Membrane-based ethylene/ethane separation: The upper bound and beyond

AIChE Journal

Volumn 59, Issue 9, 2013, Pages 3475-3489

  Rungta, Meha ^a   Zhang, Chen ^a   Koros, William J ^a   Xu, Liren ^b  

^a Georgia Institute of Technology   (United States)

^b DOW CHEMICAL COMPANY   (United States)

Author keywords

Carbon molecular sieve; Ethylene ethane; Facilitated transport; Metal organic framework; Polymeric upper bound; Pyrolysis; Zeolite

Indexed keywords

CARBON MOLECULAR SIEVE; CARBON MOLECULAR SIEVE MEMBRANES; CRYOGENIC DISTILLATIONS; ETHYLENE/ETHANE SEPARATION; FACILITATED TRANSPORT; FACILITATED TRANSPORT MEMBRANES; METAL ORGANIC FRAMEWORK; UPPER BOUND;

CARBON; DISTILLATION; MOLECULAR SIEVES; ORGANIC POLYMERS; PYROLYSIS; SCALABILITY; ZEOLITES;

MEMBRANES;

EID: 84881665565     PISSN: 00011541     EISSN: 15475905     Source Type: Journal    
DOI: 10.1002/aic.14105     Document Type: Article

References (100)

1. Gottschlich R. Energy Minimization of Separation Processes using Conventional/Membrane Hybrid Systems. Washington DC: US Dept. of Energy; 1990.
2. Robinson S, Jubin R, Choate B. Materials for Separation Technology: Energy and Emmision Reduction Opportunities. Washington DC: US Dept. of Energy; 2005.
3. Eldridge RB. Olefin paraffin separation technology: a review. Ind Eng Chem Res. 1993;32:2208-2212.
4. Caballero JA, Grossmann IE, Keyvani M, Lenz ES. Design of hybrid distillation-vapor membrane separation systems. Ind Eng Chem Res. 2009;48:9151-9162.
5. Rungta M, Xu L, Koros WJ. Carbon molecular sieve dense film membranes derived from Matrimid® for ethylene/ethane separation. Carbon. 2012;50:1488-1502.
6. Baker RW. Future directions of membrane gas separation technology. Ind Eng Chem Res. 2002;41:1393-1411.
7. Ozokwelu D. Hybrid Separations/Distillation Technology: Research Opportunities for Energy and Emissions Reduction. Washington DC: US Dept. of Energy; 2005.
8. Koros WJ. Evolving beyond the thermal age of separation processes: membranes can lead the way. AIChE J. 2004;50:2326-2334.
9. Chan SS, Wang R, Chung TS, Liu Y. C-2 and C-3 hydrocarbon separations in poly(1, 5-naphthalene-2, 2′-bis(3, 4-phthalic) hexafluoropropane) diimide (6FDA-1, 5-NDA) dense membranes. J Membr Sci. 2002;210:55-64.
10. Chan SS, Chung T-S, Liu Y, Wang R. Gas and hydrocarbon (C2 and C3) transport properties of co-polyimides synthesized from 6FDA and 1, 5-NDA (naphthalene)/durene diamines. J Membr Sci. 2003;218:235-245.
11. Tanaka K, Taguchi A, Hao J, Kita H, Okamoto K. Permeation and separation properties of polyimide membranes to olefins and paraffins. J Membr Sci. 1996;121:197-207.
12. Staudt-Bickel C, Koros WJ. Olefin/paraffin gas separations with 6FDA-based polyimide membranes. J Membr Sci. 2000;170:205-214.
13. Koros WJ, Mahajan R. Pushing the limits on possibilities for large scale gas separation: which strategies? J Membr Sci. 2000;175:181-196.
14. Robeson LM. Correlation of separation factor versus permeability for polymeric membranes. J Membr Sci. 1991;62:165-185.
15. Robeson LM. The upper bound revisited. J Membr Sci. 2008;320:390-400.
16. Freeman BD. Basis of permeability/selectivity tradeoff relations in polymeric gas separation membranes. Macromolecules. 1999;32:375-380.
17. Haraya K, Obata K, Itoh N, Shndo Y, Hakuta T, Yoshitome H. Gas permeation and separation by an asymmetric polyimide hollow fiber membrane. J Membr Sci. 1989;41:23-35.
18. Barrer RM. Activated diffusion in membranes. T Faraday Soc. 1939;35:0644-0655.
19. van Amerongen GJ. The permeability of different rubbers to gases and its relation to diffusivity and solubility. J Appl Phys. 1946;17:972-985.
20. Barrer RM, Skirrow G. Transport and equilibrium phenomena in gas elastomer systems. 1. Kinetic phenomena. J Polym Sci. 1948;3:549-563.
21. van Krevelen DW. Properties of Polymers. 3rd ed. Amsterdam; The Netherlands: Elsevier Science; 1997.
22. Burns RL, Koros WJ. Defining the challenges for C3H6/C3H8 separation using polymeric membranes. J Membr Sci. 2003;211:299-309.
23. Semenova SI. Polymer membranes for hydrocarbon separation and removal. J Membr Sci. 2004;231:189-207.
24. Das M. Membranes for Olefin/Paraffin Separations [PhD thesis]. Atlanta, GA: Georgia Institute of Technology; 2009.
25. Chen CC. Thermally Crosslinked Polyimide Hollow Fiber Membranes for Natural Gas Purification [PhD thesis]. Atlanta, GA: Georgia Institute of Technology; 2011.
26. Pye DG, Hoehn HH, Panar M. Measurement of gas permeability of polymers. I. Permeabilities in constant volume/variable pressure apparatus. J Appl Polym Sci. 1976;20:1921-1931.
27. Pye DG, Hoehn HH, Panar M. Measurement of gas permeability of polymers. II. Apparatus for determination of permeabilities of mixed gases and vapors. J Appl Polym. Sci. 1976;20:287-301.
28. Ilinitch OM, Semin GL, Chertova MV, Zamaraev KI. Novel polymeric membranes for separation of hydrocarbons. J Membr Sci. 1992;66:1-8.
29. Ilinich OM, Zamaraev KI. Separation of ethylene and ethane over polyphenyleneoxides membranes: transient increase of selectivity. J Membr Sci. 1993;82:149-155.
30. Teplyakov V, Meares P. Correlationaspects of the selective gas permeabilities of polymeric materials and membranes. Gas Sep Purif. 1990;4:66-74.
31. Breck DW. Zeolite Molecular Sieves: Structure, Chemistry and Use. New York, NY: John Wiley & Sons, Inc.; 1974.
32. Petropolous JH. Mechanisms and theories for sorption and diffusion of gases in polymers. In: Paul DR, Yampol'skii YP. Polymeric Gas Separation Membranes. Boca Raton, FL: CRC Press; 1994:17-82.
33. Koros WJ, Paul DR, Huvard GS. Energetics of gas sorption in glassy polymers. Polymer. 1979;20:956-960.
34. Koros WJ, Paul DR. Design considerations for measurement of gas sorption in polymers by pressure decay. J Polym Sci Pt B. 1976;14:1903-1907.
35. Costello LM, Koros WJ. Temperature-dependence of gas sorption and transport properties in polymers: measurement and applications. Ind Eng Chem Res. 1992;31:2708-2714.
36. Brandt WW. Model calculation of the temperature dependence of small molecule diffusion in high polymers. J Phys Chem. 1959;63:1080-1084.
37. Merkel T, Blanc R, Zeid J, Suwarlim A, Firat B, Wijmans H, Asaro M, Greene M. Separation of Olefin/Paraffin Mixtures with Carrier Facilitated Membranes. Washington DC: US Dept. of Energy; 2007.
38. Faiz R, Li K. Olefin/paraffin separation using membrane based facilitated transport/chemical absorption techniques. Chem Eng Sci. 2012;73:261-284.
39. Ho WS, Dalrymple DC. Facilitated transport of olefins in Ag+-containing polymer membranes. J Membr Sci. 1994;91:13-25.
40. Ho WS, Doyle G, Savage DW, Pruett RL. Olefin separations via complexation with cuprous diketonate. Ind Eng Chem Res. 1988;27:334-337.
41. Pinnau I, Toy LG. Solid polymer electrolyte composite membranes for olefin/paraffin separation. J Membr Sci. 2001;184:39-48.
42. Azhin M, Kaghazchi T, Rahmani M. A review on olefin/paraffin separation using reversible chemical complexation technology. J Ind Eng Chem. 2008;14:622-638.
43. Singh A, Koros WJ. Significance of entropic selectivity for advanced gas separation membranes. Ind Eng Chem Res. 1996;35:1231-1234.
44. Ruthven DM. Molecular sieve separations. Chem Ing Tech. 2011;83:44-52.
45. Agarwal K, John M, Pai S, Newalkar BL, Bhargava R, Choudary NV. SAPO-34 assisted C3 separation: modeling and simulation. Microporous Mesoporous Mater. 2010;132:311-318.
46. Ruthven DM, Reyes SC. Adsorptive separation of light olefins from paraffins. Microporous Mesoporous Mater. 2007;104:59-66.
47. Karger J, Ruthven DM. Diffusion in Zeolites and other Microporous Solids. New York: John Wiley & Sons, Inc.; 1992.
48. Bloch ED, Queen WL, Krishna R, Zadrozny JM, Brown CM, Long JR. Hydrocarbon separations in a metal organic framework with open iron(II) coordination sites. Science. 2012;335:1606-1610.
49. Yang RT. Adsorbents: Fundamentals and Applications. Hoboken, NJ: John Wiley & Sons, Inc.; 2003.
50. Li K, Olson DH, Seidel J, Emge TJ, Gong H, Zeng H, Li J. Zeolitic imidazolate frameworks for kinetic separation of propane and propene. J Am Chem Soc. 2009;131:10368-10369.
51. Zhang C, Dai Y, Johnson JR, Karvan O, Koros WJ. High performance ZIF-8/6FDA-DAM mixed matrix membrane for propylene/propane separations. J Membr Sci. 2012;389:34-42.
52. Zhang C, Lively RP, Zhang K, Johnson JR, Karvan O, Koros WJ. Unexpected molecular sieving properties of zeolitic imidazolate framework-8. J Phys Chem. 2012;3:2130-2134.
53. Bae T-H, Lee JS, Qiu W, Koros WJ, Jones CW, Nair S. A high performance gas separation membrane containing submicrometer sized metal organic framework crystals. Angew Chem Int Ed. 2010;49:9863-9866.
54. Dai Y, Johnson JR, Karvan O, Sholl DS, Koros WJ. Ultem®/ZIF-8 mixed matrix hollow fiber membranes for CO2/N2 separations. J Membr Sci. 2012;401-402:76-82.
55. Ordonez MJC, Balkus KJ, Ferraris JP, Musselman IH. Molecular sieving realized with ZIF-8/Matrimid mixed-matrix membranes. J Membr Sci. 2010;361:28-37.
56. Pan Y, Lai Z. Sharp separation of C2/C3 hydrocarbon mixtures by zeolitic imidazolate framework-8 (ZIF-8) membranes synthesized in aqueous solutions. Chem Commun. 2011;47:10275.
57. Gücüyener C, van den Bergh J, Gascon J, Kapteijn F. Ethane/ethene separation turned on its head: selective ethane adsorption on the metal organic framework ZIF-7 through a gate-opening mechanism. J Am Chem Soc. 2010;132:17704-17706.
58. Chmelik C, Freude D, Bux H, Haase J. Ethene/ethane mixture diffusion in the MOF sieve ZIF-8 studied by MAS PFG NMR diffusometry. Microporous Mesoporous Mater. 2011;147:135-141.
59. Bux H, Chmelik C, van Baten JM, Krishna R, Caro J. Novel MOF-membrane for molecular sieving predicted by IR-diffusion studies and molecular modeling. Adv Mater. 2010;22:4741-4743.
60. Bux H, Chmelik C, Krishna R, Caro J. Ethene/ethane separation by the MOF membrane ZIF-8: molecular correlation of permeation, adsorption, diffusion. J Membr Sci. 2011;369:284-289.
61. Chmelik C, Bux H, Voss H, Caro J. Adsorption and diffusion: basis for molecular understanding of permeation through molecular sieve membranes. Chem Ing Tech. 2011;83:104-112.
62. Moore TT, Mahajan R, Vu DQ, Koros WJ. Hybrid membrane materials comprising organic polymers with rigid dispersed phases. AIChE J. 2004;50:311-321.
63. Díaz K, López-González M, del Castillo LF, Riande E. Effect of zeolitic imidazolate frameworks on the gas transport performance of ZIF8-poly(1, 4-phenylene ether-ether-sulfone) hybrid membranes. J Membr Sci. 2011;383:206-213.
64. Ploegmakers J, Japip S, Nijmeijer K. Mixed matrix membranes containing MOFs for ethylene/ethane separation Part A: membrane preparation and characterization. J Membr Sci. 2013;428:445-453.
65. Marsh H. Introduction to Carbon Science. London, UK: Butterworths; 1989.
66. Jenkins GM, Kawamura K. Polymeric Carbons: Carbon Fiber, Glass and Char. London, UK: Cambridge University Press; 1976.
67. Steel KM, Koros WJ. An investigation of the effects of pyrolysis parameters on gas separation properties of carbon materials. Carbon. 2005;43:1843-1856.
68. Kiyono M, Williams PJ, Koros WJ. Effect of pyrolysis atmosphere on separation performance of carbon molecular sieve membranes. J Membr Sci. 2010;359:2-10.
69. Singh-Ghosal A, Koros WJ. Air separation properties of flat sheet homogeneous pyrolytic carbon membranes. J Membr Sci. 2000;174:177-188.
70. Steel KM. Carbon Membranes for Challenging Gas Separations [PhD thesis]. Austin, TX: The University of Texas; 2000.
71. Pierson HO. Handbook of Carbon, Graphite, Diamond, and Fullerenes. New York: Noyes Publication; 1993.
72. Vu DQ. Formation and Characterization of Asymmetric Carbon Molecular Sieve and Mixed Matrix Membranes for Natural Gas Purification [PhD thesis]. Austin, TX: The University of Texas; 2001.
73. Williams PJ. Analysis of factors influencing the performance of CMS membranes for gas separation[PhD thesis]. Atlanta, GA: Georgia Institute of Technology; 2006.
74. Xu L, Rungta M, Brayden MK, Martinez MV, Stears BA, Barbay GA, Koros WJ. Olefins-selective asymmetric carbon molecular sieve hollow fiber membranes for hybrid membrane-distillation processes for olefin/paraffin separations. J Membr Sci. 2012;423-424:314-323.
75. Fuertes AB, Menendez I. Separation of hydrocarbon gas mixtures using phenolic resin-based carbon membranes. Sep Purif Technol. 2002;28:29-41.
76. Centeno TA, Vilas JL, Fuertes AB. Effects of phenolic resin pyrolysis conditions on carbon membrane performance for gas separation. J Membr Sci. 2004;228:45-54.
77. Hayashi J, Mizuta H, Yamamoto M, Kusakabe K, Morooka S, Suh SH. Separation of ethane/ethylene and propane/propylene systems with a carbonized BPDA-pp'ODA polyimide membrane. Ind Eng Chem Res. 1996;35:4176-4181.
78. Okamoto K, Kawamura S, Yoshino M, Kita H. Olefin/paraffin separation through carbonized membranes derived from an asymmetric polyimide hollow fiber membrane. Ind Eng Chem Res. 1999;38:4424-4432.
79. Suda H, Haraya K. Alkene/alkane permselectivities of a carbon molecular sieve membrane. Chem Commun. 1997:93-94.
80. Barsema JN, van der Vegt NFA, Koops GH, Wessling M. Carbon molecular sieve membranes prepared from porous fiber precursor. J Membr Sci. 2002;205:239-246.
81. Karvan O, Johnson JR, Williams PJ, Koros WJ. A pilot-scale system for carbon molecular sieve hollow fiber membrane manufacturing. Chem Eng Technol. 2013;36:53-61.
82. Xu L, Rungta M, Koros WJ. Matrimid® derived carbon molecular sieve hollow fiber membranes for ethylene/ethane separation. J Membr Sci. 2011;380:138-147.
83. Kiyono M, Williams PJ, Koros WJ. Effect of polymer precursors on carbon molecular sieve structure and separation performance properties. Carbon. 2010;48:4432-4441.
84. Grisdale RO. The properties of carbon contacts. J Appl Phys. 1953;24:1288-1296.
85. Singh R, Koros WJ. Carbon molecular sieve membrane performance tuning by dual temperature secondary oxygen doping (DTSOD). J Membr Sci. 2013;427:472-478.
86. Olson DH, Camblor MA, Villaescusa LA, Kuehl GH. Light hydrocarbon sorption properties of pure silica Si-CHA and ITQ-3 and high silica ZSM-58. Microporous Mesoporous Mater. 2004;67:27-33.
87. Dai W, Scheibe M, Li L, Guan N, Hunger M. Effect of the methanol-to-olefin conversion on the PFG NMR self-diffusivities of ethane and ethene in large-crystalline SAPO-34. J Phys Chem C. 2011;116:2469-2476.
88. Romero-Perez A, Aguilar-Armenta G. Adsorption kinetics and equilibria of carbon dioxide, ethylene, and ethane on 4A(CECA) zeolite. J Chem Eng. 2010;55:3625-3630.
89. Centeno TA, Fuertes AB. Supported carbon molecular sieve membranes based on a phenolic resin. J Membr Sci. 1999;160:201-211.
90. Stoeckli HF. Microporous carbons and their characterization: the present state of the art. Carbon. 1990;28:1-6.
91. Reid C, Sherwood TK. The Properties of Gases and Liquids: Their Estimation and Correlation. New York: Mcgraw-Hill; 1976.
92. Hirschfelder, Oakland K. Molecular Theory of Gases and Liquids. New York, NY: Wiley Interscience; 1964.
93. Teramoto M, Matsuyama H, Yamashiro T, Katayama Y. Separation of ethylene from ethane by supported liquid membranes containing silver-nitrate as a carrier. J Chem Eng. 1986;19:419-424.
94. Eriksen OI, Aksnes E, Dahl IM. Facilitated transport of ethene through nafion membranes.1. Water swollen membranes. J Membr Sci. 1993;85:89-97.
95. Tsou DT, Blachman MW, Davis JC. Silver-facilitated olefin/paraffin separation in a liquid membrane contactor system. Ind Eng Chem Res. 1994;33:3209-3216.
96. Bessarabov DG, Sanderson RD, Jacobs EP, Beckman IN. High-efficiency separation of an ethylene ethane mixture by a large-scale liquid-membrane contactor containing flat-sheet nonporous polymeric gas-separation membranes and a selective flowing-liquid absorbent. Ind Eng Chem Res. 1995;34:1769-1778.
97. Teramoto M, Matsuyama H, Yamashiro T, Okamoto S. Separation of ethylene from ethane by a flowing liquid membrane using silver-nitrate as a carrier. J Membr Sci. 1989;45:115-136.
98. Nymeijer K, Visser T, Assen R, Wessling M. Super selective membranes in gas-liquid membrane contactors for olefin/paraffin separation. J Membr Sci. 2004;232:107-114.
99. Ryu JH, Lee H, Kim YJ, Kang YS, Kim HS. Facilitated olefin transport by reversible olefin coordination to silver ions in a dry cellulose acetate membrane. Chem Eur J. 2001;7:1525-1529.
100. Kim HS, Ryu JH, Kim H, Ahn BS, Kang YS. Reversible olefin complexation by silver ions in dry poly(vinyl methyl ketone) membrane and its application to olefin/paraffin separations. Chem Commun. 2000:1261-1262.