[en] The study deals with the catalytic cyclocarbonation of epoxides to produce monomers used in the synthesis of polyurethane. A benchmark study of the textural properties of silica-based, doped or not, supports enabling the identification and optimization of the key parameters affecting the catalytic activity is reported. The results reveal that ammonium catalysts immobilized onto mesostructured supports with high surface area and low aggregation show better catalytic performances than analogue catalysts grafted onto microstuctured ones. While a high external surface area favours the grafting of ammonium salt, pore size must be large enough to enhance the accessibility of both carbon dioxide and epoxides to the catalytic sites. The activity of heterogeneous cat- alysts was evaluated for a model coupling reaction between carbon dioxide and propylene glycol diglycidylether. Using appropriated supports, cyclocarbonation yields are found to be higher in the presence of the hetero- geneous catalyst in comparison with the homogeneous one. These results allow to confirm the beneficial effect of the presence of residual OH silanol groups at the surface of the support, which activate epoxide through forming of hydrogen bonds.
Research Center/Unit :
Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit Center for Education and Research on Macromolecules (CERM) Nanomaterials, Catalysis, Electrochemistry
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Léonard, Géraldine L.-M.; University of Liège (ULiège), Department of Chemical Engineering – Nanomaterials, Catalysis, Electrochemistry
Pirard, Sophie ; University of Liège (ULiège), Department of Chemical Engineering – Nanomaterials, Catalysis, Electrochemistry
Belet, Artium ; University of Liège (ULiège), Department of Chemical Engineering – Nanomaterials, Catalysis, Electrochemistry
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
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
Heinrichs, Benoît ; University of Liège (ULiège), Department of Chemical Engineering – Nanomaterials, Catalysis, Electrochemistry
Language :
English
Title :
Optimizing support properties of heterogeneous catalysts for the coupling of carbon dioxide with epoxides
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Bibliography
Martín, C., Fiorani, G., Kleij, A.W., Recent advances in the catalytic preparation of cyclic organic carbonates. ACS Catal. 5 (2015), 1353–1370.
Aresta, M., Dibenedetto, A., Angelini, A., Catalysis for the valorization of exhaust carbon: from CO2 to chemicals, materials, and fuels. Technological use of CO2. Chem. Rev. 114 (2014), 1709–1742.
Shim, H.-L., Udayakumar, S., Yu, J.-I., Kim, I., Park, D.-W., Synthesis of cyclic carbonate from allyl glycidyl ether and carbon dioxide using ionic liquid-functionalized amorphous silica. Catal. Today 148 (2009), 350–354.
Schäffner, B., Schäffner, F., Verevkin, S.P., Börner, A., Organic carbonates as solvents in synthesis and catalysis. Chem. Rev. 110 (2010), 4554–4581.
Poussard, L., Mariage, J., Grignard, B., Detrembleur, C., Jérôme, C., Calberg, C., Heinrichs, B., De Winter, J., Gerbaux, P., Raquez, J.M., Bonnaud, L., Dubois, P., Non-isocyanate polyurethanes from carbonated soybean oil using monomeric or oligomeric diamines to achieve thermosets or thermoplastics. Macromolecules 49 (2016), 2162–2171.
Grignard, B., Thomassin, J.M., Gennen, S., Poussard, L., Bonnaud, L., Raquez, J.M., Dubois, P., Tran, M.P., Park, C.B., Jerome, C., Detrembleur, C., CO2-blown microcellular non-isocyanate polyurethane (NIPU) foams: from bio- and CO2-sourced monomers to potentially thermal insulating materials. Green Chem. 18 (2016), 2206–2215.
Maisonneuve, L., Lamarzelle, O., Rix, E., Grau, E., Cramail, H., Isocyanate-free routes to polyurethanes and poly(hydroxy urethane)s. Chem. Rev. 115 (2015), 12407–12439.
Karol, M.H., Kramarik, J.A., Phenyl isocyanate is a potent chemical sensitizer. Toxicol. Lett. 89 (1996), 139–146.
Besse, V., Auvergne, R., Carlotti, S., Boutevin, G., Otazaghine, B., Caillol, S., Pascault, J.-P., Boutevin, B., Synthesis of isosorbide based polyurethanes: An isocyanate free method. React. Funct. Polym. 73 (2013), 588–594.
Udayakumar, S., Raman, V., Shim, H.-L., Park, D.-W., Cycloaddition of carbon dioxide for commercially-imperative cyclic carbonates using ionic liquid-functionalized porous amorphous silica. Appl. Catal. A 368 (2009), 97–104.
Alves, M., Grignard, B., Gennen, S., Detrembleur, C., Jerome, C., Tassaing, T., Organocatalytic synthesis of bio-based cyclic carbonates from CO2 and vegetable oils. RSC Adv. 5 (2015), 53629–53636.
Bahr, M., Mulhaupt, R., Linseed and soybean oil-based polyurethanes prepared via the nonisocyanate route and catalytic carbon dioxide conversion. Green Chem. 14 (2012), 483–489.
Fiorani, G., Guo, W., Kleij, A.W., Sustainable conversion of carbon dioxide: the advent of organocatalysis. Green Chem. 17 (2015), 1375–1389.
Comerford, J.W., Ingram, I.D.V., North, M., Wu, X., Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings. Green Chem. 17 (2015), 1966–1987.
Han, L., Choi, H.-J., Choi, S.-J., Liu, B., Park, D.-W., Ionic liquids containing carboxyl acid moieties grafted onto silica: synthesis and application as heterogeneous catalysts for cycloaddition reactions of epoxide and carbon dioxide. Green Chem. 13 (2011), 1023–1028.
Adam, F., Batagarawa, M.S., Tetramethylguanidine–silica nanoparticles as an efficient and reusable catalyst for the synthesis of cyclic propylene carbonate from carbon dioxide and propylene oxide. Appl. Catal. A 454 (2013), 164–171.
Jose, T., Hwang, Y., Kim, D.-W., Kim, M.-I., Park, D.-W., Functionalized zeolitic imidazolate framework F-ZIF-90 as efficient catalyst for the cycloaddition of carbon dioxide to allyl glycidyl ether. Catal. Today 245 (2015), 61–67.
Appaturi, J.N., Adam, F., A facile and efficient synthesis of styrene carbonate via cycloaddition of CO2 to styrene oxide over ordered mesoporous MCM-41-Imi/Br catalyst. Appl. Catal. B 136–137 (2013), 150–159.
Wang, T.-T., Xie, Y., Deng, W.-Q., Reaction mechanism of epoxide cycloaddition to CO2 catalyzed by salen-M (M = Co, Al, Zn). J. Phys. Chem. A 118 (2014), 9239–9243.
Sun, J., Fujita, S.-I., Zhao, F., Hasegawa, M., Arai, M., A direct synthesis of styrene carbonate from styrene with the Au/SiO2–ZnBr 2/Bu4NBr catalyst system. J. Catal. 230 (2005), 398–405.
Aoyagi, N., Furusho, Y., Endo, T., Convenient synthesis of cyclic carbonates from CO2 and epoxides by simple secondary and primary ammonium iodides as metal-free catalysts under mild conditions and its application to synthesis of polymer bearing cyclic carbonate moiety. J. Polym. Sci., Part A: Polym. Chem. 51 (2013), 1230–1242.
Chopade, P.R., Louie, J., [2+2+2] Cycloaddition reactions catalyzed by transition metal complexes. Adv. Synth. Catal. 348 (2006), 2307–2327.
Pescarmona, P.P., Taherimehr, M., Challenges in the catalytic synthesis of cyclic and polymeric carbonates from epoxides and CO2. Catal. Sci. Technol. 2 (2012), 2169–2187.
Łukaszczyk, J., Jaszcz, K., Kuran, W., Listos, T., Synthesis of functional polycarbonates by copolymerization of carbon dioxide with allyl glycidyl ether. Macromol. Rapid Commun. 21 (2000), 754–757.
Darensbourg, D.J., Chung, W.-C., Availability of other aliphatic polycarbonates derived from geometric isomers of butene oxide and carbon dioxide coupling reactions. Macromolecules 47 (2014), 4943–4948.
Kumar, S., Jain, S.L., Sain, B., Metal acetylacetonates as highly efficient and cost effective catalysts for the synthesis of cyclic carbonates from CO2 and epoxides. Catal. Lett. 142 (2012), 615–618.
Alves, M., Grignard, B., Gennen, S., Mereau, R., Detrembleur, C., Jerome, C., Tassaing, T., Organocatalytic promoted coupling of carbon dioxide with epoxides: a rational investigation of the cocatalytic activity of various hydrogen bond donors. Catal. Sci. Technol. 5 (2015), 4636–4643.
Wang, J., Zhang, Y., Boronic acids as hydrogen bond donor catalysts for efficient conversion of CO2 into organic carbonate in water. ACS Catal. 6 (2016), 4871–4876.
Udayakumar, S., Park, S.-W., Park, D.-W., Choi, B.-S., Immobilization of ionic liquid on hybrid MCM-41 system for the chemical fixation of carbon dioxide on cyclic carbonate. Catal. Commun. 9 (2008), 1563–1570.
Xiong, Y., Wang, Y., Wang, H., Wang, R., Cui, Z., Novel one-step synthesis to cross-linked polymeric nanoparticles as highly active and selective catalysts for cycloaddition of CO2 to epoxides. J. Appl. Polym. Sci. 123 (2012), 1486–1493.
Han, L., Choi, H.-J., Kim, D.-K., Park, S.-W., Liu, B., Park, D.-W., Porous polymer bead-supported ionic liquids for the synthesis of cyclic carbonate from CO2 and epoxide. J. Mol. Catal. A: Chem. 338 (2011), 58–64.
Lambert, S., Cellier, C., Gaigneaux, E.M., Pirard, J.-P., Heinrichs, B., Ag/SiO2, Cu/SiO2 and Pd/SiO2 cogelled xerogel catalysts for benzene combustion: Relationships between operating synthesis variables and catalytic activity. Catal. Commun. 8 (2007), 1244–1248.
Lambert, S., Cellier, C., Grange, P., Pirard, J.-P., Heinrichs, B.t., Synthesis of Pd/SiO2, Ag/SiO2, and Cu/SiO2 cogelled xerogel catalysts: study of metal dispersion and catalytic activity. J. Catal. 221 (2004), 335–346.
Heinrichs, B., Geus, J.W., Lambert, S., Pirard, J.-P., A TEM study on the localization of metal particles in cogelled xerogel catalysts. J. Catal. 241 (2006), 229–231.
Léonard, A., Blin, J.L., Jacobs, P.A., Grange, P., Su, B.L., Chemistry of silica at different concentrations of non-ionic surfactant solutions: effect of pH of the synthesis gel on the preparation of mesoporous silicas. Microporous Mesoporous Mater. 63 (2003), 59–73.
Léonard, A., Blin, J.L., Robert, M., Jacobs, P.A., Cheetham, A.K., Su, B.L., Toward a better control of internal structure and external morphology of mesoporous silicas synthesized using a nonionic surfactant. Langmuir 19 (2003), 5484–5490.
Léonard, A., Blin, J.L., Su, B.L., Pore structure evolution of highly ordered mesoporous silica CMI-1 during boiling water treatment: a multi-technique investigation. Colloids Surf., A 241 (2004), 87–93.
Chapter 3 The surface chemistry of silica, Studies in Surface Science and Catalysis, 93 (1995) 59–77.
Lowell, S., Shields, J.E., Thomas, M.A., Thommes, M., Surface Area Analysis from the Langmuir and BET Theories, Characterization of Porous Solids and Powders: Surface Area, Pore Size and Density. 2004, Springer, Netherlands, Dordrecht, 58–81.
Lowell, S., Shields, J.E., Thomas, M.A., Thommes, M., Micropore Analysis, Characterization of Porous Solids and Powders: Surface Area, Pore Size and Density. 2004, Springer, Netherlands, Dordrecht, 129–156.
Lowell, S., Shields, J.E., Thomas, M.A., Thommes, M., Mesopore Analysis, Characterization of Porous Solids and Powders: Surface Area, Pore Size and Density. 2004, Springer, Netherlands, Dordrecht, 101–128.
Lowell, S., Shields, J.E., Thomas, M.A., Thommes, M., Other Surface Area Methods, Characterization of Porous Solids and Powders: Surface Area, Pore Size and Density. 2004, Springer, Netherlands, Dordrecht, 82–93.
Giesche, H., Mercury porosimetry: a general (practical) overview. Part. Part. Syst. Char. 23 (2006), 9–19.
Pirard, R., Heinrichs, B., Van Cantfort, O., Pirard, J.P., Mercury porosimetry applied to low density xerogels; relation between structure and mechanical properties. J. Sol-Gel Sci. Technol. 13 (1998), 335–339.
Mueller, R., Kammler, H.K., Wegner, K., Pratsinis, S.E., OH surface density of SiO2 and TiO2 by thermogravimetric analysis. Langmuir 19 (2003), 160–165.
Udayakumar, S., Lee, M.-K., Shim, H.-L., Park, S.-W., Park, D.-W., Imidazolium derivatives functionalized MCM-41 for catalytic conversion of carbon dioxide to cyclic carbonate. Catal. Commun. 10 (2009), 659–664.
Wang, J.-Q., Yue, X.-D., Cai, F., He, L.-N., Solventless synthesis of cyclic carbonates from carbon dioxide and epoxides catalyzed by silica-supported ionic liquids under supercritical conditions. Catal. Commun. 8 (2007), 167–172.
Wang, J.-Q., Kong, D.-L., Chen, J.-Y., Cai, F., He, L.-N., Synthesis of cyclic carbonates from epoxides and carbon dioxide over silica-supported quaternary ammonium salts under supercritical conditions. J. Mol. Catal. A: Chem. 249 (2006), 143–148.
Jagtap, S.R., Raje, V.P., Samant, S.D., Bhanage, B.M., Silica supported polyvinyl pyridine as a highly active heterogeneous base catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides. J. Mol. Catal. A: Chem. 266 (2007), 69–74.
Barbarini, A., Maggi, R., Mazzacani, A., Mori, G., Sartori, G., Sartorio, R., Cycloaddition of CO2 to epoxides over both homogeneous and silica-supported guanidine catalysts. Tetrahedron Lett. 44 (2003), 2931–2934.
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