Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes

O’Harra, Kathryn E.; Kammakakam, Irshad; Noll, Danielle M.; Turflinger, Erika M.; Dennis, Grayson P.; Jackson, Enrique M.; Bara, Jason E.

doi:10.3390/membranes10030051

Title: Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes

Abstract

Here, we report the synthesis and thermophysical properties of seven primarily aromatic, imidazolium-based polyamide ionenes. The effects of varied para-, meta-, and ortho-connectivity, and spacing of ionic and amide functional groups, on structural and thermophysical properties were analyzed. Suitable, robust derivatives were cast into thin films, neat, or with stoichiometric equivalents of the ionic liquid (IL) 1-benzy-3-methylimidazolium bistriflimide ([Bnmim][Tf₂N]), and the gas transport properties of these membranes were measured. Pure gas permeabilities and permselectivities for N₂, CH₄, and CO₂ are reported. Consistent para-connectivity in the backbone was shown to yield the highest CO₂ permeability and suitability for casting as a very thin, flexible film. Derivatives containing terephthalamide segments exhibited the highest CO₂/CH₄ and CO₂/N₂ selectivities, yet CO₂ permeability decreased with further deviation from consistent para-linkages.

Authors:

O’Harra, Kathryn E. ^[1];

^[1]; Noll, Danielle M. ^[1]; Turflinger, Erika M. ^[1]; Dennis, Grayson P. ^[1]; Jackson, Enrique M. ^[2];

^[1]

Univ. of Alabama, Tuscaloosa, AL (United States). Dept. of Chemical and Biological Engineering
NASA Marshall Space Flight Center (MSFC), Huntsville, AL (United States)

Publication Date:: Sun Mar 22 00:00:00 EDT 2020

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

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

OSTI Identifier:: 1803277

Alternate Identifier(s):: OSTI ID: 1830601

Grant/Contract Number:: SC0018181

Resource Type:: Accepted Manuscript

Journal Name:: Membranes

Additional Journal Information:: Journal Volume: 10; Journal Issue: 3; Journal ID: ISSN 2077-0375

Publisher:: MDPI

Country of Publication:: United States

Language:: English

Subject:: 59 BASIC BIOLOGICAL SCIENCES; 36 MATERIALS SCIENCE; 42 ENGINEERING; biochemistry & molecular biology; chemistry; engineering; materials science; polymer science; aromatic polyamides; ionic liquids; ionenes; membranes; gas separations

Citation Formats


                    O’Harra, Kathryn E., Kammakakam, Irshad, Noll, Danielle M., Turflinger, Erika M., Dennis, Grayson P., Jackson, Enrique M., and Bara, Jason E. Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes.  United States: N. p., 2020. 
Web.  doi:10.3390/membranes10030051.

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                    O’Harra, Kathryn E., Kammakakam, Irshad, Noll, Danielle M., Turflinger, Erika M., Dennis, Grayson P., Jackson, Enrique M., & Bara, Jason E. Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes.  United States.  https://doi.org/10.3390/membranes10030051

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                    O’Harra, Kathryn E., Kammakakam, Irshad, Noll, Danielle M., Turflinger, Erika M., Dennis, Grayson P., Jackson, Enrique M., and Bara, Jason E. Sun .  
"Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes".  United States.  https://doi.org/10.3390/membranes10030051.  https://www.osti.gov/servlets/purl/1803277.

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@article{osti_1803277,

  title        = {Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes},

  author       = {O’Harra, Kathryn E. and Kammakakam, Irshad and Noll, Danielle M. and Turflinger, Erika M. and Dennis, Grayson P. and Jackson, Enrique M. and Bara, Jason E.},

  abstractNote = {Here, we report the synthesis and thermophysical properties of seven primarily aromatic, imidazolium-based polyamide ionenes. The effects of varied para-, meta-, and ortho-connectivity, and spacing of ionic and amide functional groups, on structural and thermophysical properties were analyzed. Suitable, robust derivatives were cast into thin films, neat, or with stoichiometric equivalents of the ionic liquid (IL) 1-benzy-3-methylimidazolium bistriflimide ([Bnmim][Tf2N]), and the gas transport properties of these membranes were measured. Pure gas permeabilities and permselectivities for N2, CH4, and CO2 are reported. Consistent para-connectivity in the backbone was shown to yield the highest CO2 permeability and suitability for casting as a very thin, flexible film. Derivatives containing terephthalamide segments exhibited the highest CO2/CH4 and CO2/N2 selectivities, yet CO2 permeability decreased with further deviation from consistent para-linkages.},

  doi          = {10.3390/membranes10030051},

  journal      = {Membranes},

  number       = 3,

  volume       = 10,

  place        = {United States},

  year         = {Sun Mar 22 00:00:00 EDT 2020},

  month        = {Sun Mar 22 00:00:00 EDT 2020}

}

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Title: Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes

Abstract

Citation Formats

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Gas permeation parameters and other physicochemical properties of a polymer of intrinsic microporosity: Polybenzodioxane PIM-1 journal, December 2008

Tailoring interlayer structure of molecular layer-by-layer assembled polyamide membranes for high separation performance journal, November 2015

Polyamide Membranes with Net-Like Nanostructures Induced by Different Charged MOFs for Elevated Nanofiltration journal, November 2019

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

Gas separation properties of aromatic polyamides containing hexafluoroisopropylidene groups journal, August 1995

Nanofiber multilayer membranes with tailored nanochannels prepared by molecular layer-by-layer assembly for high throughput separation journal, January 2017

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

Photocatalytic filtration reactors equipped with bi-plasmonic nanocomposite/poly acrylic acid-modified polyamide membranes for industrial wastewater treatment journal, April 2020

Synthesis and Characterization of Ionene-Polyamide Materials as Candidates for New Gas Separation Membranes
journal, January 2018

Controlled synthesis of high performance polyamide membrane with thin dense layer for water desalination
journal, October 2010

Hydrogen bonding and π–π interactions in imidazolium-chloride ionic liquid clusters
journal, January 2015

Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes
journal, July 2019

One-Step Surface Grafting Method for Preparing Zwitterionic Nanofiltation Membrane via In Situ Introduction of Initiator in Interfacial Polymerization
journal, April 2019

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

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

3D printed polyamide membranes for desalination
journal, August 2018

Synthesis and gas transport properties of polyamide membranes containing PDMS groups
journal, January 2019

Mechanically robust thermally rearranged (TR) polymer membranes with spirobisindane for gas separation
journal, May 2013

Gas permeation properties of polyamide membrane prepared by interfacial polymerization
journal, November 2007

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

Grafting polyzwitterions onto polyamide by click chemistry and nucleophilic substitution on nitrogen: A novel approach to enhance membrane fouling resistance
journal, January 2014

Polymers of Intrinsic Microporosity
journal, December 2012

Thin-Film Composite Polyamide Membranes Functionalized with Biocidal Graphene Oxide Nanosheets
journal, November 2013

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

Thermally rearranged (TR) polymer membranes with nanoengineered cavities tuned for CO2 separation
journal, June 2012

Zwitterion-Functionalized Graphene Oxide Incorporated Polyamide Membranes with Improved Antifouling Properties
journal, October 2018

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

Ionic liquid-based materials: a platform to design engineered CO ₂ separation membranes
journal, January 2016

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

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

Novel aromatic polyamides with main chain and pendant 1,2,4-triazole moieties and their application to the extraction/elimination of mercury cations from aqueous media
journal, January 2010

Formation and characterization of polyamide membranes via interfacial polymerization
journal, August 1994

Poly(ionic liquid)s: An update
journal, July 2013

Enhanced Gas Transport Performance of Polyamide Membranes by Postpolymerization Modification
journal, June 2018

Thermally Rearrangeable PIM-Polyimides for Gas Separation Membranes
journal, August 2014

Hydrogen Bond Preserving Stress Release Mechanism Is Key to the Resilience of Aramid Fibers
journal, October 2019

Membrane Gas Separation: A Review/State of the Art
journal, May 2009

Gas transport properties of reverse-selective poly(ether-b-amide6)/[Emim][BF4] gel membranes for CO2/light gases separation
journal, February 2015

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

Membrane-based gas separation
journal, August 1993

Design of an integrated membrane system for a high level hydrogen purification
journal, November 2006

3D printed chemically and mechanically robust membrane by selective laser sintering for separation of oil/water and immiscible organic mixtures
journal, April 2020

Control of biofouling on reverse osmosis polyamide membranes modified with biocidal nanoparticles and antifouling polymer brushes
journal, January 2014

Covalent Binding of Single-Walled Carbon Nanotubes to Polyamide Membranes for Antimicrobial Surface Properties
journal, June 2011

Thin Film Polyamide Membranes with Photoresponsive Antibacterial Activity
journal, July 2017

Hydrogen bonding, mobility, and structural transitions in aliphatic polyamides
journal, January 2006

A review on semi-aromatic polyamide TFC membranes prepared by interfacial polymerization: Potential for water treatment and desalination
journal, June 2017

Gas separation properties of Troeger’s base-bridged polyamides
journal, June 2017

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

Gas permeation parameters and other physicochemical properties of a polymer of intrinsic microporosity: Polybenzodioxane PIM-1
journal, December 2008

Tailoring interlayer structure of molecular layer-by-layer assembled polyamide membranes for high separation performance
journal, November 2015

Polyamide Membranes with Net-Like Nanostructures Induced by Different Charged MOFs for Elevated Nanofiltration
journal, November 2019

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

Gas separation properties of aromatic polyamides containing hexafluoroisopropylidene groups
journal, August 1995

Nanofiber multilayer membranes with tailored nanochannels prepared by molecular layer-by-layer assembly for high throughput separation
journal, January 2017

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

Photocatalytic filtration reactors equipped with bi-plasmonic nanocomposite/poly acrylic acid-modified polyamide membranes for industrial wastewater treatment
journal, April 2020