Oxidation of 2-aminophenol with molecular oxygen and hydrogen peroxide catalyzed by water soluble metalloporphyrins

被引:21
作者
El-Khalafy, Sahar H. [1 ]
Hassanein, M. [1 ]
机构
[1] Tanta Univ, Fac Sci, Dept Chem, Tanta 31527, Egypt
关键词
Catalytic oxidation; 2-Aminophenol; Metalloporphyrins; 2-Aminophenoxazine-3-one; MANGANESE(III) PORPHYRIN; COMPLEXES; MECHANISM; DIOXYGEN; KINETICS; HYDROXYLATION; ACTIVATION; ALKANES;
D O I
10.1016/j.molcata.2012.06.002
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
5,10,15,20-Tetrakis-(p-sulfonatophenyl)porphinatocobalt(II) and 5,10,15,20-tetrakis-(p-sulfonatophenyl)porphinatomanganese(III) chloride have been used as catalysts for the oxidative coupling of 2-aminophenol to 2-aminophenoxazine-3-one with molecular oxygen and hydrogen peroxide. The effects of pH and concentration of catalysts, hydrogen peroxide and oxygen on the oxidation reaction and yield of 2-aminophenoxazine-3-one have been studied. The oxidation of 2-aminophenol with molecular oxygen catalyzed by cobalt(II) tetra(4-sulfophenyl)porphyrin involves a hydrogen atom abstraction from 2-aminophenol by cobalt(II) superoxo species. UV-vis analysis indicated that oxomanganese(IV) is the active species in the oxidation of 2-aminophenol with hydrogen peroxide and manganese(III)tetra(4-sulfophenyl)porphyrin. (c) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:148 / 152
页数:5
相关论文
共 51 条
[1]  
[Anonymous], METALLOPORPHYRINS CA
[2]   SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].
ARNDTSEN, BA ;
BERGMAN, RG ;
MOBLEY, TA ;
PETERSON, TH .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162
[3]  
Benedini F., 1963, J CHEM SOC PERK T, V2, P1985
[5]   A MECHANISTIC STUDY OF THE OXIDATION OF PHENOLS IN AQUEOUS-SOLUTION BY OXOIRON(IV) TETRA(N-METHYLPYRIDYL)PORPHYRINS - A MODEL FOR HORSERADISH-PEROXIDASE COMPOUND-II [J].
COLCLOUGH, N ;
SMITH, JRL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (06) :1139-1149
[6]  
DEVISMES B, 1986, NEW J CHEM, V10, P81
[7]   Potential applications of oxidative enzymes and phenoloxidase-like compounds in wastewater and soil treatment:: a review [J].
Durán, N ;
Esposito, E .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2000, 28 (02) :83-99
[8]  
El-Salty S.A., 2002, COLLOID SURFACE A, V203, P217
[9]  
Forstin-Rio M., 1984, J CHEM SOC PERK T, V1, P1971
[10]  
FREI E, 1974, CANCER CHEMOTH REP 1, V58, P49