Carboxylation of aromatic compounds in a supercritical carbon dioxide medium

作者: A. V. Shlyakhtin , S. Z. Vatsadze , D. P. Krut’ko , D. A. Lemenovskii , M. V. Zabalov

DOI: 10.1134/S199079311207007X

关键词:

摘要: The reaction of direct carboxylation benzene and its derivatives PhX (X = Me, Br, Ph, OPh, OMe), as well mesitylene, durene, ferrocene, in a supercritical CO2 medium the presence various Lewis acids (AlCl3, FeCl3, ZrCl4, ZnCl2) is studied. It shown that, all cases, secondary reactions proceed faster than primary carboxylic acid formation. For thoroughly studied AlCl3-CO2toluene system, optimal conditions formation n-toluic are determined. AlCl3-CO2-benzene an example, quantum-chemical calculations characteristics allowed pathways performed.

参考文章(16)
William Tumas, Joseph M. DeSimone, Green chemistry using liquid and supercritical carbon dioxide Oxford University Press. ,(2003)
Saul Patai, The chemistry of carboxylic acids and esters UMI Books on Demand. ,(1969)
Wilfred Louis Florio Armarego, Douglas Dalzell Perrin, D. R Perrin, Purification of laboratory chemicals ,(1966)
Takayuki Iijima, Tatsuaki Yamaguchi, K2CO3-catalyzed direct synthesis of salicylic acid from phenol and supercritical CO2 Applied Catalysis A-general. ,vol. 345, pp. 12- 17 ,(2008) , 10.1016/J.APCATA.2008.03.037
Eric J Beckman, Supercritical and near-critical CO2 in green chemical synthesis and processing Journal of Supercritical Fluids. ,vol. 28, pp. 121- 191 ,(2004) , 10.1016/S0896-8446(03)00029-9
John P. Perdew, Kieron Burke, Matthias Ernzerhof, Generalized Gradient Approximation Made Simple Physical Review Letters. ,vol. 77, pp. 3865- 3868 ,(1996) , 10.1103/PHYSREVLETT.77.3865
Pradip Munshi, Eric J. Beckman, Effect of Incubation of CO2 and Lewis Acid on the Generation of Toluic Acid from Toluene and CO2 Industrial & Engineering Chemistry Research. ,vol. 48, pp. 1059- 1062 ,(2009) , 10.1021/IE801524E
Yutaka Suzuki, Tetsutaro Hattori, Tomohiro Okuzawa, Sotaro Miyano, Lewis Acid-Mediated Carboxylation of Fused Aromatic Compounds with Carbon Dioxide Chemistry Letters. ,vol. 2002, pp. 102- 103 ,(2002) , 10.1246/CL.2002.102
Matthias Ernzerhof, Gustavo E. Scuseria, Assessment of the Perdew–Burke–Ernzerhof exchange-correlation functional Journal of Chemical Physics. ,vol. 110, pp. 5029- 5036 ,(1999) , 10.1063/1.478401