Determination and Correlation of LiquidâLiquid Equilibria Data for

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

pubs.acs.org/jced

Determination and Correlation of Liquid−Liquid Equilibria Data for Water + Cyclohexanol + (Mesityl Oxide, Toluene, and p‑Xylene) Ternary Systems at Different Temperatures Chuanfu Zhu, Yingmin Yu,* Hui Jiang, and Qingsong Li State Key Laboratory of Heavy Oil Processing, College of Chemical Engineering, China University of Petroleum (East China) Qingdao, Shandong 266580, China ABSTRACT: Accurate liquid−liquid equilibria (LLE) data are of momentous significance for the design, simulation, as well as optimization of the extractive process. To assemble the essential data for the operation of extracting cyclohexanol from the aqueous solution, LLE data for {water + cyclohexanol + toluene}, {water + cyclohexanol + mesityl oxide}, and {water + cyclohexanol + p-xylene} ternary systems were experimentally measured at 303.15 and 323.15 K under 101.3 kPa. The separating power of the extractants was assessed via the distribution coefficient and selectivity. The Othmer−Tobias and Bachman equations were applied to confirm the experimental data coherence. The data obtained from experiments were correlated via the nonrandom two liquid (NRTL) and universal quasi-chemical (UNIQUAC) models, and the regression result was better since the RMSD values were all less than 0.2%. However, the UNIQUAC model was preferable since the RMSD was smaller. In addition, the relevant binary interaction parameters were also generated during the relevant correlations.

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INTRODUCTION Adipic acid, the raw material to manufacture resins, plasticizers, nylon-66, and other products, is a significant bulk chemical. Nowadays, the adipic acid yield has already reached a large scale in the world. Generally, adipic acid is produced through the oxidation reaction of KA oil (mixture of cyclohexanol and cyclohexanone) with nitric acid as an oxidant.1 However, this technology carries the mass of the defective and stoichiometric waste products, NOx, which are generally assumed to result in ozone destruction and global warming.2−4 For the past few years, a clean, safe, and cost-effective process to manufacture adipic acid was applied without any foreseen operational problems for large scale production.5 In the operation, adipic acid is synthesized in a high yield through an oxidation reaction with cyclohexanol, cyclohexanone, and 30% H2O2. Furthermore, no other organic solvents are used, and water is the sole theoretical co-product.6 However, after the reaction, the unconverted cyclohexanol and cyclohexanone in the water phase need to be handled, otherwise it will cause great harm to the environment and restrict the development of the process.3 For the purpose of deposing of this kind of aqueous solution, several effective chemical methods could be applied, for instance, solvent extraction, incineration, and activation of carbon adsorption.7 However, incineration consumes a large amount of energy and further causes air pollution. Meanwhile, the adsorption activated carbon rate is very slow and difficult to achieve in industrialization. Compared with other processing methods, liquid−liquid extraction seems to be a simple, energy-efficient, and environmentally friendly process. It is well-known that the design, simulation, and optimization of a proper extraction operation needs the reliable © XXXX American Chemical Society

ternary liquid−liquid equilibria (LLE) data and the LLE behavior. It recently has been studied and many extractants, such as benzene and cyclohexane, have been applied to investigate the possibility of isolating cyclohexanone from the aqueous solution, and it has a better extractive efficiency for the cyclohexanone separation,8,9 but only a few for refining cyclohexanol from water. Therefore, after reading many LLE references and analyzing the LLE data from our preexperiments, we decided to study the LLE data and behavior of the systems {water + cyclohexanol + toluene}, {water + cyclohexanol + mesityl oxide}, and {water + cyclohexanol + pxylene} to constitute the database. LLE data for the ternary systems {water + cyclohexanol + toluene}, {water + cyclohexanol + mesityl oxide}, and {water + cyclohexanol + p-xylene} were measured at 303.15 and 323.15 K under 101.3 kPa in this work. The separation power of the extractants were investigated by the distribution coefficient and selectivity. Othmer−Tobias and Bachman equations were applied to assess the coherence and dependability of the experimental data.10,11 In addition, the data obtained from the experiments were also correlated via nonrandom two liquid (NRTL) and universal quasi-chemical (UNIQUAC) models.12,13 The binary interaction parameters were also generated during the correlation process. Received: July 21, 2017 Accepted: April 3, 2018

A

DOI: 10.1021/acs.jced.7b00674 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Purity and Characterization of the Chemical Reagents ρ (g cm−3) (101.3 kPa) component

reported GC purity (mass%)

water

7732-18-5

cyclohexanol

108-93-0

p-xylene toluene mesityl oxide a

CAS

GC purity (mass%)

exp.

99.92

0.9970

⩾99.5

99.66

0.9615

106-42-3

⩾99.0

99.53

0.8565

108-88-3

⩾99.5

99.91

0.8621

⩾98.5

141-79-7 b

98.73

c

d

0.8576 e

lit. 25b

0.99706 0.9970025a 0.941630c 0.941630d 0.8566125e 0.8566125f 0.8621925g 0.8621925h 0.85825i

nD (101.3 kPa) exp.

lit.

1.3324

1.332525b 1.3325025a 1.462130c 1.462130d 1.4932525e 1.4932525f 1.4939025g 1.4939025h 1.44225i

1.4621 1.4931 1.4938 1.4416

f

Taken from ref 14. Taken from ref 15. Taken from ref 16. Taken from ref 17. Taken from ref 18. Taken from ref 19. gTaken from ref 20. Taken from ref 21. iTaken from ref 22. kStandard uncertainties, u, were u(T) = 0.01 K, u(P) = 0.7 kPa, u(ρ) = 0.008 gcm−3, and u(nD) = 0.006.

h

Table 2. Experimental LLE Data (Mass Fraction) for the Water (1) + Cyclohexanol (2) + Solvents (3) Systems at 303.15 K under 101.3 kPaa organic phase solvent toluene

p-xylene

mesityl oxide

a

aqueous phase

w1

w2

w3

w1

w2

w3

D

S

0.0013 0.0027 0.0021 0.0023 0.0023 0.0021 0.0021 0.0021 0.0006 0.0006 0.0014 0.0011 0.0011 0.0011 0.0011 0.0014 0.0627 0.0670 0.0690 0.0720 0.0751 0.0737 0.0760 0.0780

0.0190 0.0358 0.0488 0.0586 0.0762 0.1227 0.1356 0.1528 0.0135 0.0310 0.0452 0.0562 0.0692 0.0854 0.1147 0.1303 0.0180 0.0503 0.0670 0.0822 0.0952 0.1098 0.1227 0.1454

0.9797 0.9615 0.9491 0.9391 0.9215 0.8752 0.8623 0.8451 0.9858 0.9684 0.9534 0.9428 0.9297 0.9135 0.8842 0.8683 0.9193 0.8828 0.8639 0.8458 0.8297 0.8165 0.8013 0.7766

0.9929 0.9904 0.9886 0.9875 0.9862 0.9836 0.9825 0.9818 0.9936 0.9899 0.9870 0.9848 0.9834 0.9822 0.9796 0.9784 0.9534 0.9514 0.9499 0.9491 0.9481 0.9476 0.9468 0.9462

0.0053 0.0082 0.0099 0.0108 0.0120 0.0144 0.0155 0.0159 0.0048 0.0089 0.0109 0.0125 0.0141 0.0151 0.0174 0.0178 0.0010 0.0036 0.0053 0.0061 0.0073 0.0078 0.0091 0.0099

0.0018 0.0014 0.0015 0.0017 0.0017 0.0019 0.0020 0.0023 0.0016 0.0012 0.0021 0.0026 0.0026 0.0027 0.0030 0.0038 0.0455 0.0451 0.0448 0.0449 0.0447 0.0446 0.0441 0.0439

3.61 4.37 4.91 5.44 6.34 8.50 8.75 9.63 2.84 3.48 4.16 4.48 4.92 5.67 6.60 7.33 17.13 14.07 12.73 13.56 13.12 14.09 13.42 14.68

2848 1593 2279 2328 2739 3963 4134 4516 4342 5631 3017 4137 4234 5000 5901 5150 260 200 175 179 166 181 167 178

Standard uncertainties, u, were u(T) = 0.01 K, u(P) = 0.7 kPa, and u(w) = 0.003.

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́ measure the density. In addition, the Abbe−Hilger refrac−3 tometer with a precision of ±6 × 10 in the experimental measurements was applied to investigate the refractive indices. During the density measurements, the estimated temperature uncertainties were 0.01 K. As we could see, there were some differences between the data of the literature and experimental procedures, the reason for this may be the existence of the nonvolatile impurities or water in chemicals. Apparatus and Procedure. The experimental equipment and the analytical method that were employed in the study have been used in a previous study23 as well as other typical articles.24,25 During the experiment, the desired mixture was loaded into the cell when it was attained and was kept constant at the assigned temperature within ±0.1 K. The mixture was then agitated intensively for more than 2 h to get a sufficient mixing.

EXPERIMENTAL SECTION

Chemical Reagents. The characterization and purity of the chemicals that were used during the experiment are shown in Table 1. The asserted purity for all of the chemicals were >0.985 (mass fraction). Deionized water, which was made in the laboratory, was applied during all of the experiments. The chemical reagents purities were determined through gas chromatography (GC), and no impurities were found that could affect the experimental measurements, hence all of the chemical reagents, which were received from the Sinopharm Group Co., Ltd., were applied without any further purification. The physical properties that were measured by the experiments and cited from literatures are all shown in Table 1.14−22 The temperature controlled Anton Paar DMA 4500 density meter with a precision of ±8 × 10−3 gcm−3 was used to B



Article

Table 3. Experimental LLE Data (Mass Fraction) for the Water (1) + Cyclohexanol (2) + Solvents (3) System at 323.15 K under 101.3 kPaa organic phase solvent toluene

p-xylene

mesityl oxide

a

aqueous phase

w1

w2

w3

w1

w2

w3

D

S

0.0017 0.0014 0.0015 0.0009 0.0016 0.0013 0.0024 0.0028 0.0010 0.0010 0.0017 0.0022 0.0025 0.0029 0.0035 0.0038 0.0573 0.0555 0.0542 0.0636 0.0611 0.0708 0.0757 0.0771

0.0134 0.0286 0.0472 0.0638 0.0807 0.0975 0.1141 0.1667 0.0132 0.0289 0.0783 0.0952 0.1109 0.1271 0.1441 0.1592 0.0166 0.0314 0.0484 0.0640 0.0809 0.0949 0.1100 0.1235

0.9849 0.9700 0.9513 0.9352 0.9177 0.9013 0.8835 0.8306 0.9857 0.9701 0.9199 0.9026 0.8866 0.8700 0.8524 0.8371 0.9261 0.9131 0.8973 0.8724 0.8580 0.8343 0.8143 0.7994

0.9936 0.9909 0.9885 0.9870 0.9858 0.9845 0.9835 0.9792 0.9938 0.9904 0.9854 0.9835 0.9821 0.9809 0.9793 0.9786 0.9603 0.9589 0.9581 0.9561 0.9553 0.9531 0.9522 0.9507

0.0025 0.0048 0.0067 0.0086 0.0096 0.0109 0.0114 0.0144 0.0032 0.0063 0.0115 0.0131 0.0146 0.0155 0.0165 0.0172 0.0011 0.0023 0.0033 0.0050 0.0053 0.0073 0.0081 0.0093

0.0039 0.0043 0.0047 0.0044 0.0046 0.0046 0.0050 0.0064 0.0030 0.0033 0.0031 0.0033 0.0033 0.0036 0.0042 0.0042 0.0385 0.0388 0.0386 0.0390 0.0394 0.0396 0.0397 0.0400

5.40 5.95 7.03 7.43 8.42 8.96 9.98 11.58 4.15 4.61 6.79 7.24 7.61 8.20 8.73 9.24 14.78 13.46 14.56 12.88 15.25 13.02 13.63 13.33

3138 4309 4594 7977 5336 6904 4010 4118 3953 4633 3896 3274 2947 2763 2476 2391 248 233 259 194 239 175 171 164

Standard uncertainties, u, are u(T) = 0.01K, u(P) = 0.7 kPa, and u(w) = 0.003.

in the form of mass fraction. The ternary phase diagrams are shown in Figures 1, 2, 3, 4, 5, and 6. As we can see from the

Finally, the mixture was settled for at least 5 h and divided into two phases. The completed phase equilibria were kept at a fixed temperature (some preliminary experiments had been done and the results demonstrated that the period was adequate for the system to accomplish the phase separation and to attain the thermodynamic equilibria). The internal standard method was applied to determine the samples’ composition with isopropanol as the internal standard. When the ternary mixture formed two liquid layers and reached the phase equilibria, the samples were withdrawn carefully and analyzed by the GC,which was equipped with a Porapak N column (3 mm × 3 m) and a thermal conductivity detector (TCD). For the injector and detector, the temperature needed to be stabilized at 523.15 K. The temperature program began at 393.15 K, was sustained for about 1.5 min, it then increased to 523.15 K with a rate of 20 K min−1, and it was maintained at 523.15 K for 1 min, finally. The carrier gas, whose rate was 50 mL min−1, was hydrogen. For calibrating the GC, a sample with a known composition was used to check the composition of interest. Each sample of a certain concentration was performed more than three times, thus the average values, with a standard deviation less than 0.1%, were reported. The feed proportion was changed to obtain the series of the LLE data at different temperatures. The “Guide to the Expression of Uncertainty in Measurement (ISO)” standard was applied to calculate the composition’s standard uncertainty.26

Figure 1. Ternary phase diagram for the water + cyclohexanol + toluene system at 303.15 K. (☆) Feed composition; (○) experimental data; (△) NRTL model; and (□) UNIQUAC model.

figures, the feed point composition coincides tie lines very well, which is according to the lever rule. The result indicated the coincidence of the mass balance through experimental operations and testified the experimental data dependability.27 In addition, the experimental data for {water + cyclohexanol + toluene} were compared with the literature and were in better agreement.28

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RESULTS AND DISCUSSION Experimental LLE Data. The data for ternary systems {water + cyclohexanol + toluene}, {water + cyclohexanol + mesityl oxide}, and {water + cyclohexanol + p-xylene} obtained from the experiments are listed in Tables 2 and 3 with the value C



Article

Figure 2. Ternary phase diagram for the water + cyclohexanol + toluene system at 323.15 K. (☆) Feed composition; (○) experimental data; (△) NRTL model; and (□) UNIQUAC model.

Figure 5. Ternary phase diagram for the water + cyclohexanol + mesityl oxide system at 303.15 K. (☆) Feed composition; (○) experimental data; (△) NRTL model; and (□) UNIQUAC model.

Figure 3. Ternary phase diagram for the water + cyclohexanol + pxylene system at 303.15 K. (☆) Feed composition; (○) experimental data; (△) NRTL model; and (□) UNIQUAC model.

Figure 6. Ternary phase diagram for the water + cyclohexanol + mesityl oxide system at 323.15 K. (☆) Feed composition; (○) experimental data; (△) NRTL model; and (□) UNIQUAC model.

The distribution coefficient (D) as well as selectivity (S) were applied to estimate the rate of extraction agents for extracting cyclohexanol from the water solution, and they were calculated by the following equations: w2β D= w2α (1) S=

w2β /w1β w2α /w1α

(2)

w2α and w2β denote the contents of cyclohexanol in the aqueous and solvent phase severally (mass fraction). w1α and w1β denote the contents of water in the aqueous and solvent phase severally (mass fraction). The value of D and S that were obtained by the experimental LLE data are shown in Tables 2 and 3. As presented in these tables and figures, with the increase of cyclohexanol, the distribution coefficients tended to increase for toluene and p-xylene systems, but mesityl oxide was kept stable. The separating power of the extractants could be testified by selectivity. The selectivity of the solvents, which are presented

Figure 4. Ternary phase diagram for the water + cyclohexanol + pxylene system at 323.15 K. (☆) Feed composition; (○) experimental data; (△) NRTL model; and (□) UNIQUAC model.

D



Article

Table 4. Parameters of the Othmer−Tobias and Bachman Equations for the Water + Cyclohexanol + Solvents Systemsa Othmer−Tobias

Bachman

T/K

a1

b1

R2

a2

b2

R2

toluene 303.15K toluene 323.15 p-xylene 303.15 p-xylene 323.15K mesityl oxide 303.15K mesityl oxide 323.15K

−3.2327 −3.1499 −2.7622 −3.0263 −2.6966 −2.7043

0.4312 0.4489 0.5287 0.4782 0.1366 0.1926

0.9924 0.9967 0.9880 0.9970 0.9939 0.9902

0.0660 0.0754 0.1098 0.0864 0.0418 0.0597

0.9413 0.9316 0.8972 0.9201 1.0039 0.9772

0.9997 0.9996 0.9986 0.9997 0.9999 1

a 2

R is the correlation coefficient.

in Tables 2 and 3, were greater than 1, revealing the feasibility to extract cyclohexanol by these solvents. In addition, the effect of the temperature on our studied system was different in the range of our study that was obtained from Tables 2 and 3. The temperature effected p-xylene and toluene system’s LLE data very slightly, but for the mesityl oxide system, the effect is a bit significant. Quantitatively, the coherence of the experimental data was estimated via yhe Othmer−Tobias and Bachman equations, and relevant correlation equations are shown as follows:10,11 ⎛ 1 − w3β ⎞ ⎛ 1 − w1α ⎞ ⎟⎟ = a1 + b2 ln⎜ ln⎜⎜ ⎟ ⎝ w1α ⎠ ⎝ w3β ⎠

(3)

⎛ w3β ⎞ w3β = a 2 + b2⎜ ⎟ ⎝ w1α ⎠

(4) Figure 8. Bachman equation plots of the water + cyclohexanol + solvents (toluene + p-xylene + mesityl oxide) systems at 303.15 and 323.15 K.

w1α is the water content inside of the aqueous phase, and w3β denotes the content of the extractant in the organic phase (mass fraction). The results and relevant parameters, which were correlated through the Othmer−Tobias and Bachman equations, are shown in Table 4. The correlation factors, which were all approaching 1, demonstrated the experimental data consistency and reliability. The details of the correlations with the Bachman and Othmer−Tobias equations are also plotted in Figures 7 and 8. 3.2. Uncertainty Calculation. Two categories, which are named as “A” and “B”, were used to calculate the uncertainty.27

In the study, type A was applied to check each quantity q uncertainty, and the computational formula is shown as follows: n

s 2(qk ) =

∑ (qj − q ̅ )2 /(n − 1) j=1

(5)

s 2(q ̅ ) = s 2(qk )/n

(6)

u(wi) = s(Wi )

(7)

The standard deviation (s(qk)) of the experiment characterizes the dispersion of their mean q,̅ or the variability of the observed values qk is calculated. Therefore, for an import variable Xi, the Type A standard uncertainty u(wi) of its estimate is wi = W̅ i is u(wi) = s(W̅ i). 3.3. Experimental Correlation. The UNIQUAC model, which integrates the influence of the molecular size and shape,29 has correlated with many LLE systems successfully, including in mixtures containing ketones30 and alcohols.31−34 In consideration of the different molecular sizes and shapes of the employed chemicals, the UNIQUAC model was selected to correlate the studied systems. In addition, the NRTL model could correlate well with LLE mixtures with the accurate selection of the nonrandomness parameter αij;35 thus, theNRTL model was also considered. In this experiment, the nonrandomness parameters αij are shown in Table 5, which considered the polarity of the reagents, advice in the literature, and the improvement in the results.36,37

Figure 7. Othmer−Tobias equation plots of the water + cyclohexanol + solvents (toluene + p-xylene + mesityl oxide) systems at 303.15 and 323.15 K. E



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Table 5. Binary Energy Parameters of the NRTL and UNIQUAC Models for the Water (1) + Cyclohexanol (2) + Solvents (3) Systems NRTL parameters T/K toluene 303.15

toluene 323.15

p-xylene 303.15K

p-xylene 323.15K

mesityl oxide 303.15

mesityl oxide 323.15

a

UNIQUAC parameters

i−j

gij − gjja

gji − giia

α

RMSD/%

uij − ujja

uji − uiia

RMSD/%

1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3

3991.19 16921.41 −6375.92 4985.13 15204.91 −6600.37 5891.07 16875.68 −5951.71 6569.54 16921.26 −5693.19 12682.06 11479.35 −5030.09 14367.93 11691.09 −3508.74

12074.38 10105.17 13694.77 11577.71 10690.20 12974.68 25204.16 11035.90 12705.45 3695.41 11836.02 11359.18 −2783.83 340.17 6896.57 −2815.16 1653.07 5623.07

0.26 0.26 0.26 0.26 0.26 0.26 0.27 0.27 0.27 0.28 0.28 0.28 0.23 0.23 0.23 0.27 0.27 0.27

0.08

−184.56 2089.57 −770.65 −1611.86 −102.22 −1557.91 −653.05 1045.73 −1642.19 −274.69 786.31 −1951.81 2195.70 610.59 −713.35 5098.24 822.76 136873.4

74181.57 6056.96 2677.51 120499.37 12089.50 −3423.16 10625.49 8134.23 3726.49 3694.79 8901.81 3825.69 −862.70 2731.40 676.89 687.72 2700.27 1817.90

0.05

0.15

0.09

0.08

0.06

0.16

0.06

0.067

0.066

0.13

0.138

The unit of the parameters is J/mol.

Table 6. UNIQUAC Structural Parameters (r and q)

The correlation quality through the NRTL and UNIQUAC models were evaluated via the root-mean-square deviation (RMSD), and relevant equation is listed as follows: 1/2 ⎧ n 2 3 (w exp − w cal)2 ⎫ ⎪ ⎪ ijk ijk ⎬ RMSD = ⎨∑ ∑ ∑ ⎪ ⎪ 6n ⎩k=1 j=1 i=1 ⎭

(8)

n indicates tie line number, wexp denotes the experimental data that are expressed in the mass fraction, and wcal expresses the calculated data. The subscripts i, j, and k represent the component, phase, and tie line, respectively. The minimization of the objective function (OF) was used to generate the binary interaction parameters (gij − gjj and gji − gii, uij − ujj and uij − ujj):38 n

OF =

2

r

q

0.9200 4.2740 4.6578 3.9228 4.4632

1.4000 3.2840 3.5360 2.9700 3.8600

a

Taken from ref 39. bTaken from ref 40. cTaken from ref 41. dTaken from ref 42

4. CONCLUSION The LLE data for the ternary systems {water + cyclohexanol + toluene}, {water + cyclohexanol + mesityl oxide}, and {water + cyclohexanol + p-xylene} were successfully obtained experimentally at 303.15 and 323.15 K under 101.3 kPa. The Othmer−Tobias and Bachman equations were applied for checking the experimental data, and the details of the linearity for different systems demonstrated the coherence and accuracy of our data. The distribution coefficient and selectivity were also adopted to evaluate the separating power of the extractants. The NRTL and UNIQUAC models were applied for correlating the LLE data and produced better representations since the RMSD value was less than 0.2%. In addition, the relevant binary interaction parameters were also generated during the correlation process. All data obtained in the study enriched the database, which was used in the process of extracting cyclohexanol.

3

∑ ∑ ∑ (xijkexp − xijkcal)2 k=1 j=1 i=1

component watera cyclohexanola p-xyleneb toluenec mesityl oxided

(9)

The relevant characters n, wexp, wcal, i, j, and k in the OF equation denote the same meanings as those in the RMSD equation. The data that were correlated via the UNIQUAC and NRTL models are shown in Figures 1−6. As shown in these figures, the data of the calculated fitted well with the experimental, which indicated that these two models were appropriate to correlate the process for extracting cyclohexanol. The values of RMSD for the different systems, which range between 0.0006 and 0.002, are shown in Table 5. The minimization of RMSD indicated that these models were ideal for correlating the studied system LLE data. The UNIQUAC structural parameters, r (the number of segments per molecules) and q (the relative surface area per molecules), for the pure components were obtained from literature and are listed in Table 6.39−42 The binary interaction parameters, which are listed in Table 5, were generated through the regression of the data that were obtained by the experimental procedures and were correlated via the NRTL and UNIQUAC models.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Yingmin Yu: 0000-0002-0444-232X Qingsong Li: 0000-0003-1425-8822 Notes

The authors declare no competing financial interest. F



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(42) 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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