Ionic liquids as entrainer in extractive distillation for effectively separating 1-propanol–water azeotropic mixture

doi:10.1016/j.cjche.2021.12.007

Abstract

Abstract: Economically separating 1-propanol (NPA) from water is an emergent issue for producing pharmaceutical intermediates such as n-propyl acetate, n-propylamine and so on. In this work, fourionic liquids (ILs) 1-ethyl-3-methylimidazolium thiocyanate ([EMIM][SCN]), 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF₄]), 1,3-dimethylimidazolium methylsulfate ([MMIM][MS]), 1,3-dimethylimidazolium dimethylphosphate ([MMIM][DMP]) were introduced as potential entrainers for separating NPA–water azeotropic mixture. The results show that [MMIM][MS] is the most suitable entrainer compared with other ILs from the analysis of vapor–liquid equilibrium and relative volatilities. The extractive distillation process with the entrainer regeneration system of flash tank and stripper was employed and optimized by the two-step optimization method. The results show that total annual cost and energy consumption per product flow rate were reduced by 39.79% and 60.47% compared with literature. In addition, the efficiency indicator of extractive section, efficiency indicator of per tray in extractive section, carbon dioxide emissions were also selected as the evaluation index for selection of operating parameters and calculated for different cases. The CO₂ emissions of the optimal design can be reduced by 60.98% from environmental aspect.

Key words: Ionic liquids (ILs), Extractive distillation (ED), Process optimization, Energy saving, Evaluation indicator, Optimal design

摘要： Economically separating 1-propanol (NPA) from water is an emergent issue for producing pharmaceutical intermediates such as n-propyl acetate, n-propylamine and so on. In this work, fourionic liquids (ILs) 1-ethyl-3-methylimidazolium thiocyanate ([EMIM][SCN]), 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF₄]), 1,3-dimethylimidazolium methylsulfate ([MMIM][MS]), 1,3-dimethylimidazolium dimethylphosphate ([MMIM][DMP]) were introduced as potential entrainers for separating NPA–water azeotropic mixture. The results show that [MMIM][MS] is the most suitable entrainer compared with other ILs from the analysis of vapor–liquid equilibrium and relative volatilities. The extractive distillation process with the entrainer regeneration system of flash tank and stripper was employed and optimized by the two-step optimization method. The results show that total annual cost and energy consumption per product flow rate were reduced by 39.79% and 60.47% compared with literature. In addition, the efficiency indicator of extractive section, efficiency indicator of per tray in extractive section, carbon dioxide emissions were also selected as the evaluation index for selection of operating parameters and calculated for different cases. The CO₂ emissions of the optimal design can be reduced by 60.98% from environmental aspect.

关键词: Ionic liquids (ILs), Extractive distillation (ED), Process optimization, Energy saving, Evaluation indicator, Optimal design

Xinqiang You, Kai Zhao, Ling Li, Ting Qiu. Ionic liquids as entrainer in extractive distillation for effectively separating 1-propanol–water azeotropic mixture[J]. Chinese Journal of Chemical Engineering, 2022, 49(9): 224-233.

Xinqiang You, Kai Zhao, Ling Li, Ting Qiu. Ionic liquids as entrainer in extractive distillation for effectively separating 1-propanol–water azeotropic mixture[J]. 中国化学工程学报, 2022, 49(9): 224-233.

References

[1] A.B. Pereiro, J.M.M. Araújo, J.M.S.S. Esperança, I.M. Marrucho, L.P.N. Rebelo, Ionic liquids in separations of azeotropic systems-A review, J. Chem. Thermodyn. 46 (2012) 2-28
[2] E.W. Flick, Industrial Solvents Handbook, Noyes Data Corporation, New Jersey, 1998
[3] V. Gerbaud, I. Rodriguez-Donis, L. Hegely, P. Lang, F. Denes, X.Q. You, Review of extractive distillation. Process design, operation, optimization and control, Chem. Eng. Res. Des. 141 (2019) 229-271
[4] L.S. Lee, H.C. Shen, Azeotropic behavior of a water + n-propanol + cyclohexane mixture using cyclohexane as an entrainer for separating the water + n-proponal mixture at 760 mmHg, Ind. Eng. Chem. Res. 42 (23) (2003) 5905-5914
[5] S. Çehreli, D. Özmen, U. Dramur, (Liquid + liquid) equilibria of (water + 1-propanol + solvent) at T=298.2 K, Fluid Phase Equilibria 239 (2) (2006) 156-160
[6] S. Ghizellaoui, C. Coquelet, D. Richon, A.H. Meniai, Liquid-liquid equilibrium of (water + 1-propanol + 1-pentanol) system at 298.15 and 323.15 K, Fluid Phase Equilibria 296 (1) (2010) 42-45
[7] J. Pla-Franco, E. Lladosa, S. Loras, J.B. Montón, Isobaric vapor-liquid-liquid equilibria for the ternary systems ethanol + water + propyl acetate and 1-propanol + water + propyl acetate, J. Chem. Eng. Data 59 (6) (2014) 2054-2064
[8] J. Pla-Franco, E. Lladosa, S. Loras, J.B. Montón, Proposal of isobutyl alcohol as entrainer to separate mixtures formed by ethanol and water and 1-propanol and water, J. Chem. Eng. Data 62 (9) (2017) 2697-2707
[9] V.K.P. Janakey Devi, P.S.T. Sai, A.R. Balakrishnan, Heterogeneous azeotropic distillation for the separation of n-propanol + water mixture using n-propyl acetate as entrainer, Fluid Phase Equilibria 447 (2017) 1-11
[10] J. Pla-Franco, E. Lladosa, S. Loras, J.B. Montón, Azeotropic distillation for 1-propanol dehydration with diisopropyl ether as entrainer:Equilibrium data and process simulation, Sep. Purif. Technol. 212 (2019) 692-698
[11] Z.G. Lei, C.Y. Li, B.H. Chen, Extractive distillation:A review, Sep. Purif. Rev. 32 (2) (2003) 121-213
[12] M.T.G. Jongmans, E. Hermens, M. Raijmakers, J.I.W. Maassen, B. Schuur, A.B. de Haan, Conceptual process design of extractive distillation processes for ethylbenzene/styrene separation, Chem. Eng. Res. Des. 90 (12) (2012) 2086-2100
[13] Y. An, W.S. Li, Y. Li, S.Y. Huang, J. Ma, C.L. Shen, C.J. Xu, Design/optimization of energy-saving extractive distillation process by combining preconcentration column and extractive distillation column, Chem. Eng. Sci. 135 (2015) 166-178
[14] J. Pla-Franco, E. Lladosa, J.B. Montón, S. Loras, Evaluation of the 2-methoxyethanol as entrainer in ethanol-water and 1-propanol-water mixtures, J. Chem. Eng. Data 58 (12) (2013) 3504-3512
[15] J. Pla-Franco, E. Lladosa, S. Loras, J.B. Montón, Approach to the 1-propanol dehydration using an extractive distillation process with ethylene glycol, Chem. Eng. Process.:Process. Intensif. 91 (2015) 121-129
[16] K. Ghandi, A review of ionic liquids, their limits and applications, Green Sustain.Chem. 4 (1) (2014) 44-53
[17] Z.G. Lei, C.N. Dai, J.Q. Zhu, B.H. Chen, Extractive distillation with ionic liquids:A review, AIChE J. 60 (9) (2014) 3312-3329
[18] A.V. Orchillés, P.J. Miguel, E. Vercher, A. Martínez-Andreu, Isobaric vapor-liquid equilibria for 1-propanol + water + 1-ethyl-3-methylimidazolium trifluoromethanesulfonate at 100 kPa, J. Chem. Eng. Data 53 (10) (2008) 2426-2431
[19] J.F. Wang, D.G. Wang, Z.B. Li, F. Zhang, Vapor pressure measurement and correlation or prediction for water, 1-propanol, 2-propanol, and their binary mixtures with[MMIM] [DMP] ionic liquid, J. Chem. Eng. Data 55 (11) (2010) 4872-4877
[20] A.V. Orchillés, P.J. Miguel, V. González-Alfaro, E. Vercher, A. Martínez-Andreu, Isobaric vapor-liquid equilibria of 1-propanol + water + trifluoromethanesulfonate-based ionic liquid ternary systems at 100 kPa, J. Chem. Eng. Data 56 (12) (2011) 4454-4460
[21] L.Z. Zhang, Y.Y. Guo, D.S. Deng, Y. Ge, Experimental measurement and modeling of ternary vapor-liquid equilibrium for water + 1-propanol + 1-butyl-3-methylimidazolium chloride, J. Chem. Eng. Data 58 (1) (2013) 43-47
[22] L.Z. Zhang, J.Z. Han, R.J. Wang, X.Y. Qiu, J.B. Ji, Isobaric vapor-liquid equilibria for three ternary systems:Water + 2-propanol + 1-ethyl-3-methylimidazolium tetrafluoroborate, water + 1-propanol + 1-ethyl-3-methylimidazolium tetrafluoroborate, and water + 1-propanol + 1-butyl-3-methylimidazolium tetrafluoroborate, J. Chem. Eng. Data 52 (4) (2007) 1401-1407
[23] Y.F. Dai, Y.X. Qu, S. Wang, J.D. Wang, Measurement, correlation, and prediction of vapor pressure for binary and ternary systems containing an alkylsulfate-based ionic liquid, Fluid Phase Equilibria 397 (2015) 58-67
[24] A.B. Pereiro, F. Santamarta, E. Tojo, A. Rodríguez, J. Tojo, Temperature dependence of physical properties of ionic liquid 1, 3-dimethylimidazolium methyl sulfate, J. Chem. Eng. Data 51 (3) (2006) 952-954
[25] M. Cumplido, E. Lladosa, S. Loras, J. Pla-Franco, Isobaric vapor-liquid equilibria for extractive distillation of 1-propanol + water mixture using thiocyanate-based ionic liquids, J. Chem. Thermodyn. 113 (2017) 219-228
[26] Z.Y. Zhu, Y. Ri, M. Li, H. Jia, Y.K. Wang, Y.L. Wang, Extractive distillation for ethanol dehydration using imidazolium-based ionic liquids as solvents, Chem. Eng. Process.-Process. Intensif. 109 (2016) 190-198
[27] Z.Y. Zhu, Y. Ri, H. Jia, X. Li, Y. Wang, Y.L. Wang, Process evaluation on the separation of ethyl acetate and ethanol using extractive distillation with ionic liquid, Sep. Purif. Technol. 181 (2017) 44-52
[28] Z.Y. Zhu, X.L. Geng, W. He, C. Chen, Y.L. Wang, J. Gao, Computer-aided screening of ionic liquids as entrainers for separating methyl acetate and methanol via extractive distillation, Ind. Eng. Chem. Res. 57 (29) (2018) 9656-9664
[29] X.Q. You, I. Rodriguez-Donis, V. Gerbaud, Improved design and efficiency of the extractive distillation process for acetone-methanol with water, Ind. Eng. Chem. Res. 54 (1) (2015) 491-501
[30] J.O. Valderrama, R.E. Rojas, Critical properties of ionic liquids. Revisited, Ind. Eng. Chem. Res. 48 (14) (2009) 6890-6900
[31] Y. Huang, H.F. Dong, X.P. Zhang, C.S. Li, S.J. Zhang, A new fragment contribution-corresponding states method for physicochemical properties prediction of ionic liquids, AIChE J.59 (4) (2013) 1348-1359
[32] M. Królikowska, T. Hofman, Densities, isobaric expansivities and isothermal compressibilities of the thiocyanate-based ionic liquids at temperatures (298.15-338.15 K) and pressures up to 10 MPa, Thermochim. Acta 530 (2012) 1-6
[33] C. Shen, C.X. Li, X.M. Li, Y.Z. Lu, Y. Muhammad, Estimation of densities of ionic liquids using Patel-Teja equation of state and critical properties determined from group contribution method, Chem. Eng. Sci. 66 (12) (2011) 2690-2698
[34] J.F. Wang, C.X. Li, C. Shen, Z.H. Wang, Towards understanding the effect of electrostatic interactions on the density of ionic liquids, Fluid Phase Equilibria 279 (2) (2009) 87-91
[35] W.F. Shen, H. Benyounes, V. Gerbaud, Extension of thermodynamic insights on batch extractive distillation to continuous operation. 1. Azeotropic mixtures with a heavy entrainer, Ind. Eng. Chem. Res. 52 (12) (2013) 4606-4622
[36] W.L. Luyben, I.L. Chien, Design and Control of Distillation Systems for Separating Azeotropes, John Wiley & Sons, New York, 2010
[37] X.Q. You, J.L. Gu, V. Gerbaud, C.J. Peng, H.L. Liu, Optimization of pre-concentration, entrainer recycle and pressure selection for the extractive distillation of acetonitrile-water with ethylene glycol, Chem. Eng. Sci. 177 (2018) 354-368
[38] Y.L. Liu, J. Zhai, L.M. Li, L.Y. Sun, C. Zhai, Heat pump assisted reactive and azeotropic distillations in dividing wall columns, Chem. Eng. Process.:Process.Intensif. 95 (2015) 289-301
[39] M.A. Gadalla, Z. Olujic, P.J. Jansens, M. Jobson, R. Smith, Reducing CO₂ emissions and energy consumption of heat-integrated distillation systems, Environ. Sci. Technol. 39 (17) (2005) 6860-6870
[40] A.K. Jana, A novel energy-efficient batch stripper:Thermodynamic feasibility, cost analysis and CO₂ emissions, Appl. Therm. Eng. 84 (2015) 292-300
[41] G. Theodosiou, N. Stylos, C. Koroneos, Integration of the environmental management aspect in the optimization of the design and planning of energy systems, J. Cleaner Prod. 106 (2015) 576-593
[42] J.P. Knapp, M.F. Doherty, Minimum entrainer flows for extractive distillation:A bifurcation theoretic approach, AIChE J. 40 (2) (1994) 243-268
[43] Y.F. Dai, Y.X. Qu, S. Wang, J.D. Wang, Measurement, correlation, and prediction of vapor pressure for binary and ternary systems containing an ionic liquid 1, 3-dimethylimidazolium methylsulfate, Fluid Phase Equilibria 385 (2015) 219-226
[44] V.N. Kiva, E.K. Hilmen, S. Skogestad, Azeotropic phase equilibrium diagrams:A survey, Chem. Eng. Sci. 58 (10) (2003) 1903-1953
[45] X.Q. You, I. Rodriguez-Donis, V. Gerbaud, Low pressure design for reducing energy cost of extractive distillation for separating diisopropyl ether and isopropyl alcohol, Chem. Eng. Res. Des. 109 (2016) 540-552
[46] X.Q. You, I. Rodriguez-Donis, V. Gerbaud, Extractive distillation process optimisation of the 1.0-1a class system, acetone-methanol with water, Computer Aided Chemical Engineering, 33 (2014) 1315-1320
[47] X.Q. You, J.L. Gu, C.J. Peng, W.F. Shen, H.L. Liu, Improved design and optimization for separating azeotropes with heavy component as distillate through energy-saving extractive distillation by varying pressure, Ind. Eng. Chem. Res. 56 (32) (2017) 9156-9166
[48] Z. Lelkes, P. Lang, B. Benadda, P. Moszkowicz, Feasibility of extractive distillation in a batch rectifier, AIChE J. 44 (4) (1998) 810-822