Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes
Abstract
It is highly desirable to integrate the CO2 solubility benefits of ionic liquids (ILs) in polymeric membrane systems for effective CO2 separations. Herein, we are exclusively exploring a series of four novel imidazolium-mediated Tröger’s base (TB)-containing ionene polymers for enhanced CO2 separation. The two diimidazole-functionalized Tröger’s base monomers synthesized from “ortho”- and “para”-substituted imidazole anilines were polymerized with equimolar amounts of two different aromatic and aliphatic comonomers (α,α'-dichloro-p-xylene and 1,10-dibromodecane, respectively) via Menshutkin reactions to obtain four respective ionene polymers ([Im-TB(o&p)-Xy][Cl] and ([Im-TB(o&p)-C10][Br], respectively). The resulting ionene polymers having halide anions were exchanged with [Tf2N]- anions, yielding a novel Tröger’s base material [Im-TB(x)-R][Tf2N] or “Im-TB-Ionenes”. The structural and physical properties as well as the gas separation behaviors of the copolymers of aromatic and aliphatic Im-TB-Ionenes have been extensively investigated with respect to the regiochemistry of imidazolium groups at the ortho and para positions of the TB unit. The imidazolium-mediated TB-Ionenes showed high CO2 solubility and hence an excellent CO2/CH4 permselectivity of 82.5. The Im-TB-Ionenes also displayed good thermal and mechanical stabilities.
- Authors:
-
- Department of Chemical & Biological Engineering, University of Alabama, Tuscaloosa, Alabama 35487-0203, United States
- NASA Marshall Space Flight Center, Huntsville, Alabama 35812, United States
- Publication Date:
- Research Org.:
- Univ. of Alabama, Tuscaloosa, AL (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
- OSTI Identifier:
- 1494862
- Alternate Identifier(s):
- OSTI ID: 1508826; OSTI ID: 1830539
- Grant/Contract Number:
- SC0018181; CHE-1726812; 80MSFC18M0041
- Resource Type:
- Published Article
- Journal Name:
- ACS Omega
- Additional Journal Information:
- Journal Name: ACS Omega Journal Volume: 4 Journal Issue: 2; Journal ID: ISSN 2470-1343
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Salts; Membranes; Solubility; Permeability; Polymers
Citation Formats
Kammakakam, Irshad, O’Harra, Kathryn E., Bara, Jason E., and Jackson, Enrique M. Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes. United States: N. p., 2019.
Web. doi:10.1021/acsomega.8b03700.
Kammakakam, Irshad, O’Harra, Kathryn E., Bara, Jason E., & Jackson, Enrique M. Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes. United States. https://doi.org/10.1021/acsomega.8b03700
Kammakakam, Irshad, O’Harra, Kathryn E., Bara, Jason E., and Jackson, Enrique M. Fri .
"Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes". United States. https://doi.org/10.1021/acsomega.8b03700.
@article{osti_1494862,
title = {Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes},
author = {Kammakakam, Irshad and O’Harra, Kathryn E. and Bara, Jason E. and Jackson, Enrique M.},
abstractNote = {It is highly desirable to integrate the CO2 solubility benefits of ionic liquids (ILs) in polymeric membrane systems for effective CO2 separations. Herein, we are exclusively exploring a series of four novel imidazolium-mediated Tröger’s base (TB)-containing ionene polymers for enhanced CO2 separation. The two diimidazole-functionalized Tröger’s base monomers synthesized from “ortho”- and “para”-substituted imidazole anilines were polymerized with equimolar amounts of two different aromatic and aliphatic comonomers (α,α'-dichloro-p-xylene and 1,10-dibromodecane, respectively) via Menshutkin reactions to obtain four respective ionene polymers ([Im-TB(o&p)-Xy][Cl] and ([Im-TB(o&p)-C10][Br], respectively). The resulting ionene polymers having halide anions were exchanged with [Tf2N]- anions, yielding a novel Tröger’s base material [Im-TB(x)-R][Tf2N] or “Im-TB-Ionenes”. The structural and physical properties as well as the gas separation behaviors of the copolymers of aromatic and aliphatic Im-TB-Ionenes have been extensively investigated with respect to the regiochemistry of imidazolium groups at the ortho and para positions of the TB unit. The imidazolium-mediated TB-Ionenes showed high CO2 solubility and hence an excellent CO2/CH4 permselectivity of 82.5. The Im-TB-Ionenes also displayed good thermal and mechanical stabilities.},
doi = {10.1021/acsomega.8b03700},
journal = {ACS Omega},
number = 2,
volume = 4,
place = {United States},
year = {Fri Feb 15 00:00:00 EST 2019},
month = {Fri Feb 15 00:00:00 EST 2019}
}
https://doi.org/10.1021/acsomega.8b03700
Web of Science
Figures / Tables:
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