Isobaric VaporâLiquid Equilibrium for Binary and Ternary Systems of

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Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Isobaric Vapor−Liquid Equilibrium for Binary and Ternary Systems of tert-Butanol + tert-Butyl Acetate + Chlorobenzene at 101.33 kPa Kai Fan, Feng Zhou, Changxu Chen, Ye Li, Weisong Li, Bo Xiao,* and Chunjian Xu* School of Chemical Engineering and Technology, Chemical Engineering Research Center, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, China

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S Supporting Information *

ABSTRACT: Isobaric vapor−liquid equilibria of tert-butanol + chlorobenzene and tert-butyl acetate + chlorobenzene binary systems and the tert-butanol + tertbutyl acetate + chlorobenzene ternary system at 101.33 kPa were measured using a circulation VLE still. The data of binary systems passed the thermodynamic consistency test of the Herington method and the Van Ness point test, and the experimental data of the ternary system also passed the Wisniak consistency test. These binary systems’ VLE data were fitted by the Wilson, nonrandom two-liquid (NRTL), and universal quasichemical (UNIQUAC) activity coefficient models with minor deviations. Furthermore, the obtained binary interaction parameters from the binary systems were used to predict the VLE behavior of the tert-butanol + tert-butyl acetate + chlorobenzene ternary system. The rmsd of vapor and the temperature between the experimental and predicted values for the ternary system were smaller than 0.0304 and 0.81K, respectively. The results indicated that the relative volatility between tert-butanol and tert-butyl acetate obviously increased when adding chlorobenzene as a solvent. Thus, chlorobenzene is a promising solvent for the separation of the tert-butanol and tert-butyl acetate mixture system by extractive distillation.

1. INTRODUCTION tert-Butyl acetate (TBAc) is generally used as a solvent in the production of various chemical products, such as coatings, enamels, nitrocellulose, and adhesives.1,2 In recent years, the use of TBAc, an environmentally friendly nonhazardous solvent, in surface treatment and oil stabilization has seen a dramatic increase.3,4 One of the advantages of TBAc is that it can reduce the photochemical reactive and VOC content of target products.4 The universal method of TBAc synthesis is based on the esterification of tert-butanol (TBA) and acetic acid using zinc chloride (or N,N-dimethylformamide) as the catalyst.5,6 In previous work, TBA was routinely used as a raw material for butyl rubber production or as a gasoline additive agent which has been added to neat fuel, gasoline, diesel, jet fuel, aviation gasoline, and heating oil as an oxygenated fuel constituent.7 Monton et al. found that tert-butanol and tertbutyl acetate exist in a low relative volatility region.8 When the mole fraction of tert-butanol is greater than 0.91, the gap between the vapor and liquid composition of tert-butanol and tert-butyl acetate is negligible in the temperature−composition diagram. Therefore, it is very difficult to separate tert-butanol and tert-butyl acetate by conventional distillation, which has been a handicap for the purification of tert-butyl acetate and the industrial application of tert-butanol. Among the separation methods in the chemical industry, extractive distillation is more often applied for the separation of close-boiling mixtures.9 Extractive distillation has an inherent advantage in that it can reduce the energy requirement,10 and © XXXX American Chemical Society

the suitable entrainer plays a key role in an effective and economical process.11−14 Chlorobenzene is an excellent entrainer because of its favorable characteristics and molecular polarity. The capability of chlorobenzene as a modified distillation agent is discussed in previous work.15−17 In this article, the entrainer behavior of chlorobenzene in tert-butanol + tert-butyl acetate separation has been investigated. Because reliable vapor−liquid equilibrium data of the mixture is essential to process simulation and optimization in extractive distillation processes, we have focused our research on the VLE of the tert-butanol + tert-butyl acetate + chlorobenzene system at 101.33KPa, which has not been reported yet. This article presents the isobaric VLE data for binary systems TBA(1) + chlorobenzene(3) and TBAc(2) + chlorobenzene(3) and ternary system TBA(1) + TBAc(2) + chlorobenzene(3) at 101.33 kPa. The thermodynamic consistency was checked by the Herington method,18 the Van Ness test described by Fredenslund,19 and the Wisniak test.20,21 Meanwhile, the experimental data of binary and ternary systems were correlated by the Wilson,22 NRTL,23 and UNIQUAC24 equations, and the obtained interaction parameters of the binary systems were employed to predict that of the ternary system of TBA(1) + TBAc(2) + chlorobenzene(3), which were in turn compared to the experimental VLE results. Received: November 21, 2017 Accepted: June 13, 2018

A

DOI: 10.1021/acs.jced.7b01021 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Description of Materialsa normal boiling point (Tb/K) component

source

CAS registry number

GC purity (mass)

exp

lit

tert-butanol tert-butyl acetate chlorobenzene

Energy Chemical Co., Ltd. Energy Chemical Co., Ltd. Aladdin, China

75-65-0 540-88-5 108-90-7

0.9979 0.9990 0.9991

355.59 371.05 404.80

355.578 371.158 404.8415

a

Standard uncertainty u is u(Tb) = 0.05 K by calibration.

2. EXPERIMENTAL SECTION 2.1. Materials. tert-Butanol, tert-butyl acetate, and chlorobenzene were analytical reagents. All of these chemicals were of high purity as measured by gas chromatography and were used without further purification. The water content of the chemicals determined by Karl Fischer titration was less than 500 ppm. Furthermore, the chemical specification of substances was measured with a circulation VLE still. Comparisons between the experimental and literature data are presented in Table 1. 2.2. Apparatus and Procedures. The modified Rose− Williams equilibrium still apparatus (Tianjin University instrument, China) was used to measure the binary and ternary vapor−liquid data, which is shown in Figure 1.

The liquid−vapor equilibrium data were measured with a gas chromatograph (GC7890A, Agilent Technologies Inc.) equipped with a thermal conductivity detector (TCD). Before experiments, the instrument was calibrated with standard solutions, and the desiccant used in the instrument was checked for its water absorption property to avoid the influence of water on the process. The GC column was an Agilent DB-WAX, and the carrier gas was hydrogen with a 20 mL/min constant velocity. The detector and injector temperatures were both 523.15 K. The programmed temperature was held at 393.15 K (initial set) and then increased to 433.15 K at 10 K·min−1.

3. RESULTS AND DISCUSSION 3.1. Vapor−Liquid Equilibrium Measurements. The isobaric VLE data of TBA(1) + chlorobenzene(3) and TBAc(2) + chlorobenzene(3) and the ternary system of TBA(1) + TBAc(2) + chlorobenzene(3) were measured with a Rose−Williams VLE apparatus. The results are tabulated in Tables 2−4. The VLE data that are listed consist of the equilibrium temperature (T), the equilibrium mole fraction of the liquid phase (xi), the equilibrium mole fraction of the vapor phase (yi), and the activity coefficient (γi) of each component. Table 2. Experimental Vapor−Liquid Equilibrium Data and Calculated Values for the Binary System of tert-Butanol(1) + Chlorobenzene(3) at 101.33 kPaa

Figure 1. Diagrammatic sketch of the VLE apparatus. (1) Heating rod, (2) liquid-phase sampling port, (3) equilibrium chamber, (4) mercury thermometer, (5) condenser, and (6) vapor-phase sampling port.

The still was equipped with a heating rod as the energy source and precisely calibrated thermometers (50−100 and 100−150 °C) with a minimum value of 0.1 °C to measure the temperature. In this work, we used a pressure-control system (mainly including a gas buffer and a LEYNOW-HP-1200 V vacuum pump) equipped with a U-shaped differential mercury manometer to measure the pressure of our system, whose uncertainty was 0.25 kPa. A detailed descriptions of the Rose− Williams equilibrium apparatus had been reported in previous work,25 and the experimental reliability had been demonstrated by VLE data comparison (Supporting Information).

T/K

x1

y1

γ1b

355.59 356.50 356.95 357.15 358.05 358.45 359.75 361.25 362.65 363.50 365.15 368.55 373.85 379.95 385.45 390.45 395.15 397.85 402.05 404.80

1.0000 0.8859 0.8536 0.8156 0.7455 0.7101 0.6223 0.5364 0.4620 0.4263 0.3671 0.2707 0.1781 0.1128 0.0715 0.0460 0.0309 0.0207 0.0073 0.0000

1.0000 0.9502 0.9382 0.9240 0.9010 0.8893 0.8647 0.8391 0.8155 0.8046 0.7800 0.7313 0.6547 0.5570 0.4515 0.3510 0.2677 0.1999 0.0831 0.0000

1.0000 1.0207 1.0275 1.0509 1.0822 1.1040 1.1645 1.2373 1.3232 1.3700 1.4494 1.6245 1.8257 1.9842 2.0836 2.1685 2.1259 2.1776 2.2615

γ3 1.9701 1.8756 1.8190 1.6622 1.6091 1.4411 1.3238 1.2460 1.2010 1.1583 1.0944 1.0479 1.0259 1.0219 1.0184 0.9857 0.9900 0.9969 1.0000

a

Standard uncertainties u are u(T) = 0.05 K, u(P) = 0.25 kPa, u(x1) = 0.001, and u(y1) = 0.001. bγi represents the activity coefficients. B



Article

Table 3. Experimental Vapor−Liquid Equilibrium Data and Calculated Values for the Binary System of tert-Butyl Acetate(2) + Chlorobenzene(3) at 101.33 kPaa T/K

x2

y2

γ2

371.05 371.29 372.13 374.51 377.43 380.32 384.70 387.45 389.61 391.86 393.12 394.80 396.03 397.96 399.75 400.62 402.06 403.67 404.31 404.80

1.0000 0.9514 0.9123 0.8244 0.7381 0.6495 0.5562 0.5093 0.4499 0.4048 0.3685 0.3255 0.2899 0.2385 0.1981 0.1677 0.1135 0.0597 0.0313 0.0000

1.0000 0.9891 0.9789 0.9497 0.9111 0.8575 0.7831 0.7371 0.6709 0.6151 0.5706 0.5054 0.4527 0.3750 0.3080 0.2614 0.1740 0.0895 0.0460 0.0000

1.0000 1.0265 1.0325 1.0317 1.0137 0.9963 0.9375 0.8924 0.8665 0.8305 0.8179 0.7841 0.7633 0.7306 0.6896 0.6759 0.6408 0.6017 0.5805

Table 5. Antoine Equation Constants

γ3 0.6095 0.6380 0.7034 0.7582 0.8297 0.8713 0.8791 0.9206 0.9316 0.9444 0.9705 0.9847 0.9931 0.9931 0.9972 1.0061 1.0005 1.0000 1.0000

a

compound

A

B

C

tert-butanola tert-butyl acetatea chlorobenzeneb

16.5954 14.4645 6.10416

−3575.89 −3160.68 −1431.83

−56.991 −49.868 −55.515

Antoine equation:8 ln(P /kPa) = A + 15

tion: log10(P /kPa) = A +

B T /K + C

b

Antoine equa-

B T /K + C

pressure, the Poynting factor exp(VLi (p − psi )/RT) can be regarded as 1, and eq 1 can be simplified to V PØ̂ i yi = pis Øis γixi

(2)

γi is the activity coefficient of component i and can be deduced from eq 2. The experimental activity coefficients are listed in Tables 2−4. 3.3. Thermodynamic Consistency Tests. In this work, binary experimental results were examined with respect to thermodynamic consistency using the Herington method18 and the Van Ness test.19 The Van Ness test was used to check the ternary system. The Herington method can be expressed and modified as20,26

a

Standard uncertainties u are u(T) = 0.05 K, u(P) = 0.25 kPa, u(x1) = 0.001, and u(y1) = 0.001.

1

D = 100

∫0 ln(γ1/γ2) dx1 1

∫0 |ln(γ1/γ2)| dx1 The basic VLE relationship in this mixtures system, considering nonideality for the system, can be expressed as

ij ViL(P − ps ) yz i z zz expjjjj = zz j RT (1) k { where P is the total system pressure; Ø̂ Vi is the component i fugacity coefficient in the vapor; psi is the vapor pressure of pure component i at the system temperature, calculated by the Antoine equation, where the Antoine constants of each component can be found in Table 5; Øsi is the fugacity coefficient of pure vapor i at system temperature T and saturation pressure psi ; γi is the activity coefficient; and VLi is the mole volume of pure liquid i. Ø̂ Vi and Øsi could be calculated with the Soave−Redlich−Kwong (SRK) equation. At low V PØ̂ i yi

ΔHm

Jmodified = 34 ×

pis Øis γixi

ΔGmE

×

(3)

T10 − T20 Ti

(4)

T01 and T02 represent the boiling points of pure components (1) and (2) at the operating pressure. Ti is the lowest boiling point. ΔHm/ΔGmE is calculated on the basis of the following equations: ΔHm (J ·mol−1) = − 237.02 + 1.3863 × ΔGmE (J· mol−1) (5)

ΔGE = RT ∑ xi ln γi

(6)

The VLE data can be considered to be thermodynamically consistent if |D − Jmod| < 10.

Table 4. Experimental Vapor−Liquid Equilibrium Data and Correlated Values for the Ternary System of tert-Butanol(1) + tert-Butyl Acetate(2) + Chlorobenzene(3) at 101.33 kPaa T/K

x1

x2

y1

y2

γ1

γ2

γ3

363.85 364.25 364.55 364.80 366.65 367.55 369.55 371.65 375.32 379.20 381.82 385.55

0.5222 0.4830 0.4802 0.4181 0.3151 0.2699 0.2257 0.1670 0.1123 0.0709 0.0453 0.0205

0.0152 0.0400 0.0366 0.1079 0.1712 0.2190 0.2694 0.3230 0.3903 0.4294 0.4609 0.4840

0.8044 0.7884 0.7877 0.7619 0.7316 0.6980 0.6510 0.5850 0.4700 0.3565 0.2314 0.1266

0.0066 0.0177 0.0162 0.0491 0.0761 0.1101 0.1587 0.2130 0.3070 0.4200 0.5243 0.6142

1.1104 1.1587 1.1511 1.2909 1.5056 1.6214 1.6795 1.8892 1.9793 2.0767 1.9289 2.0582

0.5372 0.5403 0.5361 0.5562 0.5036 0.5537 0.6095 0.6395 0.6827 0.7572 0.8166 0.8197

1.4292 1.4029 1.3861 1.3730 1.1888 1.1565 1.0852 1.0632 1.0674 0.9409 0.9591 0.9047

a

Standard uncertainties u are u(T) = 0.05 K, u(P) = 0.25 kPa, u(x1) = 0.001, and u(y1) = 0.001. C



Article

3.4. Data Correlation. The experimental data of tertbutanol(1) + chlorobenzene(3) and tert-butyl acetate(2) + chlorobenzene(3) systems were correlated with the Wilson, NRTL, and UNIQUAC activity coefficient models.20−22 The interaction parameters of these models were adopted by minimizing the objective function (OF):28 ÅÄÅ ÑÉ exp cal y2 Ñ ÑÑ N Å 2 i ÅÅji T exp − T cal zy2 − y y j z j z k ,i k ,i z Ñ ÑÑ z OF = ∑ ÅÅÅÅjjjj i exp i zzzz + ∑ jjjj z exp zz ÑÑÑÑ ÅÅ j T y i i=1 Å k=1 k k ,i { ÅÅÇk { ÑÑÑÖ (12)

The Van Ness test can be considered to be a modeling capability test.27 The Wilson model is used to examine the thermodynamic consistency. The criterion is expressed as22 N

Δy =

1 ∑ 100|yiexp − yical | N i=1

(7)

N is the number of data points. It can be considered that the VLE data pass the test if Δy is less than 1. The results of thermodynamic consistency tests of TBA(1) + chlorobenzene(3) and TBAc(2) + chlorobenzene(3) and ternary system TBA(1) + TBAc(2) + chlorobenzene(3) are presented in Table 6. It can be seen that the |D − Jmod| values

N is the number of experimental points; Tiexp and Tical are the experimental and calculated temperatures, respectively; and cal yexp k,i and yk,i are the experimental and calculated vapor mole fractions, respectively. The correlated parameters of the abovementioned three models, the root-mean-square deviations (rmsd) of the vapor mole fraction, and the boiling temperature between the experimental and calculated data are listed in Table 7. The T−x−y relationship for binary systems is shown in Figures 2 and 3. As seen in Table 7 and Figures 2 and 3, the experimental data were shown to be in good agreement with the predicted data drawn from three activity coefficient models. The vapor rmsd and temperature predicted from the model regression with the correlated parameters were below 0.0119 and 0.62 K, respectively. Therefore, all three models can be suitable for the studied systems. 3.5. Prediction of Ternary Vapor−Liquid Equilibrium. On the basis of the above-mentioned three activity coefficient models, the obtained binary interaction parameters were used to predict that of the ternary system of TBA(1) + TBAc(2) + chlorobenzene(3), and the predicted data was in turn compared to the experimental result. The maximum absolute deviation and mean absolute deviation of equilibrium temperature and vapor composition are listed in Table 8. The results show that the three models are suitable for the ternary system. The relative volatility analysis29 (Supporting Information) of the tert-butanol to tert-butyl acetate system is shown in Figure 4. The chart clearly demonstrates that the chlorobenzene can increase the relative volatility of the tert-butanol to tert-butyl acetate system. The ternary VLE data are listed in Table 4 and illustrated in Figure 5. Dashed lines in Figure 5 represented the calculated values by the activity coefficient model. The y1−x1

Table 6. Thermodynamic Consistency Test Results system TBA(1) + chlorobenzene(3) TBAc(2) + chlorobenzene(3)

D

Jmod

|D − Jmod|

Δy1

Δy2

0.682

6.232

5.55

0.112

0.112

0.586

4.606

4.02

0.200

0.200

of the TBA(1) + chlorobenzene(3) and TBAc(2) + chlorobenzene(3) binary systems are 5.55 and 4.02, respectively. And the Δy were less than 0.3. The results indicated that the experimental data passed the testing criterion. The ternary system was found to be thermodynamically consistent by the Wisniak L-W test.20,21 The test is described by the following equations. According to this method, the average and maximum values of Fk are 1.212 and 3.692, respectively. The data can be considered to be thermodynamically consistent if Fk < 5. Fk = 100 × Lk =

|Lk − Wk| Lk + Wk

(8)

∑ Ti0xiΔsi0/Δs − T =

GE RTω − = Wk Δs Δs

Δs = x1Δs10 + x 2Δs20 + x3Δs30

(9) (10)

ij y yz ij y yz ij y yz ω = x1 lnjjj 1 zzz + x 2 lnjjj 2 zzz + x3 lnjjj 3 zzz jx z jx z j x3 z k 1{ k 2{ k {

(11)

Table 7. Correlation Parameters and Root-Mean-Square Deviations (rmsd) of the Systems correlation parameters model

aij

bij/K

rmsd aji

bji/K

σT

σy1a

a

8

Wilsonb NRTL(α = 0.3)c UNIQUACd

−0.4288 −0.2200 0.9428


−0.5663 0.5109 1.9823


0.3400 −35.4098 −0.7573

tert-Butanol(1) + tert-Butyl Acetate(2) 0.0313 3.9329 −0.0252 tert-Butanol(1) + Chlorobenzene(3) 0.9960 −0.4354 1.0060 0.3925 −529.1040 −1.4153 tert-Butyl Acetate(2) + Chlorobenzene(3) 0.9987 0.1371 21 000.84 −3.7918 0.9526 0.7511 −0.0026 −0.2417 −219.1850

−0.0038 1629.0480 −181.0660

0.25 0.17 0.17

0.0034 0.0020 0.0019

0.9964 1.0050 110.4767

0.58 0.62 0.45

0.0015 0.0016 0.0085

0.9983 1236.8450 0.9079

0.45 0.58 0.43

0.0018 0.0037 0.0119

c d cal 2 1/2 cal 2 1/2 b σy1 = [(1/n)∑ni=1(yexp and σT = [(1/n)∑ni=1(Texp 1,i − y1,i ) ] i − Ti ) ] . Wilson: ln Aij = aij + bij/T. NRTL: τij = aij + bij/T. UNIQUAC: τij = exp(aij + bij/T). a

D



Article

Figure 4. Relative volatility of tert-butanol to tert-butyl acetate at 101.33 kPa: (●) experimental data without chlorobenzene; (○) experimental data with chlorobenzene (w3 = 0.50). Solid lines are calculated by the Wilson model.

Figure 2. Temperature−composition diagram for tert-butanol(1) + chlorobenzene(3) at 101.33 kPa.(■) x−T from experimental data; (●) y−T from experimental data; () from the NRTL model; (---) from the Wilson model; and (···) from the UNIQUAC model.

Figure 5. VLE comparison and tie lines for the ternary system of tertbutanol(1) + tert-butyl acetate(2) + chlorobenzene(3) at 101.33 kPa. (●) Liquid-phase experimental data; (○) vapor-phase experimental data; and (☆) data predicted by the Wilson model.

Figure 3. Temperature−composition diagram for tert-butyl acetate(2) + chlorobenzene(3) at 101.33 kPa. (■) x−T for the experimental data; (●) y−T for the experimental data; () NRTL model; (---) Wilson model; and (···) UNIQUAC model.

chlorobenzene are shown in Figure 6. The vapor−liquid equilibrium composition difference of the binary system was negligible in the vicinity of pure tert-butanol. However, when chlorobenzene, as the extractive solvent of the above binary

diagram of the tert-butanol (1) + tert-butyl acetate (2) binary system and its behavior in the ternary system including

Table 8. Mean Absolute Deviations of Equilibrium Temperature and Vapor-Phase Mole Fraction for the Ternary System maximum absolute deviations

mean absolute deviations

model

ΔmaxT/Ka

Δmaxy1a

Δmaxy2a

Δmaxy3a

δT/Kb

δy1c

δy2c

δy3c

Wilson NRTL UNIQUAC

1.46 1.51 1.56

0.0441 0.0508 0.0294

0.0643 0.0608 0.0611

0.0306 0.0288 0.0465

0.65 0.81 0.73

0.0240 0.0259 0.0164

0.0295 0.0304 0.0245

0.0207 0.0175 0.0283

ΔmaxT and Δmaxy are the maximum deviations of temperature and vapor fraction. bδT = (1/n)∑ni=1|Texp − Tcal i i |, where n is the number of data c n exp cal points. δy = (1/n)∑i=1|yi − yi |,where n is the number of data points. a

E



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Article

AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected]. *E-mail: [email protected]. ORCID

Chunjian Xu: 0000-0002-2263-144X Notes

The authors declare no competing financial interest.

■

Figure 6. Comparison of system TBA + TBAc vapor−liquid equilibrium results, with and without chlorobenzene. (●) Experimental data with chlorobenzene; solid lines calculated by the NRTL model;and (−○−) experimental data without chlorobenzene.8

system, was controlled at 0.50 mass fraction, the gap regions between vapor and liquid obviously become larger.

4. CONCLUSIONS Isobaric VLE data for binary systems tert-butanol(1) + chlorobenzene(3) and tert-butyl acetate(2) + chlorobenzene(3) and ternary system tert-butanol (1) + tert-butyl acetate (2) + chlorobenzene (3) were determined at a pressure of 101.33 kPa. The data of binary systems passed the thermodynamic consistency test of the Herington method and the Van Ness point test, and the experimental data of the ternary system also passed the Wisniak consistency test. The Wilson, NRTL, and UNIQUAC activity coefficient models were chosen to associate the binary equilibrium values. The deviations of y1 and T between the model values and the experimental data were below 0.012 and 0.62 K, and the obtained binary interaction parameters were used to predict the ternary VLE values. The rmsd of vapor and the temperature between the experimental and predicted values for the ternary system were smaller than 0.0304 and 0.81 K, respectively. Both binary regression values and ternary prediction values were rationally fit to the measured results. By adding chlorobenzene as the solvent at a mass fraction of 0.50, the relative volatility between tert-butanol and tert-butyl acetate changed significantly. Thus, chlorobenzene is applicable as an extractive agent for the binary mixture. The experimental and fitting VLE data obtained are indispensable to the engineering design of the extractive distillation column.

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REFERENCES

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.7b01021. Data evaluation of relative volatilities. Literature comparison for the tert-butanol + chlorobenzene system. (PDF) F



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