Mass transport mechanisms within pervaporation membranes

Abstract

Pervaporation is an energy-efficient membrane technology for separating liquid molecules of similar physical properties, which may compete or combine with distillation separation technology in a number of applications. With the rapid development of new membrane materials, the pervaporation performance was significantly improved. Fundamental understanding of the mass transport mechanisms is crucial for the rational design of membrane materials and efficient intensification of pervaporation process. Based on the interactions between permeate molecules and membranes, this review focuses on two categories of mass transport mechanisms within pervaporation membranes: physical mechanism (solution-diffusion mechanism, molecular sieving mechanism) and chemical mechanism (facilitated transport mechanism). Furthermore, the optimal integration and evolution of different mass transport mechanisms are briefly introduced. Material selection and relevant applications are highlighted under the guidance of mass transport mechanisms. Finally, the current challenges and future perspectives are tentatively identified.

Keywords

pervaporation membrane / mass transport mechanisms / physical mechanism / chemical mechanism

参考文献

[1] Sholl D S, Lively R P. Seven chemical separations to change the world. Nature, 2016, 532(7600): 435–437

[2] Shao P, Huang R Y M. Polymeric membrane pervaporation. Journal of Membrane Science, 2007, 287(2): 162–179

[3] Ong Y K, Shi G M, Le N L, Tang Y P, Zuo J, Nunes S P, Chung T S. Recent membrane development for pervaporation processes. Progress in Polymer Science, 2016, 57: 1–31

[4] Zhao J, Jin W Q. Manipulation of confined structure in alcohol-permselective pervaporation membranes. Chinese Journal of Chemical Engineering, 2017, 25(11): 1616–1626

[5] Cao L, He X Y, Jiang Z Y, Li X Q, Li Y F, Ren Y X, Yang L X, Wu H. Channel-facilitated molecule and ion transport across polymer composite membranes. Chemical Society Reviews, 2017, 46(22): 6725–6745

[6] Wang J W, Dlamini D S, Mishra A K, Pendergast M T M, Wong M C Y, Mamba B B, Freger V, Verliefde A R D, Hoek E M V. A critical review of transport through osmotic membranes. Journal of Membrane Science, 2014, 454: 516–537

[7] Koros W J, Zhang C. Materials for next-generation molecularly selective synthetic membranes. Nature Materials, 2017, 16(3): 289–297

[8] Chapman P D, Oliveira T, Livingston A G, Li K. Membranes for the dehydration of solvents by pervaporation. Journal of Membrane Science, 2008, 318(1-2): 5–37

[9] Jiang L Y, Wang Y, Chung T S, Qiao X Y, Lai J Y. Polyimides membranes for pervaporation and biofuels separation. Progress in Polymer Science, 2009, 34(11): 1135–1160

[10] Zhao Q, An Q F, Ji Y L, Qian J W, Gao C J. Polyelectrolyte complex membranes for pervaporation, nanofiltration and fuel cell applications. Journal of Membrane Science, 2011, 379(1-2): 19–45

[11] Liu G P, Jin W Q, Xu N P. Graphene-based membranes. Chemical Society Reviews, 2015, 44(15): 5016–5030

[12] Li X, Liu Y X, Wang J, Gascon J, Li J S, Van der Bruggen B. Metal-organic frameworks based membranes for liquid separation. Chemical Society Reviews, 2017, 46(23): 7124–7144

[13] Cheng X X, Pan F S, Wang M R, Li W D, Song Y M, Liu G H, Yang H, Gao B X, Wu H, Jiang Z Y. Hybrid membranes for pervaporation separations. Journal of Membrane Science, 2017, 541: 329–346

[14] Smitha B, Suhanya D, Sridhar S, Ramakrishna M. Separation of organic-organic mixtures by pervaporation: A review. Journal of Membrane Science, 2004, 241(1): 1–21

[15] Zhang C, Peng L, Jiang J, Gu X H. Mass transfer model, preparation and applications of zeolite membranes for pervaporation dehydration: A review. Chinese Journal of Chemical Engineering, 2017, 25(11): 1627–1638

[16] Wang J, Zhu S, Xu C. Biochemistry. 3rd ed. Beijing: High Education Press, 2002, 1: 201–202

[17] Espinosa E, Molins E, Lecomte C. Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities. Chemical Physics Letters, 1998, 285(3-4): 170–173

[18] Némethy G. Hydrophobic interactions. Angewandte Chemie International Edition, 1967, 6(3): 195–206

[19] Wijmans J G, Baker R W. The solution-diffusion model: A review. Journal of Membrane Science, 1995, 107(1-2): 1–21

[20] Hansen C M. Hansen Solubility Parameters: A User’s Handbook. Florida: CRC Press, 2007, 4–17

[21] Lodge T P. Reconciliation of the molecular weight dependence of diffusion and viscosity in entangled polymers. Physical Review Letters, 1999, 83(16): 3218–3221

[22] George S C, Thomas S. Transport phenomena through polymeric systems. Progress in Polymer Science, 2001, 26(6): 985–1017

[23] Wu X M, Guo H, Soyekwo F, Zhang Q G, Lin C X, Liu Q L, Zhu A M. Pervaporation purification of ethylene glycol using the highly permeable PIM-1 membrane. Journal of Chemical & Engineering Data, 2016, 61(1): 579–586

[24] Chen M M, Wu X M, Soyekwo F, Zhang Q G, Lv R X, Zhu A M, Liu Q L. Toward improved hydrophilicity of polymers of intrinsic microporosity for pervaporation dehydration of ethylene glycol. Separation and Purification Technology, 2017, 174: 166–173

[25] Grimaldi J, Imbrogno J, Kilduff J, Belfort G. New class of synthetic membranes: Organophilic pervaporation brushes for organics recovery. Chemistry of Materials, 2015, 27(11): 4142–4148

[26] Xu Y M, Tang Y P, Chung T S, Weber M, Maletzko C. Polyarylether membranes for dehydration of ethanol and methanol via pervaporation. Separation and Purification Technology, 2018, 193: 165–174

[27] Bofinger A, Drake J A. Preferential permeability of methanol into water using polysilicone and poly(1-trimethylsilyl-1-propyne) membranes. Journal of Membrane Science, 2006, 285(1-2): 282–289

[28] Du N Y, Park H B, Robertson G P, Dal-Cin M M, Visser T, Scoles L, Guiver M D. Polymer nanosieve membranes for CO₂-capture applications. Nature Materials, 2011, 10(5): 372–375

[29] Tan L X, Tan B. Hypercrosslinked porous polymer materials: Design, synthesis, and applications. Chemical Society Reviews, 2017, 46(11): 3322–3356

[30] Tang Y P, Wang H, Chung T S. Towards high water permeability in triazine-framework-based microporous membranes for dehydration of ethanol. ChemSusChem, 2015, 8(1): 138–147

[31] Xu Y M, Japip S, Chung T S. Mixed matrix membranes with nano-sized functional UiO-66-type MOFs embedded in 6FDA-HAB/DABA polyimide for dehydration of C1-C3 alcohols via pervaporation. Journal of Membrane Science, 2018, 549: 217–226

[32] Zhao J, Zhao X T, Jiang Z Y, Li Z, Fan X C, Zhu J N, Wu H, Su Y L, Yang D, Pan F S, Shi J. Biomimetic and bioinspired membranes: Preparation and application. Progress in Polymer Science, 2014, 39(9): 1668–1720

[33] Yang H, Wu H, Yao Z Q, Shi B B, Xu Z, Cheng X X, Pan F S, Liu G H, Jiang Z Y, Cao X Z. Functionally graded membranes from nanoporous covalent organic frameworks for highly selective water permeation. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2018, 6(2): 583–591

[34] Liu G H, Jiang Z Y, Cao K T, Nair S, Cheng X X, Zhao J, Gomaa H, Wu H, Pan F S. Pervaporation performance comparison of hybrid membranes filled with two-dimensional ZIF-L nanosheets and zero-dimensional ZIF-8 nanoparticles. Journal of Membrane Science, 2017, 523: 185–196

[35] Wang M R, Xing R S, Wu H, Pan F S, Zhang J J, Ding H, Jiang Z Y. Nanocomposite membranes based on alginate matrix and high loading of pegylated POSS for pervaporation dehydration. Journal of Membrane Science, 2017, 538: 86–95

[36] Ben T, Ren H, Ma S Q, Cao D P, Lan J H, Jing X F, Wang W C, Xu J, Deng F, Simmons J M, et al. Targeted synthesis of a porous aromatic framework with high stability and exceptionally high surface area. Angewandte Chemie International Edition, 2009, 48(50): 9457–9460

[37] Zou X Q, Zhu G S. Microporous organic materials for membrane-based gas separation. Advanced Materials, 2018, 30(3): 17000750

[38] Cheng X Q, Konstas K, Doherty C M, Wood C D, Mulet X, Xie Z L, Ng D, Hill M R, Lau C H, Shao L. Organic microporous nanofillers with unique alcohol affinity for superior ethanol recovery toward sustainable biofuels. ChemSusChem, 2017, 10(9): 1887–1891

[39] Zhang K, Lively R P, Zhang C, Chance R R, Koros W J, Sholl D S, Nair S. Exploring the framework hydrophobicity and flexibility of ZIF-8: From biofuel recovery to hydrocarbon separations. Journal of Physical Chemistry Letters, 2013, 4(21): 3618–3622

[40] Zhang K, Lively R P, Zhang C, Koros W J, Chance R R. Investigating the intrinsic ethanol/water separation capability of ZIF-8: An adsorption and diffusion study. Journal of Physical Chemistry C, 2013, 117(14): 7214–7225

[41] Wee L H, Li Y, Zhang K, Davit P, Bordiga S, Jiang J, Vankelecom I F J, Martens J A. Submicrometer-sized ZIF-71 filled organophilic membranes for improved bioethanol recovery: Mechanistic in-sights by Monte Carlo simulation and FTIR spectroscopy. Advanced Functional Materials, 2015, 25(4): 516–525

[42] Liu X L, Li Y S, Zhu G Q, Ban Y J, Xu L Y, Yang W S. An organophilic pervaporation membrane derived from metal-organic framework nanoparticles for efficient recovery of bio-alcohols. Angewandte Chemie International Edition, 2011, 50(45): 10636–10639

[43] Fan H, Qi S, Hao Y, Ji S, Dong J, Zhang G. Simultaneous spray self-assembly of highly loaded ZIF-8-PDMS nanohybrid membranes exhibiting exceptionally high biobutanol-permselective pervaporation. Angewandte Chemie International Edition, 2014, 53(22): 5578–5582

[44] Sukitpaneenit P, Chung T S, Jiang L Y. Modified pore-flow model for pervaporation mass transport in PVDF hollow fiber membranes for ethanol-water separation. Journal of Membrane Science, 2010, 362(1-2): 393–406

[45] Zhang Y L, Benes N E, Lammertink R G H. Performance study of pervaporation in a microfluidic system for the removal of acetone from water. Chemical Engineering Journal, 2016, 284: 1342–1347

[46] Yong W F, Salehian P, Zhang L L, Chung T S. Effects of hydrolyzed PIM-1 in polyimide-based membranes on C2-C4 alcohols dehydration via pervaporation. Journal of Membrane Science, 2017, 523: 430–438

[47] Friess K, Jansen J C, Vopička O, Randová A, Hynek V, Šípek M, Bartovská L, Izák P, Dingemans M, Dewulf J, et al. Comparative study of sorption and permeation techniques for the determination of heptane and toluene transport in polyethylene membranes. Journal of Membrane Science, 2009, 338(1): 161–174

[48] Liu L, Kentish S E. Pervaporation performance of crosslinked PVA membranes in the vicinity of the glass transition temperature. Journal of Membrane Science, 2018, 553: 63–69

[49] Mulder M. Thermodynamic Principles of Pervaporation: Pervaporation Membrane Separation Processes. Amsterdam: Elsevier, 1991, 225–250

[50] Dawiec A, Witek-Krowiak A, Podstawczyk D, Pokomeda K. Mathematical modeling of sorption step in pervaporative aroma compounds recovery from the multicomponent solution. Chemical Engineering Science, 2015, 129: 78–90

[51] Jain M, Attarde D, Gupta S K. Removal of thiophene from n-heptane/thiophene mixtures by spiral wound pervaporation module: Modelling, validation and influence of operating conditions. Journal of Membrane Science, 2015, 490: 328–345

[52] Genduso G, Farrokhzad H, Latre Y, Darvishmanesh S, Luis P, Van der Bruggen B. Polyvinylidene fluoride dense membrane for the pervaporation of methyl acetate-methanol mixtures. Journal of Membrane Science, 2015, 482: 128–136

[53] Elyassi B, Jeon M Y, Tsapatsis M, Narasimharao K, Basahel S N, Thabaiti S. Ethanol/water mixture pervaporation performance of b-oriented silicalite-1 membranes made by gel-free secondary growth. AIChE Journal. American Institute of Chemical Engineers, 2016, 62(2): 556–563

[54] Ashraf M T, Schmidt J E, Kujawa J, Kujawski W, Arafat H A. One-dimensional modeling of pervaporation systems using a semi-empirical flux model. Separation and Purification Technology, 2017, 174: 502–512

[55] Kapteijn F, Moulijn J A, Krishna R. The generalized Maxwell-Stefan model for diffusion in zeolites: Sorbate molecules with different saturation loadings. Chemical Engineering Science, 2000, 55(15): 2923–2930

[56] Lipnizki F, Tragardh G. Modelling of pervaporation: Models to analyze and predict the mass transport in pervaporation. Separation and Purification Methods, 2001, 30(1): 49–125

[57] Mafi A, Raisi A, Hatam M, Aroujalian A. A mathematical model for mass transfer in hydrophobic pervaporation for organic compounds separation from aqueous solutions. Journal of Membrane Science, 2012, 423-424(12): 175–188

[58] Feng H D. Modeling of vapor sorption in glassy polymers using a new dual mode sorption model based on multilayer sorption theory. Polymer, 2007, 48(10): 2988–3002

[59] Ye P, Zhang Y, Wu H, Gu X. Mass transfer simulation on pervaporation dehydration of ethanol through hollow fiber NaA zeolite membranes. AIChE Journal. American Institute of Chemical Engineers, 2016, 62(7): 2468–2478

[60] Ebneyamini A, Azimi H, Tezel F H, Thibault J. Modelling of mixed matrix membranes: Validation of the resistance-based model. Journal of Membrane Science, 2017, 543: 361–369

[61] Shieh J J, Huang R Y M. A pseudophase-change solution-diffusion model for pervaporation. II. Binary mixture permeation. Separation Science and Technology, 1998, 33(7): 933–957

[62] Pera T M, Fite C, Sebastian V, Lorente E, Llorens J, Cunill F. Modeling pervaporation of ethanol/water mixtures within ‘Real’ zeolite NaA membranes. Industrial & Engineering Chemistry Research, 2008, 47(9): 3213–3224

[63] Zhang W Y, Na S S, Li W X, Xing W H. Kinetic modeling of pervaporation aided esterification of propionic acid and ethanol using T-type zeolite membrane. Industrial & Engineering Chemistry Research, 2015, 54(18): 4940–4946

[64] Krishna R. Describing mixture permeation across polymeric membranes by a combination of Maxwell-Stefan and Flory-Huggins models. Polymer, 2016, 103: 124–131

[65] Zhuang X, Chen X, Su Y, Luo J, Feng S, Zhou H, Wan Y. Surface modification of silicalite-1 with alkoxysilanes to improve the performance of PDMS/silicalite-1 pervaporation membranes: Preparation, characterization and modeling. Journal of Membrane Science, 2016, 499: 386–395

[66] Wang L D, Boutilier M S H, Kidambi P R, Jang D, Hadjiconstantinou N G, Karnik R. Fundamental transport mechanisms, fabrication and potential applications of nanoporous atomically thin membranes. Nature Nanotechnology, 2017, 12(6): 509–522

[67] Gao X C, Ji G Z, Wang J C, Peng L, Gu X H, Chen L. Critical pore dimensions for gases in a BTESE-derived organic-inorganic hybrid silica: A theoretical analysis. Separation and Purification Technology, 2018, 191: 27–37

[68] Choi M, Na K, Kim J, Sakamoto Y, Terasaki O, Ryoo R. Stable single-unit-cell nanosheets of zeolite MFI as active and long-lived catalysts. Nature, 2009, 461(7261): 246–249

[69] Sekulic J, Elshof J E, Blank D H A. A microporous titania membrane for nanofiltration and pervaporation. Advanced Materials, 2004, 16(17): 1546–1550

[70] Pera T M. Porous inorganic membranes for CO₂ capture: Present and prospects. Chemical Reviews, 2014, 114(2): 1413–1492

[71] Nishibayashi M, Yoshida H, Uenishi M, Kanezashi M, Nagasawa H, Yoshioka T, Tsuru T. Photo-induced sol-gel processing for low-temperature fabrication of high-performance silsesquioxane membranes for use in molecular separation. Chemical Communications, 2015, 51(49): 9932–9935

[72] Araki S, Okabe A, Ogawa A, Gondo D, Imasaka S, Hasegawa Y, Sato K, Li K, Yamamoto H. Preparation and pervaporation performance of vinyl-functionalized silica membranes. Journal of Membrane Science, 2018, 548: 66–72

[73] Jeon M Y, Kim D, Kumar P, Lee P S, Rangnekar N, Bai P, Shete M, Elyassi B, Lee H S, Narasimharao K, et al. Ultra-selective high-flux membranes from directly synthesized zeolite nanosheets. Nature, 2017, 543(7647): 690–694

[74] Kim D, Jeon M Y, Stottrup B L, Tsapatsis M. para-Xylene ultra-selective zeolite MFI membranes fabricated from nanosheet monolayers at the air-water interface. Angewandte Chemie International Edition, 2018, 57(2): 480–485

[75] Furukawa H, Gandara F, Zhang Y B, Jiang J C, Queen W L, Hudson M R, Yaghi O M. Water adsorption in porous metal-organic frameworks and related materials. Journal of the American Chemical Society, 2014, 136(11): 4369–4381

[76] Wu F C, Lin L, Liu H O, Wang H T, Qiu J S, Zhang X F. Synthesis of stable UiO-66 membranes for pervaporation separation of methanol/methyl tert-butyl ether mixtures by secondary growth. Journal of Membrane Science, 2017, 544: 342–350

[77] Liu X L, Wang C H, Wang B, Li K. Novel organic-dehydration membranes prepared from zirconium metal-organic frameworks. Advanced Functional Materials, 2017, 27(3): 1604311

[78] Ibrahim A, Lin Y S. Pervaporation separation of organic mixtures by MOF-5 membranes. Industrial & Engineering Chemistry Research, 2016, 55(31): 8652–8658

[79] Liu G, Jin W, Xu N. Two-dimensional-material membranes: A new family of high-performance separation membranes. Angewandte Chemie International Edition, 2016, 55(43): 13384–13397

[80] Kommu A, Singh J K. Separation of ethanol and water using graphene and hexagonal boron nitride slit pores: A molecular dynamics study. Journal of Physical Chemistry C, 2017, 121(14): 7867–7880

[81] Yoon Y, Lee K, Kwon S, Seo S, Yoo H, Kim S, Shin Y, Park Y, Kim D, Choi J Y, Lee H. Vertical alignments of graphene sheets spatially and densely piled for fast ion diffusion in compact supercapacitors. ACS Nano, 2014, 8(5): 4580–4590

[82] Huang K, Liu G, Lou Y, Dong Z, Shen J, Jin W. A graphene oxide membrane with highly selective molecular separation of aqueous organic solution. Angewandte Chemie International Edition, 2014, 53(27): 7049–7052

[83] Liu G Z, Shen J, Liu Q, Liu G P, Xiong J, Yang J, Jin W Q. Ultrathin two-dimensional MXene membrane for pervaporation desalination. Journal of Membrane Science, 2018, 548: 548–558

[84] Joshi R K, Carbone P, Wang F C, Kravets V G, Su Y, Grigorieva I V, Wu H A, Geim A K, Nair R R. Precise and ultrafast molecular sieving through graphene oxide membranes. Science, 2014, 343(6172): 752–754

[85] Tsou C H, An Q F, Lo S C, De G M, Hung W S, Hu C C, Lee K R, Lai J Y. Effect of microstructure of graphene oxide fabricated through different self-assembly techniques on 1-butanol dehydration. Journal of Membrane Science, 2015, 477: 93–100

[86] Qi B Y, He X F, Zeng G F, Pan Y C, Li G H, Liu G J, Zhang Y F, Chen W, Sun Y H. Strict molecular sieving over electrodeposited 2D-interspacing-narrowed graphene oxide membranes. Nature Communications, 2017, 8(825): 1–10

[87] Wan J Y, Lacey S D, Dai J Q, Bao W Z, Fuhrer M S, Hu L B. Tuning two-dimensional nanomaterials by intercalation: Materials, properties and applications. Chemical Society Reviews, 2016, 45(24): 6742–6765

[88] Chen L, Shi G S, Shen J, Peng B Q, Zhang B W, Wang Y Z, Bian F G, Wang J J, Li D Y, Qian Z, et al. Ion sieving in graphene oxide membranes via cationic control of interlayer spacing. Nature, 2017, 550(7676): 380–383

[89] Hung W S, Tsou C H, De G M, An Q F, Liu Y L, Zhang Y M, Hu C C, Lee K R, Lai J Y. Cross-linking with diamine monomers to prepare composite graphene oxide-framework membranes with varying d-spacing. Chemistry of Materials, 2014, 26(9): 2983–2990

[90] Yang J J, Gong D A, Li G H, Zeng G F, Wang Q Y, Zhang Y L, Liu G J, Wu P, Vovk E, Peng Z, et al. Self-assembly of thiourea-crosslinked graphene oxide framework membranes toward separation of small molecules. Advanced Materials, 2018, 30(16): 1705775

[91] Li Y, Wang S, He G, Wu H, Pan F, Jiang Z. Facilitated transport of small molecules and ions for energy-efficient membranes. Chemical Society Reviews, 2015, 44(1): 103–118

[92] Cussler E L, Aris R, Bhown A. On the limits of facilitated diffusion. Journal of Membrane Science, 1989, 43(2): 149–164

[93] Kim H S, Kim Y J, Kim J J, Lee S D, Kang Y S, Chin C S. Spectroscopic characterization of cellulose acetate polymer membranes containing Cu(1,3-butadiene)OTf as a facilitated olefin transport carrier. Chemistry of Materials, 2001, 13(5): 1720–1725

[94] Hernandez M A J, Yang R T. Desulfurization of diesel fuels via π-complexation with nickel(II)-exchanged X- and Y-zeolites. Industrial & Engineering Chemistry Research, 2004, 43(4): 1081–1089

[95] Yang Z J, Zhang W, Wang T, Li J D. Improved thiophene solution selectivity by Cu²⁺, Pb²⁺ and Mn²⁺ ions in pervaporative poly bis(p-methyl phenyl) phosphazene desulfurization membrane. Journal of Membrane Science, 2014, 454: 463–469

[96] Takahashi A, Yang F H, Yang R T. New sorbents for desulfurization by π-complexation: Thiophene/benzene adsorption. Industrial & Engineering Chemistry Research, 2002, 41(10): 2487–2496

[97] Safarik D J, Eldridge R B. Olefin/paraffin separations by reactive absorption: A review. Industrial & Engineering Chemistry Research, 1998, 37(7): 2571–2581

[98] Yang R T. Adsorbents: Fundamentals and Applications. New Jersey: John Wiley & Sons, 2003, 191–193

[99] Martinez S, Valek L, Oslakovic I S. Adsorption of organic anions on low-carbon steel in saturated Ca(OH)₂ and the HSAB principle. Journal of the Electrochemical Society, 2007, 154(11): 671–677

[100] Li W, Pan F, Song Y, Wang M, Wang H, Walker S, Wu H, Jiang Z. Construction of molecule-selective mixed matrix membranes with confined mass transfer structure. Chinese Journal of Chemical Engineering, 2017, 25(11): 1563–1580

[101] Kang Y S, Kang S W, Kim H, Kim J H, Won J, Kim C K, Char K. Interaction with olefins of the partially polarized surface of silver nanoparticles activated by p-benzoquinone and its implications for facilitated olefin transport. Advanced Materials, 2007, 19(3): 475–479

[102] Tranchemontagne D J L, Ni Z, O’Keeffe M, Yaghi O M. Reticular chemistry of metal-organic polyhedra. Angewandte Chemie International Edition, 2008, 47(28): 5136–5147

[103] Zhou L, Dai X Q, Du J J, Wang T, Wu L G, Tang Y C, Shen J. Fabrication of poly(MMA-co-ST) hybrid membranes containing AgCl nanoparticles by in situ ionic liquid microemulsion polymerization and enhancement of their separation performance. Industrial & Engineering Chemistry Research, 2015, 54(13): 3326–3332

[104] Wu F, Cao Y, Liu H, Zhang X. High-performance UiO-66-NH₂ tubular membranes by zirconia-induced synthesis for desulfurization of model gasoline via pervaporation. Journal of Membrane Science, 2018, 556: 54–65

[105] Li B, Xu D, Jiang Z Y, Zhang X F, Liu W P, Dong X A. Pervaporation performance of PDMS-Ni²⁺Y zeolite hybrid membranes in the desulfurization of gasoline. Journal of Membrane Science, 2008, 322(2): 293–301

[106] Yu S N, Pan F S, Yang S, Ding H, Jiang Z Y, Wang B Y, Li Z X, Cao X Z. Enhanced pervaporation performance of MIL-101 (Cr) filled polysiloxane hybrid membranes in desulfurization of model gasoline. Chemical Engineering Science, 2015, 135: 479–488

[107] Zhang Y, Wang N X, Zhao C, Wang L, Ji S L, Li J R. Co(HCOO)(2)-based hybrid membranes for the pervaporation separation of aromatic/aliphatic hydrocarbon mixtures. Journal of Membrane Science, 2016, 520: 646–656

[108] Zhao C, Wang N X, Wang L, Huang H L, Zhang R, Yang F, Xie Y B, Ji S L, Li J R. Hybrid membranes of metal-organic molecule nanocages for aromatic/aliphatic hydrocarbon separation by pervaporation. Chemical Communications, 2014, 50(90): 13921–13923

[109] Zhao C, Wang N X, Wang L, Sheng S N, Fan H W, Yang F, Ji S L, Li J R, Yu J M. Functionalized metal-organic polyhedra hybrid membranes for aromatic hydrocarbons recovery. AIChE Journal. American Institute of Chemical Engineers, 2016, 62(10): 3706–3716

[110] Pan F S, Wang M D, Ding H, Song Y M, Li W D, Wu H, Jiang Z Y, Wang B Y, Cao X Z. Embedding Ag⁺@COFs within Pebax membrane to confer mass transport channels and facilitated transport sites for elevated desulfurization performance. Journal of Membrane Science, 2018, 552: 1–12

[111] Lee H, Dellatore S M, Miller W M, Messersmith P B. Mussel-inspired surface chemistry for multifunctional coatings. Science, 2007, 318(5849): 426–430

[112] Liu W P, Li B, Cao R J, Jiang Z Y, Yu S N, Liu G H, Wu H. Enhanced pervaporation performance of poly(dimethyl siloxane) membrane by incorporating titania microspheres with high silver ion loading. Journal of Membrane Science, 2011, 378(1-2): 382–392

[113] Liu G, Zhou T, Liu W, Hu S, Pan F, Wu H, Jiang Z, Wang B, Yang J, Cao X. Enhanced desulfurization performance of PDMS membranes by incorporating silver decorated dopamine nanoparticles. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2014, 2(32): 12907–12917

[114] Yu S N, Jiang Z Y, Yang S, Ding H, Zhou B F, Gu K, Yang D, Pan F S, Wang B Y, Wang S, Cao X. Highly swelling resistant membranes for model gasoline desulfurization. Journal of Membrane Science, 2016, 514: 440–449

[115] Janiak C.A critical account on π-π stacking in metal complexes with aromatic nitrogen-containing ligands. Journal of the Chemical Society-Dalton Transactions, 2000(21): 3885–3896

[116] Hunter C A, Sanders J K M. The nature of π-π interactions. Journal of the American Chemical Society, 1990, 112(14): 5525–5534

[117] Sha S, Kong Y, Yang J R. The pervaporation performance of C-60-filled ethyl cellulose hybrid membrane for gasoline desulfurization: Effect of operating temperature. Energy & Fuels, 2012, 26(11): 6925–6929

[118] Wu T, Wang N X, Li J, Wang L, Zhang W, Zhang G J, Ji S L. Tubular thermal crosslinked-PEBA/ceramic membrane for aromatic/aliphatic pervaporation. Journal of Membrane Science, 2015, 486: 1–9

[119] Gulhane H, Murthy Z V P. Separation of benzene-isooctane mixtures using poly(vinyl alcohol)/graphene composite pervaporation membranes. Journal of Polymer Materials, 2017, 34(2): 439–453

[120] Wang T, Shen J N, Wu L G, Bruggen B V D. Improvement in the permeation performance of hybrid membranes by the incorporation of functional multi-walled carbon nanotubes. Journal of Membrane Science, 2014, 466(18): 338–347

[121] Pan F S, Ding H, Li W D, Song Y M, Yang H, Wu H, Jiang Z Y, Wang B Y, Cao X Z. Constructing facilitated transport pathway in hybrid membranes by incorporating MoS₂ nanosheets. Journal of Membrane Science, 2018, 545: 29–37

[122] Yang H, Yuan B, Zhang X, Scherman O A. Supramolecular chemistry at interfaces: Host-guest interactions for fabricating multifunctional biointerfaces. Accounts of Chemical Research, 2014, 47(7): 2106–2115

[123] Liu J, Hua D, Zhang Y, Japip S, Chung T S. Precise molecular sieving architectures with janus pathways for both polar and nonpolar molecules. Advanced Materials, 2018, 30(11): 1705933

[124] Takaba H, Way J D. Separation of isomeric xylenes using cyclodextrin-modified ceramic membranes. Industrial & Engineering Chemistry Research, 2003, 42(6): 1243–1252

[125] Rolling P, Lamers M, Staudt C. Cross-linked membranes based on acrylated cyclodextrins and polyethylene glycol dimethacrylates for aromatic/aliphatic separation. Journal of Membrane Science, 2010, 362(1-2): 154–163

[126] Wang Y, Chung T S, Wang H. Polyamide-imide membranes with surface immobilized cyclodextrin for butanol isomer separation via pervaporation. AIChE Journal. American Institute of Chemical Engineers, 2011, 57(6): 1470–1484

[127] Van Gestel T, Barthel J. New types of graphene-based membranes with molecular sieve properties for He, H₂ and H₂O. Journal of Membrane Science, 2018, 554: 378–384

[128] Huang K, Liu G P, Shen J, Chu Z Y, Zhou H L, Gu X H, Jin W Q, Xu N P. High-efficiency water-transport channels using the synergistic effect of a hydrophilic polymer and graphene oxide laminates. Advanced Functional Materials, 2015, 25(36): 5809–5815

[129] Konios D, Stylianakis M M, Stratakis E, Kymakis E. Dispersion behaviour of graphene oxide and reduced graphene oxide. Journal of Colloid and Interface Science, 2014, 430: 108–112

[130] Yang H, Wu H, Pan F S, Li Z, Ding H, Liu G H, Jiang Z Y, Zhang P, Cao X Z, Wang B Y. Highly water-permeable and stable hybrid membrane with asymmetric covalent organic framework distribution. Journal of Membrane Science, 2016, 520: 583–595

[131] Cao K, Jiang Z, Zhang X, Zhang Y, Zhao J, Xing R, Yang S, Gao C, Pan F. Highly water-selective hybrid membrane by incorporating g-C₃N₄ nanosheets into polymer matrix. Journal of Membrane Science, 2015, 490: 72–83

[132] Kuila S B, Ray S K. Separation of benzene-cyclohexane mixtures by filled blend membranes of carboxymethyl cellulose and sodium alginate. Separation and Purification Technology, 2014, 123: 45–52

[133] Wang T, Zhao L, Chen Y F, Ding L F, Feng S, Wu L G, Wang Y X. Influence of modification of MWCNTs on the structure and performance of MWCNT-Poly (MMA-AM) hybrid membranes. Polymers for Advanced Technologies, 2014, 25(3): 288–293

[134] Zhang X L, Qian L P, Wang H T, Zhong W, Du Q G. Pervaporation of benzene/cyclohexane mixtures through rhodium-loaded beta-zeolite-filled polyvinyl chloride hybrid membranes. Separation and Purification Technology, 2008, 63(2): 434–443

[135] Yu S N, Jiang Z Y, Ding H, Pan F S, Wang B Y, Yang J, Cao X Z. Elevated pervaporation performance of polysiloxane membrane using channels and active sites of metal organic framework CuBTC. Journal of Membrane Science, 2015, 481: 73–81

[136] Majumder M, Chopra N, Andrews R, Hinds B J. Nanoscale hydrodynamics: Enhanced flow in carbon nanotubes. Nature, 2005, 438(7064): 44

[137] Sui H X, Han B G, Lee J K, Walian P, Jap B K. Structural basis of water-specific transport through the AQP1 water channel. Nature, 2001, 414(6866): 872–878

[138] Wen L, Zhang X, Tian Y, Jiang L. Quantum-confined superfluidics: From nature to artificial. Science China Materials, 2018, 61(8): 1027–1032

[139] Agre P. Aquaporin water channels (Nobel lecture). Angewandte Chemie International Edition, 2004, 43(33): 4278–4290

[140] Kofinger J, Hummer G, Dellago C. Single-file water in nanopores. Physical Chemistry Chemical Physics, 2011, 13(34): 15403–15417

[141] Horner A, Pohl P. Single-file transport of water through membrane channels. Faraday Discussions, 2018, 209: 9–33

[142] Jin W Q, Yang C. Preface to special issue of membranes and membrane processes based on confined mass transfer. Chinese Journal of Chemical Engineering, 2017, 25(11): 1551

[143] Bernardina S D, Paineau E, Brubach J B, Judeinstein P, Rouziere S, Launois P, Roy P. Water in carbon nanotubes: The peculiar hydrogen bond network revealed by Infrared spectroscopy. Journal of the American Chemical Society, 2016, 138(33): 10437–10443

[144] Sajjan A M, Kumar B K J, Kittur A A, Kariduraganavar M Y. Novel approach for the development of pervaporation membranes using sodium alginate and chitosan-wrapped multiwalled carbon nanotubes for the dehydration of isopropanol. Journal of Membrane Science, 2013, 425: 77–88

[145] Gao B X, Jiang Z Y, Zhao C H, Gomaa H, Pan F S. Enhanced pervaporative performance of hybrid membranes containing Fe₃O₄@CNT nanofillers. Journal of Membrane Science, 2015, 492: 230–241

[146] Nair R R, Wu H A, Jayaram P N, Grigorieva I V, Geim A K. Unimpeded permeation of water through helium-leak-tight graphene-based membranes. Science, 2012, 335(6067): 442–444

[147] Hung W S, An Q F, De Guzman M, Lin H Y, Huang S H, Liu W R, Hu C C, Lee K R, Lai J Y. Pressure-assisted self-assembly technique for fabricating composite membranes consisting of highly ordered selective laminate layers of amphiphilic graphene oxide. Carbon, 2014, 68: 670–677

[148] Huang K, Liu G, Lou Y, Dong Z, Shen J, Jin W. A graphene oxide membrane with highly selective molecular separation of aqueous organic solution. Angewandte Chemie International Edition, 2014, 53(27): 6929–6932

[149] Cao K, Jiang Z, Zhao J, Zhao C, Gao C, Pan F, Wang B, Cao X, Yang J. Enhanced water permeation through sodium alginate membranes by incorporating graphene oxides. Journal of Membrane Science, 2014, 469: 272–283

[150] Song Y, Jiang Z, Gao B, Wang H, Wang M, He Z, Cao X, Pan F. Embedding hydrophobic MoS₂ nanosheets within hydrophilic sodium alginate membrane for enhanced ethanol dehydration. Chemical Engineering Science, 2018, 185: 231–242

[151] Dechnik J, Gascon J, Doonan C J, Janiak C, Sumby C J. Mixed-matrix membranes. Angewandte Chemie International Edition, 2017, 56(32): 9292–9310

[152] Lively R P, Sholl D S. From water to organics in membrane separations. Nature Materials, 2017, 16(3): 276–279

[153] Herm Z R, Wiers B M, Mason J A, van Baten J M, Hudson M R, Zajdel P, Brown C M, Masciocchi N, Krishna R, Long J R. Separation of hexane isomers in a metal-organic framework with triangular channels. Science, 2013, 340(6135): 960–964

[154] Bao Z B, Chang G G, Xing H B, Krishna R, Ren Q L, Chen B L. Potential of microporous metal-organic frameworks for separation of hydrocarbon mixtures. Energy & Environmental Science, 2016, 9(12): 3612–3641

Acknowledgments

The authors are grateful for the financial support from the National Natural Science Foundation of China (Grant Nos. 21621004, 21490583, and 21576189), the State Key Laboratory of Separation Membranes and Membrane Processes (Tianjin Polytechnic University) (No. M2-201606), the National Science Fund for Distinguished Young Scholars (No. 21125627), the State Key Laboratory of Chemical Engineering (No. SKL-ChE-17B01) and the Programme of Introducing Talents of Discipline to Universities (No. B06006).

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