Korean Chemical Engineering Research

  • 제51권3호
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  • Pages.342-346
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  • 2013
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  • 0304-128X(pISSN)
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  • 2233-9558(eISSN)
한국화학공학회 (The Korean Institute of Chemical Engineers)
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이온성 액체를 이용한 CO2와 glycidyl methacrylate의 고리화 첨가 및 고분자 가교 반응

Cycloaddition and Crosslinking Reactions of CO2 and Glycidyl Methacrylate using Ionic Liquid

  • Kim, Dong Hyun (Department of Chemical Engineering, Kongju National University) ;
  • Kang, Tae Won (Department of Chemical Engineering, Kongju National University) ;
  • Lee, Jong Jib (Department of Chemical Engineering, Kongju National University) ;
  • Ko, Young Soo (Department of Chemical Engineering, Kongju National University)
  • 투고 : 2013.03.20
  • 심사 : 2013.04.15
  • 발행 : 2013.06.01
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초록

온실가스인 $CO_2$를 저감하기 위한 기술로 본 연구에서는 이온성 액체를 이용하여 epoxide계 화합물인 glycidyl methacrylate (GMA)와 $CO_2$의 고리화 첨가 반응(cycloaddition)을 통해 cyclic carbonate를 합성하였다. 합성된 cyclic carbonate인 [2-oxo-1,3-dioxolan-4-yl]methacrylate (DOMA)는 FT-IR과 $^1H$ NMR을 이용하여 그 구조를 확인하였다. 또한 $^1H$ NMR을 통하여 계산된 조성비를 이용하여 전환율과 시간의 관계를 관찰하였다. DOMA로 전환이 모두 이루어진 이후에는 DOMA의 이중결합이 잔존하는 이온성 액체로 음이온 중합, cyclic carbonate ring의 가교반응에 의한 고분자가 형성되었다.

In this study the cycloaddition of glycidyl methacrylate (GMA) and $CO_2$ using ionic liquid as catalyst was performed for the technology of $CO_2$ reduction. The structure of synthesized cyclic carbonate, [2-oxo-1,3-dioxolan-4-yl]methacrylate (DOMA) was analyzed and confirmed by FT-IR and $^1H$-NMR. The change in conversion with respect to reaction time was investigated using $^1H$-NMR. Interestingly, the ionic polymerization of vinyl groups and crosslinking reaction between cyclic carbonate rings of DOMA were observed following completion of cycloaddition.

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참고문헌

  1. Wang, H. Y. and Au, C. T., "Carbon Dioxide Reforming of Methane to Syngas Over $SiO_{2}$-supported Rhodium Catalysts," Appl. Catal. A: Gen., 155, 239-252(1997). https://doi.org/10.1016/S0926-860X(96)00398-5
  2. Ma, Y., Sun, Q., Wu, D., Fan, W. H., Zhang, Y. L. and Deng, J. F., "A Practical Approach for the Preparation of High Activity Cu/ZnO/$ZrO_{2}$ Catalyst for Methanol Synthesis from $CO_{2}$ Hydrogenation," Appl. Catal. A: Gen., 171, 45-55(1998). https://doi.org/10.1016/S0926-860X(98)00079-9
  3. Song, K. H., Ryu, J. H. and Chung, J. S., "Recent Research Trends of Catalytic Conversion of $CO_{2}$ to High-value Chemicals", Korean Chem. Eng. Res.(HWAHAK KONGHAK), 47, 519-530(2009).
  4. Kim, I., Park, D. W. and Ha, C. S., "Production of Environmentally Friendly and Biodegradable Polycarbonates by Alternating Copolymerization of Epoxides with Carbon Dioxide," J. Korea Ind. Eng. Chem., 13, 632-640(2002).
  5. 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, 3490-3497(2005). https://doi.org/10.1016/j.jorganchem.2005.02.011
  6. Oh, H. J. and Ko, Y. S., "Effect of Polymerization Conditions on the Polymer Properties of $CO_{2}$-cyclohexene Oxide Copolymer Prepared by Double Metal Cyanide Catalyst," J. Ind. Eng. Chem., http://dx.doi.org/10.1016/j.jiec.2013.03.002(2013).
  7. Lee, W. K., Park, D. M., Park, J. W. and Jung, C. S., "Reduction Potential of Additives under the Linear Carbonate Electrolyte," Journal of the Institute of Industrial Technology, 14, 77-80(2006).
  8. Lee, E. H., Cha, S. W. and Dharma, M. M., Choe, Y. S., Ahn, J. Y. and Park, D. W., "Cycloaddition of Carbon Dioxide to Epichlorohydrin Using Ionic Liquid as a Catalyst," Korean J. Chem. Eng., 24, 547-550(2007). https://doi.org/10.1007/s11814-007-0097-4
  9. Shaikh, A.-A. G. and Sivaram, S., "Organic Carbonates," Chem. Rev., 96, 951-976(1996). https://doi.org/10.1021/cr950067i
  10. Son, Y. S., Park, M. K., Kim, G. W. and Park, S. W., "Reaction Kinetics of Carbon Dioxide and Glycidyl Methacrylate using a Ionic Liquid Catalyst of Imidazole Immobilized on MCM41," Korean Chem. Eng. Res., 47, 410-417(2009).
  11. Coates, G. W. and Moore, D. R., "Discrete Metal-Based Catalysts for the Copolymerization of $CO_{2}$ and Epoxide: Discovery, Reactivity, Optimization, and Mechanism", Angew. Chem. Int. Ed., 43, 6618-6639(2004). https://doi.org/10.1002/anie.200460442
  12. Odian, G., Principles of polymerization, 4nd ed., John Wiley, New Jersey(2004).
  13. Yang, J. G., Moon, J. Y., Jung, S. M., Park, D. W. and Lee, J. K., "Addition Reaction of Glycidyl Methacrylate with Carbon Dioxide Using Quaternary Ammonium Salts as Catalyst," J. Korean Ind. Eng. Chem., 7, 1156-1163(1996).
  14. Kim, J. J., Shin, D. H. and Park, D. W., "Synthesis of (2-oxo-1,3-dioxolan-4-yl)methacrylate Using Soluble Polymer-Supported Quaternary Ammonium Salt Catalysts," Appl. Chem., 5, 1-4(2001).
  15. Sanda, F., Kamatani, J. and Endo, T., "Synthesis and Anionic Ring-Opening Polymerization Behavior of Amino Acid-Derived Cyclic Carbonates," Macromolecules, 34, 1564-1569(2001). https://doi.org/10.1021/ma0013307