Browse > Article
http://dx.doi.org/10.7464/ksct.2011.17.3.201

Recent Development to Generate Carbon Dioxide-based Cyclic Carbonate and Polycarbonate  

Kwon, Doo-Yeon (Department of Molecular Science and Technology, Ajou University)
Kim, Jae-Il (Department of Molecular Science and Technology, Ajou University)
Kang, Hwi-Ju (Department of Molecular Science and Technology, Ajou University)
Kim, Da-Yeon (Department of Molecular Science and Technology, Ajou University)
Kim, Jae-Ho (Department of Molecular Science and Technology, Ajou University)
Lee, Bong (Department of Polymer Engineering, Pukyong National University)
Kim, Moon-Suk (Department of Molecular Science and Technology, Ajou University)
Publication Information
Clean Technology / v.17, no.3, 2011 , pp. 201-208 More about this Journal
Abstract
The green house gas, carbon dioxide, can be utilized as raw materials to prepare carbon dioxide-based polycarbonates in research and industry. The carbon dioxide-based polycarbonates is one of the emerging low-cost green polymers. Recently, the fast development of carbon dioxide-based polycarbonates has created new chances for industry. In this review, we describe the preparation and characterization of cyclic carbonate monomer using carbon dioxide, oxiranes and oxetanes in the presence of various catalysts and preparation of polycarbonates from cyclic carbonate monomer, presenting an organized and detailed overview of the state of the art.
Keywords
Carbon dioxide; Epoxide; Cyclic carbonate; Polycarbonate;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Schmitz, F., Keul, H., and Ho¨cker, H., "Alternating Copolymers of Tetramethylene Urea with 2,2-dimethyltrimethylene Carbonate and Ethylene Carbonate; Preparation of the Corresponding Polyurethanes," Macromol. Rapid Commun., 18(8), 699-706 (1997).   DOI   ScienceOn
2 Schmitz, F., Keul, H., and Ho¨cker, H., "Copolymerization of 2,2-dimethyltrimethylene Carbonate with Tetramethylene Urea: A New Route to the Polyurethane," Polymer, 39(14), 3179- 3186 (1998).   DOI   ScienceOn
3 Hyun, H., Cho, J. S., Kim, B. S., Lee, J. W., Kim, M. S., Khang, G., Park, K., and Lee, H. B., "Comparison of Micelles Formed by Amphiphilic Star Block Copolymers Prepared in the Presence of a Nonmetallic Monomer Activator," J. Polym. Sci., Part A: Polym. Chem., 46(6), 2084-2096 (2008).   DOI   ScienceOn
4 Kim, B. S., Oh, J. M., Cho, J. S., Lee, S. H., Lee, B., Khang, G., Lee, H. B., and Kim, M. S., "Comparison of Micelles Formed by Amphiphilic Poly(ethylene glycol)-b-Poly(trimethylene carbonate) Star Block Copolymers," J. Appl. Polym. Sci., 111(4), 1706-1712 (2009).   DOI   ScienceOn
5 Kim, B. H., Jang, S. H., Min S. R., and Kim, H. Y., "Propylene Carbonate Synthesis using Supercritical$ CO_2 $and Ionic Liquid," Clean Tech., 17(1), 37-40 (2011).
6 Shim, H. L., Lee, M. K., Yu, J. I., and Park, D. W., "Cycloaddition of Carbon Dioxide to Allyl Glycidyl Ether Using Silica-supported Ionic Liquid as a Catalyst," Clean Tech., 14(3), 166-170 (2008).
7 Decortes, A., Castilla, A. M., and Kleij, A. W., "Salen-Complex- Mediated Formation of Cyclic Carbonates by Cycloaddition of $CO_2$ to Epoxides," Angew. Chem. Int. Ed., 49(51), 9822-9837 (2010).   DOI   ScienceOn
8 Paddock, R. L., and Nguyen, S. T., "Chemical $CO_2$ Fixation: Cr(III) Salen Complexes as Highly Efficient Catalysts for the Coupling of $CO_2$ and Epoxides," J. Am. Chem. Soc., 123(46), 11498-11499 (2001).   DOI   ScienceOn
9 Dai, W. L., Luo, S. L., Yin, S. F., and Au, C. T., "The Direct Transformation of Carbon Dioxide to Organic Carbonates Over Heterogeneous Catalysts," Appl. Catal. A: General, 366(1), 2-12 (2009).   DOI   ScienceOn
10 Bhanage, B. M., Fujita, S. I., Ikushima, Y., and Arai, M., "Synthesis of Dimethyl Carbonate and Glycols from Carbon Dioxide, Epoxides, and Methanol using Heterogeneous Basic Metal Oxide Catalysts with High Activity and Selectivity," Appl. Catal. A: General, 219(1-2), 259-266 (2001).   DOI
11 Xiao, L. F., Li, F. W., Peng, J. J., and Xia, C. G., "Immobilized Ionic Liquid/zinc Chloride: Heterogeneous Catalyst for Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides," J. Mol. Catal. A: Chemical, 253(1-2), 265-269 (2006).   DOI   ScienceOn
12 Udayakumar, S., Raman, V., Shim, H. L., and Park, D. W., "Cycloaddition of Carbon Dioxide for Commercially-imperative Cyclic Carbonates using Ionic Liquid-functionalized Porous Amorphous Silica," Appl. Catal. A: General, 368(1-2), 97-104 (2009).   DOI   ScienceOn
13 Sun, J., Fujita, S. I., and Arai, M., "Development in the Green Synthesis of Cyclic Carbonate from Carbon Dioxide using Ionic Liquids," J. Organomet. Chem., 690(15), 3490-3497 (2005).   DOI   ScienceOn
14 Zhang, X., Wang, D., Zhao, M., Al-Arifi, A. S. N., Aouak, T., Al-Othman, Z. A., Wei, W., and Sun, Y., "Grafted Ionic Liquid: Catalyst for Solventless Cycloaddition of Carbon Dioxide and Propylene Oxide," Catal. Commun., 11(1), 43-46 (2009).   DOI   ScienceOn
15 Iwasaki, T., Kihara, N., and Endo, T., "Reaction of Various Oxiranes and Carbon Dioxide. Synthesis and Aminolysis of Five-membered Cyclic Carbonates," Bull. Chem. Soc. Jpn., 73(3), 713-719 (2000).   DOI   ScienceOn
16 Tomita, H., Sanda, F., and Endo, T., "Structural Analysis of Polyhydroxyurethane Obtained by Polyaddition of Bifunctional Five-Membered Cyclic Carbonate and Diamine Based on the Model Reaction," J. Polym. Sci. Part A: Polym. Chem., 39(6), 851-859 (2001).   DOI   ScienceOn
17 Baba, A., Kashiwagi, H., and Matsuda, H., "Cycloaddition of Oxetane and Carbon Dioxide Catalyzed by Tetraphenylstibonium Iodide," Tetrahedron Lett., 26(10), 1323-1324 (1985).   DOI   ScienceOn
18 Cardillo, G., Orena, M., Porzi, G., and Sandri, S., "A New Regio- and Stereo-selective Functionalization of Allylic and Homoallylic Alcohols," J. Chem. Soc., Chem. Commun., 10, 465-466 (1981).
19 Paek, S. M., Noh, S. K., Lyoo, W. S., and Shim, J. J., "Preparation of Poly(Vinyl Acetate) in the Presence of Supercritical Carbon Dioxide," Clean Technology, 12(4), 191-197 (2006).
20 Hwang, H. S., and Lim, K. T., "Ring-Opening Polymerization of L-Lactide with Polydimethylsiloxane Based Stabilizers in Supercritical Carbon Dioxide," Clean Technology, 12(2), 62-66 (2006).
21 Huang, S. Y., Liu, S. G., Li, J. P., Zhaog, N., Wei, W., and Sun, Y. H., "Synthesis of Cyclic Carbonate from Carbon Dioxide and Diols Over Metal Acetates," Fuel Chem. Technol., 35(6), 701-705 (2007).   DOI
22 Darensbourg, D. J., Lewis, S. J., Rodgers, J. L., and Yarbrough, J. C., "Carbon Dioxide/Epoxide Coupling Reactions Utilizing Lewis Base Adducts of Zinc Halides as Catalysts. Cyclic Carbonate Versus Polycarbonate Production," Inorg. Chem., 42(2), 581-589 (2003).   DOI   ScienceOn
23 Wua, S. S., Zhang, X. W., Dai, W. L., Yin, S. F., Li, W. S., Ren, Y. Q., and Au, C. T., "$ZnBr_2$-$Ph_4PI $ as Highly Efficient Catalyst for Cyclic Carbonates Synthesis from Terminal Epoxides and Carbon Dioxide," Appl. Catal. A: General, 341(1-2), 106-111 (2008).   DOI
24 Xiao, L. F., Li, F. W., and Xia, C. G., "An Easily Recoverable and Efficient Natural Biopolymer-supported Zinc Chloride Catalyst System for the Chemical Fixation of Carbon Dioxide to Cyclic Carbonate," Appl. Catal. A: General, 279(1-2), 125-129 (2005).   DOI
25 Calo, V., Nacci, A., Monopoli, A., and Fanizzi, A., "Cyclic Carbonate Formation from Carbon Dioxide and Oxiranes in Tetrabutylammonium Halides as Solvents and Catalysts," Org. Lett., 4(15), 2561-2563 (2002).   DOI   ScienceOn
26 Lu, X. B., Zhang, Y. J., Liang, B., Li, X., and Wang, H., "Chemical Fixation of Carbon Dioxide to Cyclic Carbonates under Extremely Mild Conditions with Highly Active Bifunctional Catalysts," J. Mol. Catal. A: Chemical, 210(1-2), 31-34 (2004).   DOI
27 Gao, J., Li, H., Zhang, Y., and Fei, W., "Non-phosgene Synthesis of Isocyanates Based on $CO_2$: Synthesis of Methyl N-phenyl Carbamate through Coupling Route with Lead Compound Catalysts," Catal. Today, 148(3-4), 378-382 (2009).   DOI
28 Fan, G., Wang, Z., Zou, B., and Wang, M., "Synthesis of Diphenyl Carbonate from Compressed Carbon Dioxide and Phenol without use of Organic Solvent," Fuel Process. Technol., 92(5), 1052-1055 (2011).   DOI   ScienceOn
29 Sakakura, T., and Kohno, K., "The Synthesis of Organic Carbonates from Carbon Dioxide," Chem. Commun., 11, 1312-1330 (2009).
30 Darensbourg, D. J., and Holtcamp, M. W., "Catalysts for the Reactions of Epoxides and Carbon Dioxide," Coord. Chem. Rev., 153, 155-174 (1996).   DOI
31 Webster, D. C., "Cyclic Carbonate Functional Polymers and their Applications," Prog. Org. Coat., 47(1), 77-86 (2003).   DOI   ScienceOn
32 Unger, F., Westedt, U., Hanefeld, P., Wombacher, R., Zimmermann, S., Greiner, A., Ausborn, M., and Kissel, T., "Poly (Ethylene Carbonate): A Thermoelastic and Biodegradable Biomaterial for Drug Eluting Stent Coatings?," J. Controlled Release, 117(3), 312-321 (2007).   DOI   ScienceOn
33 Hyun, H., Lee, J. W., Cho, J. S., Kim, Y. H., Lee, C. R., Kim, M. S., Khang, G., and Lee, H. B., "Polymeric Nano-micelles using Poly(Ethylene Glycol) and Poly(Trimethylene Carbonate) Diblock Copolymers as a Drug Carrier," Colloids Surf., A: Physicochem. Eng., 313-314, 131-135 (2008).   DOI
34 Acemoglu, M., Nimmerfall, F., Bantle, S., and Stoll, G. H., "Poly(Ethylene Carbonate)s, Part I: Syntheses and Structural Effects on Biodegradation," J. Controlled Release, 49(2-3), 263-276 (1997).   DOI
35 Lambert, O., Nagele, O., Loux, V., Bonny, J. D., and Laurent, M. H., "Poly(Ethylene Carbonate) Microspheres: Manufacturing Process and Internal Structure Characterization," J. Controlled Release, 67(1), 89-99 (2000).   DOI   ScienceOn
36 Inoue, S., Koinuma, H., and Tsuruta, T., "Recent Progress in the Synthesis of Polymers Based on Carbon Dioxide," J. Polym. Sci. Part B: Polym. Lett., 7, 287-292 (1969).   DOI
37 Ochiai, B., and Endo, T., "Carbon Dioxide and Carbon Disulfide as Resources for Functional Polymers," Prog. Polym. Sci., 30(2), 183-215 (2005).   DOI   ScienceOn
38 Sakakura, T., Choi, J. C., and Yasuda, H., "Transformation of Carbon Dioxide," Chem. Rev., 107, 2365-2387 (2007).   DOI   ScienceOn
39 Anastas, P. T., and Lankey, R. L., "Life Cycle Assessment and Green Chemistry: The Yin and Yang of Industrial Ecology," Green Chem., 2(6), 289-295 (2000).   DOI   ScienceOn
40 Anastas, P. T., and Kirchhoff, M. M., "Origins, Current Status, and Future Challenges of Green Chemistry," Acc. Chem. Res., 35(9), 686-694 (2002).   DOI   ScienceOn
41 Evans, W. J., and Katsumata, H., "Copolymerization of Ethylene Carbonate and $\varepsilon$-caprolactone using Samarium Complexes," Macromolecules, 27(14), 4011-4013 (1994).   DOI   ScienceOn
42 Ubaghs, L., Fricke, N., Keul, H., and Hocker, H., "Polyurethanes with Pendant Hydroxyl Groups: Synthesis and Characterization," Macromol. Rapid Commun., 25(3), 517-521 (2004).   DOI   ScienceOn
43 Pawlowski, P., and Rokicki, G., "Synthesis of Oligocarbonate Diols from Ethylene Carbonate and Aliphatic Diols Catalyzed by Alkali Metal Salts," Polymer, 45(10), 3125-3127 (2004).   DOI   ScienceOn
44 Tanzi, M. C., Fare, S., and Petrini, P., "In Vitro Stability of Polyether and Polycarbonate Urethanes," J. Biomater. Appl., 14(4), 325-348 (2000).   DOI   ScienceOn
45 Shirahama, H., Kanetani, A., and Yasuda, H., "Synthesis and Biodegradability of Copolymers of Ethylene Carbonate with Lactones," Polym. J., 32(3), 280-286 (2000).   DOI   ScienceOn