Hydrolysis of cyclohexyl acetate to cyclohexanol with high selectivity over SO3H-functionalized ionic liquids

被引:8
作者
Yang, Fang [1 ]
Xue, Wei [1 ]
Zhang, Dongsheng [1 ]
Li, Fang [1 ]
Wang, Yanji [1 ]
机构
[1] Hebei Univ Technol, Sch Chem Engn & Technol, Hebei Prov Key Lab Green Chem Technol & High Effi, 8 Guangrongdao St, Tianjin 300130, Peoples R China
基金
中国国家自然科学基金;
关键词
Cyclohexanol; Cyclohexyl acetate; Hydrolysis; Pyrolysis; SO3H-functionalized ionic liquids; ACID; CATALYSTS; HYDRATION; EFFICIENT; BENZENE;
D O I
10.1007/s11144-015-0909-1
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
The catalytic performance of acidic ionic liquids (ILs) was evaluated for the hydrolysis of cyclohexyl acetate to cyclohexanol. Cyclohexyl acetate conversion increased with increasing acid strength of the ILs, but the five SO3H-functionalized ILs with different acidity had similarly high activity. All of the ILs exhibited high selectivity to cyclohexanol. This can be attributed to the high polarity of the ILs, which inhibits the formation of the transition state for the side reaction, pyrolysis of cyclohexyl acetate to cyclohexene, and then increases cyclohexanol selectivity. Under optimized conditions, cyclohexyl acetate conversion was 80.2 with 96.6 % cyclohexanol selectivity over [HSO(3)bmim]HSO4 (bmim = butyl-3-methyl-imidazolium). Moreover, [HSO(3)bmim]HSO4 also showed high reusability.
引用
收藏
页码:329 / 339
页数:11
相关论文
共 23 条
[1]   CYCLOHEXANOL FROM CYCLOHEXENE VIA CYCLOHEXYL ACETATE - CATALYSIS BY ION-EXCHANGE RESIN AND ACID-TREATED CLAY [J].
CHAKRABARTI, A ;
SHARMA, MM .
REACTIVE POLYMERS, 1992, 18 (02) :107-115
[2]   Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts [J].
Cole, AC ;
Jensen, JL ;
Ntai, I ;
Tran, KLT ;
Weaver, KJ ;
Forbes, DC ;
Davis, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5962-5963
[3]  
Dong C., 2013, CIESC J, V64, P2086
[4]  
Du W, 2012, J HEBEI U TECHNOL, V41, P34
[5]   SO3H-functionalized ionic liquid as efficient, green and reusable acidic catalyst system for oligomerization of olefins [J].
Gu, YL ;
Shi, F ;
Deng, YQ .
CATALYSIS COMMUNICATIONS, 2003, 4 (11) :597-601
[6]   A carbon material as a strong protonic acid [J].
Hara, M ;
Yoshida, T ;
Takagaki, A ;
Takata, T ;
Kondo, JN ;
Hayashi, S ;
Domen, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (22) :2955-2958
[7]   Evaluation of Different Process Concepts for the Indirect Hydration of Cyclohexene to Cyclohexanol [J].
Imam, Rayees Ahamed ;
Freund, Hannsjoerg ;
Guit, Rudolf P. M. ;
Fellay, Celine ;
Meier, Robert J. ;
Sundmacher, Kai .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2013, 17 (03) :343-358
[8]  
Ishida H., 1997, CATAL SURV JPN, V1, P241, DOI DOI 10.1023/A:1019037316000
[9]  
[靳敬敬 Jin Jingjing], 2014, [石油学报. 石油加工, Acta Petrolei Sinica. Petroleum Processing Section], V30, P169
[10]   Two-Step Reactive Distillation Process for Cyclohexanol Production from Cyclohexene [J].
Katariya, Amit ;
Freund, Hannsjoerg ;
Sundmacher, Kai .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2009, 48 (21) :9534-9545