Preparation of defect-free asymmetric gas separation membranes with dihydrolevoglucosenone (CyreneTM) as a greener polar aprotic solvent

Bridge, Alexander T.; Pedretti, Benjamin J.; Brennecke, Joan F.; Freeman, Benny D.

doi:10.1016/j.memsci.2021.120173

Preparation of defect-free asymmetric gas separation membranes with dihydrolevoglucosenone (Cyrene^TM) as a greener polar aprotic solvent

Journal Article · Fri Dec 10 00:00:00 EST 2021 · Journal of Membrane Science

DOI:https://doi.org/10.1016/j.memsci.2021.120173· OSTI ID:1977440

^[1]; ^[1]; Brennecke, Joan F. ^[1]; Freeman, Benny D. ^[1]

Univ. of Texas, Austin, TX (United States)

Nonsolvent-induced phase separation (NIPS) is widely used to prepare asymmetric gas separation membranes. Most industrial NIPS casting solution formulations are limited to a small group of glassy polymers and, importantly, require toxic polar aprotic solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), or N-methyl-2-pyrrolidone (NMP). Growing restrictions on the use of such solvents are spurring the search for more benign casting solution formulations that do not compromise membrane performance. Herein this study reports high-flux, defect-free asymmetric polysulfone (PSf) gas separation membranes prepared using dihydrolevoglucosenone (Cyrene^TM), a polar aprotic solvent that is believed to be safer than DMAc, DMF, and NMP, as the majority casting solution component. Optimized formulations and casting conditions produce membranes with hydrogen permeances exceeding 100 gas permeance units (GPU) and selectivities at or above those of dense PSf films. Dry/wet NIPS membrane performance improved with shorter dry step times and increased Cyrene^TM loadings relative to the volatile solvent, tetrahydrofuran (THF), in the casting solution. The high water-Cyrene^TM Flory-Huggins interaction parameter, _{$$\mathcal{X}12$$}, and high casting solution viscosities help suppress the formation of skin layer defects and sublayer macrovoids. In some cases, membrane selectivities were influenced by substructure resistance, providing insight into the relationship between sublayer morphology and membrane performance.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Materials for Water and Energy Systems (M-WET); Univ. of Texas, Austin, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0019272

OSTI ID:: 1977440

Journal Information:: Journal of Membrane Science, Journal Name: Journal of Membrane Science Journal Issue: C Vol. 644; ISSN 0376-7388

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (32)

Liquid-liquid phase separation in polysulfone/solvent/water systems Kim, Je Young; Lee, Hwan Kwang; Baik, Ki Jun Journal of Applied Polymer Science, Vol. 65, Issue 13 https://doi.org/10.1002/(SICI)1097-4628(19970926)65:13<2643::AID-APP6>3.0.CO;2-B	journal	September 1997
Group-contribution estimation of activity coefficients in nonideal liquid mixtures Fredenslund, Aage; Jones, Russell L.; Prausnitz, John M. AIChE Journal, Vol. 21, Issue 6 https://doi.org/10.1002/aic.690210607	journal	November 1975
Structures and gas separation properties of asymmetric polysulfone membranes made by dry, wet, and dry/wet phase inversion Pinnau, Ingo; Koros, William J. Journal of Applied Polymer Science, Vol. 43, Issue 8 https://doi.org/10.1002/app.1991.070430811	journal	October 1991
Preparation of asymmetric loeb-sourirajan membranes So, M. T.; Eirich, F. R.; Strathmann, H. Journal of Polymer Science: Polymer Letters Edition, Vol. 11, Issue 3 https://doi.org/10.1002/pol.1973.130110311	journal	March 1973
A qualitative skin layer formation mechanism for membranes made by dry/wet phase inversion Pinnau, Ingo; Koros, William J. Journal of Polymer Science Part B: Polymer Physics, Vol. 31, Issue 4 https://doi.org/10.1002/polb.1993.090310406	journal	March 1993
Application of Flory-Huggins theory to ternary polymer-solvents equilibria: A case study Favre, E.; Nguyen, Q. T.; Clement, R. European Polymer Journal, Vol. 32, Issue 3 https://doi.org/10.1016/0014-3057(95)00146-8	journal	March 1996
Aqueous quenched asymmetric polysulfone membranes prepared by dry/wet phase separation Pesek, S. C.; Koros, W. J. Journal of Membrane Science, Vol. 81, Issue 1-2 https://doi.org/10.1016/0376-7388(93)85032-R	journal	June 1993
Effects of temperature and pressure on gas permselection properties in asymmetric membranes Wang, Dongliang; Li, K.; Teo, W. K. Journal of Membrane Science, Vol. 105, Issue 1-2 https://doi.org/10.1016/0376-7388(95)00053-F	journal	September 1995
The mechanism for formation of “skinned” membranes Frommer, M. A.; Feiner, I.; Kedem, O. Desalination, Vol. 7, Issue 3 https://doi.org/10.1016/S0011-9164(00)80207-6	journal	April 1970
Composite hollow fiber membranes for gas separation: the resistance model approach Henis, Jay M. S.; Tripodi, Mary K. Journal of Membrane Science, Vol. 8, Issue 3, p. 233-246 https://doi.org/10.1016/S0376-7388(00)82312-1	journal	January 1981
Mathematical calculation of binodal curves of a polymer/solvent/nonsolvent system in the phase inversion process Wei, Yong-Ming; Xu, Zhen-Liang; Yang, Xiao-Tian Desalination, Vol. 192, Issue 1-3 https://doi.org/10.1016/j.desal.2005.07.035	journal	May 2006
Determination of water/polymer interaction parameter for membrane-forming systems by sorption measurement and a fitting technique Karimi, M.; Albrecht, W.; Heuchel, M. Journal of Membrane Science, Vol. 265, Issue 1-2 https://doi.org/10.1016/j.memsci.2005.04.030	journal	November 2005
A novel green solvent alternative for polymeric membrane preparation via nonsolvent-induced phase separation (NIPS) Wang, Ho Hyun; Jung, Jun Tae; Kim, Jeong F. Journal of Membrane Science, Vol. 574 https://doi.org/10.1016/j.memsci.2018.12.051	journal	March 2019
New frontiers in sustainable membrane preparation: Cyrene™ as green bioderived solvent Marino, T.; Galiano, F.; Molino, A. Journal of Membrane Science, Vol. 580 https://doi.org/10.1016/j.memsci.2019.03.034	journal	June 2019
Physical aging of thin glassy polymer films monitored by gas permeability Huang, Y.; Paul, D. R. Polymer, Vol. 45, Issue 25 https://doi.org/10.1016/j.polymer.2004.10.019	journal	November 2004
Energy-efficient polymeric gas separation membranes for a sustainable future: A review Sanders, David F.; Smith, Zachary P.; Guo, Ruilan Polymer, Vol. 54, Issue 18 https://doi.org/10.1016/j.polymer.2013.05.075	journal	August 2013
Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents De bruyn, Mario; Budarin, Vitaliy L.; Misefari, Antonio ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 8 https://doi.org/10.1021/acssuschemeng.9b00470	journal	March 2019
Sea Water Demineralization by Means of an Osmotic Membrane Loeb, Sidney; Sourirajan, Srinivasa Advances in Chemistry https://doi.org/10.1021/ba-1963-0038.ch009	book	January 1963
Ionic liquids: An industrial cleanup solution Renner, Rebecca Environmental Science & Technology, Vol. 35, Issue 19 https://doi.org/10.1021/es012505a	journal	October 2001
Relationship between substructure resistance and gas separation properties of defect-free integrally skinned asymmetric membranes Pinnau, Ingo; Koros, William J. Industrial & Engineering Chemistry Research, Vol. 30, Issue 8 https://doi.org/10.1021/ie00056a024	journal	August 1991
Vapor-liquid equilibria by UNIFAC group contribution. 5. Revision and extension Hansen, Henrik K.; Rasmussen, Peter; Fredenslund, Aage Industrial & Engineering Chemistry Research, Vol. 30, Issue 10 https://doi.org/10.1021/ie00058a017	journal	October 1991
Infinite dilution activity coefficients predicted by UNIFAC group contribution Bastos, J. C.; Soares, M. E.; Medina, A. G. Industrial & Engineering Chemistry Research, Vol. 27, Issue 7 https://doi.org/10.1021/ie00079a030	journal	July 1988
Preparation and Characterization of Membranes Formed by Nonsolvent Induced Phase Separation: A Review Guillen, Gregory R.; Pan, Yinjin; Li, Minghua Industrial & Engineering Chemistry Research, Vol. 50, Issue 7 https://doi.org/10.1021/ie101928r	journal	April 2011
Gas transport properties of biphenol polysulfones Aitken, C. L.; Koros, W. J.; Paul, D. R. Macromolecules, Vol. 25, Issue 14 https://doi.org/10.1021/ma00040a008	journal	July 1992
Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents Sherwood, James; De bruyn, Mario; Constantinou, Andri Chem. Commun., Vol. 50, Issue 68 https://doi.org/10.1039/C4CC04133J	journal	January 2014
Sustainable wastewater treatment and recycling in membrane manufacturing Razali, Mayamin; Kim, Jeong F.; Attfield, Martin Green Chemistry, Vol. 17, Issue 12 https://doi.org/10.1039/C5GC01937K	journal	January 2015
Membrane manufacture for peptide separation Kim, DooLi; Salazar, Octavio R.; Nunes, Suzana Pereina Green Chemistry, Vol. 18, Issue 19 https://doi.org/10.1039/C6GC01259K	journal	January 2016
Towards cleaner PolarClean: efficient synthesis and extended applications of the polar aprotic solvent methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate Cseri, Levente; Szekely, Gyorgy Green Chemistry, Vol. 21, Issue 15 https://doi.org/10.1039/C9GC01958H	journal	January 2019
Cyrene™ is a green alternative to DMSO as a solvent for antibacterial drug discovery against ESKAPE pathogens Camp, Jason E.; Nyamini, Simbarashe B.; Scott, Fraser J. RSC Medicinal Chemistry, Vol. 11, Issue 1 https://doi.org/10.1039/C9MD00341J	journal	January 2020
Regulating Chemical Substances under REACH: The Choice between Authorization and Restriction and the Case of Dipolar Aprotic Solvents: Regulating Chemical Substances Under Reach Bergkamp, Lucas; Herbatschek, Nicolas Review of European, Comparative & International Environmental Law, Vol. 23, Issue 2 https://doi.org/10.1111/reel.12083	journal	July 2014
Fabrication of PES/PVP Water Filtration Membranes Using Cyrene®, a Safer Bio-Based Polar Aprotic Solvent Milescu, Roxana A.; McElroy, C. Robert; Farmer, Thomas J. Advances in Polymer Technology, Vol. 2019 https://doi.org/10.1155/2019/9692859	journal	July 2019
Thermodynamic Modeling and Validation of the Temperature Influence in Ternary Phase Polymer Systems Romay, Marta; Diban, Nazely; Urtiaga, Ane Polymers, Vol. 13, Issue 5 https://doi.org/10.3390/polym13050678	journal	February 2021

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Defect-free
Dihydrolevoglucosenone (CyreneTM)
Engineering
Gas separation
Nonsolvent-induced phase separation
Polymer science
Polysulfone

Preparation of defect-free asymmetric gas separation membranes with dihydrolevoglucosenone (CyreneTM) as a greener polar aprotic solvent

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Preparation of defect-free asymmetric gas separation membranes with dihydrolevoglucosenone (Cyrene^TM) as a greener polar aprotic solvent