Citation: Tao Chang, Xiaorui Gao, Li Bian, Xiying Fu, Mingxia Yuan, Huanwang Jing. Coupling of epoxides and carbon dioxide catalyzed by Brönsted acid ionic liquids[J]. Chinese Journal of Catalysis, ;2015, 36(3): 408-413. doi: 10.1016/S1872-2067(14)60227-8 shu

Coupling of epoxides and carbon dioxide catalyzed by Brönsted acid ionic liquids

1.
a Engineering Laboratory for Coalbed Gas Exploitation of Hebei Province, College of Science, Hebei University of Engineering, Handan 056038, Hebei, China;

Corresponding author: Huanwang Jing,
Received Date: 11 August 2014
Available Online: 15 September 2014
Fund Project: 河北省自然科学基金(B2012402001) (B2012402001) 国家自然科学基金(51202054, 21173106). (51202054, 21173106)

A series of Brönsted acid ionic liquids (BAILs) containing a long chain Brönsted acid site in the cationic part and a Lewis basic site in the anionic part were designed, synthesized, and used as catalyst for the coupling of epoxides and carbon dioxide to cyclic carbonates without a co-catalyst or co-solvent. The effects of catalyst structure and other parameters on the catalytic performance were investigated. The long chain 2-(N,N-dimethyldodecylammonium) acetic acid bromide ([(CH₂COOH)DMDA]Br) showed high catalytic activity and good reusability. This protocol was expanded to various epoxides, which gave the corresponding cyclic carbonates in good yields. The acidity of the catalyst influenced its catalytic activity.
- Carbon dioxide fixation,
- Coupling reaction,
- Brönsted acidic ionic liquid,
- Cyclic carbonate,
- Hammett acidity
1. [1]
  [1] Markewitz P, Kuckshinrichs W, Leitner W, Linssen J, Zapp P, Bongartz R, Schreiber A, Müller T E. Energy Environ Sci, 2012, 5: 7281
2. [2]
  [2] Li L, Zhao N, Wei W, Sun Y H. Fuel, 2013, 108: 112
3. [3]
  [3] Li H, Bhadury P S, Song B A, Yang S. RSC Adv, 2012, 2: 12525
4. [4]
  [4] Fan Q J, Liu J H, Chen J, Xia C G. Chin J Catal(樊启佳, 刘建华, 陈静, 夏春谷. 催化学报), 2012, 33: 1435
5. [5]
  [5] Castro-Osma J A, Lara-Sánchez A, North M, Otero A, Villuendas P. Catal Sci Technol, 2012, 2: 1021
6. [6]
  [6] Lu X B, Darensbourg D J. Chem Soc Rev, 2012, 41: 1462
7. [7]
  [7] Ren W M, Wu G P, Lin F, Jiang J Y, Liu C, Luo Y, Lu X B. Chem Sci, 2012, 3: 2094
8. [8]
  [8] Beattie C, North M. Chem Eur J, 2014, 20: 8182
9. [9]
  [9] Xie Y, Wang T T, Yang R X, Huang N Y, Zou K, Deng W Q. ChemSusChem, 2014, 7: 2110
10. [10]
  [10] Iksi S, Aghmiz A, Rivas R, González M D, Cuesta-Aluja L, Castilla J, Orejón A, Guemmout F E, Masdeu-Bultó A M. J Mol Catal A, 2014, 383-384: 143
11. [11]
  [11] Li B, Zhang L L, Song Y Y, Bai D S, Jing H W. J Mol Catal A, 2012, 363-364: 26
12. [12]
  [12] Bai D S, Duan S H, Hai L, Jing H W. ChemCatChem, 2012, 4: 1752
13. [13]
  [13] Ema T, Miyazaki Y, Koyama S, Yano Y, Sakai T. Chem Commun, 2012, 48: 4489
14. [14]
  [14] Wei R J, Zhang X H, Du B Y, Fan Z Q, Qi G R. J Mol Catal A, 2013, 379: 38
15. [15]
  [15] Tharun J, Hwang Y, Roshan R, Ahn S, Kathalikkattil A C, Park D W. Catal Sci Technol, 2012, 2: 1674
16. [16]
  [16] Li C Y, Wu C R, Liu Y C, Ko B T. Chem Commun, 2012, 48: 9628
17. [17]
  [17] Roeser J, Kailasam K, Thomas A. ChemSusChem, 2012, 5: 1793
18. [18]
  [18] Dai W L, Jin B, Luo S L, Luo X B, Tu X M, Au C T. Catal Today, 2014, 233: 92
19. [19]
  [19] Chen J X, Jin B, Dai W L, Deng S L, Cao L R, Cao Z J, Luo S L, Luo X B, Tu X M, Au C T. Appl Catal A, 2014, 484: 26
20. [20]
  [20] Yu T, Weiss R G. Green Chem, 2012, 14: 209
21. [21]
  [21] Gao J, Song Q W, He L N, Liu C, Yang Z Z, Han X, Li X D, Song Q C. Tetrahedron, 2012, 68: 3835
22. [22]
  [22] He Q, O'Brien J W, Kitselman K A, Tompkins L E, Curtis G C T, Kerton F M. Catal Sci Technol, 2014, 4: 1513
23. [23]
  [23] Ghazali-Esfahani S, Song H B, Pâunescu E, Bobbink F D, Liu H Z, Fei Z F, Laurenczy G, Bagherzadeh M, Yan N, Dyson P J. Green Chem, 2013, 15: 1584
24. [24]
  [24] Dai W L, Jin B, Luo S L, Luo X B, Tu X M, Au C T. J Mol Catal A, 2013, 378: 326
25. [25]
  [25] Song Q W, He L N, Wang J Q, Yasuda H, Sakakura T. Green Chem, 2013, 15: 110
26. [26]
  [26] Tharun J, Kim D W, Roshan R, Hwang Y, Park D W. Catal Commun, 2013, 31: 62
27. [27]
  [27] Wong W L, Lee L Y S, Ho K P, Zhou Z Y, Fan T, Lin Z Y, Wong K Y. Appl Catal A, 2014, 472: 160
28. [28]
  [28] Wang F, Xu C Z, Li Z, Xia C G, Chen J. J Mol Catal A, 2014, 385: 133
29. [29]
  [29] Dai W L, Jin B, Luo S L, Luo X B, Tu X M, Au C T. Appl Catal A, 2014, 470: 183
30. [30]
  [30] Xiao L F, Sun D, Yue C T, Wu W. J CO₂ Utilization, 2014, 6: 1
31. [31]
  [31] Dai W L, Jin B, Luo S L, Yin S F, Luo X B, Au C T. J CO₂ Utilization, 2013, 3-4: 7
32. [32]
  [32] Sun J, Wang J Q, Cheng W G, Zhang J X, Li X H, Zhang S J, She Y B. Green Chem, 2012, 14: 654
33. [33]
  [33] Watile R A, Deshmukh K M, Dhake K P, Bhanage B M. Catal Sci Technol,2012, 2: 1051
34. [34]
  [34] Qu J, Cao C Y, Dou Z F, Liu H, Yu Y, Li P, Song W G. ChemSusChem, 2012, 5: 652
35. [35]
  [35] Xiao L F, Lü D W, Su D, Wu W, Li H F. J Clean Prod, 2014, 67: 285
36. [36]
  [36] Han L N, Choi S J, Park M S, Lee S M, Kim Y J, Kim M I, Liu B Y, Park D W. React Kinet Mech Catal, 2012, 106: 25
37. [37]
  [37] Zhang Y Y, Yin S F, Luo S L, Au C T. Ind Eng Chem Res, 2012, 51: 3951
38. [38]
  [38] He L Q, Qin S J, Chang T, Sun Y Z, Zhao J Q. Int J Mol Sci, 2014, 15: 8656
39. [39]
  [39] He L Q, Qin S J, Chang T, Sun Y Z, Gao X R. Catal Sci Technol, 2013, 3: 1102
40. [40]
  [40] Chang T, He L Q, Bian L, Han H Y, Yuan M X, Gao X R. RSC Adv, 2014, 4: 727
41. [41]
  [41] Fei Z F, Zhao D B, Geldbach T J, Scopelliti R, Dyson P J. Chem Eur J, 2004, 10: 4886
42. [42]
  [42] Zhang J L, Han B X, Zhao Y J, Li J S, Hou M Q, Yang G Y. Chem Commun, 2011, 47: 1033
43. [43]
  [43] Miao C X, Wang J Q, Wu Y, Du Y, He L N. ChemSusChem, 2008, 1: 236
1. [1]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
2. [2]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
3. [3]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
4. [4]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
5. [5]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
6. [6]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
7. [7]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
8. [8]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
9. [9]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
10. [10]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
11. [11]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
12. [12]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
13. [13]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
14. [14]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
15. [15]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
16. [16]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
17. [17]
  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
18. [18]
  Tong Zhou , Jun Li , Zitian Wen , Yitian Chen , Hailing Li , Zhonghong Gao , Wenyun Wang , Fang Liu , Qing Feng , Zhen Li , Jinyi Yang , Min Liu , Wei Qi . Experiment Improvement of “Redox Reaction and Electrode Potential” Based on the New Medical Concept. University Chemistry, 2024, 39(8): 276-281. doi: 10.3866/PKU.DXHX202401005
19. [19]
  Ji-Quan Liu , Huilin Guo , Ying Yang , Xiaohui Guo . Calculation and Discussion of Electrode Potentials in Redox Reactions of Water. University Chemistry, 2024, 39(8): 351-358. doi: 10.3866/PKU.DXHX202401031
20. [20]
  Tao Wen , Tao Zhang , Changguo Sun , Jinyu Liu . Preparation of Dess-Martin Reagent and Its Application in Oxidizing Cyclohexanol. University Chemistry, 2024, 39(5): 20-26. doi: 10.3866/PKU.DXHX202309055

Get Citation

PDF

XML

Metrics

PDF Downloads(248)
Abstract views(797)
HTML views(61)

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