SIOC English
化学学报
高级检索

化学学报 >

2012 , Vol. 70 >Issue 06: 741 - 746

DOI: https://doi.org/10.6023/A1110105

研究论文

碱性离子液体的合成及其在Baylis-Hillman 反应中的应用

  • 易封萍 ,
  • 张旋 ,
  • 孙海洋 ,
  • 陈世洪
展开
  • a 上海应用技术学院香料香精技术与工程学院 上海 201418;
    b 江西环境工程职业学院环境工程系 赣州 341000

收稿日期: 2011-10-10

  修回日期: 2011-12-30

  网络出版日期: 2012-01-20

基金资助

上海市教委重点科研创新项目(No. 11ZZ180)和上海市科委地方院校能力建设项目(No. 11520502600)资助项目.

收起

Study on the Synthesis of Alkaline Ionic Liquids and Application for Baylis-Hillman Reaction

  • Yi Fengping ,
  • Zhang Xuan ,
  • Sun Haiyang ,
  • Chen Shihong
Expand
  • a School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 201418;
    b Department of Environmental Engineering, Jiangxi Environmental Engineering Vocational College, Ganzhou 341000

Received date: 2011-10-10

  Revised date: 2011-12-30

  Online published: 2012-01-20

Supported by

Project supported by the Key and Innovation Project of Shanghai Educational Committee (No. 11ZZ180) and the Project of Local University Ability Building of Shanghai Scientific and Technological Committee (No. 11520502600).

Fold

摘要

采用正交实验优化合成了碱性离子液体氢氧化1-丁基-4-二甲氨基吡啶盐, 以其为反应溶剂, 在催化剂DABCO(1,4-二氮杂二环[2.2.2]辛烷)作用下进行了芳香醛与丙烯酸甲酯的Baylis-Hillman 反应研究. 实验结果表明, 在该离子液体的存在下, 芳香醛与丙烯酸甲酯以较快的反应速度和较高产率生成目标化合物. 在此基础上, 进一步研究了水-离子液体复合体系对Baylis-Hillman 反应的影响, 取得了更快的速率及更高的产率.

关键词： 碱性离子液体; 芳香醛; 丙烯酸甲酯; Baylis-Hillman 反应; 水

本文引用格式

易封萍 , 张旋 , 孙海洋 , 陈世洪 . 碱性离子液体的合成及其在Baylis-Hillman 反应中的应用[J]. 化学学报, 2012 , 70(06) : 741 -746 . DOI: 10.6023/A1110105

Abstract

The synthetic methods of alkaline ionic liquid hydroxide 1-butyl-4-dimethy1 aminopyridine were optimized by using orthogonal experimental. By using triethylene diamine (DABCO) as catalyst and alkaline ionic liquid as solvent, aromatic aldehydes with methyl acrylate’s Baylis-Hillman reaction was studied. Experimental results showed that fast reaction rate and high yield were obtained in the presence of the alkaline ionic liquid. On this basis, Baylis-Hillman reaction under the influence of water-ionic liquid composite system was further studied, and obtained better result.

Key words： alkaline ionic liquids; aromatic aldehydes; methyl acrylate; Baylis-Hillman reaction; water

参考文献

1 Welton, T. Chem. Rev. 1999, 99, 2071.  

2 Samanta, A. J. Phys. Chem. 2006, 110, 13704.

3 Li, X. H.; Li, R.; Chen, X. W.; Wang, F. R.; Wang, L. F. Ind. Catal. 2007, 15(5), 1 (in Chinese). (李雪辉, 李榕, 陈学伟, 王芙蓉, 王乐夫, 工业催化,2007, 15(5), 1.)  

4 Liu, H. L.; Lv, L. Q.; Zhang, X. C. Chem. Engineer. 2010,38, 76 (in Chinese). (刘会茹, 吕力强, 张星辰, 化学工程, 2010, 38, 76.)

5 Hallett, J. P.; Welton, T. Chem. Rev. 2011, 111, 3508.  

6 Basavaiah, D.; Rao, K. V. Chem. Soc. Rev. 2007, 36, 1581.  

7 Rodrigo, O. M. A.; Pereira, V. L. P. Tetrahedron Lett. 2008,49, 5902.  

8 Yang, K. S.; Lee, W. D.; Chen, K. J. Org. Chem. 2003,68(3), 915.

9 Davy, R. J. A.; Christian, V. S. Org. Process Res. Dev.2006, 10, 417.  

10 Gary, E. K.; Dennie, S. W. Org. Lett. 2002, 4, 3687.  

11 Yu, C. Z.; Hu, L. Q. J. Org. Chem. 2002, 67, 219.  

12 Wang, R. D.; Li, J.; Li, C. J.; Liu, J.; Li, D. F.; Jia, X. S.; Zhai, H. B. Chin. J. Chem. 2010, 28, 1253

13 Zhao, S. H.; Zhao, M. G.; Zhang, H. R. Chin. J. Org. Chem.2007, 27, 322 (in Chinese). (赵三虎, 赵明根, 张海容, 有机化学, 2007, 27, 322.)

14 Poliakoff, M.; Michael, F.; Paul, T. A. Green Chem. 2002,297, 807.

15 Rose, P. M.; Clifford, A. A.; Rayner, C. M. Chem. Commun.2002, 968.

16 Zhao, S. H.; Chen, Z. B. J. Shanxi Univ. 2004, 27, 384 (in Chinese). (赵三虎, 陈兆斌, 山西大学学报, 2004, 27, 384.)

17 Kim, E. J.; Ko, S. Y. Helv. Chim. Acta 2003, 86, 894.  

18 Lin, Y. S.; Lin, C. Y., Liu, C. W.; Tsai, Y. R. Tetrahedron2006, 62, 872.  

19 Jur?ík, V.; Wilhelm, R. Green Chem. 2005, 7, 844.  

20 Gong, H.; Cai, C.; Yang, N.; Yang, L.; Zhang, J.; Fan, Q. J. Mol. Catal. A: Chem. 2006, 249, 236.  

21 Zhao, S.; Bie, H.; Chen, Z. Org. Prep. Proced. Int. 2005,37, 231.  

22 Hsu, J.; Yen, Y.; Chu, Y. Tetrahedron Lett. 2004, 45, 4673.  

23 Mi, X.; Luo, S.; Cheng, J. P. J. Org. Chem. 2005, 70, 2338.  

24 Mi, X.; Luo, S.; Xu, H.; Zhang, L.; Cheng, J. P. Tetrahedron2006, 62, 2537.  

25 Pégot, B.; Vo-Thanh, G.; Gori, D.; Loupy, A. Tetrahedron Lett. 2004, 45, 6425.  

26 Kumar, A.; Pawar, S. S. J. Mol. Catal. A: Chem. 2004, 211,43.  

27 Ryu, J. S.; Jeong, Y. K. J. Org. Chem. 2010, 75, 4183.  

28 Tang, C. C.; Zhou, Z. H.; Cai, J. X. Org. Lett. 2002, 4,4723.  

29 Hu, L. Q.; Yu, C. Z. J. Org. Chem. 2001, 66, 5413.  

30 Kupetis, G. K.; Šaduikis, G.; Nivinskiene, O.; Eicher-Lorka, O. Monatsh. Chem. 2002, 133, 313.  

31 Zhu, B.; Yan, L.; Pan, Y. H.; Lee, R.; Liu, H. J.; Han, Z. Q.; Huang, K. W.; Tan, C. H.; Jiang, Z. Y. J. Org. Chem. 2011,76, 6894.  

32 Han, X. Y.; Wang, Y. Q.; Zhong, F. R.; Lu, Y. X. Org. Biomol. Chem. 2011, 9, 6734.  

33 Coelho, F.; Almeida, W. P.; Veronese, D.; Mateus, C. R.; Lopes, E. C. S.; Rossi, R. C.; Silveira, G. P. C.; Pavam, C. H. Tetrahedron 2002, 58, 7437.  
Options
文章导航

/

〈 〉