DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Poly(ionic liquid)s with Dicationic Pendants as Gas Separation Membranes

Journal Article · · Membranes

Poly(norbornene)s and poly(ionic liquid)s are two different classes of attractive materials, which are known for their structural tunability and thermal stabilities, and have been extensively studied as gas separation membranes. The incorporation of ionic liquids (ILs) into the poly(norbornene) through post-polymerization has resulted in unique materials with synergistic properties. However, direct polymerization of norbornene-containing IL monomers as gas separation membranes are limited. To this end, a series of norbornene-containing imidazolium-based mono- and di-cationic ILs (NBM-mIm and NBM-DILs) with different connectivity and spacer lengths were synthesized and characterized spectroscopically. Subsequently, the poly(NBM-mIm) with bistriflimide [Tf2N−] and poly([NBM-DILs][Tf2N]2) comprising homo-, random-, and block- (co)polymers were synthesized via ring-opening metathesis polymerization using the air-stable Grubbs second-generation catalyst. Block copolymers (BCPs), specifically, [NBM-mIM][Tf2N] and [NBM-ImCnmIm] [Tf2N]2 (n = 4 and 6) were synthesized at two different compositions, which generated high molecular weight polymers with decent solubility relative to homo- and random (co)polymers of [NBM-DILs] [Tf2N]2. The prepared BCPs were efficiently analyzed by a host of analytical tools, including 1H-NMR, GPC, and WAXD. The successfully BCPs were cast into thin membranes ranging from 47 to 125 μm and their gas (CO2, N2, CH4, and H2) permeations were measured at 20 °C using a time-lag apparatus. These membranes displayed modest CO2 permeability in a non-linear fashion with respect to composition and a reverse trend in CO2/N2 permselectivity was observed, as a usual trade-off behavior between permeability and permselectivity.

Research Organization:
University of South Alabama, Mobile, AL (United States)
Sponsoring Organization:
National Science Foundation (NSF); USDOE Office of Science (SC); USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0020282
OSTI ID:
1846700
Journal Information:
Membranes, Journal Name: Membranes Journal Issue: 3 Vol. 12; ISSN 2077-0375; ISSN MBSEB6
Publisher:
MDPI AGCopyright Statement
Country of Publication:
Switzerland
Language:
English

References (55)

Imidazolium-functionalized norbornene ionic liquid block copolymer and silica composite electrolyte membranes for lithium-ion batteries journal February 2017
Recent Developments and Applications of Ionic Liquids in Gas Separation Membranes journal September 2019
Conductive Polymer Electrolytes Derived from Poly(norbornene)s with Pendant Ionic Imidazolium Moieties journal January 2008
Poly(ionic liquid)s: Platform for CO2 capture and catalysis journal April 2019
Poly(ionic liquid)s as antimicrobial materials journal August 2018
Current status and development of membranes for CO2/CH4 separation: A review journal January 2013
Membrane-based carbon capture from flue gas: a review journal September 2015
Current and future trends in polymer membrane-based gas separation technology: A comprehensive review journal June 2021
Applications of poly ionic liquids in proton exchange membrane fuel cells: A review journal October 2021
An experimental study of gas transport and separation properties of ionic liquids supported on nanofiltration membranes journal September 2006
Synthesis and light gas separations in cross-linked gemini room temperature ionic liquid polymer membranes journal May 2008
Improving CO2 selectivity in polymerized room-temperature ionic liquid gas separation membranes through incorporation of polar substituents journal August 2008
The upper bound revisited journal July 2008
Main-chain imidazolium polymer membranes for CO2 separations: An initial study of a new ionic liquid-inspired platform journal September 2010
Performance of nitrile-containing anions in task-specific ionic liquids for improved CO2/N2 separation journal May 2010
Polymeric ionic liquids (PILs): Effect of anion variation on their CO2 sorption journal February 2012
CO2/light gas separation performance of cross-linked poly(vinylimidazolium) gel membranes as a function of ionic liquid loading and cross-linker content journal April 2012
Effect of composition and nanostructure on CO2/N2 transport properties of supported alkyl-imidazolium block copolymer membranes journal March 2013
Ionic liquids: Innovative fluids for sustainable gas separation from industrial waste stream journal January 2021
Selection of appropriate biogas upgrading technology-a review of biogas cleaning, upgrading and utilisation journal November 2015
Assembly of Short-Chain Amphiphilic Homopolymers into Well-Defined Particles journal April 2020
Role of Chain Polarity on Ion and Polymer Dynamics: Molecular Volume-Based Analysis of the Dielectric Constant for Polymerized Norbornene-Based Ionic Liquids journal November 2020
Periodically Functionalized Linear Polyethylene with Tertiary Amino Groups via Regioselective Ring-Opening Metathesis Polymerization journal March 2021
Molecular-Level Tuning toward Aggregation Dynamics of Self-Healing Materials journal July 2019
Dual Anion–Cation Crosslinked Poly(ionic liquid) Composite Membranes for Enhanced CO 2 Separation journal October 2020
Accessing Siloxane Functionalized Polynorbornenes via Vinyl-Addition Polymerization for CO 2 Separation Membranes journal June 2016
Tailored CO 2 -Philic Anionic Poly(ionic liquid) Composite Membranes: Synthesis, Characterization, and Gas Transport Properties journal March 2020
Synthesis of Gold Nanoparticle Catalysts Based on a New Water-Soluble Ionic Polymer journal September 2011
Gas Solubilities in Room-Temperature Ionic Liquids journal June 2004
Enhanced CO 2 Separation Selectivity in Oligo(ethylene glycol) Functionalized Room-Temperature Ionic Liquids journal August 2007
Synthesis and Performance of Polymerizable Room-Temperature Ionic Liquids as Gas Separation Membranes journal August 2007
Effect of Anion on Gas Separation Performance of Polymer−Room-Temperature Ionic Liquid Composite Membranes journal December 2008
Membrane Gas Separation: A Review/State of the Art journal May 2009
CO2 Capture by a Task-Specific Ionic Liquid journal February 2002
Structure and Properties of High Stability Geminal Dicationic Ionic Liquids journal January 2005
Molecular design of crown ethers. 1. Effects of methylene chain length: 15- to 17-crown-5 and 18- to 22-crown-6 journal April 1984
Enhanced CO 2 Absorption of Poly(ionic liquid)s journal March 2005
Synthesis and Ordered Phase Separation of Imidazolium-Based Alkyl–Ionic Diblock Copolymers Made via ROMP journal July 2011
Polymeric Gas Separation Membranes journal March 2012
The distillation and volatility of ionic liquids journal February 2006
Applications of ionic liquids in the chemical industry journal January 2008
Polymeric ionic liquids for CO 2 capture and separation: potential, progress and challenges journal January 2015
Preparation of a ROMP-type imidazolium-functionalized norbornene ionic liquid block copolymer and the electrochemical property for lithium-ion batteries polyelectrolyte membranes journal January 2015
Poly(ω-bromoalkylnorbornenes-co-norbornene) by ROMP-hydrogenation: a robust support amenable to post-polymerization functionalization journal January 2015
Novel imidazolium-based poly(ionic liquid)s with different counterions for self-healing journal January 2017
Olefin metathesis in air using latent ruthenium catalysts: imidazole substituted amphiphilic hydrogenated ROMP polymers providing nano-sized reaction spaces in water journal January 2018
Substituted polynorbornene membranes: a modular template for targeted gas separations journal January 2021
High performance membranes based on ionic liquid polymers for CO2 separation from the flue gas journal January 2012
Grafting poly(ionic liquid) brushes for anti-bacterial and anti-biofouling applications journal January 2012
Imidazolium-containing, hydrophobic–ionic–hydrophilic ABC triblock copolymers: synthesis, ordered phase-separation, and supported membrane fabrication journal January 2013
Polymeric ionic liquids with mixtures of counter-anions: a new straightforward strategy for designing pyrrolidinium-based CO2 separation membranes journal January 2013
Synthesis of norbornene derivatives and their polymers via ROMP of norbornene derivatives journal January 2020
Vapor Pressure Mapping of Ionic Liquids and Low-Volatility Fluids Using Graded Isothermal Thermogravimetric Analysis journal April 2019
Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes journal March 2020
A Review on Ionic Liquid Gas Separation Membranes journal January 2021