Aromatic extraction using mixed ionic liquids: Experiments and COSMO-RS predictions

Journal of Chemical and Engineering Data

Volumn 57, Issue 4, 2012, Pages 1026-1035

  Potdar, Shailesh ^a   Anantharaj, Ramalingam ^a   Banerjee, Tamal ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

[BMIM][BF; AROMATIC EXTRACTION; CLOUD POINT METHOD; CONDUCTOR LIKE SCREENING MODELS; COSMO-RS; DISTRIBUTION RATIO; LIQUID LIQUID EQUILIBRIUM; NMR TECHNIQUES; QUATERNARY SYSTEMS; ROOT-MEAN SQUARE DEVIATION; TIE LINE; TRIFLUOROMETHYL;

AMIDES; BENZENE; EXPERIMENTS; FORECASTING; IONIC LIQUIDS; TOLUENE;

HEXANE;

EID: 84859768472     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je200924e     Document Type: Article

References (42)

1. Weissermel, K.; Arpe, H. J. Industrial Organic Chemistry; Wiley-VCH: Weinheim, 2003.
2. Prakash, S. Petroleum Fuels Manufacturing Handbook; McGraw-Hill: New York, 2009.
3. Meindersma, G. W. Extraction of aromatics from naphtha with ionic liquids: from solvent development to pilot RDC evaluation. Ph.D. Thesis. University of Twente, The Netherlands, 2005.
4. Meindersma, G. W.; Anita, J. G.; de Haan, A. B. Selection of ionic liquids for the extraction of aromatic hydrocarbons from aromatic/aliphatic mixtures Fuel Process. Technol. 2005, 87, 59-70
5. Chen, J.; Li, Z.; Duan, L. Liquid-Liquid Equilibria of Ternary and Quaternary Systems Including Cyclohexane, 1-Heptene, Benzene, Toluene, and Sulfolane at 298.15 K J. Chem. Eng. Data 2000, 45, 689-692
6. Universal Oil Products; http://www.uop.com/aromatics/3000.html (accessed May 6, 2011).
7. Krishna, R.; Goswami, A. N.; Nanoti, S. M.; Rawat, B. S.; Khanna, M. K.; Dhobal Influence of emulsion breakage on selectivity in the separation of benzene heptane mixtures using aqueous surfactant membranes J. Indian J. Technol. 1987, 25, 602-606
8. Yorulmaz, Y.; Karuzcu, F. Sulpholane versus Diethylene glycol in Recovery of Aromatics Chem. Eng. Res. Des. 1985, 63, 184-190
9. Ali, S. H.; Lababidi, H. M. S.; Merchant, S. Q.; Fahim, M. A. Extraction of aromatics from naphtha reformate using propylene carbonate Fluid Phase Equilib. 2003, 214, 25-38
10. Rogers, R. D.; Huddelston, J. G.; Willaur, H. D. Room temperature ionic liquids as novel media for "clean" liquid-liquid extraction Chem. Commun. 1998, 8, 1765-1766
11. Arlt, W.; Seiler, M.; Jork, C.; Schneider, T. Ionic liquids as selective or azeotropic mixtures. PCT International Application, WO 2002/074718 A2. 2002.
12. Dupont, J.; Consort, C. S.; Spencer, J. J. Braz. Chem. Soc. 2005, 11, 337-344
13. Doherty, A. P.; Diaconu, L.; Marley, E.; Spedding, P. L.; Barhdadi, R.; Troupel, M. Application of clean technologies using electrochemistry in ionic liquids Asia Pac. J. Chem. Eng. 2011, 7, 14-23
14. Bi, W.; Zhu, T.; Park, D. W.; Row, K. H. Sorption of carbon dioxide by ionic liquid-based sorbents Asia Pac. J. Chem. Eng. 2010, 7, 86-92
15. Cassol, C. C.; Umpierre, A. P.; Ebeling, G.; Ferrera, B. On the Extraction of Aromatic Compounds from Hydrocarbons by Imidazolium Ionic Liquids Int. J. Mol. Sci. 2007, 8, 593-605
16. 2 at T = 298.15 K Fluid Phase Equilib. 2007, 2, 173-179
17. Arce, A.; Earle, M. J.; Katdare, S. P.; Rodríguez, H.; Seddon, K. R. Phase equilibria of mixtures of mutually immiscible ionic liquids Fluid Phase Equilib. 2007, 261, 427-433
18. Arce, A.; Earle, M. J.; Katdare, S. P.; Rodríguez, H. Application of mutually immiscible ionic liquids to the separation of aromatic and aliphatic hydrocarbons by liquid extraction: a preliminary approach Phys. Chem. Chem. Phys. 2008, 10, 2538-2542
19. Kumar, A. A. P.; Banerjee, T. Thiophene separation with ionicliquids for desulfurization: A quantum chemical approach Fluid Phase Equilib. 2009, 278, 1-8
20. Klamt, A.; Schüürmann, G. COSMO: A New Approach to Dielectric Screening in Solvents with Explicit Expressions for the Screening Energy and its Gradient J. Chem. Soc., Perkin Trans. 1993, 2, 799-805
21. Klamt, A.; Eckert, F. Fast solvent screening via quantum chemistry: COSMO-RS approach AIChE J. 2002, 48, 369-385
22. Klamt, A. Conductor Like Screening Model for Real Solvents: A new approach to the quantitative calculation of solvation phenemona J. Phys. Chem. 1995, 99, 2224-2235
23. Banerjee, T.; Verma, K. K.; Khanna, A. A. Liquid Liquid Equilibria for Ionic Liquid based systems using COSMO-RS: Effect of Cation and Anion combination AIChE J. 2008, 54, 1874-1885
24. Banerjee, T.; Sahoo, R. K.; Khanna, A. Multi-component Liquid-Liquid Equilibria Prediction for Aromatic Extraction Systems using COSMO-RS Ind. Eng. Chem. Res. 2007, 46, 1292-1304
25. Banerjee, T.; Khanna, A. Infinite Dilution Activity Coefficients for Trihexyltetradecyl Phosphonium Ionic Liquids: Measurements and COSMO-RS Prediction J. Chem. Eng. Data 2006, 51, 2170-2177
26. Freire, M. G.; Carvalho, P. J.; Gardas, R. L.; Santos, L. M. N. B. F.; Marrucho, I. M.; Coutinho, J. A. P. Solubility of Water in Tetradecyltrihexylphosphonium-Based Ionic Liquids J. Chem. Eng. Data 2008, 53, 2378-2382
27. 2N] Hydrophobic Ionic Liquids J. Phys. Chem. B 2008, 112, 1604-1610
28. Seader, J. D.; Henle, E. J. Separation Process Principles; Wiley: New York, 2005; p 165.
29. 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.; 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 C.02; Gaussian, Inc.: Pittsburgh, PA, 2003.
30. Schafteenaar, G.; Noordik, J. H. Molden: a pre- and post-processing program for molecular and electronic structures J. Comput. Aided Mol. Des. 2000, 14, 123-134
31. Fock, V. Z. Phys. 1930, 61, 126
32. Turner, E. A.; Pye, C.; Singer, R. D. Use of ab Initio Calculations toward the Rational Design of Room Temperature Ionic Liquids J. Phys. Chem. A 2003, 107, 2277-2288
33. Perdew, J. P. Implements the Perdew 1986 (P86) correlation functional Phys. Rev. B 1986, 33, 8822-8824
34. Schaefer, A.; Huber, C.; Ahlrichs, R. Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr J. Chem. Phys. 1994, 100, 5829-5835
35. Sosa, C.; Andzelm, J.; Elkin, B. C.; Wimmer, E.; Dobbs, K. D.; Dixon, D. A. A local density functional study of the structure and vibrational frequencies of molecular transition-metal compounds J. Phys. Chem. 1992, 96, 6630-6636
36. Letcher, T. M.; Deenadayalu, N. Ternary liquid-liquid equilibria for mixtures of 1-methyl-3-octyl-imidazolium chloride + benzene + an alkane at T = 298.2 K and 1 atm J. Chem. Thermodyn. 2003, 35, 67-76
37. Letcher, T. M.; Siswana, P. M. Phase equilibria for (an alkanol + p -xylene + water) at 298.2 K J. Chem. Thermodyn. 1992, 21, 203-207
38. García, J.; Fernández, A.; Torrecilla, J. S.; Oliet, M.; Rodríguez, F. Liquid-liquid equilibria for {hexane + benzene + 1-ethyl-3-methylimidazolium ethylsulfate} at (298.2, 313.2 and 328.2) K Fluid Phase Equilib. 2009, 282, 117-120
39. García, J.; Fernández, A.; Torrecilla, J. S.; Oliet, M.; Rodríguez, F. Ternary Liquid-Liquid Equilibria Measurement for Hexane and Benzene with the Ionic Liquid 1-Butyl-3-methylimidazolium Methylsulfate at T = (298.2, 313.2, and 328.2) K J. Chem. Eng. Data 2010, 55, 258-261
40. García, J.; García, S.; Torrecilla, J. S.; Rodríguez, F. Proceedings of International Conference on Chemical and Process Engineering, IChep-9, Rome, Italy, 2009; pp 480-486 (doi: 10.3303/CET0917264).
41. Labadibi, H. M. S.; Ali, H. A.; Fahim, M. A. Optimization of Aromatics Extraction of Naphtha Reformate by Propylene Carbonate/Diethylene Glycol Mixed Solvent Ind. Eng. Chem. Res. 2006, 45, 5086-5097
42. Gómez, E.; Domínguez, I.; González, B.; Domínguez, A. Liquid-Liquid Equilibria of the Ternary Systems of Alkane + Aromatic + 1-Ethylpyridinium Ethylsulfate Ionic Liquid at T = (283.15 and 298.15) K J. Chem. Eng. Data 2010, 55, 5169-5175