Systematic screening procedure and innovative energy-saving design for ionic liquid-based extractive distillation process
Tuanjie Shen, Liumei Teng, Yanjie Hu, Weifeng Shen
Systematic screening procedure and innovative energy-saving design for ionic liquid-based extractive distillation process
In the traditional extractive distillation process, organic solvents are often used as entrainers. However, environmental influence and high energy-consumption are significant problems in industrial application. In this study, a systematic screening strategy and innovative energy-saving design for ionic liquid-based extractive distillation process was proposed. The innovative energy-saving design focused on the binary minimum azeotrope mixtures isopropanol and water. Miscibility, environmental impact and physical properties (e.g., melting point and viscosity) of 30 ionic liquids were investigated. 1-Ethyl-3-methyl-imidazolium dicyanamide and 1-butyl-3-methyl-imidazolium dicyanamide were selected as candidate entrainers. Feasibility analysis of these two ionic liquids was further performed via residue curve maps, isovolatility line and temperature profiles. An innovative ionic liquid-based extractive distillation process combining distillation column and stripping column was designed and optimized with the objective function of minimizing the total annualized cost. The results demonstrate that the total annualized cost was reduced by 19.9% with 1-ethyl-3-methyl-imidazolium dicyanamide as the entrainer and by 24.3% with 1-butyl-3-methyl-imidazolium dicyanamide, compared with that of dimethyl sulfoxide. The method proposed in this study is conducive to the green and sustainable development of extractive distillation process.
ionic liquid / entrainer screening / feasibility analysis / extractive distillation
[1] |
Qiu T, Zhang P, Yang J B, Xiao L, Ye C S. Novel procedure for production of isopropanol by transesterification of isopropyl acetate with reactive distillation. Industrial & Engineering Chemistry Research, 2014, 53(36): 13881–13891
CrossRef
Google scholar
|
[2] |
Arifin S, Chien I L. Design and control of an isopropyl alcohol dehydration process via extractive distillation using dimethyl sulfoxide as an entrainer. Industrial & Engineering Chemistry Research, 2008, 47(3): 790–803
CrossRef
Google scholar
|
[3] |
Shi T, Chun W, Yang A, Su Y, Jin S, Ren J, Shen W. Isobaric vapor-liquid equilibria for the extractive distillation of 2-propanol + water mixtures using 1-ethyl-3-methylimidazolium dicyanamide ionic liquid. Journal of Chemical Thermodynamics, 2017, 110: 16–24
CrossRef
Google scholar
|
[4] |
Gerbaud V, Rodriguez-Donis I, Hegely L, Lang P, Denes F, You X Q. Optimization and control of energy saving side-stream extractive distillation with heat integration for separating ethyl acetate-ethanol azeotrope. Chemical Engineering Science, 2020, 215: 115373
CrossRef
Google scholar
|
[5] |
Yang A, Su Y, Shi T, Ren J Z, Shen W F, Zhou T. Energy-efficient recovery of tetrahydrofuran and ethyl acetate by triple-column extractive distillation: entrainer design and process optimization. Frontiers of Chemical Science and Engineering, 2022, 16(2): 303–315
CrossRef
Google scholar
|
[6] |
Su Y, Yang A, Jin S, Shen W, Cui P, Ren J. Investigation on ternary system tetrahydrofuran/ethanol/water with three azeotropes separation via the combination of reactive and extractive distillation. Journal of Cleaner Production, 2020, 273(5760): 123145
CrossRef
Google scholar
|
[7] |
Graczová E, Šulgan B, Barabas S, Steltenpohl P. Methyl acetate-methanol mixture separation by extractive distillation: economic aspects. Frontiers of Chemical Science and Engineering, 2018, 12(4): 670–682
CrossRef
Google scholar
|
[8] |
Li H, Sun G L, Li D Y, Xi L, Zhou P, Li X G, Zhang J, Gao X. Molecular interaction mechanism in the separation of a binary azeotropic system by extractive distillation with ionic liquid. Green Energy & Environment, 2021, 6(3): 329–338
CrossRef
Google scholar
|
[9] |
Li H, Zhou P, Zhang J, Li D Y, Li X G, Gao X. A theoretical guide for screening ionic liquid extractants applied in the separation of a binary alcohol-ester azeotrope through a DFT method. Journal of Molecular Liquids, 2018, 251: 51–60
CrossRef
Google scholar
|
[10] |
Gao X, Geng X L. Application of the chemical-looping concept for azoetrope separation. Engineering, 2021, 7(1): 84–93
CrossRef
Google scholar
|
[11] |
Zhou T, Song Z, Zhang X, Gani R, Sundmacher K. Optimal solvent design for extractive distillation processes: a multiobjective optimization-based hierarchical framework. Industrial & Engineering Chemistry Research, 2019, 58(15): 5777–5786
CrossRef
Google scholar
|
[12] |
Hegely L, Lang P. Influence of entrainer recycle for batch heteroazeotropic distillation. Frontiers of Chemical Science and Engineering, 2018, 12(4): 643–659
CrossRef
Google scholar
|
[13] |
Wu Y C, Hsu P H C, Chien I L. Critical assessment of the energy-saving potential of an extractive dividing-wall column. Industrial & Engineering Chemistry Research, 2013, 52(15): 5384–5399
CrossRef
Google scholar
|
[14] |
Chang W T, Huang C T, Cheng S H. Design and control of a complete azeotropic distillation system incorporating stripping columns for isopropyl alcohol dehydration. Industrial & Engineering Chemistry Research, 2012, 51(7): 2997–3006
CrossRef
Google scholar
|
[15] |
Liang K, Li W S, Luo H T, Xia M, Xu C J. Energy-efficient extractive distillation process by combining preconcentration column and entrainer recovery column. Industrial & Engineering Chemistry Research, 2014, 53(17): 7121–7131
CrossRef
Google scholar
|
[16] |
Wang S J, Chen W Y, Chang W T, Hu C C, Cheng S H. Optimal design of mixed acid esterification and isopropanol dehydration systems via incorporation of dividing-wall columns. Chemical Engineering and Processing, 2014, 85: 108–124
CrossRef
Google scholar
|
[17] |
Lek-utaiwan P, Suphanit B, Douglas P L, Mongkolsiri N. Design of extractive distillation for the separation of close-boiling mixture: solvent selection and column optimization. Computers & Chemical Engineering, 2011, 35(6): 1088–1100
CrossRef
Google scholar
|
[18] |
Gupta K M, Jiang J W. Cellulose dissolution and regeneration in ionic liquids: a computational perspective. Chemical Engineering Science, 2015, 121(6): 180–189
CrossRef
Google scholar
|
[19] |
Zhao H, Baker G A. Oxidative desulfurization of fuels using ionic liquids: a review. Frontiers of Chemical Science and Engineering, 2015, 9(3): 262–279
CrossRef
Google scholar
|
[20] |
Song Z, Li X X, Chao H, Mo F, Zhou T, Cheng H Y, Chen L F, Qi Z W. Computer-aided ionic liquid design for alkane/cycloalkane extractive distillation process. Green Energy & Environment, 2019, 4(2): 154–165
CrossRef
Google scholar
|
[21] |
Huang Y Q, Zhang Y B, Xing H B. Separation of light hydrocarbons with ionic liquids: a review. Chinese Journal of Chemical Engineering, 2019, 27(6): 1374–1382
CrossRef
Google scholar
|
[22] |
Seiler M, Jork C, Kavarnou A, Arlt W, Hirsch R. Separation of azeotropic mixtures using hyperbranched polymers or ionic liquids. AIChE Journal, 2004, 50(10): 2439–2454
CrossRef
Google scholar
|
[23] |
Chen H H, Chen M K, Chen B C, Chien I L. Critical assessment of using an ionic liquid as entrainer via extractive distillation. Industrial & Engineering Chemistry Research, 2017, 56(27): 7768–7782
CrossRef
Google scholar
|
[24] |
Kulajanpeng K, Suriyapraphadilok U, Gani R. Systematic screening methodology and energy efficient design of ionic liquid-based separation processes. Journal of Cleaner Production, 2016, 111: 93–107
CrossRef
Google scholar
|
[25] |
Gutiérrez J P, Meindersma G W, de Haan A B. COSMO-RS-based ionic-liquid selection for extractive distillation processes. Industrial & Engineering Chemistry Research, 2012, 51(35): 11518–11529
CrossRef
Google scholar
|
[26] |
Bernot R J, Brueseke M A, Evans-White M A, Lamberti G A. Acute and chronic toxicity of imidazolium-based ionic liquids on daphnia magna. Environmental Toxicology and Chemistry, 2005, 24(1): 87–92
CrossRef
Google scholar
|
[27] |
Couling D J, Bernot R J, Docherty K M, Dixon J K, Maginn E J. Toxicological evaluation of ionic liquid in a biological functional tissue construct model based on nano-hydroxyapatite/chitosan/gelatin hybrid scaffolds. International Journal of Biological Macromolecules, 2020, 158(1): 800–810
|
[28] |
Pretti C, Chiappe C, Baldetti I, Brunini S, Monni G, Intorre L. Acute toxicity of ionic liquids for three freshwater organisms: Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio. Ecotoxicology and Environmental Safety, 2009, 72(4): 1170–1176
CrossRef
Google scholar
|
[29] |
You X Q, Gu J L, Peng C J, Shen W F, Liu H L. Improved design and optimization for separating azeotropes with heavy component as distillate through energy-saving extractive distillation by varying pressure. Industrial & Engineering Chemistry Research, 2017, 56(32): 9156–9166
CrossRef
Google scholar
|
[30] |
Rodriguez-Donis I, Gerbaud V, Joulia X. Thermodynamic insights on the feasibility of homogeneous batch extractive distillation. 1. Azeotropic mixtures with a heavy entrainer. Industrial & Engineering Chemistry Research, 2009, 48(7): 3544–3559
CrossRef
Google scholar
|
[31] |
Turton R, Bailie R C, Whiting W B, Shaeiwitz J A. Analysis, Synthesis and Design of Chemical Processes. 3rd ed. New York: Pearson Education, 2009,
|
[32] |
William L L, Chien I L. Design and Control of Distillation Systems for Separating Azeotropes. New York: John Wiley & Sons, 2010,
|
[33] |
Navarro P, Larriba M, García J, Rodríguez F. Design of the recovery section of the extracted aromatics in the separation of BTEX from naphtha feed to ethylene crackers using [4empy][Tf2N] and [emim][DCA] mixed ionic liquids as solvent. Separation and Purification Technology, 2017, 180: 149–156
CrossRef
Google scholar
|
[34] |
Swatloski R P, Holbrey J D, Rogers R D. Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate. Green Chemistry, 2003, 5(4): 361–363
CrossRef
Google scholar
|
[35] |
Himmler S, Hörmann S, van Hal R, Schulz P S, Wasserscheid P. Transesterification of methylsulfate and ethylsulfate ionic liquids—an environmentally benign way to synthesize long-chain and functionalized alkylsulfate ionic liquids. Green Chemistry, 2006, 8(10): 887–894
CrossRef
Google scholar
|
[36] |
Awad W H, Gilman J W, Nyden M, Jr R H H, Sutto T E, Callahan J, Trulove P C, De Long H C, Fox D M. Thermal degradation studies of alkylimidazolium salts and their application in nanocomposites. Thermochimica Acta, 2004, 409(1): 3–11
CrossRef
Google scholar
|
[37] |
Ngo H L, LeCompte K, Hargens L, McEwen A B. Thermal properties of imidazolium ionic liquids. Thermochimica Acta, 2000, 357-358: 97–102
CrossRef
Google scholar
|
[38] |
Lopes J M, Sánchez F A, Reartes S B R, Bermejo M D, Martín Á, Cocero M J. Melting point depression effect with CO2 in high melting temperature cellulose dissolving ionic liquids. modeling with group contribution equation of state. Journal of Supercritical Fluids, 2016, 107: 590–604
CrossRef
Google scholar
|
[39] |
Domańska U, Pobudkowska A, Ecker F. Liquid-liquid equilibria in the binary systems (1,3-dimethylimidazolium, or 1-butyl-3-methylimidazolium methylsulfate + hydrocarbons). Green Chemistry, 2006, 8(3): 268–276
CrossRef
Google scholar
|
[40] |
Wendler F, Todi L N, Meister F. Thermostability of imidazolium ionic liquids as direct solvents for cellulose. Thermochimica Acta, 2012, 528: 76–84
CrossRef
Google scholar
|
[41] |
Lazzús J, Pulgar-Villarroel G. A group contribution method to estimate the viscosity of ionic liquids at different temperatures. Journal of Molecular Liquids, 2015, 209: 161–168
CrossRef
Google scholar
|
[42] |
Wan Normazlan W M D, Sairi N A, Alias Y, Udaiyappan A F, Jouyban A, Khoubnasabjafari M. Composition and temperature dependence of density, durface tension, and viscosity of EMIM DEP/MMIM DMP + water + 1-propanol/2-propanol ternary mixtures and their mathematical representation using the Jouyban−Acree model. Journal of Chemical & Engineering Data, 2014, 59(8): 2337–2348
CrossRef
Google scholar
|
[43] |
Groff D, George A, Sun N, Sathitsuksanoh N, Bokinsky G, Simmons B A, Holmes B M, Keasling J D. Acid enhanced ionic liquid pretreatment of biomass. Green Chemistry, 2013, 15(5): 1264–1267
CrossRef
Google scholar
|
[44] |
Shi J, Gladden J M, Sathitsuksanoh N, Kambam P, Sandoval L, Mitra D, Zhang S, George A, Singer S W, Simmons B A, Singh S. One-pot ionic liquid pretreatment and saccharification of switchgrass. Green Chemistry, 2013, 15(9): 2579–2589
CrossRef
Google scholar
|
[45] |
Montalbán M G, Hidalgo J M, Collado-González M, Díaz Baños F G, Víllora G. Assessing chemical toxicity of ionic liquids on Vibrio fischeri: correlation with structure and composition. Chemosphere, 2016, 155: 405–414
CrossRef
Google scholar
|
[46] |
Arning J, Stolte S, Böschen A, Stock F, Pitner W R, Welz-Biermann U, Jastorff B, Ranke J. Qualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalised side chains and anions of ionic liquids on acetylcholinesterase. Green Chemistry, 2008, 10: 47–58
CrossRef
Google scholar
|
[47] |
Matzke M, Stolte S, Thiele K, Juffernholz T, Arning J, Ranke J, Welz-Biermannd U, Jastorff B. The influence of anion species on the toxicity of ionic liquids observed in an (eco)toxicological test battery. Green Chemistry, 2006, 8: 621–629
|
[48] |
Yoshida Y, Baba O, Saito G. Ionic liquids based on dicyanamide anion: influence of structural variations in cationic structures on ionic conductivity. Journal of Physical Chemistry B, 2007, 111(18): 4742–4749
CrossRef
Google scholar
|
[49] |
Wasserscheid P, Welton T. Ionic Liquid in Synthesis. New York: John Wiley & Sons, 2002,
|
[50] |
Navarro P, Larriba M, Rojo E, García J, Rodríguez F. Thermal properties of cyano-based ionic liquids. Journal of Chemical & Engineering Data, 2013, 58(8): 2187–2193
CrossRef
Google scholar
|
[51] |
Valderrama J O, Forero L A, Rojas R E. Extension of a group contribution method to estimate the critical properties of ionic liquids of high molecular mass. Industrial & Engineering Chemistry Research, 2015, 54(13): 3480–3487
CrossRef
Google scholar
|
[52] |
Ge R, Hardacre C, Jacquemin J, Nancarrow P, Rooney D W. Heat capacities of ionic liquids as a function of temperature at 0.1 MPa. Measurement and prediction. Journal of Chemical & Engineering Data, 2008, 53(9): 2148–2153
CrossRef
Google scholar
|
[53] |
Zhang L Z, Han J Z, Deng D S, Ji J B. Selection of ionic liquids as entrainers for separation of water and 2-propanol. Fluid Phase Equilibria, 2007, 255(2): 179–185
CrossRef
Google scholar
|
/
〈 | 〉 |