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

Tetrafluoroborate System at 101.3 kPa

Article  in  Journal of Chemical & Engineering Data · November 2012

DOI: 10.1021/je3007138

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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.

■ INTRODUCTION
Anhydrous ethanol is an important chemical reagent and
technology. The ILs investigated for this purpose include 1,3-
dimethylimidazolium dimethylphosphate
organic material in many chemical processes. But the presence ([MMIM]+[DMP]−),18 1-butyl-3-methylimidazolium tetra-
of azeotropic phenomenon at atmospheric pressure formed by fluoroborate ([BMIM]+[BF4]−),19,20 1-ethyl-3-methylimidazo-
ethanol and water makes it difficult to produce anhydrous lium tetrafluoroborate ([EMIM]+[BF4]−),19,20 1-butyl-3-meth-
ethanol from the aquous solution by simple distillation. In this ylimidazolium dicyanamide ([BMIM]+[N(CN)2]−),20 1-ethyl-
case, special distillation processes (e.g., extractive distillation 3-methylimidazolium dicyanamide ([EMIM]+[N(CN)2]−),20 1-
and azeotropic distillation) are commonly applied for the butyl-3-methylimidazolium chloride ([BMIM]+[Cl]−),19−21 1-
separation of ethanol and water, where a third component ethyl-3-methylimidazolium chloride ([EMIM]+[Cl]−),19 1-
(namely entrainer, solvent or separating agent) is added into butyl-3-methylimidazolium acetate ([BMIM]+[OAc]−),19 1-
the mixture to increase the relative volatility of ethanol to water. ethyl-3-methylimidazolium acetate ([EMIM]+[OAc]−),20 1-
It is generally thought that extractive distillation is preferred hexyl-3-methylimidazolium chloride ([HMIM]+[Cl]−),21−23 1-
over azeotropic distillation in that the entrainer does not need ethyl-3-methylpyridinium ethylsulfate [EMpy]+[EtSO4]−),24 1-
to be evaporated in the solvent recovery column so that more butyl-3-methylimidazolium methylsulfate
energy consumption can be saved.1−5 ([BMIM]+[MeSO4]−),25 1-ethyl-3-methylimidazolium ethyl-
By far, there have been five kinds of entrainers used in sulfate ([EMIM]+[EtSO4]−),26 1-ethyl-3-methylimidazolium
extractive distillation, that is, traditional liquid solvents, solid trifluoromethanesulfonate ([EMIM]+[triflate]−),27 and 1-
salts, the mixtures of liquid solvents and solid salts, hyper- ethyl-3-methylimidazolium dicyanamide ([EMIM]+[DCA]−).28
branched polymers, and ionic liquids (ILs). Among others, the This work continues our study on measuring the VLE of
use of ILs as entrainers of extractive distillation has received ternary systems containing ILs. Herein, the IL [MEA]+[BF4]−
significant interest from both academia and industry in the past has been recently synthesized in laboratory according to the
few years, due to their unique advantages such as the liquid procedure shown in Scheme 1, and some important physical
state at or near room temperature, nonflammability, extremely properties at 303.2 K are: density ρ = 1.4905 g·cm−3, and liquid
low vapor pressure, indefinite recycling potential by flash viscosity η = 59.39 mPa·s.29 This IL was selected as an entrainer
distillation or stripping, good solvent ability for various for the separation of ethanol and water because it contains
materials, and thermal and chemical stabilities. Besides, ILs as hydroxyl group (i.e., −OH) on the cation and thus should exert
entrainers of extractive distillation comprise the advantages of double actions of strong hydrogen bond and salting effects on
both liquid solvents (easy operation) and solid salts (high the components to be separated. The COSMO-RS calculation
separation ability and no solvent loss) and thus should be paid also demonstrates that the IL possesses excellent separation
more attention.6−17 For the separation of ethanol and water
using extractive distillation with ILs, the ternary VLE data for Received: June 27, 2012
the ethanol (1) + water (2) + IL (3) are needed, which can Accepted: November 5, 2012
provide fundamental knowledge for developing this innovative

© XXXX American Chemical Society A dx.doi.org/10.1021/je3007138 | J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data Article

Scheme 1. Synthesis of [MEA]+[BF4]−

ability for aqueous solutions. Therefore, in this work, the Table 1. VLE Data for the Binary System of Ethanol (1) +
isobaric VLE data for the ethanol (1) + water (2) + Water (2) at 101.3 kPaa
[MEA]+[BF4]− (3) were measured at atmospheric pressure
T/K x1 y1 u(x) u(y) u(T)
(101.3 kPa), and the effect of [MEA]+[BF4]− on the separation
of ethanol and water was compared with those reported in the 373.1 0.000 0.000 0.0010 0.0010 0.2
359.2 0.119 0.518 0.0040 0.0060 0.2
literature. The measured ternary VLE data were correlated
357.3 0.154 0.539 0.0010 0.0050 0.1
using the NRTL model.

■
355.8 0.218 0.598 0.0030 0.0060 0.1
354.8 0.269 0.596 0.0030 0.0060 0.2
EXPERIMENTAL SECTION 354.5 0.322 0.624 0.0040 0.0070 0.2
Chemicals. The chemical reagents used were ethanol, 354.0 0.357 0.650 0.0040 0.0070 0.1
redistilled water, and [MEA]+[BF4]−. The AR grade ethanol 353.5 0.393 0.642 0.0020 0.0010 0.2
were purchased from Tianjin Damao Chemical Reagents Plant, 353.4 0.425 0.655 0.0010 0.0040 0.2
with a mass fraction purity of above 99.7 % which was again 353.2 0.440 0.661 0.0020 0.0040 0.1
checked by gas chromatography (GC 4000A, China) in our 351.5 0.557 0.683 0.0005 0.0070 0.2
laboratory, and thus were used without further purification. 351.4 0.650 0.741 0.0010 0.0040 0.2
Distilled water was degassed and filtered using a 0.2 μm 351.3 0.759 0.790 0.0060 0.0050 0.1
Millipore filter to remove dust. The IL [MEA]+[BF4]− was 351.2 0.865 0.867 0.0030 0.0030 0.2
351.2 1.000 1.000 0.0010 0.0010 0.1
provided by Shanghai Cheng Jie Chemical Co. Ltd., with a mass a
fraction purity of above 99.0 wt % observed by liquid The uncertainties of composition and temperature, i.e. u(x), u(y) and
chromatography. Furthermore, before the experiments, u(T) with 0.95 level of confidence, were listed. The maximum
expanded uncertainties of the temperature and composition measure-
[MEA]+[BF4]− was dried for 12 h at 333.15 K under a vacuum
ments were below 0.3 K and 0.0080 mol fraction.
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.

■ 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 Figure 1. Absolute deviations Δy1 = y(exp) − y(cal) between the
measured in this work agree well with those reported by Naoki experimental and the calculated (using the NRTL model) mole
et al.33 The maximum absolute deviation Δy1 between the fractions of ethanol in the vapor phase for the binary system of ethanol
experimental and the calculated (using the NRTL model) mole (1) + water (2) at 101.3 kPa: ●, this work with error bars representing
the extended uncertainty; ○, ref 33.
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 The activity coefficient of component i (γi), which reflects
system of ethanol (1) + water (2) + [MEA]+[BF4]− (3) at the effect of IL on solution nonideality, can be calculated by the
101.3 kPa with an increase of IL content at x3 = 0.05, 0.10, and following equation:
0.15. The experimental results are given in Table 2, comprising yP
the equilibrium mole fraction of IL in the liquid phase (x3), γi = i s
xiPi (1)
mole fraction of ethanol in the liquid phase on an IL-free basis
(x1′), mole fraction of ethanol in the vapor phase (y1), where P is the total pressure of equilibrium system, 101.3 kPa;
equilibrium temperature (T), activity coefficients of ethanol Psi is the vapor pressure of component i at equilibrium
(γ1) and water (γ2), and relative volatility of ethanol to water temperature, calculated by the Antoine equation where the
α12. Antoine constants of ethanol and water can be found from the
B dx.doi.org/10.1021/je3007138 | J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data Article

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
5.001 367.4 0.049 0.388 0.0020 0.0030 0.2 5.330 0.918 13.106
5.036 361.4 0.107 0.532 0.0003 0.0050 0.2 3.471 0.845 9.298
4.997 357.1 0.186 0.593 0.0030 0.0020 0.1 2.701 0.904 6.790
5.001 355.6 0.255 0.637 0.0020 0.0040 0.2 2.238 0.931 5.475
5.012 355.0 0.376 0.685 0.0020 0.0030 0.1 1.637 1.020 3.657
5.000 353.8 0.438 0.706 0.0020 0.0080 0.1 1.531 1.087 3.215
4.997 353.0 0.563 0.754 0.0090 0.0050 0.2 1.325 1.135 2.667
5.003 352.8 0.634 0.780 0.0030 0.0070 0.1 1.233 1.208 2.332
4.998 352.6 0.762 0.853 0.0050 0.0020 0.2 1.137 1.179 2.204
5.006 352.4 0.859 0.897 0.0030 0.0040 0.2 1.064 1.236 1.969
9.999 368.6 0.047 0.398 0.0020 0.0030 0.2 6.248 0.937 15.059
9.998 368.4 0.106 0.573 0.0010 0.0070 0.1 3.605 0.786 10.357
9.999 359.4 0.173 0.627 0.0040 0.0010 0.1 3.099 0.843 8.357
10.058 357.9 0.277 0.702 0.0020 0.0060 0.2 2.374 0.762 7.090
9.972 355.2 0.361 0.742 0.0050 0.0080 0.1 2.006 0.727 6.292
10.064 354.2 0.463 0.786 0.0060 0.0060 0.1 1.724 0.717 5.488
9.986 353.8 0.555 0.815 0.0010 0.0042 0.1 1.475 0.772 4.365
10.061 353.4 0.684 0.858 0.0065 0.0080 0.2 1.295 0.785 3.767
10.074 353.2 0.798 0.903 0.0001 0.0050 0.2 1.176 0.728 3.690
10.060 353.2 0.876 0.928 0.0060 0.0020 0.2 1.101 0.728 3.457
15.005 369.6 0.051 0.435 0.0010 0.0020 0.2 5.614 0.637 19.790
15.045 366.0 0.105 0.603 0.0030 0.0030 0.1 3.445 0.666 11.630
15.104 360.5 0.168 0.674 0.0030 0.0080 0.2 3.306 0.691 10.846
15.085 357.6 0.265 0.739 0.0050 0.0060 0.1 2.692 0.628 9.757
15.088 355.9 0.374 0.781 0.0050 0.0030 0.2 2.043 0.609 7.640
15.007 355.4 0.465 0.819 0.0030 0.0050 0.3 1.767 0.583 6.905
15.087 354.8 0.593 0.865 0.0050 0.0030 0.2 1.501 0.542 6.317
14.982 354.3 0.676 0.891 0.0020 0.0050 0.2 1.379 0.518 6.073
14.977 353.2 0.786 0.926 0.0020 0.0020 0.2 1.293 0.479 6.162
15.105 353.0 0.868 0.951 0.0040 0.0006 0.2 1.213 0.403 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) water (2) 0.40 −2216.0 + 6.7055·(T/K) 3698.8 + 4.2758·(T/K)
ethanol (1) [MEA]+[BF4]− (3) 0.30 −1398.81 −2389.94
water (2) [MEA]+[BF4]− (3) 0.30 −10628.29 −7513.67

literature.34 It should be noted that the composition of IL in Δgji, and the correlated results are given in Table 3, where the
vapor phase is assumed to be zero due to its nonvolatility. binary parameters of ethanol and water are taken from the
The relative volatility of ethanol (1) to water (2) α12 was also literature,36 and the values for α13 and α23 were set to be 0.3, as
calculated by the following equation: proposed by Ge et al.20
y1 /x1 The average relative deviation (ARD) is defined as
α12 =
y2 /x 2 (2) N
γiexp − γical
1
ARD(%) = ∑ ·100
Among the local composition models (e.g., Wilson, non- N i=1
γiexp (4)
random two-liquid (NRTL), universal quasichemical (UNI-
QUAC), and universal functional (UNIFAC)), the NRTL In this case, the ARD is 6.07 % for the binary system of ethanol
model has the most frequency for correlating the VLE data of (1) + water (2), while it is 6.36 % for the ternary system of
the systems containing ILs. Thus, in this work, this model was
ethanol (1) + water (2) + [MEA]+[BF4]− (3).
adopted with the following objective function (OF) minimized:
Figure 2 illustrates that [MEA]+[BF4]− can obviously break
N
the azeotropic point formed by ethanol and water at x1 ≈ 0.9 in
OF = ∑ |γiexp − γical| the absence of IL. This is due to the stronger interaction
i=1 (3)
between IL and water than between IL and ethanol. As the IL
where N is the number of data points. The Marquardt method concentration increases, the VLE lines are further away from
as in Press et al.35 was used to fit the model parameters Δgij and the diagonal. This means that in principle pure ethanol can be
C dx.doi.org/10.1021/je3007138 | J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data Article

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
Figure 4. T, x, y diagram for the ternary system of ethanol (1) + water
Underwood equation.37 (2) containing [MEA]+[BF4]− (3) at different IL concentrations: ●,
Figure 4 shows the T, x, y diagram of ethanol (1) + water (2) x1′ (x3 = 0); ○, y1 (x3 = 0); (a) ▲, x1′ (x3 = 0.05); △, y1 (x3 = 0.05);
+ [MEA]+[BF4]− (3). It can be seen that as the IL (b) ■, x1′ (x3 = 0.10); □, y1 (x3 = 0.10); (c) ◆, x1′ (x3 = 0.15); ◊, y1
concentration increases, the equilibrium temperature also (x3 = 0.15); solid lines, correlated using the NRTL model.
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 demonstrated that the relative volatility of ethanol to water
between energy quality and energy quantity consumed by follows the order of [MEA]+[BF4]− > [MMIM]+[DMP]− >
extractive distillation column. [BMIM]+[Cl]− > [EMIM]+[NTf2]− ≈ [EMIM]+[BF4]− ≈
Moreover, we go a further step to compare the separation [BMIM]+[BF4]−, [MEA]+[BF4]− exhibiting the highest sepa-
performance of [MEA]+[BF4]− with those reported in the ration ability among all of the ILs investigated in this study. But
literature at the same IL concentration (see Figure 5). It is it should be noted that some ILs reported for the separation of
D dx.doi.org/10.1021/je3007138 | J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data Article

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■
(21) Calvar, N.; Gonzalez, B.; Gomez, E.; Dominguez, A. Vapor-
Liquid Equilibria for the Ternary System Ethanol + Water + 1-Butyl-3-
AUTHOR INFORMATION methylimidazolium Chloride and the Corresponding Binary Systems
Corresponding Author at 101.3 kPa. J. Chem. Eng. Data 2006, 51, 2178−2181.
*Tel.: +86-1064433695. Fax: +86-1064419619. E-mail address: (22) Calvar, N.; Gonzalez, B.; Gomez, E.; Dominguez, A. Study of
leizhg@mail.buct.edu.cn. the behaviour of the azeotropic mixture ethanol-water with
Funding imidazolium-based ionic liquids. Fluid Phase Equilib. 2007, 259, 51−
This work was financially supported by the National Nature 56.
(23) Zhang, L.; Ge, Y.; Ji, D.; Ji, J. Experimental Measurement and
Science Foundation of China under Grant Nos. 21121064,
Modeling of Vapor-Liquid Equilibrium for Ternary Systems
21076008, and 21176010. Containing Ionic Liquids: A Case Study for the System Water +
Notes Ethanol + 1-Hexyl-3-methylimidazolium Chloride. J. Chem. Eng. Data
The authors declare no competing financial interest.

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