Recovery of free volume in PIM-1 membranes through alcohol vapor treatment
Faiz Almansour, Monica Alberto, Rupesh S. Bhavsar, Xiaolei Fan, Peter M. Budd, Patricia Gorgojo
Recovery of free volume in PIM-1 membranes through alcohol vapor treatment
Physical aging is currently a major obstacle for the commercialization of PIM-1 membranes for gas separation applications. A well-known approach to reversing physical aging effects of PIM-1 membranes at laboratory scale is soaking them in lower alcohols, such as methanol and ethanol. However, this procedure does not seem applicable at industrial level, and other strategies must be investigated. In this work, a regeneration method with alcohol vapors (ethanol or methanol) was developed to recover permeability of aged PIM-1 membranes, in comparison with the conventional soaking-in-liquid approach. The gas permeability and separation performance, before and post the regeneration methods, were assessed using a binary mixture of CO2 and CH4 (1:1, v:v). Our results show that an 8-hour methanol vapor treatment was sufficient to recover the original gas permeability, reaching a CO2 permeability>7000 barrer.
polymer of intrinsic microporosity (PIM) / PIM-1 / physical aging / gas separation / vapor-phase regeneration
[1] |
Low Z X, Budd P M, McKeown N B, Patterson D A. Gas permeation properties, physical aging, and its mitigation in high free volume glassy polymers. Chemical Reviews, 2018, 118(12): 5871–5911
CrossRef
Google scholar
|
[2] |
Budd P M, Ghanem B S, Makhseed S, McKeown N B, Msayib K J, Tattershall C E. Polymers of intrinsic microporosity (PIMs): robust, solution-processable, organic nanoporous materials. Chemical Communications, 2004, (2): 230–231
CrossRef
Google scholar
|
[3] |
Budd P M, McKeown N B, Fritsch D. Polymers of intrinsic microporosity (PIMs): high free volume polymers for membrane applications. Macromolecular Symposia, 2006, 245-246(1): 403–405
|
[4] |
Kim S, Lee Y M. Rigid and microporous polymers for gas separation membranes. Progress in Polymer Science, 2015, 43: 1–32
CrossRef
Google scholar
|
[5] |
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. Macromolecular Rapid Communications, 2011, 32(8): 631–636
CrossRef
Google scholar
|
[6] |
Mason C R, Maynard-Atem L, Heard K W J, Satilmis B, Budd P M, Friess K, Lanc MBernardŏ P, Clarizia G, Jansen J C. Enhancement of CO2 affinity in a polymer of intrinsic microporosity by amine modification. Macromolecules, 2014, 47(3): 1021–1029
CrossRef
Google scholar
|
[7] |
Bakhtin D S, Kulikov L A, Legkov S A, Khotimskiy V S, Levin I S, Borisov I L, Maksimov A L, Volkov V V, Karakhanov E A, Volkov A V. Aging of thin-film composite membranes based on PTMSP loaded with porous aromatic frameworks. Journal of Membrane Science, 2018, 554: 211–220
CrossRef
Google scholar
|
[8] |
Harms S, Rätzke K, Faupel F, Chaukura N, Budd P M, Egger W, Ravelli L. Aging and free volume in a polymer of intrinsic microporosity (PIM-1). Journal of Adhesion, 2012, 88(7): 608–619
CrossRef
Google scholar
|
[9] |
Tiwari R R, Jin J, Freeman B D, Paul D R. Physical aging, CO2 sorption and plasticization in thin films of polymer with intrinsic microporosity (PIM-1). Journal of Membrane Science, 2017, 537: 362–371
CrossRef
Google scholar
|
[10] |
Nagai K, Nakagawa T. Effects of aging on the gas permeability and solubility in poly(1-trimethylsilyl-1-propyne) membranes synthesized with various catalysts. Journal of Membrane Science, 1995, 105(3): 261–272
CrossRef
Google scholar
|
[11] |
Jue M L, McKay C S, McCool B A, Finn M G, Lively R P. Effect of nonsolvent treatments on the microstructure of PIM-1. Macromolecules, 2015, 48(16): 5780–5790
CrossRef
Google scholar
|
[12] |
Swaidan R, Ghanem B, Litwiller E, Pinnau I. Physical aging, plasticization and their effects on gas permeation in “rigid” polymers of intrinsic microporosity. Macromolecules, 2015, 48(18): 6553–6561
CrossRef
Google scholar
|
[13] |
Budd P M, McKeown N B, Ghanem B S, Msayib K J, Fritsch D, Starannikova L, Belov N, Sanfirova O, Yampolskii Y, Shantarovich V. Gas permeation parameters and other physicochemical properties of a polymer of intrinsic microporosity: polybenzodioxane PIM-1. Journal of Membrane Science, 2008, 325(2): 851–860
CrossRef
Google scholar
|
[14] |
Bushell A F, Attfield M P, Mason C R, Budd P M, Yampolskii Y, Starannikova L, Rebrov A, Bazzarelli F, Bernardo P, Carolus Jansen J, Lanč M, Friess K, Shantarovich V, Gustov V, Isaeva V. Gas permeation parameters of mixed matrix membranes based on the polymer of intrinsic microporosity PIM-1 and the zeolitic imidazolate framework ZIF-8. Journal of Membrane Science, 2013, 427: 48–62
CrossRef
Google scholar
|
[15] |
Carta M, Malpass-Evans R, Croad M, Rogan Y, Jansen J C, Bernardo P, Bazzarelli F, McKeown N B. An efficient polymer molecular sieve for membrane gas separations. Science, 2013, 339(6117): 303–307
CrossRef
Google scholar
|
[16] |
Carta M, Croad M, Malpass-Evans R, Jansen J C, Bernardo P, Clarizia G, Friess K, Lanč M, McKeown N B. Triptycene induced enhancement of membrane gas selectivity for microporous Tröger’s base polymers. Advanced Materials, 2014, 26(21): 3526–3531
CrossRef
Google scholar
|
[17] |
Rose I, Carta M, Malpass-Evans R, Ferrari M C, Bernardo P, Clarizia G, Jansen J C, McKeown N B. Highly permeable benzotriptycene-based polymer of intrinsic microporosity. ACS Macro Letters, 2015, 4(9): 912–915
CrossRef
Google scholar
|
[18] |
Ma X, Mukaddam M, Pinnau I. Bifunctionalized intrinsically microporous polyimides with simultaneously enhanced gas permeability and selectivity. Macromolecular Rapid Communications, 2016, 37(11): 900–904
CrossRef
Google scholar
|
[19] |
Song Q, Cao S, Pritchard R H, Ghalei B, Al-Muhtaseb S A, Terentjev E M, Cheetham A K, Sivaniah E. Controlled thermal oxidative crosslinking of polymers of intrinsic microporosity towards tunable molecular sieve membranes. Nature Communications, 2014, 5(1): 4813
CrossRef
Google scholar
|
[20] |
Li F Y, Chung T S. Physical aging, high temperature and water vapor permeation studies of UV-rearranged PIM-1 membranes for advanced hydrogen purification and production. International Journal of Hydrogen Energy, 2013, 38(23): 9786–9793
CrossRef
Google scholar
|
[21] |
Alberto M, Bhavsar R, Luque-Alled J M, Vijayaraghavan A, Budd P M, Gorgojo P. Impeded physical aging in PIM-1 membranes containing graphene-like fillers. Journal of Membrane Science, 2018, 563: 513–520
CrossRef
Google scholar
|
[22] |
Bhavsar R S, Mitra T, Adams D J, Cooper A I, Budd P M. Ultrahigh-permeance PIM-1 based thin film nanocomposite membranes on PAN supports for CO2 separation. Journal of Membrane Science, 2018, 564: 878–886
CrossRef
Google scholar
|
[23] |
Yong W F, Kwek K H A, Liao K S, Chung T S. Suppression of aging and plasticization in highly permeable polymers. Polymer, 2015, 77: 377–386
CrossRef
Google scholar
|
[24] |
Horn N R, Paul D R. Carbon dioxide plasticization of thin glassy polymer films. Polymer, 2011, 52(24): 5587–5594
CrossRef
Google scholar
|
[25] |
McDermott A G, Budd P M, McKeown N B, Colina C M, Runt J. Physical aging of polymers of intrinsic microporosity: a SAXS/WAXS study. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2014, 2(30): 11742–11752
CrossRef
Google scholar
|
[26] |
Hill A J, Pas S J, Bastow T J, Burgar M I, Nagai K, Toy L G, Freeman B D. Influence of methanol conditioning and physical aging on carbon spin-lattice relaxation times of poly(1-trimethylsilyl-1-propyne). Journal of Membrane Science, 2004, 243(1): 37–44
CrossRef
Google scholar
|
[27] |
Razali M, Didaskalou C, Kim J F, Babaei M, Drioli E, Lee Y M, Szekely G. Exploring and exploiting the effect of solvent treatment in membrane separations. ACS Applied Materials & Interfaces, 2017, 9(12): 11279–11289
CrossRef
Google scholar
|
[28] |
Jimenez Solomon M F, Bhole Y, Livingston A G. High flux hydrophobic membranes for organic solvent nanofiltration (OSN)—interfacial polymerization, surface modification and solvent activation. Journal of Membrane Science, 2013, 434: 193–203
CrossRef
Google scholar
|
[29] |
Gorgojo P, Jimenez-Solomon M F, Livingston A G. Polyamide thin film composite membranes on cross-linked polyimide supports: improvement of RO performance via activating solvent. Desalination, 2014, 344: 181–188
CrossRef
Google scholar
|
[30] |
Zhao Y, Yuan Q. Effect of membrane pretreatment on performance of solvent resistant nanofiltration membranes in methanol solutions. Journal of Membrane Science, 2006, 280(1): 195–201
CrossRef
Google scholar
|
[31] |
Shukla R, Cheryan M. Performance of ultrafiltration membranes in ethanol-water solutions: effect of membrane conditioning. Journal of Membrane Science, 2002, 198(1): 75–85
CrossRef
Google scholar
|
[32] |
Penha F M, Rezzadori K, Proner M C, Zanatta V, Zin G, Tondo D W, Vladimir de Oliveira J, Petrus J C C, Di Luccio M. Influence of different solvent and time of pre-treatment on commercial polymeric ultrafiltration membranes applied to non-aqueous solvent permeation. European Polymer Journal, 2015, 66: 492–501
CrossRef
Google scholar
|
[33] |
Nguyen Q T, Favre E, Ping Z H, Néel J. Clustering of solvents in membranes and its influence on membrane transport properties. Journal of Membrane Science, 1996, 113(1): 137–150
CrossRef
Google scholar
|
[34] |
Du N, Song J, Robertson G P, Pinnau I, Guiver M D. Linear high molecular weight ladder polymer via fast polycondensation of 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethylspirobisindane with 1,4-dicyanotetrafluorobenzene. Macromolecular Rapid Communications, 2008, 29(10): 783–788
|
[35] |
Satilmis B, Budd P M. Base-catalysed hydrolysis of PIM-1: amide versus carboxylate formation. RSC Advances, 2014, 4(94): 52189–52198
|
[36] |
Hao L, Liao K S, Chung T S. Photo-oxidative PIM-1 based mixed matrix membranes with superior gas separation performance. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2015, 3(33): 17273–17281
|
[37] |
Zhang L, Fang W, Jiang J. Effects of residual solvent on membrane structure and gas permeation in a polymer of intrinsic microporosity: insight from atomistic simulation. Journal of Physical Chemistry C, 2011, 115(22): 11233–11239
CrossRef
Google scholar
|
[38] |
Mitra T, Bhavsar R S, Adams D J, Budd P M, Cooper A I. PIM-1 mixed matrix membranes for gas separations using cost-effective hypercrosslinked nanoparticle fillers. Chemical Communications, 2016, 52(32): 5581–5584
CrossRef
Google scholar
|
[39] |
Abd Halim N S, Wirzal M D H, Bilad M R, Md Nordin N A H, Adi Putra Z, Sambudi N S, Mohd Yusoff A R. Improving performance of electrospun nylon 6,6 nanofiber membrane for produced water filtration via solvent vapor treatment. Polymers, 2019, 11(12): 2117
CrossRef
Google scholar
|
[40] |
Rianjanu A, Kusumaatmaja A, Suyono E A, Triyana K. Solvent vapor treatment improves mechanical strength of electrospun polyvinyl alcohol nanofibers. Heliyon, 2018, 4(4): e00592
CrossRef
Google scholar
|
[41] |
Brunetti A, Cersosimo M, Kim J S, Dong G, Fontananova E, Lee Y M, Drioli E, Barbieri G. Thermally rearranged mixed matrix membranes for CO2 separation: an aging study. International Journal of Greenhouse Gas Control, 2017, 61: 16–26
CrossRef
Google scholar
|
[42] |
Bernardo P, Bazzarelli E, Tasselli F, Clarizia G, Mason C R, Maynard-Atem L, Budd P M, Lanc M, Pilnacek K, Vopicka O, Friess K, Fritsch D, Yampolskii Y P, Shantarovich V, Jansen J C. Effect of physical aging on the gas transport and sorption in PIM-1 membranes. Polymer, 2017, 113: 283–294
CrossRef
Google scholar
|
[43] |
Scholes C A, Kanehashi S. Polymer of intrinsic microporosity (PIM-1) membranes treated with supercritical CO2. Membranes, 2019, 9(3): 1–12
CrossRef
Google scholar
|
[44] |
Adymkanov S V, Yampol’skii Y P, Polyakov A M, Budd P M, Reynolds K J, McKeown N B, Msayib K J. Pervaporation of alcohols through highly permeable PIM-1 polymer films. Polymer Science, Series A, 2008, 50(4): 444–450
CrossRef
Google scholar
|
[45] |
Robeson L M. The upper bound revisited. Journal of Membrane Science, 2008, 320(1): 390–400
CrossRef
Google scholar
|
[46] |
Robeson L M. Correlation of separation factor versus permeability for polymeric membranes. Journal of Membrane Science, 1991, 62(2): 165–185
CrossRef
Google scholar
|
[47] |
Comesaña-Gándara B, Chen J, Bezzu C G, Carta M, Rose I, Ferrari M C, Esposito E, Fuoco A, Jansen J C, McKeown N B. Redefining the Robeson upper bounds for CO2/CH4 and CO2/N2 separations using a series of ultrapermeable benzotriptycene-based polymers of intrinsic microporosity. Energy & Environmental Science, 2019, 12(9): 2733–2740
CrossRef
Google scholar
|
/
〈 | 〉 |