폴리에틸렌글리콜 상이동 촉매상에서 니트로벤젠과 Fe(CO)5로부터의 아닐린 합성

오소영; 천승우; 박대원; 박상욱; 신정호

Journal of the Korean Industrial and Engineering Chemistry, Vol.3, No.4, 620-626, December, 1992

Export Citation

폴리에틸렌글리콜 상이동 촉매상에서 니트로벤젠과 Fe(CO)5로부터의 아닐린 합성

Synthesis of Aniline from Nitrobenzene and Fe(CO)₅ with Polyethyleneglycol as Phase Transfer Catalyst

오소영, 천승우, 박대원, 박상욱, 신정호

초록

Ironpentacarbonyl에 의한 니트로벤젠의 환원반응에 PEG를 상이동 촉매로 사용한 결과 상온에서 90% 이상의 아닐린 수율을 얻을 수 있었다. 니트로벤젠의 반응속도는 PEG의 사슬길이와 결합점의 수에 의존하였으며 NaOH의 농도가 높고 용매의 극성이 커질수록 증가하였다. 그러나 아닐린의 수율은 NaOH농도가 2N일때 최대였으며 그 이상의 농도 에서는 감소하였다

PEG phase transfer catalyzed reduction of nitrobenzene with Fe(CO)₅ afforded aniline up to over 50% yield al room temperature. The reaction rate of nitrobenzene was dependent on the chain length and number of binding sites of PEG, and it was increased with the concentration of NaOH and solvent polarity. But the yield of aniline was maximum) with 2N NaOH solution and it was decreased at higher concentrations.

[References]

Starks CM, Liotta C, "Phase Transfer Catalysis," Academic Press, New York (1978)
Ageletti E, Tundo P, Venturello PJ, Org. Chem., 48, 4106 (1983)
Ger Offen. DE 3,334,8776 (1984)
Evans TL, Synth. Commun., 14, 435 (1984)
Cho BR, Park SD, Bull. Korean Chem. Soc., 5, 126 (1984)
Kimura Y, Regen SL, J. Org. Chem., 48, 1533 (1983)
Freedman HH, Pure Appl. Chem., 58, 857 (1986)
Gokel GW, Goli PM, Schultz RA, J. Org. Chem., 48, 2837 (1983)
Abbayes H, Alper H, J. Am. Chem. Soc., 99, 98 (1977)
Kimura Y, Tomita Y, Nakanishi S, Otsuji Y, Chem. Lett., 321 (1979)
Hui KY, Shaw BL, J. Org. Chem., 124, 262 (1977)
Harris JM, Hundley NH, Shannon TG, Struck EC, J. Org. Chem., 47, 4789 (1982)
Starks CM, ACS Symposium Series 326, p. 27, ACS, Washington (1987)
Schultz RA, Dishong DM, Gokel GW, J. Am. Chem. Soc., 104, 625 (1982)
Laszlo M, Mazin AR, Irma O, J. Org. Chem., 218, 369 (1981)
Darensbourg MY, Darensbourg DJ, Barros HLC, Inorg. Chem., 17, 297 (1978)
Tanguy G, Weinberg B, Abbayas H, Tetrahedron Lett., 24, 4005 (1983)
Gans PL, Samuel WG, Patrick MJ, Tetrahedron Lett., 29, 5083 (1988)
Reichardt C, "Solvents and Solvent Effects in Organic Chemistry," 2nd ed., p. 407-410, VCH Publishers, Weinheim (1988)

[Referenced By]

[1] Starks CM, Liotta C, "Phase Transfer Catalysis," Academic Press, New York (1978)

[2] Ageletti E, Tundo P, Venturello PJ, 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, 126 (1984)

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

[7] Freedman HH, Pure Appl. Chem., 58, 857 (1986)

[8] Gokel GW, Goli PM, Schultz RA, J. Org. Chem., 48, 2837 (1983)

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

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

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

[12] Harris JM, Hundley NH, Shannon TG, Struck EC, J. Org. Chem., 47, 4789 (1982)

[13] Starks CM, ACS Symposium Series 326, p. 27, ACS, Washington (1987)

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

[15] Laszlo M, Mazin AR, Irma O, J. Org. Chem., 218, 369 (1981)

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

[17] Tanguy G, Weinberg B, Abbayas H, Tetrahedron Lett., 24, 4005 (1983)

[18] Gans PL, Samuel WG, Patrick MJ, Tetrahedron Lett., 29, 5083 (1988)

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