Cyclohexane and toluene oxidation catalyzed by 1,10-phenantroline Cu(II) complexes

被引:28
作者
Detoni, Chaline [2 ,3 ]
Carvalho, Nakedia M. F. [2 ]
Aranda, Donato A. G. [3 ]
Louis, B. [1 ]
Antunes, O. A. C. [2 ]
机构
[1] Univ Strasbourg, LMSPC, CNRS, UMR 7515,Part European Lab Catalysis & Surface Sc, F-67087 Strasbourg 2, France
[2] Univ Fed Rio de Janeiro, Inst Quim, BR-21945970 Rio De Janeiro, Brazil
[3] Univ Fed Rio de Janeiro, Escola Quim, BR-21941909 Rio De Janeiro, Brazil
关键词
Selective cyclohexane oxidation; Mononuclear Cu(II) complexes; 1,10-Phenantroline; Peroxides; Cyclic voltammetry; COPPER(II) COMPLEXES; MOLECULAR-OXYGEN; IRON(III);
D O I
10.1016/j.apcata.2009.06.027
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this work, we present the cyclohexane oxidation catalyzed by the mononuclear 1,10-phenantroline Cu(II) complexes: [Cu(phen)(3)]Cl-2 center dot 7H(2)O (1), [Cu(phen)(2)Cl]Cl center dot 5H(2)O (2), [Cu(phen)Cl-2] (3), using hydrogen peroxide as oxidant, in acetonitrile:water (3.5:1) solution. The reactions were carried out at temperatures ranging from 25 degrees C to 70 degrees C. All complexes were able to oxidize cyclohexane into cyclohexanol and cyclohexanone with low to moderate yields. Adipic acid was also formed in the reaction. The highest conversion was obtained with the system [Cu(phen)(2)Cl]Cl/H2O2/70 degrees C, with 67% total yield. Furthermore, these complexes were also able to oxidize toluene at room temperature. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:281 / 286
页数:6
相关论文
共 21 条
[1]   Cyclohexane oxidation catalyzed by 2,2'-bipyridil Cu(II) complexes [J].
Canhota, Fernanda P. ;
Salomao, Gisele C. ;
Carvalho, Nakedia M. F. ;
Antunes, O. A. C. .
CATALYSIS COMMUNICATIONS, 2008, 9 (01) :182-185
[2]   Cyclohexane oxidation catalyzed by mononuclear iron(III) complexes [J].
Carvalho, Nakedia M. F. ;
Horn, Adolfo, Jr. ;
Antunes, O. A. C. .
APPLIED CATALYSIS A-GENERAL, 2006, 305 (02) :140-145
[3]   ASPECTS OF METHANE CHEMISTRY [J].
CRABTREE, RH .
CHEMICAL REVIEWS, 1995, 95 (04) :987-1007
[4]   Oxidation of Benzene Catalyzed by 2,2'-Bipyridine and 1,10-Phenantroline Cu(II) Complexes [J].
Detoni, Chaline ;
Carvalho, Nakedia M. F. ;
de Souza, Rodrigo O. M. A. ;
Aranda, Donato A. G. ;
Antunes, O. A. C. .
CATALYSIS LETTERS, 2009, 129 (1-2) :79-84
[5]   CORRELATION OF ABSORPTION SPECTRA AND STRUCTURE OF PSEUDO-OCTAHEDRAL AND TRIGONAL BIPYRAMIDAL COPPER(2)-1,10-PHENANTHROLINE COMPLEXES IN ACETONE SOLUTIONS [J].
FAYE, GH .
CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (18) :2165-&
[6]   FERROCENE AS AN INTERNAL STANDARD FOR ELECTROCHEMICAL MEASUREMENTS [J].
GAGNE, RR ;
KOVAL, CA ;
LISENSKY, GC .
INORGANIC CHEMISTRY, 1980, 19 (09) :2854-2855
[7]  
Jian FF, 2001, CHINESE J CHEM, V19, P772
[8]   Cu(II) bipyridine and phenantroline complexes: Tailor-made catalysts for the selective oxidation of tetralin [J].
Louis, B. ;
Detoni, C. ;
Carvalho, N. M. F. ;
Duarte, C. D. ;
Antunes, O. A. C. .
APPLIED CATALYSIS A-GENERAL, 2009, 360 (02) :218-225
[9]   Probing the catalytic properties of copper(II) complexes of appended cyclams: correlations between catalysis and stability constants or electrochemical properties [J].
Malachowski, MR ;
Dorsey, BT ;
Parker, MJ ;
Adams, ME ;
Kelly, RS .
POLYHEDRON, 1998, 17 (08) :1289-1294
[10]  
Meyer R.J., 1958, Gmelins Handbuch der Anorganischen Chemie, Kupfer Teil BLieferung 1, V8th ed.