Partition behavior of chlorophenols and nitrophenols between hydrophobic ionic liquids and water

Journal of Chemical and Engineering Data

Volumn 56, Issue 11, 2011, Pages 4083-4089

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

^a CHIBA UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1-BUTYL-3-METHYL-IMIDAZOLIUM HEXAFLUOROPHOSPHATE; 1-OCTANOL; [BMIM][PF; ACID-DISSOCIATION CONSTANT; CHLOROPHENOLS; ELECTRON-PAIR; EXTRACTABILITY; HYDROPHOBIC CATIONS; HYDROPHOBIC IONIC LIQUID; INTERACTION ENERGIES; NITROPHENOLS; PARTITION BEHAVIORS; PARTITION COEFFICIENT; PH VALUE; PHENOLIC HYDROXYL GROUP; SUBSTITUENT EFFECT; TETRAFLUOROBORATES;

ALCOHOLS; AMIDES; DISSOCIATION; HYDROPHOBICITY; NEGATIVE IONS; PHENOLS;

IONIC LIQUIDS;

EID: 80955132310     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je200506p     Document Type: Article

References (33)

1. 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)
2. 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)
3. Poole, C. F.; Poole, S. K. Extraction of Organic Compounds with Room Temperature Ionic Liquids J. Chromatogr., A 2010, 1217, 2268-2286
4. Nakamura, K.; Kudo, Y.; Takeda, Y.; Katsuta, S. Partition of Substituted Benzenes between Hydrophobic Ionic Liquids and Water: Evaluation of Interactions between Substituents and Ionic Liquids J. Chem. Eng. Data 2011, 56, 2160-2167
5. Bekou, E.; Dionysiou, D. D.; Qian, R.-Y.; Botsaris, G. D. Extraction of Chlorophenols from Water Using Room Temperature Ionic Liquids ACS Symp. Ser. 2003, 856, 544-560
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. Measurement 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. - Based Ionic Liquids and Aqueous Solution Z. Phys. Chem. 2007, 221, 825-835
9. Egorov, V. M.; Smirnova, S. V.; Pletnev, I. V. Highly Efficient Extraction of Phenols and Aromatic Amines into Novel Ionic Liquids Incorporating Quaternary Ammonium Cation Sep. Purif. Technol. 2008, 63, 710-715
10. Ni, H.-Q.; Dong, J.; Shi, J.-J.; Wang, W. Ionic Liquid as Extraction Agent for Detection of Volatile Phenols in Wastewater and Its Regeneration J. Sep. Sci. 2010, 33, 1356-1359
11. 2N] Hydrophobic Ionic Liquids J. Phys. Chem. B 2008, 112, 1604-1610 (Pubitemid 351316360)
12. Freire, M. G.; Neves, C. M. S. S.; Carvalho, P. J.; Gardas, R. L.; Fernandes, A. M.; Marrucho, I. M.; Santos, L. M. N. B. F.; Coutinho, J. A. P. Mutual Solubilities of Water and Hydrophobic Ionic Liquids J. Phys. Chem. B 2007, 111, 13082-13089 (Pubitemid 350197634)
13. Anthony, J. L.; Maginn, E. J.; Brennecke, J. F. Solution Thermodynamics of Imidazolium-Based Ionic Liquids and Water J. Phys. Chem. B 2001, 105, 10942-10949
14. Fickling, M. M.; Fischer, A.; Mann, B. R.; Packer, J.; Vaughan, J. Hammett Substituent Constants for Electron-withdrawing Substituents: Dissociation of Phenols, Anilinium Ions and Dimethylanilinium Ions J. Am. Chem. Soc. 1959, 81, 4226-4230
15. Desai, A. G.; Milburn, R. M. Further Thermodynamic Studies of Iron(III)-Phenolate and Proton- Phenolate Associations J. Am. Chem. Soc. 1969, 91, 1958-1961
16. Murray, J. W.; Gordon, N. E. The Dissociation Constants of Some Chlorophenols J. Am. Chem. Soc. 1935, 57, 110-111
17. Xie, T. M.; Dyrssen, D. Simultaneous Determination of Partition Coefficients and Acidity Constants of Chlorinated Phenols and Guaiacols by Gas Chromatography Anal. Chim. Acta 1984, 160, 21-30
18. Fernandez, L. P.; Hepler, L. G. Heats and Entropies of Ionization of Phenol and Some Substituted Phenols J. Am. Chem. Soc. 1959, 81, 1783-1786
19. Bell, R. P.; Kuhn, A. T. Dissociation Constants of Some Acids in Deuterium Oxide Trans. Faraday Soc. 1963, 59, 1789-1793
20. Davis, M. M.; Paabo, M. Spectrophotometric Determination of the Thermodynamic p K Value of Picric Acid in Water at 25 °C J. Res. Natl. Bur. Stand. 1963, 67A, 241-246
21. Fujita, T.; Iwasa, J.; Hansch, C. A New Substituent Constant, π, Derived from Partition Coefficients J. Am. Chem. Soc. 1964, 86, 5175-5180
22. Xie, T. M.; Hulthe, B.; Folestad, S. Determination of Partition Coefficients of Chlorinated Phenols, Guaiacols and Catechols by Shake-Flask GC and HPLC Chemosphere 1984, 13, 445-459 (Pubitemid 14138522)
23. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley & Sons: New York, 1979.
24. 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)
25. Imura, H.; Katsuta, S.; Suzuki, N. Association of Tris(pentane-2,4- dionato)cobalt(III) with Chlorinated Phenols by Hydrogen Bonding Polyhedron 1991, 10, 1405-1409
26. Korenman, Ya. I. Distribution of Chlorophenols between Organic Solvents and Water Zh. Prikl. Khim. 1974, 47, 2079-2083
27. Korenman, Ya. I.; Kotelyanskaya, E. B.; Nefedova, T. A. Extraction of Mononitrophenols from Aqueous Solutions Zh. Prikl. Khim. 1976, 49, 1112-1114
28. 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)
29. Gutmann, V. The Donor-Acceptor Approach to Molecular Interactions; Plenum Press: New York, 1978.
30. Kanevskii, E. A.; Zarubin, A. I.; Pavlovskaya, G. R.; Rengevich, V. B.; Volnukhina, A. V. Donor Numbers of Aliphatic Alcohols Zh. Obshch. Khim. 1975, 45, 130-132
31. Oldham, W. J., Jr.; Costa, D. A.; Smith, W. H. Development of Room-Temperature Ionic Liquids for Applications in Actinide Chemistry ACS Symp. Ser. 2002, 818, 188-198 (Pubitemid 135703032)
32. Spange, S.; Meissner, H.; Hotzel, H.; Heublein, G. Determination of the ω-Acceptor Strength of Alcohols Z. Chem. 1984, 24, 257-258
33. Dietz, M. L.; Dzielawa, J. A.; Jensen, M. P.; Beitz, J. V.; Borkowski, M. The Road to Partition-Mechanisms of Metal Ion Transfer into Ionic Liquids and Their Implications for the Application of Ionic Liquids as Extraction Solvents ACS Symp. Ser. 2005, 902, 2-18