Isobaric Vapor–Liquid Equilibria for Ethyl Acetate + Acetonitrile + 1

Article pubs.acs.org/jced

Isobaric Vapor−Liquid Equilibria for Ethyl Acetate + Acetonitrile + 1‑Butyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide at 101.3 kPa Qunsheng Li,*,† Jiujuan Zhu,† Yuxin Zhang,† Manman Li,† and Yudong Liu‡ †

State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Box 35, Beijing 100029, China China Huanqiu Contracting & Engineering Corporation, Beijing 100012, China

‡

ABSTRACT: Herein, we explored the isobaric vapor−liquid equilibrium (VLE) data of ethyl acetate + acetonitrile and ethyl acetate + acetonitrile+1-butyl-3methylimidazolium bis(trifluoromethylsulfonyl)imide ([BMIM][NTf2]). The VLE data were obtained in a CE-2 still (at 101.3 kPa). [BMIM][NTf2] effected a evident “salting-out effect”, altering relative volatility (α12), activity coefficient (γi), and minimum boiling point. The e-NRTL model, which was short for electrolyte-NRTL, was used to correlate with the experimental results. Furthermore, the parameters (aij, Δgij, Δgji) were obtained and there was a good consistency between experimental and correlated results. The needed amount of [BMIM][NTf2] was 0.027 as calculated by e-NRTL model to eliminate the azeotropy.

1. INTRODUCTION

2. EXPERIMENTAL SECTION 2.1. Materials. The used organic solvents (ethyl acetate (≥99.5%, mass fraction) and acetonitrile (≥99.8%)) were supplied by Tianjin Jinke Fine Chemical Industry Research Institute and Fuchen Chemical Reagents Factor, respectively, whereas [BMIM][NTf2](≥98.0%) was bought from Shanghai Chengjie Chemical Co. LTD (China). The volatile compounds in [BMIM][NTf2] were removed with vacuum evaporation for at least 24 h and the purity of IL was checked by liquid chromatography (LC). The purity quotient of used organic solvents were verified by GC and used directly. The specifications of used samples were listed in Table 1. 2.2. Equilibrium Measurement. The phase equilibria was surveyed through CE-2 still.11−17 The concentration of organic

Altering the relative volatility is the main design idea to separate the azeotrope or close-boiling mixtures. The appropriate extraction agent can make the separation more efficient.1 Ionic liquids (ILs) with excellent properties have been reported to be good candidate solvents for separating the azeotropy.2−8 Calvar2 investigated the osmotic coefficients and vapor pressures of [CnMIM][NTf2](n = 2, 3, and 4) with a binary systems 1-and 2propanol at 323.15 K. The osmotic coefficients are in sequence of [C4MIM][NTf2] > [C3MIM][NTf2] > [C2MIM][NTf2]. Through studying the propanone (1) + isopropanol (2) + [C2MIM][NTf2] (3) and isopropanol (1) + water (2) + [C2MIM][NTf2] (3) mixtures, and correlating VLE data using Wilson et al. models, Michael Döker4 proposed that [C2MIM][NTf2] is promising for the separating process. Moreover, ILs has also been found to be suitable for the purification of acetonitrile. Usually, it is hard to purify acetonitrile by conventional extractive distillation4,9,10 from the azeotrope of acetonitrile + ethyl acetate. With addition of ILs, the purification of acetonitrile becomes more facile. ILs, such as [BMIM][PF6],11 [EMIM][OTf],12 and [BMIM][OTf],13 can make the separation of ethyl acetate and acetonitrile at ILs mole fraction from 0.05 to 0.20, but how ILs influences the separation of azeotrope is still an open question and the experimental data is also not enough to chemical industrial design. Therefore, more detailed studied are strongly desired for separating azeotropic mixtures using ILs. In the present study, we explored the isobaric VLE of ethyl acetate + acetonitrile + [BMIM][NTf2], and the influence of [BMIM][NTf2] on the azeotrope was also investigated. The equilibrium data was further analyzed with e-NRTL. © XXXX American Chemical Society

Table 1. Specifications of Used Chemical Samples name

source

Ethyl Acetate

Tianjin Jinke Fine Chemical Industry Research Institute Fuchen Chemical Reagents Factor Shanghai Chengjie Chemical Co. LTD

Acetonitrile [BMIM] [NTf2] a

initial purity

purification method

final purity

analysis method

0.995

none

0.995

GCa

0.998

none

0.998

GCa

0.98

vacuum with rotary evaporator

0.9995

LCb

GC = gas chromatography. bLC = liquid chromatography.

Received: November 23, 2015 Accepted: September 27, 2016

A

DOI: 10.1021/acs.jced.5b00995 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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solvents were detected by GC (SP7800, China) by TCD detector with a packed Porapak-Q (3 m × 3 mm). The operating conditions of GC were as follows: injector temperature at 443.15 K, oven temperature 393.15 K, and detector temperature 453.15 K. The equilibrium pressure was atmospheric pressure and the VLE data were corrected to 101.3 kPa.16 The uncertainty of temperature was 0.1 K and pressure 0.1 kPa. A calibration curve was obtained to quantify the content of organic components. There, a set of pure substances standard solution was prepared gravimetrically with ethyl acetate molar fraction from 0.05 to 0.95 (0.05 per interval) and then a calibration curve was drawn whose ordinate was the response signal of total peak area (area normalization method) and abscissa was mole fraction. The calibration curve was a straight line through the origin (adjusted R2 0.9999). Therefore, the amounts of organic components in the vapor and liquid phase can be quantified through area response value interpolated to the calibration curve. For the containing IL system, IL was only in liquid phase. Therefore, the IL amount was gravimetrically determined with and without IL. With this analysis method, the maximum deviation was 0.002.

Figure 1. Influence of [BMIM][NTf2] (3) on VLE data (101.3 kPa). x3: ●, 0; ▼, 0.05; ◀, 0.10; ▶, 0.15; ○, ref 11; −, correlated values.

where P represents the system pressure (101.3 kPa), and PiS the component i vapor pressure calculated by Antoine equation18 with standard deviation (σ) 0.004. The ternary VLE results were analyzed with [BMIM][NTf2] mole fraction from 0.05 to 0.15 (an interval of 0.05 at 101.3 kPa). The consequence are listed in Table 3, where xi′ represents component i excluding IL. 3.2. Analysis Using e-NRTL Model. The employed eNRTL model was an extension of the NRTL.19 From the eNRTL model, Chen20 derived another model for single solvent− electrolyte systems for liquid phase activity coefficients. Later, Mock21,22 extended the model to mixed solvent−electrolyte systems by neglecting the long-range interaction contribution term (as shown from eqs 3 to 5). Therefore, the e-NRTL model can produce the expressions for activity coefficients (γi) of ethyl acetate (1) + acetonitrile (2)/ethyl acetate (1) + acetonitrile (2) + [BMIM][NTf2] (3) in the liquid phase. Herein, δ denotes the mean absolute deviations, and (δy/δT) are thermodynamically consistent by the e-NRTL model

3. RESULTS AND DISCUSSION 3.1. VLE Results. The binary VLE data are listed in Table 2 as well as illustrated in Figure 1. The binary results indicate that the Table 2. VLE Results of Temperature T, Liquid-/Vapor-Phase Mole Fractions xi and yi, Activity Coefficient γi, and Relative Volatility α12 for Ethyl Acetate (1) + Acetonitrile (2) at 101.3 kPaa T (K)

x1

y1

γ1

γ2

α12

352.45 350.65 349.95 349.15 348.75 348.55 348.45 348.45 348.85 349.15

0.079 0.186 0.289 0.388 0.490 0.547 0.596 0.697 0.862 0.902

0.125 0.263 0.360 0.446 0.530 0.577 0.614 0.696 0.843 0.886

1.459 1.395 1.256 1.189 1.138 1.115 1.094 1.059 1.024 1.019

1.024 1.033 1.051 1.085 1.116 1.140 1.169 1.229 1.370 1.389

1.650 1.562 1.381 1.266 1.177 1.129 1.080 0.995 0.863 0.847

ln γm =

∑j XjGjmτjm ∑k XkGkm

a

Standard uncertainties: uT = 0.1K, uP = 0.1 kPa, ux1/y1 = 0.002, uγi = 0.1.

+

∑∑ c

azeotropic composition (x1) is 0.695, whereas T is 348.5 K. As shown in Figure 1, there is a good consistency between experimental data and ref 11. Moreover, the binary results also comply with the point thermodynamic consistency test, indicating that the used experimental facility and approach herein is reliable. Because of the measurement at 101.3 kPa, the activity coefficient γi and relative volatility α12 are thereby calculated based on the following two assumptions: the behavior of component i is nonideal in liquid phase and ideal in vapor phase, respectively. The γi and α12 calculated equations are as follows: yP γi = i S xiPi (1) α12 =

y1 /x1 y2 /x 2

=

+

∑∑ a

c′

∑ m′

∑ XG τ ⎞ X m ′Gmm ′ ⎛ ⎜⎜τmm ′ − k k km ′ km ′ ⎟⎟ ∑k XkGkm ′ ⎝ ∑k XkGkm ′ ⎠

⎞ ∑ XG τ XcGmc , a ′ c ⎛ Xa ′ ⎜⎜τmc , a ′ c − k k kc , a ′ c kc , a ′ c ⎟⎟ ∑a ″ Xa ″ ∑a ″ XkGkc , a ′ c ⎝ ∑k XkGkc , a ′ c ⎠ ⎞ ∑ XG τ XaGma , c ′ a ⎛ Xc ′ ⎜⎜τma , c ′ a − k k ka , c ′ a ka , c ′ a ⎟⎟ ∑c ″ Xc ″ ∑a ″ XkGka , c ′ a ⎝ ∑k XkGka , c ′ a ⎠

(3)

where ⎛ gji − gii ⎞ τji = ⎜ ⎟ ⎝ RT ⎠

(4)

Gji = exp( −ajiτji) aij = aji

(5)

where aij denotes nonrandomness parameters and Δgij/Δgji denotes binary interaction parameters. To gain the phase equilibria data with ILs system by e-NRTL, it is essential to obtain the parameters (aij, Δgij, Δgji). The parameters of e-NRTL model for the studied binary and ternary systems were calculated through minimizing the objective function (OF), which was shown eq 6. The parameters (aij, Δgij, Δgji) of e-NRTL were calculated for (1) + (2) from the data

γ1P1S γ2P2S

a′

+

(2) B

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Table 3. VLE Results of Temperature T, Liquid-/Vapor-Phase Mole Fractions xi and yi, Liquid-Phase Mole Fraction of Ethyl Acetate Excluding [BMIM][NTf2] x1′, Activity Coefficient γi, and Relative Volatility α12 for Ethyl Acetate (1) + Acetonitrile (2) + (3) at 101.3 kPaa 100x3

T (K)

x1′

y1

γ1

γ2

α12

4.841 4.997 4.991 5.003 4.976 4.999 5.001 4.999 5.004 9.990 9.988 9.989 9.986 9.980 9.996 9.967 9.771 9.721 14.981 14.964 14.999 15.002 14.999 14.989 14.992 14.774

355.35 353.65 352.15 351.25 350.65 350.15 349.95 349.85 349.95 359.05 357.25 355.55 354.05 352.95 351.95 351.65 351.35 351.15 363.95 361.35 359.15 357.45 355.65 354.75 353.95 352.95

0.106 0.180 0.276 0.373 0.475 0.583 0.686 0.794 0.893 0.082 0.153 0.257 0.367 0.475 0.591 0.694 0.778 0.868 0.064 0.153 0.245 0.349 0.475 0.578 0.680 0.884

0.174 0.271 0.375 0.470 0.558 0.650 0.736 0.823 0.907 0.149 0.253 0.379 0.492 0.588 0.681 0.758 0.824 0.893 0.131 0.274 0.391 0.500 0.612 0.695 0.774 0.919

1.466 1.413 1.341 1.282 1.220 1.177 1.139 1.105 1.078 1.512 1.468 1.379 1.314 1.259 1.209 1.158 1.132 1.107 1.560 1.483 1.414 1.337 1.274 1.220 1.186 1.116

0.954 0.971 0.989 0.996 1.010 1.024 1.035 1.057 1.075 0.904 0.908 0.908 0.913 0.924 0.950 0.970 0.978 1.001 0.828 0.825 0.830 0.832 0.846 0.853 0.854 0.867

1.783 1.687 1.571 1.489 1.397 1.328 1.273 1.209 1.160 1.946 1.878 1.764 1.668 1.578 1.473 1.382 1.339 1.279 2.200 2.094 1.983 1.869 1.749 1.659 1.611 1.492

Figure 2. Effect of [BMIM][NTf2] (3) on relative volatility (a12) (101.3 kPa). x3: □, 0; ●, 0.05; ▲, 0.10; ▼, 0.15; −, correlated values.

a

Standard uncertainties: uT = 0.1K, uP = 0.1 kPa, ux1/y1 = 0.002, ux3 = 0.001, uγi = 0.1.

in Table 2 and for (1) + (3)/(2) + (3) were obtained from the data in Table 3, respectively ⎡⎛ ⎛ γ1 ⎞ γ2 ⎞ ⎢⎜ cal ⎟ ⎜ OF = ∑ ⎢ 1 − + 1 − cal ⎟ ⎜ ⎟ ⎜ γ γ2 ⎟⎠ 1exp ⎠ N ⎢ ⎝ exp ⎣⎝ 2

Figure 3. Effect of [BMIM][NTf2] (3) on T−(xi′, yi) data (101.3 kPa). x1′ − x3: □, 0; ○, 0.05; △, 0.10; ▽, 0.15. y1 − x3: ■, 0; ●, 0.05; ▲, 0.10; ▼, 0.15; −, correlated values.

2⎤

⎥ ⎥ ⎥⎦

(6)

(1) + acetonitrile (2) azeotropic mixtures. Similarly, the addition of [BMIM][NTf2] also enhances the relative volatility (a12) values (see Figure 2). This credits to the “salting-out effect” of [BMIM][NTf2] on ethyl acetate.23−26 Moreover, the enhancement is more evident with further increasing the amount of [BMIM][NTf2]. It is worthwhile noting that adding [BMIM][NTf2] produces a displacement of the binary azeotropic point x1′ higher until the azeotropy disappears (as shown in Figure 1 to 4). Moreover, it also causes the increase of equilibrium temperature at 101.3 kPa. The boiling point becomes higher with increasing the amount of

where exp and cal are short for experimental and calculated, N the points, and the sums can be extended to the whole points range. As all obtained parameters of e-NRTL model listed in Table 4, we can calculate the composition of studied binary and ternary system at any equilibrium temperature. Then, the experimental and simulated VLE values are compared as shown in Figures 1 to 4. As shown in Figure 1, it leads to a distinctly enhancive amount (y1) of ethyl acetate by adding [BMIM][NTf2] to ethyl acetate Table 4. Correlation Values of aij, Δgij, and Δgji of e-NRTL Model component i

j

aij

Δgij (J·mol−1)

Δgji(J·mol−1)

σa

ethyl acetate (1) ethyl acetate (1) acetonitrile (2)

acetonitrile (2) [BMIM][NTf2](3) [BMIM][NTf2](3)

0.30 0.30 0.30

2194.4 15742.9 9441.5

−1038.4 −4163.7 −7891.2

0.009 0.042 0.049

σ = [∑N (γcal − γexp)2 /(N − 1)]1/2

a

C

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Figure 5. Comparison diagram of T−(xi′, yi) for ethyl acetate (1) + acetonitrile (2) + 0.05IL (3) (101.3 kPa). x1′: □, [BMIM][NTf2]; ○, [BMIM][PF6];11 △, [EMIM][OTf];12 ▽, [BMIM][OTf].13 y1: ■, [BMIM][NTf2]; ●, [BMIM][PF6];11 ▲, [EMIM][OTf];12 ▼, [BMIM][OTf].13

Figure 4. Influence of [BMIM][NTf2] (3) on activity coefficients (γi) (101.3 kPa). γ1 − x3: ●, 0; ■, 0.05;▲, 0.10; ▼, 0.15. γ2 − x3: ○, 0; □, 0.05; △, 0.10; ▽, 0.15; −, correlated values.

[BMIM][NTf2] to ethyl acetate and acetonitrile system. This is consistent with the result of Sun et al.27 In terms of the experimental results, the ethyl acetate + acetonitrile azeotrope can be totally eliminated when the [BMIM][NTf2] concentration is up to 0.05. The ILs [BMIM][NTf2] can be viewed as associated electrolytes,3 and the polarity of acetonitrile is strong, whereas that of ethyl acetate is weak.11−13 Therefore, the intermolecular forces between acetonitrile and [BMIM][NTf2] is more strong according to the “like-dissolves-like” principle, leading to an increased α12 and a decreased activity of acetonitrile, as shown in Figures 2 and 4. Besides, the effect of [BMIM][NTf2] on separating the ethyl acetate + acetonitrile azeotrope was compared with that of ILs ([BMIM][PF6],11 [EMIM][OTf],12 and [BMIM][OTf]13). These ILs are all salting-out effect for ethyl acetate and saltingin effect for acetonitrile. When the concentration of the ILs in the same level (x3: 0.05, 0.10, 0.15), the equilibrium temperature of the ternary systems ethyl acetate + acetonitrile + ILs as the order: [BMIM][NTf2] > [EMIM][OTf] > [BMIM][OTf] > [BMIM][PF6], as shown in Figure 5. The larger temperature difference is caused by an IL with equal fraction; the lesser amount is needed for breaking the azeotrope. Thus, the system ethyl acetate + acetonitrile + [BMIM][NTf2] needs less energy to eliminate the azeotropy. When the ILs mole fraction is up to 0.05, the azeotropic point could be broken. Comparing the separation effect of the four ILs (x3 = 0.05), these results indicate that the capacities of above ILs extraction separation are [BMIM][NTf2] > [BMIM][PF6] > [BMIM][OTf] > [EMIM][OTf]. That can attribute to the weak polarity of [NTf2]−. Therefore, it can be calculated that the needed amount of [BMIM][NTf2] to remove the azeotrope for ethyl acetate + acetonitrile is 0.027 by e-NRTL model.

values, causing the increase of equilibrium temperature (T), altering the activity coefficients (γi), and even eliminating the azeotropy. Then, the VLE data is also correlated by e-NRTL model. The correlated values show a satisfactory accuracy (δT of 0.2 K) with the measured results. Moreover, the azeotrope of ethyl acetate + acetonitrile can be disappeared when the concentration of [BMIM][NTf2] is up to 0.027 calculated by e-NRTL model. The results obtained in our present work suggest that [BMIM][NTf2] is a good candidate entrainer for separating the ethyl acetate + acetonitrile azeotropic mixture.

■

AUTHOR INFORMATION

Corresponding Author

*Tel.: +86 10 64449695. E-mail: [email protected] or liqs@mail. buct.edu.cn. Notes

The authors declare no competing financial interest.

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REFERENCES

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4. CONCLUSIONS In the study of ionic liquid influence on azeotrope separation, we obtain the VLE data for ethyl acetate (1) + acetonitrile (2)/ethyl acetate (1) + acetonitrile (2) + [BMIM][NTf2] (3) at 101.3 kPa. Thereby, it suggests a distinctly “salting-out effect” of [BMIM][NTf2] for ethyl acetate. Furthermore, the “salting-out effect” of [BMIM][NTf2] results in enhancing the relative volatility (a12) D

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