Citation: Ma Hao, Zou Lianning, Mi Linhan, Pan Haiting, Liao Chunyan, Teng Junjiang. Knoevenagel Condensation Reaction at Room Temperature under Solvent-Free Conditions Catalyzed by Activated Carbon-Supported Chitosan[J]. Chemistry, ;2018, 81(7): 616-624. shu

Knoevenagel Condensation Reaction at Room Temperature under Solvent-Free Conditions Catalyzed by Activated Carbon-Supported Chitosan

Ma Hao ^1,2 ,
Zou Lianning ³ ,
Mi Linhan ¹ ,
Pan Haiting ¹ ,
Liao Chunyan ¹ ,
Teng Junjiang ^1,,

1.
College of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000
2.
Technology Research Center for Lingnan Characteristic Fruits & Vegetables Processing and Application Engineering of Guangdong Province, Food Science Innovation Team of Guangdong Higher Education Institutes, Maoming 525000
3.
Maoming Customs, Maoming 525000

Corresponding author: Teng Junjiang, tjjteng@gdupt.edu.cn
Received Date: 4 January 2018
Accepted Date: 28 April 2018

Figures(5)

The activated carbon (AC) supported chitosan (CS) catalyst, denoted as CS/AC, was prepared by a simple method. The physicochemical properties of the as-prepared catalyst were characterized by FT-IR, XRD, TG-DTG, SEM, BET, and elemental analysis. The catalytic performance was tested by the Knoevenagel condensation reaction, and the results showed that the catalyst can efficiently catalyze the Knoevenagel condensation reaction of a series of aromatic aldehydes with active methylene compounds at solvent-free and room temperature conditions, affording more than 80% products yield. Furthermore, when the reaction system is scaled up by 100 times, the catalyst still maintains high catalytic efficiency. Moreover, the catalyst can be recovered by simple filtration and reused at least 8 times without significant loss of activity, indicating that the catalyst is very stable.
- Activated carbon,
- Chitosan,
- Knoevenagel condensation reaction,
- Room temperature,
- Solvent-free
1. [1]
  L G Voskressensky, A A Festa, A V Varlamov. Tetrahedron, 2014, 70(3):551-572.
2. [2]
  I M McDonald. Knoevenagel Reaction. John Wiley & Sons, 2009.
3. [3]
  N Mase, T Horibe. Org. Lett., 2013, 44(33):1854-1857.
4. [4]
5. [5]
  B List. Angew. Chem. Int. Ed., 2010, 49(10):1730-1734.
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
  C I Ezugwu, B Mousavi, M A Asraf et al. J. Catal., 2016, 344:445-454.
12. [12]
13. [13]
  H Koga, T Kitaoka, A Isogai. J. Mater. Chem., 2011, 21(25):9356-9361.
14. [14]
15. [15]
16. [16]
  M N Kumar, R A Muzzarelli, C Muzzarelli et al. Chem. Rev., 2004, 104(12):6017-6084.
17. [17]
  V Froidevaux, C Negrell, S Caillol et al. Chem. Rev., 2016, 116(22), 14181-14224.
18. [18]
  A E Kadib. ChemSusChem, 2015, 8(2):217-244.
19. [19]
  O Mahé, J F Brière, I Dez. Eur. J. Org. Chem., 2015, 2015(12):2559-2578
20. [20]
  M G Dekamin, M Azimoshan, L Ramezani. Green Chem., 2013, 15(3), 811-820.
21. [21]
  S N Rao, D C Mohan, S Adimurthy. Green Chem., 2014, 16(9):4122-4126.
22. [22]
  K R Reddy, K Rajgopal, C U Maheswari et al. New J. Chem., 2006, 30(11):1549-1552.
23. [23]
  H Kayser, C R Müller, C A García-González et al. Appl. Catal. A, 2012, s445-446(6):180-186.
24. [24]
  A Ricci, L Bernardi, C Gioia et al. Chem. Commun., 2010, 46(34):6288-6290.
25. [25]
  H Dong, J Liu, L Ma et al. Catalysts, 2016, 6(12):186.
26. [26]
  J Safari, L Javadian. RSC Adv., 2014, 4(90):48973-48979.
27. [27]
  Y Luo, X Pan, Y Ling et al. Cellulose, 2014, 21(3):1873-1883.
28. [28]
  G Chen, J Mi, X Wu et al. Int. J. Biol. Macromol., 2011, 49(4):543-547.
29. [29]
  R Valentin, B Bonelli, E Garrone et al. Biomacromolecules, 2007, 8(11):3646-3650.
30. [30]
  C Paluszkiewicz, E Stodolak, M Hasik et al. Spectrochim. Acta A, 2011, 79(4):784-788
31. [31]
  F Min, Q Hu, S Kai. Carbohyd. Polym., 2009, 78(1):66-71.
32. [32]
  K Ogawa, S Hirano, T Miyanishi et al. Macromolecules, 1984, 17(4):973-975.
33. [33]
  T Yui, K Imada, K Okuyama, et al. Carbohyd. Res., 1992, 229(1):57-74.
34. [34]
  P Z Hong, S D Li, C Y Ou et al. J. Appl. Polym. Sci., 2010, 105(2):547-551.
35. [35]
  M L Deb, P J Bhuyan. Tetrahed. Lett., 2005, 46(38):6453-6456.
36. [36]
37. [37]
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沈阳化工大学材料科学与工程学院沈阳 110142