Reaction Kinetics of Carbon Dioxide and Glycidyl Methacrylate using a Ionic Liquid Catalyst of Imidazole Immobilized on MCM41

MCM41에 담지된 Imidazole 촉매에 의한 Glycidyl Methacrylate와 이산화탄소의 반응속도론

  • Son, Young-Sik (Division of Chemical Engineering, Pusan National University) ;
  • Park, Moon-Ki (Department of Pharmaceutical Engineering, Daegu Haany University) ;
  • Kim, Gun-Woo (Business Environment Improvement Division, Busan-Ulsan Regional Office of Small and Medium Business Administration) ;
  • Park, Sang-Wook (Division of Chemical Engineering, Pusan National University)
  • 손영식 (부산대학교 화학공학과) ;
  • 박문기 (대구한의대학교 한방제약공학과) ;
  • 김건우 (부산울산지방중소기업청 기업환경개선과) ;
  • 박상욱 (부산대학교 화학공학과)
  • Received : 2009.03.25
  • Accepted : 2009.06.18
  • Published : 2009.08.31

Abstract

Carbon dioxide was absorbed into GMA solution in a stirred flat cell using mesoporous catalyst Imidazole-CP-MS41, which was synthesized by CP-MCM41 with imidazole. Experiments were carried out at a batch-type absorber with different conditions, varying reaction temperature, concentration of GMA, solvent but maintaining 50 rpm of agitation speed and 2 g of catalyst. Absorption rate of $CO_2$ was used to obtain the kinetics based on the film theory using zwitterion mechanism with 2 elementary reaction and the kinetics were correlated with the solubility parameter of the solvents.

중간세공크기(mesopore)의 MCM41에 Imidazole을 담지시킨 CP-MS41 고체 입자의 촉매를 사용하여 GMA 용액에 $CO_2$를 흡수시켜 $CO_2$의 흡수기구로부터 GMA와 $CO_2$의 반응속도론을 고찰하였다. 대기압에서 회분식 흡수조를 사용하여 임펠러의 교반속도, 50 rpm, 촉매, 2 g, 반응온도, 60, 70, $80^{\circ}C$, GMA의 농도, $0.1{\sim}3.0kmol/m^3$, 용제, DMA, NMP, DMSO에서 측정한 $CO_2$의 흡수속도와 경막설에 의한 물질수지식을 사용하여 반응속도상수를 구하였다.

Keywords

Acknowledgement

Supported by : 대구한의대학교

References

  1. Peppel, W. J., "Preparation and Properties of the Alkylene Carbonates," Ind. Eng. Chem., 50, 767-770(1958) https://doi.org/10.1021/ie50581a030
  2. Rokicki, G. and Jezewski, P., "Polycarbonates from Cyclic Carbonates, Carbanions and Dihalo Compounds," Polym. J., 20, 499-509(1988) https://doi.org/10.1295/polymj.20.499
  3. Kihara, N. and Endo, T., "Incorporation of Carbon Dioxide Into Poly(glycidyl methacrylate)," Macromolecules, 25, 4824-4825(1992) https://doi.org/10.1021/ma00044a053
  4. Nishikubo, T., Kameyama, A., Yamashita, J., Tomoi, M. and Fukuda, W., "Insoluble Polystyrene-bound Quaternary Onium Salt Catalysts for the Synthesis of Cyclic Carbonates by the Reaction of Oxiranes with Carbon Dioxide," J. Polym. Sci., Part A, Polym. Chem., 31, 939-947(1993) https://doi.org/10.1002/pola.1993.080310412
  5. Nishikubo, T., Kameyama, A., Yamashida, J., Hukumitsu, T., Maejima, C. and Tomoi, M., “Soluble Polymer-supported Catalysts Containing Pendent Quaternary Onium Salys for the Addition Reaction of Oxiranes with Catbon Dioxide,” J. Polym. Sci., Part A, Poly. Chem., 33, 1011(1995) https://doi.org/10.1002/pola.1995.080330702
  6. Yamazaki, N., Iguchi, T. and Hicashi, F., 'Studies on Reactions of N-phosphonium Salts of Pyridines. XII. Direct Polycondensation Reaction of Carbon Dioxide or Disulfide with Diamines Under Mild Condition,' J. Polym. Sci., Part A, Poly. Chem., 13, 785-795(1975) https://doi.org/10.1002/pol.1975.170130402
  7. Kihara, N., Hara, N. and Endo, T., "Catalytic Activity of Various Salts in the Reaction of 2,3-epoxy Propyl Phenyl Ether and Carbon Dioxide Under Atmospheric Pressure," J. Org. Chem., 58, 6198-6202(1993) https://doi.org/10.1021/jo00075a011
  8. Aida, T. and Inoue, S., "Activation of Carbon Dioxide with Aluminum Porphyrine and Reaction with Epoxide Having a Long Oxyalkylene Chain as the Alkoxide Group," J. Am. Chem. Soc., 105, 1304-1309(1983) https://doi.org/10.1021/ja00343a038
  9. Endo, T., Nagai, D., Manma, T., Yamaguchi, H. and Ochiai, B., "A Novel construction of a Reversible Fixation-release System of Carbon Dioxide by Amidines and Their Polymers," Macromolecules, 37, 2007-2009(2004) https://doi.org/10.1021/ma0305479
  10. Doraiswamy, L. K. and Sharma, M. M., Heterogeneous reactions, vol.1, John Wiley & Sons, Inc., New York(1984)
  11. Park, S. W., Park, D. W., Kim, T .Y. and Lee, J. W., "Chemical Absorption of Carbon Dioxide into Toluene Solution of Oxirane", Stud. Surf. Sci. Catal., 153, 535-538(2004) https://doi.org/10.1016/S0167-2991(04)80309-4
  12. Park, S. W., Park, D. W., Kim, T. Y., Park, M. Y. and Oh, K. J., "Chemical Kinetics of the Reaction Between Carbon Dioxide and Phenyl Glycidyl Ether Using Aliquat 336 as a Catalyst," Catal. Today, 98, 493-498(2004) https://doi.org/10.1016/j.cattod.2004.09.002
  13. Park, S. W., Choi, B. C., Park, D. W. and Kim, S. S., 'Kinetics of the Reaction between Carbon Dioxide and Glycidyl Methacrylate Using 18-crown-6 as a Catalyst,' J. Ind. Eng. Chem., 11, 527-532 (2005)
  14. Park, S. W. and Lee, J. W., "Effect of Solvent on Reaction Rate Constant of Reaction Between Carbon Dioxide and Glycidyl Methacrylate Using Aliquat 336 as a Catalyst," Stud. Surf. Sci. Catal., 159, 345-348(2006) https://doi.org/10.1016/S0167-2991(06)81604-6
  15. Park, D. W., Mun, N. Y., Kim, K. H., Kim, I. and Park, S. W., "Addition of Carbon Dioxide to Allyl Glycidyl Ether Using Ionic Liquids Catalysts," Catal. Today, 115, 130-133(2006) https://doi.org/10.1016/j.cattod.2006.02.054
  16. Park, S. W., Park, D. W. and Lee, J. W., "Reaction Rate of Carbon Dioxide in Glycidyl Methacrylate Solution Using Tricarylylmethylammonium Chloride as a Catalyst," Korean J. Chem. Eng., 23, 645-649(2006) https://doi.org/10.1007/BF02706808
  17. Park, S. W., Choi, B. S., Lee, B. D., Park, D. W. and Kim, S. S., "Chemical Absorption of Carbon Dioxide into Glycidyl Methacrylate Solution with Tetrabutylammonium Bromide," Sep. Sci. Technol., 41, 829-839(2006) https://doi.org/10.1080/01496390600588929
  18. Park, S. W., Choi, B. C., Park, D. W., Kim, S. S. and Lee, J. W., "Kinetic Parameters Using an Immobilized Tetrahexylammonium Chloride Catalyst in Glycidyl Methacrylate Reaction with Carbon Dioxide," Korean J. Chem. Eng., 24, 953-959(2007) https://doi.org/10.1007/s11814-007-0104-9
  19. Park, S. W., Choi, B. C., Park, D. W. and Lee, J. W., "Reaction Kinetics of the reaction Between Carbon Dioxide and Glycidyl Methacrylate Using Tetraoctylammonium Chloride as Catalyst," React. Kinet. Catal. Lett, 90, 215-223(2007) https://doi.org/10.1007/s11144-007-4971-1
  20. Park, S. W., Choi, B. C., Park, D. W., Oh, K. J. and Lee, J. W., "Reaction Kinetics of Carbon Dioxide with Glycidyl Methacrylate Using Tributylamine Supported on Poly(styrene-co-vinylbenzyl chloride as a catalyst)," Green Chemistry, 9, 605-610(2007) https://doi.org/10.1039/b613618d
  21. Park, S. W., Choi, B. C., Park, D. W. and Lee, J. W., "Reaction Kinetics of Carbon Dioxide with Glycidyl Methacrylate Using Immolilized Trioctylamine Supported on Poly(styrene-co-vinylbenzyl chloride as a catalyst)," React. Kinet. Catal. Lett, 91, 101-110 (2007) https://doi.org/10.1007/s11144-007-5033-4
  22. Park, S. W., Choi, B. C., Park, D. W., Udayakumar, S. and Lee, J. W., "Reaction Kinetics for Poly(styrene-co-vinylbenzyl chloride)-Supported Catalyst Containing Pendant Tetraethylammonium Chloride in the Reaction of Glycidyl Methacrylate with Carbon Dioxide," Catal. Today, 131, 559-565(2008) https://doi.org/10.1016/j.cattod.2007.10.037
  23. Udayakumar, S., Park, S. W., Park, D. W. and Choi, B. S., "Immobilization of Ionic Liquid on Hybrid MCM-41 System for the Chemical Fixation of Carbon Dioxide on Cyclic Catbonate," Catal. Commun., 9, 1563-1570(2008) https://doi.org/10.1016/j.catcom.2008.01.001
  24. Alper, E., Al-Hamed, A. and Shaikh, A. A., 'Kinetics and Selectivity of Carbon dioxide Absorption by Aqueous Methyl-diethanolamine Solutions,' Proc. Int. Chem. React. Eng. Conf., 2, 17-23(1987)
  25. Reid, R. C., Prausnitz, J. M. and Sherwwod, T. K., The properties of Gases and Liquid, McGraw-Hill Book Company, New York(1977)
  26. Cussler, E. L., Diffusion, Cambridge University Press, NewYork(1984)
  27. Kennard, M. L. and Meisen, A., "Solubility of Carbon Dioxide in Aqueous Diethanolamine Solutions at Elevated Temperature and Pressures," J. Chem. Eng. Data, 29, 309(1984) https://doi.org/10.1021/je00037a025
  28. Carta, G. and Pigford, R. L., "Absorption of Nitric Oxide in Nitric Acid and Water," Ind. Eng. Chem. Fundam., 22, 329(1983) https://doi.org/10.1021/i100011a011
  29. Herbrandson, H. F. and Neufeld, F. R., "Organic Reactions and the Critical Energy Density of the Solvent. The Solubility Parameter, $\delta$, as a New Solvent Parameter," J. Org. Chem., 31, 1140-1143(1966) https://doi.org/10.1021/jo01342a036
  30. Brandrup, J. and Immergut, E. H., Polymer Handbook, Second Ed., John Wiley & Sons, New York(1975)