LiquidâLiquid Equilibrium for the Ternary System of 3

Article pubs.acs.org/jced

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

Liquid−Liquid Equilibrium for the Ternary System of 3‑Mercaptopropionic Acid + Water + Trichloromethane Chengli Tang,†,‡ Yan Bao,§ Geng Hu,‡ Lichun Dong,‡,⊥ and Limei Zhang*,‡,§ †

Chongqing Chemical Industry Vocational College, 401220, Chongqing, P. R. China School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China § Green Fine Technology Co. Ltd, Chongqing 404100, P. R. China ⊥ Key Laboratory of Low-grade Energy Utilization Technologies & Systems of the Ministry of Education, Chongqing University, Chongqing, 40004, P. R. China Downloaded via OCCIDENTAL COLG on April 29, 2019 at 18:45:34 (UTC). See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles.

‡

ABSTRACT: Liquid−liquid equilibrium (LLE) for the ternary system of 3-mercaptopropionic acid (3-MPA) + water + trichloromethane (TCM) was measured at temperatures of (303.2, 313.2, and 323.15) K under atmospheric pressure, and the corresponding phase diagrams were illustrated. Moreover, it was demonstrated that the presence of NaCl in the system can promote the separation of the two liquid phases, which favors the extraction of 3-MPA from water by TCM. The experimental data were correlated by using the nonrandom two-liquid (NRTL) equation, which showed that the calculated data are in good agreement with the experimental data, and the NRTL model can accurately predict the LLE of the ternary system at specific temperatures using the obtained interaction energy parameters.

1. INTRODUCTION 3-Mercaptopropionic acid (3-MPA) is a critical intermediate for the synthesis of O-desmethylvenlafaxine (an important antidepressant)1 and a raw material for manufacturing various crosslinking agents, resin additives, plastic stabilizers, etc.2−4 The most common industrial process to produce 3-MPA is from sodium hydrosulfide and acrylonitrile, during which, the aqueous solution of 3-MPA is obtained via two reaction pathways.5−10 In the first pathway, acrylonitrile reacts with sodium hydrosulfide to form 3-mercaptopropionitrile via an addition reaction, which was then hydrolyzed to 3-MPA under an acidic condition; while in the second pathway, the synthesized 3-mercaptopropionitrile further reacts with acrylonitrile to 3, 3′-dithiodipropionic acid, which is subsquently reduced to 3-MPA by using reductants such as Fe or Zn powders. The raw product obtained after the reation is the aqueous solution of 3-MPA containg the impurities of NaCl, thiodipropionetrile, etc. The liquid−liquid extraction process was then employed to obtain the final product of high-purity. The reported extractants include acetic ether, chloroform, trichloromethane (CHCl3, TCM) etc.; however, the systematic studies on the liquid−liquid equilibrium of the related ternary systems that is essential not only for the production of 3-MPA © XXXX American Chemical Society

using liquid−liquid extraction, but also the treatment of waster water containing 3-MPA, are surprisely scarce in the literature.11,12 In this paper, the LLE data of the ternary system of 3-MPA + water + TCM were first measured at different temperatures (303.2, 313.2 and 323.2) K under atmospheric pressure, and the corresponding phase diagrams were illustrated. Since NaCl always exists in the aqueous solution of 3-MPA obtained from the industrial reaction process of sodium hydrosulfide with acrylonitrile, the LLE data of the ternary system containing different concentration of of NaCl (0, 2, 6 wt %) were also measured at 313.2 K under atmospheric pressure. The experimental data were first verified by the Hand and Othmer−Tobias equations,3,4 and then correlated by using the nonrandom two-liquid (NRTL) model.13

2. EXPERIMENTAL SECTION 2.1. Materials. As showed in the Sample Description Table (Table 1), 3-mercaptopropionic acid (analytical reagent, AR, > Received: December 11, 2018 Accepted: April 9, 2019

A

DOI: 10.1021/acs.jced.8b01187 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Sample Description Table chemical name

source

initial mole fraction purity

purification method

final mole fraction purity

analysis method

3-mercaptopropionic acid trichloromethane acetone K2Cr2O4 NaCl Na2S2O3 H2SO4 HCl KI soluble starch

Alfa Aesar Kelong Chemical Chuandong Chuandong Chuandong Chuandong Chuandong Chuandong Kelong Kelong

0.990 0.998 0.995 0.995 0.995 0.995 0.985 0.367 0.995 0.991

distillation

0.9991

ITa GCb GC titration argentometry IT titration titration argentometry anthrone method

a

Iodine titration. bGas−liquid chromatography.

calculated to be 0.67 %, demonstrating a good repeatability of the analyzing method. The mass concentration of 3-MPA in the organic phase (wI1) and aqueous phase (wII1) was determined by using an iodometric titration method with starch serving as the indicator.14 Before each measurement, 2 g of the aqueous phase or organic phase was diluted using 150 mL of water and TCM, respectively. High efficiency liquid chromatography (HPLC) was demonstrated to be accurate in analyzing 3MPA1,15Z; however, it is not applicable in this study since the existence of Cl− anions in the ternary system could result in equipment corrosion. The same as for the analysis of TCM, each sample was also analyzed at least three times, and the average values were reported. The corresponding maximum relative deviation was calculated to be 0.61%. It is noteworthy that we have also tried to determine the concentration of 3MPA using the methods of GC and acid−base titration, and verified the better accuracy of the iodometric titration method. According to the measured data, the phase diagrams with the tie-lines of the ternary system at different conditions were w illustrated, and the distribution coefficient (D = w I1 ) of 3-

99 wt %) was purchased from Alfa Aesar Chemical Co. Ltd. (China), and was further purified by using vacuum distillation. The purity of 3-MPA after the purification was measured to be 99.91 wt % by using a iodimetric titration method. Trichloromethane (chromatographic grade), the purity of which was measured to be higher than 99.8 wt % by GC (gas chromatography), was purchased from Kelong Chemical Reagent company (Chengdu, China). Acetone (AR, purity > 99.5 wt %) was purchased from Chuandong (Chongqing, China) Chemical Reagent company. Other chemicals used in this work, K2Cr2O4, NaCl, Na2S2O3, concentrated H2SO4, hydrochloric acid (Chuandong Chemical Reagent company, Chongqing, China), and KI, soluble starch (Kelong Chemical Reagent company) are all analytical grade and were used without further purification. All the water used in the experiments was deionized water (conductivity < 0.5 us/cm) that was self-made in the laboratory. 2.2. Experimental Procedure. The LLE of the ternary system was performed in a self-made glass mixer equipped with a SHA-C thermostatic water-bath oscillator (Huapuda, Changzhou, Jiangsu Province, China). Then, different amounts of 3-MPA, TCM, water, and NaCl, measured by using an electronic balance (FA2004 model, accuracy = ±0.0001 g, Shanghai Hengping Scientific Instrument Co. Ltd., China), were added and mixed in a glass bottle (50 mL), which was then sealed and put into the glass mixer. After the mixture was heated to the expected temperature (measured by a precision and calibrated thermometer, ±0.1°C), and oscillated for 4 h, it was allowed to rest for another 4 h, and the resulting mixture was separated into two phases. The organic phase and the aqueous phase (2 g) were, respectively, carefully sampled for component analyses without disturbing the equilibrium. The mass concentration of TCM in both the organic phase (wI3) and aqueous phase (wII3) were analyzed using a GC (GC7900, Shanghai Tian Mei Scientific Instruments Co. Ltd., China) equiped with a ϕ 2 mm × 3000 mm Porapak Q column and a flame ionization detector (FID). The temperature of the injector and detector port was kept at 523.15 K, while the column room temperature was controlled at 473.15 K. Moreover, nitrogen was used as the carrier gas, and the precolumn pressure was set to be 0.3 MPa. An internal standard method was used to quantify the mass concentration of TCM by using acetone as the internal standard, and a standard curve between the mass ratio of TCM and acetone versus their GC peak ratio was determined first. Each sample was analyzed at least three times, and the average values were reported. The maximum relative deviation of the measured data was

II1

MPA was calculated. Since the operating temperature for the industrial extration of 3-mercaptopropionic acid is usually around 313.2 K, the LLE data for the ternary system were measured at temperatures of (303.2, 313.2, and 323.2) K under atmospheric pressure, and those for the system with the addition of NaCl were measured at 313.2 K. 2.3. Verification of the Experimental Data. The reliability and consistence of the experimental tie-line data were verified by using the Hand3 equation (eq 1) and Othmer−Tobias4 equation (eq 2), the effectiveness of which to ascertain the experimental LLE data was validated by a large number of systems.16 ij w yz ij w yz lnjjj I1 zzz = A + B lnjjj II1 zzz jw z j wI3 z k II2 { k {

ij 1 − wI3 yz i y zz = A′ + B′ lnjjj 1 − wII2 zzz lnjjj jj w zz j wI3 zz II2 k { k {

(1)

(2)

where, wI2 and wII2 are mass concentration of water in the organic phase and aqueous phase. A, B, A′, and B′ are parameters that can be calculated according to the least square method. 2.4. LLE Correlation Using the NRTL Model. For experimental data to be applied in engineering calculations, it is B



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Table 2. LLE Data of the Ternary Systems at Different Temperatures and 99.2 kPaa organic phase

aqueous phase

experimental data

calculated data

experimental data

calculated data

wcal I1

wcal 13

wexp II1

wexp II3

wcal II1

wcal II3

RMSDt

0.0508 0.9468 0.1067 0.8890 0.1705 0.8224 0.2326b 0.7518b 0.2909 0.6796 0.3506 0.6086 0.4005 0.5117 0.4518b 0.4279b total average RMSD

0.0498 0.1068 0.1663 0.2258b 0.2848 0.3399 0.3928 0.4496b

0.9472 0.8880 0.8243 0.7569b 0.6861 0.6152 0.5420 0.4549b

T = 303.2 K 0.0538 0.0920 0.1323 0.1677b 0.2042 0.2420 0.2763 0.3196b

0.0046 0.0056 0.0063 0.0078b 0.0113 0.0168 0.0243 0.0385b

0.0530 0.0935 0.1331 0.1717b 0.2106 0.2492 0.2906 0.3428b

0.0043 0.0057 0.0074 0.0094b 0.0120 0.0151 0.0194 0.0268b

0.0008 0.0011 0.0023 0.0046b 0.0053 0.0066 0.0173 0.0190b 0.0097


0.0452 0.1014 0.1689 0.2181b 0.2715 0.3250 0.3725 0.4195b

0.9482 0.8877 0.8102 0.7523b 0.6867 0.6171 0.5508 0.4789b

T = 313.2 K 0.0554 0.1014 0.1493 0.1891b 0.2309 0.2781 0.3252 0.3721b

0.0046 0.0058 0.0072 0.0097b 0.0141 0.0331 0.0412 0.0638b

0.0550 0.0987 0.1452 0.1912b 0.2401 0.2924 0.3410 0.3910b

0.0043 0.0060 0.0090 0.0119b 0.0168 0.0242 0.0341 0.0489b

0.0007 0.0019 0.0021 0.0037b 0.0075 0.0099 0.0165 0.0171b 0.0096


0.0395 0.0912 0.1554 0.2020b 0.2578 0.3102 0.3604 0.3974b

0.9462 0.8876 0.8129 0.7550b 0.6903 0.6271 0.5508 0.4963b

T = 323.2 K 0.0606 0.1111 0.1582 0.2023b 0.2558 0.3120 0.3728 0.4104b

0.0034 0.0049 0.0055 0.0088b 0.0139 0.0225 0.0476 0.0710b

0.0613 0.1091 0.1558 0.1950b 0.2595 0.3131 0.3694 0.4100b

0.0031 0.0047 0.0069 0.0097b 0.0159 0.0239 0.0371 0.0516b

0.0016 0.0018 0.0034 0.0044b 0.0045 0.0050 0.0073 0.0136b 0.0063

wexp I1

wexp I3

Note: “w” represents the mass fraction; the subscripts of “I” and “II” indicate the organic phase and aqueous phase, while the subscripts of “1”, “2”, and “3” indicate 3-MPA, water, and TCM, respectively. The superscripts of “Exp” and “Cal” indicate the experimental data and calcualted data according to the NRTL equation, respectively. RMSDt is RMSD for each a goup of tie-line data; total average RMSD is the average RMSD of all b exp exp exp the tie-line data. Standard uncertainties, u, u(wexp I1 ) = u(wII1 ) = 0.007, u(wI3 ) = u(wII3 ) = 0.005, u(T) = 0.1 K, u(P) = 0.8 kPa. Predicated data by the obtained NRTL equation. a

water is set to be 0.2, while that between 3-MPA and water, 3MPA and TCM is set to be 0.3,17,19 while the binary interaction parameters were obtained by fitting the experimental data into eq 3 with the objective function in eq 4.20−25

preferred to correlate them to theoretical models. The NRTL and universal quasichemical (UNIQUAC) equations are the two most used thermodynamic models to simulate the liquid− liquid equilibrium. By a comparison with the UNIQUAC model, in this study, the experimental LLE data was correlated with the NRTL model (eq 3), using the Aspen Plus 7.2 software 16−18 due to the better agreement with the experimental data, especially at the high 3-MPA concentration. ln γi =

∑j τijGijxj ∑k Gik xk

+

∑ j

3

OF =

ij y jjτ − ∑k xkτjkGjk zzz jj ji z ∑k Gjk xk zz ∑k Gjk xk j k {

with Gij = exp( − αijτij)

II

n

∑ ∑ ∑ (wijkexp − wijkcal)2 (4)

i=1 j=I k=1

xiGji

cal where wexp ijk and wijk are the experimental and calculated mass fractions, i = 1 to 3 is the number of components, j = I to II is the phases, and k = 1 to n is the number of tie-lines. The quality of the correlation and prediction are judged by the root-mean-square-deviation (RMSD) of the experimental data from the calculated data from the NRTL equation using the correlated binary interaction parameters according to eq 5.

(3)

In eq 3, γ is the activity coefficients, x is its molar fractions, i = 1 to 3 is the number of components. τij is the binary interaction parameter between the ith and jth component (τii = 0, τij = τji), αij is the so-called non-randomness parameter ( αii = 0, αij = αji), which is commonly recommended as a constant between 0.2 and 0.3 in the literature according to the molecular polarity.8,10 In this study, by considering the type of the liquid mixtures, the non-randomness parameter between TCM and

É1/2 ÅÄÅ 3 exp cal 2 Ñ ÅÅ ∑i = 1 ∑IIj = I ∑nk = 1 (wijk − wijk ) ÑÑÑÑ ÅÅ ÑÑ RMSD = ÅÅ ÑÑ ÅÅ 6n ÑÑ ÅÅÇ ÑÖ

C

(5)



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Figure 1. Phase diagrams and tie-lines for the ternary system of 3-MPA + water + TCM system at (a) 303.2 K, (b) 313.2 K, (c) 323.2 K: −■−, experimental data for regression; −□−, experimental data for prediction; red −△−, calcualted data of NRTL; red −△−, prediction data of NRTL; ---, solubility curve predicted by NRTL; ◆, sum point.

3. RESULTS AND DISCUSSION 3.1. Experimental LLE Data of the Ternary System at Different Temperatures. Table 2 shows the experimental

with an accuracy of 0.01 kPa), and the corresponding phase diagrams and tie-lines are illustrated in Figure 1, and the comparison of the phase diagrams at different temperatures is shown in Figure 2. It can be seen that the partial miscibility region of the ternary system decreases with an increase in temperature as the solubility between TCM and water is enhanced. The experimental distribution coefficients of 3-MPA at different temperatures versus its concentration in the organic phase (Fig. 3a) show that the distribution coefficients decrease with an increase in temperature, which is a general observation in the liquid−liquid equilibrium of the ternary system.26−28 Table 3 lists the LLE data of the ternary mixture at 323.2 K with the addition of different amounts of NaCl (the mass fraction of NaCl in the original aqueous solution of 3-MPA is 0, 2, and 6 wt %, respectively), the corresponding phase diagram and tie-lines are plotted in Figure 4 and the phase diagrams with the addition of different amounts of NaCl is compared in Figure 5, demonstrating that the addition of NaCl can promote the extraction of 3-MPA from the aqueous phase by TCM. This effect is also verified by the results of the distribution coefficients (Fig. 3b), showing that the distribu-

Figure 2. Comparison of the phase diagrams at different temperatures: red −▲−, 303.2 K; −■−, 313.2 K; pink −◆−, 333.2 K.

LLE data of the ternary mixture without the addition of NaCl at (303.2, 313.2 and 323.2) K under atmospheric pressure (average value is 99.2 kPa, measured by a mercury barometer

Figure 3. Variation of the distribution coefficients of 3-MPA versus its concentration in the organic phase (a) at different temperatures and (b) with the addition of different concentration of NaClat 313 K. D



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Table 3. LLE Data of the Ternary Systems at 313.2 K and 99.2 kPa with the Addition of NaCla organic phase

aqueous phase

experimental data

calculated data

experimental data

calculated data

wcal I1

wcal I3

wexp II1

wexp II3

wcal II1

wcal II3

RMSDt


0.0459 0.1103 0.1795 0.2401b 0.2941 0.3486 0.4066 0.4599b

0.9499 0.8809 0.8037 0.7309b 0.6664 0.5952 0.5131 0.4375b

wNaCl = 2% 0.0525 0.0948 0.1337 0.1674b 0.2004 0.2306 0.2842 0.3257b

0.0028 0.0042 0.0044 0.0063b 0.0089 0.0122 0.0215 0.0364b

0.0538 0.0894 0.1276 0.1693b 0.2078 0.2537 0.3087 0.3500b

0.0028 0.0038 0.0052 0.0071b 0.0096 0.0134 0.0200 0.0245b

0.0008 0.0034 0.0048 0.0054b 0.0061 0.0155 0.0167 0.0180b 0.0109


0.0512 0.1201 0.2060 0.2641b 0.3333 0.3888 0.4332 0.4851b

0.9459 0.8736 0.7803 0.7144b 0.6322 0.5566 0.5040 0.4312b

wNaCl = 6% 0.0504 0.0813 0.1122 0.1301b 0.1545 0.1696 0.1835 0.2097b

0.0023 0.0026 0.0027 0.0033b 0.0040 0.0046 0.0047 0.005b

0.0493 0.0802 0.1074 0.1257b 0.1495 0.1714 0.1915 0.2193b

0.0021 0.0026 0.0031 0.0035b 0.0040 0.0045 0.0050 0.0058b

0.0019 0.0028 0.0038 0.0045b 0.0064 0.0068 0.0084 0.0247b 0.0101

wexp I1

wexp I3

Note: “w” represents the mass fraction; the subscripts of “I” and “II” indicate the organic phase and aqueous phase, while the subscripts of “1”, “2” and “3” indicate 3-MPA, water, and TCM, respectively. The superscripts of “Exp” and “Cal” indicate the experimental data and calcualted data according to the NRTL equation, respectively. RMSDt is RMSD of a goup of tie-line data; wNaCl is the mass fraction of NaCl in the original aqueous exp exp solution of 3-MPA; Total average RMSD is the average RMSD of all the tie-line data. Standard uncertainties, u, u(wexp I1 ) = u(wII1 ) = 0.007, u(wI3 ) = b u(wexp II3 ) = 0.005, u(T) = 0.1 K, u(P) = 0.8 kPa. Predicated data by the obtained NRTL equation.

a

Figure 4. Phase diagrams and tie-lines for the ternary system at 323.2 K with the addition of NaCl, (a) wNaCl = 2 wt %; (b) wNaCl = 6 wt %: −■−, experimental data for regression; −□−, experimental data for prediction; red −△−, calcualted data of NRTL; red −△−, prediction data of NRTL; ---, solubility curve predicted by NRTL; ◆, sum point.

tion coefficients can be significantly increased by adding NaCl in the aqueous phase due to the “salting out” effect.29−37 At the present study, we were not able to analyze the distribution of NaCl in the two phases due to the poor solubility of NaCl in the organic phase (the measured solubility of NaCl in TCM and 3-MPA, is 0.0004 g/L and 0.0015 g/L at 30 °C, respectively), which is, however, very important for deeply understanding the “salting out” effect and will be investigated in future studies. 3.2. Verification of the Experimental Data. The experimental data were verified by fitting with the Hand and the Othmer−Tobias plots. The Hand and Othmer−Tobias plots of the ternary systems at various temperatures were displayed in Figure 6; and those at 313.2 K with different concentrations of NaCl were displayed in Figure 7. As it can be seen from Figure 6 and Figure 7, a high degree of consistency

Figure 5. Comparison of the phase diagrams with the addition of different amount NaCl: pink −◆−, wNaCl = 0 wt %; −■−, wNaCl = 2 wt %; red −▲−, wNaCl = 6 wt %.

E



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Figure 6. (a) Hand and (b) Othmer−Tobias plots of the ternary system at various temperatures.

Figure 7. (a) Hand and (b) Othmer−Tobias plots of the ternary system with different concentrations of NaCl added in the original aqueous solutionat 313.2 K.

Table 4. Obtained Binary Interaction Parameters for the NRTL Model of the Ternary Systems at the Different Temperatures and Different NaCl Concentrations at 323.2 K and 99.2 kPa NRTL Parameters T/K

wNaCl

τ12

τ13

τ21

τ23

τ31

τ32

303.2 313.2 323.2 323.2 323.2

0 0 0 2% 6%

−1.2425 −0.3013 2.3446 −0.9399 −1.0063

−2.0637 −2.1275 −1.8344 −2.1652 −1.6346

3.0249 1.0558 −0.5312 2.2967 3.5008

5.963 6.408 7.0805 6.7337 6.8128

3.5644 3.7482 3.6617 4.2324 3.4240

3.4341 2.1574 1.5657 2.6670 2.9758

was obtained between the experimental data with the fitting lines, ascertaining the accuracy of the experimental data. 3.3. Correlation of the Experimental Data by the NRTL Model. In this section, the experimental data were correlated by using the NRTL model (eq 3) and setting the nonrandomness parameter between TCM and water, 3-MPA and water, and 3-MPA and TCM to be 0.2, 0.3, 0.3,17,19 respectively, in which, the binary interaction parameters were obtained (Table 4) by minimizing the objective function in eq 4. For validating the predictability of the obtained NRTL model, 6 of 8 experimental data were used for the correlation of the NRTL model and achieving the corresponding binary interaction parameters, and then the obtained model was used to predict the other two data and compare with the experimental data. The comparison of the calculated data with the experimental data (Table 2 and 3, Figures 1 and 4) showed that the calculated data by the NRTL model show good agreement with the experimental data. The maximum total RMSD for the five experimental scenarios is 0.0109 and the maximum RMSD for the 30 groups of data (6 for each experimental scenario) is 0.0173, demonstrating that the NRTL model can correlate well with the experimental data. Moreover, the NRTL model can

also predict the LLE data of the ternary system with good accuracy by using the obtained interaction energy parameters at specific temperatures (Table 4). For the involved 10 groups of data, the maximum RMSD is 0.0247, which ensures that the NRTL model is reliable to be used in the prediction of the LLE data for the investigated system at each experimental scenario. However, the developed NRTL model can not be employed to predict the LLE data at different temperatures since the the obtained interaction energy parameters are not correlated well with the temperature, which could be solved by measuring more experimental data at different temperatures and correlating the data using different thermodynamic models, for example, the extended UNIQUAC model.

4. CONCLUSIONS LLE for the ternary system of 3-mercaptopropionic acid + water + trichloromethane was investigated at different temperatures of (303.2, 313.2, and 323.2) K under atmospheric pressure, and the effect of the presence of NaCl in the system was also clarified, showing that the addition of NaCl can promote the extraction of 3-MPA from the aqueous phase by TCM due to the “salting out” effect. Furthermore, the F



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experimental data were correlated by using the NRTL model, and the results demonstrated that the NRTL model can accurately predict the LLE of the ternary system using the obtained interaction energy parameters at specific temperatures.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Lichun Dong: 0000-0002-9876-0133 Limei Zhang: 0000-0003-2955-5184 Funding

The authors gratefully acknowledge the financial support of this work by National Science Foundation of China [21776025, 21606026] and the fundamental research funds for the Central Universities of China [2019CDQYHG023, 2019CDXYHG0013]. Notes

The authors declare no competing financial interest.

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REFERENCES

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