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Application of Silica-supported Ionic Liquid Catalysts to Cycloaddition of CO2

CO2 부가반응에 적용된 Silica 담지 이온성 액체 촉매

  • Kim, Dong-Woo (Chemical Industry Development Center, Korea Research Institute of Chemical Technology) ;
  • Kim, Hyeon-Gook (Chemical Industry Development Center, Korea Research Institute of Chemical Technology) ;
  • Cho, Deug-Hee (Chemical Industry Development Center, Korea Research Institute of Chemical Technology)
  • 김동우 (화학산업고도화센터, 한국화학연구원) ;
  • 김현국 (화학산업고도화센터, 한국화학연구원) ;
  • 조득희 (화학산업고도화센터, 한국화학연구원)
  • Received : 2016.04.05
  • Accepted : 2016.05.10
  • Published : 2016.06.10

Abstract

The catalytic applicability of various ionic liquids immobilized on different silica-supports such as amorphous, SBA, MCM and commercial silica for the cycloaddition of $CO_2$ and epoxides is reviewed in this work. The effects of different structures of supported ionic liquids and silica supports in the synthesis cyclic carbonate by the cycloaddition of $CO_2$ have been remarked. The studies revealed that ionic liquids possessing functional groups or metals exhibited increased catalytic performance towards cyclic carbonate synthesis. Moreover, the reusability of SSIL catalyst and mechanism for the cycloaddition of $CO_2$ were studied.

본 총설에서는 $CO_2$와 에폭시 화합물의 부가반응에서 무정형, SBA, MCM 또는 상업적으로 쉽게 이용 가능한 다양한 silica 지지체에 담지된 이온성 액체의 촉매적 적용가능성에 대하여 검토하였다. $CO_2$ 부가반응에 의한 5원환 카보네이트의 합성에 대하여 담지된 이온성 액체의 구조적인 영향과 silica 지지체의 종류에 따른 촉매 활성을 검토한 바, 관능기 또는 금속을 보유한 이온성 액체인 경우에 촉매 성능이 개선됨을 알 수 있었다. 또한 silica에 담지된 이온성 액체(SSIL) 촉매의 재사용성과 반응메커니즘을 조사하여 제시하였다.

Keywords

References

  1. D. G. Gavin and C. J. Bower, Options for reducing greenhouse gases in the global environment, Proc. of the JAPAN-EC, Japan (1991).
  2. S. Inoue, T. Tsuruta, and H. Koinuma, Copolymerzation of carbon dioxide and epoxide, J. Polym. Sci. Polym. Lett., 7(4), 287-292 (1969). https://doi.org/10.1002/pol.1969.110070408
  3. S. Inoue and N. Yamazaki, Organic and Bioorganic Chemistry of Carbon Dioxide, Kodansha Ltd., Tokyo (1981).
  4. S. H. Cho, B. C. Bai, H. R. Yu, and Y. S. Lee, Carbon capture and $CO_2/CH_4$ separation technique using porous carbon materials, Appl. Chem. Eng., 22(5), 343-347 (2011).
  5. U. Romano, Dimethyl carbonate and its production technology, Chim. Ind., 75, 303-306 (1993).
  6. A. A. G. Shaikh and S. Sivaram, Organic carbonates, Chem. Rev., 96(3), 951-976 (1996). https://doi.org/10.1021/cr950067i
  7. K. Weissermel and H. J. Arpe, Industral Organic Chemestry, 3rd ed., Wiley-VCH, New York (1997).
  8. C. E. Song, W. H. Shim, E. J. Roh, and J. H. Choi, Scandium (III) triflate immobilized in ionic liquids: A novel and recyclable catalytic system for Friedel-Crafts alkylation of aromatic compounds with alkenes, Chem. Commun., 17, 1695-1696 (2000).
  9. D. W. Kim, R. Roshan, J. Tharun, K. A. Cherian, and D. W. Park, Catalytic applications of immobilized ionic liquids for synthesis of cyclic carbonates from carbon dioxide and epoxides, Korean J. Chem. Eng., 30(11), 1973-1984 (2013). https://doi.org/10.1007/s11814-013-0193-6
  10. L. Han, S. W. Park, and D. W. Park, Silica grafted imidazolium-based ionic liquids: efficient heterogeneous catalysts for chemical fixation of $CO_{2}$ to a cyclic carbonate, Energy Environ. Sci., 2, 1286-1292 (2009). https://doi.org/10.1039/b910763k
  11. L. Han, H. J. Choi, S. J. Choi, B. Liub, and D. W. Park, 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, 1023-1028 (2011). https://doi.org/10.1039/c0gc00612b
  12. L. Han, M. S. Park, S. J. Choi, Y. J. Kim, S. M. Lee, and D. W. Park, Incorporation of metal ions into silica-grafted imidazolium-based ionic liquids to efficiently catalyze cycloaddition reactions of $CO_{2}$ and epoxides, Catal. Lett., 142, 259-266 (2012). https://doi.org/10.1007/s10562-011-0753-5
  13. J. Q. Wang, D. L. Kong, J. Y. Chen, F. Cai, and L. N. He, Synthesis of cyclic carbonates from epoxides and carbon dioxide over silica-supported quaternary ammonium salts under supercritical conditions, J. Mol. Catal. A: Chem., 249, 143-148 (2006). https://doi.org/10.1016/j.molcata.2006.01.008
  14. J. Q. Wang, X. D. Yue, F. Cai, and L. N. He, Solventless synthesis of cyclic carbonates from carbon dioxide and epoxides catalyzed by silica-supported ionic liquids under supercritical conditions, Catal. Commun., 8, 167-172 (2007). https://doi.org/10.1016/j.catcom.2006.05.049
  15. Y. Kishimoto and I. Ogawa, Amine-catalyzed, one-pot coproduction of dialkyl carbonates and 1,2-Diols from epoxides, alcohols, and carbon dioxide, Ind. Eng. Chem. Res., 43, 8155- 8162 (2004). https://doi.org/10.1021/ie040006n
  16. J. W. Huang and M. Shi, Chemical fixation of carbon dioxide by $NaI/PPh_{3}/PhOH$, J. Org. Chem., 68, 6705-6709 (2003). https://doi.org/10.1021/jo0348221
  17. H. Kawanami, A. Sasaki, K. Matsui, and Y. Ikushima, A rapid and effective synthesis of propylene carbonate using a supercritical $CO_{2}$-ionic liquid system, Chem. Commun., 7, 896-897 (2003).
  18. S. Udayakumar, S. W. Park, D. W. Park, and B. S. Choi, Immobilization of ionic liquid on hybrid MCM-41 system for the chemical fixation of carbon dioxide on cyclic carbonate, Catal. Commun., 9, 1563-1570 (2008). https://doi.org/10.1016/j.catcom.2008.01.001
  19. S. Udayakumar, M. K. Lee, H. L. Shim, S. W. Park, and D. W. Park, Imidazolium derivatives functionalized MCM-41 for catalytic conversion of carbon dioxide to cyclic carbonate, Catal. Commun., 10, 659-664 (2009). https://doi.org/10.1016/j.catcom.2008.11.017
  20. S. Udayakumar, V. Raman, H. L. Shim, and D. W. Park, Cycloaddition of carbon dioxide for commercially-imperative cyclic carbonates using ionic liquid-functionalized porous amorphous silica, Appl. Catal. A: Gen., 368, 97-104 (2009). https://doi.org/10.1016/j.apcata.2009.08.015
  21. M. M. Dharman, H. J. Choi, D. W. Kim, and D. W. Park, Synthesis of cyclic carbonate through microwave irradiation using silica-supported ionic liquids: Effect of variation in the silica support, Catal. Today, 164, 544-547 (2011). https://doi.org/10.1016/j.cattod.2010.11.009