Separation of azeotropic mixture (2, 2, 3, 3-Tetrafluoro-1-propanol + water) by extractive distillation: Entrainers selection and vapour-liquid equilibrium measurements

Separation of azeotropic mixture (2, 2, 3, 3-Tetrafluoro-1-propanol + water) by extractive distillation: Entrainers selection and vapour-liquid equilibrium measurements

J. Chem. Thermodynamics 138 (2019) 205–210 Contents lists available at ScienceDirect J. Chem. Thermodynamics journal homepage: www.elsevier.com/loca...

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J. Chem. Thermodynamics 138 (2019) 205–210

Contents lists available at ScienceDirect

J. Chem. Thermodynamics journal homepage: www.elsevier.com/locate/jct

Separation of azeotropic mixture (2, 2, 3, 3-Tetrafluoro-1-propanol + water) by extractive distillation: Entrainers selection and vapour-liquid equilibrium measurements Rui Li a, Xianglin Meng a, Xiaowei Liu a, Jun Gao a, Dongmei Xu a,⇑, Yinglong Wang b a b

College of Chemical and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590, China College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China

a r t i c l e

i n f o

Article history: Received 8 May 2019 Received in revised form 19 June 2019 Accepted 20 June 2019 Available online 22 June 2019 Keywords: Vapour-liquid equilibrium 2, 2, 3, 3-Tetrafluoro-1-propanol Azeotrope Extractive distillation COSMO-SAC model

a b s t r a c t For separating the azeotrope of 2, 2, 3, 3-tetrafluoro-1-propanol (TFP) and water by extractive distillation, N-methyl pyrrolidone (NMP), N-methyl formamide (NMF) and N, N-dimethyl formamide (DMF) were selected as entrainers using the COSMO-SAC model based on solvent capacity. And the charge density surface of entrainers and each component in the azeotrope system were calculated. The vapour-liquid equilibrium (VLE) data for the mixtures (TFP + NMP), (TFP + NMF) and (TFP + DMF) were measured by a modified Rose-type recirculating still at the pressure 101.3 kPa. The thermodynamic consistency for the VLE data was validated using the Herington and van Ness methods. The VLE data were correlated with NRTL, Wilson and UNIQUAC models, and the interaction parameters of thermodynamic models were fitted. Meanwhile, the effect of the entrainers on the VLE for TFP and water was explored. Compared with NMF and DMF, NMP was adopted as the suitable entrainer for separation of the azeotropic mixture TFP and water by extractive distillation. Ó 2019 Elsevier Ltd.

1. Introduction 2,2,3,3-Tetrafluoro-1-propanol (TFP) is usually utilized in preparation of coatings and pesticide [1], and can be used as a cleaning solvent [2]. During the production and application of TFP, a mixture of TFP and water is usually obtained. However, TFP and water can form an azeotropic mixture with the composition of TFP 72.5 (wt%) and water 27.5 (wt%) at temperature of 365.65 K [3], which is difficult to recover TFP by ordinary distillation. Usually, in order to separate the azeotropic mixtures, special distillation technologies are applied, such as extractive distillation [4–7], azeotropic distillation [8] and pressure swing distillation [9,10]. In this work, for separating TFP and water, the extractive distillation was adopted. Based on solvent capacity [11], the potential entrainers N-methyl pyrrolidone (NMP), N-methyl formamide (NMF) and N, N-dimethyl formamide (DMF) were selected using the conductor-like screening segment activity coefficient (COSMO-SAC) model [12]. For separation the azeotrope TFP and water by extractive distillation, the vapour-liquid equilibrium (VLE) data for the mixtures TFP and entrainers are required. Until now, few literatures have reported the VLE data for the systems contained TFP. Gao et al. ⇑ Corresponding author. E-mail address: [email protected] (D. Xu). https://doi.org/10.1016/j.jct.2019.06.026 0021-9614/Ó 2019 Elsevier Ltd.

[13] reported the VLE data for the system TFP + 2,2,3,3,4,4,5,5octafluoro- 1-pentanol at different pressure. Shi et al. [14] reported the VLE data for all the mixtures (TFP + water), (TFP + chloroform) and (TFP + p-xylene). For all the three binary mixtures (TFP + NMP), (TFP + NMF) and (TFP + DMF), the isobaric VLE data have not been retrieved from the NIST database. Therefore, the VLE data for all three mixtures (TFP + NMP), (TFP + NMF), and (TFP + DMF) were determined at pressure 101.3 kPa using a recirculating type equilibrium still. The consistency test of Herington and van Ness methods were employed to check the thermodynamic consistency for the measured VLE data. Meanwhile, the NRTL [15], Wilson [16] and UNIQUAC [17] models were used to correlate the measured VLE data. Accordingly, the corresponding interaction parameters for all the three models were correlated. And based on the regressed parameters of the UNIQUAC model, the effect of the entrainers on the VLE for the azeotrope TFP + water were explored by the Flash 2 module in Aspen Plus [18].

2. Entrainers selection 2.1. Solvent capacity For selection of the entrainers, solvent capacity (SP) was applied [19], which is defined as follows:

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SP ¼

R. Li et al. / J. Chem. Thermodynamics 138 (2019) 205–210

1

ð1Þ

c1 AC

where c1 AC is the infinite activity coefficient of component TFP in entrainer C. To calculate the infinite dilution activity coefficient, the COSMO-SAC model was employed [20,21]. The detailed computation steps can be found in the previous work [22–24]. The calculated results of SP are presented in Fig. 1, As shown in Fig. 1, the order of the solvent capacity for the entrainers is as follows: NMP > DMF > NMF > ethanolamine > EG > cyclohexanol > cyclohexanone > furfuralcohol > isoamyl acetate > sulfolane > paraxylene. Thus, NMP, NMF and DMF were chosen as the potential entrainer for the separation of TFP and water by extractive distillation. 2.2. Interaction analysis To explore the interactions among the entrainers, TFP and water, the surface charge density (r-profiles) was obtained by the COSMO-SAC model for the entrainers, TFP and water. The calculated results of r-profiles for NMP, DMF, NMF, TFP and water are plotted in Fig. 2. From Fig. 2, the peaks for TFP and water appear in the ‘‘Hydrogen bond acceptor” area and ‘‘Hydrogen bond donator”

area, which indicates that TFP and water not only have the hydrogen bond acceptor ability, but also have the hydrogen bond donator ability. TFP has strong hydrogen bond donator ability compared to water, since the cut off values of TFP is away from 0.0084 (e/Å2). Therefore, TFP is more likely to form hydrogen bonds with the entrainers, which implies that water is more volatile after the addition of the entrainers. Also as shown in Fig. 2, the peaks of the three entrainers are mainly located in ‘‘Hydrogen acceptor zone” area, which implies that the entrainers have stronger hydrogen bond acceptor ability. In the meantime, the cut off values of NMP is further away from 0.0084  1016 ecm2 compared to DMF and NMF, which indicates that NMP has the strongest hydrogen bond acceptor ability than the others. Thus, TFP and NMP can have the strongest hydrogen bond interaction, followed by DMF and NMF, which implies that NMP has the best separation performance [25]. 3. Experimental 3.1. Materials The chemicals TFP, NMP, NMF and DMF were commercial grade. The information of all the chemicals is presented in Table 1, including the CAS No., suppliers, mass fraction, and boiling temperature. The purities of the chemicals were checked by gas chromatography (GC). 3.2. Equilibrium measurements The modified Rose-type recirculating still was employed to determine the VLE data, where a manometer assembly with an accuracy of ±0.1 kPa was connected to the system to measure the equilibrium pressure. A mercury thermometer with an accuracy of ±0.1 K was employed to measure the equilibrium temperature. The details of the still and validation of the apparatus were described in our previous work, respectively [13,37]. To reach the equilibrium state, the recirculation time for the two phases was maintained for over 50 min at a constant temperature. Then the equilibrium temperature was recorded and the samples of 0.2 mL for the vapour and liquid phases were withdrawn by syringes respectively. The sample compositions were analysed by GC.

Fig. 1. Solvent capacity of entrainers calculated by the COSMO-SAC model at T = 298.15 K.

3.3. Analysis Compositions of the (TFP + NMP), (TFP + NMF) and (TFP + DMF) systems were analysed using Gas chromatograph (SP6890, Shandong Rui Hong Chemical Co., Ltd.) with a packed column and a thermal conductivity detector (TCD). The hydrogen was employed as carrier gas with high purity (99.999 wt%). The analysis conditions are listed in Table 2. Area corrected normalization method was applied to calibrate the peak areas of GC by five standard samples with known compositions before analysing the samples. The five standard samples were prepared using an electronic analytical balance (Ohaus AR124CN) with an accuracy of ±0.0001 g. The samples were analysed at least three paralleled analyses, and the mean value was recorded. 4. Results and discussions 4.1. Experimental results

Fig. 2. r-profiles for NMF, NMP, DMF, TFP, water.

The VLE data for the binary mixtures (TFP + NMP), (TFP + NMF) and (TFP + DMF) were measured at 101.3 kPa, which is presented

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R. Li et al. / J. Chem. Thermodynamics 138 (2019) 205–210 Table 1 Materials description.

a b

Tb/Kb

Name

CAS No.

Supplier

Mass fraction

Analysis method

This work

Literature

TFP NMP

76-37-9 872-50-4

Shandong Fluoro Technology Co., Ltd. Tianjin Guangfu Fine Chemical Research Institute

0.996 0.990

381.95 476.05

NMF

123-39-7

Chengdu Cologne Chemical Co., Ltd.

0.995

471.20

DMF

68-12-2

Chengdu Cologne Chemical Co., Ltd.

0.995

426.05

382.15 477.01 476.50 475.63 472.25 472.66 425.10 425.67 426.34

[14,26,27,28] [29] [30] [31] [32] [33] [34] [35] [36]

GCa GCa

GCa GCa

Gas chromatograph. The boiling temperatures (Tb) were measured at 101.3 kPa, the standard uncertainties u of p and T are u(T) = 0.35 K, u(p) = 0.35 kPa.

Table 2 Operating conditions for gas chromatograph.

Table 4 Experimental isobaric VLE data for liquid phase mole fraction x, vapour phase mole fraction y, activity coefficient c for the binary system of TFP (1) + NMF (2) at 101.3 kPa.a

Name

Characteristic

Description

Column

Type Temperature Type Flow rate Pressure Injection volume Temperature Type Temperature

PorapaQ, 3 mm  2 m 463.15 K Hydrogen 30 mL∙min1 0.3 MPa 0.3 lL 483.15 K Thermal conductivity detector (TCD) 483.15 K

Carrier gas

Injector Detector

in Tables 3–5 and the graphically for all the three binary mixtures are shown in Figs. 3–5. The vapour-liquid relationship is presented by the following equation:

  L s  ^ y p ¼ xi c /s ps exp v i p  pi / i i i i i RT

ð2Þ

T/K

x1

y1

c1

c2

471.20 467.35 459.95 451.55 445.70 439.20 432.25 426.65 420.95 414.15 408.05 401.95 400.15 393.15 387.85 381.95

0.0000 0.0103 0.0369 0.0726 0.1009 0.1365 0.1812 0.2248 0.2758 0.3476 0.4271 0.5225 0.5541 0.6989 0.8348 1.0000

0.0000 0.0930 0.2842 0.4613 0.5626 0.6560 0.7387 0.7920 0.8398 0.8863 0.9201 0.9471 0.9538 0.9764 0.9895 1.0000

– 1.0605 1.0466 1.0358 1.0332 1.0315 1.0297 1.0192 1.0158 1.0145 1.0099 1.0072 1.0055 1.0034 1.0004 –

– 1.0002 1.0003 1.0005 1.0007 1.0041 1.0069 1.0206 1.0235 1.0269 1.0287 1.0310 1.0323 1.0351 1.0456 –

a Standard uncertainties u are u(T) = 0.35 K, u(p) = 0.35 kPa, u(x) = 0.0058, u(y) = 0.0068.

Since the VLE measurement was performed at pressure 101.3 kPa, the vapour phase can be assumed as ideal gas, Eq. (2) can be simplified as follows [38]:

yi p ¼xi ci psi

ð3Þ

Table 3 Experimental isobaric VLE data for liquid phase mole fraction x, vapour phase mole fraction y, activity coefficient c for the binary system of TFP (1) + NMP (2) at 101.3 kPa.a T/K

x1

y1

c1

c2

476.05 468.95 463.55 457.25 451.75 445.75 440.60 434.45 428.50 422.20 416.50 410.25 404.45 398.85 392.95 387.00 384.75 381.95

0.0000 0.0200 0.0350 0.0550 0.0750 0.0998 0.1253 0.1600 0.2035 0.2535 0.3067 0.3835 0.4642 0.5565 0.6898 0.8435 0.9214 1.0000

0.0000 0.2005 0.3146 0.4320 0.5215 0.6065 0.6707 0.7371 0.7908 0.8396 0.8764 0.9110 0.9367 0.9572 0.9758 0.9903 0.9954 1.0000

– 1.1405 1.1397 1.1343 1.1285 1.1249 1.1153 1.1044 1.0744 1.0705 1.0600 1.0489 1.0450 1.0446 1.0221 1.0174 1.0045 –

– 1.0064 1.0067 1.0068 1.0070 1.0076 1.0077 1.0107 1.0159 1.0168 1.0189 1.0257 1.0261 1.0277 1.0430 1.0475 1.0832 –

a Standard uncertainties u are u(T) = 0.35 K, u(p) = 0.35 kPa, u(x) = 0.0079, u(y) = 0.0085.

Table 5 Experimental isobaric VLE data for liquid phase mole fraction x, vapour phase mole fraction y, activity coefficient c for the binary system of TFP (1) + DMF (2) at 101.3 kPa.a T/K

x1

y1

c1

c2

426.05 423.20 420.65 417.95 414.65 411.75 408.70 405.45 402.80 399.45 396.30 393.25 390.45 387.35 384.55 381.95

0.0000 0.0153 0.0473 0.0783 0.1232 0.1697 0.2303 0.2929 0.3482 0.4261 0.5074 0.5948 0.6907 0.8001 0.9102 1.0000

0.0000 0.0809 0.1709 0.2559 0.3549 0.4374 0.5174 0.5964 0.6556 0.7264 0.7864 0.8403 0.8868 0.9338 0.9728 1.0000

– 1.6666 1.2146 1.1774 1.1311 1.0931 1.0347 1.0255 1.0214 1.0175 1.0138 1.0116 1.0004 1.0004 1.0001 –

– 1.0049 1.0050 1.0051 1.0059 1.0072 1.0192 1.0223 1.0257 1.0263 1.0308 1.0332 1.0511 1.0542 1.0599 –

a Standard uncertainties u are u(T) = 0.35 K, u(p) = 0.35 kPa, u(x) = 0.0063, u(y) = 0.0067.

where the saturation vapour pressure (psi ) of pure component i at equilibrium temperature as calculated form the Wagner 25 equation [39], which is expressed as:

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R. Li et al. / J. Chem. Thermodynamics 138 (2019) 205–210

  C1i ð1-Tri ÞþC2i ð1-Tri Þ1:5 þC3i ð1-Tri Þ2:5 þC4i ð1-Tri Þ5 ln psi ¼lnðpci Þþ Tri ð4Þ Tri ¼

T Tci

ð5Þ

The parameters of the Wagner 25 equation for each component were retrieved from the Aspen databank and are given in Table 6. With Eq. (3), the values of experimental activity coefficients for all the three binary mixtures were computed and are shown in Tables 3–5. 4.2. Thermodynamic consistency test

Fig. 3. Experimental data and calculated results for the system TFP (1) + NMP (2): d, experimental data; - - -, calculated by the NRTL model; – - –, calculated by the Wilson model; . . .. . ., calculated by the UNIQUAC model.

The consistency of the measured VLE data for three binary mixtures was validated by the Herington and van Ness methods. The Herington method [40,41] is expressed as follows:

R   1     0 lnðc1=c2Þdx1 Sþ  S   ¼ 100  R D ¼ 100   1 Sþ þ S  lnðc1=c2Þjdx1 0 j

ð6Þ

  T max  T min   J ¼ 150    T min

ð7Þ

The VLE data can be considered to thermodynamically consistent if the calculated results of |DJ| are less than 10. The van Ness method [42,43] can be described as follows:

Fig. 4. Experimental data and calculated data for the system of TFP (1) + NMF (2): d, experimental data; - - -, calculated by the NRTL model; – - –, calculated by the Wilson model; . . .. . ., calculated by the UNIQUAC model.

Dy ¼

N N   1X 1X exp  Dyi ¼ 100ycal i  yi N i¼1 N i¼1

ð8Þ

Dp ¼

  exp N N P  pcal  1 X 1X DP i ¼ 100 i exp i  N i¼1 N i¼1 pi

ð9Þ

If the values of Dy and DP are less than 1, the measured VLE data can pass the van Ness test. The results of thermodynamic consistency tests are listed Table 7. As seen from Table 7, the calculated results by the Herington and van Ness tests meet the test conditions, which implies that the measured VLE data are thermodynamically consistent. 4.3. Data regression The generated experimental VLE data for the mixtures (TFP + NMP), (TFP + NMF), and (TFP + DMF) were fitted by the NRTL, Wilson, and UNIQUAC models. The value of non-randomness parameter (aij) for NRTL model was set at 0.3 [15]. The values of the structural parameters r and q for the UNIQUAC model are given in Table 8. The interaction parameters of the three models were obtained based on the maximum likelihood method by minimizing the following objective equation: 2 3 !2  2  exp 2  exp 2 N X T exp  T cal pexp  pcal xi  xcal yi  ycal i i i i i i 4 5 Q¼ þ þ þ i¼1

rT

rp

rx

ry

ð10Þ

Fig. 5. Experimental data and calculated data for the system of TFP (1) + DMF (2): d, experimental data; - - -, calculated by the NRTL model; – - –, calculated by the Wilson model; . . .. . ., calculated by the UNIQUAC model.

The regressed corresponding interaction parameters for all the three models and the values of root-mean-square deviation (RMSD) for the mole fraction of vapour phase and the temperature are illustrated in Table 9. As seen from Table 9, the values of RMSD for y1 and T are all less than 0.21 K and 0.0094, respectively, which shows that all the three models can provide agreed results with the measured VLE data.

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R. Li et al. / J. Chem. Thermodynamics 138 (2019) 205–210 Table 6 Constants of the Wagner 25 equation.a

a

Component

CS

C2i

C3i

C4i

pci/kPa

Tci/K

Tlower/K

Tupper/K

TFP NMP NMF DMF

8.4992 8.3465 19.0097 7.3020

2.3648 2.9118 19.3880 1.0015

4.1144 3.7531 13.7923 2.1598

3.8701 2.4306 1.0120 2.3702

4131.59 4526.95 4407.22 7067.66

561.00 721.74 656.00 649.60

200.00 249.19 266.88 212.86

561.00 721.74 656.00 649.60

Taken from the Aspen plus physical properties databank [18].

Table 7 Thermodynamic consistency check. System

TFP (1) + NMP (2) TFP (1) + NMF (2) TFP (1) + DMF (2)

Herington test

4.6679 8.1609 4.0399

van Ness test

DP

Dy

0.0553 0.0106 0.0421

0.1537 0.0672 0.6595

Table 8 Structural parameters r and q for the UNIQUAC model.a

a

Component

r

q

TFP NMP NMF DMF

3.453 3.200 2.192 2.736

3.192 3.981 2.403 3.086

Taken from the Aspen plus physical properties databank [18].

Fig. 6. Effect of the entrainers on VLE of TFP and water calculated by the UNIQUAC model: – - –, TFP (1) + water (2) + NMP (3); ––, TFP (1) + water (2) + DMF(3); – – –, TFP (1) + water (2) + NMF (3); -▲-, experimental data without extractive entrainer [14].

4.4. Effect of extractive solvents To explore the effect of the selected extractive solvents, the vapour-liquid equilibrium for the system (TFP + water) with the different entrainers was calculated using the Flash 2 module in Aspen Plus by the UNIQUAC model with the regressed interaction parameters, which is shown in Fig. 6. As illustrated in Fig. 6, all the selected entrainers can eliminate the azeotropic point of the mixture TFP + water, and NMP exhibits the largest deviation from the diagonal line, which indicates that NMP has the best effect compared to DMF and NMF. Therefore, NMP is the suitable extractive solvent for separation of the azeotropic mixture TFP and water, which indicates that exerimental VLE result shows an agreement from the predicted results by COSMO-SAC model.

5. Conclusions In this work, three entrainers NMP, NMF and DMF were selected based on solvent capacity calculated by the COSMO-SAC model. Meanwhile, the interaction mechanism between entrainers and the components in the azeotroic mixture was explored by the r-profiles. Then, the isobaric VLE data for (TFP + NMP), (TFP + NMF) and (TFP + DMF) binary mixtures were determined under the pressure of 101.3 kPa by the modified Rose-type recirculating still. The Herington and van Ness methods were employed to check the thermodynamic consistency of the experimental VLE

Table 9 Regressed binary interaction parameters and root-mean-square deviations (RMSD) for the systems TFP (1) + NMP (2), TFP (1) + NMF (2), TFP (1) + DMF (2).

a

b c d e

Model

aij

aji

bij/K

bji/K

RMSD(y1)a

RMSD(T)b

TFP (1) + NMP (2) NRTLc Wilsond UNIQUACe

2.8016 1.6146 0.00876

2.2660 2.1142 0.0992

1582.95 876.237 50.5351

1218.71 1234.71 13.9362

0.0013 0.0013 0.0021

0.14 0.14 0.21

TFP (1) + NMF (2) NRTL Wilson UNIQUAC

5.3505 5.379 2.4012

8.8519 3.0437 3.5701

1869.80 1855.57 833.21

3155.92 10327.56 1247.10

0.0017 0.0019 0.0018

0.07 0.07 0.10

TFP (1) + DMF (2) NRTL Wilson UNIQUAC

11.9015 19.0495 5.0036

27.2667 6.2563 10.9229

4347.34 7035.77 1755.16

10185.70 2215.27 3972.84

0.0094 0.0079 0.0091

0.18 0.15 0.17

rffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffi 2 PN ðyexp ycal Þ i i RMSD(y1) = . i¼1 N rffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffi 2 exp cal PN ðT i T i Þ . RMSD(T) = i¼1 N NRTL, sij = aij + bij/T, the value of aij was set at 0.3. Wilson, lnA ij = aij + bij/T. UNIQUAC, sij = exp(aij + bij/T).

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data, respectively. And the validation results showed that the measured VLE data for the mixtures passed the consistent tests. The thermodynamic models NRTL, Wilson, and UNIQUAC were adopted to fit the measured VLE data for the three mixtures and the binary interaction parameters of the three models were obtained. The RMSD values for the mole fraction of vapour phase and the temperature were less than 0.21 K and 0.0094, respectively. The effect of the extractive solvents NMP, DMF and NMF on the VLE of the azeotropic mixture TFP and water was explored by the UNIQUAC model with the regressed binary interaction parameters. The calculated results showed that NMP is the appropriate extractive solvent to separate the azeotrope TFP and water by extractive distillation. Acknowledgements This work was supported by Shandong Provincial Key Research & Development Project (2018GGX107001), National Natural Science Foundation of China (21878178) and Project of Shandong Province Higher Educational Science and Technology Program (J18KA072). Declaration of Competing Interest The authors declare no competing financial interest. References [1] P. Hurtel, Process for the Preparation of Fluorinated Alkyl(meth) - Acrylates, EP Patent 0206899, 1986. [2] D. Bonnet-Delpon, J.-P. Bégué, B. Crousse, Fluorinated alcohols: a new medium for selective and clean reaCtion, Synlett (2004) 18–29. [3] K.T.Y. Fumihiko, Method for recovering fluoroalcohol, US Patent, 2001. [4] Y. Hu, Y. Su, S. Jin, I.L. Chien, W. Shen, Systematic approach for screening organic and ionic liquid solvents in homogeneous extractive distillation exemplified by the tert-butanol dehydration, Sep. Purif. Technol. 211 (2019) 723–737. [5] W. Shen, L. Dong, S.a. Wei, J. Li, H. Benyounes, X. You, V. Gerbaud, Systematic design of an extractive distillation for maximum-boiling azeotropes with heavy entrainers, AIChE J. 61 (2015) 3898–3910. [6] A. Yang, R. Wei, S. Sun, S.a. Wei, W. Shen, I.L. Chien, Energy-saving optimal design and effective control of heat integration-extractive dividing wall column for separating heterogeneous mixture methanol/toluene/water with multiazeotropes, Ind. Eng. Chem. Res. 57 (2018) 8036–8056. [7] A. Yang, H. Zou, I.L. Chien, D. Wang, S.a. Wei, J. Ren, W. Shen, Optimal design and effective control of triple-column extractive distillation for separating ethyl acetate/ethanol/water with multiazeotrope, Ind. Eng. Chem. Res. 58 (2019) 7265–7283. [8] N. Bekiaris, G.A. Meski, C.M. Radu, M. Morari, Multiple steady states in homogeneous azeotropic distillation, Ind. Eng. Chem. Res. 32 (1993) 2023– 2038. [9] J.P. Knapp, M.F. Doherty, A new pressure-swing-distillation process for separating homogeneous azeotropic mixtures, Ind. Eng. Chem. Res. 31 (1992) 346–357. [10] A. Yang, W. Shen, S.a. Wei, L. Dong, J. Li, V. Gerbaud, Design and control of pressure-swing distillation for separating ternary systems with three binary minimum azeotropes, AIChE J. 65 (2019) 1281–1293. [11] Y. Dong, C. Dai, Z. Lei, Extractive distillation of methylal/methanol mixture using ethylene glycol as entrainer, Fluid Phase Equilibr. 462 (2018) 172–180. [12] R. Fingerhut, W.-L. Chen, A. Schedemann, W. Cordes, J. Rarey, C.-M. Hsieh, J. Vrabec, S.-T. Lin, Comprehensive assessment of COSMO-SAC models for predictions of fluid-phase equilibria, Ind. Eng. Chem. Res. 56 (2017) 9868– 9884. [13] J. Gao, L. Zhao, L. Zhang, D. Xu, Z. Zhang, Isobaric vapour-liquid equilibrium for binary systems of 2,2,3,3-tetrafluoro-1-propanol + 2,2,3,3,4,4,5,5-Octafluoro1-pentanol at 53.3, 66.7, 80.0 kPa, J. Chem. Eng. Data 61 (2016) 3371–3376. [14] P. Shi, Y. Gao, J. Wu, D. Xu, J. Gao, X. Ma, Y. Wang, Separation of azeotrope (2,2,3,3-tetrafluoro-1-propanol + water): isobaric vapour-liquid phase equilibrium measurements and azeotropic distillation, J. Chem. Thermodyn. 115 (2017) 19–26. [15] H. Renon, J.M. Prausnitz, Local compositions in thermodynamic excess functions for liquid mixtures, AlChE J. 14 (1968) 135–144. [16] G.M. Wilson, A new expression for the excess free energy of mixing, J. Am. Chem. Soc 86 (1964) 127–130. [17] D.S. Abrams, J.M. Prausnitze, Statistical thermodynamics of liquid mixtures: a new p txpression for the excess gibbs energy of partly or completely miscible systems, AIChE J. 21 (1975) 116–128. [18] Aspen Plus Software, Version 8.4, Aspen Technology, Inc., Burlington, MA, 2013.

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JCT 2019-395