Abstract
The current production of organic cyclic carbonates involves the reaction of appropriate alcohols with toxic phosgene. But an alternative route for obtaining these valuable products is the cycloaddition reaction of CO2 with appropriative epoxides. The development of new catalytic systems for this reaction is a highly active field of research works. For this purpose, were developed many effective catalytic systems, such as organocatalysts, metal–organic frameworks, homogeneous metal-based catalysts, and ionic liquid catalysts. Among them, zinc-containing and ionic liquid catalysts are highly active systems, resulting in the increase in selectivity and the beneficial effect on the reaction rate under mild reaction conditions: reaction temperatures of below 100 °C at a low CO2 concentration and pressure at 0.1 MPa, if possible, without solvents and co-catalysts. This review article summarizes and discusses the results of research works over the last 10–15 years on the study of the homogeneous zinc-containing and ionic liquid catalysts for the cycloaddition reaction of CO2 with epoxides. We hope that it can be stimulated for further development in this area and will be useful for understanding the potential commercialization of these catalysts.
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M. Crippa, G. Oreggioni, D. Guizzardi, M. Muntean, E. Schaaf, V.E. Lo, E. Solazzo, F. Monforti-Ferrario, J.G.J. Olivier. E. Vignati, Fossil CO2 and GHG emissions of all world countries - 2019 Report. https://doi.org/10.2760/687800
D.Y.C. Leung, G. Caramanna, M.M. Maroto-Valer, An overview of current status of carbon dioxide captures and storage technologies. Renew. Sustain. Energy Rev. 39, 426–443 (2014). https://doi.org/10.1016/j.rser.2014.07.093
G. Kramm, R. Dlugi, Scrutinizing the atmospheric greenhouse effect and its climatic impact. Nat. Sci. 3, 971–998 (2011). https://doi.org/10.4236/ns.2011.312124
Michele Aresta (Ed.) Carbon dioxide as chemical feedstock. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 370 p, (2010)
A. Dibenedetto, A. Angelini, P. Stufano, Use of carbon dioxide as feedstock for chemicals and fuels: homogeneous and heterogeneous catalysis. J. Chem. Technol. Biotechnol. 89, 334–353 (2014). https://doi.org/10.1002/jctb.4229
S. Dabral, T. Schaub, The use of carbon dioxide (CO2) as a building block in organic synthesis from an industrial perspective. Adv. Synth. Catal. 361(2), 223–246 (2018). https://doi.org/10.1002/adsc.201801215
I. Omae, Aspects of carbon dioxide utilization. Catal. Today 115(1–4), 33–52 (2006). https://doi.org/10.1016/j.cattod.2006.02.024
D.J. Darensbourg, Chemistry of carbon dioxide relevant to its utilization: a personal perspective. Inorg. Chem. 49(23), 10765–10780 (2010). https://doi.org/10.1021/ic101800d
C. Martín, G. Fiorani, A.W. Kleij, Recent advances in the catalytic preparation of cyclic organic carbonates. ACS Catal. 5, 1353–1370 (2015). https://doi.org/10.1021/cs5018997
H. Buttner, L. Longwitz, J. Steinbauer, C. Wulf, T. Werner, Recent developments in the synthesis of cyclic carbonates from epoxides and CO2. Top. Curr. Chem. 375, 49–105 (2017). https://doi.org/10.1007/s41061-017-0136-5
T. Sakakura, K. Kohno, The synthesis of organic carbonates from carbon dioxide. Chem. Commun. 11, 1312–1330 (2009). https://doi.org/10.1039/b819997c
B. Schaffner, F. Schaffner, S.P. Verevkin, A. Borner, Organic carbonates as solvents in synthesis and catalysis. Chem. Rev. 110, 4554–4581 (2010). https://doi.org/10.1021/cr900393d
V. Besse, F. Camara, C. Voirin, R. Auvergne, S. Caillol, B. Boutevin, Synthesis and applications of unsaturated cyclocarbonates. Polym. Chem. 4, 4545–4561 (2013). https://doi.org/10.1039/c3py00343d
R.H. Heyn, Organic carbonates, in Carbon dioxide utilisation: closing the carbon cycle. ed. by P. Styring, E.A. Quadrelli, K. Armstrong (Elsevier, 2014)
H. Zhang, H.-B. Liu, J.-M. Yue, Organic carbonates from natural sources. Chem. Rev. 114, 883–899 (2014). https://doi.org/10.1021/cr300430e
M. North, R. Pasquale, C. Young, Synthesis of cyclic carbonates from epoxides and CO2. Green Chem. 12, 1514–1539 (2010). https://doi.org/10.1039/c0gc00065e
T. Sakakura, K. Kohno, The synthesis of organic carbonates from carbon dioxide. Chem. Commun. 45, 1312–1330 (2009). https://doi.org/10.1039/b819997c
G. Fiorani, W.S. Guo, A.W. Kleij, Sustainable conversion of carbon dioxide: the advent of organocatalysis. Green Chem. 17, 1375–1389 (2015). https://doi.org/10.1039/c4gc01959h
M. Cokoja, M.E. Wilhelm, M.H. Anthofer, W.A. Herrmann, F.E. Kuhn, Synthesis of cyclic carbonates from epoxides and carbon dioxide by using organocatalysts. Chem. Sus. Chem. 8, 2436–2454 (2015). https://doi.org/10.1002/cssc.201500161
F.D. Bobbink, P.J. Dyson, Synthesis of carbonates and related compounds incorporating CO2 using ionic liquid-type catalysts: state-of-the-art and beyond. J. Catal. 343, 52–61 (2016). https://doi.org/10.1016/j.jcat.2016.02.033
B.-H. Xu, J.-Q. Wang, J. Sun, Y. Huang, J.-P. Zhang, X.-P. Zhang, S.-J. Zhang, Fixation of CO2 into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach. Green Chem. 17, 108–122 (2015). https://doi.org/10.1039/c4gc01754d
W. Cheng, Q. Su, J. Wang, J. Sun, F.T.T. Ng, Ionic liquids: the synergistic catalytic effect in the synthesis of cyclic carbonates. Catalysts 3, 878–901 (2013). https://doi.org/10.3390/catal3040878
J. Sun, S.-I. Fujita, M. Arai, Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids. J. Organomet. Chem. 690(15), 3490–3497 (2005). https://doi.org/10.1016/j.jorganchem.2005.02.011
M.H. Beyzavi, C.J. Stephenson, Y. Liu, O. Karagiaridi, J.T. Hupp, O.K. Farha, Metal–organic framework-based catalysts: chemical fixation of CO2 with epoxides leading to cyclic organic carbonates. Front. Energy. Res. 2, 1–10 (2015). https://doi.org/10.3389/fenrg.2014.00063
A.C. Kathalikkattil, R. Babu, J. Tharun, R. Roshan, D.-W. Park, Advancements in the conversion of carbon dioxide to cyclic carbonates using metal organic frameworks as catalysts. Catal. Surv. Asia 19, 223–235 (2015). https://doi.org/10.1007/s10563-015-9196-0
A. Decortes, A.M. Castilla, A.W. Kleij, Salen-complex-mediated formation of cyclic carbonates by cycloaddition of CO2 to epoxides. Angew. Chem. Int. Ed. 49(51), 9822–9837 (2010). https://doi.org/10.1002/anie.201002087
X. Wu, J. Castro-Osma, M. North, Synthesis of chiral cyclic carbonates via kinetic resolution of racemic epoxides and carbon dioxide. Symmetry 8(1), 4–10 (2016). https://doi.org/10.3390/sym8010004
J.W. Comerford, I.D.V. Ingram, M. North, X. Wu, Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings. Green Chem. 17(4), 1966–1987 (2015). https://doi.org/10.1039/c4gc01719f
G. Laugel, C.C. Rocha, P. Massiani, T. Onfroy, F. Launay, Homogeneous and heterogeneous catalysis for the synthesis of cyclic and polymeric carbonates from CO2 and epoxides: a mechanistic overview. Adv. Chem. Lett. 1, 195–214 (2013). https://doi.org/10.1166/acl.2013.1036
B.-H. Xu, J.-Q. Wang, J. Sun, Y. Huang, J.-P. Zhang, X.-P. Zhang, S.-J. Zhang, Fixation of CO2 into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach. Green Chem. 17(1), 108–122 (2015). https://doi.org/10.1039/c4gc01754d
S. Enthaler, X.-F. Wu (Eds.) Zinc catalysis: applications in organic synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, 326 p (2015). https://doi.org/10.1002/9783527675944
Z. Alaji, E. Safaei, A. Wojtczak, Development of pyridine based o-aminophenolate zinc complexes as structurally tunable catalysts for CO2 fixation into cyclic carbonates. New J. Chem. 41, 10121–10131 (2017). https://doi.org/10.1039/c7nj01656e
C.-A. Laia, C.-C. Ariadna, C. Javier, R. Mar, M.M.-B. Anna, A. Ali, Highly active and selective Zn(II)-NN`O schiff base catalysts for the cycloaddition of CO2 to epoxides. J. CO2 Util. 14, 10–22 (2016). https://doi.org/10.1016/j.jcou.2016.01.002
J.L.S. Milani, I.S. Oliveira, P.A. Dos Santos, A.K.S.M. Valdo, F.T. Martins, D. Cangussu, R.P. Das Chagas, Chemical fixation of carbon dioxide to cyclic carbonates catalyzed by zinc(II) complex bearing 1,2-disubstituted benzimidazole ligand. Chin. J. Catal. 39, 245–249 (2018). https://doi.org/10.1016/S1872-2067(17)62992-9
S. Sonia, N. Marta, F.-B. Juan, F.S.-B. Luis, G. Andrés, L.-S. Agustín, A.C.-O. José, Efficient CO2 fixation into cyclic carbonates catalyzed by NN`O-scorpionate zinc complexes. Dalton Trans. 48, 10733–10742 (2019). https://doi.org/10.1039/c9dt01844a
C.-G. Fernando, S. Giovanni, W.K. Arjan, B. Carleso, A DFT study on the mechanism of the cycloaddition reaction of CO2 to epoxides catalyzed by Zn(Salphen) complexes. Chem. Eur. J. 19, 6289–6298 (2013). https://doi.org/10.1002/chem.201203985
C. Maeda, T. Taniguchi, K. Ogawa, T. Ema, Bifunctional catalysts based on m-phenylene-bridged porphyrin dimer and trimer platforms: synthesis of cyclic carbonates from carbon dioxide and epoxides. Angew. Chem. Int. Ed. 54(1), 134–138 (2014). https://doi.org/10.1002/anie.201409729
B.H. Vignesh, K. Muralidharan, Zn(II), Cd(II) and Cu(II) complexes of 2,5-bis{N-(2,6-diisopropylphenyl)iminomethyl}pyrrole: synthesis, structures and their high catalytic activity for efficient cyclic carbonate synthesis. Dalton Trans. 42(4), 1238–1248 (2013). https://doi.org/10.1039/c2dt31755a
E. Mercad, E. Zangrando, C. Claver, C. Godard, Robust zinc complexes that contain pyrrolidine-based ligands as recyclable catalysts for the synthesis of cyclic carbonates from carbon dioxide and epoxides. Chem. Cat. Chem. 8(1), 234–243 (2015). https://doi.org/10.1002/cctc.201500772
C. Maeda, S. Sasaki, T. Ema, Electronic tuning of zinc porphyrin catalysts for the conversion of epoxides and CO2 into cyclic carbonates. Chem. Cat. Chem. 9(6), 946–949 (2017). https://doi.org/10.1002/cctc.201601690
Q.-Y. Yuan, P. Zhang, Y.-L. Shi, D.-H. Liu, Dual-ligand complex catalysts for the cycloaddition of propylene oxide and carbon dioxide. J. Mol. Struct. 1150, 329–334 (2017). https://doi.org/10.1016/j.molstruc.2017.08.056
J.G. Vitillo, V. Crocellà, F. Bonino, ZIF-8 as a catalyst in ethylene oxide and propylene oxide reaction with CO2 to cyclic organic carbonates. Chem. Eng. 3(3), 60–74 (2019). https://doi.org/10.3390/chemengineering3030060
E.F. Nasirli, Alkylene carbonates synthesis by the reaction of carbon dioxide and ethylene oxide in the presence of zink phenolates. Int. J. Nano Chem. 5(3), 21–29 (2019). https://doi.org/10.18576/ijnc/050301
E.F. Nasirli, M.J. Ibrahimova, MKh. Mamedov, F.A. Nasirov, Synthesis of ethylene carbonate by the cycloaddition reaction of ethylene oxide with carbon dioxide in the presence of highly efficient zinc-phenolate catalysts. Process. Petrochem. Oil Refin. 21(1), 14–21 (2020)
H. Kawanami, A. Sasaki, K. Matsui, Y. Ikushima, A rapid and effective synthesis of propylene carbonate using a supercritical CO2–ionic liquid system. Chem. Commun (2003). https://doi.org/10.1039/b212823c.
S. Zhang, Y. Chen, F. Li, X. Lu, W. Dai, R. Mori, Fixation and conversion of CO2 using ionic liquids. Catal. Today. 115(1–4), 61–69 (2006). https://doi.org/10.1016/j.cattod.2006.02.021
J.-I. Yu, H.-Y. Ju, K.-H. Kim, D.-W. Park, Cycloaddition of carbon dioxide to butyl glycidyl ether using imidazolium salt ionic liquid as a catalyst. Korean J. Chem. Eng. 27(2), 446–451 (2010). https://doi.org/10.1007/s11814-010-0074-1
N.V. Rees, R.G. Compton, Electrochemical CO2 sequestration in ionic liquids; a perspective. Energy Environ. Sci. 4, 403–408 (2011). https://doi.org/10.1039/c0ee00580k
T. Sakakura, K. Kohno, The synthesis of organic carbonates from carbon dioxide. Chem. Commun (2009). https://doi.org/10.1039/b819997c
P.P. Pescarmona, M. Taherimehr, Challenges in the catalytic synthesis of cyclic and polymeric carbonates from epoxides and CO2. Catal. Sci. Technol. 2, 2169–2187 (2012). https://doi.org/10.1039/c2cy20365k
J. Sun, S.-I. Dujita, M. Arai, Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids. J. Organomet. Chem. 690, 3490–3497 (2005). https://doi.org/10.1016/j.jorganchem.2005.02.011
P. Goodrich, H.Q.N. Gunaratne, J. Jacquemin, L. Jin, Y. Lei, K.R. Seddon, Sustainable cyclic carbonate production, utilising carbon dioxide and azolate ionic liquids. ACS Sustain. Chem. Eng. 5(7), 5635–5641 (2017). https://doi.org/10.1021/acssuschemeng.7b00355
M. Liu, L. Liang, X. Li, X. Gao, J. Sun, Novel urea derivative based ionic liquids with dual-functions: CO2 capture and conversion under metal- and solvent-free conditions. Green Chem. 18, 2851–2863 (2016). https://doi.org/10.1039/c5gc02605a
M. Liu, P. Zhao, Y. Gu, R. Ping, J. Gao, F. Liu, Squaramide functionalized ionic liquids with well-designed structures: highly-active and recyclable catalyst platform for promoting cycloaddition of CO2 to epoxides. J. CO2 Util. 37, 39–44 (2020). https://doi.org/10.1016/j.jcou.2019.11.028
F. Liu, Y. Gu, P. Zhao, H. Xin, J. Gao, M. Liu, N-hydroxysuccinimide based deep eutectic catalysts as a promising platform for conversion of CO2 into cyclic carbonates at ambient temperature. J. CO2 Util. 33, 419–426 (2019). https://doi.org/10.1016/j.jcou.2019.07.017
S. Foltran, J. Alsarraf, F. Robert, Y. Landais, E. Cloutet, H. Cramail, T. Tassaing, On the chemical fixation of supercritical carbon dioxide with epoxides catalyzed by ionic salts: an in situ FTIR and Raman study. Catal. Sci. Technol. 3, 1046–1055 (2013). https://doi.org/10.1039/c2cy20784b
J. Sun, J. Ren, S. Zhang, W. Cheng, Water as an efficient medium for the synthesis of cyclic carbonate. Tetrahedron Lett. 50, 423–426 (2009). https://doi.org/10.1016/j.tetlet.2008.11.034
X. Fu, P. Xie, Y. Lian, L. He, W. Zhao, T. Chang, S. Qin, Temperature-responsive self-separation ionic liquid system of zwitterionic-type quaternary ammonium-KI for CO2 fixation. Chin. J. Catal. 39, 1854–1860 (2018). https://doi.org/10.1016/S1872-2067(18)63101-8
M.O. Vieira, W.F. Monteiro, B.S. Neto, R. Ligabue, V.V. Chaban, S. Einloft, Surface active ionic liquids as catalyst for CO2 conversion to propylene carbonate. Catal. Lett. 148, 108–118 (2018). https://doi.org/10.1007/s10562-017-2212-4
M.O. Vieira, W.F. Monteiro, B.S. Neto, V.V. Chaban, R. Ligabue, S. Einloft, Chemical fixation of CO2: the influence of linear amphiphilic anions on surface active ionic liquids (SAILs) as catalysts for synthesis of cyclic carbonates under solvent-free conditions. React. Kinet. Mech. Catal. 126, 987–1001 (2019). https://doi.org/10.1007/s11144-019-01544-6
S. Wu, B. Wang, Y. Zhang, E.H.M. Elageed, H. Wu, G. Gao, Phenolic hydroxyl-functionalized imidazolium ionic liquids: highly efficient catalysts for the fixation of CO2 to cyclic carbonates. J. Mol. Catal. A Chem. 418–419, 1–8 (2016). https://doi.org/10.1016/j.molcata.2016.03.002
W.-L. Dai, B. Jin, Sh.-L. Luo, X.-B. Luo, X.-M. Tu, Ch.-T. Au, Functionalized phosphonium-based ionic liquids as efficient catalysts for the synthesis of cyclic carbonate from expoxides and carbon dioxide. Appl. Catal. A General 470, 183–188 (2014). https://doi.org/10.1016/j.apcata.2013.10.060
M.H. Anthofer, M.E. Wilhelm, M. Cokoja, M. Drees, W.A. Herrmann, F.E. Kühn, Hydroxy-functionalized imidazolium bromides as catalysts for the cycloaddition of CO2 and epoxides to cyclic carbonates. Chem. Cat. Chem. 7(1), 94–98 (2014). https://doi.org/10.1002/cctc.201402754
Z.-Z. Yang, Y.-N. Zhao, L.-N. He, CO2 chemistry: task-specific ionic liquids for CO2 capture/activation and subsequent conversion. RSC Adv. 1(4), 545–567 (2011). https://doi.org/10.1039/c1ra00307k
S. Yue, P. Wang, X. Hao, S. Zang, Dual amino-functionalized ionic liquids as efficient catalysts for carbonate synthesis from carbon dioxide and epoxide under solvent and cocatalyst-free conditions. J. CO2 Util. 21, 238–246 (2017). https://doi.org/10.1016/j.jcou.2017.07.017
W. Zhang, L. He, B. Zhang, Y. Wang, J. Luo, Y. Zhao, C. Li, Preparation of propylene carbonate catalyzed by ionic liquid. Chem. Papers 74, 2583–2590 (2020). https://doi.org/10.1007/s11696-020-01053-0
W. Li, W. Cheng, X. Yang, Q. Su, L. Dong, P. Zhang, Y. Yi, B. Li, S. Zhang, Synthesis of cyclic carbonate catalyzed by DBU derived basic ionic liquids. Chin. J. Chem. 36, 293–298 (2018). https://doi.org/10.1002/cjoc.201700747
C. Chen, Y. Ma, D. Zheng, L. Wang, J. Li, J. Zhang, S. Zhang, Insight into the role of weak interaction played in the fixation of CO2 catalyzed by the amino-functionalized imidazolium-based ionic liquids. J. CO2 Util. 18, 156–163 (2017). https://doi.org/10.1016/j.jcou.2017.01.026
V.B. Saptal, B.M. Bhanage, Bifunctional ionic liquids derived from biorenewable sources as sustainable catalysts for fixation of carbon dioxide. Chem. Sus. Chem. 10(6), 1145–1151 (2016). https://doi.org/10.1002/cssc.201601228
L.V. Nguyen, B. Lee, D.Q. Nguyen, M.-J. Kang, H. Lee, S. Ryu, H.S. Kim, J.S. Lee, Lithium chloride-imidazolium chloride melts for the coupling reactions of propylene oxide and CO2. Bull. Korean Chem. Soc. 29(1), 148–152 (2008). https://doi.org/10.5012/bkcs.2008.29.1.148
S. Zhang, S.J. Jin, Y.J. Kim, J. Hong, W. Lee, J.-B. Ryu, H.S. Kim, Highly active and non-corrosive catalytic systems for the coupling reactions of ethylene oxide and CO2. Bull. Korean Chem. Soc. 38(2), 219–223 (2017). https://doi.org/10.1002/bkcs.11068
A.-L. Girard, N. Simon, M. Zanatta, S. Marmitt, P. Gonçalves, J. Dupont, Insights on recyclable catalytic system composed of task-specific ionic liquids for the chemical fixation of carbon dioxide. Green Chem. 16(5), 2815–2825 (2014). https://doi.org/10.1039/c4gc00127c
T. Wang, D. Zheng, Y. Ma, J. Guo, Z. He, B. Ma, J. Zhang, Benzyl substituted imidazolium ionic liquids as efficient solvent-free catalysts for the cycloaddition of CO2 with epoxides: experimental and theoretic study. J. CO2 Util. 22, 44–52 (2017). https://doi.org/10.1016/j.jcou.2017.09.009
D. Zheng, J. Zhang, X. Zhu, T. Ren, L. Wang, J. Zhang, Solvent effects on the coupling reaction of CO2 with PO catalyzed by hydroxyl imidazolium ionic liquid: comparison of different models. J. CO2 Util. 27, 99–106 (2018). https://doi.org/10.1016/j.jcou.2018.07.005
J. Peng, S. Wang, H.-J. Yang, B. Ban, Z. Wei, L. Wang, B. Lei, Highly efficient fixation of carbon dioxide to cyclic carbonates with new multi-hydroxyl bis-(quaternary ammonium) ionic liquids as metal-free catalysts under mild conditions. Fuel 224, 481–488 (2018). https://doi.org/10.1016/j.fuel.2018.03.119
L. Ji, Z. Luo, Y. Zhang, R. Wang, Y. Ji, F. Xia, G. Gao, Imidazolium ionic liquids/organic bases: Efficient intermolecular synergistic catalysts for the cycloaddition of CO2 and epoxides under atmospheric pressure. Mol. Catal. 446, 124–130 (2018). https://doi.org/10.1016/j.mcat.2017.12.026
Y. Wang, J. Nie, C. Lu, F. Wang, C. Ma, Z. Chen, G. Yang, Imidazolium-based polymeric ionic liquids for heterogeneous catalytic conversion of CO2 into cyclic carbonates. Microporous Mesoporous Mater. 292(109751), 1–6 (2020). https://doi.org/10.1016/j.micromeso.2019.109751
X. Wang, Y. Zhou, Z. Guo, G. Chen, J. Li, Y. Shi, Y. Liu, J. Wang, Heterogeneous conversion of CO2 into cyclic carbonates at ambient pressure catalyzed by ionothermal–derived mesomacroporous hierarchical poly(ionic liquid)s. Chem. Sci. 6, 6916–6924 (2015). https://doi.org/10.1039/c5sc02050f
R. Qu, Z. Ren, N. Li, F. Zhang, Z.J. Zhang, H. Zhang, Solvent-Free cycloaddition of carbon dioxide and epichlorohydrin catalyzed by surface-attached imidazolium-type poly(ionic liquid) monolayers. J. CO2 Util. 38, 168–176 (2020). https://doi.org/10.1016/j.jcou.2020.01.022
D. Brühwiler, Postsynthetic functionalization of mesoporous silica. Nanoscale 2, 887–892 (2010). https://doi.org/10.1039/c0nr00039f
C. Kohrt, T. Werner, Recyclable bifunctional polystyrene and silica gel-supported organocatalyst for the coupling of CO2 with epoxides. Chem. Sus. Chem. 8, 2031–2034 (2015). https://doi.org/10.1002/cssc.201500128
A.R. Hajipour, Y. Heidari, G. Kozehgary, Silica grafted ammonium salts based on DABCO as heterogeneous catalysts for cyclic carbonate synthesis from carbon dioxide and epoxides. RSC Adv. 5, 22373–22379 (2015). https://doi.org/10.1039/c4ra16083e
M.V. Zakharova, F. Kleitz, F.-G. Fontaine, Carbon dioxide oversolubility in nanoconfined liquids for the synthesis of cyclic carbonates. Chem. Cat. Chem. 9, 1886–1890 (2017). https://doi.org/10.1002/cctc.201700247
J.M. Kolle, A. Sayari, Substrate dependence on the fixation of CO2 to cyclic carbonates over reusable porous hybrid solids. J CO2 Util. 26, 564–574 (2018). https://doi.org/10.1016/j.jcou.2018.06.013
M. Liu, B. Liu, L. Liang, F. Wang, L. Shi, J. Sun, Design of bifunctional NH3I-Zn/SBA-15 single-component heterogeneous catalyst for chemical fixation of carbon dioxide to cyclic carbonates. J. Mol. Catal. A Chem. 418–419, 78–85 (2016). https://doi.org/10.1016/j.molcata.2016.03.037
M. Liu, X. Lu, Y. Jiang, J. Sun, M. Arai, Zwitterionic imidazole-urea derivative framework bridged mesoporous hybrid silica: a highly efficient heterogeneous nanocatalyst for carbon dioxide conversion. Chem. Cat. Chem. 10, 1860–1868 (2018). https://doi.org/10.1002/cctc.201701492
A. Comès, X. Collard, L. Fusaro, L. Atzori, M.G. Cutrufello, C. Aprile, Bi-functional heterogeneous catalysts for carbon dioxide conversion: Enhanced performances at low temperature. RSC Adv. 8, 25342–25350 (2018). https://doi.org/10.1039/c8ra03878c
P. Agrigento, S.M. Al-Amsyar, B. Sorée, M. Taherimehr, M. Gruttadauria, C. Aprile, P.P. Pescarmona, Synthesis and high-throughput testing of multilayered supported ionic liquid catalysts for the conversion of CO2 and epoxides into cyclic carbonates. Catal. Sci. Technol. 4, 1598–1607 (2014). https://doi.org/10.1039/c3cy01000g
C. Calabrese, L.F. Liotta, F. Giacalone, M. Gruttadauria, C. Aprile, Supported polyhedral oligomeric silsesquioxane-based (POSS) materials as highly active organocatalysts for the conversion of CO2. Chem. Cat. Chem. 11, 560–567 (2019). https://doi.org/10.1002/cctc.201801351
J.H. Lee, A.S. Lee, J.-C. Lee, S.M. Hong, S.S. Hwang, C.M. Koo, Multifunctional mesoporous ionic gels and scaffolds derived from polyhedral oligomeric silsesquioxanes. ACS Appl. Mater. Interfaces 9, 3616–3623 (2017). https://doi.org/10.1021/acsami.6b12340
Q. Su, Y. Qi, X. Yao, W. Cheng, L. Dong, S. Chen, S. Zhang, Ionic liquids tailored and confined by one-step assembly with mesoporous silica for boosting the catalytic conversion of CO2 into cyclic carbonates. Green Chem. 20, 3232–3241 (2018). https://doi.org/10.1039/c8gc01038b
T. Takahashi, T. Watahiki, S. Kitazume, H. Yasuda, T. Sakakura, Synergistic hybrid catalyst for cyclic carbonate synthesis: remarkable acceleration caused by immobilization of homogeneous catalyst on silica. Chem. Commun. (2006). https://doi.org/10.1039/b517140g
T. Sakai, Y. Tsutsumi, T. Ema, Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides. Green Chem. 10, 337–341 (2008). https://doi.org/10.1039/b718321f
K. Motokura, S. Itagaki, Y. Iwasawa, A. Miyaji, T. Baba, Silica-supported aminopyridinium halides for catalytic transformations of epoxides to cyclic carbonates under atmospheric pressure of carbon dioxide. Green Chem. 11, 1876–1880 (2009). https://doi.org/10.1039/b916764c
R. Luo, X. Zhou, W. Zhang, Z. Liang, J. Jiang, H. Ji, New bi-functional zinc catalysts based on robust and easy-to-handle N-chelating ligands for the synthesis of cyclic carbonates from epoxides and CO2 under mild conditions. Green Chem. 16, 4179–4189 (2014). https://doi.org/10.1039/c4gc00671b
Y. Chen, R. Luo, Q. Xu, J. Jiang, X. Zhou, H. Ji, Metalloporphyrin polymers with intercalated ionic liquids for synergistic CO2 fixation via cyclic carbonate production. ACS Sustain. Chem. Eng. 6(1), 1074–1082 (2017). https://doi.org/10.1021/acssuschemeng.7b03371
K. Jasiak, A. Siewniak, K. Kopczynska, A. Chrobok, S. Baj, Hydrogensulphate ionic liquids as an efficient catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides. J. Chem. Technol. Biotechnol. 91, 2827–2833 (2016). https://doi.org/10.1002/jctb.4892
D. Kim, Y. Moon, D. Ji, H. Kim, D. Cho, Metal-containing ionic liquids as synergistic catalysts for the cycloaddition of CO2: a density functional theory and response surface methodology corroborated study. Sustain. Chem. Eng. 4(9), 4591–4600 (2016). https://doi.org/10.1021/acssuschemeng.6b00711
R. Ma, L.-N. He, Y.-B. Zhou, Efficient and recyclable tetraoxo-coordinated zinc catalyst for the cycloaddition of epoxides with carbon dioxide at atmospheric pressure. Green Chem. 18, 226–231 (2016). https://doi.org/10.1039/c5gc01826a
W. Wang, C. Li, L. Yan, Y. Wang, M. Jiang, Y. Ding, Ionic liquid/Zn-PPh3 integrated porous organic polymers featuring multifunctional sites: highly active heterogeneous catalyst for cooperative conversion of CO2 to cyclic carbonates. Catalysis 6, 6091–6100 (2016). https://doi.org/10.1021/acscatal.6b01142
Y. Xie, J. Liang, Y. Fu, J. Lin, H. Wang, S. Tu, J. Li, Poly(ionic liquid)s with high density of nucleophile/electrophile for CO2 fixation to cyclic carbonates at mild conditions. J. CO2 Util. 32, 281–289 (2019). https://doi.org/10.1016/j.jcou.2019.04.023
J. Chen, M. Zhong, L. Tao, L. Liu, S. Jayakumar, C. Li, Q. Yang, The cooperation of porphyrin-based porous polymer and thermal-responsive ionic liquid for efficient CO2 cycloaddition reaction. Green Chem. 20(4), 903–911 (2018). https://doi.org/10.1039/c7gc03801a
P. Li, Z. Cao, Catalytic coupling of CO2 with epoxide by metal macrocycles functionalized with the imidazolium bromide: insight into mechanism and activity regulation from density functional calculations. Dalton Trans. 48(4), 1344–1350 (2019). https://doi.org/10.1039/c8dt04684k
F. Wang, C. Xu, Z. Li, C. Xia, J. Chen, Mechanism and origins of enantioselectivity for [BMIM]Cl ionic liquids and ZnCl2 co-catalyzed coupling reaction of CO2 with epoxides. J. Mol. Catal. A: Chem. 385, 133–140 (2014). https://doi.org/10.1016/j.molcata.2014.01.024
J. Li, D. Jia, Z. Guo, Y. Liu, Y. Lyu, Y. Zhou, J. Wang, Imidazolinium based porous hypercrosslinked ionic polymers for efficient CO2 capture and fixation with epoxides. Green Chem. 19(11), 2675–2686 (2017). https://doi.org/10.1039/c7gc00105c
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Nasirov, F., Nasirli, E. & Ibrahimova, M. Cyclic carbonates synthesis by cycloaddition reaction of CO2 with epoxides in the presence of zinc-containing and ionic liquid catalysts. J IRAN CHEM SOC 19, 353–379 (2022). https://doi.org/10.1007/s13738-021-02330-9
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DOI: https://doi.org/10.1007/s13738-021-02330-9