Citation: BI Bo, KAI Wang, REN Liping, QIAN Hua. Thermoregulated Biphasic Acidic Polymeric Ionic Liquid Catalyzed Amine Aldehyde Condensation Reaction[J]. Chinese Journal of Applied Chemistry, ;2017, 34(4): 394-401. doi: 10.11944/j.issn.1000-0518.2017.04.160261 shu

Thermoregulated Biphasic Acidic Polymeric Ionic Liquid Catalyzed Amine Aldehyde Condensation Reaction

BI Bo ^a ,
KAI Wang ^a ,
REN Liping ^b ,
QIAN Hua ^a,c,*,,

a.
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
b.
China North Standardization Research Center, Beijing 100089, China
c.
National Supervision and Inspection Center for Industrial Explosive Materials, Nanjing 210094, China

Corresponding author: QIAN Hua, qianhua@njust.edu.cn
Received Date: 23 June 2016
Revised Date: 18 August 2016
Accepted Date: 21 September 2016

Fund Project: Supported by the National Natural Science Foundation of China No.21406116

Figures(5)

Acidic polymeric ionic liquid was synthesized with polyethylene glycol as the main chain and imidazole-based ionic liquid as crosslinking agent through the free radical polymerization to reduce the loss rate of catalyst. The thermoregulated biphasic system comprised of ionic liquid and toluene was used for the condensation reaction of aniline and benzaldehyde. The catalytic results show that the catalyst has advantages of high catalytic activity, small loss and easy recycling. The yield of N-benzalaniline is 93.4%, and the average loss rate of ionic liquid is about 2.5%. Further tests show that the system has good universality for the various substrates, and the yield of the products is 57.2%~82.9%.
- thermoregulated biphase,
- ionic liquid,
- polyethylene glycol,
- polymerization,
- catalysis
1. [1]
  JIN Zilin, LIU Ning, LIU Chun. Thermoregulated Liquid/Liquid Biphasic Catalysis[J]. Prog Chem, 2010,22(7):1295-1308.
2. [2]
  YANG Yuchuan, WEI Li, JIN Zilin. New Progress in Liquid/Liquid Biphasic Catalysis-Thermoregulated Non-aqueous Liquid/Liquid Biphasic Catalysis[J]. Chinese J Org Chem, 2004,24(6):579-584.
3. [3]
  Zhu J, Wang P C, Lu M. Synthesis of Novel Magnetic Silica Supported Hybrid Ionic Liquid Combining TEMPO and Polyoxometalate and Its Application for Selective Oxidation of Alcohols[J]. RSC Adv, 2012,2(2):8265-8268.
4. [4]
  Feng G L, Wang Y H, Jiang J Y. Using Thermoregulated PEG Biphasic System to Effect the Hydroformylation of p-Isobutylsrene Catalyzed by Rh/OPGPP Complex[J]. J Mol Catal A Chem, 2006,248(1):159-162.
5. [5]
  Wang Y H, Jiang J Y, Jin Z L. Thermoregulated Liquid/Liquid Biphasic Catalysis and Its Application[J]. Catal Surveys Asia, 2004,8(2):119-126. doi: 10.1023/B:CATS.0000027013.69419.31
6. [6]
  LIU Xiaobing, ZHONG Luping, HU Yulin. Study on Dehydration of Fructose Catalyzed by Ionic Liquid in Thermoregulated Biphasic System[J]. Guangdong Chem Ind, 2015,42(11):42-43. doi: 10.3969/j.issn.1007-1865.2015.11.018
7. [7]
  HU Yulin, LU Ming, FANG Dong. Study on the Synthesis of Tetrahydro-β-carboline Derivatives in PEG1000-DAIL/Toluene Temperature-dependent Biphasic System[J]. J Yancheng Inst Technol (Nat Sci Ed), 2013,26(3):14-19.
8. [8]
  Nguyen M D, Nguyen L V, Jeon E H. Fe-containing Ionic Liquids as Catalysts for the Dimerization of Bicyclo[2.2.1]hepta-2, 5-diene[J]. J Catal, 2008,258(1):5-13. doi: 10.1016/j.jcat.2008.05.008
9. [9]
  Bica K, Gaertner P. Metal-Containing Ionic Liquids as Efficient Catalysts for Hydroxymethylation in Water[J]. Eur J Org Chem, 2008,2008(20):3453-3456. doi: 10.1002/ejoc.v2008:20
10. [10]
  Huddleston J G, Rogers R D. Room Temperature Ionic Liquids as Novel Media for 'clean' Liquid liquid Extraction[J]. Chem Commun, 1998,16(16):1765-1766.
11. [11]
  HU Yulin. Study on the Unit Reactions of Organic Synthesis in Ionic Liquid Biphasic Systems[D]. Nanjing:Nanjing University of Science and Technology, 2012:33-53(in Chinese).
12. [12]
  ZHI Huizhen, LUO Jun, LV Chunxu. Esterification of Aromatic Acids and Alcohols in Acidic PEG Thermoregulated Ionic Liquids[J]. Chem J Chinese Univ, 2008,29(4):772-774.
13. [13]
  ZHI Huizhen, LUO Jun, LV Chunxu. Acetalization of Aromaldehyde and Ethyleneglycol in Novel PEG Thermoregulated Ionic Liquids[J]. Chem J Chinese Univ, 2008,29(10):2007-2010. doi: 10.3321/j.issn:0251-0790.2008.10.020
14. [14]
  ZHI Huizhen, WANG Yinglei, ZHANG Qiang. Reduction of Nitroarenes in PEG₁₀₀₀-DIL/Toluene Thermoregulated Biphasic System[J]. Chem J Chinese Univ, 2013,34(3):573-578. doi: 10.7503/cjcu20120791
15. [15]
  XING Tantan. Synthesis of a Shuangyang Ionic Ionic Liquid Alkaline with Thermoregulated Biphasic and Its Application in Organic Reaction[D]. Nanjing:Nanjing University Science Technology, 2011:33-43(in Chinese).
16. [16]
  Huddlelestn J G. Characterization and Comparison of Hydrophobic Room Temperature Ionic Liqids Incorporation the Imidazolium Cation[J]. Green Chem, 2001,3(4):156-164. doi: 10.1039/b103275p
17. [17]
  Davis J H. Novel Organic Ionic Liquids (OILS) Incorporating Cations Derived from the Antifungal Drug Miconazole[J]. Tetrahedron Lett, 1998,39(49):8955-8958. doi: 10.1016/S0040-4039(98)02070-X
18. [18]
  LI Long, MA Cha, YUAN Xubo. Synthesis and Application of Dendrimers in Oilfield Chemistry[J]. Mod Chem Ind, 2012,32(6):16-21.
19. [19]
  Floudas G, Papadopoulos P, Klok H A. Hierarchical Self-assembly of Poly (γ-benzyl-L-glutamate)-poly (ethylene glycol)-poly (γ-benzyl-L-glutamate) rod-coil-rod Triblock Copolymers[J]. Macromolecules, 2003,36(11):3673-3683.
20. [20]
  Gibson H W, Yamaguchi N, Jones J W. Supramolecular Pseudorotaxane Polymers From Complementary Pairs of Homoditopic Molecules[J]. J Am Chem Soc, 2003,125(12):3522-3533. doi: 10.1021/ja020900a
21. [21]
  Pourjzvzdi A. Multi-Layer Functionalized Poly (Ionic Liquid) Coated Magnetic Nanoparticles:Highly Recoverable and Magnetically Separable Brønsted Acid Catalyst[J]. ACS Catal, 2012,2(6):1259-1266. doi: 10.1021/cs300140j
22. [22]
  Yu F L, Wang Y Y, Liu C Y. Oxidative Desulfurization of Fuels Catalyzed by Ammonium Oxidative-thermoregulated Bifunctional Ionic Liquids[J]. Chem Eng J, 2014,255(7):372-376.
23. [23]
  Nakashima T, Kimizuka N. Inerfacial Synthesis of Hollow TiO₂ Microspheres in Ionic Liquids[J]. J Am Chem Soc, 2003,125(21):6386-6387. doi: 10.1021/ja034954b
24. [24]
  GAO Hongbin. Organic Chemistry[M]. 4th Ed. Beijing:Higher Edution Press, 2010:395-397(in Chinese).
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沈阳化工大学材料科学与工程学院沈阳 110142

Thermoregulated Biphasic Acidic Polymeric Ionic Liquid Catalyzed Amine Aldehyde Condensation Reaction

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

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通讯作者: 陈斌, bchen63@163.com