Molecular simulation of penetration separation for ethanol/water mixtures using two-dimensional nanoweb graphynes

doi:10.1016/j.cjche.2018.02.028

Abstract

Abstract: Graphyne is expected to be a new-class of highly-efficient sieving membranes due to its controllable uniform pore structure and ultrathin single-atom thickness. Herein, we computationally investigate the permeation performance of liquid ethanol-water mixtures across polyporous two-dimensional γ-graphyne sheets. It was found that, in the mixture, ethanol with larger molecular diameter permeates faster through the graphyne pores than water. The simulations demonstrate that pristine graphynes could act as highly-efficient ethanol-permselective membranes for separation of ethanol-water mixtures, with ethanol permeability remarkably higher than conventional membranes. This separation mechanism is distinctly different from the molecular-size dependent sieving process. The stronger hydrophobic interfacial affinity between graphyne and ethanol makes ethanol molecules preferentially adsorb on graphyne surface and selectively penetrate through graphyne pores. This penetration mechanism provides new understanding of molecular transport through atomically thick two-dimensional nanoporous membranes and this work is expected to be valuable in the potential development of highly-efficient membranes for liquid-phase mixture separation.

Key words: Graphynes, Membrane separation, Ethanol/water, Molecular simulation

摘要： Graphyne is expected to be a new-class of highly-efficient sieving membranes due to its controllable uniform pore structure and ultrathin single-atom thickness. Herein, we computationally investigate the permeation performance of liquid ethanol-water mixtures across polyporous two-dimensional γ-graphyne sheets. It was found that, in the mixture, ethanol with larger molecular diameter permeates faster through the graphyne pores than water. The simulations demonstrate that pristine graphynes could act as highly-efficient ethanol-permselective membranes for separation of ethanol-water mixtures, with ethanol permeability remarkably higher than conventional membranes. This separation mechanism is distinctly different from the molecular-size dependent sieving process. The stronger hydrophobic interfacial affinity between graphyne and ethanol makes ethanol molecules preferentially adsorb on graphyne surface and selectively penetrate through graphyne pores. This penetration mechanism provides new understanding of molecular transport through atomically thick two-dimensional nanoporous membranes and this work is expected to be valuable in the potential development of highly-efficient membranes for liquid-phase mixture separation.

关键词: Graphynes, Membrane separation, Ethanol/water, Molecular simulation

Wei Zhang, Zhijun Xu, Xiaoning Yang. Molecular simulation of penetration separation for ethanol/water mixtures using two-dimensional nanoweb graphynes[J]. Chin.J.Chem.Eng., 2019, 27(2): 286-292.

Wei Zhang, Zhijun Xu, Xiaoning Yang. Molecular simulation of penetration separation for ethanol/water mixtures using two-dimensional nanoweb graphynes[J]. Chinese Journal of Chemical Engineering, 2019, 27(2): 286-292.

References

[1] U.H.F. Bunz, Y. Rubin, Y. Tobe, Polyethynylated cyclic pi-systems:scaffoldings for novel two and three-dimensional carbon networks, Chem. Soc. Rev. 28(1999) 107-119.

[2] F. Diederich, Carbon scaffolding-building acetylenic all-carbon and carbon-rich compounds, Nature 369(1994) 199-207.

[3] H.H. Wu, Q.H. Gong, D.H. Olson, J. Li, Commensurate adsorption of hydrocarbons and alcohols in microporous metal organic frameworks, Chem. Rev. 112(2012) 836-868.

[4] Y.J. Li, L. Xu, H.B. Liu, Y.L. Li, Graphdiyne and graphyne:from theoretical predictions to practical construction, Chem. Soc. Rev. 43(2014) 2572-2586.

[5] A.L. Ivanovskii, Graphynes and graphdyines, Prog. Solid State Chem. 41(2013) 1-19.

[6] E.L. Spitler, C.A. Johnson, M.M. Haley, Renaissance of annulene chemistry, Chem. Rev. 106(2016) 5344-5386.

[7] M.M. Haley, S.C. Brand, J.J. Pak, Carbon networks based on dehydrobenzoannulenes:synthesis of graphdiyne substructures, Angew. Chem. Int. Ed. Engl. 36(1997) 836-838.

[8] B. Cirera, Y.Q. Zhang, J. Bjork, S. Klyatskaya, Z. Chen, M. Ruben, J.V. Barth, F. Klappenberger, Synthesis of extended graphdiyne wires by vicinal surface templating, Nano Lett. 14(2014) 1891-1897.

[9] M. Gholami, F. Melin, R. McDonald, M.J. Ferguson, L. Echegoyen, R.R. Tykwinski, Synthesis and characterization of expanded radialenes, bisradialenes, and radiaannulenes, Angew. Chem. Int. Ed. Engl. 46(2007) 9081-9085.

[10] Q.H. Yuan, F. Ding, Formation of carbyne and graphyne on transition metal surfaces, Nanoscale 6(2014) 12727-12731.

[11] G.X. Li, Y.L. Li, H.B. Liu, Y.B. Guo, Y. Li, D. Zhu, Architecture of graphdiyne nanoscale films, Chem. Commun. 46(2010) 3256-3258.

[12] C.Y. Kuang, G. Tang, T.G. Jiu, H. Yang, H.B. Liu, B.R. Li, W.N. Luo, X.D. Li, W.J. Zhang, F.S. Lu, J.F. Fang, Y.L. Li, Highly efficient electron transport obtained by doping PCBM with graphdiyne in planar-heterojunction perovskite solar cells, Nano Lett. 15(2015) 2756-2762.

[13] N.L. Yang, Y.Y. Liu, H. Wen, Z.Y. Tang, H.J. Zhao, Y.L. Li, D. Wang, Photocatalytic properties of graphdiyne and graphene modified TiO₂:from theory to experiment, ACS Nano 7(2013) 1504-1512.

[14] H.J. Tang, C.M. Hessel, J.Y. Wang, N.L. Yang, R.Y. Yu, H.J. Zhao, D. Wang, Twodimensional carbon leading to new photoconversion processes, Chem. Soc. Rev. 43(2014) 4281-4299.

[15] Y.H. Guo, K. Jiang, B. Xu, Y.D. Xia, J. Yin, Z.G. Liu, Remarkable hydrogen storage capacity in Li-decorated graphyne:theoretical predication, J. Phys. Chem. C 116(2012) 13837-13841.

[16] H.J. Hwang, Y. Kwon, H. Lee, Thermodynamically stable calcium-decorated graphyne as a hydrogen storage medium, J. Phys. Chem. C 116(2012) 20220-20224.

[17] C.S. Huang, S.L. Zhang, H.B. Liu, Y.J. Li, G.T. Cui, Y.L. Li, Graphdiyne for high capacity and long-life lithium storage, Nano Energy 11(2015) 481-489.

[18] S.L. Zhang, H.B. Liu, C.S. Huang, G. Cui, Y.L. Li, Bulk graphdiyne powder applied for highly efficient lithium storage, Chem. Commun. 51(2015) 1834-1837.

[19] Y. Jiao, A.J. Du, S.C. Smith, Z.H. Zhu, S.Z. Qiao, H-2 purification by functionalized graphdiyne-role of nitrogen doping, J. Mater. Chem. A 3(2015) 6767-6771.

[20] Y. Jiao, A.J. Du, M. Hankel, Z.H. Zhu, V. Rudolph, S.C. Smith, Graphdiyne:a versatile nanomaterial for electronics and hydrogen purification, Chem. Commun. 47(2011) 11843-11845.

[21] S.W. Cranford, M.J. Buehler, Selective hydrogen purification through graphdiyne under ambient temperature and pressure, Nanoscale 4(2012) 4587-4593.

[22] H.Y. Zhang, X.J. He, M.Z. Zhao, M. Zhang, L.X. Zhao, X.J. Feng, Y.H. Luo, Tunable hydrogen separation in sp-sp2 hybridized carbon membranes:a first-principles prediction, J. Phys. Chem. C 116(2012) 16634-16638.

[23] S.C. Lin, M.J. Buehler, Mechanics and molecular filtration performance of graphyne nanoweb membranes for selective water purification, Nanoscale 5(2013) 11801-11807.

[24] M.M. Xue, H. Qiu, W.L. Guo, Exceptionally fast water desalination at complete salt rejection by pristine graphyne monolayers, Nanotechnology 24(2013), 505720.

[25] C.Q. Zhu, H. Li, X.C. Zeng, E.G. Wang, S. Meng, Quantized water transport:ideal desalination through graphyne-4 membrane, Sci. Rep. 3(2013) 3163.

[26] J.L. Kou, X.Y. Zhou, H.J. Lu, F.M. Wu, J.T. Fan, Graphyne as the membrane for water desalination, Nanoscale 6(2014) 1865-1870.

[27] F. Liu, J. Yang, Z.J. Xu, X.N. Yang, Selective surface adsorption and pore trapping for ethanol-water mixtures near single-layer polyporous graphynes, Appl. Surf. Sci. 387(2016) 1080-1087.

[28] A. Nalaparaju, X.S. Zhao, J.W. Jiang, Biofuel purification by pervaporation and vapor permeation in metal-organic frameworks:a computational study, Energy Environ. Sci. 4(2011) 2107-2116.

[29] H.J. Huang, S. Ramaswamy, U.W. Tschirner, B.V. Ramarao, A review of separation technologies in current and future biorefineries, Sep. Purif. Technol. 62(2008) 1-21.

[30] G.P. Liu, W. Wei, W.Q. Jin, N.P. Xu, Polymer/ceramic composite membranes and their application in pervaporation process, Chin. J. Chem. Eng. 20(2012) 62-70.

[31] Y. Jiao, A.J. Du, M. Hankel, S.C. Smith, Modelling carbon membranes for gas and isotope separation, Phys. Chem. Chem. Phys. 15(2013) 4832-4843.

[32] M. Thomas, B. Corry, T.A. Hilder, What have we learnt about the mechanisms of rapid water transport, ion rejection and selectivity in nanopores from molecular simulation? Small 10(2014) 1453-1465.

[33] S. Plimpton, Fast parallel algorithms for short-range molecular-dynamics, J. Comput. Phys. 117(1995) 1-19.

[34] H.J.C. Berendsen, J.R. Grigera, T.P. Straatsma, The missing term in effective pair potentials, J. Phys. Chem. 91(1987) 6269-6271.

[35] M. Lundgren, N.L. Allan, T. Cosgrove, Wetting of water and water/ethanol droplets on a non-polar surface:a molecular dynamics study, Langmuir 18(2002) 10462-10466.

[36] J.T. Fern, D.J. Keffer, W.V. Steele, Vapor-liquid equilibrium of ethanol by molecular dynamics simulation and Voronoi tessellation, J. Phys. Chem. B 111(2007) 13278-13286.

[37] A.K. Metya, S. Khan, J.K. Singh, Wetting transition of the ethanol-water droplet on smooth and textured surfaces, J. Phys. Chem. C 118(2014) 4113-4121.

[38] N. Wei, X.S. Peng, Z.Q. Xu, Understanding water permeation in graphene oxide membranes, ACS Appl. Mater. Interfaces 6(2014) 5877-5883.

[39] M.D. Ma, L.M. Shen, J. Sheridan, J.Z. Liu, C. Chen, Q.S. Zheng, Friction of water slipping in carbon nanotubes, Phys. Rev. E 83(2011), 036316.

[40] M.E. Suk, N.R. Aluru, Molecular and continuum hydrodynamics in graphene nanopores, RSC Adv. 3(2013) 9365-9372.

[41] M.E. Suk, N.R. Aluru, Ion transport in sub-5-nm graphene nanopores, J. Chem. Phys. 140(2014), 084707.

[42] M. Mijakovic, K.D. Polok, B. Kezic, F. Sokolic, A. Perera, L. Zoranic, A comparison of force fields for ethanol-water mixtures, Mol. Simul. 41(2015) 699-712.

[43] M. Mijakovic, B. Kezic, L. Zoranic, F. Sokolic, A. Asenbaum, C. Pruner, E. Wilhelm, Ethanol-water mixtures:ultrasonics, Brillouin scattering and molecular dynamics, J. Mol. Liq. 164(2011) 66-73.

[44] Z.Q. Hu, Y.F. Chen, J.W. Jiang, Zeolitic imidazolate framework-8 as a reverse osmosis membrane for water desalination:insight from molecular simulation, J. Chem. Phys. 134(2011), 134705.

[45] N. Narita, S. Nagai, S. Suzuki, K. Nakao, Optimized geometries and electronic structures of graphyne and its family, Phys. Rev. B 58(1998) 11009-11014.

[46] G. Hummer, J.C. Rasaiah, J.P. Noworyta, Water conduction through the hydrophobic channel of a carbon nanotube, Nature 414(2001) 188-190.

[47] J.L. Kou, X.Y. Zhou, Y.Y. Chen, H.J. Lu, F.M. Wu, J.T. Fan, Water permeation through single-layer graphyne membrane, J. Chem. Phys. 139(2013), 064705.

[48] X.P. Ren, C.L. Wang, B. Zhou, H.P. Fang, J. Hu, R.H. Zhou, Ethanol promotes dewetting transition at low concentrations, Soft Matter 9(2013) 4655-4660.

[49] X.P. Ren, B. Zhou, C. Wang, Water-induced ethanol dewetting transition, J. Chem. Phys. 137(2012), 024703.

[50] M. Shahbabaei, D. Kim, Transport of water molecules through noncylindrical pores in multilayer nanoporous graphene, Phys. Chem. Chem. Phys. 19(2017) 20749-20759.

[51] D. Cohen-Tanugi, J.C. Grossman, Water desalination across nanoporous graphene, Nano Lett. 12(2012) 3602-3608.

[52] C.Q. Zhu, H. Li, S. Meng, Transport behavior of water molecules through twodimensional nanopores, J. Chem. Phys. 141(2014), 18C528.

[53] A. Nicolai, B.G. Sumpter, V. Meunier, Tunable water desalination across graphene oxide framework membranes, Phys. Chem. Chem. Phys. 16(2014) 8646-8654.

[54] D. Cohen-Tanugi, J.C. Grossman, Water permeability of nanoporous graphene at realistic pressures for reverse osmosis desalination, J. Chem. Phys. 141(2014), 074704.

[55] Z.Q. Hu, Y.F. Chen, J.W. Jiang, Zeolitic imidazolate framework-8 as a reverse osmosis membrane for water desalination:insight from molecular simulation, J. Chem. Phys. 134(2011), 134705.

[56] X.P. Yang, X.N. Yang, S.Y. Liu, Molecular dynamics simulation of water transport through graphene-based nanopores:flow behavior and structure characteristics, Chin. J. Chem. Eng. 23(2015) 1587-1592.

[57] M.E. Suk, N.R. Aluru, Water transport through ultrathin graphene, J. Phys. Chem. Lett. 1(2010) 1590-1594.

[58] N. Severin, I.M. Sokolov, J.P. Rabe, Dynamics of ethanol and water mixtures observed in a self-adjusting molecularly thin slit pore, Langmuir 30(2014) 3455-3459.

[59] M.Y. Zhao, X.N. Yang, Segregation structures and miscellaneous diffusions for ethanol/water mixtures in graphene-based nanoscale pores, J. Phys. Chem. C 119(2015) 21664-21673.

[60] S. Joseph, N.R. Aluru, Why are carbon nanotubes fast transporters of water? Nano Lett. 8(2008) 452-458.

[61] H.L. Du, J.Y. Li, J. Zhang, G. Su, X.Y. Li, Y.L. Zhao, Separation of hydrogen and nitrogen gases with porous graphene membrane, J. Phys. Chem. C 115(2011) 23261-23266.

[62] Y.D. Zhao, Y.Z. Xie, Z.K. Liu, X.S. Wang, Y. Chai, F. Yan, Two-dimensional material membranes:an emerging platform for controllable mass transport applications, Small 10(2014) 4521-4542.

[63] C.Z. Sun, M.S.H. Boutilier, H. Au, P. Poesio, B.F. Bai, R. Karnik, N.G. Hadjiconstantinou, Mechanisms of molecular permeation through nanoporous graphene membranes, Langmuir 30(2014) 675-682.

[64] K. Nieszporek, M. Drach, Alkane separation using nanoporous graphene membranes, Phys. Chem. Chem. Phys. 17(2015) 1018-1024.

[65] P. Peng, B.L. Shi, Y.Q. Lan, A review of membrane materials for ethanol recovery by pervaporation, Sep. Sci. Technol. 46(2011) 234-246.

[66] K.S. Chang, Y.C. Chung, T.H. Yang, S.J. Lue, K.L. Tung, Y.F. Lin, Free volume and alcohol transport properties of PDMS membranes:insights of nano-structure and interfacial affinity from molecular modeling, J. Membr. Sci. 417(2012) 119-130.

[67] S. Claes, P. Vandezande, S. Mullens, K. De Sitter, R. Peeters, M.K. Van Bael, Preparation and benchmarking of thin film supported PTMSP-silica pervaporation membranes, J. Membr. Sci. 389(2012) 265-271.