Surface cross-linking of ZIF-8/polyimide mixed matrix membranes (MMMs) for gas separation

Industrial and Engineering Chemistry Research

Volumn 52, Issue 21, 2013, Pages 6991-7001

  Wijenayake, Sumudu N ^a   Panapitiya, Nimanka P ^a   Versteeg, Saskia H ^a   Nguyen, Cindy N ^a   Goel, Srishti ^a   Balkus, Kenneth J ^a   Musselman, Inga H ^a   Ferraris, John P ^a  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COST-EFFICIENT; ETHYLENE DIAMINE; GAS SEPARATIONS; HIGH GAS FLUXES; HIGH SELECTIVITY; MIXED MATRIX MEMBRANES; PERMSELECTIVE PROPERTIES; UPPER BOUND;

CARBON DIOXIDE; LOADING; POLYIMIDES; SEPARATION; VAPORS;

GAS PERMEABLE MEMBRANES;

EID: 84878384419     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie400149e     Document Type: Article

References (83)

1. Koros, W. J.; Mahajan, R. Pushing the Limits on Possibilities for Large Scale Gas Separation: Which Strategies? J. Membr. Sci. 2000, 175, 181-196
2. Koros, W. J. Gas Separation Membranes: Needs for Combined Materials Science and Processing Approaches Macromol. Symp. 2002, 188, 13-22
3. Koros, W. J.; Fleming, G. K. Membrane-Based Gas Separation J. Membr. Sci. 1993, 83, 1-80
4. Ghosal, K.; Freeman, B. D. Gas Separation Using Polymer Membranes: An Overview Polym. Adv. Technol. 1994, 5, 673-697
5. Hosseini, S. S.; Teoh, M. M.; Chung, T. S. Hydrogen Separation and Purification in Membranes of Miscible Polymer Blends with Interpenetration Networks Polymer 2008, 49, 1594-1603
6. Alexander Stern, S. Polymers for Gas Separations: The next decade J. Membr. Sci. 1994, 94, 1-65
7. Sircar, S.; Golden, T. C. Purification of Hydrogen by Pressure Swing Adsorption Sep. Sci. Technol. 2000, 35, 667-687
8. Hinchliffe, A. B.; Porter, K. E. A Comparison of Membrane Separation and Distillation Chem. Eng. Res. Des. 2000, 78, 255-268
9. Buonomenna, M. G.; Yave, W.; Golemme, G. Some Approaches for High Performance Polymer Based Membranes for Gas Separation: Block Copolymers, Carbon Molecular Sieves and Mixed Matrix Membranes RSC Adv. 2012, 2, 10745-10773
10. Shao, L.; Low, B. T.; Chung, T. S.; Greenberg, A. R. Polymeric Membranes for the Hydrogen Economy: Contemporary Approaches and Prospects for the Future J. Membr. Sci. 2009, 327, 18-31
11. Ismail, A. F.; David, L. I. B. A Review on the Latest Development of Carbon Membranes for Gas Separation J. Membr. Sci. 2001, 193, 1-18
12. Zimmerman, C. M.; Singh, A.; Koros, W. J. Tailoring Mixed Matrix Composite Membranes for Gas Separations J. Membr. Sci. 1997, 137, 145-154
13. Sheffel, J. A.; Tsapatsis, M. A Model for the Performance of Microporous Mixed Matrix Membranes with Oriented Selective Flakes J. Membr. Sci. 2007, 295, 50-70
14. Mahajan, R.; Koros, W. J. Factors Controlling Successful Formation of Mixed-Matrix Gas Separation Materials Ind. Eng. Chem. Res. 2000, 39, 2692-2696
15. Chung, T. S.; Jiang, L. Y.; Li, Y.; Kulprathipanja, S. Mixed Matrix Membranes (MMMs) Comprising Organic Polymers with Dispersed Inorganic Fillers for Gas Separation Prog. Polym. Sci. 2007, 32 (4) 483-507
16. Hillock, A. M. W.; Miller, S. J.; Koros, W. J. Crosslinked Mixed Matrix Membranes for the Purification of Natural Gas: Effects of Sieve Surface Modification J. Membr. Sci. 2008, 314, 193-199
17. Li, Y.; Chung, T. S.; Cao, C.; Kulprathipanja, S. The Effects of Polymer Chain Rigidification, Zeolite Pore Size and Pore Blockage on Polyethersulfone (PES)-Zeolite A Mixed Matrix Membranes J. Membr. Sci. 2005, 260, 45-55
18. Vu, D. Q.; Koros, W. J.; Miller, S. J. Mixed Matrix Membranes Using Carbon Molecular Sieves: I. Preparation and Experimental Results J. Membr. Sci. 2003, 211, 311-334
19. Vu, D. Q.; Koros, W. J.; Miller, S. J. Mixed Matrix Membranes Using Carbon Molecular Sieves: II. Modeling Permeation Behavior J. Membr. Sci. 2003, 211, 335-348
20. Weng, T. H.; Tseng, H. H.; Wey, M.-Y. Fabrication and Characterization of Poly(phenylene oxide)/SBA-15/Carbon Molecule Sieve Multilayer Mixed Matrix Membrane for Gas Separation Int. J. Hydrogen Energy 2010, 35, 6971-6983
21. Esteves, I. A. A. C.; Mota, J. P. B. Gas Separation by a Novel Hybrid Membrane/Pressure Swing Adsorption Process Ind. Eng. Chem. Res. 2007, 46, 5723-5733
22. Kim, S.; Chen, L.; Johnson, J. K.; Marand, E. Polysulfone and Functionalized Carbon Nanotube Mixed Matrix Membranes for Gas Separation: Theory and Experiment J. Membr. Sci. 2007, 294, 147-158
23. Kim, S.; Marand, E.; Ida, J.; Guliants, V. V. Polysulfone and Mesoporous Molecular Sieve MCM-48 Mixed Matrix Membranes for Gas Separation Chem. Mater. 2006, 18, 1149-1155
24. Reid, B. D.; Ruiz-Trevino, F. A.; Musselman, I. H.; Balkus, K. J., Jr.; Ferraris, J. P. Gas Permeability Properties of Polysulfone Membranes Containing the Mesoporous Molecular Sieve MCM-41 Chem. Mater. 2001, 13, 2366-2373
25. Zhang, Y.; Balkus, K. J., Jr.; Musselman, I. H.; Ferraris, J. P. Mixed-Matrix Membranes Composed of Matrimid® and Mesoporous ZSM-5 Nanoparticles J. Membr. Sci. 2008, 325, 28-39
26. Car, A.; Stropnik, C.; Peinemann, K. V. Hybrid Membrane Materials with Different Metal-Organic Frameworks (MOFs) for Gas Separation Desalination 2006, 200, 424-426
27. Perez, E. V.; Balkus, K. J., Jr.; Ferraris, J. P.; Musselman, I. H. Mixed-Matrix Membranes Containing MOF-5 for Gas Separations J. Membr. Sci. 2009, 328, 165-173
28. Zhang, Y.; Musselman, I. H.; Ferraris, J. P.; Balkus, K. J., Jr. Gas Permeability Properties of Matrimid® Membranes Containing the Metal-Organic Framework Cu-BPY-HFS J. Membr. Sci. 2008, 313, 170-181
29. Ordoñez, M. J. C.; Balkus, K. J., Jr.; Ferraris, J. P.; Musselman, I. H. Molecular Sieving Realized with ZIF-8/Matrimid® Mixed-Matrix Membranes J. Membr. Sci. 2010, 361, 28-37
30. Bae, T. H.; Lee, J. S.; Qiu, W.; Koros, W. J.; Jones, C. W.; Nair, S. A High-Performance Gas-Separation Membrane Containing Submicrometer-Sized Metal-Organic Framework Crystals Angew. Chem., Int. Ed. 2010, 49, 9863-9866
31. Balkus, K. J., Jr.; Ferraris, J. P.; Musselman, I. H. Mixed Matrix Membranes Based on Metal Organic Frameworks. In Advanced Materials for Membrane Preparation [Online]; Buonomenna, M. G.; Golemme, G., Eds.; Bentham Science Publishers: Rende, Italy, 2012; pp 83-93. http://www.eurekaselect.com/100084/ Chapter/mixed-matrix-membranes-based-on-metal-organic-framework (accessed Jan 7 2013).
32. Mahajan, R.; Burns, R.; Schaeffer, M.; Koros, W. J. Challenges in Forming Successful Mixed Matrix Membranes with Rigid Polymeric Materials J. Appl. Polym. Sci. 2002, 86, 881-890
33. Shu, S.; Husain, S.; Koros, W. J. A General Strategy for Adhesion Enhancement in Polymeric Composites by Formation of Nanostructured Particle Surfaces J. Phys. Chem. C 2006, 111, 652-657
34. Rowsell, J. L. C.; Yaghi, O. M. Metal-Organic Frameworks: A New Class of Porous Materials Microporous Mesoporous Mater. 2004, 73, 3-14
35. Park, K. S.; Ni, Z.; Cote, A. P.; Choi, J. Y.; Huang, R.; Uribe-Romo, F. J.; Chae, H. K.; O'Keeffe, M.; Yaghi, O. M. Exceptional Chemical and Thermal Stability of Zeolitic Imidazolate Frameworks Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 10186-10191
36. Hayashi, H.; Cote, A. P.; Furukawa, H.; O'Keeffe, M.; Yaghi, O. M. Zeolite A Imidazolate Frameworks Nat. Mater. 2007, 6, 501-506
37. 4 Separation J. Am. Chem. Soc. 2009, 132, 76-78
38. Li, Y.; Liang, F.; Bux, H.; Yang, W.; Caro, J. Zeolitic Imidazolate Framework ZIF-7 Based Molecular Sieve Membrane for Hydrogen Separation J. Membr. Sci. 2010, 354, 48-54
39. Huang, A.; Bux, H.; Steinbach, F.; Caro, J. Molecular-Sieve Membrane with Hydrogen Permselectivity: ZIF-22 in LTA Topology Prepared with 3-Aminopropyltriethoxysilane As Covalent Linker Angew. Chem., Int. Ed. 2010, 49, 4958-4961
40. 2/CO Mixture J. Membr. Sci. 2010, 353, 36-40
41. 8 Molecular Sieve Separation Chem. Mater. 2011, 23, 2262-2269
42. Zornoza, B.; Tellez, C.; Coronas, J.; Gascon, J.; Kapteijn, F. Metal Organic Framework Based Mixed Matrix Membranes: An Increasingly Important Field of Research with a Large Application Potential Microporous Mesoporous Mater. 2013, 166, 67-78
43. Tanh Jeazet, H. B.; Staudt, C.; Janiak, C. Metal-Organic Frameworks in Mixed-Matrix Membranes for Gas Separation Dalton Trans. 2012, 41, 14003-14027
44. Diaz, K.; Lopez-Gonzalez, M.; del Castillo, L. F.; Riande, E. Effect of Zeolitic Imidazolate Frameworks on the Gas Transport Performance of ZIF-8-poly(1,4-phenylene ether-ether-sulfone) Hybrid Membranes J. Membr. Sci. 2011, 283, 206-213
45. 2 Binary Gas Mixture Separations Sep. Purif. Technol. 2011, 81, 31-40
46. Zornoza, B.; Seoane, B.; Zamaro, J. M.; Téllez, C.; Coronas, J. Combination of MOFs and Zeolites for Mixed-Matrix Membranes ChemPhysChem 2012, 12, 2781-2785
47. Zhang, C.; Dai, Y.; Johnson, J. R.; Karvan, O.; Koros, W. J. High Performance ZIF-8/6FDA-DAM Mixed Matrix Membrane for Propylene/Propane Separations J. Membr. Sci. 2012, 389, 34-42
48. 2 Separations J. Membr. Sci. 2012, 401, 76-82
49. Song, Q.; Nataraj, S. K.; Roussenova, M. V.; Tan, J. C.; Hughes, D. J.; Li, W.; Bourgoin, P.; Alam, M. A.; Cheetham, A. K.; Al-Muhtaseb, S. A.; Sivaniah, E. Zeolitic Imidazolate Framework (ZIF-8) Based Polymer Nanocomposite Membranes for Gas Separation Energy Environ. Sci. 2012, 5, 8359-8369
50. Yang, T.; Shi, G. M.; Chung, T. S. Symmetric and Asymmetric Zeolitic Imidazolate Frameworks (ZIFs)/Polybenzimidazole (PBI) Nanocomposite Membranes for Hydrogen Purification at High Temperatures Adv. Energy Mater. 2012, 2, 1358-1367
51. Seoane, B.; Zamaro, J. M.; Tellez, C.; Coronas, J. Insight into the Crystal Synthesis, Activation and Application of ZIF-20 RSC Adv. 2011, 1, 917-922
52. Yang, T.; Xiao, Y.; Chung, T. S. Poly-/Metal-Benzimidazole Nanocomposite Membranes for Hydrogen Purification Energy Environ. Sci. 2011, 4, 4171-4180
53. Wind, J. D.; Staudt-Bickel, C.; Paul, D. R.; Koros, W. J. Solid-State Covalent Cross-Linking of Polyimide Membranes for Carbon Dioxide Plasticization Reduction Macromolecules 2003, 36, 1882-1888
54. 4 Separation Characteristics of Polyimides by Chemical Crosslinking J. Membr. Sci. 1999, 155, 145-154
55. Du, N.; Cin, M. M. D.; Pinnau, I.; Nicalek, A.; Robertson, G. P.; Guiver, M. D. Azide-based Cross-Linking of Polymers of Intrinsic Microporosity (PIMs) for Condensable Gas Separation Macromol. Rapid Commun. 2011, 32, 631-636
56. Shao, L.; Lau, C.-H.; Chung, T. S. A Novel Strategy for Surface Modification of Polyimide Membranes by Vapor-Phase Ethylenediamine (EDA) for Hydrogen Purification Int. J. Hydrogen Energy 2009, 34, 8716-8722
57. Hayes, R. A. Amine-Modified Polyimide Membranes. U.S. Patent 4,981,497, 1991.
58. Shao, L.; Chung, T. S.; Goh, S. H.; Pramoda, K. P. Polyimide Modification by a Linear Aliphatic Diamine to Enhance Transport Performance and Plasticization Resistance J. Membr. Sci. 2005, 256, 46-56
59. Liu, Y.; Wang, R.; Chung, T. S. Chemical Cross-Linking Modification of Polyimide Membranes for Gas Separation J. Membr. Sci. 2001, 189, 231-239
60. 2 Separation Macromolecules 2008, 41, 1297-1309
61. Shao, L.; Liu, L.; Cheng, S. X.; Huang, Y.-D.; Ma, J. Comparison of Diamino Cross-Linking in Different Polyimide Solutions and Membranes by Precipitation Observation and Gas Transport J. Membr. Sci. 2008, 312, 174-185
62. Aberg, C. M.; Ozcam, A. E.; Majikes, J. M.; Seyam, M. A.; Spontak, R. J. Extended Chemical Crosslinking of a Thermoplastic Polyimide: Macroscopic and Microscopic Property Development Macromol. Rapid Commun. 2008, 29, 1461-1466
63. 2 Separation Sep. Purif. Technol. 2010, 76, 132-139
64. Vanherck, K.; Cano-Odena, A.; Koeckelberghs, G.; Dedroog, T.; Vankelecom, I. A Simplified Diamine Crosslinking Method for PI Nanofiltration Membranes J. Membr. Sci. 2010, 353, 135-143
65. NETL Test Protocol-Testing of Hydrogen Separation Membranes; DOE/NETL-2008 /1335; U.S. Department of Energy: Washington, DC, 2008.
66. Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O'Keeffe, M.; Yaghi, O. M. Modular Chemistry: Secondary Building Units As a Basis for the Design of Highly Porous and Robust Metal-Organic Carboxylate Frameworks Acc. Chem. Res. 2001, 34, 319-330
67. Wu, H.; Zhou, W.; Yildirim, T. Hydrogen Storage in a Prototypical Zeolitic Imidazolate Framework-8 J. Am. Chem. Soc. 2007, 129, 5314-5315
68. Bux, H.; Liang, F.; Li, Y.; Cravillon, J.; Wiebcke, M.; Caro, J. Zeolitic Imidazolate Framework Membrane with Molecular Sieving Properties by Microwave-Assisted Solvothermal Synthesis J. Am. Chem. Soc. 2009, 131, 16000-16001
69. Kanehashi, S.; Nakagawa, T.; Nagai, K.; Duthie, X.; Kentish, S.; Stevens, G. Effects of Carbon Dioxide-Induced Plasticization on the Gas Transport Properties of Glassy Polyimide Membranes J. Membr. Sci. 2007, 298, 147-155
70. Lin, W. H.; Chung, T. S. Gas Permeability, Diffusivity, Solubility, and Aging Characteristics of 6FDA-Durene Polyimide Membranes J. Membr. Sci. 2001, 186, 183-193
71. Chung, T. S.; Lin, W. H.; Vora, R. H. The Effect of Shear Rates on Gas Separation Performance of 6FDA-Durene Polyimide Hollow Fibers J. Membr. Sci. 2000, 167, 55-66
72. Chung, T. S.; Kafchinski, E. R.; Vora, R. Development of a Defect-Free 6FDA-Durene Asymmetric Hollow Fiber and Its Composite Hollow Fibers J. Membr. Sci. 1994, 88, 21-36
73. Husk, G. R.; Cassidy, P. E.; Gebert, K. L. Synthesis and Characterization of a Series of Polyimides Derived from 4,4′-[2,2, 2trifluoro1(trifluoromethyl)ethylidene]bis[1,3isobenzofurandione] Macromolecules 1988, 21, 1234-1238
74. Reid, B. D.; Ruiz-Trevino, F. A.; Musselman, I. H.; Balkus, K. J., Jr.; Ferraris, J. P. Gas Permeability Properties of Polysulfone Membranes Containing the Mesoporous Molecular Sieve MCM-41 Chem. Mater. 2001, 13, 2366-2373
75. Hashemifard, S. A.; Ismail, A. F.; Matsuura, T. Co-Casting Technique for Fabricating Dual-Layer Flat Sheet Membranes for Gas Separation J. Membr. Sci. 2011, 375, 258-267
76. Fairen-Jimenez, D.; Moggach, S. A.; Wharmby, M. T.; Wright, P. A.; Parsons, S.; DuÌren, T. Opening the Gate: Framework Flexibility in ZIF-8 Explored by Experiments and Simulations J. Am. Chem. Soc. 2011, 133, 8900-8902
77. Powell, C. E.; Duthie, X. J.; Kentish, S. E.; Qiao, G. G.; Stevens, G. W. Reversible Diamine Cross-Linking of Polyimide Membranes J. Membr. Sci. 2007, 291, 199-209
78. Xu, J.; Froment, G. F. Methane Steam Reforming, Methanation and Water-Gas Shift: I. Intrinsic Kinetics AIChE J. 1989, 35, 88-96
79. Low, B. T.; Xiao, Y.; Chung, T. S. Amplifying the Molecular Sieving Capability of Polyimide Membranes via Coupling of Diamine Networking and Molecular Architecture Polymer 2009, 50, 3250-3258
80. Le Roux, J. D.; Paul, D. R. Preparation of Composite Membranes by a Spin Coating Process J. Membr. Sci. 1992, 74, 233-252
81. Merkel, T. C.; Lin, H.; Wei, X.; Baker, R. Power Plant Post-Combustion Carbon Dioxide Capture: An Opportunity for Membranes J. Membr. Sci. 2010, 359, 126-139
82. Le, N. L.; Wang, Y.; Chung, T. S. Synthesis, Cross-Linking Modifications of 6FDA-NDA/DABA Polyimide Membranes for Ethanol Dehydration via Pervaporation J. Membr. Sci. 2012, 416, 109-121
83. 2 Capture J. Membr. Sci. 2013, 436, 221-231