Thermally stable cross-linked P84 with superior membrane H2/CO2 separation properties at 100 °C

Omidvar, Maryam; Stafford, Christopher M.; Lin, Haiqing

doi:10.1016/j.memsci.2019.01.003

Thermally stable cross-linked P84 with superior membrane H₂/CO₂ separation properties at 100 °C

Journal Article · Sun Jan 06 00:00:00 EST 2019 · Journal of Membrane Science

DOI:https://doi.org/10.1016/j.memsci.2019.01.003· OSTI ID:1659661

Omidvar, Maryam ^[1]; Stafford, Christopher M. ^[2]; Lin, Haiqing ^[3]

Univ. at Buffalo, NY (United States); University at Buffalo, The State University of New York
National Inst. of Standards and Technology (NIST), Gaithersburg, MD (United States)
Univ. at Buffalo, NY (United States)

Polymers with a strong size-sieving ability and superior H₂/CO₂ selectivity at 100 °C or above are of great interests for pre-combustion CO₂ capture. Polyimides (such as Matrimid and 6FDA-durene) have been cross-linked using diamines and show superior H₂/CO₂ selectivity. However, these cross-linked polymers cannot be used for the pre-combustion CO₂ capture because of the lack of thermal stability at 100 °C. As such, herein we demonstrate that commercial P84™ can be chemically cross-linked using 1,4-butanediamine (BuDA) to achieve robust H₂/CO₂ separation properties at 100–150 °C. The cross-linked P84 were thoroughly evaluated using Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA). The effects of the cross-linking time on the physical properties and H₂/CO₂ separation properties at various temperatures were determined and interpreted using a free volume model. An exemplary sample based on P84 cross-linked by BuDA for 6 h exhibits a H₂ permeability of 47 Barrers (1 Barrer = 3.35 × 10^–16 mol m/m² s Pa) and H₂/CO₂ selectivity of 14 at 100 °C, which is on the Robeson's upper bound, indicating their potential for practical applications.

View Accepted Manuscript (DOE)

Research Organization:: Univ. at Buffalo, NY (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Fossil Energy (FE)

Grant/Contract Number:: FE0026463

OSTI ID:: 1659661

Alternate ID(s):: OSTI ID: 1614283

Journal Information:: Journal of Membrane Science, Journal Name: Journal of Membrane Science Vol. 575; ISSN 0376-7388

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (35)

Molecularly Tuned Free Volume of Vapor Cross-Linked 6FDA-Durene/ZIF-71 MMMs for H ₂ /CO ₂ Separation at 150 °C Japip, Susilo; Liao, Kuo-Sung; Chung, Tai-Shung Advanced Materials, Vol. 29, Issue 4 https://doi.org/10.1002/adma.201603833	journal	November 2016
Diamine modification of P84 polyimide membranes for pervaporation dehydration of isopropanol Qiao, Xiangyi; Chung, Tai-Shung AIChE Journal, Vol. 52, Issue 10 https://doi.org/10.1002/aic.10964	journal	January 2006
Surface Modification of Polyimide Membranes by Diamines for H2 and CO2 Separation Chung, Tai-Shung; Shao, Lu; Tin, Pei Shi Macromolecular Rapid Communications, Vol. 27, Issue 13 https://doi.org/10.1002/marc.200600147	journal	July 2006
Sorption and transport of linear alkane hydrocarbons in biaxially oriented polyethylene terephthalate Dhoot, S. N.; Freeman, B. D.; Stewart, M. E. Journal of Polymer Science Part B: Polymer Physics, Vol. 39, Issue 11 https://doi.org/10.1002/polb.1092	journal	January 2001
A novel strategy for surface modification of polyimide membranes by vapor-phase ethylenediamine (EDA) for hydrogen purification Shao, Lu; Lau, Cher-Hon; Chung, Tai-Shung International Journal of Hydrogen Energy, Vol. 34, Issue 20 https://doi.org/10.1016/j.ijhydene.2009.07.115	journal	October 2009
A vapor-phase surface modification method to enhance different types of hollow fiber membranes for industrial scale hydrogen separation Lau, Cher Hon; Low, Bee Ting; Shao, Lu International Journal of Hydrogen Energy, Vol. 35, Issue 17 https://doi.org/10.1016/j.ijhydene.2010.06.013	journal	September 2010
Effects of cross-linking modification on gas separation performance of Matrimid membranes Tin, P. Journal of Membrane Science, Vol. 225, Issue 1-2 https://doi.org/10.1016/j.memsci.2003.08.005	journal	November 2003
The effects of 1,3-cyclohexanebis(methylamine) modification on gas transport and plasticization resistance of polyimide membranes Shao, L.; Chung, T.; Goh, S. Journal of Membrane Science, Vol. 267, Issue 1-2 https://doi.org/10.1016/j.memsci.2005.06.004	journal	December 2005
Reversible diamine cross-linking of polyimide membranes Powell, Clem E.; Duthie, Xavier J.; Kentish, Sandra E. Journal of Membrane Science, Vol. 291, Issue 1-2 https://doi.org/10.1016/j.memsci.2007.01.016	journal	March 2007
Polymeric membranes for nanofiltration in polar aprotic solvents See Toh, Y. H.; Lim, F. W.; Livingston, A. G. Journal of Membrane Science, Vol. 301, Issue 1-2 https://doi.org/10.1016/j.memsci.2007.06.034	journal	September 2007
Comparison of diamino cross-linking in different polyimide solutions and membranes by precipitation observation and gas transport Shao, Lu; Liu, Li; Cheng, Si-Xue Journal of Membrane Science, Vol. 312, Issue 1-2 https://doi.org/10.1016/j.memsci.2007.12.060	journal	April 2008
Polymeric membranes for the hydrogen economy: Contemporary approaches and prospects for the future Shao, Lu; Low, Bee Ting; Chung, Tai-Shung Journal of Membrane Science, Vol. 327, Issue 1-2 https://doi.org/10.1016/j.memsci.2008.11.019	journal	February 2009
Influence of temperature on the upper bound: Theoretical considerations and comparison with experimental results Rowe, Brandon W.; Robeson, Lloyd M.; Freeman, Benny D. Journal of Membrane Science, Vol. 360, Issue 1-2 https://doi.org/10.1016/j.memsci.2010.04.047	journal	September 2010
Carbon dioxide capture with membranes at an IGCC power plant Merkel, Tim C.; Zhou, Meijuan; Baker, Richard W. Journal of Membrane Science, Vol. 389 https://doi.org/10.1016/j.memsci.2011.11.012	journal	February 2012
Polybenzimidazole composite membranes for high temperature synthesis gas separations Berchtold, Kathryn A.; Singh, Rajinder P.; Young, Jennifer S. Journal of Membrane Science, Vol. 415-416 https://doi.org/10.1016/j.memsci.2012.05.005	journal	October 2012
Surface modification of polyimide membranes by diethylenetriamine (DETA) vapor for H2 purification and moisture effect on gas permeation Wang, Huan; Paul, Donald R.; Chung, Tai-Shung Journal of Membrane Science, Vol. 430 https://doi.org/10.1016/j.memsci.2012.12.008	journal	March 2013
Pervaporation dehydration of acetone using P84 co-polyimide flat sheet membranes modified by vapor phase crosslinking Mangindaan, Dave W.; Min Shi, Gui; Chung, Tai-Shung Journal of Membrane Science, Vol. 458 https://doi.org/10.1016/j.memsci.2014.01.030	journal	May 2014
Physical aging and plasticization of thick and thin films of the thermally rearranged ortho-functional polyimide 6FDA–HAB Wang, Huan; Chung, Tai-Shung; Paul, Donald R. Journal of Membrane Science, Vol. 458 https://doi.org/10.1016/j.memsci.2014.01.066	journal	May 2014
Hybrid polymer/MOF membranes for Organic Solvent Nanofiltration (OSN): Chemical modification and the quest for perfection Campbell, James; Burgal, Joao Da Silvao; Szekely, Gyorgy Journal of Membrane Science, Vol. 503 https://doi.org/10.1016/j.memsci.2016.01.024	journal	April 2016
Physical aging of glassy perfluoropolymers in thin film composite membranes. Part I. Gas transport properties Yavari, Milad; Le, Tho; Lin, Haiqing Journal of Membrane Science, Vol. 525 https://doi.org/10.1016/j.memsci.2016.07.002	journal	March 2017
Amplifying the molecular sieving capability of polyimide membranes via coupling of diamine networking and molecular architecture Low, Bee Ting; Xiao, Youchang; Chung, Tai Shung Polymer, Vol. 50, Issue 14 https://doi.org/10.1016/j.polymer.2009.04.059	journal	July 2009
Chemically cross-linkable polyimide membranes for improved transport plasticization resistance for natural gas separation Eguchi, Hiroshi; Kim, Danny J.; Koros, William J. Polymer, Vol. 58 https://doi.org/10.1016/j.polymer.2014.12.064	journal	February 2015
Cellulose triacetate doped with ionic liquids for membrane gas separation Lam, Benjamin; Wei, Min; Zhu, Lingxiang Polymer, Vol. 89 https://doi.org/10.1016/j.polymer.2016.02.033	journal	April 2016
Polybenzimidazole based random copolymers containing hexafluoroisopropylidene functional groups for gas separations at elevated temperatures Singh, Rajinder P.; Li, Xin; Dudeck, Kevin W. Polymer, Vol. 119 https://doi.org/10.1016/j.polymer.2017.04.075	journal	June 2017
In-line formation of chemically cross-linked P84® co-polyimide hollow fibre membranes for H2/CO2 separation Choi, Seung-Hak; Jansen, Johannes C.; Tasselli, Franco Separation and Purification Technology, Vol. 76, Issue 2 https://doi.org/10.1016/j.seppur.2010.09.031	journal	December 2010
Using iron (III) acetylacetonate as both a cross-linker and micropore former to develop polyimide membranes with enhanced gas separation performance Chua, Mei Ling; Xiao, Youchang; Chung, Tai-Shung Separation and Purification Technology, Vol. 133 https://doi.org/10.1016/j.seppur.2014.06.039	journal	September 2014
50th Anniversary Perspective : Polymers and Mixed Matrix Membranes for Gas and Vapor Separation: A Review and Prospective Opportunities Galizia, Michele; Chi, Won Seok; Smith, Zachary P. Macromolecules, Vol. 50, Issue 20 https://doi.org/10.1021/acs.macromol.7b01718	journal	October 2017
Effects of Thermal Treatments and Dendrimers Chemical Structures on the Properties of Highly Surface Cross-Linked Polyimide Films Xiao, Youchang; Shao, Lu; Chung, Tai-Shung Industrial & Engineering Chemistry Research, Vol. 44, Issue 9 https://doi.org/10.1021/ie048837g	journal	April 2005
Simultaneous Occurrence of Chemical Grafting, Cross-Linking, and Etching on the Surface of Polyimide Membranes and Their Impact on H ₂ /CO ₂ Separation Low, Bee Ting; Xiao, Youchang; Chung, Tai Shung Macromolecules, Vol. 41, Issue 4 https://doi.org/10.1021/ma702360p	journal	February 2008
Unprecedented size-sieving ability in polybenzimidazole doped with polyprotic acids for membrane H ₂ /CO ₂ separation Zhu, Lingxiang; Swihart, Mark T.; Lin, Haiqing Energy & Environmental Science, Vol. 11, Issue 1 https://doi.org/10.1039/C7EE02865B	journal	January 2018
Tightening polybenzimidazole (PBI) nanostructure via chemical cross-linking for membrane H ₂ /CO ₂ separation Zhu, Lingxiang; Swihart, Mark T.; Lin, Haiqing Journal of Materials Chemistry A, Vol. 5, Issue 37 https://doi.org/10.1039/C7TA03874G	journal	January 2017
Ultra-selective defect-free interfacially polymerized molecular sieve thin-film composite membranes for H ₂ purification Ali, Z.; Pacheco, F.; Litwiller, E. Journal of Materials Chemistry A, Vol. 6, Issue 1 https://doi.org/10.1039/C7TA07819F	journal	January 2018
Plasticization-Enhanced Hydrogen Purification Using Polymeric Membranes Lin, H. Science, Vol. 311, Issue 5761 https://doi.org/10.1126/science.1118079	journal	February 2006
Selective Gas Transport Through Few-Layered Graphene and Graphene Oxide Membranes Kim, Hyo Won; Yoon, Hee Wook; Yoon, Seon-Mi Science, Vol. 342, Issue 6154, p. 91-95 https://doi.org/10.1126/science.1236098	journal	October 2013
Ultrathin, Molecular-Sieving Graphene Oxide Membranes for Selective Hydrogen Separation Li, Hang; Song, Zhuonan; Zhang, Xiaojie Science, Vol. 342, Issue 6154, p. 95-98 https://doi.org/10.1126/science.1236686	journal	October 2013

Cited By (1)

Fabrication of Defect-Free P84® Polyimide Hollow Fiber for Gas Separation: Pathway to Formation of Optimized Structure Etxeberria-Benavides, Miren; Karvan, Oguz; Kapteijn, Freek Membranes, Vol. 10, Issue 1 https://doi.org/10.3390/membranes10010004	journal	December 2019

Similar Records

Tightening polybenzimidazole (PBI) nanostructure via chemical cross-linking for membrane H₂/CO₂ separation

Journal Article · Mon Sep 04 20:00:00 EDT 2017 · Journal of Materials Chemistry. A · OSTI ID:1398377

Tailoring sub-3.3 Å ultramicropores in advanced carbon molecular sieve membranes for blue hydrogen production

Journal Article · Tue Mar 08 19:00:00 EST 2022 · Science Advances · OSTI ID:1864405

Related Subjects

20 FOSSIL-FUELED POWER PLANTS
Cross-linking
Diamine
H2/CO2 separation
Membranes
P84