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Liquid−Liquid Equilibria for the Ternary System n‑Butyl Acetate + Pyrocatechol + Water at Different Temperatures at 101.3 kPa Baohe Wang, Mingjie Rong, Pinpin Wang, and Shuang Chen* Key Laboratory for Green Chemical Technology of Ministry of Education, Research and Development Center of Petrochemical Technology, Tianjin University, Tianjin 300072, People’s Republic of China S Supporting Information *

ABSTRACT: Liquid−liquid equilibria (LLE) data for the ternary system of n-butyl acetate + pyrocatechol + water were measured at 101.3 kPa over the temperature range of 298.15−318.15 K. Phase diagrams were obtained by determining the tie-line data. The LLE experimental data for the system were correlated with the nonrandom two-liquid (NRTL) and universal quasichemical (UNIQUAC) models. The average root-mean-square deviations (RMSD) of the NRTL and UNIQUAC models were 0.0114 and 0.0200. Both models correlated the experimental tie-line data successfully, while the correlation of the UNIQUAC model was inferior to that of the NRTL model.

1. INTRODUCTION Wastewater from many industrial process like coal gasification, petroleum refining, and petrochemical manufacture contains various kinds of phenols, which are considered to be toxic and difficult to deal with.1,2 Of all these various phenols, the concentrations of dihydric and trihydic phenols are very high, usually hundreds or even thousands of milligrams per liter.3 Thus, they should be the prevailing concern in the process of phenolic extraction. Pyrocatechol, of interest in our study, is one kind of the dihydric phenols. Due to the strong binding force between the two hydroxyl groups of pyrocatechol and water molecules, it becomes more difficult to be removed from water. According to the study of Hong et al.,4 solvent extraction is a desirable method to treat phenolic wastewater of high concentrations. The selection of appropriate solvents for extraction plays a key role in the extracting process. For common phenolic compounds in wastewater, many solvents like alcohols, ethers, ketones, esters, and so forth had been reported to extract them. For alcohols, Oliveira et al.5 reported the LLE data for ternary systems of phenol + water + 1-butanol, 2-butanol, and tert-butanol. Lin et al.6 reported the extraction behaviors of phenol in dilute solution by 1-octanol. It shows that the solubility of the alcohols with a low boiling point in water is high, which will increase the loss of solvent. However, the energy consumption of alcohols with high boiling points will be large in the solvents’ recovery process. For ethers, Lei et al.7 applied 2-methoxy-2-methylpropane for the extraction of phenol and reported liquid−liquid equilibria data for 2methoxy-2-methylpropane + phenol + water. It was found that the extraction effect of ethers for phenol was excellent, but according to Huang et al.,8 the extraction effect was poor in © XXXX American Chemical Society

extracting dihydric and trihydic phenols. Ketones have been used as the solvent in recent years. Chen et al.9 used methyl butyl ketone to separate phenol and hydroquinone from water, respectively, and measured phase equilibrium data for methyl butyl ketone + phenol or hydroquinone + water. Yang et al.10 chose methyl isobutyl ketone to extract both phenol and hydroquinone from water and studied the quaternary system of methyl isobutyl ketone + phenol + hydroquinone + water. But the high price limits their use. On the basis of the research of Gonzalez et al.11 and Pinto et al.,12 esters are supposed to be the preferable solvent for the recovery of phenol from water since they have a higher selectivity ratio and distribution coefficient. Narasimhan et al.13 reported the LLE date of the phenol−water−n-butyl acetate system at 303.15 K. Schuberth et al.14 reported the LLE data for the same system at 317.55 K. However, with respect to systems of n-butyl acetate + dihydric phenols + water, no literature was found. To design a proper solvent extraction equipment and calculate the thermodynamic limit of a given separation, the reliable liquid−liquid phase equilibria data are necessary.15,16 In this work, the LLE data for the system of n-butyl acetate + pyrocatechol + water at 101.3 kPa were measured at the temperature range from 298.15 to 318.15 K. Since this work is concentrated on extracting pyrocatechol from industrial wastewater by n-butyl acetate solvent, the corresponding equilibrium data are exclusively determined in a small zone of the ternary system. To evaluate the extraction behaviors of nbutyl acetate, the distribution coefficients and separation factors Received: April 1, 2016 Accepted: August 1, 2016

A

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Table 1. Physical Properties of the Chemicals at 101.3 kPa chemical methanol pyrocatechol n-butyl acetate a

property

exp. value

lit. value

density, ρa (298.15 K)/(g·cm−3) refractive index, nDa (298.15 K) density, ρa (298.15 K)/(g·cm−3) melting point, Tma (101.3 kPa)/(K) density, ρa (298.15 K)/(g·cm−3) refractive index, nDa (298.15 K)

0.78614 1.3264 1.34602 379.25 0.87312 1.3930

0.786317 1.326717 1.34618 378.8518 0.875319 1.393419

Standard uncertainties u are u(p) = 0.35 kPa, u(T) = 0.01 K, u(ρ) = 0.001 g·cm−3, u(nD) = 0.0001, and u(Tm) = 0.8 K.

Table 2. Experimental LLE Data for Ternary System n-Butyl Acetate (1) + Pyrocatechol (2) + Water (3) at T = 298.15, 308.15, and 318.15 K and 101.3 kPaa organic phase T(K)

W1O

W2

298.15

0.9016 0.7996 0.7492 0.6820 0.6602 0.6197 0.5359 0.4436 0.3621 0.2824 0.2412 0.8954 0.8147 0.7544 0.7011 0.6523 0.6024 0.5897 0.5153 0.4638 0.3933 0.3532 0.9133 0.8179 0.6874 0.6631 0.5318 0.4735 0.4151 0.3597 0.3193 0.2811

0.0840 0.1573 0.2011 0.2597 0.2744 0.3096 0.3688 0.4021 0.4450 0.4613 0.4580 0.0753 0.1524 0.2031 0.2439 0.2853 0.3235 0.3310 0.3845 0.4068 0.4255 0.4284 0.0620 0.1511 0.2589 0.2747 0.3747 0.3972 0.4121 0.4218 0.4219 0.4184

308.15

318.15

O

aqueous phase W3O

W1W

W2W

W3W

D

S

0.0144 0.0431 0.0497 0.0583 0.0654 0.0707 0.0953 0.1543 0.1929 0.2563 0.3008 0.0293 0.0329 0.0425 0.0550 0.0624 0.0741 0.0793 0.1002 0.1294 0.1812 0.2184 0.0247 0.0310 0.0537 0.0622 0.0935 0.1293 0.1728 0.2185 0.2588 0.3005

0.0092 0.0076 0.0083 0.0072 0.0074 0.0081 0.0086 0.0119 0.0135 0.0249 0.0317 0.0063 0.0072 0.0081 0.0070 0.0071 0.0084 0.0078 0.0093 0.0112 0.0148 0.0236 0.0063 0.0086 0.0079 0.0080 0.0100 0.0126 0.0191 0.0304 0.0316 0.0360

0.0033 0.0116 0.0214 0.0350 0.0385 0.0557 0.0836 0.1276 0.1881 0.2040 0.2303 0.0033 0.0132 0.0229 0.0381 0.0442 0.0684 0.0781 0.1095 0.1320 0.1597 0.1842 0.0040 0.0160 0.0423 0.0516 0.1126 0.1419 0.1724 0.1971 0.2138 0.2336

0.9875 0.9808 0.9703 0.9578 0.9541 0.9362 0.9078 0.8605 0.7984 0.7711 0.7380 0.9904 0.9796 0.9690 0.9549 0.9487 0.9232 0.9141 0.8812 0.8568 0.8255 0.7922 0.9897 0.9754 0.9498 0.9404 0.8774 0.8455 0.8085 0.7725 0.7546 0.7304

25.45 13.56 9.397 7.420 7.127 5.558 4.411 3.151 2.366 2.261 1.989 22.82 11.55 8.869 6.402 6.455 4.730 4.238 3.511 3.082 2.664 2.326 15.50 9.444 6.121 5.324 3.328 2.799 2.390 2.140 1.973 1.791

1746 308.6 183.5 121.9 104.0 73.60 42.02 17.57 9.792 6.803 4.879 771.3 343.8 202.2 111.1 98.13 58.92 48.85 30.88 20.41 12.14 8.436 621.1 297.12 108.3 80.49 31.23 18.30 11.18 7.566 5.754 4.353

a

All compositions are expressed as mass fraction; the standard uncertainties u are u(p) = 0.35 kPa, u(T) = 0.12 K, u(W1O) = u(W2O) = u(W1W) = u(W2W) = 0.0031, u(W3W) = 0.0042, u(W3O) = 0.0033, u(D) = 0.264, and u(S) = 2.06.

purity of all of the chemicals were higher than 0.990. All reagents were used without any further purification, and deionized and bidistilled water was used throughout all experiments. The densities (ρ), refractive indexes (nD), and the melting points (Tm) of the chemicals were determined in this work. The densities were measured using an Anton Paar DMA-58 densimeter at 298.15 ± 0.01 K. The refractive indexes were measured by ATAGO NAR-3T Abbe refractmeter at 298.15 ± 0.01 K. The accuracies of the densimeter and the refractometer are 0.00001 g·cm−3 and 0.0001, respectively. The melting point was determined at 101.3 ± 0.35 kPa. All of the

were determined from the tie-line data. The NRTL and UNIQUAC activity coefficient models were employed to correlate the experimental data, and the values of the interaction parameters were obtained.

2. MATERIALS AND METHODS 2.1. Materials. Methanol and pyrocatechol were supplied by Tianjin Guangfu Fine Chemical Research Institute. n-Butyl acetate was purchased from Tianjin Yuanli Chemical Co. Ltd. The purity of the chemical reagents was confirmed by gas chromatography, and the results were listed in the Supporting Information (SI Table 1), which showed that the mass fraction B

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physical properties of the chemicals are given in Table 1 along with literature values. 2.2. Apparatus and Procedure. The liquid−liquid equilibrium experiments of the ternary n-butyl acetate + pyrocatechol + water system were carried out in an equilibrium device.20 The experimental device was made up of four parts: a 250 mL jacketed glass vessel, a thermostatic water bath, a magnetic stirring apparatus, and a mercury thermometer accurate to 0.1 K. The temperature of the equilibria still was kept at a certain value by the circulating water pumped from the thermostatic water bath in the jacket. During the experiment, deionized water, n-butyl acetate, and pyrocatechol were put into the vessel. The mass of these three compounds was measured by an analytical balance accurate to 0.0001 g. Then the temperature of the still was set by adjusted the temperature of the circulating water. The prepared mixtures were agitated vigorously for 3 h to mix the compounds sufficiently and stood for 12 h to separate the aqueous phase and the organic phase completely. After the mixtures were divided into two liquid phases, the samples of both phases were taken out by a syringe and put into sample bottles, respectively. The compositions of the n-butyl acetate and pyrocatechol in both organic and aqueous phases were analyzed by a gas chromatograph (Agilent 6820) equipped with a flame ionization detector (FID) and a HP-5 capillary column (30 m long, 0.32 mm i.d., 0.5 μm film thickness). The temperatures of the detector and injection port were 573.15 K, and the temperature of the oven was kept at 423.15 K. Nitrogen was used as a carrier at a rate of 7.9 mL/ min. The contents of n-butyl acetate and pyrocatechol were accurately quantified through internal standard, and methanol was chosen as the internal standard for the good solubility properties. The water composition in aqueous phase was calculated by normalization method. As the water content in organic phase was too small, calculation by the normalization method may be imprecise, so the Karl Fischer titrator was used to measure them. The accuracy of Karl Fischer titrator was 0.1 μg. The process of sampling analysis was repeated at least three times, and the average value was used. The reliability of the experimental device has been tested in our previous work.21

Table 4. Temperature-Dependent Coefficients in the Binary Interaction Parameters of NRTL and UNIQUAC Models for the System n-Butyl Acetate (1) + Pyrocatechol (2) + Water (3)a parameters NRTL

UNIQUAC

a

a

ri

qi

3.9156 4.8274 0.9200

2.9600 4.1960 1.4000

(K) (K)

T (K)

NRTL

UNIQUAC

0.0095 0.0094 0.0154 0.0114

0.0191 0.0154 0.0255 0.0200

(W2/W3)O (W2/W3)W

(2)

where superscripts O and W mean the organic solvent phase and aqueous phase, respectively. W2 is the mass fraction of pyrocatechol, and W3 is that of water. The distribution coefficient and the selectivity are shown in Table 2. The high distribution coefficient suggests that a small amount of extractive solvent can achieve a good extraction effect, which means low costs considering the size of equipment and the energy to separate solvent and solute. The value of the selectivity factor is a direct reflection of the extracting capability of n-butyl acetate. The selectivity factor values are quite high, indicating that n-butyl acetate is a promising extraction solvent for pyrocatechol. 3.2. Data Correlation. The nonrandom two-liquid (NRTL)22 and universal quasichemical (UNIQUAC)23 thermodynamic models are widely used methods for a nonideal system of the multicomponent liquid mixtures and were applied to correlate the experimental liquid−liquid phase equilibrium data. The NRTL model is embedded in Aspen Plus in the following form: ln γi =

∑j χj τjiGji ∑k χk Gki

+

∑ j

χj Gij ⎛ ∑ χ τmjGmj ⎞ ⎜⎜τij − m m ⎟⎟ ∑k χk Gki ⎠ ∑k χk Gkj ⎝ (3)

where χ is the mole fraction, τ and G are binary parameters for NRTL model, and i, j, k, and m are indices. The binary interaction parameters can be calculated using the following equations.

318.15 K are listed in Table 2. All of the concentrations are represented by mass fraction. The distribution coefficient (D) and the selectivity factor (S) are calculated in order to estimate the ability of n-butyl acetate to remove pyrocatechol from water, the distribution coefficient (D), and the selectivity factor (S) are calculated by the following equations: W 2O W2W

2−3 5.0501 −9.2310 −1924.2453 3816.6094 0.3 12.9944 −9.7804 −4143.0353 3406.5006

298.15 308.15 318.15 average

Taken from the Aspen Plus V 7.2 physical properties data bank.

D=

1−3 −0.3807 9.3991 808.6219 −1153.4586 0.3 7.7880 −2.0635 −3044.6373 530.0614

α is fixed to 0.3.26

S=

Table 3. UNIQUAC Structural Parameters of the Pure Componenta component

(K) (K)

1−2 1.4462 −0.3048 4094.2854 −664.6238 0.3 −3.8249 −0.2622 849.5182 516.2644

Table 5. RMSD Values for the Studied System

3. RESULTS AND DISCUSSION 3.1. LLE Experimental Data. The LLE data for the n-butyl acetate + pyrocatechol + water system at 298.15, 308.15, and

pyrocatechol n-butyl acetate water

aij aji bij bji α aij aji bij bji

(1) C

Gij = exp( −αijτij)

(4)

τij = aij + bij /T

(5)

αij = αji = cij

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Figure 2. Distribution coefficients of pyrocatechol plotted versus mass fraction of pyrocatechol in the organic phase at 298.15 K. ■, experimental data; ○, the NRTL model; △, the UNIQUAC model.

Figure 3. Selectivity coefficients plotted versus the mass fraction of pyrocatechol in the organic phase at 298.15 K. ■, experimental data; ○, the NRTL model; △, the UNIQUAC model.

ln γi = ln γiC(combinatorial) + ln γi R (residual)

(7)

where the combinatorial and residual terms of the activity coefficient are due to the difference in shape and energy of the molecules, respectively. These terms can be given as

Figure 1. LLE data for the ternary system n-butyl acetate (1) + pyrocatechol (2) + water (3): (a) at 298.15 K; (b) at 308.15 K; (c) at 318.15 K. ■ and solid line, experimental data; ○ and dashed line, the NRTL model; ● and dot line, the UNIQUAC model.

ln γiC = ln

ϕi χi

+

ϕ θ Z qi ln i + li − i 2 ϕi χi

⎡ c ln γi = qi⎢1 − ln(∑ θτ j ji) − ⎢ j=1 ⎣

where a is the nonrandom parameter and aij, bij, and cij are NRTL coefficients of the equations for binary interaction parameters. The binary interaction parameters can be obtained from LLE data regression using Aspen Plus V7.2. The equation of UNIQUAC activity coefficient model is in fact sum of two terms: a combinatorial term and a residual term, represented as

R

C

∑ χj lj j=1

(8)

⎛ θτ ⎞⎤ j ij ⎜ ⎟⎥ ∑⎜ C ⎟⎥ j = 1 ⎝ ∑k = 1 θkτkj ⎠⎦

(9)

c

where i, j, and k are indices, c is the number of components, τij is the adjustable parameter, and θj and Φi are the surface area and volume fractions used in UNIQUAC model. The D

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ternary system n-butyl acetate + pyrocatechol + water at the specified temperatures. As we can see in Figure 1, the calculated data are almost coincident with the experimental data, which indicates that the correlated results are consistent with the experimental results. It is confirmed again that the LLE data of the studied system can be calculated by NRTL and UNIQUAC models accurately over a wide temperature range and the obtained binary interaction parameters have high reliability. A comparison of the experimental D and S and the calculated D and S at 298.15 K was made in Figures 2 and 3. Other figures which show the comparisons at 308.15 and 318.15 K were supplied in the Supporting Information. The result shows that NRTL and UNIQUAC models are also available for D and S.

parameters of UNIQUAC are calculated by the following equations: li =

Z (ri − qi) + 1 − ri 2

τij = aij + bij /T + cij ln T + dijT

(10) (11)

c

ϕi = rx i i / ∑ xjrj (12)

j=1

c

θi = qixi /∑ xjqj

(13)

j=1

4. CONCLUSION Liquid−liquid equilibrium data for the ternary system of n-butyl acetate + pyrocatechol + water were measured at the temperature range of 298.15−318.15 K under 101.3 kPa. It can be inferred that the high values of distribution coefficients and separation factors indicate that n-butyl acetate is a promising solvent to remove pyrocatechol from water. The LLE data were well-correlated by the NRTL and UNIQUAC activity coefficient models, while the correlation of the NRTL model was superior to that of the UNIQUAC model. It can be inferred that the temperature has little effect on the LLE of the measured system at the temperature range of 298.15−318.15 K. So only a group of binary interaction parameters were regressed. The binary interaction parameters obtained from both models are important to simulate and optimize the industrial separation process of pyrocatechol.

where aij, bij, cij, and dij are UNIQUAC coefficients of the equations for binary interaction parameters. The relative molecular volume (r) and surface area (q) of pure component are shown in Table 3. The parameter estimation was conducted as what our previous work did by using the Fortran code TMLLLE2.024, and the calculated procedure depends on the Simplex method presented by Nelder and Mead.24 The corresponding binary interaction parameters of the NRTL and UNIQUAC model were obtained by minimizing the objective function defined as eq 14: k

OF =

m

∑i = 1 ∑ j = 1 ((W ijexp − W ijcal)/σij)2 K−n

(14)

where Wexp and Wcal are the measured mass fraction and calculated mass fraction, respectively. σ is standard deviation. k is the number of data points in the data group, and m is the number of temperature sets in our experiment. K is the number of all measured data points, and n is the total number of parameters. The experimental liquid−liquid equilibria data of the system of n-butyl acetate + pyrocatechol + water were correlated by NRTL and UNIQUAC models. The values of the binary interaction parameters calculated from NRTL and UNIQUAC models by regression depended on the determined phase equilibrium data are summarized in Table 4. The root-mean-square deviation (RMSD) provides a measure to check the accordance between the calculated data and the experimental data. The equation of the RMSD is presented as the following:25 RMSD =

⎛ (Wi ,exp − Wi ,cal)2 ⎞ ⎟ ∑ ⎜⎜∑ ∑ ⎟ 6 N ⎠ k ⎝ j i



ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.6b00280. Sources and mass fractions of the experimental chemicals and distribution coefficients of pyrocatechol vs mass fraction of pyrocatechol in the organic phase at 308.15 and 318.15 K (PDF)



AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest.



(15)

REFERENCES

(1) Greminger, D.; Burns, G.; Lynn, S.; Hanson, D.; King, C. Solvent Extraction of Phenols from Water. Ind. Eng. Chem. Process Des. Dev. 1982, 21, 51−54. (2) González-Muñoz, M. J.; Luque, S.; Á lvarez, J. R.; Coca, J. Recovery of Phenol from Aqueous Solutions Using Hollow Fibre Contactors. J. Membr. Sci. 2003, 213, 181−193. (3) Yang, C.; Jiang, Y.; Zhang, L.; Qian, Y. Liquid-Liquid Equilibria for the Ternary System Methyl Isobutyl Ketone + Water + Hydroquinone. J. Chem. Eng. Data 2006, 51, 2107−2109. (4) Jiang, H.; Fang, Y.; Fu, Y.; Guo, Q.-X. Studies on the extraction of phenol in wastewater. J. Hazard. Mater. 2003, 101, 179−190. (5) De Oliveira, L.; Aznar, M. (Liquid + Liquid) Equilibrium of {Water + Phenol + (1-Butanol, or 2-Butanol, or tert-Butanol)} Systems. J. Chem. Thermodyn. 2010, 42, 1379−1385. (6) Lin, Q.; Qin, W.; Dai, Y.-Y. Extraction behaviors of phenol in dilute solution by 1-octanol. Environ. Chem. 2003, 22, 48−52.

where N is the total number of tie-lines, Wexp stands experimental mass fraction, Wcal stands the calculated mass fraction, and subscripts i, j, and k denote the component, phase, and tie-line, respectively. The RMSD values are shown in Table 5. For the system investigated, the average RMSD calculated from NRTL model is 0.0114, and that calculated from the UNIQUAC model is 0.0200. The values are less than 5%, which illustrates that both models can successfully correlate the ternary system. Also we can infer from these values that the NRTL model is more proper to correlate the liquid−liquid equilibrium data for the system of n-butyl acetate + pyrocatechol + water than the UNIQUAC model. Figure 1 shows the LLE experimental data and calculated data correlated from the NRTL and UNIQUAC models for the E

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(7) Lei, Y.; Chen, Y.; Li, X.; Qian, Y.; Yang, S.; Yang, C. Liquid− Liquid Equilibria for the Ternary System 2-Methoxy-2-methylpropane + Phenol + Water. J. Chem. Eng. Data 2013, 58, 1874−1878. (8) Huang, H.-H.; Gai, H.-J. Study on the biodegradability of wastewater after steam stripping treated by different solvents. Guangzhou Chem. Ind. 2014, 42, 103−104. (9) Chen, Y.; Wang, Z.; Li, L. Liquid−liquid equilibria for ternary systems: Methyl butyl ketone + phenol + water and methyl butyl ketone + hydroquinone + water at 298.15 and 323.15 K. J. Chem. Eng. Data 2014, 59, 2750−2755. (10) Yang, C.; Qian, Y.; Jiang, Y.; Zhang, L. Liquid−liquid equilibria for the quaternary system methyl isobutyl ketone−water−phenol− hydroquinone. Fluid Phase Equilib. 2007, 258, 73−77. (11) Gonzalez, J. R. A.; Macedo, E. A.; Soares, M. E.; Medina, A. G. Liquid-liquid equilibria for ternary systems of water-phenol and solvents: data and representation with models. Fluid Phase Equilib. 1986, 26, 289−302. (12) Pinto, R. T. P.; Lintomen, L.; Luz, L. F. L., Jr.; Wolf-Maciel, M. R. Strategies for recovering phenol from wastewater: Thermodynamic evaluation and environmental concerns. Fluid Phase Equilib. 2005, 228−229, 447−457. (13) Narasimhan, K. S.; Reddy, C. C.; Chari, K. S. Solubility and equilibrium data of phenol-water-n-butyl acetate system at 30°C. J. Chem. Eng. Data 1962, 7, 340. (14) Schuberth, H.; Leibnitz, E. The phase equilibria liquid-liquid system phenol-n-butyl acetate- water at 44.4°C. J. Prakt. Chem. 1958, 6, 31. (15) Mohammad Doulabi, F. S.; Mohsen-Nia, M. Ternary Liquid− Liquid Equilibria for Systems of (Sulfolane + Toluene or Chloronaphthalene + Octane). J. Chem. Eng. Data 2006, 51, 1431− 1435. (16) Dechambre, D.; Wolff, L.; Pauls, C.; Bardow, A. Optimal Experimental Design for the Characterization of Liquid−Liquid Equilibria. Ind. Eng. Chem. Res. 2014, 53, 19620−19627. (17) Iglesias, M.; Orge, B.; Tojo, J. Refractive Indices, Densities and Excess Properties on Mixing of the Systems Acetone + Methanol + Water and Acetone + Methanol + 1-Butanol at 298.15 K. Fluid Phase Equilib. 1996, 126, 203−223. (18) Yang, C.; Qian, Y.; Guo, J.; et al. Liquid−Liquid Equilibria for the Ternary System Methyl Isobutyl Ketone + 1, 2-Benzenediol + Water. J. Chem. Eng. Data 2014, 59, 3663−3667. (19) Aminabhavi, T. M.; Banerjee, K. Density, Viscosity, Refractive Index and Speed of Sound in Binary Mixtures of Methyl Acetate + Ethylene Glycol or + Poly(ethylene glycol) in the Temperature Interval (298.15−308.15) K. J. Chem. Eng. Data 1998, 43, 852−855. (20) Peschke, N.; Sandler, S. I. Liquid-liquid equilibria of fuel oxygenate+ water+ hydrocarbon mixtures. 1[J]. J. Chem. Eng. Data 1995, 40, 315−320. (21) Wang, B.; Ran, W.; Li, S. Liquid−liquid equilibria for systems of water + methanol + methyl anthranilate at several temperatures. Fluid Phase Equilib. 2011, 310, 56−62. (22) Renon, H.; Prausnitz, J. M. Local Compositions in Thermodynamic Excess Functions for Liquid Mixtures. AIChE J. 1968, 14, 135−144. (23) Abrams, D. S.; Prausnitz, J. M. Statistical Thermodynamics of Liquid Mixtures: A New Expression for the Excess Gibbs Energy of Partly or Completely Miscible Systems. AIChE J. 1975, 21, 116−128. (24) Nelder, J. A.; Mead, R. A simplex method for function minimization. Comput. J. 1965, 7, 308−313. (25) Kim, Y. K.; Park, D. W. Liquid−liquid equilibrium for the quaternary system water + tetrahydrofuran + n-heptane + butyl acetate mixture at 25°C and atmospheric pressure. J. Ind. Eng. Chem. 2008, 14, 602−607. (26) Renon, H.; Prausnitz, J. M. Local Compositions in Thermodynamic Excess Functions for Liquid Mixtures. AIChE J. 1968, 14, 135−144.

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