New insights into the cocatalyst-free carbonation of vegetable oil derivatives using heterogeneous catalysts

Kreye, 2013, Sustainable routes to polyurethane precursors, Green Chem., 15, 1431, 10.1039/c3gc40440d Pérez-Sena, 2018, Aminolysis of cyclic-carbonate vegetable oils as a non-isocyanate route for the synthesis of polyurethane: a kinetic and thermal study, Chem. Eng. J., 346, 271, 10.1016/j.cej.2018.04.028 Guzmán Agudelo, 2020, Influence of steric effects on the kinetics of cyclic-carbonate vegetable oils aminolysis, Chem. Eng. Sci., 228, 115954, 10.1016/j.ces.2020.115954 Petrović, 2008, Polyurethanes from vegetable oils, Polym. Rev., 48, 109, 10.1080/15583720701834224 Webster, 2003, Cyclic carbonate functional polymers and their applications, Prog. Org. Coat., 47, 77, 10.1016/S0300-9440(03)00074-2 Saptal, 2017, Current advances in heterogeneous catalysts for the synthesis of cyclic carbonates from carbon dioxide, Curr. Opin. Green Sustain. Chem., 3, 1 Kim, 2013, CO2 cycloaddition of styrene oxide over MOF catalysts, Appl. Catal. Gen., 453, 175, 10.1016/j.apcata.2012.12.018 Liang, 2018, An efficient heterogeneous LiBr/γ-Al 2 O 3 catalyst for the cycloaddition of CO 2 with diglycidyl ethers: An efficient heterogeneous LiBr/γ-Al 2 O 3 catalyst for the cycloaddition of CO 2with diglycidyl ethers, J. Chem. Technol. Biotechnol., 93, 2271, 10.1002/jctb.5570 Kohrt, 2015, Recyclable bifunctional polystyrene and silica gel-supported organocatalyst for the coupling of CO 2 with epoxides, ChemSusChem, 8, 2031, 10.1002/cssc.201500128 Lu, 2012, Cobalt catalysts for the coupling of CO2 and epoxides to provide polycarbonates and cyclic carbonates, Chem. Soc. Rev., 41, 1462, 10.1039/C1CS15142H Alves, 2015, Organocatalytic synthesis of bio-based cyclic carbonates from CO 2 and vegetable oils, RSC Adv., 5, 53629, 10.1039/C5RA10190E Su, 2014, Urea-derived graphitic carbon nitride as an efficient heterogeneous catalyst for CO2 conversion into cyclic carbonates, Catal. Sci. Technol., 4, 1556, 10.1039/c3cy00921a Zhao, 2019, Synthesis of propylene carbonate from carbon dioxide through high activity of magnesium oxide, J. Chem. Eng. Jpn., 52, 406, 10.1252/jcej.18we073 Ahmed, 2014, Macroporous metal–organic framework microparticles with improved liquid phase separation, J. Mater. Chem. A, 2, 9085, 10.1039/C4TA00138A Yan, 2012, 6 Hu, 2020, Hierarchical Co/ZIF-8 as an efficient catalyst for cycloaddition of CO2 and epoxide, Microporous Mesoporous Mater., 294, 109917, 10.1016/j.micromeso.2019.109917 Hu, 2020, Bifunctional metal-doped ZIF-8: a highly efficient catalyst for the synthesis of cyclic carbonates from CO2 cycloaddition, Microporous Mesoporous Mater., 299, 110123, 10.1016/j.micromeso.2020.110123 Zhang, 2016, Graphene oxide grafted hydroxyl-functionalized ionic liquid: a highly efficient catalyst for cycloaddition of CO2 with epoxides, Appl. Catal. Gen., 509, 111, 10.1016/j.apcata.2015.10.038 Sankar, 2015, Supported imidazole as heterogeneous catalyst for the synthesis of cyclic carbonates from epoxides and CO2, Catal. Commun., 59, 201, 10.1016/j.catcom.2014.10.026 Liu, 2016, Design of bifunctional NH3I-Zn/SBA-15 single-component heterogeneous catalyst for chemical fixation of carbon dioxide to cyclic carbonates, J. Mol. Catal. Chem., 418–419, 78, 10.1016/j.molcata.2016.03.037 Honda, 2014, Direct cyclic carbonate synthesis from CO2 and diol over carboxylation/hydration cascade catalyst of CeO2 with 2-cyanopyridine, ACS Catal., 4, 1893, 10.1021/cs500301d Sakakura, 2007, Transformation of carbon dioxide, Chem. Rev., 107, 2365, 10.1021/cr068357u Aresta, 2007, Utilisation of CO2 as a chemical feedstock: opportunities and challenges, Dalton Trans., 2975, 10.1039/b700658f Luo, 2014, 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, 10.1039/C4GC00671B Longwitz, 2018, Calcium-based catalytic system for the synthesis of bio-derived cyclic carbonates under mild conditions, ACS Catal., 8, 665, 10.1021/acscatal.7b03367 Comerford, 2015, Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings, Green Chem., 17, 1966, 10.1039/C4GC01719F Huang, 2016, Cycloaddition of CO 2 and epoxide catalyzed by amino- and hydroxyl-rich graphitic carbon nitride, Catal. Sci. Technol., 6, 2942, 10.1039/C5CY01805F Calabrese, 2019, Hybrid catalysts for CO2 conversion into cyclic carbonates, Catalysts, 9, 325, 10.3390/catal9040325 North, 2010, Synthesis of cyclic carbonates from epoxides and CO2, Green Chem., 12, 1514, 10.1039/c0gc00065e Monfared, 2019, Cycloaddition of atmospheric CO 2 to epoxides under solvent-free conditions: a straightforward route to carbonates by green chemistry metrics, RSC Adv., 9, 3884, 10.1039/C8RA10233C Decortes, 2010, Efficient carbonate synthesis under mild conditions through cycloaddition of carbon dioxide to oxiranes using a Zn(salphen) catalyst, Chem. Commun., 46, 4580, 10.1039/c000493f Du, 2005, Sn-catalyzed synthesis of propylene carbonate from propylene glycol and CO2 under supercritical conditions, J. Mol. Catal. Chem., 241, 233, 10.1016/j.molcata.2005.07.030 Castro-Osma, 2015, New catalysts for carboxylation of propylene glycol to propylene carbonate via high-throughput screening, Faraday Discuss., 183, 19, 10.1039/C5FD00061K Bähr, 2012, Linseed and soybean oil-based polyurethanes prepared via the non-isocyanate route and catalytic carbon dioxide conversion, Green Chem., 14, 483, 10.1039/c2gc16230j Ruiz, 2017, Upgrading castor oil: from heptanal to non-isocyanate poly(amide-hydroxyurethane)s, Polymer, 124, 226, 10.1016/j.polymer.2017.07.070 Miloslavskiy, 2014, Cyclic carbonates based on vegetable oils, Int. Lett. Chem. Phys. Astron., 27, 20, 10.18052/www.scipress.com/ILCPA.27.20 Peña Carrodeguas, 2017, Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions, Green Chem., 19, 3535, 10.1039/C7GC01206C Cai, 2017, Influence of gas-liquid mass transfer on kinetic modeling: carbonation of epoxidized vegetable oils, Chem. Eng. J., 313, 1168, 10.1016/j.cej.2016.11.012 Cai, 2019, Structure–reactivity: comparison between the carbonation of epoxidized vegetable oils and the corresponding epoxidized fatty acid methyl ester, Ind. Eng. Chem. Res., 58, 1548, 10.1021/acs.iecr.8b05510 Schäffner, 2014, Synthesis and application of carbonated fatty acid esters from carbon dioxide including a life cycle analysis, ChemSusChem, 7, 1133, 10.1002/cssc.201301115 Parzuchowski, 2006, Epoxy resin modified with soybean oil containing cyclic carbonate groups, J. Appl. Polym. Sci., 102, 2904, 10.1002/app.24795 Büttner, 2017, Organocatalyzed synthesis of oleochemical carbonates from CO 2 and renewables, ChemSusChem, 10, 1076, 10.1002/cssc.201601163 Motokura, 2009, Silica-supported aminopyridinium halides for catalytic transformations of epoxides to cyclic carbonates under atmospheric pressure of carbon dioxide, Green Chem., 11, 1876, 10.1039/b916764c Jay, 1964, Direct titration of epoxy compounds and aziridines, Anal. Chem., 36, 667, 10.1021/ac60209a037 Maria Chong, 2003, Functionalization of SBA-15 with APTES and characterization of functionalized materials, J. Phys. Chem. B, 107, 12650, 10.1021/jp035877+ Swern, 1947, Determination of oxirane oxygen, Anal. Chem., 19, 414, 10.1021/ac60006a018 Sun, 2009, Water as an efficient medium for the synthesis of cyclic carbonate, Tetrahedron Lett., 50, 423, 10.1016/j.tetlet.2008.11.034 Zhou, 2010, Hydrated alkali metal halides as efficient catalysts for the synthesis of cyclic carbonates from CO2 and epoxides, Chin. J. Catal., 31, 765, 10.1016/S1872-2067(09)60086-3 Wong, 2008, A robust ionic liquid as reaction medium and efficient organocatalyst for carbon dioxide fixation, ChemSusChem, 1, 67, 10.1002/cssc.200700097 Wang, 2012, Experimental and theoretical studies on hydrogen bond-promoted fixation of carbon dioxide and epoxides in cyclic carbonates, Phys. Chem. Chem. Phys., 14, 11021, 10.1039/c2cp41698k Liu, 2015, Insights into hydrogen bond donor promoted fixation of carbon dioxide with epoxides catalyzed by ionic liquids, Phys. Chem. Chem. Phys., 17, 5959, 10.1039/C4CP05464D Tharun, 2012, 8 Ramin, 2005, Behavior of homogeneous and immobilized zinc-based catalysts in cycloaddition of CO2 to propylene oxide, J. Catal., 234, 256, 10.1016/j.jcat.2005.06.020 Mazo, 2013, Carbonation of epoxidized soybean oil improved by the addition of water, J. Am. Oil Chem. Soc., 90, 725, 10.1007/s11746-013-2214-3