Reactive and Reversible Ionic Liquids for CO₂ Capture and Acid Gas Removal

REFERENCES

• NETL DOE/NETL Advanced Carbon Dioxide Capture R&D Program: Technology Update 9/2010. www.netl.doe.gov/technologies/coalpower/ewr/pubs/CO2%20Capture%20Tech%20Update%20Final.pdf (Accessed 14 June 2011)
   Google Scholar
• Rochelle , G.T. ( 2009 ) Amine Scrubbing for CO2 capture . Science , 325 : 1652 – 1654 .
   PubMed Web of Science ®Google Scholar
• Astarita , G. ; Savage , D.W. ; Bisio , A. ( 1983 ) Gas Treating with Chemical Solvents . John Wiley and Sons : New Jersey .
   Google Scholar
• Kidnay , A.J. ; Parrish , W.R. 2006 Fundamentals of Natural Gas Processing ; CRC Press: Taylor and Francis Group: Boca Raton , FL .
   Google Scholar
• Jou , F.Y. ; Mather , A.E. ; Otto , F.D. ( 1995 ) The solubility of CO2 in a 30-mass-percent monoethanolamine solution . Can. J. Chem. Eng. , 73 , 140 – 147 .
   Web of Science ®Google Scholar
• Teng , T.T. ; Maham , Y. ; Hepler , L.G. ; Mather , A.E. ( 1994 ) Viscosity of Aqueous-solutions of N-methyldiethanolamine and of diethanolamine . J. Chem. Eng. Data , 39 , 290 – 293 .
   Web of Science ®Google Scholar
• Vrachnos , A. ; Kontogeorgis , G. ; Voutsas , E. ( 2006 ) Thermodynamic modeling of acidic gas solubility in aqueous solutions of MEA, MDEA and MEA-MDEA blends . Ind. Eng. Chem. Res. , 45 , 5148 – 5154 .
   Web of Science ®Google Scholar
• Weiland , R.H. ; Dingman , J.C. ; Cronin , D.B. ; Browning , G.J. ( 1998 ) Density and viscosity of some partially carbonated aqueous alkanolamine solutions and their blends . J. Chem. Eng. Data , 43 , 378 – 382 .
   Web of Science ®Google Scholar
• Xu , S. ; Wang , Y.-W. ; Otto , F.D. ; Mather , A.E. ( 1996 ) Kinetics of the reaction of carbon dioxide with 2-amino-2-methyl-1-propanol solutions . Chem. Eng. Sci. , 51 , 841 – 850 .
   Web of Science ®Google Scholar
• Bara , J.E. ; Carlisle , T.K. ; Gabriel , C.J. ; Camper , D. ; Finotello , A. ; Gin , D.L. ; Noble , R.D. ( 2009 ) Guide to CO2 separations in imidazolium-based room-temperature ionic liquids . Ind. Eng. Chem. Res. , 48 , 2739 – 2751 .
   Web of Science ®Google Scholar
• Anderson , J.L. ; Dixon , J.K. ; Maginn , E.J. ; Brennecke , J.F. ( 2006 ) Measurement of SO2 solubility in ionic liquids . J. Phys. Chem. B , 110 , 15059 – 15062 .
   PubMed Web of Science ®Google Scholar
• Shiflett , M.B. ; Drew , D.W. ; Cantini , R.A. ; Yokozeki , A. ( 2010 ) Carbon dioxide capture using ionic liquid 1-butyl-3-methylimidazolium Acetate . Energy Fuels , 24 , 5781 – 5789 .
   Web of Science ®Google Scholar
• Shiflett , M.B. ; Yokozeki , A. ( 2010 ) Chemical absorption of sulfur dioxide in room-temperature ionic liquids . Ind. Eng. Chem. Res. , 49 , 1370 – 1377 .
   Web of Science ®Google Scholar
• Karadas , F. ; Atilhan , M. ; Aparicio , S. ( 2010 ) Review on the use of ionic liquids (ILs) as alternative fluids for CO2 capture and natural gas sweetening . Energy Fuels , 24 : 5817 – 5828 .
   Web of Science ®Google Scholar
• Holbrey , J.D. ; Rogers , R.D. ; Mantz , R.A. ; Trulove , P.C. ; Cocalia , V.A. ; Visser , A.E. ; Anderson , J.L. ; Anthony , J.L. ; lsur , J.F. ; Maginn , E.J. ; Welton , T. ( 2008 ) Physicochemical properties . In onic liquids in synthesis , 2nd ed. ; Wasserscheid , P. ; Welton , T. , Eds. Wiley-VCH : Weinheim , Germany .
   Google Scholar
• Gardas , R.L. ; Coutinho , J.A. P. ( 2008 ) A group contribution method for viscosity estimation of ionic liqids . Fluid Phase Equilibr. , 266 : 195 – 201 .
   Web of Science ®Google Scholar
• Camper , D. ; Bara , J.E. ; Gin , D.L. ; Noble , R.D. ( 2008 ) Room-temperature ionic liquid-amine solutions: Tunable solvents for efficient and reversible capture of CO2 . Ind. Eng. Chem. Res. , 47 , 8496 – 8498 .
   Web of Science ®Google Scholar
• Bara, J.E.; Camper, D.E.; Gin, D.L.; Noble, R.D. (2010) Room-temperature ionic liquids and composite materials: Platform technologies for CO2 capture. Acc. Chem. Res., 43, 152–159.
   Google Scholar
• Bates, E.D.; Mayton, R.D.; Ntai, I.; Davis, J.H. (2002) CO2 capture by a task-specific ionic liquid. J. Am. Chem. Soc., 124, 926–927.
   Google Scholar
• Gutowski, K.E.; Maginn, E.J. (2008) Amine-functionalized task-specific ionic liquids: A mechanistic explanation for the dramatic increase in viscosity upon complexation with CO2 from molecular simulation. J. Am. Chem. Soc., 130, 14690–14704.
   Google Scholar
• Shiflett, M.B.; Kasprzak, D.J.; Junk, C.P.; Yokozeki, A. (2008) Phase behavior of {carbon dioxide plus bmim Ac} mixtures. J. Chem. Thermodyn. 40, 25–31.
   Google Scholar
• Carvalho, P.J.; Alvarez, V.H.; Schroder, B.; Gil, A.M.; Marrucho, I.M.; Aznar, M.; Santos, L.; Coutinho, J.A. P. (2009) Specific solvation interactions of CO2 on acetate and trifluoroacetate imidazolium based ionic liquids at high pressures. J. Phys. Chem. B, 113, 6803–6812.
   Google Scholar
• Zhou, S.; Chen, X.; Nguyen, T.; Voice, A.K.; Rochelle, G.T. (2010) Aqueous ethylenediamine for CO2 capture. Chemsuschem, 3, 913–918.
   Google Scholar
• Freeman, S.A.; Dugas, R.; Van Wagener, D.H.; Nguyen, T.; Rochelle, G.T. (2010) Carbon dioxide capture with concentrated, aqueous piperazine. Int. J. Greenh. Gas Con., 4, 119–124.
   Google Scholar
• Shannon, M.S.; Bara, J.E. (2011) Properties of alkylimidazoles as solvents for CO2 capture and comparisons to imidazolium-based ionic liquids. Ind. Eng. Chem. Res., 50, 8665–8677.
   Google Scholar
• NIST, Ionic Liquids Database (ILThermo) – NIST Standard Reference Database #147. http://ilthermo.boulder.nist.gov/ILThermo/mainmenu.uix (Accessed 14 June 2011).
   Google Scholar
• McCabe, W.L.; Smith, J.C.; Harriott, P. (2001) Unit Operations of Chemical Engineering, 6th ed.; McGraw-Hill: New York.
   Google Scholar
• Ohno, H.; Fukumoto, K. Amino acid ionic liquids. Acc. Chem. Res. 2007, 40, 1122–1129.
   Google Scholar
• Fukumoto, K.; Yoshizawa, M.; Ohno, H. (2005) Room temperature ionic liquids from 20 natural amino acids. J. Am. Chem. Soc., 127, 2398–2399.
   Google Scholar
• Gurkan, B.E.; de la Fuente, J.C.; Mindrup, E.M.; Ficke, L.E.; Goodrich, B.F.; Price, E.A.; Schneider, W.F.; Brennecke, J.F. (2010) Equimolar CO2 absorption by anion-functionalized ionic liquids. J. Am. Chem. Soc., 132, 2116–2117.
   Google Scholar
• Goodrich, B.F.; de la Fuente, J.C.; Gurkan, B.E.; Zadigian, D.J.; Price, E.A.; Huang, Y.; Brennecke, J.F. (2010) Experimental measurements of amine-functionalized anion-tethered ionic liquids with carbon dioxide. Ind. Eng. Chem. Res., 50, 111–118.
   Google Scholar
• Wang, C.M.; Luo, X.Y.; Luo, H.M.; Jiang, D.E.; Li, H.R.; Dai, S. (2011) Tuning the basicity of ionic liquids for equimolar CO2 capture. Angew. Chem. Int. Edit., 50, 4918–4922.
   Google Scholar
• Gurkan, B.; Goodrich, B.F.; Mindrup, E.M.; Ficke, L.E.; Massel, M.; Seo, S.; Senftle, T.P.; Wu, H.; Glaser, M.F.; Shah, J.K.; Maginn, E.J.; Brennecke, J.F.; Schneider, W.F. (2010) Molecular design of high capacity, low viscosity, chemically tunable ionic liquids for CO2 capture. J. Phys. Chem. Lett., 1, 3494–3499.
   Google Scholar
• McGuinness, D.S.; Cavell, K.J.; Yates, B.F.; Skelton, B.W.; White, A.H. (2001) Oxidative addition of the imidazolium cation to zerovalent Ni, Pd, and Pt: a combined density functional and experimental study. J. Am. Chem. Soc., 123, 8317–8328.
   Google Scholar
• Wang, C.; Luo, H.; Luo, X.; Li, H.; Dai, S. (2010) Equimolar CO2 capture by imidazolium-based ionic liquids and superbase systems. Green Chem., 12, 2019–2023.
   Google Scholar
• Wang, C.M.; Luo, H.M.; Jiang, D.E.; Li, H.R.; Dai, S. (2010) Carbon dioxide capture by superbase-derived protic ionic liquids. Angew. Chem. Int. Edit., 49, 5978–5981.
   Google Scholar
• Blasucci, V.; Hart, R.; Mestre, V.L.; Hahne, D.J.; Burlager, M.; Huttenhower, H.; Thio, B.J. R.; Pollet, P.; Liotta, C.L.; Eckert, C.A. (2010) Single component, reversible ionic liquids for energy applications. Fuel, 89, 1315–1319.
   Google Scholar
• Blasucci, V.; Dilek, C.; Huttenhower, H.; John, E.; Llopis-Mestre, V.; Pollet, P.; Eckert, C.A.; Liotta, C.L. (2009) One-component, switchable ionic liquids derived from siloxylated amines. Chem. Commun., 116–118.
   Google Scholar
• Blasucci, V.M.; Hart, R.; Pollet, P.; Liotta, C.L.; Eckert, C.A. (2010) Reversible ionic liquids designed for facile separations. Fluid Phase Equilibr., 294, 1–6.
   Google Scholar
• Hart, R.; Pollet, P.; Hahne, D.J.; John, E.; Llopis-Mestre, V.; Blasucci, V.; Huttenhower, H.; Leitner, W.; Eckert, C.A.; Liotta, C.L. (2010) Benign coupling of reactions and separations with reversible ionic liquids. Tetrahedron, 66, 1082–1090.
   Google Scholar
• Rainbolt, J.E.; Koech, P.K.; Yonker, C.R.; Zheng, F.; Main, D.; Weaver, M.L.; Linehan, J.C.; Heldebrant, D.J. (2011) Anhydrous tertiary alkanolamines as hybrid chemical and physical CO2 capture reagents with pressure-swing regeneration. Energ. Environ. Sci., 4, 480–484.
   Google Scholar
• Heldebrant, D.J.; Koech, P.K.; Rainbolt, J.E.; Zheng, F. (2011) CO2 -binding organic liquids, an integrated acid gas capture system. Energy Procedia, 4, 216–223.
   Google Scholar
• Koech, P.K.; Rainbolt, J.E.; Bearden, M.D.; Zheng, F.; Heldebrant, D.J. (2011) Chemically selective gas sweetening without thermal-swing regeneration. Energ. Environ. Sci., 4, 1385–1390.
   Google Scholar
• Jessop, P.G.; Heldebrant, D.J.; Li, X.; Eckert, C.A.; Liotta, C.L. (2005) Green chemistry: Reversible nonpolar-to-polar solvent. Nature, 436, 1102.
   Google Scholar
• Yamada, T.; Lukac, P.J.; George, M.; Weiss, R.G. (2007) Reversible, room-temperature ionic liquids. Amidinium carbamates derived from amidines and aliphatic primary amines with carbon dioxide. Chem. Mater., 19, 967–969.
   Google Scholar
• Yamada, T.; Lukac, P.J.; Yu, T.; Weiss, R.G. Reversible, room-temperature, chiral ionic liquids. Amidinium carbamates derived from amidines and amino-acid esters with carbon dioxide. Chem. Mater. 2007, 19, 4761–4768.
   Google Scholar
• Yu, T.; Yamada, T.; Gaviola, G.C.; Weiss, R.G. (2008) Carbon dioxide and molecular nitrogen as switches between ionic and uncharged room-temperature liquids comprised of amidines and chiral amino alcohols. Chem. Mater., 20, 5337–5344.
   Google Scholar
• Yu, T.; Yamada, T.; Weiss, R.G. (2010) In situ formation of thermally stable, room-temperature ionic liquids from CS2 and amidine/amine mixtures. Chem. Mater., 22, 5492–5499.
   Google Scholar
• Lenarcik, B.; Ojczenasz, P. (2002) The influence of the size and position of the alkyl groups in alkylimidazole molecules on their acid-base properties. J. Heterocyclic Chem., 39, 287–290.
   Google Scholar
• Palleros, D. Heterocycles. www.chemistry.ucsc.edu/courses/palleros/Heterocycles.pdf (Accessed 31 May 2011)
   Google Scholar