Determination of Extractant Solubility in Ionic Liquids by Thermogravimetric Analysis

References

• Rout, A.; Venkatesan, K. A.; Srinivasan, T. G.; Vasudeva Rao, P. R. Extraction of Americium (III) from Nitric Acid Medium by CMPO-TBP Extractants in Ionic Liquid Diluent. Radiochim. Acta. 2009, 97, 719–725. DOI: 10.1524/ract.2009.1675.
   Web of Science ®Google Scholar
• Sengupta, A.; Murali, M. S. Effect of Phase Modifiers TBP and Iso-Decanol on the Extraction and Complexation of Eu3+ with CMPO. Sep. Sci. Technol. 2016, 51, 2153–2163. DOI: 10.1080/01496395.2016.1201508.
   Web of Science ®Google Scholar
• Shimojo, K.; Aoyagi, N.; Saito, T.; Okamura, H.; Kubota, F.; Goto, M.; Naganawa, H. Highly Efficient Extraction Separation of Lanthanides Using Diglycol Amic Acid Extractant. Anal. Sci. 2014, 30, 263–269.
   PubMed Web of Science ®Google Scholar
• Laventine, D. M.; Afsar, A.; Hudson, M. J.; Harwood, L. M. Tuning the Solubilities of Bis-Triazinylphenanthroline Ligands (Btphens) and Their Complexes. Heterocycles 2012, 86, 1419–1429. DOI: 10.3987/COM-12-S(N)102.
   Web of Science ®Google Scholar
• Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Room- Temperature Ionic Liquids as Novel Media for ‘Clean’ Liquid-Liquid Extraction. Chem. Comm. 1998, 16, 1765–1766. DOI: 10.1039/A803999B.
   Web of Science ®Google Scholar
• Rogers, R. D.; Seddon, K. R. Ionic Liquids: Solvents of the Future. Science 2003, 302, 792–793. DOI: 10.1126/science.1090313.
   PubMed Web of Science ®Google Scholar
• Luo, H.; Huang, J.; Dai, S. Studies on Thermal Properties of Selected Aprotic and Protic Ionic Liquids. Sep. Sci. Technol. 2008, 43, 2473–2488. DOI: 10.1080/01496390802151922.
   Web of Science ®Google Scholar
• Wang, H.; Gurau, G.; Rogers, R. D. Ionic Liquid Processing of Cellulose. Chem. Soc. Rev. 2012, 41, 1519–1537. DOI: 10.1039/c2cs15311d.
   PubMed Web of Science ®Google Scholar
• Schröder, C.;. Proteins in Ionic Liquids: Current Status of Experiments and Simulations. Topics Curr. Chem. 2017, 375, 1–26. DOI: 10.1007/s41061-017-0110-2.
   Web of Science ®Google Scholar
• Viell, J.; Marquardt, W. Disintegration and Dissolution Kinetics of Wood Chips in Ionic Liquids. Holzforschung 2011, 65, 519–525. DOI: 10.1515/hf.2011.072.
   Web of Science ®Google Scholar
• Winterton, N.;. Solubilization of Polymers in Ionic Liquids. J. Mater. Chem. 2006, 16, 4281–4293. DOI: 10.1039/b610143g.
   Web of Science ®Google Scholar
• Idris, A.; Vijayaraghavan, R.; Rana, U. A.; Patti, F.; MacFarlane, D. R. Dissolution and Regeneration of Wool Keratin in Ionic Liquids. Green Chem. 2014, 16, 2857–2864. DOI: 10.1039/C4GC00213J.
   Web of Science ®Google Scholar
• Fort, D. A.; Swatloski, R. P.; Moyna, P.; Rogers, R. D.; Moyna, G. Use of Ionic Liquids in the Study of Fruit Ripening by High-Resolution 13C-NMR Spectroscopy: ‘Green’ Solvents Meet Green Bananas. Chem. Comm. 2006, 7, 714–716. DOI: 10.1039/b515177p.
   Google Scholar
• Shimojo, K.; Goto, M. First Application of Calixarenes as Extractants in Room-Temperature Ionic Liquids. Chem. Lett. 2004, 33, 320–321. DOI: 10.1246/cl.2004.320.
   Web of Science ®Google Scholar
• Shimojo, K.; Goto, M. Solvent Extraction and Stripping of Silver Ions in Room-Temperature Ionic Liquids Containing Calixarenes. Anal. Chem. 2004, 76, 5039–5044. DOI: 10.1021/ac049549x.
   PubMed Web of Science ®Google Scholar
• Kubota, F.; Goto, M. Application of Ionic Liquids to Solvent Extraction. Solv. Extr. Res. Dev. 2006, 13, 23–36.
   Web of Science ®Google Scholar
• Hawkins, C. A.; Momen, M. A.; Garvey, S.; Kestell, J.; Kaminski, M. D.; Dietz, M. L. Evaluation of Solid-Supported Room-Temperature Ionic Liquids Containing Crown Ethers as Media for Metal Ion Separation and Preconcentration. Talanta 2015, 135, 115–123. DOI: 10.1016/j.talanta.2014.12.019.
   PubMed Web of Science ®Google Scholar
• Luo, H.; Dai, S.; Bonnesen, P. V.; Buchanan, A. C.; Holbrey, J. D.; Bridges, N. J.; Rogers, R. D. Extraction of Cesium Ions from Aqueous Solutions Using Calix[4]Arene-Bis(Tert-Octylbenzo-Crown-6) in Ionic Liquids. Anal. Chem. 2004, 76, 3078–3083. DOI: 10.1021/ac049949k.
   PubMed Web of Science ®Google Scholar
• Tsuda, T.; Hussey, C. L.; Luo, H.; Dai, S. Recovery of Cesium Extracted from Simulated Tank Waste with an Ionic Liquid: Water and Oxygen Effects. J. Electrochem. Soc. 2006, 153, D171–D176. DOI: 10.1149/1.2337001.
   Web of Science ®Google Scholar
• Sun, X.; Bell, J. R.; Luo, H.; Dai, S. Extraction Separation of Rare-Earth Ions via Competitive Ligand Complexations between Aqueous and Ionic-Liquid Phases. Dalton Trans. 2011, 40, 8019–8023. DOI: 10.1039/c1dt10873e.
   PubMed Web of Science ®Google Scholar
• Sun, X.; Luo, H.; Dai, S. Solvent Extraction of Rare-Earth Ions Based on Functionalized Ionic Liquids. Talanta 2012, 90, 132–137. DOI: 10.1016/j.talanta.2011.12.069.
   PubMed Web of Science ®Google Scholar
• Buschmann, H.; Cleve, E.; Denter, U.; Schollmeyer, E. Determination of Complex Stabilities with Nearly Insoluble Host Molecules. Part II. Complexation of Alkali and Alkaline Earth Metal Cations with Dibenzo Crown Ethers in Aqueous Solution. J. Phys. Chem. 1997, 10, 781–785.
   Web of Science ®Google Scholar
• Mesmin, C.; Liljenzin, J.-O. Determination of H2TPTZ22+ Stability Constant by TPTZ Solubility in Nitric Acid. Solv. Extr. Ion Exch. 2003, 21, 783–795. DOI: 10.1081/SEI-120025922.
   Web of Science ®Google Scholar
• Ohto, K.; Tanaka, H.; Ishibashi, H.; Inoue, K. Solubility in Organic Diluents and Extraction Behavior of Calix[4]Arene Carboxylates with Different Alkyl Chains. Solv. Extr. Ion Exch. 1999, 17, 1309–1325. DOI: 10.1080/07366299908934650.
   Web of Science ®Google Scholar
• Engle, N. L.; Bonnesen, P. V.; Tomkins, B. A.; Haverlock, T. J.; Moyer, B. A. Synthesis and Properties of Calix[4]Arene-Bis[4-(2-Ethylhexyl)Benzo-Crown-6], A Cesium Extractant with Improved Stability. Solv. Extr. Ion Exch. 2004, 22, 611–636. DOI: 10.1081/SEI-120039639.
   Web of Science ®Google Scholar
• Principe, F.; Demopoulos, G. P. The Solubility and Stability of Organophosphoric Acid Extractants in H2SO4 and HCl Media. Hydrometallurgy 2003, 68, 115–124. DOI: 10.1016/S0304-386X(02)00206-2.
   Web of Science ®Google Scholar
• Naganawa, H.; Shimojo, K.; Mitamura, H.; Sugo, Y.; Noro, J.; Goto, M. A New “Green” Extractant of the Diglycol Amic Acid Type for Lanthanides. Solv. Extr. Res. Dev. 2007, 14, 151–159.
   Web of Science ®Google Scholar
• Williams, N. J.; Bryanstev, V. S.; Custelcean, R.; Seipp, C. A.; Moyer, B. A. α,α′,α′′,α′′′-meso-tetrahexyltetramethyl-calix[4]pyrrole: An Easy-To-Prepare Isomerically-Pure Anion Extractant with Enhanced Solubility in Organic Solvents. Supramol. Chem. 2016, 28, 176–187. DOI: 10.1080/10610278.2015.1120873.
   Web of Science ®Google Scholar
• Deetlefs, M.; Seddon, K. Improved Preparation of Ionic Liquids Using Microwave Synthesis. Green Chem. 2003, 5, 181–186. DOI: 10.1039/b300071k.
   Web of Science ®Google Scholar
• Fredlake, C. P.; Crosthwaite, J. M.; Hert, D. G.; Aki, S. N. V. K.; Brennecke, J. F. Thermophysical Properties of Imidazolium-Based Ionic Liquids. J. Chem. Eng. Data 2004, 49, 954–964. DOI: 10.1021/je034261a.
   Web of Science ®Google Scholar
• Kilaru, P.; Baker, G. A.; Scovazzo, P. Density and Surface Tension Measurements of Imidazolium-, Quaternary Phosphonium-, and Ammonium-Based Room-Temperature Ionic Liquids: Data and Correlation. J. Chem. Eng. Data 2007, 52, 2306–2314. DOI: 10.1021/je7003098.
   Web of Science ®Google Scholar
• Awad, W. H.; Gilman, J. W.; Nyden, M.; Harris, R. H.; Sutto, T. E.; Callahan, J.; Trulove, P. C.; DeLong, H. C.; Fox, D. M. Thermal Degradation Studies of Alkyl-Imidazolium Salts and Their Application in Nanocomposites. Thermochim. Acta 2004, 409, 3–11. DOI: 10.1016/S0040-6031(03)00334-4.
   Web of Science ®Google Scholar
• Partridge, J. A.; Jensen, R. C. Purification of Di-(2-Ethylhexyl)Phosphoric Acid by Precipitation of Copper (II) Di-(2-Ethylhexyl) Phosphate. J. Inorg. Nucl. Chem. 1969, 31, 2587–2589. DOI: 10.1016/0022-1902(69)80591-9.
   Web of Science ®Google Scholar
• Dietz, M. L.; Felinto, C.; Rhoads, S.; Clapper, M.; Finch, J. W.; Hay, B. P. Comparison of Column Chromatographic and Precipitation Methods for the Purification of a Macrocyclic Polyether Extractant. Sep. Sci. Technol. 1999, 34, 2943–2956. DOI: 10.1081/SS-100100814.
   Web of Science ®Google Scholar
• Gatrone, R. C.; Kaplan, L.; Horwitz, E. P. The Synthesis and Purification of the Carbamoylmethylphosphine Oxides. Solv. Extr. Ion Exch. 1987, 5, 1075–1116. DOI: 10.1080/07366298708918611.
   Web of Science ®Google Scholar
• Chin, A.; Carrick, J. D. Modular Approaches to Diversified Soft Lewis Basic Complexants through Suzuki-Miyaura Cross-Coupling of Bromoheteroarenes with Organotrifluoroborates. J. Org. Chem. 2016, 81, 1106–1115. DOI: 10.1021/acs.joc.5b02662.
   PubMed Web of Science ®Google Scholar
• Ngo, H. L.; LeCompte, K.; Hargens, L.; McEwen, A. B. Thermal Properties of Imidazolium Ionic Liquids. Thermochim. Acta 2000, 357-358, 97–102. DOI: 10.1016/S0040-6031(00)00373-7.
   Web of Science ®Google Scholar
• Aparicio, S.; Atilhan, M.; Karadas, F. Thermophysical Properties of Pure Ionic Liquids: Review of Present Situation. Ind. Eng. Chem. Res. 2010, 49, 9580–9595. DOI: 10.1021/ie101441s.
   Web of Science ®Google Scholar
• Baranyai, K. J.; Deacon, G. B.; MacFarlane, D. R.; Pringle, J. M.; Scott, J. L. Thermal Degradation of Ionic Liquids at Elevated Temperatures. Aust. Chem. J. 2004, 57, 145–147. DOI: 10.1071/CH03221.
   Web of Science ®Google Scholar
• Maton, C.; De Vos, N.; Stevens, C. V. Ionic Liquid Thermal Stabilities: Decomposition Mechanisms and Analysis Tools. Chem. Soc. Rev. 2013, 42, 5963–5977. DOI: 10.1039/c3cs60071h.
   PubMed Web of Science ®Google Scholar
• Van Valkenburg, M. E.; Vaughn, R. L.; Williams, M.; Wilkes, J. S. Thermochemistry of Ionic Liquid Heat-Transfer Fluids. Thermochim. Acta 2005, 425, 181–188. DOI: 10.1016/j.tca.2004.11.013.
   Web of Science ®Google Scholar
• Tokuda, H.; Hayamizu, K.; Ishii, K.; Susan, M. A. B. H.; Watanabe, M. Physicochemical Properties and Structures of Room-Temperature Ionic Liquids. 2. Variation of Alkyl Chain Length in Imidazolium Cation. J. Phys. Chem. B. 2005, 109, 6103–6110. DOI: 10.1021/jp044626d.
   PubMed Web of Science ®Google Scholar
• Chen, Y.; Chen, C.; Su, C.; Liaw, H. Auto-Ignition Characteristics of Selected Ionic Liquids. Procedia Eng. 2014, 84, 285–292. DOI: 10.1016/j.proeng.2014.10.436.
   Google Scholar
• Fox, D. M.; Gilman, J. W.; De Long, H. C.; Trulove, P. C.; Decomposition, T. G. A. Kinetics of 1-Butyl-2,3-Dimethylimidazolium Tetrafluoroborate and the Thermal Effects of Contaminants. J. Chem. Thermo. 2005, 37, 900–905. DOI: 10.1016/j.jct.2005.04.020.
   Web of Science ®Google Scholar
• Kamavaram, V.; Reddy, R. G. Thermal Stabilities of Dialkylimidazolium Chloride Ionic Liquids. Int. J. Therm. Sci. 2008, 47, 773–777. DOI: 10.1016/j.ijthermalsci.2007.06.012.
   Web of Science ®Google Scholar
• Fox, E. B.; Visser, A. E.; Bridges, N. J.; Amoroso, J. W. Thermophysical Properties of Nanoparticle-Enhanced Ionic Liquids (Neils) Heat-Transfer Fluids. Energy Fuels 2013, 27, 3385–3393. DOI: 10.1021/ef4002617.
   Web of Science ®Google Scholar
• Pawlak, A. J.; Dietz, M. L. Thermal Properties of Macrocyclic Polyethers: Implications for the Design of Crown Ether-Based Ionic Liquids. Sep. Sci. Technol. 2014, 49, 2847–2855. DOI: 10.1080/01496395.2014.946146.
   Web of Science ®Google Scholar
• Chattopadhyay, D. K.; Webster, D. C. Thermal Stability and Flame Retardancy of Polyurethanes. Prog. Polym. Sci. 2009, 34, 1068–1133. DOI: 10.1016/j.progpolymsci.2009.06.002.
   Web of Science ®Google Scholar
• Bhattacharya, S.; Subramanian, M.; Hiremath, U. S. Surfactant Lipids Containing Aromatic Units Produce Vesicular Membranes with High Thermal Stability. Chem. Phys. Lipids 1995, 78, 177–188.
   PubMed Web of Science ®Google Scholar
• Bradaric, C. J.; Downard, A.; Kennedy, C.; Robertson, A. J.; Zhou, Y. Industrial Preparation of Phosphonium Ionic Liquids. Green Chem. 2003, 5, 143–152.
   Web of Science ®Google Scholar