Liquid-liquid extraction of low-concentration aniline from aqueous solutions with salts

Industrial and Engineering Chemistry Research

Volumn 49, Issue 6, 2010, Pages 2581-2588

  Wu, Xiaohua ^a   Lei, Zhigang ^a   Li, Qunsheng ^a   Zhu, Jiqin ^a   Chen, Biaohua ^a  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE CONCENTRATION; AQUEOUS SOLUTIONS; AS EXTRACTION; COMPLEX FORMATIONS; EXTRACTION CONDITIONS; EXTRACTION EFFICIENCIES; EXTRACTION PROCESS; EXTRACTION TEMPERATURES; FOURIER TRANSFORM INFRARED; FTIR; HOFMEISTER SERIES; IMIDAZOLIUM-BASED IONIC LIQUID; INORGANIC SOLIDS; INTERACTION FORCES; LIQUID-LIQUID EXTRACTION; LIQUID-LIQUID EXTRACTION PROCESS; LOW CONCENTRATIONS; METHYL TERT BUTYL ETHER; PHASE VOLUME RATIO; SALTING EFFECT; SEPARATION MECHANISM; WATER SAMPLES;

ANILINE; COMPLEXATION; DENSITY FUNCTIONAL THEORY; ETHERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; IONIC LIQUIDS; IONIZATION OF LIQUIDS; SALTS;

SOLVENT EXTRACTION;

EID: 77949430153     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie9012979     Document Type: Article

References (54)

1. Dalene, M.; Skarping, G. Trace analysis of amines and isocyanates using glass capillary gas chromatography and selective detection. IV: Determination of free aromatic amines using nitrogen-selective detection. J. Chromatogr. 1985, 331, 321-330.
2. Laha, S.; Luthy, R. G. Oxidation of aniline and other primary aromatic amines by manganese dioxide. Environ. Sci. Technol. 1990, 24, 363-373.
3. Kataoka, H. Derivatization reactions for the determination of amines by gas chromatography and their applications in Environmental analysis. J. Chromatogr. A 1996, 733, 19-34.
4. Zhu, J.; Aikawa, B. Determination of aniline and related monoaromatic amines in indoor air in selected Canadian residences by a modified thermal desorption GC/MS method. Environ. Int. 2004, 30, 135-143.
5. Palmiotto, G.; Pieraccini, G.; Moneti, G.; Dolora, P. Determination of the levels of aromatic amines in indoor and outdoor air in Italy. Chemosphere 2001, 43, 355-361.
6. Marche, C.; Delpine, H.; Ferronato, C.; Jose, J. Apparatus for the on-line GC determination of hydrocarbon solubility in water: Benzene and cyclohexane from 70 °C to 150 °C. J. Chem. Eng. Data 2003, 48, 398-401.
7. -1 level in Environmental water by gas chromatography-mass spectrometry involving N-allyl-N?-arylthiourea formation and their on-line pyrolysis to aryl isothiocyanates. J. Chromatogr. A 2003, 1010, 243-253.
8. Weiss, T.; Angerer, J. Simultaneous determination of various aromatic amines and metabolites of aromatic nitro compounds in urine for low level exposure using gas chromatography-mass spectrometry. J. Chromatogr. B. 2002, 778, 179-192.
9. Akyüz, M. Simultaneous determination of aliphatic and aromatic amines in indoor and outdoor air samples by gas chromatography-mass spectrometry. Talanta 2007, 71, 486-492.
10. Marengo, E.; Gennaro, M. C.; Gianotti, V.; Prenesti, E. Optimization of the separation of mono- and dichloroanilines in ion interaction highperformance liquid chromatography. J. Chromatogr. A 1999, 863, 1-11.
11. Jen, J.; Chang, C.; Yang, T. C. On-line microdialysis-highperformance liquid chromatographic determination of aniline and 2-chloroaniline in polymer industrial wastewater. J. Chromatogr. A 2001, 930, 119-125.
12. Asthana, A.; Bose, D.; Durgbanshi, A.; Sanghi, S. K.; Kok, W. T. Determination of aromatic amines in water samples by capillary electrophoresis with electrochemical and fluorescence detection. J. Chromatogr. A 2000, 895, 197-203.
13. Rama, J.; Ganesh, J.; Malayappan, B.; Raghavan, C.; Ganga, R. Analysis of arylamine isomers by micellar electrokinetic chromatography. Electrophoresis 2002, 23, 584-590.
14. Chen, S.; Xu, Y.; Bi, Y.; Du, W.; Liu, B. Analysis of Environmental pollutants metabolized from pesticides using capillary electrophoresis with multiphoton-excited fluorescence detection. Talanta 2006, 70, 63-137
15. Fernandes, J. O.; Ferreira, M. A. Combined ion-pair extraction and gas chromatography-mass spectrometry for the simultaneous determination of diamines, polyamines and aromatic amines in Port wine and grape juice. J. Chromatogr. A 2000, 886, 183-195.
16. 2O system. Anal. Chim. Acta 2006, 557, 329-336.
17. He, C.; Li, S.; Liu, H.; Li, K.; Liu, F. Extraction of testosterone and epitestosterone in human urine using aqueous two-phase systems of ionic liquid and salt. J. Chromatogr. A 2005, 1082, 143-149.
18. Patsias, J.; Papadopoulou-Mourkidou, E. Development of an automated on-line solid-phase extraction-high-performance liquid chromatographic method for the analysis of aniline, phenol, caffeine and various selected substituted aniline and phenol compounds in aqueous matrices. J. Chromatogr. A 2000, 904, 171-188.
19. Muller, L.; Fattore, E.; Benfenati, E. Determination of aromatic amines by solid-phase microextraction and gas chromatography-mass spectrometry in water samples. J. Chromatogr. A 1997, 791, 221-230.
20. Huddleston, J. G.; Willauer, H. D.; Giffin, S. T.; Rogers, R. D. Aqueous polymeric solutions as Environmentally benign liquid-liquid extraction media. Ind. Eng. Chem. Res. 1999, 38, 2523-2539.
21. Bohme, A.; Paschke, A.; Vrbka, P.; Dohnal, V.; Schuurmann, G. Determination of Temperature-Dependent Henry's Law Constant of Four Oxygenated Solutes in Water Using Headspace Solid-Phase Microextraction Technique. J. Chem. Eng. Data 2008, 53, 2873-2877.
22. He, Y.; Lee, H. K. Liquid-phase microextraction in a single drop of organic solvent by using a conventional microsyringe. Anal. Chem. 1997, 69, 4634-4640.
23. Berijani, S.; Assadi, Y.; Anbia, M.; Milani Hosseini, M. R.; Aghaee, E. Dispersive liquid-liquid microextraction combined with gas chromatography- flame photometric detection. J. Chromatogr. A 2006, 1123, 1-9.
24. Fattahi, N.; Assadi, Y.; Milani Hosseini, M. R.; Jahromi, E. Z. Determination of chlorophenols in water samples using simultaneous dispersive liquid-liquid microextraction and derivatization followed by gas chromatography-electron-capture detection. J. Chromatogr. A 2007, 1157, 23-29.
25. Rezaee, M.; Assadi, Y.; Milani Hosseini, M. R.; Aghaee, E.; Ahmadi, F.; Berijani, S. Determination of organic compounds in water using dispersive liquid-liquid microextraction. J. Chromatogr. A 2006, 1116, 1-9.
26. Kozani, R. R.; Assadi, Y.; Shemirani, F.; Milani Hosseini, M. R.; Jamali, M. R. Determination of trihalomethanes in drinking water by dispersive liquid-liquid microextraction then gas chromatography with electron-capture detection. Chromatographia 2007, 66, 81-86.
27. Feng, X. D.; Lin, Y.; Qu, F. P. Treatment of dilute solution anilinescontaining with displacement by extraction. Chin. J. Environ. Sci. 2001, 22, 71-74.
28. Ma, X. L.; Wu, M. X. Treatment of aniline wastewater with complexation extraction. Jiangsu Chem. Ind. 2001, 1, 42-44.
29. Lei, Z. G.; Chen, B. H.; Li, C. Y. COSMO-RS modeling on the extraction of stimulant drugs from urine sample by the double actions of supercritical carbon dioxide and ionic liquid. Chem. Eng. Sci. 2007, 62, 3940-3950.
30. -. Chin. J. Environ. Eng. 2009, 8, 1399-1404.
31. Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Room temperature ionic liquid as novel media for "clean" liquid-liquid extraction. Chem. Commun. 1998, 16, 1765-1766.
32. Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley- VCH: Weinheim, Germany, 2003.
33. Seiler, M.; Jork, C.; Karvarnou, A.; Arlt, W.; Hirsch, R. Separation of Azeotropic Mixtures Using Hyperbranched Polymers or Ionic Liquids. AIChE J. 2004, 50, 2439-2454.
34. Lei, Z. G.; Chen, B. H.; Li, C. Y.; Liu, H. Predictive Molecular Thermodynamic Models for Liquids, Solid Salts, Polymers, and Ionic Liquids. Chem. Rev. 2008, 108, 1419-1455.
35. Atkins, P. W.; Julio, D. P. Physical Chemistry, 8th ed.; W. H. Freeman and Company: Oxford, 2006.
36. Lei, Z. G.; Li, C. Y.; Chen, B. H. Extractive distillation: A review. Sep. Purif. Rev. 2003, 32, 121-213.
37. Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071-2084.
38. Wasserscheid, P.; Keim, W. Ionic liquids-New "solutions" for transition metal catalysis. Angew. Chem., Int. Ed. 2000, 39, 3773-3789.
39. Lei, Z. G.; Zhang, J. G.; Li, Q. S.; Chen, B. H. UNIFAC Model for Ionic Liquids. Ind. Eng. Chem. Res. 2009, 48, 2697-2704.
40. Lee, J. S.; Wang, X. Q.; Luo, H. M.; Baker, G. A.; Dai, S. Facile ionothermal synthesis of microporous and mesoporous carbons from task specific ionic liquids. J. Am. Chem. Soc. 2009, 131, 4596-4597.
41. Zhang, J.; Huang, C. P.; Chen, B. H.; Ren, P. J.; Lei, Z. G. Extraction of aromatic hydrocarbons from aromatic/aliphatic mixtures using chloroaluminate room-temperature ionic liquids as extractants. Energy Fuels 2007, 21, 1724-1730.
42. Lei, Z. G.; Arlt, W.; Wasserscheid, P. Separation of 1-hexene and n-hexane with ionic liquids. Fluid Phase Equilib. 2006, 241, 290-299.
43. Smirnova, S. V.; Torocheshnikova, I. I.; Formanovsky, A. A.; Pletnev, I. V. Solvent extraction of amino acids into a room temperature ionic liquid with dicyclohexano-18-crown-6. Anal. Bioanal. Chem. 2004, 378, 1369-1375.
44. 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.
45. Vidal, S. T. M.; Correia, M. J. N.; Marques, M. M.; Ismael, M. R.; Reis, M. T. Studies on the use of ionic liquids as potential extractants of phenolic compounds and metal ions. Sep. Sci. Technol. 2004, 39, 2155-2169.
46. Matsumoto, M.; Mochiduki, K. J.; Fukunishi, K.; Kondo, K. Extraction of organic acids using imidazolium-based ionic liquids and their toxicity to Lactobacillus rhamnosus. Sep. Purif. Technol. 2004, 40, 97-101.
47. Zhao, C.; Burrell, G.; Torriero, A. A. J.; Separovic, F.; Dunlop, N. F.; MacFarlane, D. R.; Bond, A. M. Electrochemistry of room temperature protic ionic liquids. J. Phys. Chem. B. 2008, 112, 6923-6936.
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
49. Hofmeister, F. Zur Lehre von der Wirkung dder Salze (About the science of the effct of salts). Arch. Exp. Pathol. Pharmakol. 1888, 24, 247-260.
50. Zhang, Y.; Cremer, P. S. Interactions between macromolecules and ions: The Hofmeister series. Curr. Opin. Chem. Biol. 2006, 10, 658-663.
51. Collins, K. D. Ions from the Hofmeister series and osmolytes: Effects on proteins in solution and in the crystallization process. Methods 2004, 34, 300-311.
52. Pegram, L. M.; Record, M. T. Partitioning of atmospherically relevant ions between bulk water and the water/vapor interface. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 14278-14281.
53. Pegram, L. M.; Record, M. T. Hofmeister salt effects on surface tension arise from partitioning of anions and cations between bulk water and the air-water interface. J. Phys. Chem. B 2007, 111, 5411-5417.
54. Pegram, L. M.; Record, M. T. Thermodynamic Origin of Hofmeister Ion Effects. J. Phys. Chem. B 2008, 112, 9428-9436.