Vapor–Liquid Equilibrium Data for Binary Systems of N,N

Oct 19, 2015 - Department of Thermal Science and Energy Engineering, School of Mechanical Engineering, University of Science and Technology Beijing, B...
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Vapor−Liquid Equilibrium Data for Binary Systems of N,N-Dimethylacetamide with Cyclohexene, Cyclohexane, and Benzene Separately at Atmospheric Pressure Wanliang Mi,*,† Ruixin Tong,† Chao Hua,‡ Kai Yue,† Debiao Jia,‡ Ping Lu,‡ and Fang Bai‡ †

Department of Thermal Science and Energy Engineering, School of Mechanical Engineering, University of Science and Technology Beijing, Beijing 100083, China ‡ Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China ABSTRACT: The reaction for hydrogenation of benzene has been paid much attention as the demand for synthesis of nylon rapid developa. Usually, byproducts of cyclohexane and unreacted benzene unavoidably exist in the production of cyclohexene through the hydrogenation of benzene route. To obtain cyclohexene with high purity, extractive distillation is used to separate cyclohexene mixture. However, the process simulation for extractive distillation is necessary for industry design and production, which requires the relevant vapor−liquid equilibrium (VLE) data to simulate accurately. The VLE data for the binary systems of extractant N,N-dimethylacetamide (DMAC) with cyclohexene, cyclohexane, and benzene at atmospheric pressure was measured using a PH-I-type VLE kettle. In addition, a thermodynamic consistency check has been done on the obtained data, indicating that the experimental data satisfy the examination of the thermodynamic consistencies. Moreover, the results are significantly close when NRTL and Wilson equations are used to correlate with data. The maximum deviation for the average vapor composition and the average temperature composition are 0.0095 K and 1.12 K, respectively, which is satisfactory for the separation engineering design requirement. The results could provide basic data for practical application. for DMAC with HE, HA, and BZ are first reported in a wide temperature range in this paper. The VLE data is the basis for computational simulation calculation, which has direct influence on the accuracy of the simulation results.8 Usually, relatively higher theoretical plates were used in the design of the DMAC extractive distillation tower in China to guarantee safety, which leads to increased energy consumption and equipment investment. Besides, operation parameters such as the feed position of

1. INTRODUCTION With the increasing demand for nylon-66 and nylon-6 in recent years, the production of their source materials, cyclohexanone and cyclohexanol, has attracted many researchers. Among the production techniques, the production of cyclohexene through the hydrogenation of benzene route has received growing attention because of its high conversion rate, pretty good atom economy, and low emission, which at the same time made it the major technique for the production of cyclohexanone in recent years. However, during the production process, there are byproducts: cyclohexane and unreacted benzene. Moreover, the boiling points for cyclohexene (HE), cyclohexane (HA), and benzene (BZ) are quite similar, which makes it easy to form a near-azeotropic system and makes the process of separation difficult. DMAC is a promising solvent for separating the nearazeotrope system for HE−HA−BZ, which presents fine solubility, good thermo stability, low toxicity, and low corrosiveness. The common method for the separation is DMAC extractive distillation, which is attracting growing attention from the public.1−5 The boiling point for DMAC is 166.1 °C, which is rather different from those of cyclohexene, cyclohexane, and benzene. Usually, it is difficult to obtain their vapor−liquid equilibrium (VLE) data. A few works have reported some VLE data of DMAC with HE, HA, and BZ under some specific conditions, but the data is not sufficient for the actual demand of chemical engineering calculation and simulation.6,7 The binary VLE data © XXXX American Chemical Society

Table 1. Mass Fraction Purities and Sources of Chemical Samples chemical name cyclohexene cyclohexane benzene N,Ndimethylacetamide

source Sinopharm Chemical Reagent Co., Ltd. Engineering and Technology Research Center of Guangdong Fine Chemistry Beijing Chemical Factory Sinopharm Chemical Reagent Co., Ltd.

mass fraction puritya

analysis methodb

0.99

GC

0.99

GC

0.995 0.98

GC GC

a No additional purification is carried out for all samples. bGC: gas chromatography.

Received: October 16, 2014 Accepted: August 7, 2015

A

DOI: 10.1021/acs.jced.5b00011 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 2. Basic Properties of the Reagentsa

a

materials

A

B

C

range (°C)

cyclohexene cyclohexane benzene N,N-dimethylacetamide

6.88617 7.09926 7.20090 10.50

1229.97 1380.54 1415.80 2412

224.100 246.526 248.028 273.20

79 to 280 80 to 250

Table 4. Results of the Thermodynamic Consistency Check for All Binary Systems system

I



D

J

D−J

HE + DMAC HA + DMAC BZ + DMAC

0.1007 0.0915 0.0726

0.2698 0.2962 0.2226

37.32 30.79 32.62

34.88 36.06 36.60

2.44 −5.27 −3.98

Antoine equation:10 log p = A − (B/T + C); p (mmHg) and T (°C).

Basic properties of the reagents are shown in Table 2.9 A, B, and C are Antoine coefficients. The equation for saturation vapor pressure is shown in section 3.1. 2.2. Experimental Apparatus. A PH-I type VLE kettle is used to test VLE data in the experiment. Its structure map is shown in Figure 1. Thermal resistance was chosen to measure the temperature of equilibrium kettle; its accuracy is ± 0.1°C. A gas chromatograph (GC-SP3420, Beijing Beifen Ruili Analysis Instrument, Ltd.) with column KB-5 (0.25 μm × 0.32 mm × 30 m) was used to detect the sample content. 2.3. Experimental Method. A 30 mL aliquot of the liquid mixture is injected into the equilibrium kettle. Then, we turn on cooling water and gradually heat the mixture at the beginning stage. The heating power is adjusted until a condensation return rate of 2−3 drops per seconds is achieved. After running for 0.5 h to maintain stabilization of the reflux, we read the temperature every 5 min. When the temperature is stable (in about 0.5 h), we think it indicates that the liquid and vapor phases have achieved equilibrium. Then, a 0.6 μL sample of the liquid phase and vapor phase was taken out for content test in chromatography. Each group test was repeated for three times in order to reduce the test error for samples. Because the outlet of condenser shown in sketch map is connected with outside ambient atmosphere, the pressure in the VLE experiment is kept at atmospheric pressure. 2.4. Analysis Method. The sample is analyzed by chromatography with an FID detector using programmed temperature method. Initial column temperature is kept at 50 °C for 1 min. Then, it is heated up to 220 °C at a 10 °C·min−1 heating rate and kept for 10 min. The gasification chamber temperature is 220 °C, and the temperature of the detector is 250 °C, using high purity N2 as carrier gas with flow rate of 30 mL·min−1. Hydrogen and air flow rates are 30 mL·min−1 and 300 mL·min−1, respectively. 2.5. Validity Check of Experimental Apparatus. Benzene−toluene VLE experiment was carried out in this experimental device to verify the validity of apparatus. The obtained data was compared with the literature values11 shown in Figure 2. The results show good consistency with the literature. Area verification method is widely used for the VLE data check,12 which is also employed for thermodynamic consistency check in this study, as shown in Table 3. It shows that the result of |D − J| is less than 10, which indicates thermodynamic consistency; therefore, the experimental apparatus can be used to measure the VLE data properly. In Table 3, T1 is the boiling point temperature of low-boilingpoint components. T2 refers to the boiling point temperature of high-boiling-point substances of two components.

Figure 1. Sketch map for PH-I VLE equipment: 1, heating rod; 2, thermometer sleeve tube; 3, liquid phase sample connection; 4, glass VLE kettle; 5, thermal resistance; 6, condenser; and 7, vapor phase sample connection

Figure 2. Comparison between experimental and literature data of VLE for benzene−toluene binary system.

raw material, the reflux ratio, and the solvent ratio are usually not optimal because of the absence of accuracy in VLE data. To solve those problems, the binary VLE data of DMAC with HE, HA, and BZ should be tested in a wide temperature range so that their binary interaction parameters could be obtained, which is beneficial for the design and operation optimization of DMAC extractive distillation method.

2. EXPERIMENT 2.1. Experimental Reagent. In this paper, all the chemicals were obtained from China without further treatment. Table 1 gives description of the chemicals. Table 3. Thermodynamic Consistency Test for VLE T1

T2

Tmin

ΔTmax

K

K

K

K

I



D

J

D−J

353.25

383.75

353.25

30.50

0.0024

0.0589

4.07

12.95

−8.88

B

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Table 5. VLE Data of HE−DMAC Binary System at 101.33 kPa with Uncertainty of u(T) = 0.05 K, u(x) = u(y) = 0.006, u(P) = 0.1 kPa T no. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 average

mole fraction

NRTL

Wilson

K

x1

y1

Δy1

ΔT

Δy1

ΔT

439.25 416.95 409.95 397.25 387.25 376.95 373.25 369.45 367.25 365.15 363.25 361.85 360.15 358.95 357.65 356.15

0 0.0795 0.1443 0.2116 0.2854 0.4982 0.5400 0.6152 0.6602 0.6714 0.7238 0.8447 0.8744 0.9130 0.9502 1.0

0 0.5385 0.6612 0.7794 0.8511 0.9309 0.9399 0.9587 0.9632 0.9704 0.9740 0.9803 0.9865 0.9893 0.9939 1.0

0.0096 0.0416 0.0208 0.0073 0.0019 0.0071 0.0070 0.0011 0.0030 0.0027 0.0001 0.0062 0.0027 0.0033 0.0027 0.0000 0.0073

0.30 1.95 3.01 0.25 2.31 2.32 0.72 0.29 0.10 1.76 1.73 0.92 0.16 0.16 0.30 0.02 1.02

0.0095 0.0416 0.0207 0.0072 0.0018 0.0071 0.0070 0.0011 0.0030 0.0027 0.0001 0.0062 0.0026 0.0033 0.0027 0.0000 0.0073

0.30 1.95 3.01 0.26 2.32 2.32 0.73 0.30 0.08 1.75 1.71 0.93 0.17 0.16 0.31 0.02 1.02

γ1 1.4745 1.1582 1.2395 1.2764 1.0405 1.0696 1.0622 1.0571 1.1110 1.0919 0.9804 1.0016 0.9964 0.9996 1.0000

γ2 1.0000 0.9790 0.9704 1.0577 1.1299 1.1044 1.2132 1.1604 1.2815 1.1636 1.3173 1.8856 1.7091 2.0583 2.1669

Table 6. VLE Data of HA−DMAC Binary System at 101.33 kPa with Uncertainty of u(T) = 0.05 K, u(x) = u(y) = 0.006, u(P)= 0.1 kPa T no. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 average

mole fraction

NRTL

Wilson

K

x1

y1

Δy1

ΔT

Δy1

ΔT

439.25 415.15 405.35 389.45 376.25 369.45 367.35 365.55 361.25 360.35 359.45 358.45 357.55 356.45 355.35 353.85

0 0.1049 0.1522 0.2376 0.3716 0.4769 0.4927 0.5565 0.6784 0.7106 0.7741 0.8346 0.8569 0.8982 0.9404 1.0

0 0.5863 0.6901 0.8230 0.9059 0.9383 0.9427 0.9544 0.9651 0.9696 0.9768 0.9768 0.9813 0.9840 0.9867 1.0

0.0096 0.0147 0.0283 0.0145 0.0148 0.0125 0.0112 0.0099 0.0118 0.0097 0.0064 0.0095 0.0062 0.0057 0.0060 0.0002 0.0107

0.30 2.52 1.50 1.87 1.22 0.44 1.59 0.02 0.42 0.45 1.09 1.27 0.77 0.39 0.07 0.04 0.87

0.0095 0.0266 0.0355 0.0152 0.0115 0.0091 0.0079 0.0072 0.0107 0.0090 0.0064 0.0101 0.0069 0.0065 0.0064 0.0003 0.0112

0.30 3.51 2.39 1.45 1.60 1.21 2.39 0.86 0.15 0.01 0.94 1.37 0.93 0.60 0.24 0.04 1.12

γ1 1.2084 1.2113 1.3368 1.3097 1.2659 1.3035 1.2277 1.1489 1.1305 1.0727 1.0240 1.0284 1.0158 1.0048 1.0000

γ2 1.0000 0.9560 1.0450 1.1613 1.2355 1.2772 1.3311 1.3063 1.6499 1.6602 1.6888 2.4074 2.3345 2.9487 4.4008

Table 7. VLE Data of BZ−DMAC Binary System at 101.33 kPa with Uncertainty of u(T) = 0.05 K, u(x) = u(y) = 0.006, u(P)= 0.1 kPa T no. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 average

mole fraction

NRTL

Wilson

K

x1

y1

Δy1

ΔT

Δy1

ΔT

439.25 422.65 417.45 407.85 402.95 391.15 389.25 382.35 378.95 375.95 369.75 365.65 363.25 361.55 357.65 355.15 353.25

0 0.0537 0.0780 0.1229 0.1463 0.2182 0.2461 0.2991 0.3341 0.3701 0.5237 0.5687 0.6244 0.7286 0.7978 0.9254 1.00

0 0.4051 0.5237 0.6504 0.7016 0.8059 0.8328 0.8822 0.8993 0.9154 0.9486 0.9585 0.9656 0.9746 0.9823 0.9938 1.00

0.0096 0.0152 0.0100 0.0248 0.0242 0.0208 0.0190 0.0051 0.0052 0.0033 0.0069 0.0037 0.0032 0.0040 0.0016 0.0005 0.0014 0.0093

0.30 0.08 0.96 0.91 0.24 0.91 0.56 0.80 1.06 1.19 1.88 0.19 0.38 1.37 0.59 0.24 0.40 0.71

0.0095 0.0178 0.0123 0.0262 0.0251 0.0205 0.0184 0.0041 0.0042 0.0023 0.0064 0.0033 0.0030 0.0041 0.0018 0.0005 0.0015 0.0095

0.30 0.22 1.13 1.06 0.37 0.89 0.53 0.90 1.20 1.36 1.72 0.31 0.44 1.41 0.50 0.29 0.40 0.77

C

γ1 1.3144 1.3050 1.2666 1.2822 1.3042 1.2520 1.2972 1.2921 1.2848 1.1119 1.1596 1.1388 1.0341 1.0664 1.0019 1.0000

γ2 1.0000 1.0257 0.9927 1.0476 1.0840 1.1673 1.1171 1.0949 1.1226 1.1204 1.1539 1.2187 1.2801 1.4073 1.5574 1.6398

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3. RESULTS AND ANALYSIS 3.1. Result for the Vapor−Liquid Equilibrium. The VLE data for HE−DMAC, HA−DMAC, and BZ−DMAC at atmospheric pressure are presented in Tables 5, 6, and 7, respectively. At atmospheric pressure, vapor phase could be regarded as the ideal gas. The liquid−vapor relation equation could be as follows: s yp = xirp i i i

where ri is the liquid activity coefficient and psi is saturated vapor pressure obtained by the Antoine equation. According to the Antoine equation and the above VLE equation, the activity coefficient of the corresponding liquid phase is calculated. The results for the three groups are listed in Tables 5 to 7, respectively. 3.2. Consistency Check of Vapor−Liquid Equilibrium Data. Thermodynamic consistency check is to apply the general relations of thermodynamics to verify the reliability of the experimental data. In this research, we used area check with Gibbs− Duhem equation to verify the thermodynamic consistency of obtained data; the procedure is as follows: Plotting ln(γ1/γ2) − x1, the result is shown in Figure 3. Let I = ∫ 10 ln(γ1/γ2) dx1 and ∑ = ∫ 10|ln(γ1/γ2) dx1|, Then |ΔTmax| I × 100, J = 150 × ∑ Tmin

D=

In the above formula, the value of 150 is the empirical value obtained by Herington through the analysis on the blended heat of typical organic solvent.13 ΔTmax is the difference of the boiling points of two components. If azeotropes are formed and if the azeotropes have the lowest azeotropic temperature, then this value is the difference between the minimum azeotropic temperature and the higher boiling point of any components. If the azeotropes have the highest azeotropic temperature, then this value is the difference between the highest azeotropic temperature and the lower boiling point of any components. When |D − J| < 10, the experimental data are considered to be qualified for the thermodynamic consistency check.14 The results for the thermodynamic consistency check are shown in Table 4. Table 4 shows that the values of |D − J| are less than 10 for our studied materials instead of D − J < 10 in this study, not as Wisniak declared.15,16 Also, for our binary systems, ΔHa/ΔGEm ≤ 3; thus, it avoids the deviation of Herington simplification,17 overcoming the issues raised by Wisniak. The thermodynamic consistency test is reliable. The experimental data is satisfactory according to the thermodynamic consistency check. 3.3. Correlation of the Experimental Data. Activity coefficient in liquid phase is correlated with NRTL18,19 and Wilson.20 Objective function for regression calculation is shown as follows: F=

1 n

n

∑ [|Zcal − Zexp|i2 + |Tcal − Texp|i2 /100]

Figure 3. Diagram of x1 − ln(r1/r2) for (a) HE−DMAC, (b) HA− DMAC, (c) BZ−DMAC separately.

i=1

where Z is the gas molar concentration, T is equilibrium temperature in K, n is amount of measurement number, and the subscripts cal and exp represent the experimental and calculated values, respectively. In the NRTL equation, αij = 0.3. In the Wilson equation, (λ12 − λ11) and (λ21 − λ22) are binary system constants. In a narrow temperature range, they are considered to be independent of temperature. The results are presented in Tables 5 to 7 and Figure 4. In Tables 5 to 7,

Δy =

1 n

⎛ |y − y |⎞ 1 ∑ ⎜⎜ 1_cal 1 ⎟⎟ , ΔT = y n ⎠i i ⎝ 1 n

n

∑ (Tcal − Texp)i i

Tables 5 to 7 show that the average equilibrium temperature deviation of VLE in the HE−DMAC system for the two simulated correlations is 1.02 K. The average deviations of vapor D

DOI: 10.1021/acs.jced.5b00011 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Figure 4. Equilibrium temperature and composition for three sets of binary systems.

vapor phase, they are 0.0087 and 0.0091, respectively. The data is very close. These data show that we could correlate the above measured data of HE−DMAC, HA−DMAC, and BZ−DMAC systems by both NRTL and Wilson equation. All errors are quite small, which meets with engineering design requirements of separation. The relevant interaction parameters for three sets of data are illustrated in Table 8. The experimental data from the literature6 is compared graphically with this work’s data for the HA−DMAC binary system, as shown in Figure 5. Because the experiments were done at different pressure, the light component in liquid phase at relatively high pressure has higher content than those done at low pressure at the same temperature. Furthermore, at high temperature, the content difference in liquid is more significant.

Table 8. Parameters of Wilson and NRTL for Three Sets of Systems Wilson equation parameters

NRTL equation parameters

(λ12 − λ11)

(λ21 − λ22)

(g12 − g22)

(g21 − g11)

system

J·mol−1

J·mol−1

J·mol−1

J·mol−1

α12

HE−DMAC HA−DMAC BZ−DMAC

−259.5 −1893.0 −1216.1

1658.0 7649.1 4050.5

2172.4 8159.7 5080.9

−745.4 −3065.5 −2158.1

0.3 0.3 0.3

phase for both NRTL and Wilson equation are 0.0073. The average deviations of temperature for HA−DMAC systems are 0.87 K and 1.12 K for two equations, respectively, whereas for E

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(6) Prasad, T. E. V.; Kumar, S. S.; Goud, M. B. P.; et al. Bubble Temperature Measurements on Binary Mixtures Formed by Cyclohexane at 94.7 kPa. J. Chem. Eng. Data 2003, 48, 351−353. (7) Möllmann, C.; Gmehling, J. Measurement of Activity Coefficients at Infinite Dilution Using Gas-liquid Chromatography. 5. Results for NMethylacetamide, N,N-Dimethylacetamide, N,N-Dibutylformamide, and Sulfolane as Stationary Phases. J. Chem. Eng. Data 1997, 42, 35−40. (8) Chen, Z.; Gu, F.; Hu, W. Chemical Engineering Thermodynamics; Chemical Industry Press: Beijing, 2000; pp 177−179. (9) John, A. Lange’s Handbook of Chemistry, 2nd ed.; Science Press: Beijing, 2003; pp 237−240. (10) Poling, B. E.; Prausnitz, J. M.; O’Connell, J. P. The Properties of Gases and Liquids, 5th ed.; McGraw Hill Professional: New York, 2000. (11) Chen, M.; Cong, D.; Fang, T.; Qi, M. Chemical Engineering Principle. Chemical Industry Press: Beijing, 2006; pp 268−269. (12) Xiong, J.; Zhang, L. Binary Isobaric Vapor-liquid Equilibrium of N-formylmorpholine with Benzene. Chin. J. Chem. Eng. 2007, 58 (5), 1986−1090. (13) Herington, E. F. G. Tests for the Consistency of Experimental Isobaric Vapour-liquid Equilibrium Data. J. Inst. Pet. 1961, 37, 457−470. (14) Chen, Z.; Gu, F.; Hu, W. Chemical Engineering Thermodynamics. Chemical Industry Press: Beijing, 2000; pp 177−179. (15) Wisniak, J.; Pérez-Correa, J. R.; Mejía, A.; Segura, H. Comments on “Experimental Measurements of Vapor−Liquid Equilibrium Data for the Binary Systems of Methanol + 2-Butyl Acetate, 2-Butyl Alcohol + 2Butyl Acetate, and Methyl Acetate + 2-Butyl Acetate at 101.33 kPa. J. Chem. Eng. Data 2013, 58, 3563−3566. (16) Wisniak, J.; Pérez-Correa, J. R.; Mejía, A.; Segura, H. Correction to “Comments on ′Experimental Measurements of Vapor− Liquid Equilibrium Data for the Binary Systems of Methanol + 2-Butyl Acetate, 2-Butyl Alcohol + 2-Butyl Acetate, and Methyl Acetate + 2-Butyl Acetate at 101.33 kPa′. J. Chem. Eng. Data 2014, 59, 942. (17) Wisniak, J. The Herington Test for Thermodynamic Consistency. Ind. Eng. Chem. Res. 1994, 33, 177−180. (18) Vetere, A. The NRTL Equation as a Predictive Tool for VaporLiquid Equilibria. Fluid Phase Equilib. 2004, 218, 33−39. (19) Renon, H.; Prausnitz, J. M. Local Compositions in Thermodynamic Excess Functions for Liquid Mixtures. AIChE J. 1968, 14 (1), 135−144. (20) Wilson, G. Vapor-liquid equilibrium. XI. A New Expression for the Excess Free Energy of Mixing. J. Am. Chem. Soc. 1964, 86, 127−130.

Figure 5. Comparison of equilibrium data of HA−DMAC with ref 6 at different pressure.

Prasad et al.6 has reported that experimental error is 0.0001 in the liquid-phase mole fraction. The average absolute deviation in x1 in this work is 0.002, which is within an average absolute deviation of 0.5 %.

4. RESULTS The vapor−liquid equilibrium data of HE−DMAC, HA− DMAC, and BZ−DMAC are measured at atmospheric pressure using PH-I-type vapor−liquid equilibrium kettle, which is qualified with thermodynamic consistency. The experimental vapor−liquid equilibrium data was successfully correlated with both the Wilson and the NRTL activity coefficient models. The errors are small, which satisfied the engineering separation design requirement. The three sets of vapor−liquid equilibrium data at atmospheric pressure for the binary systems provide basic data for computational simulation, so as to make optimization more accurate. In this way, more reasonable parameters like reflux ratio and solvent ratio are obtained, which provides further guidance for actual production.



AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Funding

National Natural Science Foundation of China (no. 21006005) and the Fundamental Research Funds for the Central Universities (no. FRF-TP-14-025A2). Notes

The authors declare no competing financial interest.



REFERENCES

(1) Malanowski, S. Experimental Methods for Vapor-liquid Equilibria. Part I. Circulation methods. Fluid Phase Equilib. 1982, 8, 197−219. (2) Gmehling, J.; Onken, U.; Arlt, W. Vapor-Liquid Equilibrium Data Collection; Chemistry Data Series: Scholium International: Frankfurt, 1977 to 1984. (3) Rogalski, M.; Mączyńska, Z.; Mączyński, A. Verified Vapor Liquid Equilibrium Data; PWN PWN-Polish Scientific Publishers: Warszawa, Poland, 1977. (4) Ohe, S.Salt Effect. In Vapor-Liquid Equilibrium Data; Physical Sciences Data Series, Vol. 42; Elsevier: New York, 1991; pp 1708 (5) Wichterle, I.; Linek, J.; Hala, E. Vapor-Liquid Equilibrium Data Bibliography; Elsevier: New York, 1973. F

DOI: 10.1021/acs.jced.5b00011 J. Chem. Eng. Data XXXX, XXX, XXX−XXX