생체모방계에 의한 시클로헥산 산화반응에서 리간드의 영향

김성보; Seong-Bo Kim

Korean Chemical Engineering Research, Vol.43, No.2, 202-205, April, 2005

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생체모방계에 의한 시클로헥산 산화반응에서 리간드의 영향

Influence of Ligand on Oxidation of Cyclohexane in the Biomimetic System

김성보 ^†

한국화학연구원 화학기술부 환경자원가술연구팀, 305-600 대전시 유성구 장동 100

Seong-Bo Kim^†

Korea Research Institute of Chemical Technology, 100, Jang-dong, Yuseong-gu, Daejeon 305-600, Korea

E-mail:

초록

GoAgg 생체모방계 산화반응시스템을 이용하여 상온, 상압에서 시크로헥산을 산화 반응하여 시크로헥산올과 시클로 헥산온 제조를 위한 연구를 수행하였다. 반응속도론적 연구를 수행하였으며 리간드로 카르복실기를 포함하는 picolinic acid를 사용한 경우 철 촉매만 사용한 경우에 비해 15배 이상의 활성이 증가하였다. 특히 피리딘환이나 이미다졸환에 ortho 위치에 카르복실기를 포함한 경우 meta, para 위치보다 반응성이 크게 증가하였다. 이 결과로부터 새로운 매커니 즘을 제안하였다.

The effects of ligands on reactivity under GoAgg oxidation system have been studied. Picolinic acid containing carboxylic acid showed the most excellent activity among various ligands. Also, Picolinic acid of ortho position carboxylic group in pyridine ring largely increased reaction rates in the GoAgg oxidation systems. From these results, we proposed the new mechanism on the GoAgg oxidation using ligands having carboxylic group at ortho position.

Keywords:Biomimetic System;Oxidation;Cyclohexane;GoAgg Reacyion;Picolinic Acid

[References]

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Sugimoto H, Tung HC, Saywer DT, J. Am. Chem. Soc., 110(8), 2465 (1988)
Archakov AI, Bachmanopva GI, Cytochrome P-450 and Active Oxygen, Taylor & Francis, London (1990)
Groves JT, Nemo TE, Meyers RS, J. Am. Chem. Soc., 101(4), 1032 (1979)
Barton DHR, Biviere SD, Chavasiri W, Csuhai E, Doller D, J. Am. Chem. Soc., 114(6), 2147 (1992)
Collman JP, Brauman JI, Meunier B, Hayashi T, Kodadek T, Raybuck SA, J. Am. Chem. Soc., 107(7), 2000 (1985)
Barton DHR, Gastiger MJ, Motherwell WB, J. Chem. Soc. Chem. Commun., 41, 41 (1983)
Barton DHR, Lee KW, Mehl W, Ozbalik N, Zhang L, Tetrahedron, 46(11), 3753 (1990)
Nolte RJM, Razenberg JASJ, Schurman R, J. Am. Chem. Soc., 108(10), 2751 (1986)
Dicken CM, Woon TC, Bruce TC, J. Am. Chem. Soc., 101(5), 1032 (1979)
Mansuy D, Bartoli JF, Moneteau M, Tetrahedron Lett., 23(27), 2781 (1982)

[Related Articles]

[1] Traylor TG, Xu F, J. Am. Chem. Soc., 109(9), 2770 (1987)

[2] Sugimoto H, Tung HC, Saywer DT, J. Am. Chem. Soc., 110(8), 2465 (1988)

[3] Archakov AI, Bachmanopva GI, Cytochrome P-450 and Active Oxygen, Taylor & Francis, London (1990)

[4] Groves JT, Nemo TE, Meyers RS, J. Am. Chem. Soc., 101(4), 1032 (1979)

[5] Barton DHR, Biviere SD, Chavasiri W, Csuhai E, Doller D, J. Am. Chem. Soc., 114(6), 2147 (1992)

[6] Collman JP, Brauman JI, Meunier B, Hayashi T, Kodadek T, Raybuck SA, J. Am. Chem. Soc., 107(7), 2000 (1985)

[7] Barton DHR, Gastiger MJ, Motherwell WB, J. Chem. Soc. Chem. Commun., 41, 41 (1983)

[8] Barton DHR, Lee KW, Mehl W, Ozbalik N, Zhang L, Tetrahedron, 46(11), 3753 (1990)

[9] Nolte RJM, Razenberg JASJ, Schurman R, J. Am. Chem. Soc., 108(10), 2751 (1986)

[10] Dicken CM, Woon TC, Bruce TC, J. Am. Chem. Soc., 101(5), 1032 (1979)

[11] Mansuy D, Bartoli JF, Moneteau M, Tetrahedron Lett., 23(27), 2781 (1982)