Single-step fabrication of Na-TUD-1 novel heterogeneous base nano-catalyst for Knoevenagel condensation reaction
- Catalysis Research Group (CRG), Department of Chemistry, College of Science, King Khalid University, Abha, 61413, SA Chemistry Department, College of Science, Umm Al-Qura University, Makkah, SA
- Chemistry Department, College of Science, Umm Al-Qura University, Makkah, SA
- Advanced Functional Materials and Optoelectronics Laboratory (AFMOL), Department of Physics, College of Science, King Khalid University, Abha, 61413, SA
- NanoBioTech Laboratory, Department of Natural Sciences, Division of Sciences, Art and Mathematics, Florida Polytechnic University, Lakeland, FL, 33805, US
- Catalysis Research Group (CRG), Department of Chemistry, College of Science, King Khalid University, Abha, 61413, SA
Published in Issue 07-11-2020
How to Cite
Al-Shehri, B. M., Shabaan, M. R., Shkir, M., Kaushik, A., & Hamdy, M. S. (2020). Single-step fabrication of Na-TUD-1 novel heterogeneous base nano-catalyst for Knoevenagel condensation reaction. Journal of Nanostructure in Chemistry, 11(2 (June 2021). https://doi.org/10.1007/s40097-020-00364-8
Abstract
Abstract This research, for the first time, reports the design and development of a heterogeneous nano-catalyst based on sodium ions (Na + ) incorporation in Technical University of Delft (TUD-1) mesoporous silica for Knoevenagel condensation reaction. Facile one-step fabrication of Na-TUD-1 nano-catalysts (varying Si/Na ratio as 100–5) was demonstrated using the sol–gel route. The catalytic performance of Na-TUD-1 was evaluated as a base heterogeneous catalyst in Knoevenagel condensation reaction, which took place under conventional and microwave irradiations conditions using ethanol as a solvent. Na-TUD-1 exhibited superior catalytic activity in comparison to available homogeneous base catalysts such as sodium ethoxide. The Na-TUD-1 nano-catalyst demonstrated identical performance till the fourth run along with high stability and negligible leaching of Na. Moreover, the use of microwave heating reduced the reaction time from 240 to 20 min only with a TOF of 0.58 min −1 . Such excellent performance of Na-TUD-1 heterogeneous nano-catalysts will certainly increase its industrial acceptability to achieve affordable and efficient waste-effluent treatments.Keywords
- Na-TUD-1,
- Knoevenagel condensation,
- Microwave,
- Conventional heating,
- Base catalyst
References
- Sheldon et al. (2007) (pp. 295-328) Wiley
- Prout et al. (1963) Catalyst study of the Knoevenagel condensation 8(4) (pp. 597-599) https://doi.org/10.1021/je60019a037
- Villemin et al. (2003) Optimisation of solvent free parallel synthesis under microwave irradiation: synthesis of new arylacrylonitriles 5(4) (pp. 467-469) https://doi.org/10.1039/b305511f
- Bogdał (1998) Coumarins: fast synthesis by Knoevenagel condensation under microwave irradiation (pp. 468-469) https://doi.org/10.1039/a801724g
- Wada and Suzuki (2003) Calcite and fluorite as catalyst for the Knövenagel condensation of malononitrile and methyl cyanoacetate under solvent-free conditions 44(2) (pp. 399-401) https://doi.org/10.1016/S0040-4039(02)02431-0
- Hangarge et al. (2002) Knoevenagel condensation reactions in an ionic liquid 4(3) (pp. 266-268) https://doi.org/10.1039/b111634g
- Sebti et al. (2002) Natural phosphate doped with potassium fluoride and modified with sodium nitrate: efficient catalysts for the Knoevenagel condensation 43(10) (pp. 1813-1815) https://doi.org/10.1016/S0040-4039(02)00092-8
- Amantini et al. (2001) Water, a clean, inexpensive, and re-usable reaction medium. One-pot synthesis of (E)-2-aryl-1-cyano-1-nitroethenes 3(5) (pp. 229-232) https://doi.org/10.1039/b105522b
- Zhang et al. (2004) An investigation of Knoevenagel condensation reaction in microreactors using a new zeolite catalyst 261(1) (pp. 109-118) https://doi.org/10.1016/j.apcata.2003.10.045
- Martins et al. (2008) Basic catalyzed Knoevenagel condensation by FAU zeolites exchanged with alkylammonium cations (pp. 706-710) https://doi.org/10.1016/j.cattod.2007.12.043
- Mondal et al. (2011) Highly efficient mesoporous base catalyzed Knoevenagel condensation of different aromatic aldehydes with malononitrile and subsequent noncatalytic Diels-Alder reactions 335(1) (pp. 236-241) https://doi.org/10.1016/j.molcata.2010.11.039
- Ruiz et al. (1999) High-branched selectivity in the palladium-catalysed alkoxycarbonylation of styrene in the presence of thiol–thioether atropisomeric ligands 143(1) (pp. 171-180) https://doi.org/10.1016/S1381-1169(98)00383-5
- Opanasenko et al. (2013) Catalytic performance of metal–organic-frameworks in Knoevenagel condensation (pp. 500-507) https://doi.org/10.1039/C2CY20586F
- Choudary et al. (1999) Knoevenagel and aldol condensations catalysed by a new diamino-functionalised mesoporous material 142(3) (pp. 361-365) https://doi.org/10.1016/S1381-1169(98)00301-X
- Xue et al. (2018) Knoevenagel condensation reactions catalyzed by nitrogen-containing mesoporous carbon materials under mild reaction conditions 44(12) (pp. 7641-7655) https://doi.org/10.1007/s11164-018-3578-7
- Jansen et al. (2001) A new templating method for three-dimensional mesopore networks (pp. 713-714) https://doi.org/10.1039/b101000j
- Hamdy et al. (2005) Synthesis, characterization, and unique catalytic performance of the mesoporous material Fe-TUD-1 in Friedel-Crafts benzylation of benzene 100(3–4) (pp. 255-260) https://doi.org/10.1016/j.cattod.2004.10.018
- Saputera et al. (2015) Ti3+-containing titania: synthesis tactics and photocatalytic performance (pp. 60-66) https://doi.org/10.1016/j.cattod.2014.07.049
- Anand et al. (2004) Liquid-phase oxidation of cyclohexane over Co-TUD-1 95(3–4) (pp. 113-117) https://doi.org/10.1023/B:CATL.0000027283.70453.1a
- Hamdy and Mul (2012) Synthesis, characterization and catalytic performance of Mo-TUD-1 catalysts in epoxidation of cyclohexene 2(9) (pp. 1894-1900) https://doi.org/10.1039/c2cy20073b
- Hamdy (2016) Au-TUD-1: a new catalyst for aerobic oxidation of cyclohexene (pp. 81-87) https://doi.org/10.1016/j.micromeso.2015.08.032
- Al-Shehri et al. (2020) Noble metal nanoparticles incorporated siliceous TUD-1 mesoporous nano-catalyst for low-temperature oxidation of carbon monoxide
- Hamdy et al. (2017) New catalyst with multiple active sites for selective hydrogenolysis of cellulose to ethylene glycol 19(21) (pp. 5144-5151) https://doi.org/10.1039/C7GC02122D
- Al-Shehri et al. (2020) Enhancement the photocatalytic performance of semiconductors through composite formation with Eu-TUD-1 https://doi.org/10.1016/j.ijleo.2019.163522
- Sun et al. (2010) One-pot synthesized mesoporous Ca/SBA-15 solid base for transesterification of sunflower oil with methanol 390(1) (pp. 26-34) https://doi.org/10.1016/j.apcata.2010.09.030
- Sing et al. (1985) International union of pure commission on colloid and surface chemistry including catalysis* reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity 57(4) (pp. 603-619) https://doi.org/10.1351/pac198557040603
- Adam et al. (2011) A simple template-free sol–gel synthesis of spherical nanosilica from agricultural biomass 59(3) (pp. 580-583) https://doi.org/10.1007/s10971-011-2531-7
- Shan et al. (2001) Synthesis, characterization and catalytic testing of a 3-D mesoporous titanosilica, Ti–TUD-1 48(1) (pp. 181-187) https://doi.org/10.1016/S1387-1811(01)00342-0
- Jin H. Synthesis of NaOH-impregnated Calcined Oyster Shell for Transesterification Reaction. (PhD Thesis) (2017)
- Kumar et al. (2016) Electrochemical studies of non-aqueous Na–O2 cells employing Ag-RGO as the bifunctional catalyst 6(68) (pp. 63477-63479) https://doi.org/10.1039/C6RA13596J
- Yadegari et al. (2014) On rechargeability and reaction kinetics of sodium–air batteries 7(11) (pp. 3747-3757) https://doi.org/10.1039/C4EE01654H
- Hamdy et al. (2005) Fe, Co and Cu-incorporated TUD-1: synthesis, characterization and catalytic performance in N2O decomposition and cyclohexane oxidation 110(3) (pp. 264-271) https://doi.org/10.1016/j.cattod.2005.09.026
- Hamdy (2014) One-step synthesis of M-doped TiO2 nanoparticles in TUD-1 (M-TiO2-TUD-1, M=Cr or V) and their photocatalytic performance under visible light irradiation (pp. 39-46) https://doi.org/10.1016/j.molcata.2014.05.039
- Benaissa et al. (2017) Solvent-free selective hydrogenation of 1,5-cyclooctadiene catalyzed by palladium incorporated TUD-1 (pp. 62-65) https://doi.org/10.1016/j.catcom.2017.07.026
- Mubarak et al. (2019) In-situ activation of Pd-TUD-1 during the selective reduction of 1,5-cyclooctadiene (pp. 225-231) https://doi.org/10.1016/j.micromeso.2018.11.035
- Song et al. (2018) Synthesis of an Ni2P catalyst supported on Na-MCM-41 with highly activity for dibenzothiophene HDS under mild conditions 44(9) (pp. 5285-5299) https://doi.org/10.1007/s11164-018-3423-z
- Michalska et al. (2006) The role of MCM-41 composition in the creation of basicity by alkali metal impregnation 90(1) (pp. 362-369) https://doi.org/10.1016/j.micromeso.2005.09.033
- Albayati and Doyle (2015) Encapsulated heterogeneous base catalysts onto SBA-15 nanoporous material as highly active catalysts in the transesterification of sunflower oil to biodiesel 17(2) https://doi.org/10.1007/s11051-015-2924-6
- Chen et al. (2014) Transesterification of canola oil as biodiesel over Na/Zr-SBA-15 catalysts: Effect of zirconium content 39(34) (pp. 19555-19562) https://doi.org/10.1016/j.ijhydene.2014.08.154
- Shen et al. (2010) Brønsted base-catalyzed one-pot three-component biginelli-type reaction: an efficient synthesis of 4,5,6-triaryl-3,4-dihydropyrimidin-2(1H)-one and mechanistic study 75(4) (pp. 1162-1167) https://doi.org/10.1021/jo902394y
- Kamal Raj et al. (2011) A mechanistic investigation of Biginelli reaction under base catalysis 52(28) (pp. 3605-3609) https://doi.org/10.1016/j.tetlet.2011.05.011
- Shen et al. (2010) Brønsted Base-Catalyzed One-Pot Three-Component Biginelli-Type Reaction: An Efficient Synthesis of 4,5,6-Triaryl-3,4-dihydropyrimidin-2(1H)-one and Mechanistic Study https://doi.org/10.1021/jo902394y
- Raj et al. (2011) A mechanistic investigation of Biginelli reaction under base catalysis https://doi.org/10.1016/j.tetlet.2011.07.062
- Albayati and Aidan (2015) Encapsulated heterogeneous base catalysts onto SBA-15 nanoporous material as highly active catalysts in the transesterification of sunflower oil to biodiesel https://doi.org/10.1007/s11051-015-2924-6
- Chen et al. (2014) Transesterification of canola oil as biodiesel over Na/Zr-SBA-15 catalysts: Effect of zirconium content https://doi.org/10.1016/j.ijhydene.2014.08.154
10.1007/s40097-020-00364-8