Estudio del equilibrio líquido-líquido de tolueno + heptano con el líquido iónico 1,3-dimetilimidazolio metilsulfato a 318.15 K
Palabras clave:
Liquid-liquid equilibrium, ionic liquids, [MMim] [MeSO4], extraction, tolueneResumen
The extraction of toluene from heptane was analyzedby liquid extraction with 1,3-dimethylimidazolium methylsulfate[MMim][MeSO4] ionic liquid, as a solvent.The experimental (liquid + liquid) equilibrium (LLE)data were determined at T= 318.15 K and atmosphericpressure. Selectivity and distribution coefficient,derived from the tie-lines, were used to determine theability of this ionic liquid as solvent for the separationof toluene from its mixtures with heptane. Thedegree of consistency of the experimental LLE datawas ascertained using the Othmer–Tobias equation.The experimental data for LLE of the ternary systemwere correlated with the Non-Random Two-Liquid(NRTL) and UNIversal QUAsi-Chemical (UNIQUAC)thermodynamic models.
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Referencias
1. Arce, A., Earle, M.J., Rodríguez, H., Seddon, K.R.,Soto, A. (2008). 1-Ethyl-3-methylimidazoliumbis{(trifluoromethyl)sulfonyl} amide as solventfor the separation of aromatic and aliphatic hydrocarbonsby extraction – extension to C7- andC8-fractions, Green Chem., 10, 1294–1300.
2. Yorulmaz, Y., Karpuzcu, F. (1985). Sulpholaneversus diethylene glycol in recovery of aromatics.Chem. Eng. Res. Des., 63, 184–190.
3. Krishna, R., Goswami, A.N., Nanoti, S.M.,Rawat, B.S., Khana, M.K., Dobhal, J. (1987).Extraction of aromatics from 63-69 °C naphthafraction for food grade hexane productionusing sulfolane and NMP as solvents, Ind. J.Technol., 25, 602–606.
4. Wang, W., Gou, Z.M., Zhu, S.L. (1998). Liquid-liquid equilibria for aromatics extractionsystems with tetraethylene glycol, J. Chem. Eng.Data, 43, 81–83.
5. Chen, J., Duan, L-P., Mi, J-G., Feio, W-Y., Li,Z-C. (2000). Liquid-liquid equilibria of multicomponentsystems including n-hexane, n-octane,benzene, toluene, xylene and sulfolane at298.15 K and atmospheric pressure, Fluid PhaseEquilib., 173, 109–119.
6. Choi, Y.J., Cho, K.W., Cho, B.W., Yeo, Y-K.(2002). Optimization of the sulfolane extractionplant based on modeling and simulation,Ind. Eng. Chem. Res., 41, 5504–5509.
7. Selvan, M.S., McKinley, M.D., Dubois, R.H.,Atwood, J.L. (2000). Liquid-liquid equilibria fortoluene + heptane + 1-ethyl-3-methylimidazoliumtriiodide and toluene + heptane + 1-butyl-3-methylimidazolium triiodide, J. Chem. Eng.Data, 45, 841–845.
8. Letcher, T.M., Deenadayalu, N. (2003). Ternaryliquid-liquid equilibria for mixture of 1-methyl-3-octyl-imidazolium chloride+benzene+an alkaneat 298.2 K and 1 atm, J. Chem. Thermodyn.,35(1), 67–76.
9. Letcher, T.M., Reddy, P. (2005). Ternary(liquid+liquid) equilibria for mixtures of1-hexyl-3-methylimidaolium (tetrafluoroborateor hexafluoroborate)+benzene+an alkane at298.2 K and p=0.1 MPa. J. Chem. Thermodyn.,37, 415–421.
10. Meindersma, G.W., Podt, A.J.G., de Haan, A.B.(2006). Ternary liquid-liquid equilibria for mixturesof toluene + n-heptane + an ionic liquid,Fluid Phase Equilib., 247, 158–168.
11. Deenadayalu, N., Ngcongo, K.C., Letcher,T.M., Ramjugernath, D. J. (2006). Liquid-liquidequilibria for ternary mixtures (an ionicliquid + benzene + hexane + hexadecane) atT=298.2 K and atmospheric pressure, J. Chem.Eng. Data, 51, 988–991.
12. Domanska, U., Pobudkowska, A., Królikowski,M. (2007). Separation of aromatic hydrocarbonsfrom alkanes using ammonium ionicliquid C2NTf2N at T=298.15 K, Fluid PhaseEquilib., 259, 173–179.
13. Abu-Eishah, S.I., Dowaidar, A.M. (2008). Liquid-liquid equilibrium of ternary systems ofcyclohexane + (benzene, + toluene, + ethylbenzene,or + o-xylene) + 4-methy-N-butylpyridinium tetrafluoroborate ionic liquid at303.15 K, J. Chem. Eng. Data, 53, 1708–1712.
14. Wang, R., Wang, J., Meng, H., Li, C., Wang, Z.(2008). Liquid-liquid equilibria for benzene +cyclohexane + 1-methyl-3-methylimidazoliumdimethylphosphate or + 1-ethyl-3-methylimidazoliumdiethylphosphate, J. Chem. Eng. Data,53, 1159–1162.
15. Maduro, R.M., Aznar, M. (2008). Liquid-liquidequilibrium of ternary systems 1-butyl-3-methylimidazoliumhexafluorophosphate + aromatic+ aliphatic, Fluid Phase Equilib., 265, 129–138.
16. Garcia, J., Fernández, A., Torrecilla, J.S., Oliet,M., Rodríguez, F. (2009). Liquid-liquid equilibriafor {hexane+benzene+1-ethyl-3-methylimidazoliumethylsulfate} at (298.2, 313.2 and328.2) K, Fluid Phase Equilib., 282, 117–120.
17. González, E.J., Calvar, N., González, B., Domínguez,Á. (2010). Liquid extraction of benzenefrom its mixtures using 1-ethyl-3-methylimidazoliumethylsulfate as a Solvent. J. Chem.Eng. Data, 55, 4931–4936.
18. González, E.J., Calvar, N., Gómez, E., Domínguez,Á. (2010). Separation of benzene from linearalkanes (C6-C9) using 1-ethyl-3-methylimiAVANCESInvestigación en Ingeniería Vol. 9 - No. 2 (2012) 35dazolium ethylsulfate at T=298.15 K, J. Chem.Eng. Data, 55, 3422–3427.
19. González, E.J., Calvar, N., Gómez, E., Domínguez,Á. (2011). Application of [EMIm][ESO4]ionic liquid as solvent in the extraction of toluenefrom cycloalkanes: Study of liquid-liquidequilibria at T=298.15 K, Fluid Phase Equilib.,303, 174–179.
20. Gonzáles, E.J., González, B., Calvar, N., Domínguez,Á. (2011). Study of [EMIm][ESO4]ionic liquid as solvent in the liquid-liquid extractionof xylenes from their mixtures withhexane, Fluid Phase Equilib., 305, 227–232.
21. González, E.J., Calvar, N., Domínguez, I.,Domínguez, Á. (2011). Extraction of toluenefrom aliphatic compounds using an ionic liquidas solvent: influence of the alkane on the(liquid+liquid) equilibrium, J. Chem. Thermodyn.,43, 562–568.
22. García, S., Larriba, M., García, J., Torrecilla, J.S.,Rodríguez, F. (2012). Alkylsulfate-based ionic liquidsin the liquid-liquid extraction of aromatichydrocarbons, J. Chem. Thermodyn., 45, 68–74.
23. Seoane, R.G., Gómez, E., González, E.J., Domínguez,Á. (2012). (Liquid+liquid) equilibria for theternary mixtures (alkane+toluene+ionic liquid) atT= 298.15 K: Influence of the anion on the phaseequilibria. J. Chem. Thermodyn., 47, 402–407.
24. Corderi, S., Calvar, N., Gómez, E., Domínguez,Á. (2012). Capacity of ionic liquids [EMim][NTf2] and [EMpy][NTf2] for extraction of toluenefrom mixtures with alkanes: Comparativestudy of the effect of the cation, Fluid PhaseEquilib., 315, 46–52.
25. Pereiro, A.B., Deive, F.J., Esperança, J.M.S.S.,Rodríguez, A. (2010). Alkylsulfate-based ionicliquids to separate azeotropic mixtures, FluidPhase Equilib., 291, 13–17.
26. Meinsderma, G.W., de Haan, A.B. (2008). Conceptualprocess design for aromatic/aliphaticseparation with ionic liquids, Chem. Eng. Res.Des., 86, 745–752.
27. Martínez-Reina, M., Amado-González, E.,Muñoz-Muñoz, Y.M., (2012). Study of liquidliquidequilibrium of benzene + (hexane, heptaneand cyclohexane) with the ionic liquid1-ethyl-3-methylimidazolium ethylsulfate at308.15 K, Rev. Colomb. Quím., 41(1), 89–107.
28. Othmer, D.F., Tobias, P.E. (1942). Tie Line Correlation,Ind. Eng. Chem., 34(6), 693–696.
29. Renon, H., Prausnitz, J.M. (1968). Local Compositionin Thermodynamics Excess Functionfor Liquid Mixtures, AIChE J., 14, 135–144.
30. Abrams, D.S., Prausnitz, J.M. (1975). Statisticalthermodynamics of liquid mixtures: a new expressionfor the excess Gibbs energy of partly orcompletely substances, AIChE J., 21, 116–128.
31. Pereiro, A.B., Rodríguez, A. (2007). Ternary(liquid+liquid) equilibria of the azeotrope (ethylacetate + 2-propanol) with different ionicliquids at T=298.15 K, J. Chem. Thermodyn., 39,1608–1613.
32. Calvar, N., Gómez, E., González, B., Domínguez,Á. (2009). Experimental densities, refractive indices,and speeds of sound of 12 binary mixturescontaining alkanes and aromatic compound atT= 313.15 K, J. Chem. Thermodyn., 41, 939–944.
33. Morávková, L., Linek, J. (2008). Excess molarvolumes of (octane + benzene, or toluene, or1,3-xylene, or 1,3,5-trimethylbenzene) at temperaturesbetween (298.15 and 328.15) K, J.Chem. Thermodyn., 40, 671–676.
34. Alonso, L., Arce, A., Francisco, M., Soto, A.(2008). (Liquid+Liquid) equilibria of [C8mim][NTf2] ionic liquid with sulfur-component andhydrocarbons, J. Chem. Thermodyn., 40, 265–270.
35. Santiago, R.S., Santos, G.R., Aznar, M. (2009).UNIQUAC correlation of liquid-liquid equilibriumin systems involving ionic liquids: The DFTPCMapproach, Fluid Phase Equilib., 278, 54–61.
36. Santiago, R.S., Santos, G.R., Aznar, M. (2010).UNIQUAC correlation of liquid-liquid equilibriumin systems involving ionic liquids:The DFT-PCM approach. Part II, Fluid PhaseEquilib., 293, 66–72.
37. Nelder, J.A., Mead, R. (1965). A Simplex Methodfor Function Minimization, Comput. J., 7, 308–313.
38. Sørensen, J.M., Magnussen, T., Rasmussen, P.,Fredenslud, A. (1979). Liquid-Liquid Equilibriumdata: Their retrieval, correlation and predictionpart II: Correlation, Fluid Phase Equilib.3, 47–82.
2. Yorulmaz, Y., Karpuzcu, F. (1985). Sulpholaneversus diethylene glycol in recovery of aromatics.Chem. Eng. Res. Des., 63, 184–190.
3. Krishna, R., Goswami, A.N., Nanoti, S.M.,Rawat, B.S., Khana, M.K., Dobhal, J. (1987).Extraction of aromatics from 63-69 °C naphthafraction for food grade hexane productionusing sulfolane and NMP as solvents, Ind. J.Technol., 25, 602–606.
4. Wang, W., Gou, Z.M., Zhu, S.L. (1998). Liquid-liquid equilibria for aromatics extractionsystems with tetraethylene glycol, J. Chem. Eng.Data, 43, 81–83.
5. Chen, J., Duan, L-P., Mi, J-G., Feio, W-Y., Li,Z-C. (2000). Liquid-liquid equilibria of multicomponentsystems including n-hexane, n-octane,benzene, toluene, xylene and sulfolane at298.15 K and atmospheric pressure, Fluid PhaseEquilib., 173, 109–119.
6. Choi, Y.J., Cho, K.W., Cho, B.W., Yeo, Y-K.(2002). Optimization of the sulfolane extractionplant based on modeling and simulation,Ind. Eng. Chem. Res., 41, 5504–5509.
7. Selvan, M.S., McKinley, M.D., Dubois, R.H.,Atwood, J.L. (2000). Liquid-liquid equilibria fortoluene + heptane + 1-ethyl-3-methylimidazoliumtriiodide and toluene + heptane + 1-butyl-3-methylimidazolium triiodide, J. Chem. Eng.Data, 45, 841–845.
8. Letcher, T.M., Deenadayalu, N. (2003). Ternaryliquid-liquid equilibria for mixture of 1-methyl-3-octyl-imidazolium chloride+benzene+an alkaneat 298.2 K and 1 atm, J. Chem. Thermodyn.,35(1), 67–76.
9. Letcher, T.M., Reddy, P. (2005). Ternary(liquid+liquid) equilibria for mixtures of1-hexyl-3-methylimidaolium (tetrafluoroborateor hexafluoroborate)+benzene+an alkane at298.2 K and p=0.1 MPa. J. Chem. Thermodyn.,37, 415–421.
10. Meindersma, G.W., Podt, A.J.G., de Haan, A.B.(2006). Ternary liquid-liquid equilibria for mixturesof toluene + n-heptane + an ionic liquid,Fluid Phase Equilib., 247, 158–168.
11. Deenadayalu, N., Ngcongo, K.C., Letcher,T.M., Ramjugernath, D. J. (2006). Liquid-liquidequilibria for ternary mixtures (an ionicliquid + benzene + hexane + hexadecane) atT=298.2 K and atmospheric pressure, J. Chem.Eng. Data, 51, 988–991.
12. Domanska, U., Pobudkowska, A., Królikowski,M. (2007). Separation of aromatic hydrocarbonsfrom alkanes using ammonium ionicliquid C2NTf2N at T=298.15 K, Fluid PhaseEquilib., 259, 173–179.
13. Abu-Eishah, S.I., Dowaidar, A.M. (2008). Liquid-liquid equilibrium of ternary systems ofcyclohexane + (benzene, + toluene, + ethylbenzene,or + o-xylene) + 4-methy-N-butylpyridinium tetrafluoroborate ionic liquid at303.15 K, J. Chem. Eng. Data, 53, 1708–1712.
14. Wang, R., Wang, J., Meng, H., Li, C., Wang, Z.(2008). Liquid-liquid equilibria for benzene +cyclohexane + 1-methyl-3-methylimidazoliumdimethylphosphate or + 1-ethyl-3-methylimidazoliumdiethylphosphate, J. Chem. Eng. Data,53, 1159–1162.
15. Maduro, R.M., Aznar, M. (2008). Liquid-liquidequilibrium of ternary systems 1-butyl-3-methylimidazoliumhexafluorophosphate + aromatic+ aliphatic, Fluid Phase Equilib., 265, 129–138.
16. Garcia, J., Fernández, A., Torrecilla, J.S., Oliet,M., Rodríguez, F. (2009). Liquid-liquid equilibriafor {hexane+benzene+1-ethyl-3-methylimidazoliumethylsulfate} at (298.2, 313.2 and328.2) K, Fluid Phase Equilib., 282, 117–120.
17. González, E.J., Calvar, N., González, B., Domínguez,Á. (2010). Liquid extraction of benzenefrom its mixtures using 1-ethyl-3-methylimidazoliumethylsulfate as a Solvent. J. Chem.Eng. Data, 55, 4931–4936.
18. González, E.J., Calvar, N., Gómez, E., Domínguez,Á. (2010). Separation of benzene from linearalkanes (C6-C9) using 1-ethyl-3-methylimiAVANCESInvestigación en Ingeniería Vol. 9 - No. 2 (2012) 35dazolium ethylsulfate at T=298.15 K, J. Chem.Eng. Data, 55, 3422–3427.
19. González, E.J., Calvar, N., Gómez, E., Domínguez,Á. (2011). Application of [EMIm][ESO4]ionic liquid as solvent in the extraction of toluenefrom cycloalkanes: Study of liquid-liquidequilibria at T=298.15 K, Fluid Phase Equilib.,303, 174–179.
20. Gonzáles, E.J., González, B., Calvar, N., Domínguez,Á. (2011). Study of [EMIm][ESO4]ionic liquid as solvent in the liquid-liquid extractionof xylenes from their mixtures withhexane, Fluid Phase Equilib., 305, 227–232.
21. González, E.J., Calvar, N., Domínguez, I.,Domínguez, Á. (2011). Extraction of toluenefrom aliphatic compounds using an ionic liquidas solvent: influence of the alkane on the(liquid+liquid) equilibrium, J. Chem. Thermodyn.,43, 562–568.
22. García, S., Larriba, M., García, J., Torrecilla, J.S.,Rodríguez, F. (2012). Alkylsulfate-based ionic liquidsin the liquid-liquid extraction of aromatichydrocarbons, J. Chem. Thermodyn., 45, 68–74.
23. Seoane, R.G., Gómez, E., González, E.J., Domínguez,Á. (2012). (Liquid+liquid) equilibria for theternary mixtures (alkane+toluene+ionic liquid) atT= 298.15 K: Influence of the anion on the phaseequilibria. J. Chem. Thermodyn., 47, 402–407.
24. Corderi, S., Calvar, N., Gómez, E., Domínguez,Á. (2012). Capacity of ionic liquids [EMim][NTf2] and [EMpy][NTf2] for extraction of toluenefrom mixtures with alkanes: Comparativestudy of the effect of the cation, Fluid PhaseEquilib., 315, 46–52.
25. Pereiro, A.B., Deive, F.J., Esperança, J.M.S.S.,Rodríguez, A. (2010). Alkylsulfate-based ionicliquids to separate azeotropic mixtures, FluidPhase Equilib., 291, 13–17.
26. Meinsderma, G.W., de Haan, A.B. (2008). Conceptualprocess design for aromatic/aliphaticseparation with ionic liquids, Chem. Eng. Res.Des., 86, 745–752.
27. Martínez-Reina, M., Amado-González, E.,Muñoz-Muñoz, Y.M., (2012). Study of liquidliquidequilibrium of benzene + (hexane, heptaneand cyclohexane) with the ionic liquid1-ethyl-3-methylimidazolium ethylsulfate at308.15 K, Rev. Colomb. Quím., 41(1), 89–107.
28. Othmer, D.F., Tobias, P.E. (1942). Tie Line Correlation,Ind. Eng. Chem., 34(6), 693–696.
29. Renon, H., Prausnitz, J.M. (1968). Local Compositionin Thermodynamics Excess Functionfor Liquid Mixtures, AIChE J., 14, 135–144.
30. Abrams, D.S., Prausnitz, J.M. (1975). Statisticalthermodynamics of liquid mixtures: a new expressionfor the excess Gibbs energy of partly orcompletely substances, AIChE J., 21, 116–128.
31. Pereiro, A.B., Rodríguez, A. (2007). Ternary(liquid+liquid) equilibria of the azeotrope (ethylacetate + 2-propanol) with different ionicliquids at T=298.15 K, J. Chem. Thermodyn., 39,1608–1613.
32. Calvar, N., Gómez, E., González, B., Domínguez,Á. (2009). Experimental densities, refractive indices,and speeds of sound of 12 binary mixturescontaining alkanes and aromatic compound atT= 313.15 K, J. Chem. Thermodyn., 41, 939–944.
33. Morávková, L., Linek, J. (2008). Excess molarvolumes of (octane + benzene, or toluene, or1,3-xylene, or 1,3,5-trimethylbenzene) at temperaturesbetween (298.15 and 328.15) K, J.Chem. Thermodyn., 40, 671–676.
34. Alonso, L., Arce, A., Francisco, M., Soto, A.(2008). (Liquid+Liquid) equilibria of [C8mim][NTf2] ionic liquid with sulfur-component andhydrocarbons, J. Chem. Thermodyn., 40, 265–270.
35. Santiago, R.S., Santos, G.R., Aznar, M. (2009).UNIQUAC correlation of liquid-liquid equilibriumin systems involving ionic liquids: The DFTPCMapproach, Fluid Phase Equilib., 278, 54–61.
36. Santiago, R.S., Santos, G.R., Aznar, M. (2010).UNIQUAC correlation of liquid-liquid equilibriumin systems involving ionic liquids:The DFT-PCM approach. Part II, Fluid PhaseEquilib., 293, 66–72.
37. Nelder, J.A., Mead, R. (1965). A Simplex Methodfor Function Minimization, Comput. J., 7, 308–313.
38. Sørensen, J.M., Magnussen, T., Rasmussen, P.,Fredenslud, A. (1979). Liquid-Liquid Equilibriumdata: Their retrieval, correlation and predictionpart II: Correlation, Fluid Phase Equilib.3, 47–82.
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2011-12-01
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Estudio del equilibrio líquido-líquido de tolueno + heptano con el líquido iónico 1,3-dimetilimidazolio metilsulfato a 318.15 K. (2011). Avances Investigación En Ingeniería, 9(2), 26-35. https://revistas.unilibre.edu.co/index.php/avances/article/view/2714
