Chinese Journal of Organic Chemistry >
Synthesis of Novel Benzothiazolium Ionic Liquids and Research on Their Catalytic Esterification for Ricinoleic Acid
Received date: 2015-11-12
Revised date: 2015-12-21
Online published: 2016-01-15
Supported by
Project supported by the 948 Project Foundation of State Forestry Administration (No. 2015-4-55).
Four new task-specfic benzothiazolium ionic liquids (ILs) [HBth]HSO4, [HBth]H2PO4, [HBth]ClO4, [HBth]NO3 were synthesized and characterized by NMR and FT-IR, which bear the proton acid groups based on low price benzothiazole as raw material. The catalytic activities of these acidic ionic liquids were investigated by the esterification of ricinoleic acid with ethanol ethylene glycol monobutyl ether (EGBE) and were compared with concentrated sulfuric acid. The results showed that under the optimized conditions: n(Ricinoleic acid):n(EGBE)=1:1.15, catalyst dosage 2% (wt) of ricinoleic acid, reaction temperature 90 ℃ and reaction time 5 h, esterification yield was up to 98.8%. The ionic liquids dried in vacuum till remained high activity after reused for 10 times. Finally, the yields of series of ricinoleic acid binary alcohol ether ester and short-chain fatty acids ester were also high with [HBth]HSO4 as catalyst, and the ionic liquids can form split-phases with ester product. Compared with the traditional sulfuric acid catalytic esterification, catalytic esterification of such ionic liquid has the advantages of low production cost, clean process, low corrosion rate, reusable, and has the potential of replacing the traditional sulfuric acid in catalytic esterification reaction of ricinoleic acid.
Key words： benzothiazolium; ionic liquids; ricinoleic acid; esterification; catalytic activity
Zhang Haifei , Liu Dongmei , Kang Tingting , Wang Ye , Zhang Xiaoxiang , Zhu Xinbao . Synthesis of Novel Benzothiazolium Ionic Liquids and Research on Their Catalytic Esterification for Ricinoleic Acid[J]. Chinese Journal of Organic Chemistry, 2016 , 36(5) : 1104 -1110 . DOI: 10.6023/cjoc201511019
[1] Zeng, Q.-F.; Dong, G.-N. Tribol. Lett. 2013, 52, 47.
[2] Tong, L.-G.; Rong, H.; Lin, S.-J. J. Beijing Inst. Petro-Chem. Technol. 2010, 18, 58 (in Chinese).
(佟拉嘎, 荣华, 林世静, 北京石油化工学院学报, 2010, 18, 58.)
[3] Doudin, K.; A-Malaika, S.; Dole, H. Polym. Degrad. Stab. 2011, 96, 438.
[4] Dias, J.-M.; Araujo, J.-M.; Costa, J.-F. Energy2013, 53, 58.
[5] Amador, P.; Martinez, E.; Sanchez-Daza, O. J. Chem. Thermodyn. 2012, 50, 15.
[6] Wu, J. Agric. Mach. 2011, 61, 61 (in Chinese).
(吴杰, 农业机械, 2011, 61, 61.)
[7] Zhao, D.-B.; Fei, Z.-F.; Geldbach, T.-J.; Scopelliti, R.; Laurenczy, G.; Dyson, P.-J. J. Am. Chem. Soc. 2005, 88, 665.
[8] Inui, K.; Kurabayashi, T.; Sato, S.; Ichikawa, N. J. Mol. Catal A: Chem. 2004, 216, 147.
[9] Amador, P.; Martinez E, Sanchez-Daza O. J. Chem. Thermodyn.2012, 50, 15.
[10] Li, Y.; Hu, S.-L.; Cheng, J.-H.; Lou, W.-Y. Chin. J. Catal. 2014, 35, 396.
[11] Zhao, D.-S.; Liu, M.-S.; Ge, J.-J.; Zhang, J.; Ren, P.-B. Chin. J. Org. Chem. 2012, 32, 2382 (in Chinese).
(赵地顺, 刘猛帅, 葛京京, 张娟, 任培兵, 有机化学, 2012, 32, 2382.)
[12] Hou, H. L.; Li, Z. F.; Ying, A. G. Chin. J. Org. Chem. 2014, 34, 1277 (in Chinese).
(侯海亮, 李志峰, 应安国, 许松林, 有机化学, 2014, 34, 1277.)
[13] Peter, W.; Wilhelm, K. Angew. Chem., Int. Ed. 2000, 39, 3772.
[14] Plechkova, N.-V.; Seddon, K.-R. Chem. Soc. Rev. 2008, 370, 123.
[15] Tokuda, H.; Tsuzuki, S.; Susan, M. A.-B. H.; Hayamizu, K.; Watanabe, M. J. Chin. Phys. Chem. B 2006, 110, 19593.
[16] Song, Y.-L.; Wang, X.-C.; Huang, C.-P.; Liang, F.-B.; Liu, Z.-C.; Chen, B.-H. Chin. J. Org. Chem. 2013, 33, 1715.
[17] Jankovic, M. R.; Sinadinovic-Fiser, S. V.; Govedarica, O.-M. Ind. Eng. Chem. Res.2014, 53, 9357.
[18] Elsheikh, Y.-A. Energy Convers. Manage.2011, 52, 804.
[19] Liu, S.-W.; Li, L.; Yu, S.-T. Chin. J. Catal. 2010, 31, 1433.
[20] Earle, M.-J.; Seddon, K.-R. Pure Appl. Chem. 2000, 72: 1391-1398.
[21] Marsh, K.-N; Boxall, J.-A.; Lichtenthaler, R. Fluid Phase Equilib.2004, 219: 93~98.
[22] Wu, K.; Li, C.-X. Chin. J. Org. Chem. 2011, 31, 119 (in Chinese).
(吴坤, 李存雄, 有机化学, 2011, 31, 119.)
[23] Li, J.-Y.; Peng, J.-J.; Qiu, H.-Y.; Jiang, J.-X.; Wu, J.-R.; Ni, Y.; Lai, G.-Q. Chin. J. Org. Chem. 2007, 27, 483 (in Chinese).
(厉嘉云, 彭家建, 邱化玉, 蒋剑雄, 邬继荣, 倪勇, 来国桥, 有机化学, 2007, 27, 483.)
[24] Wang, Y.-Y.; Wu, Y.-T.; Liu, K.; Dai, L.-Y. Chin. Chem. Lett. 2012, 23, 1031.
[25] Venkataraman, V-R; Ali, K.-S. Indian J. Heterocycl. Chem. 2001, 11, 93.
[26] Zhao, D. S.; Liu, M. S.; Xu, Z. C.; F, J. T.; Ren, P. B. Chem. Ind. Eng. Prog. 2011, 30, 2287 (in Chinese).
(赵地顺, 刘猛帅, 徐智策, 付江涛, 任培兵, 化工进展, 2011, 30, 2287.)
[27] Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
[28] Huddleston, J. G.; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green. Chem. 2001, 3, 156.
[29] Fredakle, C.-P.; Crosthwaite, J.-M.; Hert, D.-G. J. Chem. Eng. Data 2004, 49, 954.
[30] Yang, L.; Lu, J.; Bai, Y. J. Chin.. J. Org. Chem. 2003, 23, 659 (in Chinese).
(杨玲, 路军, 白银娟, 有机化学, 2003, 23, 659.)
[31] Anthony, J. L.; Maginn, E. J.; Brennecke, J.-F. J. Phys. Chem. B2001, 105, 10942.
[32] Ji, S. X.; Zhao, Y. J.; He, C. Petrochem. Technol. 2010, 39, 251 (in Chinese).
(纪世雄, 赵义军, 何春, 石油化工, 2010, 39, 251.)
[33] Wang, Q.; Ma, R. X. J. Langzhou Univ. Technol. 2005, 31, 57 (in Chinese).
(王俏, 马荣萱, 兰州理工大学学报, 2005, 31, 57.)
[34] Zeng, H. Y.; Ying, S. F.; Li, Y. Chin. J. Org. Chem. 2007, 27, 528 (in Chinese).
(曾鸿耀, 尹述凡, 李颖, 有机化学, 2007, 27, 528.)
[35] Peng, Q.; Zhang, Y. W.; Wang, X. M. Chin. J. Synth. Chem. 2012, 20, 28 (in Chinese).
(彭琦, 张义文, 王小敏, 王卓端, 姚舜, 宋航, 合成化学, 2012, 20, 28.)
[36] Huang, B.-H.; Li, Z.-J.; Shi, N.; Xu, X.-L.; Fang, Y.-X. Chin. J. Org. Chem. 2009, 29, 770 (in Chinese).
(黄宝华, 黎子进, 史娜, 徐效陵, 张焜, 方岩雄, 有机化学, 2009, 29, 770.)
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