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]
1. [1]
  Dong-Bing Cheng , Junxin Duan , Haiyu Gao . Experimental Teaching Design on Chitosan Extraction and Preparation of Antibacterial Gel. University Chemistry, 2024, 39(2): 330-339. doi: 10.3866/PKU.DXHX202308053
2. [2]
  Hui Zhang , Zijian Zhao , Yajing Wang , Kai Ni , Yanfei Wang , Liang Zhu , Jianyun Liu , Xiaoyu Zhao . Structurally engineered solvent-free LiFePO₄ electrodes via hot-pressing with efficient ion transport pathways for lithium extraction from brine. Acta Physico-Chimica Sinica, 2026, 42(2): 100130-0. doi: 10.1016/j.actphy.2025.100130
3. [3]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . Preparation of High Density Activated Carbon by Mechanical Compression of Precursors for Compact Capacitive Energy Storage. Acta Physico-Chimica Sinica, 2025, 41(3): 100028-0. doi: 10.3866/PKU.WHXB202406009
4. [4]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
5. [5]
  Jing Zhang , Su Zhang , Qiqi Li , Linken Ji , Yutong Li , Yukang Ren , Xiaobei Zang , Ning Cao , Han Hu , Peng Liang , Zhuangjun Fan . Integrating high surface area and electric conductivity in activated carbon by in situ formation of the less-defective carbon network during selective chemical etching. Acta Physico-Chimica Sinica, 2025, 41(10): 100114-0. doi: 10.1016/j.actphy.2025.100114
6. [6]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
7. [7]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
8. [8]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
9. [9]
  Guanghui SUI , Yanyan CHENG . Application of rice husk-based activated carbon-loaded MgO composite for symmetric supercapacitors. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 521-530. doi: 10.11862/CJIC.20240221
10. [10]
  Qing Xue , Shengyi Li , Yanan Zhao , Peng Sheng , Li Xu , Zhengxi Li , Bo Zhang , Hui Li , Bo Wang , Libin Yang , Yuliang Cao , Zhongxue Chen . Novel Alkaline Sodium-Ion Battery Capacitor Based on Active Carbon||Na_0.44MnO₂ towards Low Cost, High-Rate Capability and Long-Term Lifespan. Acta Physico-Chimica Sinica, 2024, 40(2): 2303041-0. doi: 10.3866/PKU.WHXB202303041
11. [11]
  Jiahong WANG , Zekun XU , Tianjiao LU , Jinming HUANG . Performance of N, Mn doped semi-coke activated carbon catalyzed ozone oxidation for the degradation of tetracycline hydrochloride in water. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2549-2560. doi: 10.11862/CJIC.20250120
12. [12]
  Wenli FENG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress on ultralong room temperature phosphorescent carbon dots. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 833-846. doi: 10.11862/CJIC.20240308
13. [13]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
14. [14]
  Yuecheng ZHANG , Fan YANG , Shiyu ZHANG , Chengjun MA , Rui TIAN , Xuehua SUN , Haoyu LI , Lingbo SUN , Hongyan MA . B-doped carbon quantum dots with long-afterglow room-temperature phosphorescence: Applications in information encryption and humidity sensing. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1361-1370. doi: 10.11862/CJIC.20240415
15. [15]
  Chunyuan Kang , Xiaoyu Li , Fan Yang , Bai Yang . Ionic-bond crosslinked carbonized polymer dots for tunable and enhanced room temperature phosphorescence. Acta Physico-Chimica Sinica, 2026, 42(1): 100156-0. doi: 10.1016/j.actphy.2025.100156
16. [16]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
17. [17]
  Xiaohang JIN , Qi LIU , Jianping LANG . Room‑temperature solid‑state synthesis, structure, and third‑order nonlinear optical properties of phosphine‑ligand‑protected silver thiolate clusters. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1505-1512. doi: 10.11862/CJIC.20250125
18. [18]
  Guanghui Wang , Chen Qian , Zhiyong Ma . Preparation and Characterization of 7H-Benzo[C]Carbazole Based Ultra-Long Organic Room Temperature Phosphorescence Material. University Chemistry, 2025, 40(11): 289-299. doi: 10.12461/PKU.DXHX202412062
19. [19]
  Shiqian WEI , Xinyu TIAN , Hong LIU , Maoxia CHEN , Fan TANG , Qiang FAN , Weifeng FAN , Yu HU . Oxygen reduction reaction/oxygen evolution reaction catalytic performances of different active sites on nitrogen-doped graphene loaded with iron single atoms. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1776-1788. doi: 10.11862/CJIC.20250102
20. [20]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(1967)
HTML views(420)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142