Isobaric Vapor–Liquid Equilibrium for the Binary Systems of

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Isobaric Vapor−Liquid Equilibrium for the Binary Systems of secButyl Acetate + Methyl Ethyl Ketone, 2‑Methoxyethanol, or 1,2Dimethoxyethane at 101.3 kPa Zhankun Jiang,*,†,‡ Shoutao Ma,† Lei Wang,§ Guoxin Sun,† and Yu Cui*,† †

School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China Key Laboratory of Chemical Sensing & Analysis in Universities of Shandong, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China § School of Chemical Engineering and Technology, Tianjin University, No. 92 Weijin Road, Nankai District, Tianjin 300072, China ‡

ABSTRACT: The isobaric vapor−liquid equilibrium (VLE) data of methyl ethyl ketone (MEK) + sec-butyl acetate (SBAC), 2-methoxyethanol + SBAC, and 1, 2-dimethoxyethane (DME) + SBAC were determined at 101.3 kPa by using an Ellis vapor−liquid equilibrium still. The experimental data passed the thermodynamic consistency test by Herington method and Wisniak test. The VLE values were correlated by the nonrandom two-liquid (NRTL), universal quasichemical activity coefficience (UNIQUAC), and Wilson activity-coefficient models. The results indicated that the three models had good agreement with the experimental data. The 2-methoxyethanol + SBAC system forms a minimum temperature binary azeotrope at 101.3 kPa. The azeotropic temperature is 383.86 K, and the composition of SBAC is 85.1 mol %.

1. INTRODUCTION

to keep them dry. No further purification has been made for the chemicals before use. As additional purity checks, some physical properties of the pure components were measured and compared with reported values. The results are presented in Table 2. The densities were measured at 298.15 K by the pycnometer method. The refractive indexes were measured at 298.15 K with an Abbe refractometer, and the normal boiling points at 101.3 kPa were measured using the Ellis vapor−liquid equilibrium still. 2.2. Analysis. The compositions of the vapor condensate and the liquid phase at equilibrium were analyzed by a gas chromatography (GC, GC-9790, Zhejiang Fu Li Analytical Instrument Co., Ltd.), and calibrated with solutions prepared by gravimetrical standard. TCD was used together with a SE-30 packed column (3 mm × 2 m; Jinan Yuan Bo Chemical Instrument Company, China). High-purity hydrogen (99.999%) was taken as carrier gas at a flow rate of 20 mL min−1. The temperature of injector, oven, and detector were kept at 413.2 K, 373.2 K, and 418.2 K, respectively. The area normalization method was used to gain quantitative results in the GC analysis. The analysis was performed at least two times for each sample. In the process, the standard uncertainty of the measured mole fractions was 0.005. 2.3. Apparatus and Procedure. An Ellis equilibrium still12 was used in the experiments. The structure of the still is shown in Figure 1. The apparatus was validated by measuring the VLE data of ethanol + iso-butanol at 101.3 kPa. The data were

Sec-butyl acetate (SBAC) has high octane number, nontoxic, noncorrosion, and low oxygen content.1 It has got wide application in industry. Methyl ethyl ketone (MEK), 2methoxyethanol, and 1,2-dimethoxyethane (DME) are excellent solvents.2 The mixtures of these solvents, which were generated abundantly in fields such as cellulose material and the printing ink productions, need to be purified for reuse. To our knowledge,3 no vapor liquid equilibrium (VLE) data are available for MEK + SBAC, 2-methoxyethanol + SBAC and DME + SBAC mixtures. The experimental isobaric VLE data of the MEK + SBAC, 2methoxyethanol + SBAC, and DME + SBAC mixtures were measured to meet the need of process design and performance evaluation. The consistency test of the experimental data were carried out with Herington test4 and Wisniak test.5 The VLE data were regressed using Wilson,6 nonrandom two-liquid (NRTL),7 and universal quasichemical (UNIQUAC)8 equations. The three models with their best-fitted binary parameters were applied to correlate the VLE of the binary systems, which were then compared with experimental data.

2. EXPERIMENTAL SECTION 2.1. Chemicals. The chemicals used were SBAC, MEK, 2methoxyethanol, and DME. All of the chemicals were analytical reagents. The source, molecular formula, CAS RN, and mass fraction of the reagents are listed in Table 1, respectively. The mass fraction was measured by a gas chromatograph (GC) equipped with a thermal conductivity detector (TCD). All of the chemicals were stored over activated 4-Å molecular sieves © XXXX American Chemical Society

Received: July 12, 2015 Accepted: December 16, 2015

A

DOI: 10.1021/acs.jced.5b00582 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 1. Materials Description at 101.3 kPaa

a

chemical name

sec-butyl acetate

methyl ethyl ketone

2-methoxyethanol

1,2-dimethoxyethane

isobutanol

ethanol

source molecular formula CASRN initial weight fraction purity purification method final weight fraction purity analysis method

Zhongchuang, China C6H12O2 105-46-4 99.8 dehydration 99.89 GCb

Damao, China C4H8O 78-93-3 99.5 dehydration 99.68 GC

Damao, China C3H8O2 109-86-4 99.5 dehydration 99.74 GC

Damao, China C4H10O2 110-71-4 99.5 dehydration 99.97 GC

Damao, China C4H10O 78-83-1 99.5 dehydration 99.78 GC

Sinopharm, China C2H6O 64-17−5 99.7 dehydration 99.92 GC

u(P) = 0.3 kPa. bGas chromatography.

Table 2. Boiling Points (Tb) at 101.3 kPa, Densities (ρ), and Refractive Index (nD) at 298.15 K of Pure Components Compared with Literature Dataa ρ (kg/m3)

Tb (K) component sec-butyl acetate sethyl ethyl ketone 2-methoxyethanol 1,2-dimethoxyethane a

this work 385.12 352.76 397.48 357.71

literature

this work

b

d

863.8 799.7 960.1 860.4

385.15 352.79b 397.50c 357.75b

nD literature 865.2 799.6d 960.0c 861.3e

this work

literature

1.3872 1.3761 1.4002 1.3780

1.3875b 1.3764b 1.4002b 1.3781b

u(P) = 0.3 kPa, u(Tb) = 0.05 K, u(ρ) = 0.1 kg/m3, u(nD) = 0.0001. bLiterature.9 cLiterature.10 dLiterature.3 eLiterature.11

Table 3. Isobaric VLE Data for Liquid Phase Mole Fraction x and Gas Phase Mole Fraction y for the System Ethanol (1) + Isobutanol (2) at 101.3 kPaa

Figure 1. Ellis still: 1, heater; 2, tube delivering mixture; 3, liquid phase sampling valve; 4, equilibrium temperature thermometer; 5, heater for overheating vapor stream; 6, vapor temperature thermometer; 7, separator for liquid and vapor phases; 8, vapor condenser; 9, cooler; 10, to pressure-stabilizing system; 11, flow meter (drop counter); 12, vapor condensate container; 13, vapor condensate sampling valve; 14, valve for drainage of still.

a

no.

x1

y1

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18

0.000 0.041 0.085 0.136 0.198 0.252 0.302 0.358 0.432 0.525 0.581 0.649 0.711 0.751 0.812 0.889 0.948 1.000

0.000 0.125 0.231 0.341 0.451 0.526 0.584 0.642 0.722 0.787 0.818 0.854 0.885 0.905 0.934 0.966 0.984 1.000

u(P) = 0.3 kPa and u(x1) = u(y1) = 0.005.

reached. Then the equilibrium temperature was recorded and the liquid and vapor samples were collected. The temperatures were measured with a calibrated thermometer graduated in 0.01 K, while the uncertainty of the thermometer is 0.05 K. The pressure of the system was measured by testo-511 digital vacuum gauge with an uncertainty of 0.3 kPa.

compared with those in the literature.13 The results are listed in Table 3 and plotted in Figure 2. It can be seen from Figure 2 that our data agree well with those from the literature. First, a series of solution samples with different concentrations were prepared in advance and separately added to the still slowly. Then, the heating rate was regulated to keep the vapor condensation speed at 60−100 drops per minute. The heater for overheating vapor stream was modulated to make sure that the vapor temperature was equal to or a little higher (less than 0.5 K) than the equilibrium temperature. The system was kept at constant vapor and equilibrium temperatures for at least 60 min, so as to guarantee that the equilibrium state was

3. RESULTS AND DISCUSSION 3.1. Pure Component Vapor Pressures. The vapor pressures of the pure components were calculated using an extended Antoine vapor pressure eq 1, where PS is the saturated vapor pressure (Pa) of pure component and T is the temperature (K). The parameters C1 to C5, which were obtained from ASPEN, are listed in Table 4. B

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Table 5. Experimental VLE Data for Temperature T, Activity Coeffiecient γ, Liquid Phase Mole Fraction x, and Gas Phase Mole Fraction y for the System Methyl Ethyl Ketone (1) + sec-Butyl Acetate (2) at 101.3 kPaa

Figure 2. x1−y1 diagram of ethanol (1)−isobutanol (2) at 101.3 kPa. ■, experimental data; , literature data.13

ln P S = C1 +

C2 + C3 ln T + C4T C5 T

(1)

3.2. Experimental Results. The isobaric VLE experimental data and the corresponding calculated activity coefficients for MEK (1) + SBAC (2), SBAC (1) + 2-methoxyethanol (2), and DME (1) + SBAC (2) at 101.3 kPa are listed in Tables 5−7, respectively. The general equilibrium relationship between the vapor phase and the liquid phase14 can be expressed as follows. S (Vi Pyi φi V = PiSxiγφ e i i

(P − Pi S)/ RT )

x1

y1

0.000 0.090 0.166 0.266 0.321 0.377 0.428 0.470 0.505 0.546 0.591 0.640 0.668 0.705 0.728 0.766 0.800 0.837 0.863 0.888 0.897 0.914 0.934 0.946 1.000

0.000 0.226 0.392 0.513 0.590 0.643 0.684 0.719 0.746 0.779 0.798 0.828 0.847 0.866 0.875 0.894 0.908 0.925 0.938 0.947 0.952 0.959 0.967 0.971 1.000

(2)

1.1563 1.2049 1.0796 1.0934 1.0648 1.0420 1.0358 1.0307 1.0268 1.0111 1.0017 1.0100 1.0046 1.0043 1.0028 0.9995 0.9986 1.0039 0.9996 1.0036 1.0068 1.0055 0.9972 0.9915

the criteria of consistency is that the value of D−J cannot be larger than 10. As to the Wisniak test, the criteria is that the coefficient E is smaller than 3,5 where 1

D = 100·

|∫ ln(γ1/γ2)dx1| 0 1

∫0 |ln(γ1/γ2)|dx1 J = 150·

yP i xiPiS

γ2 0.9937 1.0309 0.9893 1.0006 0.9804 0.9849 0.9990 0.9993 0.9987 0.9850 1.0440 1.0543 1.0475 1.0649 1.1125 1.1215 1.1705 1.2157 1.2234 1.2978 1.3114 1.3484 1.4369 1.5498

a Standard uncertainties u are u(T) = 0.05 K, u(P) = 0.3 kPa, and u(x1) = u(y1) = 0.005.

L

where subscript i is the thermodynamic properties of component i, y is the mole fraction of gas phase, φV is the fugacity coefficient in the mixture vapor phase, x is the mole fraction of liquid phase, γi is the activity coefficient of component i, φs is the fugacity coefficient in the saturate state, VL is the liquid mole volume of pure liquid, P is the total pressure of the equilibrium system, and R is the gas constant. The exponential term in eq 2 is close to unity at 101.3 kPa. After neglected the vapor nonideality and the pressure dependence of the liquid phase fugacity, eq 2 can be simplified to eq 3.

γi =

γ1

T (K) 385.12 378.69 375.12 371.84 369.65 367.97 366.47 365.22 364.22 363.15 361.84 360.71 359.80 358.92 358.19 357.34 356.54 355.69 355.00 354.53 354.23 353.79 353.41 353.40 352.76

(3)

(4)

Tmax − Tmin Tmin

E = 100·

(5)

1

1

1

1

|∫ Lk dx1 − ∫ Wk dx1| 0 0

∫0 Lk dx1 + ∫0 Wk dx1

3.3. Thermodynamic Consistency Tests. In order to confirm the thermodynamic consistency of these experimental data, we verified all experimental data according to the Herington test4 and Wisniak test.5 The Herington test is used to examine the thermodynamic consistency of the VLE data by area test, while the Wisniak test conducts the point-topoint test and area test simultaneously. In the Herington test,

(6)

Lk =

∑ TioxiΔsio/∑ xiΔsio − T

Wk =

RT ⎛ ⎜∑ xi ln γi − ∑ xiΔsio ⎝

∑ xi ln

(7)

yi ⎞ ⎟ xi ⎠

(8)

Table 4. Extended Antoine Equation Coefficients C1-C5 for the Chemicals component

C1

C2

C3

sec-butyl acetate methyl ethyl ketone 2-methoxyethanol 1,2-dimethoxyethane

52.601 72.698 202.63 61.814

−6097.9 −6143.6 −12472 −6102.9

−4.2398 −7.5779 −27.385 −5.6547 C

C4 2.15 5.65 2.64 1.18

× × × ×

10−18 10−06 10−05 10−17

C5 6 2 2 6

T range (K) 174.15 186.48 188.05 215.15

to to to to

561.00 535.50 564.00 536.15

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point of component i; Δsoi is the molar entropy of vaporization of component i; k donates each experimental point. The check results of thermodynamic consistency tests, which are listed in Table 8, passed those tests. The results indicate these binary VLE data are thermodynamically consistent.

Table 6. Experimental VLE Data for Temperature T, Activity Coeffiecient γ, Liquid Phase Mole Fraction x and Gas Phase Mole Fraction y for the System Sec-butyl Acetate (1) + 2methoxyethanol (2) at 101.3 kPaa T (K)

x1

y1

397.48 396.55 393.10 391.18 389.64 388.58 387.61 386.92 386.30 385.97 385.55 385.15 384.84 384.58 384.33 384.08 384.03 383.96 383.86 383.91 383.94 384.12 384.29 385.12

0.000 0.024 0.119 0.191 0.258 0.324 0.379 0.429 0.479 0.509 0.551 0.595 0.636 0.673 0.718 0.735 0.762 0.819 0.851 0.877 0.903 0.939 0.962 1.000

0.000 0.058 0.249 0.354 0.440 0.502 0.546 0.583 0.629 0.651 0.671 0.698 0.715 0.737 0.763 0.773 0.790 0.824 0.849 0.865 0.884 0.914 0.941 1.000

γ1 1.7199 1.6431 1.5387 1.4796 1.3882 1.3302 1.2786 1.2582 1.2376 1.1951 1.1638 1.1263 1.1060 1.0817 1.0786 1.0648 1.0355 1.0301 1.0162 1.0083 0.9977 0.9969 0.9937

γ2 1.0060 0.9994 0.9840 0.9802 0.9740 0.9836 1.0069 1.0304 1.0257 1.0353 1.0808 1.1159 1.1841 1.2258 1.2917 1.3275 1.3701 1.5142 1.5823 1.7172 1.8620 2.1657 2.3895

Table 8. Thermodynamic Consistency Check

a

x1

y1 0.000 0.154 0.293 0.408 0.487 0.560 0.606 0.650 0.692 0.707 0.727 0.755 0.808 0.852 0.891 0.925 0.955 0.986 1.000

γ1 1.1333 1.0427 1.0143 1.0005 0.9893 0.9752 0.9734 0.9658 0.9758 0.9553 0.9711 0.9689 0.9681 0.9670 0.9632 0.9560 0.9544 0.9965

D−J

L

W

E

−5.54

3.39

3.59

2.87

14.01

4.81

9.20

3.97

4.14

2.17

20.20

11.49

8.71

1.87

1.95

2.09

⎡⎛ exp 2 ⎛ Piexp − Piest ⎞2 Ti − Tiest ⎞ ⎢ Q=∑ ⎜ ⎟ +⎜ ⎟ ⎢ σT σP ⎠ ⎝ ⎠ i = 1 ⎣⎝ 2 ⎛ xiexp − x iest ⎞2 ⎛ yiexp − yiest ⎞ ⎤ ⎟⎟ ⎥ +⎜ ⎟ + ⎜⎜ σx σ ⎝ ⎠ ⎝ ⎠ ⎥⎦ y

Table 7. Experimental VLE Data for Temperature T, Activity Coefficient γ, Liquid Phase Mole Fraction x, and Gas Phase Mole Fraction y for the System 1,2-Dimethoxyethane (1) + sec-Butyl Acetate (2) at 101.3 kPaa 0.000 0.066 0.146 0.223 0.284 0.347 0.394 0.439 0.490 0.509 0.538 0.571 0.646 0.715 0.783 0.850 0.911 0.972 1.000

J 13.76

n

Standard uncertainties u are u(T) = 0.05 K, u(P) = 0.3 kPa, and u(x1) = u(y1) = 0.005.

T (K)

D 8.22

3.4. Data Regression. The experimental data of three binary systems were regressed according to the NRTL, UNIQUAC, and Wilson models with Aspen software. The Maximum likelihood objective function was used for the regression. Maximum likelihood is a generalization of the leastsquares method. In the maximum likelihood objective function, errors in T, P, x, and y are considered. The objective function is minimized by manipulating the physical property parameters identified in the regression case and manipulating the estimated value corresponding to each measurement. The function is presented in eq 9.

a

385.12 381.76 379.45 377.02 375.28 373.55 372.42 371.13 369.84 368.97 368.73 367.46 365.74 364.15 362.74 361.41 360.48 359.50 357.71

system methyl ethyl ketone + sec-butyl acetate 2-methoxyethanol + sec-butyl acetate 1,2-dimethoxyethane + sec-butyl acetate

(9)

where n is the number of experimental points, T is the equilibrium temperature, superscript exp. and est. are abbreviation of experiment and estimate, respectively, σ is the standard deviation of the indicated data, and Q is the objective function to be minimized by data regression. The correlated binary interaction parameters from experimental data are stated in Table 9, combined with the rootmean-square deviations (RMSD) in vapor phase mole fraction and temperature. It is observed that the RMSD of temperature for the activity models are less than 0.63 and those of vapor phase composition are no more than 0.018. The calculated values of the vapor phase composition and temperature by these three models show reasonably good agreement with the experimental values. The azeotropic temperature and composition of SBAC + 2methoxyethanol at 101.3 kPa here are 383.86 K, 85.1 mol % SBAC. The experimental T−x−y diagrams of binary systems MEK + SBAC, SBAC + 2-methoxyethanol, and DME + SBAC, together with correlated curves with UNIQUAC, UNIQUAC, or NRTL model, are shown in Figure 3, Figure 4, and Figure 5, respectively.

γ2 0.9937 0.9973 0.9787 0.9731 0.9676 0.9613 0.9621 0.9654 0.9738 0.9889 0.9887 0.9973 1.0021 1.0168 1.0273 1.0804 1.1230 1.1497

4. CONCLUSIONS Isobaric VLE values were determined experimentally for MEK + SBAC, SBAC + 2-methoxyethanol, and DME + SBAC systems with Ellis equilibrium still at 101.3 kPa. The results show that SBAC + 2-methoxyethanol system forms a minimum temperature azeotrope, and the other two systems do not form

u(T) = 0.05 K, u(P) = 0.3 kPa, and u(x1) = u(y1) = 0.005.

Tmax and Tmin (K) are the maximum and the minimum boiling points of the system, respectively; Toi represents the boiling D

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Table 9. Correlation Parameters and Root Mean Square Deviations for the Binary Systems correlation parametersa system methyl ethyl ketone (1) + sec-butyl acetate (2)

sec-butyl acetate (1) + 2-methoxyethanol (2)

1,2-dimethoxyethane (1) + sec-butyl acetate (2)

ajic

bij

bji

σy1d

σTe

−5.6649 2.2980 −0.1883 −4.6877 3.0193 −5.1638 −7.6852 3.2430 −5.5647

4.5668 −2.3811 2.8340 8.5541 −2.8736 −1.6461 12.3747 −5.0218 3.9500

1877.4487 −697.4681 94.8668 2540.8531 −1632.6304 2138.7127 2398.6011 −950.4824 1362.6158

−1343.5545 655.8358 −1135.9585 −3581.3473 1341.9977 51.4284 −3841.9444 1465.9673 −1127.8345

0.010 0.010 0.008 0.009 0.008 0.010 0.017 0.018 0.016

0.51 0.51 0.58 0.22 0.22 0.23 0.56 0.59 0.63

models f

NRTL UNIQUAC Wilson NRTL UNIQUAC Wilson NRTL UNIQUAC Wilson

RMSD

aijb

a

a,b parameters of the NRTL, UNIQUAC, or Wilson model. bSubscripts ij represents the pair interaction. cSubscripts ji represents the pair exp 2 n est exp 2 1/2 e 1/2 f interaction. dσy1 = (∑ni=1((yest 1,i − y1,i ) /n)) . σT = (∑i=1((Ti − Ti ) /n)) . The value of αij was fixed at 0.3 for the three binary systems as these systems belong to type I according to the definition in the literature.7

Figure 5. Experimental data and calculated data for the system of 1,2dimethoxyethane (1) + sec-butyl acetate (2) at 101.3 kPa. ■, experimental x1; △, experimental y1; ---, calculated x1 with NRTL model; , calculated y1 with NRTL model.

Figure 3. Experimental data and calculated data for the system of methyl ethyl ketone (1) + sec-butyl acetate (2) at 101.3 kPa. ■, experimental x1; △, experimental y1; ---, calculated x1 with UNIQUAC model; , calculated y1 with UNIQUAC model.

method. The VLE values were correlated by the NRTL, UNIQUAC, and Wilson activity-coefficient models. The corresponding binary interaction parameters of the models were obtained by maximum likelihood method. The RMSD of temperature for the three activity models are less than 0.63, and those of vapor phase composition are no more than 0.018. For the SBAC + 2-methoxyethanol system, the azeotropic temperature is 383.86 K, and the composition of SBAC is 85.1 mol % at 101.3 kPa.

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AUTHOR INFORMATION

Corresponding Authors

*Tel.: +86 15053121073. E-mail address: chm_jiangzk@ujn. edu.cn (Z. Jiang). *Tel.: +86 053182767937. E-mail address: [email protected]. cn (Y. Cui).

Figure 4. Experimental data and calculated data for the system of secbutyl acetate (1) + 2-methoxyethanol (2) at 101.3 kPa. ■, experimental x1; △, experimental y1; ---, calculated x1 with UNIQUAC model; , calculated y1 with UNIQUAC model.

Funding

We thank the outstanding young scientist award fund in Shandong Province (BS2014NJ020) and Science and technology developing program of universities in Shandong Province (J14LC06) for the financial support.

an azeotrope. Thermodynamic consistency of the experimental data was verified according to Herington test and Wisniak

Notes

The authors declare no competing financial interest. E

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REFERENCES

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F

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