Sulfide oxidation with H2O2 catalyzed by manganese complex of N,N′,N"-tris(2-hydroxypropyl)-1,4,7-triazacyclononane

被引:11
作者
Feng, Xi-mei [1 ]
Wang, Zhen [1 ]
Bian, Ning-sheng [1 ]
Wang, Zhi-lin [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China
基金
中国国家自然科学基金;
关键词
sulfide oxidation; hydrogen peroxide; manganese complex; N,N ',N ''-tris(2-hydroxypropyl)-1,4,7-triazacyclononane;
D O I
10.1016/j.ica.2007.05.055
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
[MnL](ClO4)(2) (L = N, N', N ''-tris(2-hydroxypropyl)-1,4,7-triazacyclononane) has been tested for catalyzing sulfide oxidation. In the presence of this complex, ethyl phenyl sulfide, butyl sulfide and phenyl sulfide are completely oxidized to the corresponding sulfoxides and sulfones with H2O2 as the oxidant. 2-Chloroethyl phenyl sulfide oxidation yield 2-chloroethyl phenyl sulfone and phenyl vinyl sulfone. In ethyl phenyl sulfide oxidation, effects of complex and H2O2 concentration and temperature on the reaction rate have been discussed. Through controlling reaction conditions, ethyl phenyl sulfoxide and ethyl phenyl sulfone may be produced selectively. The UV-Vis and electron paramagnetic resonance (EPR) studies on catalyst solution indicate that metal centre of the complex is transformed from Mn(II) to Mn(IV) after the addition of H2O2. At 25 degrees C, rate constant for ethyl phenyl sulfide oxidation is 4.38 x 10(-3) min(-1). (C) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:4103 / 4110
页数:8
相关论文
共 57 条
[11]  
Bolm C, 1997, SYNLETT, P687
[12]   Catalytic aerobic oxidation of 2-chloroethyl ethylsulfide, a mustard simulant, under ambient conditions - Effect of solvents, ligands, and transition metals on reactivity [J].
Boring, E ;
Geletii, Y ;
Hill, CL .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 176 (1-2) :49-63
[13]   New ligands for manganese catalysed selective oxidation of sulfides to sulfoxides with hydrogen peroxide [J].
Brinksma, J ;
La Crois, R ;
Feringa, BL ;
Donnoli, MI ;
Rosini, C .
TETRAHEDRON LETTERS, 2001, 42 (24) :4049-4052
[14]   Evidence for the formation of an iodosylbenzene(salen)iron active intermediate in a (salen)iron (III)-catalyzed asymmetric sulfide oxidation [J].
Bryliakov, KP ;
Talsi, EP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5228-5230
[15]   Oxidation of thioanisole by peroxomolybdate ions: direct oxygen transfer from tetraperoxomolybdate ion [J].
Bunton, CA ;
Gillitt, ND .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2002, 15 (01) :29-35
[16]   SULFIDE OXIDATION AND OXIDATIVE HYDROLYSIS OF THIOESTERS BY PEROXYMONOSULFATE ION [J].
BUNTON, CA ;
FOROUDIAN, HJ ;
KUMAR, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (01) :33-39
[17]   Oxidation of sulfide, phosphine, and benzyl substrates tethered to N-donor pyridine ligands in carboxylate-bridged diiron(II) complexes [J].
Carson, EC ;
Lippard, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3412-3413
[18]   A HIGH-POTENTIAL MONONUCLEAR MANGANESE(IV) COMPLEX - SYNTHESIS, STRUCTURE, AND PROPERTIES, INCLUDING EPR SPECTROSCOPY AND ELECTROCHEMISTRY, OF [MN(HB(3,5-ME2PYRAZOLYL)3)2](CLO4)2 [J].
CHAN, MK ;
ARMSTRONG, WH .
INORGANIC CHEMISTRY, 1989, 28 (20) :3777-3779
[19]   Oxidative desulphurisation of oils via hydrogen peroxide and heteropolyanion catalysis [J].
Collins, FM ;
Lucy, AR ;
Sharp, C .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 117 (1-3) :397-403
[20]   OXOMANGANESE(IV) PORPHYRINS IDENTIFIED BY RESONANCE RAMAN AND INFRARED-SPECTROSCOPY - WEAK BONDS AND THE STABILITY OF THE HALF-FILLED T2G SUBSHELL [J].
CZERNUSZEWICZ, RS ;
SU, YO ;
STERN, MK ;
MACOR, KA ;
KIM, D ;
GROVES, JT ;
SPIRO, TG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4158-4165