an Efficient and Recyclable Catalyst for One-Pot Synthesis of α-Aminonitriles, Catal.Let., 141(11): 1713 -  (2011).

[16] Baghernejad M., Niknam K., Synthesis of 4, 4’-(Arylmethylene) bis (1H-pyrazol-5-ols) Using Silica-Bonded Ionic Liquid as Recyclable Catalyst, Int. J. of Chem.,4: 52-60 (2012).

[17] Parvin M.N., Jin H., Ansari M.B., Oh S.M., Park S.E., Imidazolium Chloride Immobilized SBA-15 as
a Heterogenizedorganocatalyst for Solvent Free Knoevenagel Condensation Using Microwave,  Appl. Catal. A: Gen., 413: 205-212 (2012).

[18] Sun J., Cheng W., Fan W., Wang Y., Meng Z.,  Zhang S., Reusable and Efficient Polymer-Supported Task-Specific Ionic Liquid Catalyst for Cycloaddition of Epoxide with CO2, Catal. Today,148: 361–367 (2009).

[19] Burguete M.I., Erythropel H., Garcia-Verdugo E., Luis S.V., Sans V., Base Supported Ionic Liquid-Like Phases as Catalysts for the Batch and Continuous-Flow Henry Reaction, Green Chem., 10: 401–407 (2008).

[20] Sugimura R., Qiao K., Tomida D., Yokoyama C., Immobilization of Acidic Ionic Lliquids by Copolymerization with Styrene and Their Catalytic Use for Acetal Formation, Catal. Commun. 8: 770–772 (2007).

[21] Abu‐Reziq R., Wang D., Post M., Alper H., Platinum Nanoparticles Supported on Ionic Liquid‐Modified Magnetic Nanoparticles: Selective Hydrogenation Catalysts, Adv. Synth. Catal.,349: 2145 – 2150 (2007).

[22] Karimi B., Mansouri F., Vali H., A Highly Water-Dispersible/Magnetically Separable Palladium Catalyst Based on a Fe3O4@SiO2 Anchored TEG-Imidazolium Ionic Liquid for the Suzuki–Miyaura Coupling Reaction in Water, Green Chem.,16: 2587-2596 (2014).

[23] Sun J., Cheng W., Fan W., Wang Y., Meng Z., Zhang S., Reusable and Efficient Polymer-Supported Task-Specific Ionic Liquid Catalyst for Cycloaddition of Epoxide with CO2, Catal. Today, 148: 361–367 (2009).

[24] Varma R.S., Namboodiri V.V., Solvent-Free Preparation of Ionic Liquids Using a Household Microwave Oven, Pure Appl. Chem., 73: 1309-1313 (2001).

[25] Seddon K.R., Stark A., Torres M.J., Influence of Chloride, Water, and Organic Solvents on the Physical Properties of Ionic Liquids, Pure Appl. Chem. 72 (12): 2275–2287 (2000).

[26] Miao J., Wan H., Shao Y., Guan G., Xu B., Acetalization of Carbonyl Compounds Catalyzed
by Acidic Ionic Liquid Immobilized on Silica Gel,
J. of Mol. Catal. A: Chem., 348: 77-82 (2011).

[27] Lin Y., Wang F., ZhangZ., Yang J., Wei Y., Polymer-supported Ionic Liquids: Synthesis, Characterization and Application in Fuel Desulfurization, Fuel, 116: 273–280 (2014).

[28] Li P.H., Li B.L., Hu H. C., Zhao X.N., Zhang Z.H., Ionic Liquid Supported on Magnetic Nanoparticles as Highly Efficient and Recyclable Catalyst for the Synthesis of β-Keto Enol Ethers, Catal. Commun., 46: 118–122 (2014).

[29] Mallick D., Khanra S., Chaudhuri S.K., Studies on the Potential of Coal Fly Ash as a Heterogeneous Catalyst in Oxidation of Aqueous Sodium Sulfide Solutions with Hydrogen Peroxide, J. Chem. Technol. Biotechnol,. 70(3): 231-240 (1997).

[30] Sharma A., Srivastava K., Devra V., Rani A., Modification in Properties of Fly Ash Through Mechanical and Chemical Activation, Ameri. Chem. Sci. J., 2(4):177-187 (2012).

[31] Patil G.A., Anandhan S., Ball Milling of Class-F Indian Fly ash Obtained from a Thermal Power Station, Int. J. Energy Eng.,  2:  57-62 (2012).

[32] Shringi N., Srivastava K., Rani A., Microwave Assisted Acid Activation of Fly Ash: A Green Process for Enhancing its Physico-Chemical Attributes for Esterification under Dielectric Heating, Chem. Sci. Rev. Lett., 4:561-570 (2015).

[33] Styszko-Grochowiak K., Gołaś J., Jankowski H., Koziński S., Characterization of the Coal Fly Ash for the Purpose of Improvement of Industrial on-Line Measurement of Unburned Carbon Content, Fuel, 83(13): 1847-1853 (2004).

[34] Jain D., Khatri C., Rani A., Fly Ash Supported Calcium Oxide as Recyclable Solid Base Catalyst for Knoevenagel Condensation Reaction, Fuel Proces. Technol., 91(9): 1015-1021 (2010).

[35] Jain D., Khatri C., Rani A., Synthesis and characterization of Novel Solid Base Catalyst from Fly Ash, Fuel, 90:2083–2088 (2011).

[36] Khatri C., Jain D., Rani A., Fly Ash-Supported Cerium Triflate as an Active Recyclable Solid Acid Catalyst for Friedel–Crafts Acylation Reaction, Fuel, 89(12): 3853-3859 (2010).

[37] Rani A., Rajoriya P., Supported Imidazolium Based Ionic Liquid as a Green, Highly Effective and Reusable Catalyst for Microwave Assisted Knoevenagel Condensation, Chem. Sci. Rev. Lett., 6(22): 772-778 (2017).

[38] Rani A., Khatri C., Hada R., Fly Ash Supported Scandium Triflate as an Active Recyclable Solid Acid Catalyst for Friedel–Crafts Acylation Reaction, Fuel process. Technol., 116: 366-373 (2013).

[39] Khatri C., Rani A., Synthesis of a Nano-Crystalline Solid Acid Catalyst from Fly Ash and Its Catalytic Performance, Fuel, 87(13-14): 2886-2892 (2008).

[40] Styszko K., Szczurowski J., Czuma N., Makowska D., Kistler M., Adsorptive Removal of Pharmaceuticals and Personal Care Products From Aqueous Solutions by Chemically Treated Fly Ash, Int. J. Environ. Sci. Technol., 15(3): 493-506 (2018).

[41] Agarwal S., Rani, A., Adsorption of Resorcinol from Aqueous Solution onto CTAB/NaOH/flyash Composites: Equilibrium, Kinetics and Thermodynamics, J. Environ. Chem. Eng. 5(1): 526-538 (2017).

[42] Agarwal S., Rajoria P., Rani A., Adsorption of Tannic Acid from Aqueous Solution onto Chitosan/NaOH/fly Ash Composites: Equilibrium, Kinetics, Thermodynamics and Modeling, J.  Environ. Chem. Eng., 6:1486–1499(2018).

[43] Marjanović N., Komljenović M., Baščarević Z.,  Nikolić V., Improving Reactivity of Fly Ash and Properties of Ensuing Geopolymers Through Mechanical Activation, Constr. Build. Mater., 57: 151-162. (2014).

[44] Buckingham J., Macdonald F., “Dictionary of Organic Compounds” [M], 6th ed., Chapman & Hall, London, 1998.

[45] Sahoo S., Kumar P., Lefebvre F., Halligudi S.B., Oxidative Kinetic Resolution of Alcohols Using Chiral Mn–Salen Complex Immobilized onto Ionic Liquid Modified Silica, Appl. Catal. A: Gen., 354(1): 17-25 (2009).

[46] Yuan C., Huang Z., Chen J., Basic Ionic Liquid Supported on Mesoporous SBA-15: an Efficient Heterogeneous Catalyst for Epoxidation of Olefins with H2O2 as Oxidant, Catal. Commun., 24: 56–60 (2012).

Iranian Journal of Chemistry and Chemical Engineering (IJCCE)

Volume 38, Issue 3 - Serial Number 95
May and June 2019
Pages 87-96

Files

Share

How to cite

Statistics