Methyl acetate–methanol mixture separation by extractive distillation: Economic aspects

Elena Graczová, Branislav Šulgan, Samuel Barabas, Pavol Steltenpohl

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Front. Chem. Sci. Eng. ›› 2018, Vol. 12 ›› Issue (4) : 670-682. DOI: 10.1007/s11705-018-1769-9
RESEARCH ARTICLE
RESEARCH ARTICLE

Methyl acetate–methanol mixture separation by extractive distillation: Economic aspects

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Abstract

Methyl acetate is considered low toxicity volatile solvent produced either as a by-product during methanol carbonylation or via acetic acid esterification with methanol. In both cases, pure methyl acetate has to be isolated from the reaction mixture. Simulation of methyl acetate separation from its mixture with methanol by extraction distillation was carried out in ASPEN+ software. In total three case studies were assumed using two different extraction solvents and two solvent regeneration strategies. In case A, novel extraction solvent 1-ethyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid, was considered. Raw material separation was achieved in an extraction distillation column while the solvent regeneration was accomplished in a second distillation column in this case. In case study B, the same extraction solvent was used; however, its regeneration was carried out in a single-effect evaporator. Dimethyl sulfoxide was the second extraction solvent selected. Its use in methyl acetate-methanol separation is presented in case study C. As high purity of dimethyl sulfoxide was required for the methyl acetate-methanol azeotrope breaking, its regeneration was carried out in the second distillation column only. To simulate the ternary methyl acetate–methanol–extraction solvent mixtures separation, vapor–liquid equilibrium was predicted based on the NRTL equation. Further, unknown properties of the considered ionic liquid and variation of these properties with temperature were predicted and introduced into the ASPEN+ components properties database. Based on these data, optimum operation parameters of the respective separation equipment were established. In all case studies, the same condition had to be fulfilled, namely minimum methyl acetate content in the distillate from the extraction distillation column of 99.5mol-%. Results of simulations using the respective optimum operation parameters were employed in the economic evaluation of the three separation unit designs studied. It was found that the least energy-demanding design corresponds to the case study B in terms of both capital as well as operation expenses.

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Keywords

methyl acetate / 1-ethyl-3-methylimidazolium trifluoromethanesulfonate / extraction distillation / dimethyl sulfoxide / economic evaluation

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Elena Graczová, Branislav Šulgan, Samuel Barabas, Pavol Steltenpohl. Methyl acetate–methanol mixture separation by extractive distillation: Economic aspects. Front. Chem. Sci. Eng., 2018, 12(4): 670‒682 https://doi.org/10.1007/s11705-018-1769-9

References

[1]
Agreda V H, Partin L R, Heise W H. High-purity methyl acetate via reactive distillation. Chemical Engineering Progress, 1990, 86(2): 40–46
[2]
Huss R S, Chen F R, Malone M F, Doherty M F. Reactive distillation for methyl acetate production. Computers & Chemical Engineering, 2003, 27(12): 1855–1866
CrossRef Google scholar
[3]
Giwa A. Methyl acetate reactive distillation process modeling, simulation and optimization using ASPEN Plus. Journal of Engineering and Applied Sciences (Asian Research Publishing Network), 2013, 8(5): 386–392
[4]
Rohde C, Marr R, Siebenhofer M. Investigation of methyl acetate production by reactive extraction. In: Proceedings of the AIChE Annual Meeting 2004. Austin: AIChE, 2004, 5113–5118
[5]
Lux S, Winkler T, Siebenhofer M. Synthesis and isolation of methyl acetate through heterogeneous catalysis with liquid–liquid extraction. Industrial & Engineering Chemistry Research, 2010, 49(21): 10274–10278
CrossRef Google scholar
[6]
Cao Y J, Li M, Wang Y, Zhao T R, Li X, Zhu Z Y, Wang Y L. Effect of feed temperature on economics and controllability of pressure-swing distillation for separating binary azeotrope. Chemical Engineering and Processing: Process Intensification, 2016, 110: 160–171
CrossRef Google scholar
[7]
Berg L, Yeh A I. The separation of methyl acetate from methanol by extractive distillation. Chemical Engineering Communications, 1984, 30(1–2): 113–117
CrossRef Google scholar
[8]
Lei Z G, Li C Y, Chen B H. Extractive distillation: A review. Separation and Purification Reviews, 2003, 32(2): 121–213
CrossRef Google scholar
[9]
Mahdi T, Ahmad A, Nasef M M, Ripin A. State-of-the-art technologies for separation of azeotropic mixtures. Separation and Purification Reviews, 2015, 44(4): 308–330
CrossRef Google scholar
[10]
Schuur B. Selection and design of ionic liquids as solvents in extractive distillation and extractive processes. Chemical Papers, 2015, 69(2): 245–253
CrossRef Google scholar
[11]
Jongmans M T G, Hermens E, Raijmakers M, Maassen J I W, Schuur B, de Haan A B. Conceptual process design of extractive distillation processes for ethylbenzene/styrene separation. Chemical Engineering Research & Design, 2012, 90(12): 2086–2100
CrossRef Google scholar
[12]
Jongmans M T G, Trampé J, Schuur B, de Haan A B. Solute recovery from ionic liquids: A conceptual design study for recovery of styrene monomer from [4-mebupy][BF4]. Chemical Engineering and Processing: Process Intensification, 2013, 70: 148–161
CrossRef Google scholar
[13]
Li G Z, Bai P. New operation strategy for separation of ethanol-water by extractive distillation. Industrial & Engineering Chemistry Research, 2012, 51(6): 2723–2729
[14]
Quijada-Maldonado E, Aelmans T A M, Meindersma G W, de Haan A B. Pilot plant validation of a rate-based extractive distillation model for water–ethanol separation with the ionic liquid [emim][DCA] as solvent. Chemical Engineering Journal, 2013, 223: 287–297
CrossRef Google scholar
[15]
Gutierrez H J P. Extractive distillation with ionic liquids as solvents: Selection and conceptual process design. Dissertation for the Doctoral Degree. Eindhoven: Eindhoven University of Technology, 2013, 137–139
[16]
Meindersma G W, Quijada-Maldonado E, Jongmans M, de Haan A B. Extractive distillation with ionic liquids: Pilot plant experiments and conceptual process design. In: Ionic Liquids for Better Separation Processes. Berlin: Springer, 2016, 11–38
[17]
Dhanalakshmi J, Sai P S T, Balakrishnan A R. Study of ionic liquids as entrainers for the separation of methyl acetate–methanol and ethyl acetate–ethanol systems using the COSMO-RS model. Industrial & Engineering Chemistry Research, 2013, 52(46): 16396–16405
CrossRef Google scholar
[18]
Zhang Z G, Hu A G, Zhang T, Zhang Q Q, Sun M Y, Sun D Z, Li W X. Separation of methyl acetate+ methanol azeotropic mixture using ionic liquids as entrainers. Fluid Phase Equilibria, 2015, 401: 1–8
CrossRef Google scholar
[19]
Orchillés A V, Miguel P J, Vercher E, Martínez-Andreu A. Isobaric vapor–liquid equilibria for methyl acetate+ methanol+ 1-ethyl-3-methylimidazolium trifluoromethanesulfonate at 100 kPa. Journal of Chemical & Engineering Data, 2007, 52(3): 915–920
CrossRef Google scholar
[20]
Cai J L, Cui X B, Zhang Y, Li R, Feng T Y. Vapor–liquid equilibrium and liquid–liquid equilibrium of methyl acetate+ methanol+ 1-ethyl-3-methylimidazolium acetate. Journal of Chemical & Engineering Data, 2011, 56(2): 282–287
CrossRef Google scholar
[21]
Cai J L, Cui X B, Zhang Y, Li R, Feng T Y. Isobaric vapor liquid equilibrium for methanol+ methyl acetate+ 1-octyl-3-methylimidazolium hexafluorophosphate at 101.3 kPa. Journal of Chemical & Engineering Data, 2011, 56(2): 2884–2888
CrossRef Google scholar
[22]
Matsuda H, Tochigi K, Liebert V, Gmehling J. Vapor–liquid equilibria of ternary systems with 1-ethyl-3-methylimidazolium ethyl sulfate using headspace gas chromatography. Fluid Phase Equilibria, 2011, 307(2): 197–201
CrossRef Google scholar
[23]
Dohnal V, Baránková E, Blahut A. Separation of methyl acetate+ methanol azeotropic mixture using ionic liquid entrainers. Chemical Engineering Journal, 2014, 237: 199–208
CrossRef Google scholar
[24]
Zhang Z G, Hu A G, Zhang T, Zhang Q Q, Yang Z Q, Li W X. Isobaric vapor–liquid equilibrium for methyl acetate+ methanol system containing different ionic liquids at 101.3 kPa. Fluid Phase Equilibria, 2016, 408: 20–26
CrossRef Google scholar
[25]
Cao J, Yu G G, Chen X C, Abdeltawab A A, Al-Enizi A M. Determination of vapor–liquid equilibrium of methyl acetate+ methanol+ 1-alkyl-3-methylimidazolium dialkylphosphates at 101.3 kPa. Journal of Chemical & Engineering Data, 2017, 62(2): 816–824
CrossRef Google scholar
[26]
Zhang X M, Liu H P, Liu Y X, Jian C G, Wang W. Experimental isobaric vapor–liquid equilibrium for the binary and ternary systems with methanol, methyl acetate and dimethyl sulfoxide at 101.3 kPa. Fluid Phase Equilibria, 2016, 408: 52–57
CrossRef Google scholar
[27]
Hsieh C T, Lee M J, Lin H M. Vapor–liquid–liquid equilibria for aqueous systems with methyl acetate, methyl propionate, and methanol. Industrial & Engineering Chemistry Research, 2008, 47(20): 7927–7933
CrossRef Google scholar
[28]
Crawford A G, Edwards G, Lindsay D S. The ternary system, methanol–methyl acetate–water. Journal of the Chemical Society, 1949: 1054–1058
CrossRef Google scholar
[29]
Gmehling J, Onken U. Vapor–Liquid Equilibrium Data Collection. Chemistry Data Series, Vol. I, Part 1. Frankfurt/Main: DECHEMA, 1977, 37–76, 258–264
[30]
Pereiro A B, Araújo J M M, Esperança J M S S, Marrucho I M, Rebelo L P N. Ionic liquids in separations of azeotropic systems—A review. Journal of Chemical Thermodynamics, 2012, 46: 2–28
CrossRef Google scholar
[31]
Rogers R D, Seddon K R. Ionic liquids—solvents of the future? Science, 2003, 302(5646): 792–793
CrossRef Google scholar
[32]
Huddleston J G, Visser A E, Reichert W M, Willauer H D, Broker G A, Rogers R D. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chemistry, 2001, 3(4): 156–164
CrossRef Google scholar
[33]
Humphrey J L, Keller G E II. Separation Process Technology. New York: McGraw-Hill, 1997, 1
[34]
Blahušiak M, Kiss A A, Babic K, Kersten S R A, Bargeman G, Schuur B. Insights into the selection and design of fluid separation processes. Separation and Purification Technology, 2018, 194: 301–318
CrossRef Google scholar
[35]
Steltenpohl P, Graczová E. Optimization of extraction solvent-to-feed ratio: Aqueous ethanol mixture separation using [TDTHP][NTf2] ionic liquid. Chemical Engineering Research & Design, 2017, 121: 200–206
CrossRef Google scholar
[36]
de Riva J, Ferro V R, Moreno D, Diaz I, Palomar J. Aspen Plus supported conceptual design of the aromatic–aliphatic separation from low aromatic content naphtha using 4-methyl-N-butylpyridinium tetrafluoroborate ionic liquid. Fuel Processing Technology, 2016, 146: 29–38
CrossRef Google scholar
[37]
Larriba M, de Riva J, Navarro P, Moreno D, Delgado-Mellado N, García J, Ferro V R, Rodríguez F, Palomar J. COSMO-based/Aspen Plus process simulation of the aromatic extraction from pyrolysis gasoline using the {[4empy][NTf2] + [emim][DCA]} ionic liquid mixture. Separation and Purification Technology, 2018, 190: 211–227
CrossRef Google scholar
[38]
Graczová E, Dobcsányi D, Steltenpohl P. Separation of methyl acetate–methanol azeotropic mixture using 1-ethyl-3-methylimidazolium trifluoromethanesulfonate. Chemical Engineering Transactions, 2017, 61: 1183–1188
[39]
Boston J F, Sullivan S L Jr. A new class of solution methods for multicomponent, multistage separation processes. Canadian Journal of Chemical Engineering, 1974, 52(1): 52–63
CrossRef Google scholar
[40]
Seader J D, Henley E J, Roper D K. Separation Process Principles. 3rd ed. New Jersey: Wiley, 2010, 400–412
[41]
Renon H, Prausnitz J M. Local compositions in thermodynamic excess functions for liquid mixtures. AIChE Journal. American Institute of Chemical Engineers, 1968, 14(1): 135–144
CrossRef Google scholar
[42]
Valderrama J O, Forero L A, Rojas R E. Critical properties and normal boiling temperature of ionic liquids. Update and a new consistency test. Industrial & Engineering Chemistry Research, 2012, 51(22): 7838–7844
CrossRef Google scholar
[43]
Papari M M, Amighi S, Kiani M, Mohammad-Aghaie D, Haghighi B. Modification of a statistical mechanically-based equation of state: Application to ionic liquids. Journal of Molecular Liquids, 2012, 175: 61–66
CrossRef Google scholar
[44]
Zhang S J, Lu X M, Zhou Q, Li X H, Zhang X P, Li S C. Ionic liquids. Physicochemical properties. Amsterdam: Elsevier, 2009, 47
[45]
Zaitsau D H, Kabo G J, Strechan A A, Paulechka Y U, Tschersich A, Verevkin S P, Heintz A. Experimental vapor pressures of 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides and a correlation scheme for estimation of vaporization enthalpies of ionic liquids. Journal of Physical Chemistry A, 2006, 110(22): 7303–7306
CrossRef Google scholar
[46]
Joback K G, Reid R C. Estimation of pure-component properties from group-contributions. Chemical Engineering Communications, 1987, 57(1-6): 233–243
CrossRef Google scholar
[47]
Retrieved from the website of Alibaba (methyl-acetate), January 10, 2018
[48]
Retrieved from the website of Intratec (methanol), January 10, 2018
[49]
Retrieved from the website of Alibaba (DMSO), January 10, 2018

Acknowledgement

This work was supported by the Research and Development Assistance Agency APVV (APVV-0858-12).

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2018 Higher Education Press and Springer-Verlag GmbH Germany, part of Springer Nature
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