Abstract
A type of MCM-41 supported dual imidazolium ionic liquids have been synthesized and efficiently used as catalysts in the sustainable chemical conversion of CO2 and epoxides into cyclic carbonates. It was shown that the highest efficiency was achieved in the cycloaddition of a variety of epoxides and CO2 in the presence of the MCM-41@DILSCN solid catalyst under mild conditions. More interestingly, the catalyst was stable, very active, robust, and displayed good recyclability without significant loss of catalytic activity after six consecutive cycles during the process. Overall, the present protocol of synthesizing cyclic carbonates under solvent free conditions using MCM-41@DILSCN is promising for industrial applications.
Funding source: Research Foundation of Yichang Science and Technology Bureau
Award Identifier / Grant number: A21-3-009
Funding source: Research Foundation of Hubei Three Gorges Laboratory
Award Identifier / Grant number: SC213010
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: This work was supported by the Research Foundation of Yichang Science and Technology Bureau (A21-3-009), Research Foundation of Hubei Three Gorges Laboratory (SC213010).
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
Alves, M., B. Grignard, R. Mereau, C. Jerome, T. Tassaing, and C. Detrembleur. 2017. “Organocatalyzed Coupling of Carbon Dioxide with Epoxides for the Synthesis of Cyclic Carbonates: Catalyst Design and Mechanistic Studies.” Catalysis Science and Technology 7: 2651–84, https://doi.org/10.1039/c7cy00438a.Search in Google Scholar
Azzouz, R., V. C. Moreno, C. Herasme-Grullon, V. Levacher, L. Estel, A. Ledoux, S. Derrouiche, F. Marsais, and L. Bischoff. 2020. “Efficient Conversion of Epoxides into Carbonates with CO2 and A Single Organocatalyst: Laboratory and Kilogram-Scale Experiments.” Synlett 31: 183–8, https://doi.org/10.1055/s-0039-1691405.Search in Google Scholar
Bobadilla, L. F., T. Blasco, and J. A. Odriozola. 2013. “Gold(III) Stabilized over Ionic Liquids Grafted on MCM-41 for Highly Efficient Three-Component Coupling Reactions.” Physical Chemistry Chemical Physics 15: 16927–34, https://doi.org/10.1039/c3cp52924j.Search in Google Scholar PubMed
Calvete, M. J. F., M. Silva, M. M. Pereira, and H. D. Burrows. 2013. “Inorganic Helping Organic: Recent Advances in Catalytic Heterogeneous Oxidations by Immobilised Tetrapyrrolic Macrocycles in Micro and Mesoporous Supports.” RSC Advances 3: 22774–89, https://doi.org/10.1039/c3ra44038a.Search in Google Scholar
Chand, H., P. Choudhary, A. Kumar, A. Kumar, and V. Krishnan. 2021. “Atmospheric Pressure Conversion of Carbon Dioxide to Cyclic Carbonates Using a Metal-free Lewis Acid-Base Bifunctional Heterogeneous Catalyst.” Journal of CO2 Utilization 51: 101646, https://doi.org/10.1016/j.jcou.2021.101646.Search in Google Scholar
Chen, C., and A. Zhang. 2021. “Radii-dependent Self-Assembly Polynuclear Lanthanide Complexes as Catalysts for CO2 Transformation into Cyclic Carbonates.” New Journal of Chemistry 45: 20155–63, https://doi.org/10.1039/d1nj03652a.Search in Google Scholar
Chen, J., H. Li, M. Zhong, and Q. Yang. 2016. “Hierarchical Mesoporous Organic Polymer with an Intercalated Metal Complex for the Efficient Synthesis of Cyclic Carbonates from Flue Gas.” Green Chemistry 18: 6493–500, https://doi.org/10.1039/c6gc02367c.Search in Google Scholar
Chen, J., P. P. Zhao, D. Li, L. Liu, and H. Li. 2020. “Achieving the Transformation of Captured CO2 to Cyclic Carbonates Catalyzed by a Bipyridine Copper Complex-Intercalated Porous Organic Framework.” Industrial & Engineering Chemistry Research 59: 9423–31, https://doi.org/10.1021/acs.iecr.0c00874.Search in Google Scholar
Claver, C., M. B. Yeamin, M. Reguero, and A. M. Masdeu-Bultó. 2020. “Recent Advances in the Use of Catalysts Based on Natural Products for the Conversion of CO2 into Cyclic Carbonates.” Green Chemistry 22: 7665–706, https://doi.org/10.1039/d0gc01870h.Search in Google Scholar
Dai, W., S. Luo, S. Yin, and C. Au. 2010. “A Mini Review on Chemical Fixation of CO2: Absorption and Catalytic Conversion into Cyclic Carbonates.” Frontiers of Chemical Engineering in China 4: 163–71, https://doi.org/10.1007/s11705-009-0235-0.Search in Google Scholar
El-Salamony, R. A., S. A. El-Sharaky, S. A. Al-Temtamy, A. M. Al-Sabagh, and H. M. Killa. 2021. “CO2 Valorization into Synthetic Natural Gas (SNG) Using a Co–Ni Bimetallic Y2O3 Based Catalysts.” International Journal of Chemical Reactor Engineering 19 (6): 571–83, https://doi.org/10.1515/ijcre-2020-0163.Search in Google Scholar
Ema, T., Y. Miyazaki, T. Taniguchi, and J. Takada. 2013. “Robust Porphyrin Catalysts Immobilized on Biogenous Iron Oxide for the Repetitive Conversions of Epoxides and CO2 into Cyclic Carbonates.” Green Chemistry 15: 2485–92, https://doi.org/10.1039/c3gc41055b.Search in Google Scholar
Fehrmann, R., A. Riisager, and M. Haumann. 2014. Supported Ionic Liquids: Fundamentals and Applications. Weinheim: Wiley-VCH Verlag.10.1002/9783527654789Search in Google Scholar
Ge, Y., W. Liu, Y. Zou, G. Cheng, and H. Ke. 2022. “A Solid Zn Complex Catalyst for Efficient Transformation of CO2 to Cyclic Carbonates at Mild Conditions.” Tetrahedron 119: 132857, https://doi.org/10.1016/j.tet.2022.132857.Search in Google Scholar
Ghosh, A., G. N. Reddy, P. K. M. Siddhique, S. Chatterjee, S. Bhattacharjee, R. Maitra, S. E. Lyubimov, A. V. Arzumanyan, A. Naumkin, A. Bhaumik, and B. Chowdhury. 2022. “Fabrication of a Hollow Sphere N,S Co-doped Bifunctional Carbon Catalyst for Sustainable Fixation of CO2 to Cyclic Carbonates.” Green Chemistry 24: 1673–92, https://doi.org/10.1039/d1gc04153c.Search in Google Scholar
Goodrich, P., H. Q. N. Gunaratne, J. Jacquemin, L. Jin, Y. Lei, and K. R. Seddon. 2017. “Sustainable Cyclic Carbonate Production, Utilizing Carbon Dioxide and Azolate Ionic Liquids.” ACS Sustainable Chemistry & Engineering 5: 5635–41, https://doi.org/10.1021/acssuschemeng.7b00355.Search in Google Scholar
Hardacre, C., and V. Parvulescu. 2014. Catalysis In Ionic Liquids: From Catalyst Synthesis to Application. London: Royal Society of Chemistry.10.1039/9781849737210Search in Google Scholar
Helal, A., F. Alahmari, M. Usman, and Z. H. Yamani. 2022. “Chalcopyrite UiO-67 Metal-Organic Framework Composite for CO2 Fixation as Cyclic Carbonates.” Journal of Environmental Chemical Engineering 10: 108061, https://doi.org/10.1016/j.jece.2022.108061.Search in Google Scholar
Honores, J., D. Quezada, G. Chacón, O. Martínez-Ferraté, and M. Isaacs. 2019. “Synthesis of Cyclic Carbonates from CO2 and Epoxide Catalyzed by Co, Ni and Cu Complexes in Ionic Liquids.” Catalysis Letters 149: 1825–32, https://doi.org/10.1007/s10562-019-02728-4.Search in Google Scholar
Jayakumar, S., H. Li, L. Tao, C. Li, L. Liu, J. Chen, and Q. Yang. 2018. “Cationic Zn-Porphyrin Immobilized in Mesoporous Silicas as Bifunctional Catalyst for CO2 Cycloaddition Reaction under Cocatalyst Free Conditions.” ACS Sustainable Chemistry & Engineering 6: 9237–45, https://doi.org/10.1021/acssuschemeng.8b01548.Search in Google Scholar
Kang, M., F. Jin, Z. Li, H. Song, and J. Chen. 2020. “Research and Application of Supported Ionic Liquids.” Progress in Chemistry 32 (9): 1274–93.Search in Google Scholar
Kathalikkattil, A. C., R. Babu, R. K. Roshan, H. Lee, H. Kim, J. Tharun, E. Suresh, and D. W. Park. 2015. “An Lcy-Topology Amino Acid MOF as Eco-Friendly Catalyst for Cyclic Carbonate Synthesis from CO2: Structure-DFT Corroborated Study.” Journal of Materials Chemistry 3: 22636–47, https://doi.org/10.1039/c5ta05688h.Search in Google Scholar
Kaur, P., and K. H. Chopra. 2023. “MCM-41 Supported S-Alkyl/Aryl-Substituted 2-Mercaptobenzothiazolium-Based Ionic Liquids: Synthesis, Characterization, and Application in the Fuel Desulfurization.” Fuel 332: 126009, https://doi.org/10.1016/j.fuel.2022.126009.Search in Google Scholar
Koyuncu, D. D. E. 2021. “Mesoporous KIT-6 Supported Cr and Co-Based Catalysts for Microwave-Assisted Non-Oxidative Ethane Dehydrogenation.” International Journal of Chemical Reactor Engineering 19 (2): 179–91, https://doi.org/10.1515/ijcre-2020-0203.Search in Google Scholar
Kumar, K., and A. Kumar. 2018. “Enhanced CO2 Adsorption and Separation in Ionic-Liquid-Impregnated Mesoporous Silica MCM-41: A Molecular Simulation Study.” Journal of Physical Chemistry C 122: 8216–27, https://doi.org/10.1021/acs.jpcc.7b11529.Search in Google Scholar
Li, H., P. S. Bhadury, B. Song, and S. Yang. 2012. “Immobilized Functional Ionic Liquids: Efficient, Green, and Reusable Catalysts.” RSC Advances 2: 12525–51, https://doi.org/10.1039/c2ra21310a.Search in Google Scholar
Li, A., X. Wang, Y. Li, C. Luo, J. Zhang, K. Liu, C. Zhang, and C. Zhou. 2021. “A Novel Gemini Sulfonic Ionic Liquid Immobilized MCM-41 as Efficient Catalyst for Doebner-Von Miller Reaction to Quinolone.” ChemCatChem 13: 3772–80, https://doi.org/10.1002/cctc.202100424.Search in Google Scholar
Li, Y., D. Yan, and Y. Wu. 2019. “Ionic Liquid-Modified MCM-41-Polymer Mixed Matrix Membrane for Butanol Pervaporation.” Royal Society Open Science 6: 190291.10.1098/rsos.190291Search in Google Scholar PubMed PubMed Central
Li, Z. Q., Y. Y. Zhang, Y. J. Zheng, B. Li, and G. P. Wu. 2022. “Insights into Thiourea-Based Bifunctional Catalysts for Efficient Conversion of CO2 to Cyclic Carbonates.” Journal of Organic Chemistry 87: 3145–55, https://doi.org/10.1021/acs.joc.1c02888.Search in Google Scholar PubMed
Linares, N., A. M. Silvestre-Albero, E. Serrano, J. Silvestre-Albero, and J. García-Martínez. 2014. “Mesoporous Materials for Clean Energy Technologies.” Chemical Society Reviews 43: 7681–717, https://doi.org/10.1039/c3cs60435g.Search in Google Scholar PubMed
Liu, F., Y. Gu, P. Zhao, J. Gao, and M. Liu. 2019. “Cooperative Conversion of CO2 to Cyclic Carbonates in Dual-Ionic Ammonium Salts Catalytic Medium at Ambient Temperature.” ACS Sustainable Chemistry & Engineering 7: 5940–5, https://doi.org/10.1021/acssuschemeng.8b05997.Search in Google Scholar
Mandal, M. 2020. “Group 4 Complexes as Catalysts for the Transformation of CO2 into Polycarbonates and Cyclic Carbonates.” Journal of Organometallic Chemistry 907: 121067, https://doi.org/10.1016/j.jorganchem.2019.121067.Search in Google Scholar
Ola, O., M. M. Maroto-Valer, and S. Mackintosh. 2013. “Turning CO2 into Valuable Chemicals.” Energy Procedia 37: 6704–9, https://doi.org/10.1016/j.egypro.2013.06.603.Search in Google Scholar
Pal, T. K., D. De, and P. K. Bharadwaj. 2020. “Metal–organic Frameworks for the Chemical Fixation of CO2 into Cyclic Carbonates.” Coordination Chemistry Reviews 408: 213173, https://doi.org/10.1016/j.ccr.2019.213173.Search in Google Scholar
Pappuru, S., D. Shpasser, R. Carmieli, P. Shekhter, F. C. Jentoft, and O. M. Gazit. 2022. “Atmospheric-pressure Conversion of CO2 to Cyclic Carbonates over Constrained Dinuclear Iron Catalysts.” ACS Omega 7: 24656–61, https://doi.org/10.1021/acsomega.2c02488.Search in Google Scholar PubMed PubMed Central
Rahmanzadeh, L., and M. Taghizadeh. 2019. “Hydrogen Production from Ethanol Steam Reforming Using Ce- and La- Modified Mesoporous MCM-41 Supported Nickel-Based Catalysts.” International Journal of Chemical Reactor Engineering 17: 20180212, doi:https://doi.org/10.1515/ijcre-2018-0212.Search in Google Scholar
Raju, N. A., D. Prasad, P. M. Srinivasappa, A. V. Biradar, S. S. Gholap, A. K. Samal, B. M. Nagaraja, and A. H. Jadhav. 2022. “Recent Developments in State-of-the-Art Silica-Modified Catalysts for the Fixation of CO2 in Epoxides to form Organic Carbonates.” Sustainable Energy Fuels 6: 1198–248, https://doi.org/10.1039/d1se01916c.Search in Google Scholar
Rehman, A., F. Saleem, F. Javed, H. G. Qutab, V. C. Eze, and A. Harvey. 2021. “Kinetic Study for Styrene Carbonate Synthesis via CO2 Cycloaddition to Styrene Oxide Using Silica-Supported Pyrrolidinopyridinium Iodide Catalyst.” Journal of CO2 Utilization 43: 101379, https://doi.org/10.1016/j.jcou.2020.101379.Search in Google Scholar
Rejab, A., and H. Ksibi. 2022. “Particle Crystallization by Supercritical Antisolvent Processing Techniques: The Case of Retama Raetam Powder for Pharmaceutical Purposes.” International Journal of Chemical Reactor Engineering 20: 20220119, doi:https://doi.org/10.1515/ijcre-2022-0119.Search in Google Scholar
Ren, J., and S. Licht. 2016. “Tracking Airborne CO2 Mitigation and Low Cost Transformation into Valuable Carbon Nanotubes.” Scientific Reports 6: 27760, https://doi.org/10.1038/srep27760.Search in Google Scholar PubMed PubMed Central
Rehman, A., F. Saleem, F. Javed, A. Ikhlaq, S. W. Ahmad, and A. Harvey. 2021. “Recent Advances in the Synthesis of Cyclic Carbonates via CO2 Cycloaddition to Epoxides.” Journal of Environmental Chemical Engineering 9 (2): 105113, https://doi.org/10.1016/j.jece.2021.105113.Search in Google Scholar
Selvam, T., A. Machoke, and W. Schwieger. 2012. “Supported Ionic Liquids on Non-porous and Porous Inorganic Materials—A Topical Review.” Applied Catalysis A: General 445–446: 92–101, https://doi.org/10.1016/j.apcata.2012.08.007.Search in Google Scholar
Terazzi, C., K. Laatz, J. Langermann, and T. Werner. 2022. “Synthesis of Cyclic Carbonates Catalyzed by CaI2–Et3N and Studies on Their Biocatalytic Kinetic Resolution.” ACS Sustainable Chemistry & Engineering 10: 13335–42, https://doi.org/10.1021/acssuschemeng.2c03210.Search in Google Scholar
Tripathi, A. K., and K. R. Singh. 2016. “Interface and Core Relaxation Dynamics of IL Molecules in Nanopores of Ordered Mesoporous MCM-41: A Dielectric Spectroscopy Study.” RSC Advances 6: 45147–57, https://doi.org/10.1039/c6ra04212k.Search in Google Scholar
Verma, D. K., Y. Dewangan, A. K. Singh, R. Mishra, M. A. B. H. Susan, R. Salim, M. Taleb, F. E. Hajjaji, and E. Berdimurodov. 2022. “Ionic Liquids as Green and Smart Lubricant Application: An Overview.” Ionics 28: 4923–32, https://doi.org/10.1007/s11581-022-04699-w.Search in Google Scholar
Vieira, M. O., W. F. Monteiro, B. S. Neto, R. Ligabue, V. V. Chaban, and S. Einloft. 2018. “Surface Active Ionic Liquids as Catalyst for CO2 Conversion to Propylene Carbonate.” Catalysis Letters 148: 108–18, https://doi.org/10.1007/s10562-017-2212-4.Search in Google Scholar
Yadav, N., and M. Ahmaruzzaman. 2022. “Ionic Liquid-Based Nanocomposites for Organic Transformations.” Journal of the Iranian Chemical Society 19: 4327–47, https://doi.org/10.1007/s13738-022-02615-7.Search in Google Scholar
Zhang, S. J., and X. M. Lu. 2006. Ionic Liquids: From Fundamental Research to Industrial Applications. Beijing: Science Press.Search in Google Scholar
Zhang, X., D. Su, L. Xiao, and W. Wu. 2017. “Immobilized Protic Ionic Liquids: Efficient Catalysts for CO2 Fixation with Epoxides.” Journal of CO2 Utilization 17: 37–42, https://doi.org/10.1016/j.jcou.2016.11.005.Search in Google Scholar
Supplementary Materials
This article contains supplementary material (https://doi.org/10.1515/ijcre-2022-0210).
© 2023 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Articles
- Enhanced mechanical stirring by eccentric impeller stirring system in zinc hydrometallurgy process for cadmium removal
- DEM simulation of biomass pyrolysis in a novel interconnected screw reactor
- Numerical and experimental investigations on enhancement mixing performance of multi-blade stirring system for fluids with different viscosities
- The technical and economic analysis of processing and conversion of heavy oil cuts to valuable refinery products
- Effect of inlet gas velocity on gas-solid fluidization characteristics in fluidized bed
- Investigation into a multiple input/output bifurcated biochemical reaction with substrate inhibition in a real CSTR based on Cholette’s model
- Performance of photocatalytic oxidation surface with new geometry for indoor environment application: experimental and simulation
- Optimization of hydrothermal liquefaction process for bio-oil products from kitchen residue under subcritical conditions
- Value-added biochar production from microwave pyrolysis of peanut shell
- Short Communications
- Environmentally sustainable synthesis of cyclic carbonates from epoxides and CO2 promoted by MCM-41 supported dual imidazolium ionic liquids catalysts
Articles in the same Issue
- Frontmatter
- Articles
- Enhanced mechanical stirring by eccentric impeller stirring system in zinc hydrometallurgy process for cadmium removal
- DEM simulation of biomass pyrolysis in a novel interconnected screw reactor
- Numerical and experimental investigations on enhancement mixing performance of multi-blade stirring system for fluids with different viscosities
- The technical and economic analysis of processing and conversion of heavy oil cuts to valuable refinery products
- Effect of inlet gas velocity on gas-solid fluidization characteristics in fluidized bed
- Investigation into a multiple input/output bifurcated biochemical reaction with substrate inhibition in a real CSTR based on Cholette’s model
- Performance of photocatalytic oxidation surface with new geometry for indoor environment application: experimental and simulation
- Optimization of hydrothermal liquefaction process for bio-oil products from kitchen residue under subcritical conditions
- Value-added biochar production from microwave pyrolysis of peanut shell
- Short Communications
- Environmentally sustainable synthesis of cyclic carbonates from epoxides and CO2 promoted by MCM-41 supported dual imidazolium ionic liquids catalysts