Nitration of aromatic compounds with NO2/air catalyzed by sulfonic acid-functionalized ionic liquids

被引:74
作者
Cheng, Guangbin [1 ]
Duan, Xuelei [1 ]
Qi, Xiufang [1 ]
Lu, Chunxu [1 ]
机构
[1] Nanjing Univ Sci & Technol, Dept Chem, Sch Chem Engn, Nanjing 210094, Peoples R China
关键词
Nitration; NO2/air; Ionic liquid;
D O I
10.1016/j.catcom.2008.08.019
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
Nitration of aromatic compounds with NO2/air catalyzed by sulfonic acid-functionalized ionic liquid under solvent-free conditions is reported. A variety of ionic liquids [BSPy][HSO4], [BSPy][TfO], and [BSPy][pTSA] ([BSPy] = N-(4-hydroxsulfonylbutyl) pyridinium) were prepared. Their acidities were further investigated by Hammett method and the acidity-catalytic relationship was discussed. It was found that satisfactory results were obtained with [BSPy][HSO4], Ionic liquids could be conveniently separated with the products and reused for five times with excellent yield of mono-nitration products and para-selectivity. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:201 / 204
页数:4
相关论文
共 27 条
[11]   Application of functional ionic liquids possessing two adjacent acid sites for acetalization of aldehydes [J].
Li, DM ;
Shi, F ;
Peng, JJ ;
Guo, S ;
Deng, YQ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3582-3585
[12]  
Martyn E. J., 2002, Patent No. [WO 02/30865, 0230865]
[13]  
Olah G.A., 1989, NITRATION METHODS ME
[14]  
OLAH GA, 1978, J ORG CHEM, V43, P462
[15]   Zeolite-assisted nitration of neat toluene and chlorobenzene with a nitrogen dioxide/molecular oxygen system.: Remarkable enhancement of para-selectivity [J].
Peng, XH ;
Suzuki, H ;
Lu, CX .
TETRAHEDRON LETTERS, 2001, 42 (26) :4357-4359
[16]   Nitration of simple aromatics with NO2 under air atmosphere in the presence of novel Bronsted acidic ionic liquids [J].
Qi, Xiufang ;
Cheng, Guangbin ;
Lu, Chunxu ;
Qian, Desheng .
SYNTHETIC COMMUNICATIONS, 2008, 38 (04) :537-545
[17]   Nitration of aromatic compounds with nitric acid catalyzed by ionic liquids [J].
Qiao, K ;
Yokoyama, C .
CHEMISTRY LETTERS, 2004, 33 (07) :808-809
[18]   Vapor-phase nitration of benzene over solid acid catalysts (1):: Nitration with nitric oxide (NO2) [J].
Sato, H ;
Hirose, K .
APPLIED CATALYSIS A-GENERAL, 1998, 174 (1-2) :77-81
[19]  
Schofield K., 1980, AROMATIC NITRATION
[20]   Catalytic reactions in ionic liquids [J].
Sheldon, R .
CHEMICAL COMMUNICATIONS, 2001, (23) :2399-2407