Article Cite This: J. Chem. Eng. Data 2018, 63, 395−401
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Isobaric Vapor−Liquid Equilibrium Data for Two Binary Systems n‑Hexane + 1,2-Dimethoxyethane and Methylcyclopentane + 1,2Dimethoxyethane at 101.3 kPa Yinhai Sun, Dianliang Fu, Shoutao Ma, Zhanhua Ma, and Lanyi Sun* State Key Laboratory of Heavy Oil Processing, College of Chemical Engineering, China University of Petroleum (East China), Qingdao, Shandong 266580, China ABSTRACT: Isobaric vapor−liquid equilibrium (VLE) data for binary systems of nhexane + 1,2-dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane were measured at 101.3 kPa with an Ellis vapor−liquid equilibrium still, and the thermodynamic consistency of the experimental data was checked and passed by the Herington method and Wisniak test. The VLE values were correlated with the nonrandom two-liquid, universal quasichemical and Wilson activity coefficient models, and the corresponding binary interaction parameters of the three models were obtained. The results correlated with three models have good agreement with the experimental data, indicating that the three models were all fitted well.
1. INTRODUCTION Reformed raffinate oil with high content of n-hexane, methylcyclopentane, and other saturated hydrocarbons is the byproduct which is produced from aromatics extraction of catalytic reforming and used to produce high quality, high value-added fine chemical raw materials.1 Methylcyclopentane can be used as organic synthesis solvent and gas chromatography standard solution.2 n-Hexane is an important organic solvent and widely used in the fields of fine chemicals, medicine industry, and so on. High concentration n-hexane (more than 90 wt %) is mainly used as a chemical reagent, liquid chromatography standard solution, etc.3−5 1,2-Dimethoxyethane, which is widely used in the chemical industry and the synthesis of pharmaceutical extractive and organic intermediates, is an excellent nonproton polar solvent. Considering the wide application of the three substances, it is imperative to separate the two mixtures of n-hexane + 1,2-dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane. The vapor− liquid equilibrium (VLE) data of these two systems are required for the foundation of the separation. However, no experimental data of n-hexane + 1,2-dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane in the data archive of the NIST Thermodynamics Research Center has been found. Therefore, isobaric vapor−liquid equilibrium data of two binary systems at 101.3 kPa are considered in this study. The VLE data passed the thermodynamic consistency tests with the Herington test6 and Wisniak test.7 The experimental data of the two binary systems correlated with nonrandom two-liquid (NRTL),8 universal quasichemical (UNIQUAC),9 and Wilson10 activity coefficient equations, and the results of root mean square deviations (RMSD) show that the experimental values are reliable. The discussion of the relative volatilities has been added to data analysis. © 2018 American Chemical Society
2. EXPERIMENTAL SECTION 2.1. Experimental Reagents. n-Hexane, methylcyclopentane, and 1,2-dimethoxyethane were used, and the information of the three chemicals is listed in Table 1. All samples used in the measurements were checked by gas chromatography (GC, GC9790II, Zhejiang Fu Li Analytical Instrument Co. Ltd.), and the Karl Fischer titration technique was used to measure the water content. No appreciable peak of impurity was detected. Dehydration and distillation were the two methods used to purify the reagents. Dehydration is the process of removing water from a product using 4 Å molecular sieve. Distillation is a physical separation process to remove some little impurity from the reagents that the GC cannot test. The packing of the distillation experiment is θ1.6 triangular spiral packing, and its height is 1.5 m. Improving the purity of the reagents with these two methods ensures the accuracy of the experiment. 2.2. Sample Analysis. Gas chromatography (GC) was used to analyze the composition of the liquid phase and vapor condensate. FID was used together with a PEG-20 M chromatographic column (30 m × 0.32 mm × 0.33 μm). High purity hydrogen was used as the carrier gas at a constant flow rate of 20 mL/min. The temperatures of vaporizer and detector were 373.15 and 373.15 K, respectively. The details of the column temperature program were as follows: first, it kept at 333.15 K for 4 min; then, it rose to 373.15 K with the increment of 10 K/min, and finally, it stayed at 373.15 K for 2.5 min. Received: September 7, 2017 Accepted: January 9, 2018 Published: January 22, 2018 395
DOI: 10.1021/acs.jced.7b00802 J. Chem. Eng. Data 2018, 63, 395−401
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Table 1. Materials Description at 101.3 kPaa CASRN
source
initial mole fraction purity
purification method
final mole fraction purity
analysis method
n-hexane
110-54-3
McLean reagent
0.995
0.9991
GCb
methyl cyclopentane
96-37-7
McLean reagent
0.990
0.9968
GCb
1,2-dimethoxyethane
110-71-4
McLean reagent
0.995
dehydration distillation dehydration distillation dehydration distillation
0.9979
GCb
chemical name
a
Standard uncertainties u(P) = 0.3 kPa. bGas chromatography.
Table 3. Isobaric VLE Data for Temperature T, Liquid Phase Mole Fraction x, Vapor Phase Mole Fraction y, Activity Coefficient γ, and Relative Volatilities α for the System nHexane + 1,2-Dimethoxyethane at 101.3 kPaa
Each sample test was performed at least two times. The standard uncertainty of compositions was 0.005 in mole fraction of the two repeated measurements. 2.3. Apparatus and Procedure. The VLE data were carried out by an Ellis equilibrium still. The disadvantage of the still is that a higher amount of the reagents must be used, while its advantage is that the data obtained from Ellis equilibrium still on several binary systems show very good agreement with previous work and are thermodynamically consistent.11 The previous literature12 showed that the apparatus used in measuring the saturated vapor pressure data was reliable. The experimental still is shown in Figure 1. The apparatus contains liquid-phase sampling port, vapor-phase sampling port,
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.12
equilibrium chamber, heating bar, and condenser. Both the vapor and the liquid phase were continuously circulating to ensure the equilibrium could be established in the equilibrium process. In each experiment, equilibrium between the vapor and the liquid phases was assumed when the temperature remained constant for 60 min or longer. The uncertainty of the CENTER-375 thermometer was 0.05 K. The pressure was measured with the testo-511 digital vacuum gauge, which had an uncertainty of 0.3 kPa.
T/K
x1
y1
γ1
γ2
α12
341.88 342.15 342.25 342.61 342.86 343.46 344.02 344.53 345.21 345.94 346.28 346.72 347.79 348.51 349.43 350.23 351.49 353.49 354.13 354.81 354.94 355.34 355.76 355.92 356.16 356.44 357.01 357.14 357.22 357.75
1 0.9218 0.8922 0.7831 0.7505 0.6710 0.6269 0.5813 0.5248 0.4636 0.4423 0.3824 0.3379 0.3060 0.2679 0.2349 0.1981 0.1186 0.1001 0.0697 0.0682 0.0614 0.0573 0.0474 0.0404 0.0315 0.0155 0.0114 0.0096 0
1 0.9311 0.9060 0.8186 0.7981 0.7474 0.7102 0.6814 0.6350 0.5912 0.6004 0.5563 0.5097 0.4757 0.4296 0.3883 0.3410 0.2193 0.1916 0.1398 0.1375 0.1256 0.1186 0.0995 0.0859 0.0686 0.0345 0.0255 0.0218 0
1.0015 1.0037 1.0218 1.0314 1.0604 1.0601 1.0801 1.0920 1.1255 1.1858 1.2541 1.2591 1.2703 1.2748 1.2837 1.2876 1.3052 1.3265 1.3643 1.3666 1.3694 1.3693 1.3813 1.3897 1.4143 1.4192 1.4295 1.4396
1.4926 1.4717 1.3925 1.3356 1.2404 1.2301 1.1832 1.1660 1.1280 1.0479 1.0346 1.0277 1.0226 1.0219 1.0205 1.0053 1.0133 1.0061 1.0125 1.0092 1.0026 0.9924 0.9982 0.9980 0.9983 0.9994 1.0002 1.0001
1.1455 1.1638 1.2500 1.3140 1.4504 1.4582 1.5409 1.5758 1.6731 1.8945 2.0251 2.0365 2.0581 2.0582 2.0678 2.0936 2.0866 2.1298 2.1701 2.1797 2.1948 2.2130 2.2180 2.2295 2.2656 2.2653 2.2787 2.2951
a
Standard uncertainties u are u(T) = 0.05 K, u(P) = 0.3 kPa, and u(x1) = u(y1) = 0.005.
3. RESULTS AND DISCUSSION 3.1. Vapor−Liquid Equilibrium Model. Eq 1, which is used to calculate the activity coefficient, expresses the equilibrium relationship between vapor and liquid phase:13
Table 2. Extended Antoine Equation Coefficients C1−C5 for the Chemicals component
C1
C2
C3
C4
C5
T/K range
n-hexane 1,2-dimethoxyethane methylcyclopentane
97.742 54.906 48.46
−6995.5 −6102.9 −5149.8
−12.702 −5.6547 −5.0136
1.2 × 10−5 1.2 × 10−17 3.2 × 10−6
2 6 2
177.83−507.60 215.15−536.15 130.73−532.70
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Table 4. Isobaric VLE Data for Temperature T, Liquid Phase Mole Fraction x, Vapor Phase Mole Fraction y, Activity Coefficient γ, and Relative Volatilities α for the System Methylcyclopentane + 1,2-Dimethoxyethane at 101.3 kPaa T/K
x1
y1
γ1
γ2
α12
344.96 345.15 345.18 345.47 346.02 346.5 347.07 347.49 348.29 349.01 349.76 350.52 351.57 352.39 353.27 354.11 354.84 355.48 356.04 356.48 357.14 357.28 357.75
1 0.9427 0.8467 0.7498 0.6693 0.5744 0.5204 0.4723 0.4212 0.3752 0.3340 0.2859 0.2319 0.1909 0.1458 0.1105 0.0749 0.0547 0.0415 0.0263 0.0098 0.0052 0
1 0.9461 0.8617 0.7824 0.7196 0.6477 0.6070 0.5704 0.5306 0.4937 0.4591 0.4161 0.3636 0.3192 0.2640 0.2146 0.1575 0.1208 0.0949 0.0625 0.0246 0.0131 0
1.0017 1.0105 1.0268 1.0403 1.0750 1.0928 1.1171 1.1374 1.1622 1.1869 1.2290 1.2827 1.3349 1.4092 1.4755 1.5638 1.6124 1.6409 1.6884 1.7360 1.7531
1.4321 1.3716 1.3088 1.2513 1.2014 1.1659 1.1416 1.1061 1.0784 1.0535 1.0333 1.0107 0.9986 0.9929 0.9894 0.9963 0.9963 0.9932 0.9982 0.9997 1.0022
1.0662 1.1278 1.1994 1.2680 1.3621 1.4233 1.4833 1.5536 1.6235 1.6920 1.7807 1.8920 1.9864 2.1017 2.2010 2.3101 2.3760 2.4203 2.4739 2.5333 2.5507
Figure 3. Relative volatilities of the methylcyclopentane + 1,2dimethoxyethane system at 101.3 kPa. Comparison of model results (calculated with NRTL parameters in Table 6) to the experimental data. The chart also shows (dash lines) ±5% deviations from the calculated relative volatilities.
Table 5. Thermodynamic Consistency Check system n-hexane + 1,2dimethoxyethane methylcyclopentane + 1,2-dimethoxyethane
a
Standard uncertainties u are u(T) = 0.05 K, u(P) = 0.3 kPa, and u(x1) = u(y1) = 0.005.
J
D−J
L
W
E
5.34
6.96
−1.62
3.2
3.29
1.33
7.99
5.56
2.43
2.9
2.96
0.99
Figure 4. Diagram of ln(γ1/γ2) to x1 for the n-hexane + 1,2dimethoxyethane system.
Figure 2. Relative volatilities of the n-hexane + 1,2-dimethoxyethane system at 101.3 kPa. Comparison of model results (calculated with NRTL parameters in Table 6) to the experimental data. The chart also shows (dash lines) ±5% deviations from the calculated relative volatilities.
⎛ v l (p − p s ) ⎞ i ⎟ s s ⎜ i exp p yi φivp = xiγφ i i i ⎜ ⎟ RT ⎝ ⎠
D
mixture, φsi is the fugacity coefficient in the saturate state, psi is the saturated vapor pressure, υli is the liquid molar volume of pure component i. The Poynting factor exp(Vli(p − psi )/RT) in eq 1 is close to unity at 101.3 kPa. The vapor phase is usually treated ideality when under negative pressure. The liquid phase fugacity is assumed to be 1, so eq 1 can be simplified as
(1)
where p is the total pressure, T is the temperature, R is the universal gas constant, xi and yi are the mole fractions of component i in the liquid phase and vapor phase, respectively, φvi is the fugacity coefficient of component i in the vapor
yip = xiγipis
(2)
Using the extended Antoine expression, eq 3 can obtain the vapor pressures of the pure components, where T/K is the 397
DOI: 10.1021/acs.jced.7b00802 J. Chem. Eng. Data 2018, 63, 395−401
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Figure 5. Diagram of ln(γ1/γ2) to x1 for the methylcyclopentane + 1,2dimethoxyethane system.
Figure 6. Experimental data and calculated data for the system of nhexane + 1,2-dimethoxyethane at 101.3 kPa. ■, experimental x1; △, experimental y1; --, calculated x1 with NRTL model; -, calculated y1 with NRTL model.
temperature and psi /kPa is the standard vapor pressure of pure component i. The coefficients C1 to C5 and the ranges of T are obtained from Aspen Plus and listed in Table 2. ln(pis /kPa) = C1, i + C2, i /(T /K) + C3, i ln(T /K) + C4, i(T /K)C5,i
(3)
3.2. VLE Data. The isobaric VLE experimental data, the activity coefficients, and the relative volatilities for the binary systems of n-hexane + 1,2-dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane at 101.3 kPa are all listed in Tables 3 and 4, respectively. The literatures14−16 show that the measured boiling points of n-hexane, 1,2-dimethoxyethane, and methylcyclopentane are 341.79, 358.30, and 353.4 K, respectively. Comparing with the measured values in Tables 3 and 4, the relative deviations of the 3 boiling points are all less than 3%. The results show that the measured boiling points of the three components in this work are reliable. The activity coefficients of the two systems are all greater than 1, which show positive deviations from the ideality. The relative volatilities17,18 can be obtained as follows:
(4)
Figure 7. Experimental data and calculated data for the system of nhexane + 1,2-dimethoxyethane at 101.3 kPa. ■, experimental x1; △, experimental y1; --, calculated x1 with Wilson model; -, calculated y1 with Wilson model.
where α12 is the relative volatility and x1 and y1 are the liquid and vapor mole fractions, respectively. Figures 2 and 3 compare the experimental relative volatilities for the two binary systems
with results calculated by using model parameters in Table 6. The calculated results agree well with experimental data. The
a12 =
y1 /x1 (1 − y1)/(1 − x1)
Table 6. Correlation Parameters and Root Mean Square Deviations for the Binary Systems correlation parametersa system n-hexane + 1,2-dimethoxyethane
methylcyclopentane + 1,2-dimethoxyethane
models f
NRTL UNIQUAC Wilson NRTL UNIQUAC Wilson
aijb
c
aji
2.0693 −3.3439 0.1427 −7.1043 2.3961 −7.3142
−5.1962 1.9036 0.5016 10.255 −7.0821 3.1229
RMSD
bij
bji
σy1d
−633.52 468.00 −746.06 2403.2 −1303.5 1744.8
1883.0 −628.02 −543.92 −3315.9 2250.9 −1076.6
0.007 0.007 0.007 0.002 0.002 0.002
σTe 0.133 0.133 0.134 0.282 0.280 0.280
a
a and b parameters of the NRTL, UNIQUAC, or Wilson model. bSubscripts ij represents the pair interaction. cSubscripts ji represents the pair exp 2 est exp 2 1/2 e 1/2 f interaction. dσy1 = (∑(yest 1,i − y1,i ) /n) . σT = (∑(Ti − Ti ) /n) . The value of αij was fixed at 0.3 for the 2 binary systems as these systems 19 belong to type I according to the definition in the literature. 398
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Figure 8. Experimental data and calculated data for the system of nhexane + 1,2-dimethoxyethane at 101.3 kPa. ■, experimental x1; △, experimental y1; --, calculated x1 with UNIQUAC model; -, calculated y1 with UNIQUAC model.
Figure 10. Experimental data and calculated data for the system of methylcyclopentane + 1,2-dimethoxyethane at 101.3 kPa. ■, experimental x1; △, experimental y1; --, calculated x1 with Wilson model; -, calculated y1 with Wilson model.
Figure 9. Experimental data and calculated data for the system of methylcyclopentane + 1,2-dimethoxyethane at 101.3 kPa. ■ , experimental x1; △, experimental y1; --, calculated x1 with NRTL model; -, calculated y1 with NRTL model.
Figure 11. Experimental data and calculated data for the system of methylcyclopentane + 1,2-dimethoxyethane at 101.3 kPa. ■, experimental x1; △, experimental y1; --, calculated x1 with UNIQUAC model; -, calculated y1 with UNIQUAC model.
J = 150 ×
maximum model deviation is 5% for n-hexane + 1,2dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane binary mixtures. It demonstrates that the experimental data are principally consistent with calculated results. The two binary systems both exhibit positive deviations from ideality. 3.3. Thermodynamic Consistency Tests of Binary Systems. Tests of thermodynamic consistency for all the experimental data were verified by the Herington test6 and Wisniak test.7 The Herington test is used to examine the VLE data by area test. The Wisniak test is used to examine the VLE data by point-to-point test. Herington method is expressed as eq 5 and eq 6:
Tmax − Tmin Tmin
(6)
In which D − J must be less than 10. Tmax/K and Tmin/K are the highest and the lowest boiling points in the system, respectively. The Wisniak method is shown in eqs 7−9. The criteria of the Wisniak test is that the coefficient E should be smaller than 3.7
E = 100
1
1
1
1
∫0 Ldx1 − ∫0 W dx1 ∫0 Ldx1 + ∫0 W dx1
(7)
1
D=
∫0 ln(γ1/γ2)dx1 1
∫0 |ln(γ1/γ2)|dx1
× 100
L=
(5) 399
∑ TioxiΔsio −T ∑ xiΔsio
(8) DOI: 10.1021/acs.jced.7b00802 J. Chem. Eng. Data 2018, 63, 395−401
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⎡⎛ exp 2 ⎛ pexp − pest ⎞2 Ti − Tiest ⎞ i ⎟ ⎢ Q=∑ ⎜ ⎟ + ⎜⎜ i ⎟ ⎢⎝ σ σ ⎠ ⎝ ⎠ T p i=1 ⎣ N
2 ⎛ xiexp − xiest ⎞2 ⎛ yiexp − yiest ⎞ ⎤ ⎟⎟ ⎥ +⎜ ⎟ + ⎜⎜ σx σ ⎝ ⎠ ⎝ ⎠ ⎥⎦ y
(10)
where σ is the standard deviation of the indicated data, N is the number of experimental points, T is the equilibrium temperature, xi and yi are the liquid mole fraction and vapor mole fraction of the light component, respectively, superscripts exp and est are the abbreviation of experiment and estimate, respectively, and Q is the objective function to be minimized by data regression. The binary interaction parameters and the RMSD for the binary systems at 101.3 kPa are shown in Table 6. It can be observed that the RMSD of vapor phase composition is no more than 0.007, and the RMSD of the temperature is no more than 0.282. The calculated results of the vapor phase composition and temperature by three models tend to be the same, which show reasonably good agreement with the experimental values. The plots of three models for the systems of n-hexane + 1,2dimethoxyethane are shown separately in Figures 6−8, for the systems of methylcyclopentane + 1,2-dimethoxyethane are plotted separately in Figures 9−11, and the combined plots of three models for the two systems are also shown below in Figures 12 and 13 to make the comparison more clearly. All tables and figures indicate that the correlated values agree well with VLE data.
Figure 12. Combined plots of Figures 6−8 for the systems of n-hexane + 1,2-dimethoxyethane at 101.3 kPa.
4. CONCLUSION New isobaric VLE values of binary systems n-hexane + 1,2dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane were measured at 101.3 kPa, and all experimental data passed the thermodynamic consistency test with Herington test and Wisniak method. The VLE data were regressed, and the corresponding binary interaction parameters were correlated by the NRTL, UNIQUAC, and Wilson models, which agreed well with the experimental data. The two binary systems show positive deviations from ideality. The experimental results for the two binary systems n-hexane + 1,2-dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane expanded the VLE database, providing data support for further study.
Figure 13. Combined plots of Figures 9−11 for the systems of methylcyclopentane + 1,2-dimethoxyethane at 101.3 kPa.
W=
RT ⎛ ⎜∑ xi ln γi − ∑ xiΔsio ⎝
∑ xi ln
yi ⎞ ⎟ xi ⎠
(9)
where Toi is the boiling point of component i, Δsoi is the molar entropy of vaporization of component i, and k is each experimental point. The results of area test and point test are shown in Table 5 and Figures 4 and 5, which all satisfy the consistent criteria, indicating that the experimental VLE data of the binary systems for n-hexane + 1,2-dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane can be considered as thermodynamically consistent at 101.3 kPa. 3.4. Data Regression. The experimental data of binary systems were fitted with the NRTL, UNIQUAC, and Wilson models based on Aspen Plus. The maximum likelihood objective function was used in the regression calculation. In this function, errors of T and y were considered. The function is shown as follows:
■
AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. ORCID
Lanyi Sun: 0000-0002-3158-6388 Funding
This work was supported by the National Natural Science Foundation of China (Grants 21676299, 21506255, and 21476261) and the Fundamental Research Funds for the Central Universities (Grant 17CX06025). Notes
The authors declare no competing financial interest. 400
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