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Received December 11, 2013
Accepted March 4, 2014
- This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
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Tetrabutylphosphonium amino acid ionic liquids as efficient catalysts for solvent-free Knoevenagel condensation reactions
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
djtao@jxnu.edu.cn
Korean Journal of Chemical Engineering, August 2014, 31(8), 1377-1383(7), 10.1007/s11814-014-0077-4
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Abstract
Five tetrabutylphosphonium amino acid ionic liquids ([P4444][AA]) were prepared, characterized, and used as catalysts for solvent-free Knoevenagel condensation reactions. The tetrabutylphosphonium prolinate ([P4444][Pro]) showed excellent catalytic activity and selectivity in Knoevenagel condensation reactions of active methylene compounds with various aromatic aldehydes, and all the yields of corresponding products were more than 85% under mild_x000D_
conditions. Furthermore, a plausible reaction mechanism for the excellent performance of [P4444][Pro] has been proposed, and [P4444][Pro] could be used repetitively at least six times without obvious decrease in activity and quantity.
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References
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Parvin MN, Jin H, Ansari MB, Oh SM, Park SE, Appl. Catal. A: Gen., 413-414, 205 (2012)
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Benzagouta MS, AlNashef IM, Karnanda W, Al-Khidir K, Korean J. Chem. Eng., 30(11), 2108 (2013)
Fazlali A, Koranian P, Beigzadeh R, Rahimi M, Korean J. Chem. Eng., 30(9), 1681 (2013)
Mai NL, Kim SH, Ha SH, Shin HS, Koo YM, Korean J. Chem. Eng., 30(9), 1804 (2013)
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Yuan XH, Chen M, Dai QX, Cheng XN, Chem. Eng. J., 146(2), 266 (2009)
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Wei Z, Li F, Xing H, Deng S, Ren Q, Korean J. Chem. Eng., 26(3), 666 (2009)
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Xu J, Shen K, Xue B, Li YX, J. Mol. Catal. A-Chem., 372, 105 (2013)
Chen XQ, Arruebo M, Yeung KL, Catal. Today, 204, 140 (2013)
Mangala K, Sreekumar K, Appl. Organomet. Chem., 27, 73 (2013)
Wang H, Li L, Bai XF, Deng WF, Zheng ZJ, Yang KF, Xu LW, Green Chem., 15, 2349 (2013)
Zhao SH, Wang XJ, Zhang LW, RSC Adv., 3, 11691 (2013)
Burgoyne AR, Meijboom R, Catal. Lett., 143(6), 563 (2013)
Ansari MB, Jin HL, Parvin MN, Park SE, Catal. Today, 185, 2119 (2012)