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

  • 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

Figures(8)

  • 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.
  • 加载中
    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

  • 加载中
    1. [1]

      Wenyu Yuan Ying Wang Shuni Li Xiaolin Zhu Quanguo Zhai Shengli Gao . Preparation and Purification of Alkali Metals. University Chemistry, 2026, 41(2): 218-231. doi: 10.12461/PKU.DXHX202502111

    2. [2]

      Qiuting Zhang Fan Wu Jin Liu Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174

    3. [3]

      Hui WangAbdelkader LabidiMenghan RenFeroz ShaikChuanyi Wang . Recent Progress of Microstructure-Regulated g-C3N4 in Photocatalytic NO Conversion: The Pivotal Roles of Adsorption/Activation Sites. Acta Physico-Chimica Sinica, 2025, 41(5): 100039-0. doi: 10.1016/j.actphy.2024.100039

    4. [4]

      Peng XUShasha WANGNannan CHENAo WANGDongmei YU . Preparation of three-layer magnetic composite Fe3O4@polyacrylic acid@ZiF-8 for efficient removal of malachite green in water. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 544-554. doi: 10.11862/CJIC.20230239

    5. [5]

      Xuewei Qian Xingwen Sun Houjin Li Zhanxiang Liu Yuan Zheng Lin Wu Shuanglian Cai Ying Xiong Guangao Yu Qingwen Liu Jie Han Xin Du Chengshan Yuan Qihan Zhang Shuyong Zhang Jianrong Zhang . Basic Operations and Specification Suggestions for Organic Chemical Recrystallization Experiments. University Chemistry, 2025, 40(5): 66-75. doi: 10.12461/PKU.DXHX202503126

    6. [6]

      Shengbiao Zheng Liang Li Nini Zhang Ruimin Bao Ruizhang Hu Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096

    7. [7]

      Fugui XIDu LIZhourui YANHui WANGJunyu XIANGZhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291

    8. [8]

      Wei Li Jinfan Xu Yongjun Zhang Ying Guan . 共价有机框架整体材料的制备及食品安全非靶向筛查应用——推荐一个仪器分析综合化学实验. University Chemistry, 2025, 40(6): 276-285. doi: 10.12461/PKU.DXHX202406013

    9. [9]

      Xinlong XUChunxue JINGYuzhen CHEN . Bimetallic MOF-74 and derivatives: Fabrication and efficient electrocatalytic biomass conversion. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1545-1554. doi: 10.11862/CJIC.20250046

    10. [10]

      Ting YANGJia ANJinyu ZHANGRuonan FANRong YANXiaoxia JINGPanpan CHANGWei YAN . Synergistic enhancement of ion migration and sulfur conversion kinetics in lithium-sulfur batteries by CeO2/g-C3N4. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 519-530. doi: 10.11862/CJIC.20250274

    11. [11]

      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

    12. [12]

      Qin′ai FENGJianjun LILili ZHANGLinxin WUHuiling WANGWenjing HOULei WANGMingjie REN . Amphiphilic surface modification of magnetic adsorbents and its adsorption properties of two microplastics. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 789-807. doi: 10.11862/CJIC.20250208

    13. [13]

      Jingke LIUJia CHENYingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060

    14. [14]

      Zeyu XUAnlei DANGBihua DENGXiaoxin ZUOYu LUPing YANGWenzhu YIN . Evaluation of the efficacy of graphene oxide quantum dots as an ovalbumin delivery platform and adjuvant for immune enhancement. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1065-1078. doi: 10.11862/CJIC.20240099

    15. [15]

      Jing Wang Pingping Li Yuehui Wang Yifan Xiu Bingqian Zhang Shuwen Wang Hongtao Gao . Treatment and Discharge Evaluation of Phosphorus-Containing Wastewater. University Chemistry, 2024, 39(5): 52-62. doi: 10.3866/PKU.DXHX202309097

    16. [16]

      Zhi FANGLiang SUNMingze ZHENGWenhao SHENGHongliang HUANGChongli ZHONG . An aluminum-based metal-organic framework with slit pores for the efficient separation and recovery of electronic specialty gas C3F8. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2054-2062. doi: 10.11862/CJIC.20250096

    17. [17]

      Wenjuan SHIYuke LUXiuyuan LILei HOUYaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO2 adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220

    18. [18]

      Yi DINGPeiyu LIAOJianhua JIAMingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

    19. [19]

      Chuansong LINChuqing ZHANGShixiong LI . A Ni(Ⅱ) metal-organic framework based on the 4, 4′-biphenyldicarboxylic acid ligand and its adsorption performance for tetracycline. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 593-605. doi: 10.11862/CJIC.20250278

    20. [20]

      Jie ZHAOSen LIUQikang YINXiaoqing LUZhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385

Metrics
  • PDF Downloads(35)
  • Abstract views(4003)
  • HTML views(449)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return