Liquid–Liquid Equilibria for the Ternary Systems of Water +

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Liquid−Liquid Equilibria for the Ternary Systems of Water + Thioglycolic Acid + 2‑Ethyl-1-hexyl Thioglycolate and Water + 2‑Ethyl-1-hexyl Thioglycolate + 2‑Ethyl-1-hexanol at 293.15, 303.15, and 313.15 K under 101 kPa Xiaoda Wang, Yuan Gao, Chaoqun Li, Zhixian Huang, and Ting Qiu*

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Fujian Universities Engineering Research Center of Reactive Distillation, College of Chemical Engineering, Fuzhou University, Fuzhou 350116, Fujian, China S Supporting Information *

ABSTRACT: Liquid−liquid equilibrium data were determined for the two ternary systems of water + thioglycolic acid (TGA) + 2-ethyl-1-hexyl thioglycolate (ETE) and water + 2ethyl-1-hexyl thioglycolate (ETE) + 2-ethyl-1-hexanol (EHL) at 293.15, 303.15, and 313.15 K under 101 kPa. The nonrandom two-liquid (NRTL) and universal quasi-chemical (UNIQUAC) activity coefficient models were used to correlate the experimental LLE data. The LLE data calculated by the NRTL and UNIQUAC models were in good agreement with the experimental ones.

1. INTRODUCTION 2-Ethyl-1-hexyl thioglycolate (ETE) is a powerful thermal stabilizer for polyvinyl chloride (PVC) production and a highly selective reagent for the solvent extraction of metal ions.1−3 The esterification of thioglycollic acid (TGA) with 2-ethyl-1hexanol (EHL) is a promising industrial route to produce ETE. Figure 1 gives the chemical equation for this esterification

the product of the prior reactor is used as an extraction solvent instead of pure EHL. The product of the last reactor is sent into a distillation column to separate ETE from the EHL− water mixture by their boiling point difference. The EHL− water mixture is separated in an extractor because of their low mutual solubility. The liquid−liquid equilibrium (LLE) data are necessary for the simulation and optimization of industrial processes,6−13 such as the technological process in Figure 2. However, to our best knowledge, the LLE data for the system of water + TGA + ETE + EHL have not been reported. In this work, the LLE data for the two ternary systems water + TGA + ETE and water + ETE + EHL were measured at 293.15, 303.15, and 313.15 K under atmospheric pressure. Both the nonrandom two-liquid (NRTL)14 and universal quasi-chemical (UNIQUAC)15 activity coefficient models were applied to correlate the LLE data by Aspen Plus 8.4.

Figure 1. Chemical equation for the esterification reaction of TGA with EHL.

reaction, which is a reversible reaction with water as a byproduct. By the most widely used method of TGA production, an aqueous solution containing about 10% (mass fraction) TGA was obtained. Extraction was an energy-efficient method to separate TGA from water.4,5 The reactant EHL was a suitable solvent for the extraction of TGA from aqueous solution due to its low solubility in water and high intersolubility with TGA. In industry, the operation units of extraction and reaction were jointly used to conduct the TGA separation and esterification reaction, as shown in Figure 2. In the first extractor, EHL acts as an extraction solvent and separates TGA from water. The extraction phase is sent into the following reactor to conduct the EHL−TGA esterification reaction. More than 99% conversion of TGA can be realized in the reactor at excess EHL−TGA mole ratio, since this esterification reaction is a reversible one with high equilibrium conversion. In the following extractor−reactor combinations, © XXXX American Chemical Society

2. EXPERIMENTAL SECTION 2.1. Chemicals. The major details of the chemicals used are listed in Table 1. TGA, ETE, and EHL were purchased from Shanghai Aladdin Chemicals Co., Ltd. The purity of TGA was checked by acid−base titration. Gas chromatography (GC) was applied to check the purities of ETE and EHL, and no obvious peak of impurity was detected. The initial mass purities of these chemicals were shown in Table 1. TGA was used without further purification for its major impurity was Received: July 17, 2018 Accepted: December 20, 2018

A

DOI: 10.1021/acs.jced.8b00619 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Figure 2. Industrial process for the production of ETE with TGA aqueous solution and pure EHL as raw material.

Table 1. Specifications of Chemicals chemicals (abbreviation)

CAS number

formula

initial purity (mass fraction)

thioglcolic aicd (TGA) 2-ethyl-1-hexyl thioglycolate (EHL) 2-ethyl-1-hexanol (EHL) water

68-11-1 7659-86-1 104-76-7 7732-18-5

C2H4O2S C10H20O2S C8H18O H2O

0.980a 0.980b 0.995b

purification method

final purity (mass fraction)

distillation distillation

0.980a 0.995b 0.998b

a

Acid−base titration. bGas chromatography.

water, which was contained in both of these ternary systems measured. ETE and EHL were purified by distillation. Deionized water was made in our laboratory. 2.2. Apparatus and Procedure. The experimental LLE data of the water + TGA + ETE and water + ETE + EHL ternary systems were determined at temperatures of 293.15, 303.15, and 313.15 K at atmospheric pressure. The pressure gauge showed that the local atmospheric pressure is about 101 kPa. Since the small fluctuations in atmospheric pressure do not change the liquid−liquid equilibrium of these systems, the experimental pressure was not accurately controlled and determined. The schematic of the apparatus applied to conduct the LLE experiment is shown in Figure 3. The apparatus includes a jacketed glass cell, a condenser pipe, a magnetic agitator, and a thermometer. Although the loss of the chemicals due to volatilization is negligible, the condenser pipe was still used. The temperature of the glass cell was controlled by a thermostatic water bath with an accuracy of ±0.1 K. This apparatus was used to determine LLE data for other LLE systems in our previous works.16,17 The liquid mixture was agitated vigorously for approximately 1 h to reach liquid− liquid phase equilibrium and left to settle for another 2 h to ensure complete liquid−liquid phase separation. Different LLE tie-line data were detected by varying the chemical composition and system temperature. Samples were withdrawn from upper and lower phases with long needle syringes, respectively. 2.3. Analytical Method. A Thermo gas chromatograph (Trace 1300) with a 30 m capillary column (diameter of 0.32 mm and film thickness of 0.25 μm) was applied to analyze the concentrations of ITE and ITL in aqueous and organic phases. The temperature programming of GC was set as follows: the initial oven temperature was held at 393.15 K for 1 min,

Figure 3. LLE experimental apparatus: 1 - condensing tube, 2 - inlet of refrigeration water, 3 - jacketed glass cell, 4 - sampling port of the organic phase, 5 - inlet of thermostatic water, 6 - outlet of refrigeration water, 7 - thermometer, 8 - thermometer pipe, 9 - outlet of thermostatic water, 10 - sampling port of the aqueous phase, 11 magnetic stirrers.

subsequently increased at a rate of 60 K·min−1 to 453.15 K, then increased at a rate of 20 K·min−1 to 523.15 K, then B

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increased at a rate of 15 K·min−1 to 573.15 K, and finally kept at 573.15 K for 2 min. The temperatures of the injector and the detector were maintained at 593.15 K. The high-purity hydrogen (99.999%) was used as a carrier gas with a constant flow rate of 0.58 mL·s−1. The quantitative analysis of ETE and EHL was achieved by the internal standard method with cyclohexanone as the internal standard substance. The samples were diluted 50 times with acetone before being injected into GC. The composition of TGA was determined by the method of acid−base titration. Water concentration was measured by a Mettler Toledo V30 KF Coulometer.

3. RESULTS AND DISCUSSION 3.1. Experimental LLE Data. The determined LLE data for the water + TGA + ETE system are tabulated in Table 2, Figure 4. LLE phase diagrams (mole fraction) for the water (1) + TGA (2) + ETE (3) ternary system at 293.15 (■), 303.15 (●), and 313.15 (▲) K under atmospheric pressure. : Tie-line.

Table 2. Experimental LLE Data (Mole Fraction) for the Water (1) + TGA (2) + ETE (3) Ternary System, Distribution Coefficients of Water (D1) and TGA (D2), and Separation Factors (S) at T = 293.15, 303.15, and 313.15 K under P = 101 kPaa,b aqueous phase

organic phase

xA1

xO1

xA2

0.9993 0.8207 0.7507 0.5707 0.4505 0.3884 0.3479

0.0000 0.1751 0.2419 0.4018 0.4894 0.5227 0.5372

0.9995 0.8709 0.8239 0.5693 0.4484 0.3981 0.3569

0.0000 0.1270 0.1727 0.4047 0.4930 0.5209 0.5371

0.9996 0.8002 0.7328 0.5620 0.4488 0.3955 0.3634

0.0000 0.1962 0.2605 0.4122 0.4949 0.5242 0.5367

xO2

T = 293.15 K 0.1230 0.0000 0.1224 0.0449 0.1219 0.0616 0.1220 0.1248 0.1252 0.1983 0.1312 0.2598 0.1399 0.3158 T = 303.15 K 0.1300 0.0000 0.1294 0.0351 0.1289 0.0448 0.1271 0.1307 0.1302 0.2126 0.1358 0.2694 0.1466 0.3335 T = 313.15 K 0.1370 0.0000 0.1351 0.0513 0.1341 0.0703 0.1326 0.1410 0.1360 0.2294 0.1451 0.3045 0.1573 0.3628

D1

D2

S

0.149 0.162 0.214 0.278 0.338 0.402

0.256 0.254 0.311 0.405 0.497 0.588

1.72 1.57 1.45 1.46 1.47 1.46

0.149 0.156 0.223 0.290 0.341 0.411

0.277 0.259 0.323 0.431 0.517 0.621

1.86 1.66 1.45 1.49 1.52 1.51

0.169 0.183 0.236 0.303 0.367 0.433

0.262 0.270 0.342 0.464 0.581 0.676

1.55 1.48 1.45 1.53 1.58 1.56

ETE binary system improved not only the solubility of water in the organic phase but also the solubility of ETE in the aqueous phase, since TGA is completely miscible with both water and ETE. With the temperature increased from 293.15 to 313.15 K, the solubility of ETE in water increased from 0.1230 to 0.1370 mol/mol, while the variation of water solubility in ETE is too minor to be distinguished by our analysis method. The liquid− liquid two-phase region changed slightly with the variation of temperature, as shown in Figure 4, which suggests that changing temperature is not an effective means to vary the mutual solubility of the ternary water + TGA + ETE liquid− liquid system. Table 3 lists the determined LLE data for the water + ETE + EHL system, and Figure 5 illustrates the corresponding triangle phase diagram. As shown in Figure 5, water is partially miscible with both ETE and EHL, while EHL + ETE is a completely miscible system. It implies the ternary system of water + ETE + EHL exhibits type II LLE behavior.18 For the water + ETE system, the mass fractions of water and ETE in organic and aqueous phases are 0.1204 and 0.0012 mol/mol at 293.15 K, respectively, as listed in Table 3, suggesting that the solubility of EHL in water is much lower than that of water in EHL. With the temperature increased from 293.15 to 313.15 K, the solubility of water in EHL increases from 0.1204 to 0.1651 mol/mol, while the tiny variation of the EHL solubility in water is difficult to be determined by our analysis method. It manifests that the increase of temperature contributes more in improving the solubility of water in EHL than that of EHL in water. The liquid−liquid two-phase region shrinks slightly with the increase of temperature, as shown in Figure 5, which implies that the mutual solubility of the water + ETE + EHL system is not sensitive to temperature variation. We compared the liquid−liquid phase equilibria data measured in our work and those reported in the literature19−25 for the water−EHL system, as shown in Figure 6. Our data coincide well with most of the data reported in the literature, suggesting the reliability of our experimental method. The distribution coefficient (Di) and separation factor (S) were calculated for the two ternary systems to evaluate the extraction performances of ETE and EHL:

a Standard uncertainties are u(P) = 0.1 kPa, u(T) = 0.1 K, and u(x) = 0.003. bw represent mass fraction; the superscripts “A” and “O” represent aqueous and organic phases, respectively; and the subscript indicates the component.

and the corresponding triangle phase diagram is presented in Figure 4. As shown in Figure 4, the binary mixture of water + ETE is a partially miscible system, while TGA is completely miscible with both water and ITE. It indicates the ternary system of water + TGA + ETE exhibits type I LLE behavior.18 For the water + ETE binary system, the mass fractions of water and ETE in organic and aqueous phases are 0.1230 and 0.0007 mol/mol at 293.15 K, respectively, as illustrated in Table 2. It suggests that the solubility of ETE in water is much lower than that of water in ETE. The addition of TGA into the water +

Di = C

xiO xiA

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Table 3. Experimental LLE Data (Mole Fraction) for the Water (1) + ETE (2) + EHL (3) Ternary System, Distribution Coefficients of Water (D1) and ETE (D2), and Separation Factors (S) at T = 293.15, 303.15, and 313.15 K under P = 101 kPaa,b aqueous phase xA1

organic phase xA2

xO1

0.9988 0.9988 0.9988 0.9988 0.9988 0.9988 0.9988 0.9988

0.0000 0.0001 0.0004 0.0005 0.0006 0.0007 0.0008 0.0010

0.1204 0.1148 0.1091 0.1062 0.1062 0.1060 0.1058 0.1067

0.9988 0.9988 0.9989 0.9988 0.9988 0.9989 0.9989 0.9988 0.9988

0.0000 0.0001 0.0003 0.0004 0.0005 0.0006 0.0007 0.0008 0.0010

0.1376 0.1310 0.1249 0.1204 0.1194 0.1174 0.1160 0.1145 0.1113

0.9990 0.9990 0.9989 0.9989 0.9988 0.9988 0.9988 0.9988

0.0000 0.0002 0.0004 0.0005 0.0006 0.0007 0.0009 0.0010

0.1651 0.1440 0.1256 0.1207 0.1139 0.1107 0.1110 0.1159

xO2 T = 293.15 K 0.0000 0.1728 0.4388 0.4800 0.5703 0.6410 0.7004 0.8046 T = 303.15 K 0.0000 0.1513 0.3166 0.4243 0.4674 0.5642 0.6227 0.6925 0.8047 T = 313.15 K 0.0000 0.1911 0.3853 0.4480 0.5510 0.6322 0.7285 0.7942

D1

D2

S

0.115 0.109 0.106 0.106 0.106 0.106 0.107

1226.530 971.335 898.486 903.791 884.342 862.592 815.186

10668.58 8889.68 8446.96 8504.05 8330.59 8141.85 7629.16

0.131 0.125 0.121 0.120 0.118 0.116 0.115 0.111

1190.751 1066.807 957.885 949.468 939.066 916.573 888.056 811.368

9079.22 8534.41 7945.87 7943.20 7988.18 7890.39 7749.75 7282.49

0.144 0.126 0.121 0.114 0.111 0.111 0.116

1018.517 906.189 883.523 851.522 860.261 837.029 794.222

7066.37 7204.88 7309.92 7464.54 7761.80 7530.75 6847.42

Standard uncertainties are u(P) = 0.1 kPa, u(T) = 0.1 K, and u(x) = 0.004. bw represent mass fraction; the superscripts “A” and “O” represent aqueous and organic phases, respectively; and the subscript indicates the component.

a

Figure 5. LLE phase diagrams (mole fraction) for the water (1) + ETE (2) + EHL (3) ternary system at 293.15 (■), 303.15 (●), and 313.15 (▲) K under atmospheric pressure. : Tie-line.

S=

D2 D1

ETE in the case of the water + ETE + EHL system. The calculated values of D1, D2, and S are listed in Tables 2 and 3 for the systems of water + TGA + ETE and water + ETE + EHL, respectively. For the system of water + TGA + ETE, all

(2)

S is the separation factor between water and TGA in the case of the water + TGA + ETE system and between water and D

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interaction parameters bij for the two models were obtained by correlating the experimental LLE data with Aspen Plus 8.4. Aspen Plus software has the robust function of correlating the binary interaction parameters of the thermodynamic model by VLE and LLE data.26,27 The objective function for correlation was defined as follows: n

OF =

n

∑ ∑ [(xikO,exp − xikO,cal)2 + (xikW,exp − xikW,cal)2 ] k=1 i=1

(3)

The superscripts “exp” and “cal” represent experimental and calculated data, respectively. k is the number of tie-lines. The regressed binary interaction parameters for the two ternary systems are listed in Table 4. The dependences of these parameters on temperature are shown in Table 5 in the form of a polynomial. The root-mean-square deviation (RMSD) values were calculated to evaluate the deviation of calculated LLE data from the experimental ones. The expression of RMSD is defined as

Figure 6. Comparison of our experimental data with those reported in the literatur19−25 for the water−EHL liquid−liquid two-phase system.

of the values of S are slightly greater than 1, ranging from 1.45 to 1.86. It implies that ETE, one of the products of the TGA− EHL esterification reaction, is not a good solvent to extract TGA from the aqueous solution. For the system of water + ETE + EHL, all of the calculated values of S are in the range 6847.42−10668.58, far greater than 1. It indicates that EHL is a solvent with excellent extraction performance to separate ETE from water. The superior ability of EHL to extract ETE from water is conducive to limiting the entrance of ETE into the aqueous phase, if the product of the reactor for the EHL− TGA esterification reaction was used as the extraction solvent. 3.2. Correlation of LLE Data. The NRTL and UNIQUAC activity coefficient models were adopted to correlate the experimental LLE data for the ternary systems of water + TGA + ETE and water + ETE + EHL. The details about these two models are given in the Supporting Information. The

RMSD M

=

3

∑k = 1 ∑i = 1 [(xikO,exp − xikO,cal)2 + (xikA,exp − xikA,cal)2 ] 6M (4)

The values of RMSD are shown in Table 4. All of the RMSDs are less than 0.0200, indicating the experimental LLE data could be correlated well with both the NRTL and UNIQUAC models. More detailed comparisons between the experimental and calculated data are given in Tables S2 and S3 in the Supporting Information.

4. CONCLUSIONS The liquid−liquid equilibrium data of water + thioglycolic acid (TGA) + 2-ethyl-1-hexyl thioglycolate (ETE) and water +

Table 4. NRTL and UNIQUAC Parameters for the Two Ternary Systems of Water + TGA + ETE and Water + ETE + EHL at 293.15, 303.15, and 313.15 Ka NRTL T/K 293.15

303.15

313.15

293.15

303.15

313.15

components i−j

bij

1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3

485.37 17665.68 2948.11 1317.70 19101.42 3006.57 −550.62 18145.87 4950.81

1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3

14528.65 13359.11 7224.15 15082.52 14016.46 8288.36 15423.18 15010.73 5687.67

UNIQUAC αij

bji

Water + TGA + ETE 25409.21 0.3 1367.158 0.2 4357.46 0.3 25548.06 0.3 1484.98 0.2 4935.55 0.3 13184.17 0.3 1228.61 0.2 5077.17 0.3 Water + ETE + EHL 4517.43 0.3 4058.72 0.3 −3421.36 0.3 4545.74 0.3 3874.78 0.3 −3655.30 0.3 4876.16 0.3 3870.26 0.3 −2521.01 0.3

RMSD

bij

bji

RMSD

0.0049

484.65 −942.06 653.81 6918.09 −803.74 377.42 11649.40 −1403.70 569.90

1784.60 −3388.90 −2387.63 −27390.3 −3853.17 351.29 −4654.12 −3422.81 4913.22

0.0137

0.0042

0.0076

0.0188

0.0160

0.0180

204.66 −204.89 −3061.68 203.82 −284.281 −3657.52 212.50 −478.87 −1765.35

−5572.49 −4354.74 1796.26 −5766.18 −4183.87 2007.559 −5722.45 −3887.45 1136.75

0.0111

0.0136

0.0193

0.0167

0.0153

The unit of bij is J·mol−1.

a

E

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Table 5. Dependence of Interaction Parameters on Temperature: bij/R = AT2 + BT + Ca water + TGA + ETE model NRTL

bij

bji

UNIQUAC

bij

bji

A B C A B C A B C A B C

water + ETE + EHL

1−2

1−3

2−3

1−2

1−3

2−3

−1.624 978.50 −147213 −7.519 4485.30 665642 −1.024 687.79 −113596 31.219 −18967 3000000

−1.438 874.81 −130740 −0.225 135.61 −20250 −0.444 266.42 −40058 0.538 −326.41 49043

1.134 −675.56 100934 −0.263 163.47 −24841 0.282 −171.47 26113 1.096 −620.81 87486

−0.128 83.12 −11600 0.182 −108.00 16590 0.006 −3.42 536.45 0.143 −87.48 12702

0.203 −112.91 17295 0.108 −66.55 10725 −0.069 40.36 −5902 0.076 −42.97 5584

−0.640 394.44 −59760 0.823 −493.48 73539 1.496 −899.40 134705 −0.651 390.60 −58362

The units of bij and T are J·mol−1 and K, respectively. Ideal gas constant R = 8.314 J·mol−1·K−1.

a

■

isooctyl-ethyl-1-hexyl thioglycolate (ETE) + 2-ethyl-1-hexanol (EHL) were determined at 293.15, 303.15, and 313.15 K under atmospheric pressure. The binary systems of water + ETE and water + EHL are partially miscible, while the binary systems of water + TGA, TGA + ETE, and ETE + EHL are completely miscible. It indicates the ternary systems of water + TGA + ETE and water + ETE + EHL conform to type I and II ternary diagrams, respectively. The LLE data were correlated with the NRTL and UNIQUAC models by Aspen Plus 8.4. The values of RMSD were less than 0.0200, indicating that these two models could describe well the nonideality of the two ternary systems.

■

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ASSOCIATED CONTENT

* Supporting Information S

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.8b00619.

■

REFERENCES

Description of the NRTL and UNIQUAC models and tables showing values of ri and qi for each component, experimental and calculated LLE data (mole fraction) for the water (1) + TGA (2) + ETE (3) ternary system at T = 293.15, 303.15, and 313.15 K under 101 kPa, and experimental and calculated LLE data (mole fraction) for the water (1) + ETE (2) + EHL (3) ternary system at T = 293.15, 303.15, and 313.15 K under 101 kPa (PDF)

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Xiaoda Wang: 0000-0002-2519-4839 Ting Qiu: 0000-0001-7737-8640 Funding

We acknowledge the financial support for this work from the National Natural Science Foundation of China (No. 21706034), the Natural Science Foundation of Fujian Province (Nos. 2016J05036 and 2017J01417), and the Student Research Training Program of Fuzhou University (No. 201710386062). Notes

The authors declare no competing financial interest. F

DOI: 10.1021/acs.jced.8b00619 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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DOI: 10.1021/acs.jced.8b00619 J. Chem. Eng. Data XXXX, XXX, XXX−XXX