Supported bicyclic amidine ionic liquids as a potential CO2/N2 separation medium
Abstract
In this paper, five new room temperature ionic liquids were tested as supported ionic liquid membranes (SILMs) for CO2/N2 separation capability. This series of ionic liquids (ILs) contains bicyclic amidine cations of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) with small alkyl chain substituents. These ILs have been synthesized to examine the effects of cation structure on free volume. Relevant physical and chemical properties have been examined, including CO2 solubility and viscosity. The relationship between fractional free volume and permeability of gases is explored, with an interesting note on solubility. Each cation was paired with two different anions: bis(trifluoromethanesulfonyl)imide and tetracyanoborate, for further investigation of the cation-anion interaction on SILM permeability and selectivity. Finally, three of these new ILs have exceeded Robeson's upper bound for CO2/N2 gas separations.
- Authors:
-
[1];
[3];
- Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry. Joint Inst. for Advanced Materials
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division
- Univ. of California, Riverside, CA (United States). Dept. of Chemistry
- Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry. Joint Inst. for Advanced Materials; Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division
- Publication Date:
- Research Org.:
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1468162
- Alternate Identifier(s):
- OSTI ID: 1693501
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Membrane Science
- Additional Journal Information:
- Journal Volume: 565; Journal ID: ISSN 0376-7388
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; ionic liquid; carbon dioxide; free volume; SILM
Citation Formats
Schott, Jennifer A., Do-Thanh, Chi-Linh, Mahurin, Shannon M., Tian, Ziqi, Onishi, Nicole C., Jiang, De-en, and Dai, Sheng. Supported bicyclic amidine ionic liquids as a potential CO2/N2 separation medium. United States: N. p., 2018.
Web. doi:10.1016/j.memsci.2018.08.012.
Schott, Jennifer A., Do-Thanh, Chi-Linh, Mahurin, Shannon M., Tian, Ziqi, Onishi, Nicole C., Jiang, De-en, & Dai, Sheng. Supported bicyclic amidine ionic liquids as a potential CO2/N2 separation medium. United States. https://doi.org/10.1016/j.memsci.2018.08.012
Schott, Jennifer A., Do-Thanh, Chi-Linh, Mahurin, Shannon M., Tian, Ziqi, Onishi, Nicole C., Jiang, De-en, and Dai, Sheng. Tue .
"Supported bicyclic amidine ionic liquids as a potential CO2/N2 separation medium". United States. https://doi.org/10.1016/j.memsci.2018.08.012. https://www.osti.gov/servlets/purl/1468162.
@article{osti_1468162,
title = {Supported bicyclic amidine ionic liquids as a potential CO2/N2 separation medium},
author = {Schott, Jennifer A. and Do-Thanh, Chi-Linh and Mahurin, Shannon M. and Tian, Ziqi and Onishi, Nicole C. and Jiang, De-en and Dai, Sheng},
abstractNote = {In this paper, five new room temperature ionic liquids were tested as supported ionic liquid membranes (SILMs) for CO2/N2 separation capability. This series of ionic liquids (ILs) contains bicyclic amidine cations of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) with small alkyl chain substituents. These ILs have been synthesized to examine the effects of cation structure on free volume. Relevant physical and chemical properties have been examined, including CO2 solubility and viscosity. The relationship between fractional free volume and permeability of gases is explored, with an interesting note on solubility. Each cation was paired with two different anions: bis(trifluoromethanesulfonyl)imide and tetracyanoborate, for further investigation of the cation-anion interaction on SILM permeability and selectivity. Finally, three of these new ILs have exceeded Robeson's upper bound for CO2/N2 gas separations.},
doi = {10.1016/j.memsci.2018.08.012},
journal = {Journal of Membrane Science},
number = ,
volume = 565,
place = {United States},
year = {2018},
month = {8}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 2 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Carbon capture and storage update
journal, January 2014
- Boot-Handford, Matthew E.; Abanades, Juan C.; Anthony, Edward J.
- Energy Environ. Sci., Vol. 7, Issue 1
Worldwide innovations in the development of carbon capture technologies and the utilization of CO2
journal, January 2012
- Markewitz, Peter; Kuckshinrichs, Wilhelm; Leitner, Walter
- Energy & Environmental Science, Vol. 5, Issue 6
Development and Evaluation of Porous Materials for Carbon Dioxide Separation and Capture
journal, October 2011
- Bae, Youn-Sang; Snurr, Randall Q.
- Angewandte Chemie International Edition, Vol. 50, Issue 49
Novel imidazolium-based poly(ionic liquid)s: preparation, characterization, and absorption of CO2
journal, May 2011
- Xiong, Yu-Bing; Wang, Hong; Wang, Yu-Jiao
- Polymers for Advanced Technologies, Vol. 23, Issue 5
Carbon capture with ionic liquids: overview and progress
journal, January 2012
- Zhang, Xiangping; Zhang, Xiaochun; Dong, Haifeng
- Energy & Environmental Science, Vol. 5, Issue 5
Determination of the upper limits, benchmarks, and critical properties for gas separations using stabilized room temperature ionic liquid membranes (SILMs) for the purpose of guiding future research
journal, November 2009
- Scovazzo, Paul
- Journal of Membrane Science, Vol. 343, Issue 1-2
Combination of ionic liquids with membrane technology: A new approach for CO2 separation
journal, January 2016
- Dai, Zhongde; Noble, Richard D.; Gin, Douglas L.
- Journal of Membrane Science, Vol. 497
Reactive and Reversible Ionic Liquids for CO 2 Capture and Acid Gas Removal
journal, January 2012
- Shannon, Matthew S.; Bara, Jason E.
- Separation Science and Technology, Vol. 47, Issue 2
Ionic liquid-amine blends and CO2BOLs: Prospective solvents for natural gas sweetening and CO2 capture technology—A review
journal, January 2014
- Kumar, Satish; Cho, Jae Hyun; Moon, Il
- International Journal of Greenhouse Gas Control, Vol. 20
Ionic Liquids for CO 2 Capture and Emission Reduction
journal, December 2010
- Brennecke, Joan F.; Gurkan, Burcu E.
- The Journal of Physical Chemistry Letters, Vol. 1, Issue 24
State-of-the-Art of CO 2 Capture with Ionic Liquids
journal, June 2012
- Ramdin, Mahinder; de Loos, Theo W.; Vlugt, Thijs J. H.
- Industrial & Engineering Chemistry Research, Vol. 51, Issue 24
Performance of nitrile-containing anions in task-specific ionic liquids for improved CO2/N2 separation
journal, May 2010
- Mahurin, Shannon M.; Lee, Je Seung; Baker, Gary A.
- Journal of Membrane Science, Vol. 353, Issue 1-2
Understanding the High Solubility of CO 2 in an Ionic Liquid with the Tetracyanoborate Anion
journal, August 2011
- Babarao, Ravichandar; Dai, Sheng; Jiang, De-en
- The Journal of Physical Chemistry B, Vol. 115, Issue 32
High CO2 solubility, permeability and selectivity in ionic liquids with the tetracyanoborate anion
journal, January 2012
- Mahurin, Shannon M.; Hillesheim, Patrick C.; Yeary, Joshua S.
- RSC Advances, Vol. 2, Issue 31
Playing with ionic liquid mixtures to design engineered CO 2 separation membranes
journal, January 2014
- Tomé, Liliana C.; Florindo, Catarina; Freire, Carmen S. R.
- Physical Chemistry Chemical Physics, Vol. 16, Issue 32
Structure and dynamics of CO 2 and N 2 in a tetracyanoborate based ionic liquid
journal, January 2014
- Liu, Hongjun; Dai, Sheng; Jiang, De-en
- Phys. Chem. Chem. Phys., Vol. 16, Issue 5
Molecular Dynamics Simulation of Anion Effect on Solubility, Diffusivity, and Permeability of Carbon Dioxide in Ionic Liquids
journal, June 2014
- Liu, Hongjun; Dai, Sheng; Jiang, De-en
- Industrial & Engineering Chemistry Research, Vol. 53, Issue 25
Mutual and Thermal Diffusivity of Binary Mixtures of the Ionic Liquids [BMIM][C(CN) 3 ] and [BMIM][B(CN) 4 ] with Dissolved CO 2 by Dynamic Light Scattering
journal, April 2014
- Rausch, Michael H.; Heller, Andreas; Herbst, Jonas
- The Journal of Physical Chemistry B, Vol. 118, Issue 17
Dynamic Viscosity of Tetracyanoborate- and Tricyanomethanide-Based Ionic Liquids by Dynamic Light Scattering
journal, March 2015
- Bi, Shengshan; Koller, Thomas M.; Rausch, Michael H.
- Industrial & Engineering Chemistry Research, Vol. 54, Issue 11
Tetracyanoborate based ionic liquids for CO2 capture: From ab initio calculations to molecular simulations
journal, May 2016
- Gupta, Krishna M.
- Fluid Phase Equilibria, Vol. 415
Free Volume as the Basis of Gas Solubility and Selectivity in Imidazolium-Based Ionic Liquids
journal, April 2012
- Shannon, Matthew S.; Tedstone, Jason M.; Danielsen, Scott P. O.
- Industrial & Engineering Chemistry Research, Vol. 51, Issue 15
Green chemistry: Reversible nonpolar-to-polar solvent
journal, August 2005
- Jessop, Philip G.; Heldebrant, David J.; Li, Xiaowang
- Nature, Vol. 436, Issue 7054, p. 1102-1102
Low viscosity alkanolguanidine and alkanolamidine liquids for CO 2 capture
journal, January 2013
- Koech, Phillip K.; Zhang, Jian; Kutnyakov, Igor V.
- RSC Adv., Vol. 3, Issue 2
Carbon Dioxide Capture by Superbase-Derived Protic Ionic Liquids
journal, July 2010
- Wang, Congmin; Luo, Huimin; Jiang, De-en
- Angewandte Chemie International Edition, Vol. 49, Issue 34
DBU-Based Protic Ionic Liquids for CO 2 Capture
journal, August 2017
- Zhu, Xiao; Song, Mengling; Xu, Yingjie
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 9
Chemisorption of carbon dioxide in imidazolium based ionic liquids with carboxylic anions
journal, February 2012
- Blath, Jessica; Deubler, Natalie; Hirth, Thomas
- Chemical Engineering Journal, Vol. 181-182
Equimolar CO2 capture by imidazolium-based ionic liquids and superbase systems
journal, January 2010
- Wang, Congmin; Luo, Huimin; Luo, Xiaoyan
- Green Chemistry, Vol. 12, Issue 11
DBU-Based Ionic-Liquid-Catalyzed Carbonylation of o -Phenylenediamines with CO 2 to 2-Benzimidazolones under Solvent-Free Conditions
journal, August 2013
- Yu, Bo; Zhang, Hongye; Zhao, Yanfei
- ACS Catalysis, Vol. 3, Issue 9
Synthesis, Characterization, and Thermophysical Properties of 1,8-Diazobicyclo[5.4.0]undec-7-ene Based Thiocyanate Ionic Liquids
journal, May 2014
- Lethesh, Kallidanthiyil Chellappan; Shah, Syed Nasir; Mutalib, M. I. Abdul
- Journal of Chemical & Engineering Data, Vol. 59, Issue 6
Synthesis, characterization, physical and thermodynamic properties of diazobicyclo undecene based dicyanamide ionic liquids
journal, August 2015
- Lethesh, Kallidanthiyil Chellappan; Shah, Syed Nasir; Abdul Mutalib, M. I.
- Journal of Molecular Liquids, Vol. 208
DBU and DBU-Derived Ionic Liquid Synergistic Catalysts for the Conversion of Carbon Dioxide/Carbon Disulfide to 3-Aryl-2-oxazolidinones/[1,3]Dithiolan-2-ylidenephenyl- amine
journal, January 2016
- Wang, Binshen; Luo, Zhoujie; Elageed, Elnazeer H. M.
- ChemCatChem, Vol. 8, Issue 4
Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena
journal, February 1995
- Klamt, Andreas
- The Journal of Physical Chemistry, Vol. 99, Issue 7
Refinement and Parametrization of COSMO-RS
journal, June 1998
- Klamt, Andreas; Jonas, Volker; Bürger, Thorsten
- The Journal of Physical Chemistry A, Vol. 102, Issue 26
Electronic structure calculations on workstation computers: The program system turbomole
journal, October 1989
- Ahlrichs, Reinhart; Bär, Michael; Häser, Marco
- Chemical Physics Letters, Vol. 162, Issue 3
COSMO Implementation in TURBOMOLE: Extension of an efficient quantum chemical code towards liquid systems
journal, January 2000
- Schäfer, Ansgar; Klamt, Andreas; Sattel, Diana
- Physical Chemistry Chemical Physics, Vol. 2, Issue 10
Density-functional exchange-energy approximation with correct asymptotic behavior
journal, September 1988
- Becke, A. D.
- Physical Review A, Vol. 38, Issue 6
Density-functional approximation for the correlation energy of the inhomogeneous electron gas
journal, June 1986
- Perdew, John P.
- Physical Review B, Vol. 33, Issue 12
Fast solvent screening via quantum chemistry: COSMO-RS approach
journal, February 2002
- Eckert, Frank; Klamt, Andreas
- AIChE Journal, Vol. 48, Issue 2
CO 2 /N 2 Selectivity Prediction in Supported Ionic Liquid Membranes (SILMs) by COSMO-RS
journal, May 2011
- Gonzalez-Miquel, Maria; Palomar, Jose; Omar, Salama
- Industrial & Engineering Chemistry Research, Vol. 50, Issue 9
Understanding the Physical Absorption of CO 2 in Ionic Liquids Using the COSMO-RS Method
journal, March 2011
- Palomar, Jose; Gonzalez-Miquel, Maria; Polo, Alicia
- Industrial & Engineering Chemistry Research, Vol. 50, Issue 6
Enhanced gas permeability by fabricating functionalized multi-walled carbon nanotubes and polyethersulfone nanocomposite membrane
journal, March 2011
- Ge, Lei; Zhu, Zhonghua; Rudolph, Victor
- Separation and Purification Technology, Vol. 78, Issue 1
Gas transport through homogeneous and asymmetric polyethersulfone membranes
journal, June 1993
- Kumazawa, H.; Wang, J. -S.; Sada, E.
- Journal of Polymer Science Part B: Polymer Physics, Vol. 31, Issue 7
New polyethersulfone (PESU) hollow fiber membranes for CO 2 capture
journal, April 2018
- Yong, Wai Fen; Chung, Tai-Shung; Weber, Martin
- Journal of Membrane Science, Vol. 552
Vibrational Spectroscopy of Ionic Liquids
journal, January 2017
- Paschoal, Vitor H.; Faria, Luiz F. O.; Ribeiro, Mauro C. C.
- Chemical Reviews, Vol. 117, Issue 10
Electronic Structure and Spectroscopic Analysis of 1-Ethyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide Ion Pair
journal, August 2014
- Vyas, Shubham; Dreyer, Christopher; Slingsby, Jason
- The Journal of Physical Chemistry A, Vol. 118, Issue 34
Infrared spectra of bis(trifluoromethanesulfonyl)imide based ionic liquids: Experiments and DFT simulations
journal, September 2014
- Vitucci, F. M.; Trequattrini, F.; Palumbo, O.
- Vibrational Spectroscopy, Vol. 74
Ionic liquid thermal stabilities: decomposition mechanisms and analysis tools
journal, January 2013
- Maton, Cedric; De Vos, Nils; Stevens, Christian V.
- Chemical Society Reviews, Vol. 42, Issue 13
Effect of alkyl and aryl substitutions on 1,2,4-triazolium-based ionic liquids for carbon dioxide separation and capture
journal, January 2013
- Hillesheim, Patrick C.; Singh, Joseph A.; Mahurin, Shannon M.
- RSC Advances, Vol. 3, Issue 12
Fluidic Carbon Precursors for Formation of Functional Carbon under Ambient Pressure Based on Ionic Liquids
journal, December 2009
- Lee, Je Seung; Wang, Xiqing; Luo, Huimin
- Advanced Materials, Vol. 22, Issue 9
Ionic Liquids as Precursors for Nitrogen-Doped Graphitic Carbon
journal, January 2010
- Paraknowitsch, Jens Peter; Zhang, Jian; Su, Dangsheng
- Advanced Materials, Vol. 22, Issue 1
Thermophysical Properties of Imidazolium-Based Ionic Liquids
journal, July 2004
- Fredlake, Christopher P.; Crosthwaite, Jacob M.; Hert, Daniel G.
- Journal of Chemical & Engineering Data, Vol. 49, Issue 4
Conformational States of Ionic Liquid 1-Ethyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide in Bulk and Confined Silica Nanopores Probed by Crystallization Kinetics Study
journal, October 2015
- Verma, Yogendra Lal; Singh, Rajendra Kumar
- The Journal of Physical Chemistry C, Vol. 119, Issue 43
Organic superbase derived ionic liquids based on the TFSI anion: synthesis, characterization, and electrochemical properties
journal, January 2017
- Wang, Zhi; Li, Zuopeng; Jin, Yunhe
- New Journal of Chemistry, Vol. 41, Issue 12
Why Is CO 2 So Soluble in Imidazolium-Based Ionic Liquids?
journal, April 2004
- Cadena, Cesar; Anthony, Jennifer L.; Shah, Jindal K.
- Journal of the American Chemical Society, Vol. 126, Issue 16
Correlation of separation factor versus permeability for polymeric membranes
journal, October 1991
- Robeson, Lloyd M.
- Journal of Membrane Science, Vol. 62, Issue 2
The upper bound revisited
journal, July 2008
- Robeson, Lloyd M.
- Journal of Membrane Science, Vol. 320, Issue 1-2, p. 390-400
Ionic liquids supported by isoporous membranes for CO2/N2 gas separation applications
journal, November 2015
- Grünauer, Judith; Shishatskiy, Sergey; Abetz, Clarissa
- Journal of Membrane Science, Vol. 494
Diffusivity of Carbon Dioxide in Room-Temperature Ionic Liquids
journal, October 2010
- Moganty, Surya S.; Baltus, Ruth E.
- Industrial & Engineering Chemistry Research, Vol. 49, Issue 19
Mutual and Self-Diffusivities in Binary Mixtures of [EMIM][B(CN) 4 ] with Dissolved Gases by Using Dynamic Light Scattering and Molecular Dynamics Simulations
journal, June 2015
- Koller, Thomas M.; Heller, Andreas; Rausch, Michael H.
- The Journal of Physical Chemistry B, Vol. 119, Issue 27
Correlations of Low-Pressure Carbon Dioxide and Hydrocarbon Solubilities in Imidazolium-, Phosphonium-, and Ammonium-Based Room-Temperature Ionic Liquids. Part 2. Using Activation Energy of Viscosity
journal, February 2008
- Kilaru, Prem K.; Scovazzo, Paul
- Industrial & Engineering Chemistry Research, Vol. 47, Issue 3
Correlating fractional free volume to CO2 selectivity in [Rmim][Tf2N] ionic liquids
journal, October 2014
- Jeffrey Horne, W.; Shannon, Matthew S.; Bara, Jason E.
- The Journal of Chemical Thermodynamics, Vol. 77
Bulk-Fluid Solubility and Membrane Feasibility of Rmim-Based Room-Temperature Ionic Liquids
journal, August 2006
- Camper, Dean; Bara, Jason; Koval, Carl
- Industrial & Engineering Chemistry Research, Vol. 45, Issue 18
Works referencing / citing this record:
Cyanoborates: Cyanoborates
journal, July 2019
- Ignat'ev, Nikolai V.; Finze, Maik
- European Journal of Inorganic Chemistry, Vol. 2019, Issue 31