Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes

O’Harra, Kathryn E.; Kammakakam, Irshad; Devriese, Emily M.; Noll, Danielle M.; Bara, Jason E.; Jackson, Enrique M.

doi:10.3390/membranes9070079

Title: Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes

Abstract

Three new isomeric 6FDA-based polyimide-ionenes, with imidazolium moieties and varying regiochemistry (para-, meta-, and ortho- connectivity), and composites with three different ionic liquids (ILs) have been developed as gas separation membranes. The structural-property relationships and gas separation behaviors of the newly developed 6FDA polyimide-ionene + IL composites have been extensively studied. All the 6FDA-based polyimide-ionenes exhibited good compatibility with the ILs and produced homogeneous hybrid membranes with the high thermal stability of ~380 °C. Particularly, [6FDA I4A pXy][Tf₂N] ionene + IL hybrids having [C₄mim][Tf₂N] and [Bnmim][Tf₂N] ILs offered mechanically stable matrixes with high CO₂ affinity. The permeability of CO₂ was increased by factors of 2 and 3 for C₄mim and Bnmim hybrids (2.15 to 6.32 barrers), respectively, compared to the neat [6FDA I4A pXy][Tf₂N] without sacrificing their permselectivity for CO₂/CH₄ and CO₂/N₂ gas pairs.

Authors:

O’Harra, Kathryn E.;

; Devriese, Emily M.; Noll, Danielle M.;

; Jackson, Enrique M.

Publication Date:: Wed Jul 03 00:00:00 EDT 2019

Research Org.:: Univ. of Alabama, Tuscaloosa, AL (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Aeronautics and Space Administration (NASA); National Science Foundation (NSF)

OSTI Identifier:: 1530918

Alternate Identifier(s):: OSTI ID: 1612862; OSTI ID: 1830540

Grant/Contract Number:: SC0018181; CAN 80MSFC18M0041; CHE-1726812

Resource Type:: Published Article

Journal Name:: Membranes

Additional Journal Information:: Journal Name: Membranes Journal Volume: 9 Journal Issue: 7; Journal ID: ISSN 2077-0375

Publisher:: MDPI

Country of Publication:: Switzerland

Language:: English

Subject:: 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 6FDA polyimides; ionenes; Hybrid Membranes; CO2 Separation

Citation Formats


                    O’Harra, Kathryn E., Kammakakam, Irshad, Devriese, Emily M., Noll, Danielle M., Bara, Jason E., and Jackson, Enrique M. Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes.  Switzerland: N. p., 2019. 
Web.  doi:10.3390/membranes9070079.

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                    O’Harra, Kathryn E., Kammakakam, Irshad, Devriese, Emily M., Noll, Danielle M., Bara, Jason E., & Jackson, Enrique M. Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes.  Switzerland.  https://doi.org/10.3390/membranes9070079

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                    O’Harra, Kathryn E., Kammakakam, Irshad, Devriese, Emily M., Noll, Danielle M., Bara, Jason E., and Jackson, Enrique M. Wed .  
"Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes".  Switzerland.  https://doi.org/10.3390/membranes9070079.

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@article{osti_1530918,

  title        = {Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes},

  author       = {O’Harra, Kathryn E. and Kammakakam, Irshad and Devriese, Emily M. and Noll, Danielle M. and Bara, Jason E. and Jackson, Enrique M.},

  abstractNote = {Three new isomeric 6FDA-based polyimide-ionenes, with imidazolium moieties and varying regiochemistry (para-, meta-, and ortho- connectivity), and composites with three different ionic liquids (ILs) have been developed as gas separation membranes. The structural-property relationships and gas separation behaviors of the newly developed 6FDA polyimide-ionene + IL composites have been extensively studied. All the 6FDA-based polyimide-ionenes exhibited good compatibility with the ILs and produced homogeneous hybrid membranes with the high thermal stability of ~380 °C. Particularly, [6FDA I4A pXy][Tf2N] ionene + IL hybrids having [C4mim][Tf2N] and [Bnmim][Tf2N] ILs offered mechanically stable matrixes with high CO2 affinity. The permeability of CO2 was increased by factors of 2 and 3 for C4mim and Bnmim hybrids (2.15 to 6.32 barrers), respectively, compared to the neat [6FDA I4A pXy][Tf2N] without sacrificing their permselectivity for CO2/CH4 and CO2/N2 gas pairs.},

  doi          = {10.3390/membranes9070079},

  journal      = {Membranes},

  number       = 7,

  volume       = 9,

  place        = {Switzerland},

  year         = {Wed Jul 03 00:00:00 EDT 2019},

  month        = {Wed Jul 03 00:00:00 EDT 2019}

}

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Works referencing / citing this record:

A Facile Synthesis of (PIM-Polyimide)-(6FDA-Durene-Polyimide) Copolymer as Novel Polymer Membranes for CO2 Separation
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Title: Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes

Abstract

Citation Formats

Synthesis and properties of polyimides derived from isomeric biphenyltetracarboxylic dianhydrides journal, September 2000

Preparation and characterization of imidazolium-functionalized poly (ether sulfone) as anion exchange membrane and ionomer for fuel cell application journal, July 2013

New Pyridinium Type Poly(Ionic Liquids) as Membranes for CO2 Separation journal, August 2018

Tröger’s Base-Based Microporous Polyimide Membranes for High-Performance Gas Separation journal, June 2014

Thermal analysis and its application in evaluation of fluorinated polyimide membranes for gas separation journal, August 2011

Approaches to Suppress CO2-Induced Plasticization of Polyimide Membranes in Gas Separation Applications journal, January 2019

Imidazole- and imidazolium-containing polymers for biology and material science applications journal, May 2010

Soluble and Colorless Poly(ether-imide)s Based on a Benzonorbornane Bis(ether anhydride) and Trifluoromethyl-Substituted Aromatic Bis(ether-amine)s journal, October 2006

Recent Advances in the Design of Ionenes: Toward Convergence with High‐Performance Polymers journal, May 2019

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Preparation and characterization of imidazolium-PEO-based Ionene/PVDF(HFP)/LiTFSI as a novel Gel polymer electrolyte journal, December 2014

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Phosphonium-based poly(Ionic liquid) membranes: The effect of cation alkyl chain length on light gas separation properties and Ionic conductivity journal, January 2016

Guide to CO 2 Separations in Imidazolium-Based Room-Temperature Ionic Liquids journal, March 2009

Polyimides containing aliphatic/alicyclic segments in the main chains journal, May 2019

PEG–imidazolium-functionalized 6FDA–durene polyimide as a novel polymeric membrane for enhanced CO 2 separation journal, January 2016

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Vibrational Spectroscopy of Ionic Liquids journal, January 2017

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Modification of poly(aryl ether ketone) using imidazolium groups as both pendants and bridging joints for anion exchange membranes journal, December 2015

Transparent and soluble polyimide films from 1,4:3,6-dianhydro-D-mannitol based dianhydride and diamines containing aromatic and semiaromatic units: Preparation, characterization, thermal and mechanical properties journal, May 2018

Novel Aromatic Polyimides Derived from 5′- t -Butyl-2′-pivaloylimino-3,4,3′′,4′′- m -terphenyltetracarboxylic Dianhydride with Potential Application on Gas Separation Processes journal, March 2010

Synthesis of copolyimides based on room temperature ionic liquid diamines journal, August 2010

High performance membranes based on ionic liquid polymers for CO2 separation from the flue gas journal, January 2012

Separation of aromatic hydrocarbons from alkanes using ammonium ionic liquid C2NTf2 at T=298.15K journal, October 2007

Synthesis and characterization of triptycene-based polyimides with tunable high fractional free volume for gas separation membranes journal, January 2014

Synthesis of room temperature ionic liquids based random copolyimides for gas separation applications journal, February 2013

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CO2 Capture by a Task-Specific Ionic Liquid journal, February 2002

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Alkyl imidazolium-functionalized cardo-based poly(ether ketone)s as novel polymer membranes for O2/N2 and CO2/N2 separations journal, June 2013

6FDA-DETDA: DABE polyimide-derived carbon molecular sieve hollow fiber membranes: Circumventing unusual aging phenomena journal, January 2018

A Facile Synthesis of (PIM-Polyimide)-(6FDA-Durene-Polyimide) Copolymer as Novel Polymer Membranes for CO2 Separation journal, August 2019

Synthesis and properties of polyimides derived from isomeric biphenyltetracarboxylic dianhydrides
journal, September 2000

Preparation and characterization of imidazolium-functionalized poly (ether sulfone) as anion exchange membrane and ionomer for fuel cell application
journal, July 2013

New Pyridinium Type Poly(Ionic Liquids) as Membranes for CO2 Separation
journal, August 2018

Tröger’s Base-Based Microporous Polyimide Membranes for High-Performance Gas Separation
journal, June 2014

Thermal analysis and its application in evaluation of fluorinated polyimide membranes for gas separation
journal, August 2011

Approaches to Suppress CO2-Induced Plasticization of Polyimide Membranes in Gas Separation Applications
journal, January 2019

Imidazole- and imidazolium-containing polymers for biology and material science applications
journal, May 2010

Soluble and Colorless Poly(ether-imide)s Based on a Benzonorbornane Bis(ether anhydride) and Trifluoromethyl-Substituted Aromatic Bis(ether-amine)s
journal, October 2006

Recent Advances in the Design of Ionenes: Toward Convergence with High‐Performance Polymers
journal, May 2019

Effects of hard-segment polymers on CO2/N2 gas-separation properties of poly(ethylene oxide)-segmented copolymers
journal, January 2000

Preparation and characterization of imidazolium-PEO-based Ionene/PVDF(HFP)/LiTFSI as a novel Gel polymer electrolyte
journal, December 2014

Combination of ionic liquids with membrane technology: A new approach for CO2 separation
journal, January 2016

Ionic Polyimides: Hybrid Polymer Architectures and Composites with Ionic Liquids for Advanced Gas Separation Membranes
journal, April 2017

Phosphonium-based poly(Ionic liquid) membranes: The effect of cation alkyl chain length on light gas separation properties and Ionic conductivity
journal, January 2016

Guide to CO ₂ Separations in Imidazolium-Based Room-Temperature Ionic Liquids
journal, March 2009

Polyimides containing aliphatic/alicyclic segments in the main chains
journal, May 2019

PEG–imidazolium-functionalized 6FDA–durene polyimide as a novel polymeric membrane for enhanced CO ₂ separation
journal, January 2016

PEG-imidazolium-incorporated polyimides as high-performance CO2-selective polymer membranes: The effects of PEG-imidazolium content
journal, May 2017

A potential ionic liquid for CO ₂ -separating gas membranes: selection and gas solubility studies
journal, January 2009

Vibrational Spectroscopy of Ionic Liquids
journal, January 2017

Ionic group-mediated crosslinked polyimide membranes for enhanced CO ₂ separation
journal, January 2015

Modification of poly(aryl ether ketone) using imidazolium groups as both pendants and bridging joints for anion exchange membranes
journal, December 2015

Transparent and soluble polyimide films from 1,4:3,6-dianhydro-D-mannitol based dianhydride and diamines containing aromatic and semiaromatic units: Preparation, characterization, thermal and mechanical properties
journal, May 2018

Novel Aromatic Polyimides Derived from 5′- t -Butyl-2′-pivaloylimino-3,4,3′′,4′′- m -terphenyltetracarboxylic Dianhydride with Potential Application on Gas Separation Processes
journal, March 2010

Synthesis of copolyimides based on room temperature ionic liquid diamines
journal, August 2010

High performance membranes based on ionic liquid polymers for CO2 separation from the flue gas
journal, January 2012

Separation of aromatic hydrocarbons from alkanes using ammonium ionic liquid C2NTf2 at T=298.15K
journal, October 2007

Synthesis and characterization of triptycene-based polyimides with tunable high fractional free volume for gas separation membranes
journal, January 2014

Synthesis of room temperature ionic liquids based random copolyimides for gas separation applications
journal, February 2013

Self‐healing imidazolium‐based ionene‐polyamide membranes: an experimental study on physical and gas transport properties
journal, March 2019

Design of Ion Conductive Polymers Based on Ionic Liquids
journal, April 2007

Understanding the effects of backbone chemistry and anion type on the structure and thermal behaviors of imidazolium polyimide‐ionenes
journal, May 2019

Turning into poly(ionic liquid)s as a tool for polyimide modification: synthesis, characterization and CO ₂ separation properties
journal, January 2016

Polyimides
journal, August 1991

Relationship between interchain spacing of amorphous polymers and blend miscibility as determined by wide-angle X-ray scattering
journal, July 1991

CO₂ Capture by a Task-Specific Ionic Liquid
journal, February 2002

Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO ₂ Separation Membranes
journal, February 2019

The strategies of molecular architecture and modification of polyimide-based membranes for CO2 removal from natural gas—A review
journal, June 2009

High Performance Polyimide with High Internal Free Volume Elements
journal, January 2011

Gas separation performance of 6FDA-based polyimides with different chemical structures
journal, October 2013

Gas transport properties in (6FDA-RTIL)-(6FDA-MDA) block copolyimides
journal, November 2015

Highly permeable Thermally Rearranged Mixed Matrix Membranes (TR-MMM)
journal, September 2019

The upper bound revisited
journal, July 2008

Alkyl imidazolium-functionalized cardo-based poly(ether ketone)s as novel polymer membranes for O2/N2 and CO2/N2 separations
journal, June 2013

6FDA-DETDA: DABE polyimide-derived carbon molecular sieve hollow fiber membranes: Circumventing unusual aging phenomena
journal, January 2018

A Facile Synthesis of (PIM-Polyimide)-(6FDA-Durene-Polyimide) Copolymer as Novel Polymer Membranes for CO2 Separation
journal, August 2019