Aliquat 336 상이동 촉매하에서 디페닐메탄의 산화에 의한 벤조페논의 합성

박대원; 이화수; 문정열; 박상욱; 신정호

Journal of the Korean Industrial and Engineering Chemistry, Vol.5, No.1, 74-80, February, 1994

Export Citation

Aliquat 336 상이동 촉매하에서 디페닐메탄의 산화에 의한 벤조페논의 합성

Synthesis of Benzophenone by Oxidation of Diphenylmethane under Aliquat 336 as Phase Transfer Catalyst

박대원, 이화수, 문정열, 박상욱, 신정호

초록

본 연구는 Aliquat 336 상이동 촉매와 potassium tert-butoxide 염기를 사용하여 상온에서 디페닐메탄을 산화시켜 벤조페논을 합성하는데 관한 것이다. 4급 암모늄염 촉매 존재하에서는 벤조페논이 합성되지 않는다고 보고된 다른 연구 결과와는 달리 Aliquat 336 촉매로 상온에서 30% 이상의 벤조페논 수율을 얻었다. Aliquat 336 촉매의 양과 potassium tert-butoxide의 양이 증가할수록 디페닐메탄의 전화율이 증가하였다. 산소의 분압이 높을수록 유기용매에 녹아 있는 산소의 농도가 증가하여 전화율과 선택도가 상승하였다. 또한 Aliquat 336 촉매의 역할이 포함된 반응 메카니즘을 제시하였다.

Synthesis of benzophenone by oxidation of diphenylmethane at room temperature is studied using Aliquat 336 as phase transfer catalyst and potassium tert-butoxide as base. No other study has shown that diphenylmethane can be oxidized to benzophenone with quaternary ammonium salt as phase transfer catalyst. However, in presence of Aliquat 336, higher than 30% of benzophenone was yielded. The conversion of diphenylmethane was increased with increasing amount of Aliquat 336 and Potassium tert-butoxide. Higher partial pressure of oxygen favored conversion of diphenylmethane and selectivity of benzophenone by increasing the concentration of oxygen in organic solvent A reaction mechanism involving the role of Aliquat 336 was also proposed.

[References]

Parker AJ, Quart. Rev., 16, 163 (1962)
Cram DJ, Chem. Eng. News, 41, 92 (1963)
Wallace TJ, Schriesheim A, Jacobson N, J. Org. Chem., 29, 2907 (1964)
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Lee HS, Moon JY, Park DW, Park SW, Shin JH, presented for the publication
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Starks CM, Liotta C, "Phase Transfer Catalysis," Academic Press, New York (1978)
Dehmlow EV, Dehmlow SS, "Phase Transfer Catalyst," Verlag Chemie, Weinheim (1983)
Weber WP, Gokel GW, "Phase Transfer Catalysis in Organic Synthesis," Springer-Verlag, Berlin (1977)
Starks CM, "Phase Transfer Catalysis: New Chemistry, Catalysts, and Applications," ACS Symposium Series 326, ACS, Washington (1987)

[Referenced By]

[1] Parker AJ, Quart. Rev., 16, 163 (1962)

[2] Cram DJ, Chem. Eng. News, 41, 92 (1963)

[3] Wallace TJ, Schriesheim A, Jacobson N, J. Org. Chem., 29, 2907 (1964)

[4] Dietrich B, Lehn JM, Tetrahedron Lett., 15, 1225 (1973)

[5] Alneri E, Bollaccio G, Carletti U, Tetrahedron Lett., 24, 2117 (1977)

[6] Feldman D, Rabinovitz M, J. Org. Chem., 53, 3779 (1988)

[7] Neumann R, Sasson Y, J. Org. Chem., 49, 1282 (1984)

[8] Lee HS, Moon JY, Park DW, Park SW, Shin JH, presented for the publication

[9] Halpern M, Sasson Y, Rabinovitz M, J. Org. Chem., 48, 1022 (1983)

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

[11] Dehmlow EV, Dehmlow SS, "Phase Transfer Catalyst," Verlag Chemie, Weinheim (1983)

[12] Weber WP, Gokel GW, "Phase Transfer Catalysis in Organic Synthesis," Springer-Verlag, Berlin (1977)

[13] Starks CM, "Phase Transfer Catalysis: New Chemistry, Catalysts, and Applications," ACS Symposium Series 326, ACS, Washington (1987)