[en] This review is dedicated to the state‐of‐the art routes used for the synthesis of CO2 ‐based
(a)cyclic carbonates and polycarbonates from alcohol substrates, with an emphasis on their respective main advantages and limitations. The first section reviews the synthesis of organic carbonates such as dialkyl carbonates or cyclic carbonates from the carbonation of alcohols. Many different synthetic strategies have been reported (dehydrative condensation, the alkylation route, the “leaving group” strategy, the carbodiimide route, the protected alcohols route, etc.) with various substrates (mono‐alcohols, diols, allyl alcohols, halohydrins, propargylic alcohols, etc.). The second section reviews the formation of polycarbonates via the direct copolymerization of CO2
with diols, as well as the ring‐opening polymerization route. Finally, polycondensation processes involving CO2-‐based dimethyl and diphenyl carbonates with aliphatic and aromatic diols are described.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM), Belgium Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Belgium
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Brege, Antoine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Grignard, Bruno ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Méreau, Raphaël; University of Bordeaux, CNRS, Institute of Molecular Sciences, Talence, France
Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Jérôme, Christine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Tassaing, Thierry; University of Bordeaux, CNRS, Institute of Molecular Sciences, Talence, France
Language :
English
Title :
En route to CO2-based (a)cyclic carbonates and polycarbonates from alcohols substrates by direct and indirect approaches
Publication date :
20 January 2022
Journal title :
Catalysts
eISSN :
2073-4344
Publisher :
MDPI AG, Basel, Switzerland
Volume :
12
Issue :
2
Pages :
124
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen EOS - The Excellence Of Science Program Région Nouvelle-Aquitaine
Stocker, T.F. Intergovernmental Panel on Climate Change 2013: Physical Science Basis, Contribution of Working Group I to the Fifth Assessment Report of the Intergovernmental Panel on Climate Change; Cambridge University Press: Cambridge, UK, 2013.
Friedlingstein, P.; O’sullivan, M.; Jones, M.W.; Andrew, R.M.; Hauck, J.; Olsen, A.; Peters, G.P.; Peters, W.; Pongratz, J.; Sitch, S.; et al. Global Carbon Budget 2020. Earth Syst. Sci. Data 2020, 12, 3269–3340.
Jackson, R.B.; Le Quéré, C.; Andrew, R.M.; Canadell, J.G.; Peters, G.P.; Roy, J.; Wu, L. Warning signs for stabilizing global CO2 emissions. Environ. Res. Lett. 2017, 12, 110202.
Artz, J.; Müller, T.E.; Thenert, K.; Kleinekorte, J.; Meys, R.; Sternberg, A.; Bardow, A.; Leitner, W. Sustainable Conversion of Carbon Dioxide: An Integrated Review of Catalysis and Life Cycle Assessment. Chem. Rev. 2018, 118, 434–504.
Maeda, C.; Miyazaki, Y.; Ema, T. Recent progress in catalytic conversions of carbon dioxide. Catal. Sci. Technol. 2014, 4, 1482– 1497.
Tappe, N.A.; Reich, R.M.; D’elia, V.; Kühn, F.E. Current advances in the catalytic conversion of carbon dioxide by molecular catalysts: An update. Dalton Trans. 2018, 47, 13281–13313.
Ruscic, B.; Feller, D.; Peterson, K.A. Active Thermochemical Tables: Dissociation energies of several homonuclear first‐row diatomics and related thermochemical values. Theor. Chem. Acc. 2013, 133, 1415.
Martín, C.; Fiorani, G.; Kleij, A.W. Recent Advances in the Catalytic Preparation of Cyclic Organic Carbonates. ACS Catal. 2015, 5, 1353–1370.
North, M.; Pasquale, R.; Young, C. Synthesis of cyclic carbonates from epoxides and CO2. Green Chem. 2010, 12, 1514–1539.
Alves, M.; Grignard, B.; Boyaval, A.; Méreau, R.; De Winter, J.; Gerbaux, P.; Detrembleur, C.; Tassaing, T.; Jérôme, C. Organocatalytic Coupling of CO2 with Oxetane. ChemSusChem 2017, 10, 1128–1138.
Rintjema, J.; Guo, W.; Martin, E.; Escudero‐Adan, E.C.; Kleij, A.W. Highly Chemoselective Catalytic Coupling of Substituted Oxetanes and Carbon Dioxide. Chem. Eur. J. 2015, 21, 10754–10762.
Katie, J.L.; Ian, D.V.I.; Michael, N.; Mani, S. Valorization of Carbon Dioxide into Oxazolidinones by Reaction with Aziridines. Curr. Green Chem. 2019, 6, 32–43.
Yang, Z.‐Z.; He, L.‐N.; Gao, J.; Liu, A.‐H.; Yu, B. Carbon dioxide utilization with C–N bond formation: Carbon dioxide capture and subsequent conversion. Energy Environ. Sci. 2012, 5, 6602.
Harder, A.; Escher, B.I.; Landini, P.; Tobler, N.B.; Schwarzenbach, R.P. Evaluation of Bioanalytical Assays for Toxicity Assessment and Mode of Toxic Action Classification of Reactive Chemicals. Environ. Sci. Technol. 2003, 37, 4962–4970.
Kostal, J.; Voutchkova‐Kostal, A.; Weeks, B.; Zimmerman, J.B.; Anastas, P.T. A Free Energy Approach to the Prediction of Olefin and Epoxide Mutagenicity and Carcinogenicity. Chem. Res. Toxicol. 2012, 25, 2780–2787.
Santos, B.a.V.; Silva, V.M.T.M.; Loureiro, J.M.; Barbosa, D.; Rodrigues, A.E. Modeling of physical and chemical equilibrium for the direct synthesis of dimethyl carbonate at high pressure conditions. Fluid Phase Equilib. 2012, 336, 41–51.
Santos, B.a.V.; Pereira, C.S.M.; Silva, V.M.T.M.; Loureiro, J.M.; Rodrigues, A.E. Kinetic study for the direct synthesis of dimethyl carbonate from methanol and CO2 over CeO2 at high pressure conditions. Appl. Catal. Gen. 2013, 455, 219–226.
Müller, K.; Mokrushina, L.; Arlt, W. Thermodynamic Constraints for the Utilization of CO2. Chem. Ing. Technol. 2014, 86, 497– 503.
Kizlink, J.; Pastucha, I. Preparation of Dimethyl Carbonate from Methanol and Carbon Dioxide in the Presence of Organotin Compounds. Collect. Czech. Chem. Commun. 1994, 59, 2116–2118.
Kizlink, J. Synthesis of Dimethyl Carbonate from Carbon Dioxide and Methanol in the Presence of Organotin Compounds. Collect. Czech. Chem. Commun. 1993, 58, 1399–1402.
Kizlink, J.; Pastucha, I. Preparation of Dimethyl Carbonate from Methanol and Carbon Dioxide in the Presence of Sn(IV) and Ti(IV) Alkoxides and Metal Acetates. Collect. Czech. Chem. Commun. 1995, 60, 687–692.
Zhao, T.; Han, Y.; Sun, Y. Novel reaction route for dimethyl carbonate synthesis from CO2 and methanol. Fuel Process. Technol. 2000, 62, 187–194.
Aresta, M.; Dibenedetto, A.; Pastore, C.; Pápai, I.; Schubert, G. Reaction mechanism of the direct carboxylation of methanol to dimethylcarbonate: Experimental and theoretical studies. Top. Catal. 2006, 40, 71–81.
Du, Y.; He, L.‐N.; Kong, D.‐L. Magnesium‐catalyzed synthesis of organic carbonate from 1,2‐diol/alcohol and carbon dioxide. Catal. Commun. 2008, 9, 1754–1758.
Tomishige, K.; Sakaihori, T.; Ikeda, Y.; Fujimoto, K. A novel method of direct synthesis of dimethyl carbonate from methanol and carbon dioxide catalyzed by zirconia. Catal. Lett. 1999, 58, 225–229.
Tomishige, K.; Ikeda, Y.; Sakaihori, T.; Fujimoto, K. Catalytic properties and structure of zirconia catalysts for direct synthesis of dimethyl carbonate from methanol and carbon dioxide. J. Catal. 2000, 192, 355–362.
Ballivet‐Tkatchenko, D.; Dos Santos, J.H.Z.; Philippot, K.; Vasireddy, S. Carbon dioxide conversion to dimethyl carbonate: The effect of silica as support for SnO2 and ZrO2 catalysts. Comptes Rendus Chim. 2011, 14, 780–785.
Ikeda, Y.; Asadullah, M.; Fujimoto, K.; Tomishige, K. Structure of the Active Sites on H3PO4/ZrO2 Catalysts for Dimethyl Carbonate Synthesis from Methanol and Carbon Dioxide. J. Phys. Chem. 2001, 105, 10653–10658.
Ikeda, Y.; Sakaihori, T.; Tomishige, K.; Fujimoto, K. Promoting effect of phosphoric acid on zirconia catalysts in selective synthesis of dimethyl carbonate from methanol and carbon dioxide. Catal. Lett. 2000, 66, 59–62.
Yoshida, Y.; Arai, Y.; Kado, S.; Kunimori, K.; Tomishige, K. Direct synthesis of organic carbonates from the reaction of CO2 with methanol and ethanol over CeO2 catalysts. Catal. Today 2006, 115, 95–101.
Wang, S.; Zhao, L.; Wang, W.; Zhao, Y.; Zhang, G.; Ma, X.; Gong, J. Morphology control of ceria nanocrystals for catalytic conversion of CO2 with methanol. Nanoscale 2013, 5, 5582–5588.
Zhang, Z.‐F.; Liu, Z.‐T.; Liu, Z.‐W.; Lu, J. DMC Formation over Ce0.5Zr0.5O2 Prepared by Complex‐decomposition Method. Catal. Lett. 2009, 129, 428–436.
Lee, H.J.; Park, S.; Song, I.K.; Jung, J.C. Direct Synthesis of Dimethyl Carbonate from Methanol and Carbon Dioxide over Ga2O3/Ce0.6Zr0.4O2 Catalysts: Effect of Acidity and Basicity of the Catalysts. Catal. Lett. 2011, 141, 531–537.
Lee, H.J.; Park, S.; Jung, J.C.; Song, I.K. Direct synthesis of dimethyl carbonate from methanol and carbon dioxide over H3PW12O40/CeXZr1−XO2 catalysts: Effect of acidity of the catalysts. Korean J. Chem. Eng. 2011, 28, 1518–1522.
Zhou, Y.; Wang, S.; Xiao, M.; Han, D.; Lu, Y.; Meng, Y. Novel Cu–Fe bimetal catalyst for the formation of dimethyl carbonate from carbon dioxide and methanol. RSC Adv. 2012, 2, 6831–6837.
Bian, J.; Xiao, M.; Wang, S.J.; Lu, Y.X.; Meng, Y.Z. Graphite oxide as a novel host material of catalytically active Cu–Ni bimetallic nanoparticles. Catal. Commun. 2009, 10, 1529–1533.
Bian, J.; Wei, X.W.; Wang, L.; Guan, Z.P. Graphene nanosheet as support of catalytically active metal particles in DMC synthesis. Chin. Chem. Lett. 2011, 22, 57–60.
La, K.W.; Youn, M.H.; Chung, J.S.; Baeck, S.H.; Song, I.K. Synthesis of Dimethyl Carbonate from Methanol and Carbon Dioxide by Heteropolyacid/Metal Oxide Catalysts. Solid State Phenom. 2007, 119, 287–290.
Li, C.‐F.; Zhong, S.‐H. Study on application of membrane reactor in direct synthesis DMC from CO2 and CH3OH over Cu– KF/MgSiO catalyst. Catal. Today 2003, 82, 83–90.
Choi, J.‐C.; He, L.‐N.; Yasuda, H.; Sakakura, T. Selective and high yield synthesis of dimethyl carbonate directly from carbon dioxide and methanol. Green Chem. 2002, 4, 230–234.
George, J.; Patel, Y.; Pillai, S.M.; Munshi, P. Methanol assisted selective formation of 1,2‐glycerol carbonate from glycerol and carbon dioxide using nBu2SnO as a catalyst. J. Mol. Catal. Chem. 2009, 304, 1–7.
Iwakabe, K.; Nakaiwa, M.; Sakakura, T.; Choi, J.‐C.; Yasuda, H.; Takahashi, T.; Ooshima, Y. Reaction Rate of the Production of Dimethyl Carbonate Directly from the Supercritical CO2 and Methanol. J. Chem. Eng. Jpn. 2005, 38, 1020–1024.
Zhang, Z.; Liu, S.; Zhang, L.; Yin, S.; Yang, G.; Han, B. Driving dimethyl carbonate synthesis from CO2 and methanol and production of acetylene simultaneously using CaC2. Chem. Commun. 2018, 54, 4410–4412.
Tamura, M.; Satsuma, A.; Shimizu, K.‐I. CeO2‐catalyzed nitrile hydration to amide: Reaction mechanism and active sites. Catal. Sci. Technol. 2013, 3, 1386–1393.
Tomishige, K.; Furusawa, Y.; Ikeda, Y.; Asadullah, M.; Fujimoto, K. CeO2–ZrO2 Solid Solution Catalyst for Selective Synthesis of Dimethyl Carbonate from Methanol and Carbon Dioxide. Catal. Lett. 2001, 76, 71–74.
Lamotte, J.; Morávek, V.; Bensitel, M.; Lavalley, J.C. FT‐IR study of the structure and reactivity of methoxy species on ThO2 and CeO2. React. Kinet. Catal. Lett. 1988, 36, 113–118.
Badri, A.; Binet, C.; Lavalley, J.‐C. Use of methanol as an IR molecular probe to study the surface of polycrystalline ceria. J. Chem. Soc. Faraday Trans. 1997, 93, 1159–1168.
Binet, C.; Daturi, M.; Lavalley, J.‐C. IR study of polycrystalline ceria properties in oxidised and reduced states. Catal. Today 1999, 50, 207–225.
Honda, M.; Kuno, S.; Begum, N.; Fujimoto, K.‐I.; Suzuki, K.; Nakagawa, Y.; Tomishige, K. Catalytic synthesis of dialkyl carbonate from low pressure CO2 and alcohols combined with acetonitrile hydration catalyzed by CeO2. Appl. Catal. Gen. 2010, 384, 165–170.
Honda, M.; Suzuki, A.; Noorjahan, B.; Fujimoto, K.‐I.; Suzuki, K.; Tomishige, K. Low pressure CO2 to dimethyl carbonate by the reaction with methanol promoted by acetonitrile hydration. Chem. Commun. 2009, 30, 4596–4598. https://doi.org/10.1039/B909610H.
Honda, M.; Kuno, S.; Sonehara, S.; Fujimoto, K.‐I.; Suzuki, K.; Nakagawa, Y.; Tomishige, K. Tandem Carboxylation‐Hydration Reaction System from Methanol, CO2 and Benzonitrile to Dimethyl Carbonate and Benzamide Catalyzed by CeO2. ChemCatChem 2011, 3, 365–370.
Tamura, M.; Shimizu, K.‐I.; Satsuma, A. Comprehensive IR study on acid/base properties of metal oxides. Appl. Catal. Gen. 2012, 4339, 135–145.
Honda, M.; Tamura, M.; Nakagawa, Y.; Sonehara, S.; Suzuki, K.; Fujimoto, K.‐I.; Tomishige, K. Ceria‐Catalyzed Conversion of Carbon Dioxide into Dimethyl Carbonate with 2‐Cyanopyridine. ChemSuschem 2013, 6, 1341–1344.
Honda, M.; Tamura, M.; Nakagawa, Y.; Nakao, K.; Suzuki, K.; Tomishige, K. Organic carbonate synthesis from CO2 and alcohol over CeO2 with 2‐cyanopyridine: Scope and mechanistic studies. J. Catal. 2014, 318, 95–107.
Salvatore, R.N.; Chu, F.; Nagle, A.S.; Kapxhiu, E.A.; Cross, R.M.; Jung, K.W. Efficient Cs2CO3‐promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI. Tetrahedron 2002, 58, 3329–3347.
Shi, M.; Shen, Y.‐M. Synthesis of Mixed Carbonates via a Three‐Component Coupling of Alcohols, CO2, and Alkyl Halides in the Presence of K2CO3 and Tetrabutylammonium Iodide. Molecules 2002, 7, 386–393.
Lethesh, K.C.; Shah, S.N.; Mutalib, M.I.A. Synthesis, Characterization, and Thermophysical Properties of 1,8‐ Diazobicyclo[5.4.0]undec‐7‐ene Based Thiocyanate Ionic Liquids. J. Chem. Eng. Data 2014, 59, 1788–1795.
Wang, Y.; Han, Q.; Wen, H. Theoretical discussion on the mechanism of binding CO2by DBU and alcohol. Mol. Simul. 2013, 39, 822–827.
Villiers, C.; Dognon, J.‐P.; Pollet, R.; Thuéry, P.; Ephritikhine, M. An Isolated CO2 Adduct of a Nitrogen Base: Crystal and Electronic Structures. Angew. Chem. Int. Ed. 2010, 49, 3465–3468.
Ma, J.; Zhang, X.; Zhao, N.; Al‐Arifi, A.S.N.; Aouak, T.; Al‐Othman, Z.A.; Xiao, F.; Wei, W.; Sun, Y. Theoretical study of TBD-catalyzed carboxylation of propylene glycol with CO2. J. Mol. Catal. Chem. 2010, 315, 76–81.
Goodrich, P.; Gunaratne, H.Q.N.; Jin, L.; Lei, Y.; Seddon, K.R. Carbon Dioxide Utilisation for the Synthesis of Unsymmetrical Dialkyl and Cyclic Carbonates Promoted by Basic Ionic Liquids. Aust. J. Chem. 2018, 71, 181–185.
Lim, Y.N.; Lee, C.; Jang, H.‐Y. Metal‐Free Synthesis of Cyclic and Acyclic Carbonates from CO2and Alcohols. Eur. J. Org. Chem. 2014, 2014, 1823–1826.
Aresta, M.; Dibenedetto, A.; Fracchiolla, E.; Giannoccaro, P.; Pastore, C.; Pápai, I.; Schubert, G. Mechanism of Formation of Organic Carbonates from Aliphatic Alcohols and Carbon Dioxide under Mild Conditions Promoted by Carbodiimides. DFT Calculation and Experimental Study. J. Org. Chem. 2005, 70, 6177–6186.
Däbritz, E. Syntheses and Reactions of O,N,N′‐Trisubstituted Isoureas. Angew. Chem. Int. Ed. Engl. 1966, 5, 470–477.
Imberdis, A.; Lefèvre, G.; Thuéry, P.; Cantat, T. Metal‐Free and Alkali‐Metal‐Catalyzed Synthesis of Isoureas from Alcohols and Carbodiimides. Angew. Chem. 2018, 130, 3138–3142.
Wang, S.; Zhou, J.; Zhao, S.; Zhao, Y.; Ma, X. Enhancement of Dimethyl Carbonate Synthesis with In Situ Hydrolysis of 2,2‐ Dimethoxy Propane. Chem. Eng. Technol. 2016, 39, 723–729.
Tomishige, K.; Kunimori, K. Catalytic and direct synthesis of dimethyl carbonate starting from carbon dioxide using CeO2‐ZrO2 solid solution heterogeneous catalyst: Effect of H2O removal from the reaction system. Appl. Catal. Gen. 2002, 237, 103–109.
Chang, T.; Tamura, M.; Nakagawa, Y.; Fukaya, N.; Choi, J.‐C.; Mishima, T.; Matsumoto, S.; Hamura, S.; Tomishige, K. An effective combination catalyst of CeO2 and zeolite for the direct synthesis of diethyl carbonate from CO2 and ethanol with 2,2‐ diethoxypropane as a dehydrating agent. Green Chem. 2020, 22, 7321–7327.
Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.‐C.; Sako, T. Selective Conversion of Carbon Dioxide to Dimethyl Carbonate by Molecular Catalysis. J. Org. Chem. 1998, 63, 7095–7096.
Zhang, Z.‐F.; Liu, Z.‐W.; Lu, J.; Liu, Z.‐T. Synthesis of Dimethyl Carbonate from Carbon Dioxide and Methanol over CexZr1‐xO2 and [EMIM]Br/Ce0.5Zr0.5O2. Ind. Eng. Chem. Res. 2011, 50, 1981–1988.
Guidi, S.; Calmanti, R.; Noè, M.; Perosa, A.; Selva, M. Thermal (Catalyst‐Free) Transesterification of Diols and Glycerol with Dimethyl Carbonate: A Flexible Reaction for Batch and Continuous‐Flow Applications. ACS Sustain. Chem. Eng. 2016, 4, 6144– 6151.
Baral, E.R.; Lee, J.H.; Kim, J.G. Diphenyl Carbonate: A Highly Reactive and Green Carbonyl Source for the Synthesis of Cyclic Carbonates. J. Org. Chem. 2018, 83, 11768–11776.
Ochoa‐Gómez, J.R.; Gómez‐Jiménez‐Aberasturi, O.; Ramírez‐López, C.; Maestro‐Madurga, B. Synthesis of glycerol 1,2‐ carbonate by transesterification of glycerol with dimethyl carbonate using triethylamine as a facile separable homogeneous catalyst. Green Chem. 2012, 14, 3368.
Schutyser, W.; Van Den Bosch, S.; Renders, T.; De Boe, T.; Koelewijn, S.F.; Dewaele, A.; Ennaert, T.; Verkinderen, O.; Goderis, B.; Courtin, C.M.; et al. Influence of bio‐based solvents on the catalytic reductive fractionation of birch wood. Green Chem. 2015, 17, 5035–5045.
Koelewijn, S.F.; Van Den Bosch, S.; Renders, T.; Schutyser, W.; Lagrain, B.; Smet, M.; Thomas, J.; Dehaen, W.; Van Puyvelde, P.; Witters, H.; et al. Sustainable bisphenols from renewable softwood lignin feedstock for polycarbonates and cyanate ester resins. Green Chem. 2017, 19, 2561–2570.
Ma, J.; Liu, J.; Zhang, Z.; Han, B. Mechanisms of ethylene glycol carbonylation with carbon dioxide. Comput. Theor. Chem. 2012, 992, 103–109.
Aresta, M.; Dibenedetto, A.; Nocito, F.; Pastore, C. A study on the carboxylation of glycerol to glycerol carbonate with carbon dioxide: The role of the catalyst, solvent and reaction conditions. J. Mol. Catal. Chem. 2006, 257, 149–153.
Tamura, M.; Honda, M.; Nakagawa, Y.; Tomishige, K. Direct conversion of CO2 with diols, aminoalcohols and diamines to cyclic carbonates, cyclic carbamates and cyclic ureas using heterogeneous catalysts. J. Chem. Technol. Biotechnol. 2014, 89, 19–33.
Su, X.; Lin, W.; Cheng, H.; Zhang, C.; Wang, Y.; Yu, X.; Wu, Z.; Zhao, F. Metal‐free catalytic conversion of CO2and glycerol to glycerol carbonate. Green Chem. 2017, 19, 1775–1781.
Honda, M.; Tamura, M.; Nakao, K.; Suzuki, K.; Nakagawa, Y.; Tomishige, K. Direct Cyclic Carbonate Synthesis from CO2 and Diol over Carboxylation/Hydration Cascade Catalyst of CeO2 with 2‐Cyanopyridine. ACS Catal. 2014, 4, 1893–1896.
Huang, S.; Ma, J.; Li, J.; Zhao, N.; Wei, W.; Sun, Y. Efficient propylene carbonate synthesis from propylene glycol and carbon dioxide via organic bases. Catal. Commun. 2008, 9, 276–280.
Kitamura, T.; Inoue, Y.; Maeda, T.; Oyamada, J. Convenient synthesis of ethylene carbonates from carbon dioxide and 1,2‐diols at atmospheric pressure of carbon dioxide. Synth. Commun. 2015, 46, 39–45.
Gregory, G.L.; Ulmann, M.; Buchard, A. Synthesis of 6‐membered cyclic carbonates from 1,3‐diols and low CO2 pressure: A novel mild strategy to replace phosgene reagents. RSC Adv. 2015, 5, 39404–39408.
Reithofer, M.R.; Sum, Y.N.; Zhang, Y. Synthesis of cyclic carbonates with carbon dioxide and cesium carbonate. Green Chem. 2013, 15, 2086–2090.
Mcguire, T.M.; López‐Vidal, E.M.; Gregory, G.L.; Buchard, A. Synthesis of 5‐ to 8‐membered cyclic carbonates from diols and CO2: A one‐step, atmospheric pressure and ambient temperature procedure. J. CO2 Util. 2018, 27, 283–288.
Brege, A.; Méreau, R.; Mcgehee, K.; Grignard, B.; Detrembleur, C.; Jerome, C.; Tassaing, T. The coupling of CO2 with diols promoted by organic dual systems: Towards products divergence via benchmarking of the performance metrics. J. CO2 Util. 2020, 38, 88–98.
Voutchkova, A.M.; Feliz, M.; Clot, E.; Eisenstein, O.; Crabtree, R.H. Imidazolium Carboxylates as Versatile and Selective N‐ Heterocyclic Carbene Transfer Agents: Synthesis, Mechanism, and Applications. J. Am. Chem. Soc. 2007, 129, 12834–12846.
Riduan, S.N.; Zhang, Y.; Ying, J.Y. Conversion of Carbon Dioxide into Methanol with Silanes over N‐Heterocyclic Carbene Catalysts. Angew. Chem. Int. Ed. 2009, 48, 3322–3325.
Bobbink, F.D.; Gruszka, W.; Hulla, M.; Das, S.; Dyson, P.J. Synthesis of cyclic carbonates from diols and CO2 catalyzed by carbenes. Chem. Commun. 2016, 52, 10787–10790.
Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. A new regio‐ and stereo‐selective functionalization of allylic and homoallylic alcohols. J. Chem. Soc. Chem. Commun. 1981, 10, 465–466. https://doi.org/10.1039/c39810000465.
Vara, B.A.; Struble, T.J.; Wang, W.; Dobish, M.C.; Johnston, J.N. Enantioselective Small Molecule Synthesis by Carbon Dioxide Fixation using a Dual Brønsted Acid/Base Organocatalyst. J. Am. Chem. Soc. 2015, 137, 7302–7305.
Minakata, S.; Sasaki, I.; Ide, T. Atmospheric CO2 Fixation by Unsaturated Alcohols Using tBuOI under Neutral Conditions. Angew. Chem. Int. Ed. 2010, 49, 1309–1311.
Wang, J.‐L.; He, L.‐N.; Dou, X.‐Y.; Wu, F. Poly(ethylene glycol): An Alternative Solvent for the Synthesis of Cyclic Carbonate from Vicinal Halohydrin and Carbon Dioxide. Aust. J. Chem. 2009, 62, 917–920.
Eghbali, N.; Li, C.‐J. Conversion of carbon dioxide and olefins into cyclic carbonates in water. Green Chem. 2007, 9, 213–215.
March’s Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 5th ed.; Smith, M.B., March, J., Eds.; Wiley Interscience: New York, NY, USA, 2001; ISBN 0‐471‐58589‐0.
Lang, X.D.; He, L.N. Green Catalytic Process for Cyclic Carbonate Synthesis from Carbon Dioxide under Mild Conditions. Chem Rec. 2016, 16, 1337–1352.
Kayaki, Y.; Yamamoto, M.; Ikariya, T. Stereoselective Formation of α‐Alkylidene Cyclic Carbonates via Carboxylative Cyclization of Propargyl Alcohols in Supercritical Carbon Dioxide. J. Org. Chem. 2007, 72, 647–649.
Sun, Y.‐L.; Wei, Y.; Shi, M. Phosphine‐catalyzed fixation of CO2 with γ‐hydroxyl alkynone under ambient temperature and pressure: Kinetic resolution and further conversion. Org. Chem. Front. 2019, 6, 2420–2429.
Kayaki, Y.; Yamamoto, M.; Ikariya, T. N‐Heterocyclic Carbenes as Efficient Organocatalysts for CO2 Fixation Reactions. Angew. Chem. Int. Ed. 2009, 48, 4194–4197.
Li, W.; Yang, N.; Lyu, Y. Theoretical Insights into the Catalytic Mechanism of N‐Heterocyclic Olefins in Carboxylative Cyclization of Propargyl Alcohol with CO2. J. Org. Chem. 2016, 81, 5303–5313.
Yan, Z.‐E.; Huo, R.‐P.; Guo, L.‐H.; Zhang, X. The mechanisms for N‐heterocyclic olefin‐catalyzed formation of cyclic carbonate from CO2 and propargylic alcohols. J. Mol. Model. 2016, 22, 94.
Li, W.; Huang, D.; Lyu, Y. A comparative computational study of N‐heterocyclic olefin and N‐heterocyclic carbene mediated carboxylative cyclization of propargyl alcohols with CO2. Org. Biomol. Chem. 2016, 14, 10875–10885.
Boyaval, A.; Méreau, R.; Grignard, B.; Detrembleur, C.; Jerome, C.; Tassaing, T. Organocatalytic Coupling of CO2 with a Propargylic Alcohol: A Comprehensive Mechanistic Study. ChemSusChem 2017, 10, 1241–1248.
Méreau, R.; Grignard, B.; Boyaval, A.; Detrembleur, C.; Jerome, C.; Tassaing, T. Tetrabutylammonium Salts: Cheap Catalysts for the Facile and Selective Synthesis of α‐Alkylidene Cyclic Carbonates from Carbon Dioxide and Alkynols. ChemCatChem 2018, 10, 956–960.
Grignard, B.; Ngassamtounzoua, C.; Gennen, S.; Gilbert, B.; Méreau, R.; Jerome, C.; Tassaing, T.; Detrembleur, C. Boosting the Catalytic Performance of Organic Salts for the Fast and Selective Synthesis of α‐Alkylidene Cyclic Carbonates from Carbon Dioxide and Propargylic Alcohols. ChemCatChem 2018, 10, 2584–2592.
Gennen, S.; Grignard, B.; Tassaing, T.; Jerome, C.; Detrembleur, C. CO2‐Sourced alpha‐Alkylidene Cyclic Carbonates: A Step Forward in the Quest for Functional Regioregular Poly(urethane)s and Poly(carbonate)s. Angew. Chem. Int. Ed. Engl. 2017, 56, 10394–10398.
Qiu, J.; Zhao, Y.; Li, Z.; Wang, H.; Fan, M.; Wang, J. Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO2 into α‐Alkylidene Cyclic Carbonates. ChemSuschem 2017, 10, 1120–1127.
Chen, K.; Shi, G.; Dao, R.; Mei, K.; Zhou, X.; Li, H.; Wang, C. Tuning the basicity of ionic liquids for efficient synthesis of alkylidene carbonates from CO2 at atmospheric pressure. Chem. Commun. 2016, 52, 7830–7833.
Hu, Y.; Song, J.; Xie, C.; Wu, H.; Jiang, T.; Yang, G.; Han, B. Transformation of CO2 into α‐Alkylidene Cyclic Carbonates at Room Temperature Cocatalyzed by CuI and Ionic Liquid with Biomass‐Derived Levulinate Anion. ACS Sustain. Chem. Eng. 2019, 7, 5614–5619.
Ouyang, L.; Tang, X.; He, H.; Qi, C.; Xiong, W.; Ren, Y.; Jiang, H. Copper‐Promoted Coupling of Carbon Dioxide and Propargylic Alcohols: Expansion of Substrate Scope and Trapping of Vinyl Copper Intermediate. Adv. Synth. Catal. 2015, 357, 2556–2565.
Yamada, T.; Ugajin, R.; Kikuchi, S. Silver‐Catalyzed Efficient Synthesis of Vinylene Carbonate Derivatives from Carbon Dioxide. Synlett 2014, 25, 1178–1180.
Yuan, Y.; Xie, Y.; Zeng, C.; Song, D.; Chaemchuen, S.; Chen, C.; Verpoort, F. A recyclable AgI/OAc− catalytic system for the efficient synthesis of α‐alkylidene cyclic carbonates: Carbon dioxide conversion at atmospheric pressure. Green Chem. 2017, 19, 2936–2940.
Li, J.‐Y.; Han, L.‐H.; Xu, Q.‐C.; Song, Q.‐W.; Liu, P.; Zhang, K. Cascade Strategy for Atmospheric Pressure CO2 Fixation to Cyclic Carbonates via Silver Sulfadiazine and Et4NBr Synergistic Catalysis. ACS Sustain. Chem. Eng. 2019, 7, 3378–3388.
Yuan, Y.; Xie, Y.; Song, D.; Zeng, C.; Chaemchuen, S.; Chen, C.; Verpoort, F. One‐pot carboxylative cyclization of propargylic alcohols and CO2 catalysed by N‐heterocyclic carbene/Ag systems. Appl. Organomet. Chem. 2017, 31, e3867.
Cui, M.; Qian, Q.; He, Z.; Ma, J.; Kang, X.; Hu, J.; Liu, Z.; Han, B. Synthesizing Ag Nanoparticles of Small Size on a Hierarchical Porosity Support for the Carboxylative Cyclization of Propargyl Alcohols with CO2 under Ambient Conditions. Chem.–A Eur. J. 2015, 21, 15924–15928.
Yang, Z.; Yu, B.; Zhang, H.; Zhao, Y.; Chen, Y.; Ma, Z.; Ji, G.; Gao, X.; Han, B.; Liu, Z. Metalated Mesoporous Poly(triphenylphosphine) with Azo Functionality: Efficient Catalysts for CO2 Conversion. ACS Catal. 2016, 6, 1268–1273.
Zhou, Z.; He, C.; Yang, L.; Wang, Y.; Liu, T.; Duan, C. Alkyne Activation by a Porous Silver Coordination Polymer for Heterogeneous Catalysis of Carbon Dioxide Cycloaddition. ACS Catal. 2017, 7, 2248–2256.
Dabral, S.; Bayarmagnai, B.; Hermsen, M.; Schießl, J.; Mormul, V.; Hashmi, A.S.K.; Schaub, T. Silver‐Catalyzed Carboxylative Cyclization of Primary Propargyl Alcohols with CO2. Org. Lett. 2019, 21, 1422–1425.
Jung, M.E.; Piizzi, G. gem‐Disubstituent Effect: Theoretical Basis and Synthetic Applications. Chem. Rev. 2005, 105, 1735–1766.
Islam, S.S.; Salam, N.; Molla, R.A.; Riyajuddin, S.; Yasmin, N.; Das, D.; Ghosh, K.; Islam, S.M. Zinc (II) incorporated porous organic polymeric material (POPs): A mild and efficient catalyst for synthesis of dicoumarols and carboxylative cyclization of propargyl alcohols and CO2 in ambient conditions. Mol. Catal. 2019, 477, 110541.
Hu, J.; Ma, J.; Zhu, Q.; Qian, Q.; Han, H.; Mei, Q.; Han, B. Zinc(ii)‐catalyzed reactions of carbon dioxide and propargylic alcohols to carbonates at room temperature. Green Chem. 2016, 18, 382–385.
Ma, J.; Lu, L.; Mei, Q.; Zhu, Q.; Hu, J.; Han, B. ZnI2/NEt3‐Catalyzed Cycloaddition of CO2 with Propargylic Alcohols: Computational Study on Mechanism. ChemCatChem 2017, 9, 4090–4097.
Tamura, M.; Ito, K.; Honda, M.; Nakagawa, Y.; Sugimoto, H.; Tomishige, K. Direct Copolymerization of CO2 and Diols. Sci. Rep. 2016, 6, 24038.
Gu, Y.; Matsuda, K.; Nakayama, A.; Tamura, M.; Nakagawa, Y.; Tomishige, K. Direct Synthesis of Alternating Polycarbonates from CO2 and Diols by Using a Catalyst System of CeO2 and 2‐Furonitrile. ACS Sustain. Chem. Eng. 2019, 7, 6304–6315.
Gong, Z.‐J.; Li, Y.‐R.; Wu, H.‐L.; Lin, S.D.; Yu, W.‐Y. Direct copolymerization of carbon dioxide and 1,4‐butanediol enhanced by ceria nanorod catalyst. Appl. Catal. B: Environ. 2020, 265, 118524.
Kadokawa, J.‐I.; Habu, H.; Fukamachi, S.; Karasu, M.; Tagaya, H.; Chiba, K. Direct polycondensation of carbon dioxide with xylylene glycols: A new method for the synthesis of polycarbonates. Macromol. Rapid Commun. 1998, 19, 657–660.
Kadokawa, J.‐I.; Fukamachi, S.; Tagaya, H.; Chiba, K. Direct Polycondensation of Carbon Dioxide with Various Diols Using the Triphenylphosphine/Bromotrichloromethane/N‐Cyclohexyl‐N′, N′, N′′, N′′‐tetramethylguanidine System as Condensing Agent. Polym. J. 2000, 32, 703.
Bian, S.; Pagan, C.; Andrianova “Artemyeva”, A.A.; Du, G. Synthesis of Polycarbonates and Poly(ether carbonate)s Directly from Carbon Dioxide and Diols Promoted by a Cs2CO3/CH2Cl2 System. ACS Omega 2016, 1, 1049–1057.
Pati, D.; Chen, Z.; Feng, X.; Hadjichristidis, N.; Gnanou, Y. Synthesis of polyglycocarbonates through polycondensation of glucopyranosides with CO2. Polym. Chem. 2017, 8, 2640–2646.
Soga, K.; Toshida, Y.; Hosoda, S.; Ikeda, S. A convenient synthesis of a polycarbonate. Makromol. Chem. 1977, 178, 2747–2751.
Soga, K.; Toshida, Y.; Hosoda, S.; Ikeda, S. Synthesis of a polycarbonate directly from carbon dioxide, alkali metal diolates and α,ω‐dihalo compounds. Makromol. Chem. 1978, 179, 2379–2386.
Chen, Z.; Hadjichristidis, N.; Feng, X.; Gnanou, Y. Cs2CO3‐promoted polycondensation of CO2 with diols and dihalides for the synthesis of miscellaneous polycarbonates. Polym. Chem. 2016, 7, 4944–4952.
Bian, S.; Andrianova, A.A.; Kubatova, A.; Du, G. Effect of dihalides on the polymer linkages in the Cs2CO3‐promoted polycondensation of 1 atm carbon dioxide and diols. Mater. Today Commun. 2019, 18, 100–109. https://doi.org/10.1016/j.mtcomm.2018.11.007.
Höcker, H.; Keul, H.; Kühling, S.; Hovestadt, W.; Müller, A.; Wurm, B. Ring‐opening polymerization and copolymerization of cyclic carbonates with a variety of initiating systems. Makromol. Chem. Macromol. Symp. 1993, 73, 1–5.
Rokicki, G. Aliphatic cyclic carbonates and spiroorthocarbonates as monomers. Prog. Polym. Sci. 2000, 25, 259–342.
Vogdanis, L.; Heitz, W. Carbon dioxide as a monomer, 3. The polymerization of ethylene carbonate. Die Makromol. Chem. Rapid Commun. 1986, 7, 543–547.
Vogdanis, L.; Martens, B.; Uchtmann, H.; Hensel, F.; Heitz, W. Synthetic and thermodynamic investigations in the polymerization of ethylene carbonate. Die Makromol. Chem. 1990, 191, 465–472.
Storey, R.F.; Hoffman, D.C. Formation of poly(ethylene ether carbonate) diols: Proposed mechanism and kinetic analysis. Macromolecules 1992, 25, 5369–5382.
Kricheldorf, H.R.; Jonté, J.M.; Berl, M. Polylactones 3. Copolymerization of glycolide with L, L‐lactide and other lactones. Die Makromol. Chem. 1985, 12, 25–38.
Kricheldorf, H.R.; Berl, M.; Scharnagl, N. Poly(lactones). 9. Polymerization mechanism of metal alkoxide initiated polymerizations of lactide and various lactones. Macromolecules 1988, 21, 286–293.
Lee, J.‐C.; Litt, M.H. Ring‐Opening Polymerization of Ethylene Carbonate and Depolymerization of Poly(ethylene oxide‐co-ethylene carbonate). Macromolecules 2000, 33, 1618–1627.
Yang, H.; Yan, M.; Pispas, S.; Zhang, G. Synthesis of Poly[(ethylene carbonate)‐co‐(ethylene oxide)] Copolymer by Phosphazene‐ Catalyzed ROP. Macromol. Chem. Phys. 2011, 212, 2589–2593.
Soga, K.; Tazuke, Y.; Hosoda, S.; Ikeda, S. Polymerization of propylene carbonate. J. Polym. Sci. Polym. Chem. Ed. 1977, 15, 219– 229.
Tezuka, K.; Komatsu, K.; Haba, O. The anionic ring‐opening polymerization of five‐membered cyclic carbonates fused to the cyclohexane ring. Polym. J. 2013, 45, 1183–1187.
Haba, O.; Tomizuka, H.; Endo, T. Anionic Ring‐Opening Polymerization of Methyl 4,6‐O‐Benzylidene‐2,3‐O‐ carbonyl‐α‐d-glucopyranoside: A First Example of Anionic Ring‐Opening Polymerization of Five‐Membered Cyclic Carbonate without Elimination of CO2. Macromolecules 2005, 38, 3562–3563.
Guerin, W.; Diallo, A.K.; Kirilov, E.; Helou, M.; Slawinski, M.; Brusson, J.‐M.; Carpentier, J.‐F.; Guillaume, S.M. Enantiopure Isotactic PCHC Synthesized by Ring‐Opening Polymerization of Cyclohexene Carbonate. Macromolecules 2014, 47, 4230–4235.
Azechi, M.; Matsumoto, K.; Endo, T. Anionic ring‐opening polymerization of a five‐membered cyclic carbonate having a glucopyranoside structure. J. Polym. Sci. Part A Polym. Chem. 2013, 51, 1651–1655.
Rokicki, G.; Parzuchowski, P.G. In Polymer Science: A Comprehensive Reference; Matyjaszewski, K., Möller, M., Eds.; Elsevier, Amsterdam, The Netherlands, 2012; pp. 247–308. https://doi.org/10.1016/B978‐0‐444‐53349‐4.00107‐2.
Kricheldorf, H.R.; Jenssen, J. Polylactones. 16. Cationic Polymerization of Trimethylene Carbonate and Other Cyclic Carbonates. J. Macromol. Sci. Part A—Chem. 1989, 26, 631–644.
Ariga, T.; Takata, T.; Endo, T. Cationic Ring‐Opening Polymerization of Cyclic Carbonates with Alkyl Halides To Yield Polycarbonate without the Ether Unit by Suppression of Elimination of Carbon Dioxide. Macromolecules 1997, 30, 737–744.
Delcroix, D.; Martín‐Vaca, B.; Bourissou, D.; Navarro, C. Ring‐Opening Polymerization of Trimethylene Carbonate Catalyzed by Methanesulfonic Acid: Activated Monomer versus Active Chain End Mechanisms. Macromolecules 2010, 43, 8828–8835.
Keul, H.; Bächer, R.; Höcker, H. Anionic ring‐opening polymerization of 2,2‐dimethyltrimethylene carbonate. Die Makromol. Chem. 1986, 187, 2579–2589.
Sanda, F.; Kamatani, J.; Endo, T. Synthesis and Anionic Ring‐Opening Polymerization Behavior of Amino Acid‐Derived Cyclic Carbonates. Macromolecules 2001, 34, 1564–1569.
Kühling, S.; Keul, H.; Höcker, H.; Buysch, H.‐J.; Schön, N. Synthesis of poly(2‐ethyl‐2‐hydroxymethyltrimethylene carbonate). Die Makromol. Chem. 1991, 192, 1193–1205.
Murayama, M.; Sanda, F.; Endo, T. Anionic Ring‐Opening Polymerization of a Cyclic Carbonate Having a Norbornene Structure with Amine Initiators. Macromolecules 1998, 31, 919–923.
Matsuo, J.; Sanda, F.; Endo, T. A novel observation in anionic ring‐opening polymerization behavior of cyclic carbonates having aromatic substituents. Macromol. Chem. Phys. 1998, 199, 2489–2494.
Matsuo, J.; Aoki, K.; Sanda, F.; Endo, T. Substituent Effect on the Anionic Equilibrium Polymerization of Six‐Membered Cyclic Carbonates. Macromolecules 1998, 31, 4432–4438.
Darensbourg, D.J.; Ganguly, P.; Billodeaux, D. Ring‐Opening Polymerization of Trimethylene Carbonate Using Aluminum(III) and Tin(IV) Salen Chloride Catalysts. Macromolecules 2005, 38, 5406–5410.
Darensbourg, D.J.; Choi, W.; Ganguly, P.; Richers, C.P. Biometal Derivatives as Catalysts for the Ring‐Opening Polymerization of Trimethylene Carbonate. Optimization of the Ca(II) Salen Catalyst System. Macromolecules 2006, 39, 4374–4379.
Darensbourg, D.J.; Choi, W.; Richers, C.P. Ring‐Opening Polymerization of Cyclic Monomers by Biocompatible Metal Complexes. Production of Poly(lactide), Polycarbonates, and Their Copolymers. Macromolecules 2007, 40, 3521–3523.
Darensbourg, D.J.; Choi, W.; Karroonnirun, O.; Bhuvanesh, N. Ring‐Opening Polymerization of Cyclic Monomers by Complexes Derived from Biocompatible Metals. Production of Poly(lactide), Poly(trimethylene carbonate), and Their Copolymers. Macromolecules 2008, 41, 3493–3502.
Kricheldorf, H.R.; Mahler, A. Polymers of carbonic acid 18: Polymerizations of cyclobis(hexamethylene carbonate) by means of BuSnCl3 or Sn(II)2‐ethylhexanoate. Polymer 1996, 37, 4383–4388.
Kricheldorf, H.R.; Stricker, A. Polymers of carbonic acid, 28. SnOct2‐initiated polymerizations of trimethylene carbonate (TMC, 1,3‐dioxanone‐2). Macromol. Chem. Phys. 2000, 201, 2557–2565.
Kricheldorf, H.R.; Weegen‐Schulz, B. Polymers of carbonic acid. XIV. High molecular weight poly(trimethylene carbonate) by ring‐opening polymerization with butyltin chlorides as initiators. J. Polym. Sci. Part A Polym. Chem. 1995, 33, 2193–2201.
Pêgo, A.P.; Grijpma, D.W.; Feijen, J. Enhanced mechanical properties of 1,3‐trimethylene carbonate polymers and networks. Polymer 2003, 44, 6495–6504.
Ling, J.; Shen, Z.; Huang, Q. Novel Single Rare Earth Aryloxide Initiators for Ring‐Opening Polymerization of 2,2‐ Dimethyltrimethylene Carbonate. Macromolecules 2001, 34, 7613–7616.
Naumann, S.; Thomas, A.W.; Dove, A.P. Highly Polarized Alkenes as Organocatalysts for the Polymerization of Lactones and Trimethylene Carbonate. ACS Macro Lett. 2016, 5, 134–138.
Gregory, G.L.; Jenisch, L.M.; Charles, B.; Kociok‐Köhn, G.; Buchard, A. Polymers from Sugars and CO2: Synthesis and Polymerization of a d‐Mannose‐Based Cyclic Carbonate. Macromolecules 2016, 49, 7165–7169.
Gregory, G.L.; Kociok‐Köhn, G.; Buchard, A. Polymers from sugars and CO2: Ring‐opening polymerisation and copolymerisation of cyclic carbonates derived from 2‐deoxy‐d‐ribose. Polym. Chem. 2017, 8, 2093–2104.
Gregory, G.L.; Hierons, E.M.; Kociok‐Köhn, G.; Sharma, R.I.; Buchard, A. CO2‐Driven stereochemical inversion of sugars to create thymidine‐based polycarbonates by ring‐opening polymerisation. Polym. Chem. 2017, 8, 1714–1721.
Gregory, G.L.; Lopez‐Vidal, E.M.; Buchard, A. Polymers from sugars: Cyclic monomer synthesis, ring‐opening polymerisation, material properties and applications. Chem. Commun. 2017, 53, 2198–2217.
Pati, D.; Feng, X.; Hadjichristidis, N.; Gnanou, Y. CO2 as versatile carbonation agent of glycosides: Synthesis of 5‐ and 6‐ membered cyclic glycocarbonates and investigation of their ring‐opening. J. CO2 Util. 2018, 24, 564–571.
Harris, R.F. Molecular weight advancement of poly(ethylene ether carbonate) polyols. J. Appl. Polym. Sci. 1989, 38, 463–476.
Pawłowski, P.; Rokicki, G. Synthesis of oligocarbonate diols from ethylene carbonate and aliphatic diols catalyzed by alkali metal salts. Polymer 2004, 45, 3125–3137.
Rokicki, G.; Kowalczyk, T. Synthesis of oligocarbonate diols and their characterization by MALDI‐TOF spectrometry. Polymer 2000, 41, 9013–9031.
Xu, J.; Feng, E.; Song, J. Renaissance of aliphatic polycarbonates: New techniques and biomedical applications. J. Appl. Polym. Sci. 2014, 131, 39822.
He, Q.; Zhang, Q.; Liao, S.; Zhao, C.; Xie, X. Understanding cyclic by‐products and ether linkage formation pathways in the transesterification synthesis of aliphatic polycarbonates. Eur. Polym. J. 2017, 97, 253–262.
Sun, J.; Kuckling, D. Synthesis of high‐molecular‐weight aliphatic polycarbonates by organo‐catalysis. Polym. Chem. 2016, 7, 1642–1649.
Meabe, L.; Lago, N.; Rubatat, L.; Li, C.; Müller, A.J.; Sardon, H.; Armand, M.; Mecerreyes, D. Polycondensation as a Versatile Synthetic Route to Aliphatic Polycarbonates for Solid Polymer Electrolytes. Electrochim. Acta 2017, 237, 259–266.
Naik, P.U.; Refes, K.; Sadaka, F.; Brachais, C.‐H.; Boni, G.; Couvercelle, J.‐P.; Picquet, M.; Plasseraud, L. Organo‐catalyzed synthesis of aliphatic polycarbonates in solvent‐free conditions. Polym. Chem. 2012, 3, 1475–1480.
Mutlu, H.; Ruiz, J.; Solleder, S.C.; Meier, M.a.R. TBD catalysis with dimethyl carbonate: A fruitful and sustainable alliance. Green Chem. 2012, 14, 1728–1735.
Park, J.H.; Jeon, J.Y.; Lee, J.J.; Jang, Y.; Varghese, J.K.; Lee, B.Y. Preparation of High‐Molecular‐Weight Aliphatic Polycarbonates by Condensation Polymerization of Diols and Dimethyl Carbonate. Macromolecules 2013, 46, 3301–3308.
Zhang, J.; Zhu, W.; Li, C.; Zhang, D.; Xiao, Y.; Guan, G.; Zheng, L. Effect of the biobased linear long‐chain monomer on crystallization and biodegradation behaviors of poly(butylene carbonate)‐based copolycarbonates. RSC Adv. 2015, 5, 2213–2222.
Zhu, W.; Huang, X.; Li, C.; Xiao, Y.; Zhang, D.; Guan, G. High‐molecular‐weight aliphatic polycarbonates by melt polycondensation of dimethyl carbonate and aliphatic diols: Synthesis and characterization. Polym. Int. 2011, 60, 1060–1067.
Zhu, W.; Zhou, W.; Li, C.; Xiao, Y.; Zhang, D.; Guan, G.; Wang, D. Synthesis, Characterization and Degradation of Novel Biodegradable Poly(butylene‐co‐hexamethylene carbonate) Copolycarbonates. J. Macromol. Sci. Part A 2011, 48, 583–594.
Sun, J.; Aly, K.I.; Kuckling, D. A novel one‐pot process for the preparation of linear and hyperbranched polycarbonates of various diols and triols using dimethyl carbonate. RSC Adv. 2017, 7, 12550–12560.
Wang, Z.; Yang, X.; Liu, S.; Hu, J.; Zhang, H.; Wang, G. One‐pot synthesis of high‐molecular‐weight aliphatic polycarbonates via melt transesterification of diphenyl carbonate and diols using Zn(OAc)2 as a catalyst. RSC Adv. 2015, 5, 87311–87319.
Wang, Z.; Yang, X.; Li, J.; Liu, S.; Wang, G. Synthesis of high‐molecular‐weight aliphatic polycarbonates from diphenyl carbonate and aliphatic diols by solid base. J. Mol. Catal. A Chem. 2016, 424, 77–84.
Vanderhenst, R.; Miller, S.A. Polycarbonates from biorenewable diols via carbonate metathesis polymerization. Green Mater. 2013, 1, 64–78.
Osamu Haban, I.I. Mitsuru Ueda, Shigeki Kuze, Synthesis of Polycarbonate from Dimethyl Carbonate and bisphenol‐A. J. Polym. Sci. 1998, 37, 2087–2093.
Ignatov, V.N.; Tartari, V.; Carraro, C.; Pippa, R.; Nadali, G.; Berti, C.; Fiorini, M. New Catalysts for Bisphenol A Polycarbonate Melt Polymerisation, 2. Polymer Synthesis and Characterisation. Macromol. Chem. Phys. 2001, 202, 1946–1949.
Kim, Y.; Choi, K.Y.; Chamberlin, T.A. Kinetics of melt transesterification of diphenyl carbonate and bisphenol A to polycarbonate with lithium hydroxide monohydrate catalyst. Ind. Eng. Chem. Res. 1992, 31, 2118–2127.
Fukuoka, S.; Kawamura, M.; Komiya, K.; Tojo, M.; Hachiya, H.; Hasegawa, K.; Aminaka, M.; Okamoto, H.; Fukawa, I.; Konno, S. A novel non‐phosgene polycarbonate production process using by‐product CO2 as starting material. Green Chem. 2003, 5, 497–507.
Zhang, M.; Lai, W.; Su, L.; Lin, Y.; Wu, G. A synthetic strategy toward isosorbide polycarbonate with a high molecular weight: The effect of intermolecular hydrogen bonding between isosorbide and metal chlorides. Polym. Chem. 2019, 10, 3380–3389.
Yang, Z.; Liu, L.; An, H.; Li, C.; Zhang, Z.; Fang, W.; Xu, F.; Zhang, S. Cost‐Effective Synthesis of High Molecular Weight Biobased Polycarbonate via Melt Polymerization of Isosorbide and Dimethyl Carbonate. ACS Sustain. Chem. Eng. 2020, 8, 9968– 9979.
Li, Q.; Zhu, W.; Li, C.; Guan, G.; Zhang, D.; Xiao, Y.; Zheng, L. A non‐phosgene process to homopolycarbonate and copolycarbonates of isosorbide using dimethyl carbonate: Synthesis, characterization, and properties. J. Polym. Sci. Part A: Polym. Chem. 2013, 51, 1387–1397.
Eo, Y.S.; Rhee, H.‐W.; Shin, S. Catalyst screening for the melt polymerization of isosorbide‐based polycarbonate. J. Ind. Eng. Chem. 2016, 37, 42–46.
Yang, Z.; Li, X.; Xu, F.; Wang, W.; Shi, Y.; Zhang, Z.; Fang, W.; Liu, L.; Zhang, S. Synthesis of bio‐based polycarbonate via one-step melt polycondensation of isosorbide and dimethyl carbonate by dual site‐functionalized ionic liquid catalysts. Green Chem. 2021, 23, 447–456.
Qian, W.; Ma, X.; Liu, L.; Deng, L.; Su, Q.; Bai, R.; Zhang, Z.; Gou, H.; Dong, L.; Cheng, W.; et al. Efficient synthesis of bio-derived polycarbonates from dimethyl carbonate and isosorbide: Regulating exo‐OH and endo‐OH reactivity by ionic liquids. Green Chem. 2020, 22, 5357–5368.
Li, C.; Zhang, Z.; Yang, Z.; Fang, W.; An, H.; Li, T.; Xu, F. Synthesis of bio‐based poly(oligoethylene glycols‐co‐isosorbide carbonate)s with high molecular weight and enhanced mechanical properties via ionic liquid catalyst. React. Funct. Polym. 2020, 155, 104689.
Qian, W.; Tan, X.; Su, Q.; Cheng, W.; Xu, F.; Dong, L.; Zhang, S. Transesterification of Isosorbide with Dimethyl Carbonate Catalyzed by Task‐Specific Ionic Liquids. ChemSuschem 2019, 12, 1169–1178.
Qian, W.; Liu, L.; Zhang, Z.; Su, Q.; Zhao, W.; Cheng, W.; Li, D.; Yang, Z.; Bai, R.; Xu, F.; et al. Synthesis of Bioderived Polycarbonates with Molecular Weight Adjustability Catalyzed by Phenolic‐derived Ionic Liquids. Green Chem. 2020, 22, 2488– 2497.
Sun, W.; Xu, F.; Cheng, W.; Sun, J.; Ning, G.; Zhang, S. Synthesis of isosorbide‐based polycarbonates via melt polycondensation catalyzed by quaternary ammonium ionic liquids. Chin. J. Catal. 2017, 38, 908–917.
Ma, C.; Xu, F.; Cheng, W.; Tan, X.; Su, Q.; Zhang, S. Tailoring Molecular Weight of Bioderived Polycarbonates via Bifunctional Ionic Liquids Catalysts under Metal‐Free Conditions. ACS Sustain. Chem. Eng. 2018, 6, 2684–2693.
Zhang, Z.; Xu, F.; He, H.; Ding, W.; Fang, W.; Sun, W.; Li, Z.; Zhang, S. Synthesis of high‐molecular weight isosorbide‐based polycarbonates through efficient activation of endo‐hydroxyl groups by an ionic liquid. Green Chem. 2019, 21, 3891–3901.
Fang, W.; Zhang, Z.; Yang, Z.; Zhang, Y.; Xu, F.; Li, C.; An, H.; Song, T.; Luo, Y.; Zhang, S. One‐pot synthesis of bio‐based polycarbonates from dimethyl carbonate and isosorbide under metal‐free condition. Green Chem. 2020, 22, 4550–4560.
Shen, X.; Liu, S.; Wang, Q.; Zhang, H.; Wang, G. Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by a KF/MgO Catalyst. Chem. Res. Chin. Univ. 2019, 35, 721–728.
Fenouillot, F.; Rousseau, A.; Colomines, G.; Saint‐Loup, R.; Pascault, J.P. Polymers from renewable 1,4:3,6‐dianhydrohexitols (isosorbide, isomannide and isoidide): A review. Prog. Polym. Sci. 2010, 35, 578–622.
Shen, X.‐L.; Wang, Z.‐Q.; Wang, Q.‐Y.; Liu, S.‐Y.; Wang, G.‐Y. Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by Ca/SBA‐15 Solid Base. Chin. J. Polym. Sci. 2018, 36, 1027–1035.
Zhang, M.; Lai, W.; Su, L.; Wu, G. Effect of Catalyst on the Molecular Structure and Thermal Properties of Isosorbide Polycarbonates. Ind. Eng. Chem. Res. 2018, 57, 4824–4831.
Ouhib, F.; Meabe, L.; Mahmoud, A.; Eshraghi, N.; Grignard, B.; Thomassin, J.‐M.; Aqil, A.; Boschini, F.; Jérôme, C.; Mecerreyes, D.; et al. CO2‐sourced polycarbonates as solid electrolytes for room temperature operating lithium batteries. J. Mater. Chem. A 2019, 7, 9844–9853.
Ngassam Tounzoua, C.; Grignard, B.; Brege, A.; Jerome, C.; Tassaing, T.; Mereau, R.; Detrembleur, C. A Catalytic Domino Approach toward Oxo‐Alkyl Carbonates and Polycarbonates from CO2, Propargylic Alcohols, and (Mono‐ and Di‐)Alcohols. ACS Sustain. Chem. Eng. 2020, 8, 9698–9710.
Siragusa, F.; Van Den Broeck, E.; Ocando, C.; Müller, A.J.; De Smet, G.; Maes, B.U.W.; De Winter, J.; Van Speybroeck, V.; Grignard, B.; Detrembleur, C. Access to Biorenewable and CO2‐Based Polycarbonates from Exovinylene Cyclic Carbonates. ACS Sustain. Chem. Eng. 2021, 9, 1714–1728.
