Article pubs.acs.org/jced Liquid−Liquid Equilibrium of the Ternary System of Water + Phenol + (Propan-2-yl) Benzene at Several Temperatures CumeneJavad Saien* and Mahdieh Razi Asrami Department of Applied Chemistry, Bu−Ali Sina University, Hamedan 65174, Iran ABSTRACT: Liquid−liquid equilibrium (LLE) data for the ternary chemical system of {water + phenol + (propan-2-yl) benzene (cumene)} were presented at temperatures of 293.2, 298.2, and 308.2 K and under the ambient pressure of 81.5 kPa. Experiments were performed based on the cloud point titration method and refractive index measurements. Results show that the phenol solubility in cumene is significantly higher than in water especially at higher phenol concentrations. The phenol distribution coefficient and separation factor were obtained within 1.490−3.418 and 82.06−300.24, respectively. The capability of cumene, as a solvent to extract phenol from aqueous solutions, particularly for low level phenol concentrations, was revealed. The consistency of tie line data was sufficiently assessed by the Othmer−Tobias and Bachman equations. Meanwhile, the well-known NRTL and UNIQUAC thermodynamic models were employed to reproduce the experimental data and obtaining the binary interaction parameters. The appropriate low value root-mean-square deviations confirm the good agreement between experimental data and the model correlated values. 1. INTRODUCTION The removal of phenol and phenolic compounds from aqueous solutions has attracted much attention due to their toxicity and pollution even at low concentrations (<5 mg/L).1 Phenol and its derivatives are very important compounds since they widely present in the wastewater of industries such as petrochemical plants, petroleum refining, coal gasification, pharmaceutical plastics, paint, paper, and wood products.2 Thereby, it is necessary to refine the wastewaters containing phenolic compounds before releasing into the environment. Beside the toxicity, the water’s unpleasant taste and odor due to phenol and its derivatives are remarkable. Phenols usually form a binary azeotrope with water; hence, the separation process is very hard. Therefore, liquid−liquid extraction can be a desired and efficient process. Until now, many solvents have been applied for the extraction of phenol such as methyl isobutyl ketone (MIBK),3 ethylene glycol,4 and ionic liquids.5 Meanwhile, the liquid−liquid equilibrium (LLE) data for {water + phenol + solvent} systems have been reported by many researchers. Different solvents have been used in this regard; for example, data for toluene or ethylbenzene6 and heptane or octane7 were reported by Martin et al. Also, Hwang and Park produced the dimethyl carbonate and diphenyl carbonate LLE data with phenol and water.8 Moreover, 2methoxy-2-methylpropane,9 methyl butyl ketone,10 and methyl isopropyl ketone11 solvents were used by Chen and co-workers. Recently, Liu et al. investigated the systems of {methyl tertbutyl ketone (MTBK) + phenol + water}12 and {mesityl oxide + phenol + water}.13 Among the used solvents, so far, ketone and ether structure solvents exhibit more efficiency in separation. © XXXX American Chemical Society (Propan-2-yl) benzene (cumene) is a well-known solvent that has been recommended as a safe solvent alternative in the liquid−liquid extraction process.14,15 It has excellent chemical stability, a low vapor pressure, the capability to form two phases at low temperatures, and rapid phase separation.14 Low density and low viscosity (0.739 mPa·s at T = 298.2 K) are other advantages as well as its low price.16 In a research, carried out by Liu et al.,17 the phenol extraction from water with cumene was studied at different temperatures and pH. The results indicate that higher temperatures, but lower aqueous phase pH values, provide more efficient extraction. Sodium hydroxide solution was used as the stripping reagent, and it was shown that almost all of the phenol was stripped from the solvent. Further, the reusability of cumene was investigated and it was demonstrated that no obvious decrease in the extraction percent or recovery of phenol was observed within five regeneration steps. Pop et al.18 investigated the LLE data for this system just at T = 293.2 K with no data modeling. It is of high importance to have the LLE data systematically for the aim of design, simulation, and optimization of a liquid− liquid extraction process. In this study LLE data of the ternary system of {water + phenol + cumene} were determined at temperatures of 293.2, 298.2, and 308.2 K and under ambient pressure. The cloud-point method and refractive index measurement were employed.19 The efficiency of the process was evaluated by distribution coefficients and separation factor. Because of high toxicity of phenol, its concentration in Received: April 27, 2017 Accepted: August 7, 2017 A DOI: 10.1021/acs.jced.7b00393 J. Chem. Eng. Data XXXX, XXX, XXX−XXX Journal of Chemical & Engineering Data Article Table 1. Source, Purity Grade, Density, and Refractive Index of the Used Chemicals ρc (g·cm−3) chemical name cumene water phenol a CAS RN 98-82-8 7732-18-5 108-95-2 source mass fraction purity Merck Hastaran Merck ≥0.99 ultrapure ≥0.995 b d exp. 0.85754 0.99704 ndc lit. exp. 23 0.8574 0.9969320 d 1.49005 1.33250 lit. 1.488923 1.332524 a Chemical Abstract Service Registry Number. bPurity stated by the manufacturer. cT = 298.2 K. dp = 81.5 kPa. Standard uncertainties are u(T) = 0.01 K, u(p) = 0.3 kPa, u(nd) = 0.0007, and relative uncertainty of density ur(ρ) = 0.001. Table 2. Refractive Index Data for Different Aqueous and Organic Phase Compositions of {Water (1) + Phenol (2) + Cumene (3)} under Ambient Pressure of p = 81.5 kPa and Temperatures of T = 293.2, 298.2, and 308.2 Ka aqueous phase w11 w21 organic phase w31 nd w13 w23 w33 nd 0.0006 0.0017 0.0035 0.0045 0.0063 0.0081 0.0095 0.0104 0.0116 0.0128 0.0143 0.0167 0.0215 0.0000 0.0099 0.0199 0.0298 0.0397 0.0495 0.0594 0.0692 0.0790 0.0987 0.1182 0.1376 0.1761 0.9982 0.9878 0.9764 0.9655 0.9538 0.9422 0.9310 0.9202 0.9092 0.8884 0.8673 0.8456 0.8023 1.49150 1.49200 1.49250 1.49305 1.49345 1.49365 1.49410 1.49460 1.49515 1.49660 1.49750 1.49855 1.50050 0.0009 0.0029 0.0045 0.0075 0.0091 0.0104 0.0134 0.0161 0.0192 0.0163 0.0180 0.0215 0.0242 0.0000 0.0099 0.0199 0.0297 0.0396 0.0494 0.0591 0.0688 0.0784 0.0983 0.1178 0.1369 0.1756 0.9984 0.9870 0.9755 0.9626 0.9512 0.9400 0.9273 0.9149 0.9023 0.8853 0.8641 0.8414 0.8001 1.49001 1.49110 1.49150 1.49195 1.49253 1.49300 1.49345 1.49425 1.49475 1.49545 1.49675 1.49745 1.49995 0.0011 0.0047 0.0061 0.0089 0.0100 0.0122 0.0157 0.0198 0.0230 0.0242 0.0249 0.0268 0.0000 0.0099 0.0198 0.0297 0.0395 0.0493 0.0590 0.0686 0.0976 0.1170 0.1365 0.1751 0.9988 0.9852 0.9739 0.9613 0.9503 0.9383 0.9251 0.9115 0.8792 0.8587 0.8385 0.7979 1.48590 1.48640 1.48670 1.48715 1.48780 1.48835 1.48870 1.48940 1.49195 1.49310 1.49410 1.49665 293.2 K 0.9998 0.9892 0.9790 0.9686 0.9580 0.9477 0.9371 0.9270 0.9168 0.0000 0.0099 0.0199 0.0299 0.0399 0.0498 0.0612 0.0697 0.0797 0.0001 0.0007 0.0009 0.0013 0.0019 0.0023 0.0029 0.0031 0.0033 1.33350 1.33495 1.33675 1.33910 1.34125 1.34305 1.34495 1.34625 1.34745 0.9996 0.9890 0.9784 0.9682 0.9578 0.9475 0.9370 0.9268 0.9167 0.0000 0.0099 0.0199 0.0299 0.0399 0.0498 0.0612 0.0697 0.0797 0.0003 0.0009 0.0015 0.0017 0.0021 0.0025 0.0031 0.0033 0.0035 1.33300 1.33495 1.33670 1.33895 1.34040 1.34240 1.34345 1.34520 1.34663 0.9994 0.9886 0.9782 0.9678 0.9577 0.9471 0.9368 0.9262 0.9161 0.0000 0.0099 0.0199 0.0299 0.0399 0.0498 0.0611 0.0697 0.0796 0.0005 0.0013 0.0017 0.0021 0.0023 0.0029 0.0033 0.0039 0.0041 1.33195 1.33370 1.33515 1.33695 1.33950 1.34095 1.34280 1.34410 1.34605 298.2 K 308.2 K a Standard uncertainties are u(T) = 0.1 K, u(nd) = 0.0007, u(p) = 0.3 kPa, and u(w) = 0.002 except u(w31) = 0.0005. conventional wastewaters does not reach high levels.20 So, a relevant practical phenol concentration range in aqueous phase was considered. The nonrandom two-liquid (NRTL) and the universal quasichemical (UNIQUAC) thermodynamic models were applied to correlate the experimental LLE data and to determine interaction parameters using the Aspen Plus simulator. The experimental tie-line data were tested by Othmer−Tobias21 and Bachman22 equations. Also, the rootmean-square deviations between experimental and simulated data were determined. B DOI: 10.1021/acs.jced.7b00393 J. Chem. Eng. Data XXXX, XXX, XXX−XXX Journal of Chemical & Engineering Data Article Figure 1. Comparison of the mass fractions of cumene in water solution (▲), w31; and water in cumene solution (●), w13; with the corresponding literature data27,28 (△ and ○). 2. MATERIALS AND METHODS 2.1. Materials. Phenol and cumene were supplied from Merck with mass fraction purities of more than 0.995 and 0.99, Figure 3. Dependency of mass fractions of cumene in aqueous and organic phases on the refractive index under ambient pressure of p = 81.5 kPa and temperatures of: ■, T = 293.2 K; ●, T = 298.2 K; ▲, T = 308.2 K. Figure 2. Dependency of phenol mass fractions on the refractive index of cloudy solutions under the ambient pressure of p = 81.5 kPa and temperatures of: ■, T = 293.2 K; ●, T = 298.2 K; ▲, T = 308.2 K. 2.2. Measurements. The experimental LLE data were determined using an equilibrium jacketed cell (about 5 cm3 volume) equipped with a magnetic stirrer and based on the titration cloud point method as described in the previous works.25,26 The temperature of the cell was controlled by the circulating water, conducted by the external stream of a thermostat (Julabo, Germany) controlled by a thermocouple with an uncertainty of 0.01 K, and its accuracy was examined by means of an accurate thermometer (Amadigit, ad 3000th, percica, Germany). An electronic Ohaus balance (Adventurer, Pro AV264, Switzerland, uncertainty 0.0001 g) was used to weigh all prepared samples to the desired values. To obtain the dependency of refractive index and solute concentration for cloud point method, binary mixtures (phenol + water) and (phenol + cumene) of known overall respectively, and were used without further purification. Fresh deionized water with the ionic conductivity <0.08 μS·cm−1 was produced from a deionizer apparatus (Hastaran Co). The source, purity grade, density, and refractive index of the chemicals are summarized in Table 1. There is a good agreement with the literature data. The densities of liquids were measured by means of an oscillating U-tube densimeter (Anton Paar DMA4500, Austria). The apparatus was calibrated with dry air and bidistilled fresh water. The refractive index of the components were measured with an Abbe refractometer (AR4 Kruss, Germany). The standard uncertainty in refractive index measurements was 0.0007, and the relative uncertainty of density was 0.001. C DOI: 10.1021/acs.jced.7b00393 J. Chem. Eng. Data XXXX, XXX, XXX−XXX Journal of Chemical & Engineering Data As Temp Increases, slippage of phenol to aqueous in extraction will increases due to increased solubility of phenol in water. Article Table 3. Experimental Tie-Lines for the Ternary System of {Water (1) + Phenol (2) + Cumene (3)} under the Ambient Pressure of p = 81.5 kPa and Temperatures of T = 293.2, 298.2, and 308.2 Ka aqueous phase w11 0.9799 0.9737 0.9661 0.9579 0.9543 0.9518 0.9487 0.9450 0.9427 w21 Phenol in aqueous water 0.0191 0.0251 0.0324 0.0403 0.0438 0.0463 0.0492 0.0528 0.0549 organic phase w31 w13 w23 w33 D2 S 0.0342 0.0516 0.0826 0.1194 0.1474 0.1581 0.1610 0.1652 0.1774 0.9598 0.9405 0.9061 0.8652 0.8340 0.8222 0.8190 0.8142 0.8007 1.7916 2.0975 2.5489 2.9638 3.3657 3.4182 3.2700 3.1322 3.2304 300.24 258.78 219.30 185.34 174.18 165.78 155.52 144.95 139.85 0.0299 0.0558 0.0862 0.1140 0.1445 0.1583 0.1685 0.1768 0.1777 0.9624 0.9331 0.8985 0.8671 0.8326 0.8169 0.8054 0.7960 0.7949 1.8698 1.9692 2.5443 2.6687 2.8366 2.8165 2.9663 2.7693 2.7193 240.58 172.54 162.29 135.61 117.56 107.40 107.18 95.25 93.41 0.0241 0.0397 0.0710 0.0906 0.1101 0.1242 0.1461 0.1658 0.1751 0.9673 0.9493 0.9133 0.8908 0.8683 0.8521 0.8269 0.8042 0.7936 1.4904 1.6244 2.0801 2.2211 2.3781 2.5168 2.7740 2.8903 2.7467 172.49 145.87 128.86 114.86 105.46 101.23 97.52 91.02 82.06 293.2 K 0.0009 0.0011 0.0014 0.0017 0.0018 0.0019 0.0020 0.0022 0.0023 0.0058 0.0077 0.0112 0.0153 0.0184 0.0196 0.0199 0.0204 0.0217 298.2 K 0.9831 0.9703 0.9646 0.9554 0.9469 0.9414 0.9408 0.9335 0.9323 0.0160 0.0283 0.0339 0.0427 0.0509 0.0562 0.0568 0.0639 0.065 0.0008 0.0013 0.0015 0.0018 0.0021 0.0023 0.0023 0.0026 0.0027 0.0076 0.0110 0.0151 0.0188 0.0228 0.0246 0.0260 0.0271 0.0272 0.9825 0.9739 0.9638 0.9569 0.9511 0.9479 0.9445 0.9396 0.9329 0.0162 0.0245 0.0342 0.0408 0.0463 0.0494 0.0527 0.0574 0.0637 0.0013 0.0016 0.0020 0.0023 0.0025 0.0027 0.0028 0.0030 0.0033 0.0084 0.0108 0.0155 0.0185 0.0214 0.0235 0.0268 0.0298 0.0312 308.2 K a Standard uncertainties are u(T) = 0.1 K, u(p) = 0.3 kPa, and u(w) = 0.002 except u(w31) = 0.0005. refractive index increased with the increase of phenol mass fraction because of the higher refractive index of phenol, compared to water. A similar explanation is also corresponding when phenol was added to cumene. A number of firmly closed miniature equilibrium cells were used to obtain binodal curves and tie line data. Three used components (water, phenol, and cumene) with specified mass fractions were introduced to the cells and were agitated vigorously by a shaking water bath (N-BIOTEK-304), while temperatures were set at 293.2, 298.2, and 308.2 K (uncertainty of 0.1 K). The content of the cells was shaking for 4 h at 175 rpm, then left to settle for 12 h to complete separation of phases under a specified temperature. After reaching phase equilibrium, each phase layer (top organic phase and the bottom aqueous phase) was carefully sampled by a syringe and analyzed via measuring their refractive index. The unknown compositions were determined by using calibration curves. All experiments were carried out under ambient pressure of 81.5 kPa. A similar procedure for determination of the composition of phases has been employed by a number of investigators.19,29 compositions were introduced to the cell and stirred at constant temperature. The third component (cumene or water) was titrated into the cell with a microburet and were agitated vigorously to form a stable cloudy mixture. Then it was left to settle for 1 h to phase splitting, and samples of the mixture were collected by a syringe (uncertainty in mass fraction u(w) = 0.002 except u(w31) = 0.0005). Generally, wi1 and wi3 refer to the mass fractions of the ith (water = 1, phenol = 2, and cumene = 3) components in the aqueous and organic phases, respectively. Measurements for each mass fraction were repeated at least three times; the refractive index of samples was measured, and the average value was considered for calibration of the known sample mass fractions. It is worth noting that refractometer was connected on line to the circulating water stream from the thermostat and temperature of the refractometer was retained constant at the same temperature of mixtures. The data of calibration curves and refractive indexes are presented in Table 2. Presented in Figure 1 is the comparison between data in this work with those reported in the literature for the case of the absence of phenol.27,28 Totally, there is a very low mutual solubility for cumene and water. The appeared difference could be due to different dominant conditions, analysis method, and ambient pressure. The relationships of mass fraction and refractive index are presented in Figures 2 and 3. Calibration curves show that the 3. RESULTS AND DISCUSSION 3.1. Tie-Line Data. The obtained LLE data for ternary system {water + phenol + cumene} at 293.2, 298.2, and 308.2 K are listed in Table 3. Results show that the solubility of water in organic phase is increased with increasing phenol mass D DOI: 10.1021/acs.jced.7b00393 J. Chem. Eng. Data XXXX, XXX, XXX−XXX Journal of Chemical & Engineering Data Article Figure 4. Ternary system of {water + phenol + cumene} under the ambient pressure of p = 81.5 kPa and temperatures of T = 293.2 K (a), T = 298.2 K (b), and T = 308.2 K (c); ■ and solid lines are experimental tie lines; ● and dashed lines are NRTL correlated tie lines; ▲ and dotted lines are UNIQUAC correlated tie lines; ☆ and dash−dotted lines are Pop et al.18 tie-line data at T = 293.2 K. fraction; however, the solubility of cumene in water is almost nil within the used range of concentrations. The phase behavior for the ternary system is shown in Figure 4 for different used temperatures. As is observed, phenol + cumene is the completely miscible liquid pair; water + phenol is the partial miscible pair, and the water + cumene is the immiscible pair. This system therefore behaves as a type-2 LLE.30 The slope of tie-lines clearly shows that affinity of phenol to dissolve in cumene is higher than in water at higher concentrations of phenol. Tie-line data reported by Pop et al.18 at 293.2 are also presented in Figure 4. As is observed, there is a reasonable agreement between data. To evaluate the efficiency of phenol extraction by cumene, the separation factor was calculated from S= D2 D1 (1) where D1 and D2 are the distribution coefficients of water and phenol, as w D1 = 13 w11 (2) D2 = w23 w21 (3) The corresponding D2 and S values are listed in Table 3. The variation of D2 and S are shown in Figures 5 and 6, respectively. According to the results, distribution coefficient of phenol is E DOI: 10.1021/acs.jced.7b00393 J. Chem. Eng. Data XXXX, XXX, XXX−XXX Journal of Chemical & Engineering Data Article Bachman A1 B1 R 293.2 298.2 308.2 −2.0426 −1.6958 −1.7837 0.5791 0.7186 0.6430 0.9890 0.9883 0.9914 A2 B2 R2 −0.2155 −0.2967 −0.2735 1.198 1.2829 1.2546 0.9989 0.9984 0.9972 (5) exp cal 2 ∑i ∑m ∑n (wimn − wimn ) 6N (6) cal where wexp imn and wimn are the experimental and correlated mass fractions of the components in which i = 1, 2, 3 in phases, m = I, II, and on tie lines n = 1, 2, ..., N. The obtained very low rmsd values, given in Table 5, indicate a satisfactory agreement between experimental and simulation data. Table 4. Fitting Parameters in Othmer−Tobias and Bachman Equations T (K) ⎛w ⎞ w33 = A 2 + B2 ⎜ 33 ⎟ ⎝ w11 ⎠ rmsd = Figure 6. Separation factor (S) of phenol versus its mass fraction in the aqueous phase under ambient pressure of p = 81.5 kPa and temperatures of: ■, T = 293.2 K; ●, T = 298.2 K; ▲, T = 308.2 K. 2 (4) where A1, B1 and A2, B2 are the intercept and slopes for Othmer−Tobias (logarithmic function) and Bachman equations, fitted from the LLE data. The parameter values with the corresponding regression coefficients (R2) are given in Table 4. Both of the regression coefficients are close to unit, representing a high consistency of the experimental data. 3.2. Data Correlation. The experimental tie-line data were correlated by using the Aspen Plus (Version 8.4) data regression tool for both the NRTL and the UNIQUAC models. This software employs an objective function, called “Britt-Luecke”, to find model parameters.31 The obtained NRTL and UNIQUAC coefficients of the equations for binary interaction parameters in this work are listed in Table 5. The UNIQUAC structural parameters of ri (the number of segments per molecule) and qi (the relative surface area per molecule) correspond to the number of molecular groups and the individual values of the van der Waals volume and area of the molecules were obtained and presented in Table 6. Details of the meaning of parameters and equations are given in the literature.32,33 The comparison between experimental and the values obtained from NRTL and UNIQUAC model is presented in the ternary diagrams plotted in Figure 4. A very close agreement is observed. Meanwhile, to represent the consistency of the data reproduced by the used models, the root-meansquare deviation (rmsd) was calculated by the following equation: Figure 5. Distribution coefficients of phenol versus its mass fraction in the aqueous phase under ambient pressure of p = 81.5 kPa and temperatures of: ■, T = 293.2 K; ●, T = 298.2 K; ▲, T = 308.2 K. Othmer−Tobias ⎛ 1 − w33 ⎞ ⎛ 1 − w11 ⎞ ln⎜ ⎟ = A1 + B1 ln⎜ ⎟ ⎝ w11 ⎠ ⎝ w33 ⎠ 4. CONCLUSION In this work, the liquid−liquid equilibrium for the ternary system of {water + phenol + cumene} was studied at temperatures of 293.2, 298.2, and 308.2 K and under the ambient pressure of 81.5 kPa. The experimental results showed that the distribution coefficient and separation factor lay within the ranges of 1.490−3.418 and 82.06−300.24, respectively. Results showed that phenol solubility in cumene increased with increasing phenol concentrations in aqueous phase; however, higher separation factors were achieved for its low concentrations. The reliability of tie-lines was evaluated with Othmer− Tobias and Bachman equations, and high levels of agreement were revealed. For modeling, the NRTL and the UNIQUAC models reproduced the tie lines very good by estimating the binary interaction coefficients, and it was found that the NRTL model predicts a better agreement for the system. within the range 1.490−3.418. Meanwhile, the separation factor was within 82.06−300.24. Therefore, cumene demonstrates as a good solvent for separation phenol from water. The separation factor ranges, reported for a number of solvents, mentioned above, are respectively 2390−4255,10 1007−2599,12 1334− 3953,13 99−495,19 and 126−168,19 all at 298.2 K. Results presented in Figure 6 indicate that higher separation factors are associated with low concentrations of phenol and that the extraction performance decreases with increasing temperature. The reliability of the LLE data was evaluated by Othmer− Tobias and Bachman correlations as F DOI: 10.1021/acs.jced.7b00393 J. Chem. Eng. Data XXXX, XXX, XXX−XXX Journal of Chemical & Engineering Data Article Table 5. NRTL and UNIQUAC Binary Interaction Parameters for the System of {Water (1) + Phenol (2) + Cumene (3)} under the Ambient Pressure of p = 81.5 kPa and Different Temperatures components NRTL UNIQUAC T (K) i−j bij (K) bji (K) cij rmsd bij (K) bji (K) rmsd 293.2 1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3 −614.923 −10000 −645.91 3305.05 −19434.79 −81.563 −333.13 −49290.48 −609.17 −7631.72 −4492.33 1477.50 6043.77 −4213.67 1069.50 −8197.49 −4879.33 1236.10 0.3 0.2 0.3 0.3 0.2 0.15 0.3 0.2 0.3 0.0012 1244.48 −78.6393 312.453 −73.753 −84.390 358.38 1208.09 −80.002 358.62 53.1281 −328.562 −549.153 622.85 −307.00 −617.48 108.508 −290.64 −667.18 0.0018 298.2 308.2 ■ r q water phenol cumene 0.9200 3.5465 5.2709 1.4000 2.7160 4.0560 AUTHOR INFORMATION Corresponding Author *E-mail: saien@basu.ac.ir. ORCID Javad Saien: 0000-0001-5731-0227 Funding The authors wish to acknowledge the Bu-Ali Sina University authorities for the financial support to carry out this work. The work was supported by the University Research Council. Notes The authors declare no competing financial interest. ■ 0.0009 0.0159 0.0022 (10) 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. (11) Lv, R.; Li, L.; Wang, H.; Chen, Y. Experimental Determination and Correlation of Liquid−Liquid Equilibria for Methyl Isopropyl Ketone + Phenol + Water Mixtures at 298.15, 313.15 and 323.15 K. J. Chem. Eng. Data 2016, 61, 2221−2225. (12) Liu, D.; Luo, L.; Li, L.; Chen, Y. Liquid−Liquid Equilibria for the Methyl Tert-Butyl Ketone + Phenol + Water Ternary System at 298.15, 313.15 and 323.15 K. J. Solution Chem. 2015, 44, 1891−1899. (13) Liu, D.; Li, L.; Lv, R.; Chen, Y. Liquid−Liquid Equilibria for the Ternary System Mesityl Oxide + Phenol + Water at 298.15, 313.15, and 323.15 K. J. Chem. Eng. Data 2016, 61, 2493−2498. 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