Citation: Juanjuan Chen, Chang Wang, Bin Dong, Wenguang Leng, Jun Huang, Rile Ge, Yanan Gao. Ionic liquids as eco-friendly catalysts for converting glycerol and urea into high value-added glycerol carbonate[J]. Chinese Journal of Catalysis, ;2015, 36(3): 336-343. doi: 10.1016/S1872-2067(14)60257-6 shu

Ionic liquids as eco-friendly catalysts for converting glycerol and urea into high value-added glycerol carbonate

Juanjuan Chen ^a ,
Chang Wang ^b ,
Bin Dong ^b ,
Wenguang Leng ^b ,
Jun Huang ^a ,
Rile Ge ^b ,
Yanan Gao ^b,,

1.
a College of Chemistry and Chemical Engineering, Nanjing Tech University, Nanjing 210009, Jiangsu, China;

Corresponding author: Yanan Gao,
Received Date: 16 October 2014
Available Online: 19 November 2014
Fund Project: 国家自然科学基金(21273235, 21303076) (21273235, 21303076)

Acidic, basic and neutral ionic liquids (ILs) have been used as catalysts in the carbonylation of glycerol with urea. The results show that neutral ILs have high catalytic activity in the reaction. The excellent performance of the catalysts can be attributed to the synergistic effect of the cation and anion. We speculated that the cation with positive charge activates urea, and the anion with negative charge activates glycerol. In addition, the well balanced acid-basic properties of the catalysts are necessary for good catalytic performance. The ILs can be reused at least five times without loss of activity. Using ILs, instead of the traditional metal catalysts, reduces the use of non-renewable resources. It is eco-friendly that two inexpensive and bio-based raw materials were used and the catalytic reaction was carried out without solvent.
- Glycerol carbonate,
- Glycerol,
- Urea,
- Ionic liquid
1. [1]
  [1] Ma F R, Hanna M A. Bioresour Technol, 1999, 70: 1
2. [2]
  [2] Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F. Green Chem, 2008, 10: 13
3. [3]
  [3] Zhou C H, Beltramini J N, Fan Y X, Lu G Q. Chem Soc Rev, 2008, 37: 527
4. [4]
  [4] Sonnati M O, Amigoni S, de Givenchy E P T, Darmanin T, Choulet O, Guittard F. Green Chem, 2013, 15: 283
5. [5]
  [5] Hu J L, Li J J, Gu Y L, Guan Z H, Mo W L, Ni Y M, Li T, Li G X. Appl Catal A, 2010, 386: 188
6. [6]
  [6] Lim Y N, Lee C, Jang H Y. Eur J Org Chem, 2014: 1823
7. [7]
  [7] Strain F. US Patent 2 446 145. 1948
8. [8]
  [8] Patel Y, George J, Pillai S M, Munshi P. Green Chem, 2009, 11: 1056
9. [9]
  [9] Kim S C, Kim Y H, Lee H, Yoon D Y, Song B K. J Mol Catal B,2007, 49: 75
10. [10]
  [10] Climent M J, Corma A, Frutos P D, Iborra S, Noy M, Velty A, Concepción P. J Catal, 2010, 269: 140
11. [11]
  [11] Wang L G, Ma Y B, Wang Y, Liu S M, Deng Y Q. Catal Commun, 2011, 12: 1458
12. [12]
  [12] Turney T W, Patti A, Gates W, Shaheen U, Kulasegaram S. Green Chem, 2013, 15: 1925
13. [13]
  [13] Rahim M H A, He Q, Lopez-Sanchez J A, Hammond C, Dimitratos N, Sankar M, Carley A F, Kiely C J, Knight D W, Hutchings G J. Catal Sci Technol, 2012, 2: 1914
14. [14]
  [14] Jagadeeswaraiah K, Kumar C R, Prasad P S S, Loridant S, Lingaiah N. Appl Catal A,2014, 469: 165
15. [15]
  [15] Fujita S I, Yamanishi Y, Arai M. J Catal, 2013, 297: 137
16. [16]
  [16] Sandesh S, Shanbhag G V, Halgeri A B. RSC Adv, 2014, 4: 974
17. [17]
  [17] Claude S, Mouloungui Z, Yoo J W, Gaset A. US Patent 6 025 504. 2000
18. [18]
  [18] Lee M S, Baek J H. US Patent 2 013 026 771 5A1. 2013
19. [19]
  [19] Buzzeo M C, Evans R G, Compton R G. ChemPhysChem, 2004, 5: 1106
20. [20]
  [20] Macfarlane D R, Forsyth M, Howlett P C, Pringle J M, Sun J, Annat G, Neil W, Izgorodina E I. Acc Chem Res, 2007, 40: 1165
21. [21]
  [21] Liu H T, Liu Y, Li J H. Phys Chem Chem Phys, 2010, 12: 1685
22. [22]
  [22] Mulik A, Chandam D, Patil P, Patil D, Jagdale S, Deshmukh M. J Mol Liq, 2013, 179: 104
23. [23]
  [23] Welton T. Chem Rev, 1999, 99: 2071
24. [24]
  [24] Cole A C, Jensen J L, Ntai I, Tran K L T, Weaver K J, Forbes D C, Davis J H. J Am Chem Soc, 2002, 124: 5962
25. [25]
  [25] Forbes D C, Weaver K J. J Mol Catal A, 2004, 214: 129
26. [26]
  [26] Gu Y L, Shi F, Deng Y Q. Catal Commun, 2003, 4: 597
27. [27]
  [27] Nockemann P, Thijs B, Parac-Vogt T N, Van Hecke K, Van Meervelt L, Tinant B, Hartenbach I, Schleid T, Ngan V T, Nguyen M T, Binnemans K. Inorg Chem, 2008, 47: 9987
28. [28]
  [28] Bates E D, Mayton R D, Ntai I, Davis J H. J Am Chem Soc, 2002, 124: 926
29. [29]
  [29] Sarkar A, Roy S R, Parikh N, Chakraborti A K. J Org Chem, 2011, 76: 7132
30. [30]
  [30] Sarkar A, Roy S R, Chakraborti A K. Chem Commun, 2011, 47: 4538
31. [31]
  [31] Park D W, Mun N Y, Kim K H, Kim I, Park S W. Catal Today, 2006, 115: 130
32. [32]
  [32] Tharun J, Kathalikkattil A C, Roshan R, Kang D H, Woo H C, Park D W. Catal Commun, 2014, 54: 31
33. [33]
  [33] Ju H Y, Manju M D, Kim K H, Park S W, Park D W. J Ind Eng Chem, 2008, 14: 157
34. [34]
  [34] Kim D W, Roshan R, Tharun J, Cherian A, Park D W. Korean J Chem Eng, 2013, 30: 1973
35. [35]
  [35] Kim M I, Choi S J, Kim D W, Park D W. J Ind Eng Chem, 2014, 20: 3102
36. [36]
  [36] Kim D W, Kim C W, Koh J C, Park D W. J Ind Eng Chem, 2010, 16: 474
37. [37]
  [37] Saravanamurugan S, Riisager A. Catal Today, 2013, 200: 94
38. [38]
  [38] Fukumoto K, Yoshizawa M, Ohno H. J Am Chem Soc, 2005, 127: 2398
39. [39]
  [39] Wang C, Liu X M, Yang M, Ma H Y, Yan P F, Slattery J M, Gao Y A. RSC Adv, 2013, 3: 8796
40. [40]
  [40] Wang C, Liu J, Leng W G, Gao Y A. Int J Mol Sci, 2014, 15: 1284
41. [41]
  [41] Singh A, Kumar A. J Org Chem, 2012, 77: 8775
42. [42]
  [42] Zhang S G, Qi X J, Ma X Y, Lu L J, Deng Y Q. J Phys Chem B, 2010, 114: 3912
43. [43]
  [43] Matsumoto K, Hagiwara R, Yoshida R, Ito Y, Mazej Z, Benkič P, Žemva B, Tamada O, Yoshino H, Matsubara S. Dalton Trans, 2004: 144
44. [44]
  [44] Srour H, Rouault H, Santini C C, Chauvin Y. Green Chem, 2013, 15: 1341
45. [45]
  [45] Cull S G, Holbrey J D, Vargas-Mora V, Seddon K R, Lye G J. Biotechnol Bioeng, 2000, 69: 227
46. [46]
  [46] Schaber P M, Colson J, Higgins S, Thielen D, Anspach B, Brauer J. Thermochim Acta, 2004, 424: 131
47. [47]
  [47] Li Q B, Zhang W Y, Zhao N, Wei W, Sun Y H. Catal Today, 2006, 115: 111
48. [48]
  [48] Cláudio A F M, Swift L, Hallett J P, Welton T, Coutinho J A P, Freire M G. Phys Chem Chem Phys, 2014, 16: 6593
49. [49]
  [49] Roy S R, Chakraborti A K. Org Lett, 2010, 12: 3866
50. [50]
  [50] Chakraborti A K, Roy S R. J Am Chem Soc, 2009, 131: 6902
51. [51]
  [51] Chakraborti A K, Roy S R, Kumar D, Chopra P. Green Chem, 2008, 10: 1111
52. [52]
  [52] Lungwitz R, Strehmel V, Spange S. New J Chem, 2010, 34: 1135
1. [1]
  Yameen Ahmed , Xiangxiang Feng , Yuanji Gao , Yang Ding , Caoyu Long , Mustafa Haider , Hengyue Li , Zhuan Li , Shicheng Huang , Makhsud I. Saidaminov , Junliang Yang . Interface Modification by Ionic Liquid for Efficient and Stable FAPbI₃ Perovskite Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(6): 2303057-0. doi: 10.3866/PKU.WHXB202303057
2. [2]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
3. [3]
  Pei Li , Yuenan Zheng , Zhankai Liu , An-Hui Lu . Boron-Containing MFI Zeolite: Microstructure Control and Its Performance of Propane Oxidative Dehydrogenation. Acta Physico-Chimica Sinica, 2025, 41(4): 2406012-0. doi: 10.3866/PKU.WHXB202406012
4. [4]
  Ye Wang , Ruixiang Ge , Xiang Liu , Jing Li , Haohong Duan . An Anion Leaching Strategy towards Metal Oxyhydroxides Synthesis for Electrocatalytic Oxidation of Glycerol. Acta Physico-Chimica Sinica, 2024, 40(7): 2307019-0. doi: 10.3866/PKU.WHXB202307019
5. [5]
  Xin Feng , Kexin Guo , Chunguang Jia , Bowen Liu , Suqin Ci , Junxiang Chen , Zhenhai Wen . Hydrogen Generation Coupling with High-Selectivity Electrocatalytic Glycerol Valorization into Formate in an Acid-Alkali Dual-Electrolyte Flow Electrolyzer. Acta Physico-Chimica Sinica, 2024, 40(5): 2303050-0. doi: 10.3866/PKU.WHXB202303050
6. [6]
  Wenjuan Tan , Yong Ye , Xiujuan Sun , Bei Liu , Jiajia Zhou , Hailong Liao , Xiulin Wu , Rui Ding , Enhui Liu , Ping Gao . Building P-Poor Ni₂P and P-Rich CoP₃ Heterojunction Structure with Cation Vacancy for Enhanced Electrocatalytic Hydrazine and Urea Oxidation. Acta Physico-Chimica Sinica, 2024, 40(6): 2306054-0. doi: 10.3866/PKU.WHXB202306054
7. [7]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
8. [8]
  Yu Peng , Jiawei Chen , Yue Yin , Yongjie Cao , Mochou Liao , Congxiao Wang , Xiaoli Dong , Yongyao Xia . Tailored cathode electrolyte interphase via ethylene carbonate-free electrolytes enabling stable and wide-temperature operation of high-voltage LiCoO₂. Acta Physico-Chimica Sinica, 2025, 41(8): 100087-0. doi: 10.1016/j.actphy.2025.100087
9. [9]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
10. [10]
  Mingjie Lei , Wenting Hu , Kexin Lin , Xiujuan Sun , Haoshen Zhang , Ye Qian , Tongyue Kang , Xiulin Wu , Hailong Liao , Yuan Pan , Yuwei Zhang , Diye Wei , Ping Gao . Accelerating the reconstruction of NiSe₂ by Co/Mn/Mo doping for enhanced urea electrolysis. Acta Physico-Chimica Sinica, 2025, 41(8): 100083-0. doi: 10.1016/j.actphy.2025.100083
11. [11]
  Qing Li , Guangxun Zhang , Yuxia Xu , Yangyang Sun , Huan Pang . P-Regulated Hierarchical Structure Ni₂P Assemblies toward Efficient Electrochemical Urea Oxidation. Acta Physico-Chimica Sinica, 2024, 40(9): 2308045-0. doi: 10.3866/PKU.WHXB202308045
12. [12]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
13. [13]
  Hao GUO , Tong WEI , Qingqing SHEN , Anqi HONG , Zeting DENG , Zheng FANG , Jichao SHI , Renhong LI . Electrocatalytic decoupling of urea solution for hydrogen production by nickel foam-supported Co₉S₈/Ni₃S₂ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2141-2154. doi: 10.11862/CJIC.20240085
14. [14]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
15. [15]
  Mei Yan , Rida Feng , Yerdos·Tohtarkhan , Biao Long , Li Zhou , Chongshen Guo . Expansion and Extension of Liquid Saturated Vapor Measurement Experiment. University Chemistry, 2024, 39(3): 294-301. doi: 10.3866/PKU.DXHX202308103
16. [16]
  Zixuan Zhao , Miao Fan . “Carbon” with No “Ester”: A Boundless Journey of CO₂ Transformation. University Chemistry, 2025, 40(7): 213-217. doi: 10.12461/PKU.DXHX202409040
17. [17]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
18. [18]
  Xuan Zhou , Yi Fan , Zhuoqi Jiang , Zhipeng Li , Guowen Yuan , Laiying Zhang , Xu Hou . Liquid Gating Mechanism and Basic Properties Characterization: a New Experimental Design for Interface and Surface Properties in the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 113-120. doi: 10.12461/PKU.DXHX202407111
19. [19]
  Yongmin Zhang , Shuang Guo , Mingyue Zhu , Menghui Liu , Sinong Li . Design and Improvement of Physicochemical Experiments Based on Problem-Oriented Learning: a Case Study of Liquid Surface Tension Measurement. University Chemistry, 2024, 39(2): 21-27. doi: 10.3866/PKU.DXHX202307026
20. [20]
  Yi Fan , Zhuoqi Jiang , Zhipeng Li , Xuan Zhou , Jingan Lin , Laiying Zhang , Xu Hou . 偶极诱导液体门控可视化物质检测——化学“101计划”表界面性质应用实验新设计. University Chemistry, 2025, 40(8): 265-271. doi: 10.12461/PKU.DXHX202410061

Get Citation

PDF

XML

Metrics

PDF Downloads(226)
Abstract views(687)
HTML views(38)

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