Issue
Korean Journal of Chemical Engineering,
Vol.14, No.6, 507-512, 1997
Application of Quaternary Ammonium Salt as Catalyst in the Reaction of Glycidyl Methacrylate with CO2
This study is related to the investigation of the characteristics of quaternary ammonium salt catalyst on the addition reaction of carbon dioxide and glycidyl methacrylate (GMA) to form (2-oxo-1,3-dioxolan-4-yl) methyl methacrylate (DOMA). Among the salts tested, the ones with higher alkyl chain length and with more nucleophilic counter anion showed a higher catalytic activity. The DOMA monomer was obtained in non polar solvent like toluene and cyclohexane, while poly (DOMA) could be directly obtained in aprotic dipolar solvent such as DMF. In order to facilitate recovery of catalyst, polymer-immobilized quaternary ammonium salt was prepared by copolymerization of styrene (ST, divinylbenzene (DVB) and vinyl benzene chloride (VBC). The catalyst with 2 wt% of DVB, 25 wt% of VBC and quaternized tributyl amine showed the highest catalytic activity, and its activity was maintained even up to 10 successive experimental runs.
[References]
  1. Inoue S, Yamazaki N, Higashi F, "Organic and Bioorganic Chemistry of Carbon Dioxide," Kodansha Ltd., Tokyo, 1982
  2. Kihara N, Endo T, Macromolecules, 25, 4824, 1992
  3. Kihara N, Endo T, Makromol. Chem., 193, 1482, 1992
  4. Kihara N, hara N, Endo T, J. Org. Chem., 58, 6198, 1993
  5. Moon JY, Yang JG, Jung SM, Park DW, Lee JK, React. Kinet. Catal. Lett., 61(2), 315, 1997
  6. Nishikubo T, Kameyama A, Sasano M, J. Polym. Sci. A: Polym. Chem., 32(2), 301, 1994
  7. Nishikubo T, Kameyama A, Yamashita I, Tomoi M, Fukuda W, J. Polym. Sci. A: Polym. Chem., 31, 939, 1993
  8. Nomura R, Ninagawa A, Matsuda H, J. Org. Chem., 45, 3735, 1980
  9. Park DW, Park SW, Kaseger CF, Moon JY, Lee JB, React. Kinet. Catal. Lett., in press, 1997
  10. Park DW, Moon JY, Yang JG, Lee JK, Energy Conv. Manag., 38, S449, 1997
  11. Perry RH, Green D, "Perry's Chemical Engineers' Handbook," 6th ed., Macgraw-Hill, 1984
  12. Rokichi G, Kuran W, Marciniak BP, Monat. Chem., 115, 205, 1984
  13. Starks CM, Liotta CL, Halpern M, "Phase Transfer Catalysis," Chapman & Hall, New York, 1994
  14. Tomoi M, Ford WT, J. Am. Chem. Soc., 103(13), 3821, 1981