상이동 촉매에 의한 Phenyl Glycidyl Ether와 이산화탄소의 부가반응

박대원; 문정열; 양정규; 박성훈; 이진국

Journal of the Korean Industrial and Engineering Chemistry, Vol.7, No.1, 26-33, February, 1996

Export Citation

상이동 촉매에 의한 Phenyl Glycidyl Ether와 이산화탄소의 부가반응

Addtion Reaction of Phenyl Glycidyl Ether with Carbon Dioxide Using Phase Transfer Catalysts

박대원, 문정열, 양정규, 박성훈, 이진국

초록

본 연구는 이산화탄소와 phenyl glycidyl ether(PGE)의 부가반응에 대하여 상이동 촉매의 특성을 고찰한 것이다. 4급 암모늄염 상이동 촉매의 경우 알킬기의 크기가 크고 짝이온의 친수성이 강할수록 좋은 촉매활성을 나타내었다. 폴리에틸렌글리콜과 crown ether도 NaI와 함께 사용한 결과 효율적인 촉매임을 알 수 있었다. 이산화탄소의 압력이 증가하면 용매인 NMP에 대한 CO₂의 용해도가 증가하여 PGE의 전화율이 증가하였다. 또한 상이동 촉매의 역할이 포함된 반응메카니즘을 제시하였다.

This study is related to the investigation of the characteristics of phase transfer catalysts on the addition reaction of carbon dioxide and phenyl glycidyl ether(PGE). Quaternary ammonium salts showed a good conversion of PGE at l atm of CO₂. Among the quaternary ammonium salts tested, the ones with higher alkyl chain length and with more hydrophilic counter anion showed higher catalytic activity. Polyethylene glycol and crown ether were also effective catalysts when they are used with NaI. High pressure of CO₂ increased the conversion of PGE by increasing solubility of CO₂ in NMP. A mechanism of the reaction involving the role of phase transfer catalyst was also proposed.

[References]

Choi MJ, Lee KW, Catalysis, 11, 77 (1995)
Reichardt C, "Solvents and Solvent Effects in Organic Chemistry," VCH, Weinheim, 2nd edition (1988)
Katz HE, Macromolecules, 20, 2026 (1987)
Nomura R, Kori M, Matsuda H, Makromol. Chem. Rapid Commun., 9, 739 (1988)
Rokicki G, Pawlicki J, Kuran W, Polym. J., 17, 509 (1985)
Rokicki G, Jezewski P, Polym. J., 20, 409 (1988)
Rokicki G, Kuran W, Marcinak BP, Monat. Chem., 115, 205 (1984)
Kihara N, Endo T, J. Chem. Soc.-Chem. Commun., 937 (1994)
Kihara N, Endo T, Makromol. Chem., 193, 1481 (1992)
Starks CM, Liotta CL, Halpern M, "Phase Transfer Catalysis," Chapman & Hall, New York (1994)
Heriott AW, Picker D, J. Am. Chem. Soc., 97, 2345 (1975)
Kihara N, Hara N, Endo T, J. Org. Chem., 58, 6198 (1993)
Dehmlow EV, Lissel M, Tetrahedron Lett., 1783 (1983)
Sasson Y, Zahalka HA, Can. J. Chem., 67, 245 (1989)
Schultz RA, Dishong DM, Gokel GW, J. Am. Chem. Soc., 104, 625 (1982)
Lincoln SF, Brereton IM, Spotswood TM, J. Am. Chem. Soc., 108, 8134 (1986)

[Referenced By]

[1] Choi MJ, Lee KW, Catalysis, 11, 77 (1995)

[2] Reichardt C, "Solvents and Solvent Effects in Organic Chemistry," VCH, Weinheim, 2nd edition (1988)

[3] Katz HE, Macromolecules, 20, 2026 (1987)

[4] Nomura R, Kori M, Matsuda H, Makromol. Chem. Rapid Commun., 9, 739 (1988)

[5] Rokicki G, Pawlicki J, Kuran W, Polym. J., 17, 509 (1985)

[6] Rokicki G, Jezewski P, Polym. J., 20, 409 (1988)

[7] Rokicki G, Kuran W, Marcinak BP, Monat. Chem., 115, 205 (1984)

[8] Kihara N, Endo T, J. Chem. Soc.-Chem. Commun., 937 (1994)

[9] Kihara N, Endo T, Makromol. Chem., 193, 1481 (1992)

[10] Starks CM, Liotta CL, Halpern M, "Phase Transfer Catalysis," Chapman & Hall, New York (1994)

[11] Heriott AW, Picker D, J. Am. Chem. Soc., 97, 2345 (1975)

[12] Kihara N, Hara N, Endo T, J. Org. Chem., 58, 6198 (1993)

[13] Dehmlow EV, Lissel M, Tetrahedron Lett., 1783 (1983)

[14] Sasson Y, Zahalka HA, Can. J. Chem., 67, 245 (1989)

[15] Schultz RA, Dishong DM, Gokel GW, J. Am. Chem. Soc., 104, 625 (1982)

[16] Lincoln SF, Brereton IM, Spotswood TM, J. Am. Chem. Soc., 108, 8134 (1986)