Partition of substituted benzenes between hydrophobic ionic liquids and water: Evaluation of interactions between substituents and ionic liquids

Journal of Chemical and Engineering Data

Volumn 56, Issue 5, 2011, Pages 2160-2167

  Nakamura, Ko Ichi ^a   Kudo, Yoshihiro ^a   Takeda, Yasuyuki ^a   Katsuta, Shoichi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1-BUTYL-3-METHYL-IMIDAZOLIUM HEXAFLUOROPHOSPHATE; 1-OCTANOL; ACCEPTOR PROPERTIES; ACETOPHENONES; BENZOIC ACID; BENZONITRILES; BENZYL ALCOHOL; HYDROPHOBIC IONIC LIQUID; MOLAR VOLUMES; P-VALUES; PARTITION COEFFICIENT; POLAR SUBSTITUENTS; REGULAR SOLUTION THEORY; SOLUBILITY PARAMETERS; SPECIFIC INTERACTION; SUBSTITUTED BENZENES;

AMIDES; BENZENE; CARBOXYLIC ACIDS; EXTRACTION; HYDROPHOBICITY; IONS; KETONES; ORGANIC POLYMERS; PHENOLS; TERNARY SYSTEMS; WATERWORKS;

IONIC LIQUIDS;

EID: 79956161156     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je101215x     Document Type: Article

References (41)

1. Liu, J.; Jönsson, J. Å.; Jiang, G. Application of Ionic Liquids in Analytical Chemistry Trends Anal. Chem. 2005, 24, 20-27 (Pubitemid 40082725)
2. Sun, P.; Armstrong, D. W. Ionic Liquids in Analytical Chemistry Anal. Chim. Acta 2010, 661, 1-16
3. Poole, C. F.; Poole, S. K. Extraction of Organic Compounds with Room Temperature Ionic Liquids J. Chromatogr., A 2010, 1217, 2268-2286
4. Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. N.; Rogers, R. D. Room Temperature Ionic Liquids as Novel Media for 'Clean' Liquid-Liquid Extraction Chem. Commun. 1998, 1765-1766 (Pubitemid 128675787)
5. Carda-Broch, S.; Berthod, A.; Armstrong, D. W. Solvent Properties of the 1-Butyl-3-methylimidazolium Hexafluorophosphate Ionic Liquid Anal. Bioanal. Chem. 2003, 375, 191-199 (Pubitemid 41201294)
6. Khachatryan, K. S.; Smirnova, S. V.; Torocheshnikova, I. I.; Shvedene, N. V.; Formanovsky, A. A.; Pletnev, I. V. Solvent Extraction and Extraction-Voltammetric Determination of Phenols Using Room Temperature Ionic Liquid Anal. Bioanal. Chem. 2005, 381, 464-470 (Pubitemid 40249169)
7. Inoue, G.; Shimoyama, Y.; Su, F.; Takada, S.; Iwai, Y.; Arai, Y. Measurements and Correlation of Partition Coefficients for Phenolic Compounds in the 1-Butyl-3-methylimidazolium Hexafluorophosphate/Water Two-Phase System J. Chem. Eng. Data 2007, 52, 98-101
8. Shimoyama, Y.; Ikeda, K.; Su, F.; Iwai, Y. Effect of Isomers on Partition Coefficients for Phenolic Compounds in the 1-Butyl-3-methylimidazolium Hexafluorophosphate + Water Two-Phase System J. Chem. Eng. Data 2010, 55, 3151-3154
9. McFarlane, J.; Ridenour, W. B.; Luo, H.; Hunt, R. D.; DePaoli, D. W.; Ren, R. X. Room Temperature Ionic Liquids for Separating Organics from Produced Water Sep. Sci. Technol. 2005, 40, 1245-1265 (Pubitemid 40607385)
10. Holbrey, J. D.; Lopez-Martin, I.; Rothenberg, G.; Seddon, K. R.; Silvero, G.; Zheng, X. Desulfurisation of Oils Using Ionic Liquids: Selection of Cationic and Anionic Components to Enhance Extraction Efficiency Green Chem. 2008, 10, 87-92
11. Abraham, M. H.; Acree, W. E., Jr. Comparative Analysis of Solvation and Selectivity in Room Temperature Ionic Liquids Using the Abraham Linear Free Energy Relationship Green Chem. 2006, 8, 906-915 (Pubitemid 44527096)
12. Sprunger, L.; Clark, M.; Acree, W. E., Jr.; Abraham, M. H. Characterization of Room-Temperature Ionic Liquids by the Abraham Model with Cation-Specific and Anion-Specific Equation Coefficients J. Chem. Inf. Model. 2007, 47, 1123-1129 (Pubitemid 46973726)
13. Sprunger, L. M.; Proctor, A.; Acree, W. E., Jr.; Abraham, M. H. LFER Correlations for Room Temperature Ionic Liquids: Separation of Equation Coefficients into Individual Cation-Specific and Anion-Specific Contributions Fluid Phase Equilib. 2008, 265, 104-111
14. Sprunger, L. M.; Gibbs, J.; Proctor, A.; Acree, W. E.; Abraham, M. H.; Meng, Y.; Cong, Y.; Anderson, J. L. Linear Free Energy Relationship Correlations for Room Temperature Ionic Liquids: Revised Cation-Specific and Anion-Specific Equation Coefficients for Predictive Applications Covering a Much Larger Area of Chemical Space Ind. Eng. Chem. Res. 2009, 48, 4145-4154
15. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley & Sons: New York, 1979.
16. Suzuki, N.; Yoshida, T.; Watarai, H. Partition Coefficients of Chlorobenzenes in Heptane-Water and Heptane-Acetonitrile Systems Bull. Chem. Soc. Jpn. 1982, 55, 121-125
17. de Ligny, C. L.; Kreutzer, H. J. H.; Visserman, G. F. Steric Effects of Methyl Groups on the Ionization Constants of Phenols and Anilines Rec. Trav. Chim. 1966, 85, 5-14
18. Katsuta, S.; Saitoh, K. Control of Separation Selectivity in Micellar Electrokinetic Chromatography by Modification of the Micellar Phase with Solubilized Organic Compounds J. Chromatogr., A 1997, 780, 165-178 (Pubitemid 27395724)
19. Fujita, T.; Iwasa, J.; Hansch, C. A New Substituent Constant, π, Derived from Partition Coefficients J. Am. Chem. Soc. 1964, 86, 5175-5180
20. Watarai, H.; Tanaka, M.; Suzuki, N. Determination of Partition Coefficients of Halobenzenes in Heptane/Water and 1-Octanol/Water Systems and Comparison with the Scaled Particle Calculation Anal. Chem. 1982, 54, 702-705
21. Hogben, C.; Tocco, D.; Brodie, B.; Schanker, L. On the Mechanism of Intestinal Absorption of Drugs J. Pharmacol. Exp. Ther. 1959, 125, 275-282
22. Collander, R. The Distribution of Organic Compounds between Ether and Water Acta Chem. Scand. 1949, 3, 717-747
23. Sandell, K. B. The Distribution of Organic Compounds between Water and Organic Solvents Monatsh. Chem. 1958, 89, 36-53
24. Lindberg, J. J. The Relation between the Distribution in Ether and Water and the Infrared Spectrum of Several Guaiacyl and Syringyl Compounds Soc. Sci. Fennica, Comment. Phys.-Math. 1958, 21, 1-13
25. Hildebrand, J. H. A Critique of the Theory of Solubility of Non-Electrolytes Chem. Rev. 1949, 44, 37-45
26. Katsuta, S.; Shiozawa, Y.; Kudo, Y.; Takeda, Y. Stability of Ion Pairs of Bis(trifluoromethanesulfonyl)amide-Based Ionic Liquids in Dichloromethane J. Chem. Eng. Data 2010, 55, 1588-1593
27. Lopes, J. N. C.; Cordeiro, T. C.; Esperança, J. M. S. S.; Guedes, H. J. R.; Huq, S.; Rebelo, L. P. N.; Seddon, K. R. Deviations from Ideality in Mixtures of Two Ionic Liquids Containing a Common Ion J. Phys. Chem. B 2005, 109, 3519-3525 (Pubitemid 40352321)
28. Abboud, J.-L. M.; Notario, R. Critical Compilation of Scales of Solvent Parameters. Part I. Pure, Non-Hydrogen Bond Donor Solvents Pure Appl. Chem. 1999, 71, 645-718
29. Jin, H.; O'Hare, B.; Dong, J.; Arzhantsev, S.; Baker, G. A.; Wishart, J. F.; Benesi, A. J.; Maroncelli, M. Physical Properties of Ionic Liquids Consisting of the 1-Butyl-3-Methylimidazolium Cation with Various Anions and the Bis(trifluoromethylsulfonyl)imide Anion with Various Cations J. Phys. Chem. B 2008, 112, 81-92 (Pubitemid 351169885)
30. Katsuta, S.; Ishitani, T.; Suzuki, M.; Ishii, Y.; Kudo, Y.; Takeda, Y. Equilibrium Studies on Ion-Pair Formation in Water and Distribution between Water and m -Xylene of Tetraalkylammonium Picrates J. Solution Chem. 2004, 33, 437-451 (Pubitemid 39158515)
31. Katsuta, S.; Wakabayashi, H.; Tamaru, M.; Kudo, Y.; Takeda, Y. Tetraalkylammonium Picrates in the Dichloromethane-Water System: Ion-Pair Formation and Liquid-Liquid Distribution of Free Ions and Ion Pairs J. Solution Chem. 2007, 36, 531-547
32. Katsuta, S.; Yamaguchi, N.; Ogawa, R.; Kudo, Y.; Takeda, Y. Distribution of 1-Alkyl-3-methylimidazolium Ions and Their Ion Pairs between Dichloromethane and Water Anal. Sci. 2008, 24, 1264-1267
33. Hansen, C. M.; Beerbower, A. Kirk-Othmer Encyclopedia of Chemical Technology; Standen, A., Ed.; Interscience: New York, 1971; pp 889 - 910 (Suppl. Vol.).
34. Mottola, H. A.; Freiser, H. Distribution of Certain 8-Quinolinols and Their Copper(II) Chelates in a Series of Organic Solvent-Aqueous Pairs Talanta 1966, 13, 55-65
35. Wakahayashi, T.; Oki, S.; Omori, T.; Suzuki, N. Some Applications of the Regular Solution Theory to Solvent Extraction. I. Distribution of β -Diketones J. Inorg. Nucl. Chem. 1964, 26, 2255-2264
36. Salminen, J.; Papaiconomou, N.; Kumar, R. A.; Lee, J.-M.; Kerr, J.; Newman, J.; Prausnitz, J. M. Physicochemical Properties and Toxicities of Hydrophobic Piperidinium and Pyrrolidinium Ionic Liquids Fluid Phase Equilib. 2007, 261, 421-426 (Pubitemid 47588683)
37. 16 J. Phys. Chem. 1963, 67, 776-779
38. Cabani, S.; Gianni, P.; Mollica, V.; Lepori, L. Group Contributions to the Thermodynamic Properties of Non-Ionic Organic Solutes in Dilute Aqueous Solution J. Solution Chem. 1981, 10, 563-595
39. Caselli, I.; Campanile, S.; Giolitti, A.; Molin, D. Theoretical Prediction of the Abraham Hydrogen Bond Acidity and Basicity Factors from a Reaction Field Method J. Chem. Inf. Model. 2005, 45, 327-333 (Pubitemid 40635338)
40. Reichardt, C. Solvatochromic Dyes as Solvent Polarity Indicators Chem. Rev. 1994, 94, 2319-2538
41. Tokuda, H.; Tsuzuki, S.; Susan, M. A. B. H.; Hayamizu, K.; Watanabe, M. How Ionic Are Room-Temperature Ionic Liquids? An Indicator of the Physicochemical Properties J. Phys. Chem. B 2006, 110, 19593-19600 (Pubitemid 44626443)