Ditetraalkylammonium amino acid ionic liquids as CO₂ absorbents of high capacity.

By grafting butyl or ethyl onto tetramethylethylenediamine, quaternary ammonium salts with two positive charge centers were formed at the first step. Metathesis with Ag(2)O followed. Through neutralization with glycine, l-alanine, or valine, a series of new ditetraalkylammonium amino acid ionic liquids (DILs) for CO(2) capture were generated. The structures of DILs, as shown in Figure 1, were verified by using (1)H NMR and EA. These DILs were found to be of quite high viscosity which militated against their industrial application in CO(2) removal. Drawing on the experience of mixed amines' aqueous solutions, these DILs were blended with water or N-methyldiethanolamine (MDEA) aqueous solutions to act as special absorbents of CO(2). Using a Double-Tank Absorption System, the absorption performance of these DIL solutions was investigated in detail. The experimental results indicated that among the three aqueous solutions of DILs (20%, 40%, and 80 wt %), the solution of 40% DIL had a higher absorption rate of CO(2) than the other two, demonstrating the different effects of concentration and viscosity on the absorption. The solution of 40% DIL or the 15% DIL + 15% MDEA had much higher capacity for CO(2) than the corresponding monocation tetraalkylammonium AAILs, due to the special structure of the dication which could influence the solubility of CO(2) in the aqueous solution.

[1]  William F. Schneider,et al.  Molecular Design of High Capacity, Low Viscosity, Chemically Tunable Ionic Liquids for CO2 Capture , 2010 .

[2]  Zhang Feng,et al.  Absorption of CO2 in the aqueous solutions of functionalized ionic liquids and MDEA , 2010 .

[3]  S. Icli,et al.  Dicationic bis-imidazolium molten salts for efficient dye sensitized solar cells: Synthesis and photovoltaic properties , 2009 .

[4]  B. Bhushan,et al.  Molecularly thick dicationic ionic liquid films for nanolubrication , 2009 .

[5]  Junhua Huang,et al.  Why are Ionic Liquids Attractive for CO2 Absorption? An Overview , 2009 .

[6]  Xiangping Zhang,et al.  Dual amino-functionalised phosphonium ionic liquids for CO2 capture. , 2009, Chemistry.

[7]  José M. Navaza,et al.  Removal process of CO2 using MDEA aqueous solutions in a bubble column reactor , 2009 .

[8]  S. Tsang,et al.  Recent advances in CO2 capture and utilization. , 2008, ChemSusChem.

[9]  Li Yang,et al.  Asymmetrical dicationic ionic liquids based on both imidazolium and aliphatic ammonium as potential electrolyte additives applied to lithium secondary batteries , 2008 .

[10]  Zhuo Zeng,et al.  Polyfluoroalkyl, Polyethylene Glycol, 1,4-Bismethylenebenzene, or 1,4-Bismethylene-2,3,5,6-Tetrafluorobenzene Bridged Functionalized Dicationic Ionic Liquids: Synthesis and Properties as High Temperature Lubricants , 2008 .

[11]  Guannan Wang,et al.  Tetraalkylammonium amino acids as functionalized ionic liquids of low viscosity. , 2008, Chemical communications.

[12]  Tae Ho Kim,et al.  Novel thixotropic gel electrolytes based on dicationic bis-imidazolium salts for quasi-solid-state dye-sensitized solar cells , 2008 .

[13]  G. Versteeg,et al.  Characterization of potassium glycinate for carbon dioxide absorption purposes , 2007 .

[14]  D. Armstrong,et al.  PEG-linked geminal dicationic ionic liquids as selective, high-stability gas chromatographic stationary phases , 2007, Analytical and bioanalytical chemistry.

[15]  M. Aresta,et al.  Utilisation of CO2 as a chemical feedstock: opportunities and challenges. , 2007, Dalton transactions.

[16]  J. Brennecke,et al.  Improving carbon dioxide solubility in ionic liquids. , 2007, The journal of physical chemistry. B.

[17]  Hiroyuki Yasuda,et al.  Transformation of carbon dioxide. , 2007, Chemical reviews.

[18]  D. Armstrong,et al.  Dicationic ionic liquid stationary phase for GC-MS analysis of volatile compounds in herbal plants , 2007, Analytical and bioanalytical chemistry.

[19]  Li Yang,et al.  Ionic liquids based on aliphatic tetraalkylammonium dications and TFSI anion as potential electrolytes , 2007 .

[20]  Wei-min Liu,et al.  Synthesis of dicationic symmetrical and asymmetrical ionic liquids and their tribological properties as ultrathin films , 2007 .

[21]  Chunshan Song.  Global challenges and strategies for control, conversion and utilization of CO2 for sustainable development involving energy, catalysis, adsorption and chemical processing , 2006 .

[22]  Youqing Shen,et al.  Supported absorption of CO2 by tetrabutylphosphonium amino acid ionic liquids. , 2006, Chemistry.

[23]  Chengfeng Ye,et al.  Polyethylene glycol functionalized dicationic ionic liquids with alkyl or polyfluoroalkyl substituents as high temperature lubricants , 2006 .

[24]  R. Sheldon,et al.  Synthesis and application of dicationic ionic liquids , 2006 .

[25]  D. Armstrong,et al.  Immobilized ionic liquids as high-selectivity/high-temperature/high-stability gas chromatography stationary phases. , 2005, Analytical chemistry.

[26]  D. Armstrong,et al.  Using geminal dicationic ionic liquids as solvents for high-temperature organic reactions. , 2005, Organic letters.

[27]  A. Yokozeki,et al.  Solubilities and Diffusivities of Carbon Dioxide in Ionic Liquids: [bmim][PF6] and [bmim][BF4] , 2005 .

[28]  Masahiro Yoshizawa,et al.  Room temperature ionic liquids from 20 natural amino acids. , 2005, Journal of the American Chemical Society.

[29]  D. Armstrong,et al.  Structure and properties of high stability geminal dicationic ionic liquids. , 2005, Journal of the American Chemical Society.

[30]  J. Brennecke,et al.  High-Pressure Phase Behavior of Carbon Dioxide with Imidazolium-Based Ionic Liquids , 2004 .

[31]  M. Mimeault,et al.  Determination of the Structural Features of Distinct Amines Important for the Absorption of CO2 and Regeneration in Aqueous Solution , 2003 .

[32]  Gary T. Rochelle,et al.  Absorption of carbon dioxide in aqueous piperazine/methyldiethanolamine , 2002 .

[33]  Ioanna Ntai,et al.  CO(2) capture by a task-specific ionic liquid. , 2002, Journal of the American Chemical Society.

[34]  Sung Hyun Kim,et al.  Correlation and Prediction of the Solubility of Carbon Dioxide in Aqueous Alkanolamine and Mixed Alkanolamine Solutions , 2002 .

[35]  R. Weiss,et al.  Chemically reversible organogels: aliphatic amines as "latent" gelators with carbon dioxide. , 2001, Journal of the American Chemical Society.

[36]  J. E. Lyons,et al.  Catalysis research of relevance to carbon management: progress, challenges, and opportunities. , 2001, Chemical reviews.

[37]  Joan F. Brennecke,et al.  High-Pressure Phase Behavior of Ionic Liquid/CO2 Systems , 2001 .

[38]  Kaori Ito,et al.  Enhanced ion conduction in imidazolium-type molten salts , 2000 .

[39]  Dan Hancu,et al.  Green processing using ionic liquids and CO2 , 1999, Nature.

[40]  Y. Amenomiya.  Methanol synthesis from CO2 + H2 II. Copper-based binary and ternary catalysts , 1987 .

[41]  A. Schumpe,et al.  The estimation of gas solubilities in salt solutions , 1993 .