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Isobaric Vapor–Liquid Equilibrium Data for the Quaternary System of sec-Butyl Acetate + sec-Butyl Alcohol + Dimethyl Sulfoxide + 1-Ethyl-3-methylimidazolium Acetate at 101.3 kPa

Authors:
Xuemei Zhang
Xuemei Zhang
Xuemei Zhang
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Qiuhua Lyu
Qiuhua Lyu
Qiuhua Lyu
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Xianbao Cui at Tianjin University
Xianbao Cui
Chungui Jian
Chungui Jian
Chungui Jian
  • This person is not on ResearchGate, or hasn't claimed this research yet.
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Abstract and Figures

The isobaric vapor–liquid equilibrium (VLE) data for the quaternary system sec-butyl acetate (SBAC) + sec-butyl alcohol (SBA) + dimethyl sulfoxide (DMSO) + 1-ethyl-3-methylimidazolium acetate ([EMIm][OAc]) were measured at 101.3 kPa. The non-random two liquid (NRTL) model was used to correlate the data and the binary interaction parameters were obtained. The correlation results agreed well with the experimental data. Compared with traditional organic solvents, the mixed solvent consisted of [EMIm][OAc] and DMSO performs better on improving the relative volatility of SBAC to SBA. The mixed solvent is a promising entrainer for the separation of SBAC–SBA mixtures by extractive distillation.
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Vol.:(0123456789)
Journal of Solution Chemistry (2022) 51:1409–1421
https://doi.org/10.1007/s10953-022-01200-z
1 3
Isobaric Vapor–Liquid Equilibrium Data fortheQuaternary
System ofsec‑Butyl Acetate + sec‑Butyl Alcohol + Dimethyl
Sulfoxide + 1‑Ethyl‑3‑methylimidazolium Acetate
at101.3kPa
XuemeiZhang1· QiuhuaLyu1· XianbaoCui1,2· ChunguiJian3
Received: 16 March 2022 / Accepted: 18 August 2022 / Published online: 6 September 2022
© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2022
Abstract
The isobaric vapor–liquid equilibrium (VLE) data for the quaternary system sec-butyl ace-
tate (SBAC) + sec-butyl alcohol (SBA) + dimethyl sulfoxide (DMSO) + 1-ethyl-3-methyl-
imidazolium acetate ([EMIm][OAc]) were measured at 101.3kPa. The non-random two
liquid (NRTL) model was used to correlate the data and the binary interaction parameters
were obtained. The correlation results agreed well with the experimental data. Compared
with traditional organic solvents, the mixed solvent consisted of [EMIm][OAc] and DMSO
performs better on improving the relative volatility of SBAC to SBA. The mixed solvent is
a promising entrainer for the separation of SBAC–SBA mixtures by extractive distillation.
Keywords sec-Butyl acetate· sec-Butyl alcohol· Dimethyl sulfoxide· 1-Ethyl-3-
methylimidazolium acetate· Vapor–liquid equilibrium
1 Introduction
sec-Butyl acetate (SBAC) and sec-butyl alcohol (SBA) are important chemical materials
and intermediates. SBAC is an excellent solvent in some fields, like pharmaceuticals, var-
nish and so on [1]. SBA can be used as raw material in the production of methyl ethyl
ketone by dehydrogenation. Besides, it can also be employed as gasoline additives, wetting
agents, and plasticizers [2, 3].
SBA can be produced by transesterification of SBAC [4, 5]. Traditional separation
method is distillation. However, when the mole fraction of SBA is higher than 0.9, the rela-
tive volatility of SBAC to SBA is close to 1 [6–8]. Thus, it is difficult to separate SBAC and
SBA by conventional distillation. Extractive distillation is an efficient process to separate
close-boiling and azeotropic systems [6, 9–12]. It is essential to select a suitable solvent for
* Xianbao Cui
cxb_0302@126.com
1 School ofChemical Engineering andTechnology, Tianjin University, 300350Tianjin, China
2 State Key Laboratory ofChemical Engineering, Tianjin University, 300350Tianjin, China
3 Peiyang Chemical Equipment Co., Ltd, 300072Tianjin, People’sRepublicofChina
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The double salt ionic liquid (DSIL) [EMIM][Cl]0.5[DCA]0.5, which was made by mixing 1-ethyl-3-methylimidazolium chloride ([EMIM][Cl]) and 1-ethyl-3-methylimidazolium dicyanamide ([EMIM][DCA]), was used for the separation of the methyl acetate + methanol azeotropic mixture. Isobaric vapor−liquid equilibrium (VLE) data for the ternary system of methyl acetate (1) + methanol (2) + [EMIM][Cl]0.5[DCA]0.5 (3) were measured at 101.3 kPa. The DSIL [EMIM][Cl]0.5[DCA]0.5 produced significant salting-out effect to methyl acetate and was able to break the azeotropic point of methyl acetate + methanol at low concentration of DSIL. The Non-Random Two-Liquid (NRTL) activity coefficient model was adopted to correlate the vapor−liquid equilibrium (VLE) data using three different objective functions, and the parameters of NRTL model were obtained based on the best objective function. Isobaric vapor−liquid equilibrium (VLE) data for the ternary systems of methyl acetate (1) + methanol (2) + [EMIM][Cl] (3) and methyl acetate (1) + methanol (2) + [EMIM][DCA] (3) were also measured at 101.3 kPa. The separation effects of DSIL [EMIM][Cl]0.5[DCA]0.5 were compared with the single ionic liquids [EMIM][Cl] and [EMIM][DCA].
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Experimental isobaric vapour-liquid equilibrium data for binary systems of {sec-butyl acetate (SBAC) + acetamide} and {sec-butyl alcohol (SBA) + acetamide} and the ternary system of (SBAC + SBA + acetamide) at 101.3 kPa
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Experimental isobaric vapour-liquid equilibrium data for the binary system N, (N-dimethyl acetamide + dimethyl sulfoxide) and the quaternary system (sec-butyl acetate + sec-butyl alcohol + N, N-dimethyl acetamide + dimethyl sulfoxide) at 101.3 kPa
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Isobaric vapour-liquid equilibrium (VLE) data for the binary system of {N, N-dimethyl acetamide (DMAC) + dimethyl sulfoxide (DMSO)} and the quaternary system of {sec-butyl acetate (SBAC) + sec-butyl alcohol (SBA) + DMAC + DMSO} were measured at 101.3 kPa using a modified Othmer still. The thermodynamic consistency test for the binary experimental data was checked by Van Ness point test. The experimental VLE data of the binary system were correlated with Wilson, NRTL and UNIQUAC activity coefficient models. The binary and quaternary VLE data predicted by the binary interaction parameters agreed well with the experimental data. And the mixed solvent (DMAC + DMSO) can eliminate the pseudo-azeotrope of SBAC and SBA. Thus the mixture of (DMAC + DMSO) is a potential extractive solvent in the separation of the pseudo-azeotrope of SBAC and SBA by extractive distillation.
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Effect of Ionic Liquids on the Binary Vapor–Liquid Equilibrium of Ethyl Acetate + Methanol System at 101.3 kPa
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Three ionic liquids (ILs) (1-ethyl-3-methylimidazolium bromide, [EMIM]Br; 1-ethyl-3-methylimidazolium chloride, [EMIM]Cl; and 1-ethyl-3-methylimidazolium acetate, [EMIM][Ac]) were used for the separation of the ethyl acetate + methanol azeotropic mixture. The vapor-liquid equilibrium (VLE) data of ethyl acetate + methanol azeotropic mixtures containing ILs were measured at 101.3 kPa. The three ILs show significant salting-out effects on ethyl acetate. The azeotropic point of the ethyl acetate + methanol azeotropic system is eliminated when the mole content of IL reaches a special value. The separation abilities of the three ILs follow the order [EMIM][Ac] > [EMIM]Cl > [EMIM]Br. The experimental data are correlated well by the nonrandom two-liquid model.
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The ionic liquids 1-methyl-3-octylimidazoliumbis (trifluoromethylsulfonyl)imide ([OMIM][Tf2N]) and 1,2-dimethyl-3-octylimidazolium bis(trifluoromethylsulfonyl)imide ([OMMIM][Tf2N]) were utilized as extractive distillation entrainers to make methanol as the volatile component for the separation of the azeotropic mixture of methanol and methyl acetate. Isobaric VLE data for the methanol (1) + methyl acetate (2) + [OMIM][Tf2N] and methanol (1) + methyl acetate (2) + [OMMIM][Tf2N] were measured at 101.3 kPa. The experimental data were correlated by NRTL model and UNIFAC model, and the NRTL model is more accurate. Both [OMIM][Tf2N] and [OMMIM][Tf2N] produce notable salting-out effects and make methanol as the volatile component, and the azeotropic point of methanol + methyl acetate can be eliminated if the mole fraction of [OMMIM][Tf2N] or [OMIM][Tf2N] is greater than 0.4. The mechanism of [OMMIM][Tf2N] and [OMIM][Tf2N] to improve the relative volatility of methanol to methyl acetate were investigated, and the salting-out effects of [OMMIM][Tf2N] is a little larger.
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