Isobaric Vapor–Liquid Equilibrium for the Ethanol + Water + 2

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Isobaric Vapor−Liquid Equilibrium for the Ethanol + Water + 2‑Aminoethanol Tetrafluoroborate System at 101.3 kPa Xing Liu, Zhigang Lei,* Tao Wang, Qunsheng Li, and Jiqin Zhu State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Box 266, Beijing, 100029, China ABSTRACT: Isobaric vapor−liquid equilibrium (VLE) data for the ethanol (1) + water (2) system containing the ionic liquid (IL) 2-aminoethanol tetrafluoroborate ([MEA]+[BF4]−) (3) at atmospheric pressure (101.3 kPa) were measured with a modified Othmer still. The results showed that the azeotropic point can be broken at a specific IL mole fraction, indicating a significant salting-out effect following the order of x3 = 0.15 > x3 = 0.10 > x3 = 0.05. The IL [MEA]+[BF4]− may be a promising entrainer for the separation of ethanol and water with extractive distillation because it exhibits the highest separation ability when compared with other entrainers previously reported. The commonly used nonrandom two-liquid (NRTL) model was used for correlating the measured ternary VLE data.

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INTRODUCTION Anhydrous ethanol is an important chemical reagent and organic material in many chemical processes. But the presence of azeotropic phenomenon at atmospheric pressure formed by ethanol and water makes it difficult to produce anhydrous ethanol from the aquous solution by simple distillation. In this case, special distillation processes (e.g., extractive distillation and azeotropic distillation) are commonly applied for the separation of ethanol and water, where a third component (namely entrainer, solvent or separating agent) is added into the mixture to increase the relative volatility of ethanol to water. It is generally thought that extractive distillation is preferred over azeotropic distillation in that the entrainer does not need to be evaporated in the solvent recovery column so that more energy consumption can be saved.1−5 By far, there have been five kinds of entrainers used in extractive distillation, that is, traditional liquid solvents, solid salts, the mixtures of liquid solvents and solid salts, hyperbranched polymers, and ionic liquids (ILs). Among others, the use of ILs as entrainers of extractive distillation has received significant interest from both academia and industry in the past few years, due to their unique advantages such as the liquid state at or near room temperature, nonflammability, extremely low vapor pressure, indefinite recycling potential by flash distillation or stripping, good solvent ability for various materials, and thermal and chemical stabilities. Besides, ILs as entrainers of extractive distillation comprise the advantages of both liquid solvents (easy operation) and solid salts (high separation ability and no solvent loss) and thus should be paid more attention.6−17 For the separation of ethanol and water using extractive distillation with ILs, the ternary VLE data for the ethanol (1) + water (2) + IL (3) are needed, which can provide fundamental knowledge for developing this innovative © XXXX American Chemical Society

technology. The ILs investigated for this purpose include 1,3dimethylimidazolium dimethylphosphate ([MMIM]+[DMP]−),18 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]+[BF4]−),19,20 1-ethyl-3-methylimidazolium tetrafluoroborate ([EMIM]+[BF4]−),19,20 1-butyl-3-methylimidazolium dicyanamide ([BMIM]+[N(CN)2]−),20 1-ethyl3-methylimidazolium dicyanamide ([EMIM]+[N(CN)2]−),20 1butyl-3-methylimidazolium chloride ([BMIM]+[Cl]−),19−21 1ethyl-3-methylimidazolium chloride ([EMIM]+[Cl]−),19 1butyl-3-methylimidazolium acetate ([BMIM]+[OAc]−),19 1ethyl-3-methylimidazolium acetate ([EMIM]+[OAc]−),20 1hexyl-3-methylimidazolium chloride ([HMIM]+[Cl]−),21−23 1ethyl-3-methylpyridinium ethylsulfate [EMpy]+[EtSO4]−),24 1butyl-3-methylimidazolium methylsulfate ([BMIM]+[MeSO4]−),25 1-ethyl-3-methylimidazolium ethylsulfate ([EMIM]+[EtSO4]−),26 1-ethyl-3-methylimidazolium trifluoromethanesulfonate ([EMIM]+[triflate]−),27 and 1ethyl-3-methylimidazolium dicyanamide ([EMIM]+[DCA]−).28 This work continues our study on measuring the VLE of ternary systems containing ILs. Herein, the IL [MEA]+[BF4]− has been recently synthesized in laboratory according to the procedure shown in Scheme 1, and some important physical properties at 303.2 K are: density ρ = 1.4905 g·cm−3, and liquid viscosity η = 59.39 mPa·s.29 This IL was selected as an entrainer for the separation of ethanol and water because it contains hydroxyl group (i.e., −OH) on the cation and thus should exert double actions of strong hydrogen bond and salting effects on the components to be separated. The COSMO-RS calculation also demonstrates that the IL possesses excellent separation Received: June 27, 2012 Accepted: November 5, 2012

A

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Scheme 1. Synthesis of [MEA]+[BF4]−

ability for aqueous solutions. Therefore, in this work, the isobaric VLE data for the ethanol (1) + water (2) + [MEA]+[BF4]− (3) were measured at atmospheric pressure (101.3 kPa), and the effect of [MEA]+[BF4]− on the separation of ethanol and water was compared with those reported in the literature. The measured ternary VLE data were correlated using the NRTL model.

Table 1. VLE Data for the Binary System of Ethanol (1) + Water (2) at 101.3 kPaa

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EXPERIMENTAL SECTION Chemicals. The chemical reagents used were ethanol, redistilled water, and [MEA]+[BF4]−. The AR grade ethanol were purchased from Tianjin Damao Chemical Reagents Plant, with a mass fraction purity of above 99.7 % which was again checked by gas chromatography (GC 4000A, China) in our laboratory, and thus were used without further purification. Distilled water was degassed and filtered using a 0.2 μm Millipore filter to remove dust. The IL [MEA]+[BF4]− was provided by Shanghai Cheng Jie Chemical Co. Ltd., with a mass fraction purity of above 99.0 wt % observed by liquid chromatography. Furthermore, before the experiments, [MEA]+[BF4]− was dried for 12 h at 333.15 K under a vacuum by the rotary evaporator to remove the volatile byproducts and water. The mass fraction of water in ILs was less than 400 ppm after drying, as determined by Karl Fischer titration (SC-6) in our laboratory. Apparatus and Procedure. The VLE data at 101.3 kPa were measured by a circulation vapor−liquid equilibrium still (a modified Othmer still), and the detailed description of experimental apparatus has been reported in our previous publications.30−32 The estimated experimental uncertainty in pressure, temperature, and composition were ± 0.01 kPa, ± 0.3 K, and ± 0.0090 mole fraction, respectively.

T/K

x1

y1

u(x)

u(y)

u(T)

373.1 359.2 357.3 355.8 354.8 354.5 354.0 353.5 353.4 353.2 351.5 351.4 351.3 351.2 351.2

0.000 0.119 0.154 0.218 0.269 0.322 0.357 0.393 0.425 0.440 0.557 0.650 0.759 0.865 1.000

0.000 0.518 0.539 0.598 0.596 0.624 0.650 0.642 0.655 0.661 0.683 0.741 0.790 0.867 1.000

0.0010 0.0040 0.0010 0.0030 0.0030 0.0040 0.0040 0.0020 0.0010 0.0020 0.0005 0.0010 0.0060 0.0030 0.0010

0.0010 0.0060 0.0050 0.0060 0.0060 0.0070 0.0070 0.0010 0.0040 0.0040 0.0070 0.0040 0.0050 0.0030 0.0010

0.2 0.2 0.1 0.1 0.2 0.2 0.1 0.2 0.2 0.1 0.2 0.2 0.1 0.2 0.1

a The uncertainties of composition and temperature, i.e. u(x), u(y) and u(T) with 0.95 level of confidence, were listed. The maximum expanded uncertainties of the temperature and composition measurements were below 0.3 K and 0.0080 mol fraction.

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RESULTS AND DISCUSSION The binary VLE data for ethanol (1) + water (2) were first measured at atmospheric pressure (101.3 kPa), and the experimental results are listed in Table 1, where x1 and y1 represent the mole fractions of ethanol in the liquid and vapor phases, respectively. Figure 1 illustrates that the VLE data measured in this work agree well with those reported by Naoki et al.33 The maximum absolute deviation Δy1 between the experimental and the calculated (using the NRTL model) mole fractions of ethanol in the vapor phase was less than 0.030, thus verifying the reliability of our apparatus and experiment method. In the similar way, measurements were made for the ternary system of ethanol (1) + water (2) + [MEA]+[BF4]− (3) at 101.3 kPa with an increase of IL content at x3 = 0.05, 0.10, and 0.15. The experimental results are given in Table 2, comprising the equilibrium mole fraction of IL in the liquid phase (x3), mole fraction of ethanol in the liquid phase on an IL-free basis (x1′), mole fraction of ethanol in the vapor phase (y1), equilibrium temperature (T), activity coefficients of ethanol (γ1) and water (γ2), and relative volatility of ethanol to water α12.

Figure 1. Absolute deviations Δy1 = y(exp) − y(cal) between the experimental and the calculated (using the NRTL model) mole fractions of ethanol in the vapor phase for the binary system of ethanol (1) + water (2) at 101.3 kPa: ●, this work with error bars representing the extended uncertainty; ○, ref 33.

The activity coefficient of component i (γi), which reflects the effect of IL on solution nonideality, can be calculated by the following equation: yP γi = i s xiPi (1) where P is the total pressure of equilibrium system, 101.3 kPa; Psi is the vapor pressure of component i at equilibrium temperature, calculated by the Antoine equation where the Antoine constants of ethanol and water can be found from the B

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Table 2. VLE Data for the Ternary System of Ethanol (1) + Water (2) + [MEA]+[BF4]− (3) System at 101.3 kPaa 100 x3

T/K

x1′

y1

u(x)

u(y)

u(T)

γ1

γ2

α12

5.001 5.036 4.997 5.001 5.012 5.000 4.997 5.003 4.998 5.006 9.999 9.998 9.999 10.058 9.972 10.064 9.986 10.061 10.074 10.060 15.005 15.045 15.104 15.085 15.088 15.007 15.087 14.982 14.977 15.105

367.4 361.4 357.1 355.6 355.0 353.8 353.0 352.8 352.6 352.4 368.6 368.4 359.4 357.9 355.2 354.2 353.8 353.4 353.2 353.2 369.6 366.0 360.5 357.6 355.9 355.4 354.8 354.3 353.2 353.0

0.049 0.107 0.186 0.255 0.376 0.438 0.563 0.634 0.762 0.859 0.047 0.106 0.173 0.277 0.361 0.463 0.555 0.684 0.798 0.876 0.051 0.105 0.168 0.265 0.374 0.465 0.593 0.676 0.786 0.868

0.388 0.532 0.593 0.637 0.685 0.706 0.754 0.780 0.853 0.897 0.398 0.573 0.627 0.702 0.742 0.786 0.815 0.858 0.903 0.928 0.435 0.603 0.674 0.739 0.781 0.819 0.865 0.891 0.926 0.951

0.0020 0.0003 0.0030 0.0020 0.0020 0.0020 0.0090 0.0030 0.0050 0.0030 0.0020 0.0010 0.0040 0.0020 0.0050 0.0060 0.0010 0.0065 0.0001 0.0060 0.0010 0.0030 0.0030 0.0050 0.0050 0.0030 0.0050 0.0020 0.0020 0.0040

0.0030 0.0050 0.0020 0.0040 0.0030 0.0080 0.0050 0.0070 0.0020 0.0040 0.0030 0.0070 0.0010 0.0060 0.0080 0.0060 0.0042 0.0080 0.0050 0.0020 0.0020 0.0030 0.0080 0.0060 0.0030 0.0050 0.0030 0.0050 0.0020 0.0006

0.2 0.2 0.1 0.2 0.1 0.1 0.2 0.1 0.2 0.2 0.2 0.1 0.1 0.2 0.1 0.1 0.1 0.2 0.2 0.2 0.2 0.1 0.2 0.1 0.2 0.3 0.2 0.2 0.2 0.2

5.330 3.471 2.701 2.238 1.637 1.531 1.325 1.233 1.137 1.064 6.248 3.605 3.099 2.374 2.006 1.724 1.475 1.295 1.176 1.101 5.614 3.445 3.306 2.692 2.043 1.767 1.501 1.379 1.293 1.213

0.918 0.845 0.904 0.931 1.020 1.087 1.135 1.208 1.179 1.236 0.937 0.786 0.843 0.762 0.727 0.717 0.772 0.785 0.728 0.728 0.637 0.666 0.691 0.628 0.609 0.583 0.542 0.518 0.479 0.403

13.106 9.298 6.790 5.475 3.657 3.215 2.667 2.332 2.204 1.969 15.059 10.357 8.357 7.090 6.292 5.488 4.365 3.767 3.690 3.457 19.790 11.630 10.846 9.757 7.640 6.905 6.317 6.073 6.162 6.882

a

The uncertainties of composition and temperature, that is, u(x), u(y), and u(T) with 0.95 level of confidence, were listed. The maximum expanded uncertainties of the temperature and composition measurements were below 0.3 K and 0.0090 mole fraction.

Table 3. Estimated Values of Binary Parameters in the NRTL Model, Δgij and Δgji Δgij

Δgji

component i

component j

αij

J·mol−1

J·mol−1

ethanol (1) ethanol (1) water (2)

water (2) [MEA]+[BF4]− (3) [MEA]+[BF4]− (3)

0.40 0.30 0.30

−2216.0 + 6.7055·(T/K) −1398.81 −10628.29

3698.8 + 4.2758·(T/K) −2389.94 −7513.67

Δgji, and the correlated results are given in Table 3, where the binary parameters of ethanol and water are taken from the literature,36 and the values for α13 and α23 were set to be 0.3, as proposed by Ge et al.20 The average relative deviation (ARD) is defined as

literature.34 It should be noted that the composition of IL in vapor phase is assumed to be zero due to its nonvolatility. The relative volatility of ethanol (1) to water (2) α12 was also calculated by the following equation: α12 =

y1 /x1 y2 /x 2

(2)

ARD(%) =

Among the local composition models (e.g., Wilson, nonrandom two-liquid (NRTL), universal quasichemical (UNIQUAC), and universal functional (UNIFAC)), the NRTL model has the most frequency for correlating the VLE data of the systems containing ILs. Thus, in this work, this model was adopted with the following objective function (OF) minimized:

∑ |γiexp − γical| i=1

N

∑ i=1

γiexp − γical γiexp

·100 (4)

In this case, the ARD is 6.07 % for the binary system of ethanol (1) + water (2), while it is 6.36 % for the ternary system of ethanol (1) + water (2) + [MEA]+[BF4]− (3). Figure 2 illustrates that [MEA]+[BF4]− can obviously break the azeotropic point formed by ethanol and water at x1 ≈ 0.9 in the absence of IL. This is due to the stronger interaction between IL and water than between IL and ethanol. As the IL concentration increases, the VLE lines are further away from the diagonal. This means that in principle pure ethanol can be

N

OF =

1 N

(3)

where N is the number of data points. The Marquardt method as in Press et al.35 was used to fit the model parameters Δgij and C

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Figure 2. Isobaric VLE diagram for the ethanol (1) + water (2) + [MEA]+[BF4]− (3) system at 101.3 kPa: ○, x3 = 0; ●, x3 = 0.05; ▲, x3 = 0.10; ◆, x3 = 0.15; solid lines, correlated using the NRTL model.

produced by extractive distillation with [MEA]+[BF4]− as an entrainer. The relative volatility of ethanol to water is enhanced upon the addition of IL, as shown in Figure 3. The higher the IL

Figure 3. Relative volatility of ethanol (1) to water (2) at 101.3 kPa at different IL concentrations: ○, x3 = 0; ●, x3 = 0.05; ▲, x3 = 0.10; ◆, x3 = 0.15; solid lines, correlated using the NRTL model.

concentration, the more pronounced the salting-out effect. It follows the order of x3 = 0.15 > x3 = 0.10 > x3 = 0.05, indicating that a high IL concentration is favorable for the separation of ethanol and water because the extractive distillation column could be operated at a small reflux ratio according to the Underwood equation.37 Figure 4 shows the T, x, y diagram of ethanol (1) + water (2) + [MEA]+[BF4]− (3). It can be seen that as the IL concentration increases, the equilibrium temperature also increases, leading to a high reboiler temperature at the bottom of extractive distillation column. That is to say, there exists a suitable feed/solvent ratio, determined by the compromise between energy quality and energy quantity consumed by extractive distillation column. Moreover, we go a further step to compare the separation performance of [MEA]+[BF4]− with those reported in the literature at the same IL concentration (see Figure 5). It is

Figure 4. T, x, y diagram for the ternary system of ethanol (1) + water (2) containing [MEA]+[BF4]− (3) at different IL concentrations: ●, x1′ (x3 = 0); ○, y1 (x3 = 0); (a) ▲, x1′ (x3 = 0.05); △, y1 (x3 = 0.05); (b) ■, x1′ (x3 = 0.10); □, y1 (x3 = 0.10); (c) ◆, x1′ (x3 = 0.15); ◊, y1 (x3 = 0.15); solid lines, correlated using the NRTL model.

demonstrated that the relative volatility of ethanol to water follows the order of [MEA]+[BF4]− > [MMIM]+[DMP]− > [BMIM]+[Cl]− > [EMIM]+[NTf2]− ≈ [EMIM]+[BF4]− ≈ [BMIM]+[BF4]−, [MEA]+[BF4]− exhibiting the highest separation ability among all of the ILs investigated in this study. But it should be noted that some ILs reported for the separation of D

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(4) Li, M. Equilibrium Calculation of Gaseous Reactive Systems with Simultaneous Species Adsorption. Ind. Eng. Chem. Res. 2008, 47, 9263−9271. (5) Li, M.; Duraiswamy, K.; Knobbe, M. Adsorption Enhanced Methanol Reforming in Conjunction with Fuel Cell: Process Design and Reactor Dynamics. Chem. Eng. Sci. 2012, 67, 26−33. (6) Pereiro, A. B.; Araujo, J. M. M.; Esperanca, J. M. S. S.; Marrucho, I. M.; Rebelo, L. P. N. Ionic liquids in separations of azeotropic systems-A review. J. Chem. Thermodyn. 2012, 46, 2−28. (7) Lei, Z. G.; Arlt, W.; Wasserscheid, P. Separation of 1-hexene and n-hexane with ionic liquids. Fluid Phase Equilib. 2006, 241, 290−299. (8) Lei, Z. G.; Arlt, W.; Wasserscheid, P. Selection of entrainers in the 1-hexene/n-hexane system with a limited solubility. Fluid Phase Equilib. 2007, 260, 29−35. (9) Jork, C.; Kristen, C.; Pieraccini, D.; Stark, A.; Chiappe, C.; Beste, Y. A.; Arlt, W. Tailor-made ionic liquids. J. Chem. Thermodyn. 2005, 37, 537−558. (10) Welton, T. Room-temperature Ionic Liquids. Solvents for Synthesis and Catalysts. Chem. Rev. 1999, 99, 2071−2083. (11) Heintz, A. Recent developments in thermodynamics and thermophysics of non-aqueous mixtures containing ionic liquids. A review. J. Chem. Thermodyn. 2005, 37, 525−535. (12) Brennecke, J. F.; Maginn, E. J. Ionic liquids: Innovative fluids for chemical processing. AIChE J. 2001, 47, 2384−2389. (13) Baker, G. A.; Banker, S. N.; Pandey, S.; Bright, F. V. An analytical view of ionic liquids. Analyst 2005, 130, 800−808. (14) Han, X. X.; Armstrong, D. W. Ionic Liquids in Separations. Acc. Chem. Res. 2007, 40, 1079−1086. (15) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; WileyVCH: Weinheim, 2003. (16) Marsh, K. N.; Boxall, J. A.; Lichtenthaler, R. Room temperature ionic liquids and their mixtures-a review. Fluid Phase Equilib. 2004, 219, 93−98. (17) Poole, C. F.; Poole, S. K. Extraction of organic compounds with room temperature ionic liquids. J. Chromatogr., A 2010, 1217, 2268− 2286. (18) Li, Q.; Zhu, W.; Wang, H.; Ran, X.; Fu, Y.; Wang, B. Isobaric Vapor-Liquid Equilibrium for the Ethanol + Water + 1,3Dimethylimidazolium Dimethylphosphate System at 101.3 kPa. J. Chem. Eng. Data 2012, 57, 696−700. (19) Seiler, M.; Jork, C.; Kavarnou, A.; Arlt, W.; Hirsch, R. Separation of azeotropic mixtures using hyperbranched polymers or ionic liquids. AIChE J. 2004, 50, 2439−2454. (20) Ge, Y.; Zhang, L.; Yuan, X.; Geng, W.; Ji, J. Selection of Ionic Liquids as Entrainers for Separation of Water and Ethanol. J. Chem. Thermodyn. 2008, 40, 1248−1252. (21) Calvar, N.; Gonzalez, B.; Gomez, E.; Dominguez, A. VaporLiquid Equilibria for the Ternary System Ethanol + Water + 1-Butyl-3methylimidazolium Chloride and the Corresponding Binary Systems at 101.3 kPa. J. Chem. Eng. Data 2006, 51, 2178−2181. (22) Calvar, N.; Gonzalez, B.; Gomez, E.; Dominguez, A. Study of the behaviour of the azeotropic mixture ethanol-water with imidazolium-based ionic liquids. Fluid Phase Equilib. 2007, 259, 51− 56. (23) Zhang, L.; Ge, Y.; Ji, D.; Ji, J. Experimental Measurement and Modeling of Vapor-Liquid Equilibrium for Ternary Systems Containing Ionic Liquids: A Case Study for the System Water + Ethanol + 1-Hexyl-3-methylimidazolium Chloride. J. Chem. Eng. Data 2009, 54, 2322−2329. (24) Calvar, N.; Gonzalez, B.; Gomez, E.; Dominguez, A. Experimental Vapor-Liquid Equilibria for the Ternary System Ethanol + Water + 1-Ethyl-3-methylpyridinium Ethylsulfate and the Corresponding Binary Systems at 101.3 kPa: Study of the Effect of the Cation. J. Chem. Eng. Data 2010, 55, 2786−2791. (25) Calvar, N.; Gonzalez, B.; Gomez, E.; Dominguez, A. VaporLiquid Equilibria for the Ternary System Ethanol + Water + 1-Butyl-3methylimidazolium Methylsulfate and the Corresponding Binary Systems at 101.3 kPa. J. Chem. Eng. Data 2009, 54, 1004−1008.

Figure 5. Relative volatility of ethanol (1) to water (2) with IL as an entrainer at x3 = 0.10 at 101.3 kPa. ●, [MEA]+[BF4]− (this work); △, [MMIM]+[DMP]− (ref 18); □, [EMIM]+[NTf2]− (ref 27); ▽, [BMIM] + [BF 4 ] − (ref 22); ○ , [BMIM] + [Cl] − (ref 21); ◊ , [EMIM]+[BF4]− (ref 22).

ethanol and water are not given in Figure 5 because the experimental conditions are different.

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CONCLUSIONS This work focuses on measuring the isobaric VLE data for the ternary system of ethanol (1) + water (2) + [MEA]+[BF4]− (3) at 101.3 kPa, and the following conclusions can be concluded: (i) The VLE data at various IL concentrations are present, showing that [MEA]+[BF4]− can eliminate the azeotropic phenomenon, and the salting-out effect follows the order of x3 = 0.15 > x3 = 0.10 > x3 = 0.05. (ii) The NRTL model is capable for describing the experimental VLE data satisfactorily, with the ARD of 6.07 % for the binary system of ethanol (1) + water (2) and 6.36 % for the ternary system of ethanol (1) + water (2) + [MEA]+[BF4]− (3). (iii) It was found that [MEA]+[BF4]− exhibits the highest separation in comparison with other ILs reported previously. The isobaric VLE data obtained in this work are important for the design, control, and optimization of extractive distillation column so as to separate ethanol and water efficiently and effectively.

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AUTHOR INFORMATION

Corresponding Author

*Tel.: +86-1064433695. Fax: +86-1064419619. E-mail address: [email protected]. Funding

This work was financially supported by the National Nature Science Foundation of China under Grant Nos. 21121064, 21076008, and 21176010. Notes

The authors declare no competing financial interest.

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REFERENCES

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dx.doi.org/10.1021/je3007138 | J. Chem. Eng. Data XXXX, XXX, XXX−XXX