Abstract
The effect of different cations and anions on the CO2 solubility in ionic liquids was investigated using a systematic approach in the current work. Four ionic liquids (ILs) containing the same cation ([C2CN Bim]) were synthesized, each incorporating a different anion (DDS, BS TFMS, and DOSS). In addition, four ILs with different cations ([C2CN Bim], [C2CN Him], [C2CN Oim], and [C2CN Dim]) were prepared, all containing the same anion (DOSS). Then, these ILs were characterized and utilized to determine how various cations and anions influence CO2 solubility. The prepared ILs were characterized using NMR and elemental analysis. Impurities, such as moisture and halide content were also determined. The CO2 solubility was studied using the gravimetric method (MSB) at pressures of 1, 5, 10, 15, and 20 bar. An investigation was also conducted to examine the influence of temperature on the solubility of CO2 in [C2CN Dim] [DOSS]. Henry’s law constants were calculated along with the thermodynamic properties such as standard enthalpy, entropy, and Gibbs free energy (ΔH0, ΔS0, ΔG0). In addition, the CO2/CH4 solubility selectivity was determined.
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Available upon requesting the first author. taha_a@rcjy.edu.sa.
References
E. Torralba-Calleja, J. Skinner, D. Gutiérrez-Tauste, CO2 capture in ionic liquids: A review of solubilities and experimental methods. J. Chem. 2013, 1–16 (2013)
J.D. Holbrey, K. Seddon, Ionic liquids. Clean Prod. Process. 1, 223–236 (1999)
K.R. Seddon, A taste of the future. Nat. Mater. 2, 363–365 (2003)
A. Jiménez, M. Bermúdez, F. Carrion, G. Martinez-Nicolas, Room temperature ionic liquids as lubricant additives in steel–aluminium contacts: influence of sliding velocity, normal load and temperature. Wear 261, 347–359 (2006)
M.J. Earle, K.R. Seddon, Ionic liquids. Green solvents for the future. Pure Appl. Chem. 72, 1391–1398 (2000)
K. E. Gutowski, "Industrial uses and applications of ionic liquids," Physical Sciences Reviews, vol. 3, 2018.
M. Kosmulski, J. Gustafsson, J.B. Rosenholm, Thermal stability of low temperature ionic liquids revisited. Thermochim. Acta 412, 47–53 (2004)
M. Pan, Y. Zhao, X. Zeng, J. Zou, Efficient absorption of CO2 by introduction of intramolecular hydrogen bonding in chiral amino acid ionic liquids. Energy Fuels 32, 6130–6135 (2018)
M. Ramdin, T.W. de Loos, T.J. Vlugt, State-of-the-art of CO2 capture with ionic liquids. Ind. Eng. Chem. Res. 51, 8149–8177 (2012)
H.S. Schrekker, M.P. Stracke, C.M.L. Schrekker, J. Dupont, Ether-functionalized imidazolium hexafluorophosphate ionic liquids for improved water miscibilities. Ind. Eng. Chem. Res. 46, 7389–7392 (2007)
F. Ding, X. He, X. Luo, W. Lin, K. Chen, H. Li, C. Wang, Highly efficient CO2 capture by carbonyl-containing ionic liquids through Lewis acid–base and cooperative C-H...O hydrogen bonding interaction strengthened by the anion. Chem. Commun. 50, 15041–15044 (2014)
Y.S. Sistla, V. Sridhar, Molecular understanding of carbon dioxide interactions with ionic liquids. J. Mol. Liq. 325, 115162 (2021)
F. Karadas, M. Atilhan, S. Aparicio, Review on the use of ionic liquids (ILs) as alternative fluids for CO2 capture and natural gas sweetening. Energy Fuels 24, 5817–5828 (2010)
J. Bara, C. Gabriel, T. Carlisle, D. Camper, A. Finotello, D. Gin, R. Noble, Gas separations in fluoroalkyl-functionalized room-temperature ionic liquids using supported liquid membranes. Chem. Eng. J. 147, 43–50 (2009)
X. Zhang, Z. Liu, W. Wang, Screening of ionic liquids to capture CO2 by COSMO RS and experiments. AIChE J. 54, 2717–2728 (2008)
D. Zhao, Z. Fei, R. Scopelliti, P.J. Dyson, Synthesis and characterization of ionic liquids incorporating the nitrile functionality. Inorg. Chem. 43, 2197–2205 (2004)
Q. Zhang, Z. Li, J. Zhang, S. Zhang, L. Zhu, J. Yang, X. Zhang, Y. Deng, Physicochemical properties of nitrile-functionalized ionic liquids. J. Phys. Chem. B 111, 2864–2872 (2007)
A.K. Ziyada, C.D. Wilfred, M.A. Bustam, Z. Man, T. Murugesan, Thermophysical properties of 1-propyronitrile-3-alkylimidazolium bromide ionic liquids at temperatures from (293.15 to 353.15) K. J. Chem. Eng. Data 55, 3886–3890 (2010)
A.K. Ziyada, M.A. Bustam, T. Murugesan, C.D. Wilfred, Effect of sulfonate-based anions on the physicochemical properties of 1-alkyl-3-propanenitrile imidazolium ionic liquids. New J. Chem. 35, 1111–1116 (2011)
A.K. Ziyada, M.A. Bustam, C.D. Wilfred, T. Murugesan, Densities, viscosities, and refractive indices of 1-hexyl-3-propanenitrile imidazolium ionic liquids incorporated with sulfonate-based anions. J. Chem. Eng. Data 56, 2343–2348 (2011)
M.W. Arshad, “CO2 capture using Ionic Liquids.’ Master’s thesis, Technical University of Denmark, DTU, DK-2800 Kgs. Lyngby, Denmark (2009)
A.K. Ziyada, C.D. Wilfred, Effect of cation modification on the physicochemical properties and CO2 solubility: nonfluorinated phosphonium-based ionic liquids incorporating a dioctylsulfosuccinate anion. J. Chem. Eng. Data 63, 3672–3683 (2018)
M.S.R. Shahrom, C.D. Wilfred, A.K.Z. Taha, CO2 capture by task specific ionic liquids (TSILs) and polymerized ionic liquids (PILs and AAPILs). J. Mol. Liq. 219, 306–312 (2016)
M. Gonzalez-Miquel, J. Bedia, C. Abrusci, J. Palomar, F. Rodriguez, Anion effects on kinetics and thermodynamics of CO2 absorption in ionic liquids. J. Phys. Chem. B 117, 3398–3406 (2013)
M. Shiflett, A. Yokozeki, Solubility of CO2 in room temperature ionic liquid [hmim][Tf2N]. J. Phys. Chem. B 111, 2070–2074 (2007)
J.C. Kotz, P.M. Treichel, and J.R. Townsend, D. Treichel, Chemistry & chemical reactivity, Cengage Learning (2014)
A.K. Ziyada, C.D. Wilfred, Physical properties of ionic liquids consisting of 1-butyl-3-propanenitrile-and 1-decyl-3-propanenitrile imidazolium-based cations: temperature dependence and influence of the anion. J. Chem. Eng. Data 59, 1232–1239 (2014)
J.L. Anthony, J.L. Anderson, E.J. Maginn, J.F. Brennecke, Anion effects on gas solubility in ionic liquids. J. Phys. Chem. B 109, 6366–6374 (2005)
A.K. Ziyada, C.D. Wilfred, Effect of temperature and anion on densities, viscosities, and refractive indices of 1-Octyl-3-propanenitrile imidazolium-based ionic liquids. J. Chem. Eng. Data 59, 1385–1390 (2014)
S.N.V.K. Aki, B.R. Mellein, E.M. Saurer, J.F. Brennecke, High-pressure phase behavior of carbon dioxide with imidazolium-based ionic liquids. J. Phys. Chem. B 108, 20355–20365 (2004)
L. A. Blanchard, "Ionic Liquids-Carbon Dioxide Systems: Phase Behavior, Solubilities and Extraction," Ph.D, Chemical Engineering, University of Notre Dame, Notre Dame, 2000
R. Baker, Future directions of membrane gas separation technology. Ind. Eng. Chem. Res. 41, 1393–1411 (2002)
J.M. Pringle, J. Golding, K. Baranyai, C.M. Forsyth, G.B. Deacon, J.L. Scott, D.R. MacFarlane, The effect of anion fluorination in ionic liquids—physical properties of a range of bis (methanesulfonyl) amide salts. New J. Chem. 27, 1504–1510 (2003)
G. Yu, S. Zhang, X. Yao, J. Zhang, K. Dong, W. Dai, R. Mori, Design of task-specific ionic liquids for capturing CO2: a molecular orbital study. Ind. Eng. Chem. Res. 45, 2875–2880 (2006)
E.D. Bates, R.D. Mayton, I. Ntai, J.H. Davis, CO2 capture by a task-specific ionic liquid. J. Am. Chem. Soc. 124, 926–927 (2002)
J. Bara, D. Camper, D. Gin, R. Noble, Room-temperature ionic liquids and composite materials: platform technologies for CO2 capture. Acc. Chem. Res. 43, 152–159 (2009)
T. Sarbu, T.J. Styranec, E.J. Beckman, Design and synthesis of low cost, sustainable CO2-philes. Ind. Eng. Chem. Res. 39, 4678–4683 (2000)
H. Tokuda, K. Hayamizu, K. Ishii, M. Susan, M. Watanabe, Physicochemical properties and structures of room temperature ionic liquids. 2. Variation of alkyl chain length in imidazolium cation. J. Phys. Chem. B 109, 6103–6110 (2005)
R. P. Swatloski, "Ionic Liquids as Green Solvents: Enabling New Materials and Technologies," Ph.D, Chemistry Department, University of Alabama, Tuscaloosa, 2005
D. Zhao, "Design, synthesis and applications of functionalized ionic liquids," M.Sc., Chemistry, **nan Petroleum University, Nanchong, China, 2007
W. Ren, B. Sensenich, A. Scurto, High-pressure phase equilibria of (carbon dioxide (CO2) + n-alkyl-imidazolium bis (trifluoromethylsulfonyl) amide) ionic liquids. J. Chem. Thermodyn. 42, 305–311 (2010)
D. Almantariotis, T. Gefflaut, A. Pa Dua, J. Coxam, M. Costa Gomes, Effect of fluorination and size of the alkyl side-chain on the solubility of carbon dioxide in 1-Alkyl-3-methylimidazolium Bis (trifluoromethylsulfonyl) amide ionic liquids. J. Phys. Chem. B 114, 3608–3617 (2010)
J.A. Schott, C.-L. Do-Thanh, W. Shan, N.G. Puskar, S. Dai, S.M. Mahurin, FTIR investigation of the interfacial properties and mechanisms of CO2 sorption in porous ionic liquids. Green Chemical Engineering 2, 392–401 (2021)
C. Wu, T.P. Senftle, W.F. Schneider, First-principles-guided design of ionic liquids for CO 2 capture. Phys. Chem. Chem. Phys. 14, 13163–13170 (2012)
X. Liu, K.E. O’Harra, J.E. Bara, C.H. Turner, Solubility behavior of CO2 in ionic liquids based on ionic polarity index analyses. J. Phys. Chem. B 125, 3665–3676 (2021)
S.D. Hojniak, I.P. Silverwood, A.L. Khan, I.F. Vankelecom, W. Dehaen, S.G. Kazarian, K. Binnemans, Highly selective separation of carbon dioxide from nitrogen and methane by nitrile/glycol-difunctionalized ionic liquids in supported ionic liquid membranes (SILMs). J. Phys. Chem. B 118, 7440–7449 (2014)
A.S. Shalygin, N.S. Nesterov, S.A. Prikhod’ko, N.Y. Adonin, O.N. Martyanov, S.G. Kazarian, Interactions of CO2 with the homologous series of CnMIMBF4 ionic liquids studied in situ ATR-FTIR spectroscopy: spectral characteristics, thermodynamic parameters and their correlation. J. Mol. Liq. 315, 113694 (2020)
J. Huang, A. Riisager, R. Berg, R. Fehrmann, Tuning ionic liquids for high gas solubility and reversible gas sorption. J. Mol. Catal. A: Chem. 279, 170–176 (2008)
J. Anthony, E. Maginn, J. Brennecke, Solubilities and thermodynamic properties of gases in the ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate. J. Phys. Chem. B 106, 7315–7320 (2002)
L. M. G. Sánchez, "Functionalized Ionic Liquids: Absorption Solvents for Carbon Dioxide and Olefin Separation," Ph.D, Chemical Engineering, Eindhoven University of Technology, Eindhoven, 2008
Z. Fei, W.H. Ang, D. Zhao, R. Scopelliti, E.E. Zvereva, S.A. Katsyuba, P.J. Dyson, Revisiting ether-derivatized imidazolium-based ionic liquids. J. Phys. Chem. B 111, 10095–10108 (2007)
J. Bara, C. Gabriel, S. Lessmann, T. Carlisle, A. Finotello, D. Gin, R. Noble, Enhanced CO2 separation selectivity in oligo (ethylene glycol) functionalized room-temperature ionic liquids. Ind. Eng. Chem. Res. 46, 5380–5386 (2007)
T. Carlisle, J. Bara, C. Gabriel, R. Noble, D. Gin, Interpretation of CO2 solubility and selectivity in nitrile-functionalized room-temperature ionic liquids using a group contribution approach. Ind. Eng. Chem. Res. 47, 7005–7012 (2008)
M. Muldoon, S. Aki, J. Anderson, J. Dixon, J. Brennecke, Improving carbon dioxide solubility in ionic liquids. J. Phys. Chem. B 111, 9001–9009 (2007)
Y. Deng, S. Morrissey, N. Gathergood, A.M. Delort, P. Husson, M.F. Costa Gomes, The presence of functional groups key for biodegradation in ionic liquids: effect on gas solubility. ChemSusChem: Chem. Sustain. Energy Mater. 3, 377–385 (2010)
A. M. Tagiuri, Studies of Solubility of CO2 in Ionic Liquids, Kinetics, and Heat of Reactions of CO2 in Promising Cyclic Amines: The University of Regina (Canada), 2019
P. Carvalho, V. Álvarez, I. Marrucho, M. Aznar, J. Coutinho, High carbon dioxide solubilities in trihexyltetradecylphosphonium-based ionic liquids. J. Supercrit. Fluids 52, 258–265 (2010)
M. Koel, Physical and chemical properties of ionic liquids based on the dialkylimidazolium cation. Proc. Estonian Acad. Sci. Chem. 49, 145–155 (2000)
H.W. Pennline, D.R. Luebke, K.L. Jones, C.R. Myers, B.I. Morsi, Y.J. Heintz, J.B. Ilconich, Progress in carbon dioxide capture and separation research for gasification-based power generation point sources. Fuel Process. Technol. 89, 897–907 (2008)
A. Finotello, J.E. Bara, D. Camper, R.D. Noble, Room-temperature ionic liquids: temperature dependence of gas solubility selectivity. Ind. Eng. Chem. Res. 47, 3453–3459 (2008)
J.L. Anderson, J.N.K. Dixon, J.F. Brennecke, Solubility of CO2, CH4, C2H6, C2H4, O2, and N2 in 1-Hexyl-3-methylpyridinium Bis (trifluoromethylsulfonyl) imide: comparison to other ionic liquids. Acc. Chem. Res. 40, 1208–1216 (2007)
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Acknowledgment: The authors are thankful to the Deanship of Scientific Research at Najran University for funding this work under the Research Groups Funding program grant code (NU/RG/SERC/12/5).
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Ziyada, A.K., Osman, A., Elbashir, A.A. et al. Exploring the Effect of Different Anions and Cations on the Solubility of CO2 in Nitrile Imidazolium-Based Ionic Liquids with Sulfonated-Based Anions. Korean J. Chem. Eng. 41, 1791–1803 (2024). https://doi.org/10.1007/s11814-024-00127-z
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DOI: https://doi.org/10.1007/s11814-024-00127-z