Supported hydrogensulfate ionic liquid catalysis in Baeyer-Villiger reaction

被引:137
作者
Chrobok, Anna [1 ]
Baj, Stefan [1 ]
Pudlo, Wojciech [2 ]
Jarzebski, Andrzej [2 ]
机构
[1] Silesian Tech Univ, Dept Chem Organ Technol & Petrochem, PL-44100 Gliwice, Poland
[2] Silesian Tech Univ, Dept Chem & Proc Engn, PL-44100 Gliwice, Poland
关键词
Immobilisation of ionic liquids; Macroporous silica support; Baeyer-Villiger oxidation; IMMOBILIZATION; OXIDATION; EFFICIENT; MILD;
D O I
10.1016/j.apcata.2009.06.040
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
We report here the method of synthesis and characterisation of ionic liquid: 1-methyl-3-(triethoxysilylpropyl)imidazolium hydrogensulfate, anchored onto solid support via cation-anion stays unbounded to the surface. As a support, we used a silica material with the extensive system of mesa- and macropores. The structure of the support was not destroyed after the immobilisation of the ionic liquid. The new material was tested as acidic catalyst with the Baeyer-Villiger reaction. Cyclic ketones were readily oxidised with 68% hydrogen peroxide in dry dichloromethane to their corresponding lactones in high yields (60-91%) at 50 degrees C within a short time (5-20 h). The use of hydrogen peroxide and a heterogeneous catalyst allows a clean oxidation and the possibility of easy catalyst removal by simple filtration and reuse three times in another oxidation process without lost of catalyst activity. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:22 / 28
页数:7
相关论文
共 26 条
[1]  
BAJ S, 2008, SYNTHETIC COMMUN, V38, P1
[2]   The Baeyer-Villiger oxidation of ketones with bis(trimethylsilyl) peroxide in the presence of ionic liquids as the solvent and catalyst [J].
Baj, Stefan ;
Chrobok, Anna ;
Slupska, Roksana .
GREEN CHEMISTRY, 2009, 11 (02) :279-282
[3]   Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer-Villiger oxidations [J].
Corma, A ;
Nemeth, LT ;
Renz, M ;
Valencia, S .
NATURE, 2001, 412 (6845) :423-425
[4]   Ordered porous materials for emerging applications [J].
Davis, ME .
NATURE, 2002, 417 (6891) :813-821
[5]   [BPy]HSO4 acidic ionic liquid as a novel, efficient, and environmentally benign catalyst for synthesis of 1,5-benzodiazepines under mild conditions [J].
Du, Yuying ;
Tian, Fuli ;
Zhao, Wenzhi .
SYNTHETIC COMMUNICATIONS, 2006, 36 (12) :1661-1669
[6]   Baeyer-Villiger-oxidation of cyclopentanone with aqueous hydrogen peroxide by acid heterogeneous catalysis [J].
Fischer, J ;
Hölderich, WF .
APPLIED CATALYSIS A-GENERAL, 1999, 180 (1-2) :435-443
[7]   Baeyer-Villiger oxidation in supercritical CO2 with potassium peroxomonosulfate supported on acidic silica gel [J].
Gonzalez-Nunez, Maria E. ;
Mello, Rossella ;
Olmos, Andrea ;
Asensio, Gregorio .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6432-6436
[8]   Baeyer-Villiger oxidation with potassium peroxomonosulfate supported on acidic silica gel [J].
González-Nuñez, ME ;
Mello, R ;
Olmos, A ;
Asensio, G .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26) :10879-10882
[9]   Acidic ionic liquid [bmim]HSO4:: An efficient catalyst for acetalization and thioacetalization of carbonyl compounds and their subsequent deprotection [J].
Gupta, Neeraj ;
Sonu ;
Kad, Goverdhan L. ;
Singh, Jasvinder .
CATALYSIS COMMUNICATIONS, 2007, 8 (09) :1323-1328
[10]   A mild and efficient method for preparation of azides from alcohols using acidic ionic liquid [H-NMP]HSO4 [J].
Hajipour, Abdol R. ;
Rajaei, Asiyeh ;
Ruoho, Arnold E. .
TETRAHEDRON LETTERS, 2009, 50 (06) :708-711