상 이동 촉매상에서 니트로벤젠과 Fe<sub>3</sub>(CO)<sub>12</sub>로부터 아닐린의 합성

천승우; 오소영; 박대원; 박상욱; 신정호

Journal of the Korean Industrial and Engineering Chemistry, Vol.3, No.2, 288-295, June, 1992

Export Citation

상 이동 촉매상에서 니트로벤젠과 Fe₃(CO)₁₂로부터 아닐린의 합성

Synthesis of Aniline from Nitrobenzene and Fe₃(CO)₁₂ with Phase Transfer Catalysts

천승우, 오소영, 박대원, 박상욱, 신정호

초록

Triirondodecacarbonyl에 의한 니트로벤젠의 환원 반응에 상 이동 촉매를 사용한 결과 상온에서 높은 수율의 아닐린을 합성할 수 있었다 Benzyltriethylammonium chloride, tricaprylmethylammonium chloride, 18-crown-6, polyethyleneglycol-400 등이 이 반응에 좋은 상 이동 촉매임을 알 수 있었고, 반응온도, 수용액상의 NaOH 농도, 유기용매가 반응속도 및 아닐린의 수율에 미치는 영향을 고찰하였다.

The reduction of nitrobenzene by triirondodecacarbonyl over phase transfer catalysts was investigated. The phase transfer catalysts showed a good yield of aniline at room temperature. Benzyltriethylammonium chloride, tricaprylmethyl ammonium chloride, 18-crown-6 and polyethyleneglycol-400 were good phase transfer catalysts in this reaction. The effect of reaction temperature, concentration of sodium hydroxide and organic solvents on the reaction rate and yield of aniline were studied in this work.

[References]

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Cho BR, Park SD, Bull. Korean Chem. Soc., 5(3), 126 (1984)
Kimura Y, Regen SL, J. Org. Chem., 48, 1533 (1983)
Regen SL, J. Am. Chem. Soc., 99(11), 3838 (1977)
Ford WT, Adv. Polym. Sci., 55, 49 (1984)
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Sawicki RA, Tetrahedron Lett., 23(22), 2249 (1982)
Tundo P, Venturello P, Ageletti E, J. Am. Chem. Soc., 104, 6551 (1982)
Abbayes H, Alper H, J. Am. Chem. Soc., 99, 98 (1977)
Kimura Y, Tomita Y, Nakanishi S, Otsuji Y, Chem. Lett., 321 (1979)
Alper H, Hachem K, Trans. Metal. Chem., 6, 219 (1981)
Hui KY, Shaw BL, J. Org. Chem., 124, 262 (1977)
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Alper H, Amaratunga S, Tetrahedron Lett., 21, 2603 (1980)
Gaus PL, Gerritz SW, Jeffries PM, Tetrahedron Lett., 29(40), 5083 (1988)
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Chun SW, Oh SY, Park DW, to be published
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[1] Starcks CM, Liotta C, "Phase Transfer Catalysis," Academic Press, N.Y. (1978)

[2] Ageletti E, Tundo P, Venturello PJ, J. Org. Chem., 48, 4106 (1983)

[3] Ger Offen. DE 3,334,8776 (1984)

[4] Evans TL, Synth. Commun., 14, 435 (1984)

[5] Cho BR, Park SD, Bull. Korean Chem. Soc., 5(3), 126 (1984)

[6] Kimura Y, Regen SL, J. Org. Chem., 48, 1533 (1983)

[7] Regen SL, J. Am. Chem. Soc., 99(11), 3838 (1977)

[8] Ford WT, Adv. Polym. Sci., 55, 49 (1984)

[9] Mackenzie WM, Scherrignton DC, Polymer, 22, 431 (1981)

[10] Sawicki RA, Tetrahedron Lett., 23(22), 2249 (1982)

[11] Tundo P, Venturello P, Ageletti E, J. Am. Chem. Soc., 104, 6551 (1982)

[12] Abbayes H, Alper H, J. Am. Chem. Soc., 99, 98 (1977)

[13] Kimura Y, Tomita Y, Nakanishi S, Otsuji Y, Chem. Lett., 321 (1979)

[14] Alper H, Hachem K, Trans. Metal. Chem., 6, 219 (1981)

[15] Hui KY, Shaw BL, J. Org. Chem., 124, 262 (1977)

[16] U.S. Patent, 2,822,397 (1958)

[17] Ger. Offen, 2,320,658 (1975)

[18] Ger. Offen. 2,244,401 (1970)

[19] U.S. Patent, 3,1336,818 (1964)

[20] U.S. Patent, 2,891,094 (1951)

[21] Ger. Offen., 2,208,829 (1972)

[22] Ger. Offen., 2,026,053 (1970)

[23] Becker M, Russell JL, Chem. Eng., 80, 42 (1973)

[24] Alper H, Amaratunga S, Tetrahedron Lett., 21, 2603 (1980)

[25] Gaus PL, Gerritz SW, Jeffries PM, Tetrahedron Lett., 29(40), 5083 (1988)

[26] Darensbourg MY, Darensbourg DJ, Barros HLC, Inorg. Chem., 17(2), 297 (1978)

[27] Chun SW, Oh SY, Park DW, to be published

[28] Marko L, Radhi MA, Otvos I, J. Org. Chem., 218, 369 (1981)

[29] Starks CM, "Phase Transfer Catalysis, New Chemistry, Catalysts and Applications," ACS Symposium Series 326, Chap. 4, ACS, Washington (1987)

[30] Reichardt C, "Solvents and Solvent Effects in Organic Chemistry," 2nd ed., p. 407-410, VCH Publishers, Weinheim (1988)