Citation: Guo Zhenbin, Zhang Yuanyuan, Feng Xiao. Separation and Purification of C₄~C₆ Hydrocarbons Using Metal-organic Frameworks[J]. Acta Chimica Sinica, ;2020, 78(5): 397-406. doi: 10.6023/A20030081 shu

Separation and Purification of C₄~C₆ Hydrocarbons Using Metal-organic Frameworks

a.
School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081
b.
Advanced Research Institute of Multidisciplinary Science, Beijing Institute of Technology, Beijing 100081

Corresponding author: Zhang Yuanyuan, 6120190112@bit.edu.cn
Received Date: 21 March 2020
Available Online: 20 April 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21922502, 21674012)the National Natural Science Foundation of China 21922502the National Natural Science Foundation of China 21674012

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As important chemical raw materials and energy source, C₄~C₆ hydrocarbons are mainly used to produce polymer rubber, plastics and high-quality gasoline, which requires high purity of the raw materials. For example, the purity requirement in 1, 3-butadiene polymerization reactor is higher than 99.5%. When producing butyl rubber, tert-butylamine, pivalic acid, etc., the purity of isobutylene should surpass 99%. In the traditional petrochemical industry, C₄~C₆ hydrocarbons are mostly separated and purified through distillation, yet suffering from large energy consumption, high equipment cost and poor economic benefits. Adsorption separation with solid adsorbents can not only reduce energy cost and environmental footprints, but also improve separation efficiency. Metal-organic frameworks (MOFs) are a class of crystalline porous materials assembled from metal ions or clusters and organic linkers. Compared with zeolite, activated carbon and silica gel, MOFs feature high porosity, well-defined open channels, rich functional groups and diverse structures, showing great potentials in gas storage and separation, sensing, catalysis, photoelectric devices, drug release and delivery. Up to now, there have been many reports on separation and purification of C₄~C₆ hydrocarbons using MOFs by different mechanisms. Specifically, highly selective separation can be achieved by precisely adjusting the size and shape of the MOF channels to match the size of the target molecule. Besides, selecting MOFs with specific functional groups, open metal sites or flexible skeletons to regulate the interactions between the gas molecules and backbone, can also achieve efficient separation. This review introduced the importance of C₄~C₆ hydrocarbons separation and summarized the current research progress of using MOFs to separate and purify C₄~C₆ hydrocarbons. In addition, we also summed up the challenges of using MOFs as industrial adsorbents and pointed out the possible research directions in the future, which may provide ideas for designing new MOFs with high performance for crucial separation processes.
- metal-organic frameworks,
- C₄~C₆ hydrocarbons,
- adsorption,
- separation,
- purification
1. [1]
  Bender, M. ChemBioEng Rev. 2014, 1, 136. doi: 10.1002/cben.201400016
2. [2]
  Gehre, M.; Guo, Z.; Rothenberg, G.; Tanase, S. ChemSusChem 2017, 10, 3947. doi: 10.1002/cssc.201700657
3. [3]
  Ed.: Myers, R. A. Handbook of Petroleum Refining Processes, McGraw-Hill, New York, 2004.
4. [4]
  Greensfelder, B. S.; Voge, H. H. Ind. Eng. Chem. Res. 1945, 37, 514. doi: 10.1021/ie50426a008
5. [5]
  Li, J.-R.; Kuppler, R. J.; Zhou, H.-C. Chem. Soc. Rev. 2009, 38, 1477. doi: 10.1039/b802426j
6. [6]
  Tijsebaert, B.; Varszegi, C.; Gies, H.; Xiao, F. S.; Bao, X.; Tatsumi, T.; Muller, U.; De Vos, D. Chem. Commun. 2008, 2480.
7. [7]
  (a) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Science 2005, 310, 1166. (b) Kitagawa, S.; Kitaura, R.; Noro, S. Angew. Chem., Int. Ed. 2004, 43, 2334. (c) Ferey, G. Chem. Soc. Rev. 2008, 37, 191. (d) Farha, O. K.; Hupp, J. T. Acc. Chem. Res. 2010, 43, 1166. (e) Eddaoudi, M.; Li, H.; Yaghi, O. M. J. Am. Chem. Soc. 2000, 122, 1391. (f) Farha, O. K.; Eryazici, I.; Jeong, N. C.; Hauser, B. G.; Wilmer, C. E.; Sarjeant, A. A.; Snurr, R. Q.; Nguyen, S. T.; Yazaydın, A. Ö.; Hupp, J. T. J. Am. Chem. Soc. 2012, 134, 15016.
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
  (a) Cui, W. G.; Hu, T. L.; Bu, X. H. Adv. Mater. 2019, 32, 1806445. (b) Li, J. R.; Kuppler, R. J.; Zhou, H. C. Chem. Soc. Rev. 2009, 38, 1477.
13. [13]
  Sircar, S.; Mohr, R.; Ristic, C.; Rao, M. B. J. Phys. Chem. B 1999, 103, 6539. doi: 10.1021/jp9903817
14. [14]
  Hartmann, M.; Kunz, S.; Himsl, D.; Tangermann, O.; Ernst, S.; Wagener, A. Langmuir 2008, 24, 8634. doi: 10.1021/la8008656
15. [15]
  Schoonheydt, R. A.; Weckhuysen, B. M. Phys. Chem. Chem. Phys. 2009, 11, 2794. doi: 10.1039/b905015a
16. [16]
  Barnett, B. R.; Parker, S. T.; Paley, M. V.; Gonzalez, M. I.; Biggins, N.; Oktawiec, J.; Long, J. R. J. Am. Chem. Soc. 2019, 141, 18325. doi: 10.1021/jacs.9b09942
17. [17]
  Jiao, J.; Liu, H.; Bai, D.; He, Y. Inorg. Chem. 2016, 55, 3974. doi: 10.1021/acs.inorgchem.6b00253
18. [18]
  Kim, H.; Park, J.; Jung, Y. Phys. Chem. Chem. Phys. 2013, 15, 19644. doi: 10.1039/c3cp52980k
19. [19]
  Jiao, J.; Liu, H.; Bai, D.; He, Y. Inorg. Chem. 2016, 55, 3974. doi: 10.1021/acs.inorgchem.6b00253
20. [20]
  Zhang, Z.; Yang, Q.; Cui, X.; Yang, L.; Bao, Z.; Ren, Q.; Xing, H. Angew. Chem., Int. Ed. 2017, 56, 16282. doi: 10.1002/anie.201708769
21. [21]
  Cui, J.; Zhang, Z.; Tan, B.; Zhang, Y.; Wang, P.; Cui, X.; Xing, H. Chem. Asian. J. 2019, 14, 3572. doi: 10.1002/asia.201900735
22. [22]
  Lange, M.; Kobalz, M.; Bergmann, J.; Lässig, D.; Lincke, J.; Möllmer, J.; Möller, A.; Hofmann, J.; Krautscheid, H.; Staudt, R.; Gläser, R. J. Mater. Chem. A 2014, 2, 8075. doi: 10.1039/C3TA15331B
23. [23]
  Kishida, K.; Okumura, Y.; Watanabe, Y.; Mukoyoshi, M.; Bracco, S.; Comotti, A.; Sozzani, P.; Horike, S.; Kitagawa, S. Angew. Chem., Int. Ed. 2016, 55, 13784.  doi: 10.1002/anie.201607676
24. [24]
  Liao, P.-Q.; Huang, N.-Y.; Zhang, W.-X.; Zhang, J.-P.; Chen, X.-M. Science 2017, 356, 1193. doi: 10.1126/science.aam7232
25. [25]
  Chen, B.; Liang, C.; Yang, J.; Contreras, D. S.; Clancy, Y. L.; Lobkovsky, E. B.; Yaghi, O. M.; Dai, S. Angew. Chem., Int. Ed. 2006, 45, 1390. doi: 10.1002/anie.200502844
26. [26]
  Herm, Z. R.; Wiers, B. M.; Mason, J. A.; Baten, J. M.; Hudson, M. R.; Zajdel, P.; Brown, C. M.; Masciocchi, N.; Krishna, R.; Long, J. R. Science 2013, 340, 960. doi: 10.1126/science.1234071
27. [27]
  Mendes, P. A. P.; Horcajada, P.; Rives, S.; Ren, H.; Rodrigues, A. E.; Devic, T.; Magnier, E.; Trens, P.; Jobic, H.; Ollivier, J.; Maurin, G.; Serre, C.; Silva, J. A. C. Adv. Funct. Mater. 2014, 24, 7666. doi: 10.1002/adfm.201401974
28. [28]
  Assen, A. H.; Belmabkhout, Y.; Adil, K.; Bhatt, P. M.; Xue, D. X.; Jiang, H.; Eddaoudi, M. Angew. Chem., Int. Ed. 2015, 54, 14353. doi: 10.1002/anie.201506345
29. [29]
  Wang, H.; Dong, X.; Lin, J.; Teat, S. J.; Jensen, S.; Cure, J.; Alexandrov, E. V.; Xia, Q.; Tan, K.; Wang, Q.; Olson, D. H.; Proserpio, D. M.; Chabal, Y. J.; Thonhauser, T.; Sun, J.; Han, Y.; Li, J. Nat. Commun. 2018, 9, 1745. doi: 10.1038/s41467-018-04152-5
30. [30]
  Wang, H.; Dong, X.; Velasco, E.; Olson, D. H.; Han, Y.; Li, J. Energy Environ. Sci. 2018, 11, 1226. doi: 10.1039/C8EE00459E
31. [31]
  Ding, N.; Li, H.-W.; Wang, Q.-Y.; Wang, S.; Ma, L.; Zhou, J.-W.; Wang, B. J. Am. Chem. Soc. 2016, 138, 10100. doi: 10.1021/jacs.6b06051
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Separation and Purification of C₄~C₆ Hydrocarbons Using Metal-organic Frameworks