Determination and Correlation of LiquidâLiquid Equilibria Data for

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

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Determination and Correlation of Liquid−Liquid Equilibria Data for Ternary System Isopropyl Acetate + Isopropanol + Water at Different Temperatures Lili Zhang, Zhaohui Liao, Chuanfu Zhu, Yingmin Yu,* and Qingsong Li

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State Key Laboratory of Heavy Oil Processing, College of Chemical Engineering, China University of Petroleum (East China), Qingdao, Shandong 266580, China ABSTRACT: The liquid−liquid equilibrium (LLE) data for the (isopropyl acetate + isopropanol + water) ternary system were determined experimentally using an equilibrium cell from 298.15 to 323.15 K at 101.3 kPa to obtain the fundamental data guiding the separation process of isopropyl acetate and isopropanol mixtures. The solvents’ extraction capacity was assessed by the solute distribution coefficient and selectivity. Othmer−Tobias and Bachman correlations for tie lines were used to assess the smoothed trend of the measured data. Thermodynamic models NRTL and UNIQUAC were used to correlate experimental data and obtain relevant binary interaction parameters. Both models provided good descriptions of the studied systems with rootmean-square deviations (RMSDs) of less than 0.2%. Moreover, a lower RMSD was found for the UNIQUAC model, demonstrating that it can correlate the experimental data successfully.

1. INTRODUCTION

The purpose of this work was to study the feasibility of extracing isopropanol from isopropyl acetate using water from 298.15 to 323.15 K at 101.3 kPa and obtain the liquid−liquid equilibrium experimental data for these ternary mixtures. The separation efficiency was studied by calculating the distribution coefficient and selectivity.10,11 Through fitting curves, the Othmer−Tobias and Bachman correlations were employed to assess the consistency and smoothed trend of the experimental tie-line data.12,13 Then the LLE data were regressed using thermodynamic models NRTL14 and UNIQUAC15 to receive the binary interaction parameters.

As a common chemical raw material and solvent, high-purity isopropanol has high economic and research value. There are many ways to prepare isopropanol, the most important of which is propylene hydration.1 Isopropyl acetate has very good miscibility with other solvents, the industrial preparation of which is relatively common with two main methods. One is directly synthesized from propylene and acetic acid.2 The other is obtained by using sulfuric acid as a catalyst and isopropanol and acetic acid by liquid-phase esterification.3,4 In the above industrial process, isopropanol and isopropyl acetate are important chemicals that are easily mixed together. If the mixture is not separated, then the added value of the product is low, which is a waste of resources. Isopropanol and isopropyl acetate, which have very important application values in the fields of chemistry,5 chemical engineering,6 and medicine,7 often require separation and purification in the processing industry. Because of the formation of the minimum azeotrope, the binary mixture cannot be separated by a simple distillation. Extraction is widely used in the separation of azeotropic systems.8,9 The main purpose of this article is to optimize and simulate the separation process of isopropanol and isopropyl acetate by extraction. The liquid− liquid equilibria for ternary mixtures of isopropanol, isopropyl acetate, and the extractant (water) were studied. We used the obtained binary interaction parameters to simulate the extraction process in order to reduce the costs and improve the purity of the product. The simulation of extraction provides theoretical guidance for separating the isopropanol and isopropyl acetate in the processing industry. © XXXX American Chemical Society

2. EXPERIMENTAL SECTION 2.1. Chemical Reagents. The sources and purities of the chemicals used in the experiments are presented in Table 1.16−18 All chemicals have purities >0.985 in mass fraction. Their purities were determined through gas chromatography (GC) because impurities can affect the experimental measurements. No significant impurity peaks have been detected, hence all of the chemicals were used directly without any further purification. Deionized water obtained in our laboratory was used throughout all of the experiments, and the electrical conductivity was 8.35 μS·cm−1. The physical properties of all of the measurements and their comparisons with the literature values are listed in Table 1. 2.2. Apparatus and Procedure. The refractive indexes were measured using the Abbe refractometer with an accuracy in Received: September 20, 2018 Accepted: January 31, 2019

A

DOI: 10.1021/acs.jced.8b00844 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Characterization of Chemical Reagents Measured at 298.15 and 101.3 KPaa ρ(g·cm−3) component b

water isopropyl acetate isopropanol

supplier self-made Sinopharm Sinopharm

reported GC purity (mass %)

GC purity (mass %) 99.92 99.50 98.80

≥99.5 ≥98.5

exp 0.9970 0.8676 0.7814

nD lit 16

0.9970 0.8662117 0.7812618

exp

lit

1.3325 1.3701 1.3750

1.332516 1.374917 1.375218

Standard uncertainties u were u(T) = 0.01 K, u(P) = 0.7 kPa, u(ρ) = 0.008, and u(nD) = 0.006. bThe electrical conductivity of water is 8.35 μS· cm−1. a

the experimental measurements of ±5.0 × 10−4. The densities were measured with an Anton Paar DMA 4500 digital density meter with an accuracy in the experimental measurements of ±1.0 × 10−4 g·cm−3. In the process of measuring the density, the temperature uncertainties were ±0.01 K. The slight difference between the experimental values and the literature values may be due to the presence of water or other nonvolatile impurities in the sample. The LLE data was measured from 298.15 to 323.15 K and the standard uncertainty was ±0.1 K,19 and then the mixtures were used to fill the 50 mL glass-sealed equilibrium cell before being agitated vigorously for more than 2 h with the magnetic stirrer.20 The mixtures were allowed to settle for more than 6 h to ensure sufficient phase separation and equilibration and were separated into organic and aqueous phases (Some preliminary experiments21−23 have been done, and these indicated that this period was sufficient to allow complete phase separation and keep the system in thermodynamic equilibrium.) 1,4-Dioxane was utilized as an internal standard to obtain the calibration factor, and the internal standard method was applied to determine the composition of the sample. The samples were analyzed with an Agilent GC6820 gas chromatograph with a Porapak N column and a thermal conductivity detector (TCD); meanwhile, each phase was sampled at approximately 0.6 μL. The peak area ratio was converted to the mass ratio using a standard analysis method. A standard sample of known composition was used to adjust the gas chromatograph detector to within the desired composition range. All samples were injected into a gas chromatograph. (The detector and injector temperatures were 533.15 K, and the flow rate of the high-purity carrier gas (hydrogen) was 50 cm3· min−1.) The column that was used was 3 m long and 3 mm in diameter. The column temperature was first programmed to be 383.15 K for 2.0 min before being increased to a final temperature of 533.15 K at a rate of 25 K·min−1 and maintained for 1 min. Samples were collected from lower and upper phases and analyzed more than three times to guarantee the accuracy of the data, and the calculated standard deviation was less than 0.1%. Then the average value of three sets of the best data was finally determined as the sample composition. A series of LLE data were achieved by varying the temperature and the feed composition. In addition, the standard uncertainty in the composition of each phase sample was received according to the Guide to the Expression of Uncertainty in Measurement standard.

extraction according to Treybal,24 which consist of two miscible binary components (isopropyl acetate + isopropanol and isopropanol + water)25−27 and one partially miscible binary component (isopropyl acetate + water).28 The plait point on the type I ternary LLE diagram indicates the point where the two liquid phases become one phase having the same composition. The achieved mutual binary solubilities between isopropyl acetate and water at different temperatures and their comparisons with the literature data29,30 are displayed in Table 3 and compared graphically in Figure 7. The data in Table 3 shows that the binary solubility obtained in the experiment is consistent with the literature data, and different measurement methods may cause some deviations. Moreover, an analysis of the experimental results revealed that the miscibilities of water in isopropyl acetate increase with increasing temperature, but it is worth mentioning that the various temperatures did not have an obvious effect on the equilibrium. From these figures, it can be inferred that the points of the feed composition were consistent with the connecting line and had a high degree of precision, which was in accordance with the rules of leverage. The results show that the experimental operation satisfied the lever rule of mass balance well, which proved the accuracy and the reliability of the experimental values. The distribution coefficient (D) and selectivity (S) were used to evaluate the efficiency of water in separating isopropanol from isopropyl acetate, and they were calculated as follows31 D=

S=

w2β w2α

(1)

w2β /w1β w2α /w1α

(2)

where w2α and w2β are the concentrations of isopropyl acetate expressed in mass fraction in the organic and aqueous phases, respectively. w1α and w1β denote the concentrations of isopropanol expressed in mass fraction in the above two phases, respectively. D and S data at different temperatures are listed in Table 2. From these tables and figures, it can be found that the distribution coefficients are prone to decrease as the concentration of isopropanol increases, when the system is stable. The selectivity describes the effectiveness of the extractant. As presented in Table 2, the selectivity of the solvent is >1, revealing the feasibility of isopropanol extraction using water. Quantitatively, Othmer−Tobias and Bachman equations were emplyed to assess the consistency and the reliability of the experimental values. The correlation equations are as follows

3. RESULTS AND DISCUSSION 3.1. Experimental Data. The expreimental data for the ternary mixture (isopropyl acetate + isopropanol + water) was determined at different temperatures and is presented in Table 2. In addition, the concentrations of all substances were expressed in mass fraction. Ternary phase diagrams are shown in Figures 1−6. The phase diagrams for the ternary liquid− liquid equilibrium systems in this study were classified as a type I

ij 1 − w3β yz zz = a + b ln ijjj 1 − w1α yzzz lnjjjj z 1 1 jj w zz j w3β zz 1α k { k {

B

(3)



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Table 2. LLE Data for the Isopropyl Acetate (1) + Isopropanol (2) + Water (3) System at Different Temperatures (298.15− 323.15 K) under 101.3 kPaa organic phase T/K

w1b

298.15

0.9832 0.9395 0.9047 0.8735 0.8151 0.7848 0.7511 0.7180 0.6842 0.9824 0.9464 0.9175 0.8832 0.8428 0.8067 0.7681 0.7294 0.6573 0.9791 0.9518 0.9135 0.8779 0.7721 0.7374 0.7043 0.6674 0.6378 0.9772 0.9407 0.9039 0.8617 0.8241 0.7805 0.7398 0.6985 0.6578 0.9768 0.9438 0.9099 0.8280 0.7951 0.7534 0.7180 0.6818 0.6472 0.9746 0.9331 0.8966 0.8624 0.8243 0.7904 0.7401 0.7071 0.6629

303.15

308.15

313.15

318.15

325.15

w2b 0.2028 0.0438 0.0690 0.1220 0.1479 0.1732 0.1974 0.2195 0.0245 0.0503 0.0767 0.1043 0.1322 0.1585 0.1850 0.2317 0.0229 0.0488 0.0752 0.1537 0.1798 0.2048 0.2268 0.2471 0.0269 0.0552 0.0842 0.1136 0.1430 0.1707 0.1972 0.2216 0.0268 0.0548 0.1124 0.1415 0.1686 0.1948 0.2189 0.2409 0.0302 0.0586 0.0870 0.1181 0.1412 0.1747 0.2007 0.2265

aqueous phase w3b

w1

0.0168 0.0397 0.0515 0.0576 0.0629 0.0673 0.0757 0.0846 0.0963 0.0176 0.0291 0.0322 0.0402 0.0529 0.0611 0.0734 0.0856 0.1110 0.0209 0.0253 0.0378 0.0469 0.0742 0.0828 0.0909 0.1058 0.1151 0.0228 0.0324 0.0408 0.0541 0.0623 0.0765 0.0895 0.1043 0.1205 0.0232 0.0294 0.0353 0.0495 0.0634 0.0779 0.0873 0.0993 0.1119 0.0254 0.0367 0.0448 0.0506 0.0576 0.0684 0.0852 0.0922 0.1106

0.0271 0.0328 0.0337 0.0341 0.0371 0.0392 0.0384 0.0380 0.0394 0.0258 0.0480 0.0462 0.0439 0.0492 0.0462 0.0505 0.0470 0.0488 0.0233 0.0324 0.0412 0.0415 0.0413 0.0426 0.0384 0.0436 0.0480 0.0221 0.0470 0.0502 0.0502 0.0540 0.0554 0.0519 0.0572 0.0601 0.0218 0.0432 0.0431 0.0496 0.0523 0.0504 0.0491 0.0483 0.0535 0.0211 0.0369 0.0420 0.0454 0.0491 0.0499 0.0533 0.0533 0.0593

w2 0.0270 0.0498 0.0722 0.1022 0.1150 0.1265 0.1364 0.1473 0.0264 0.0495 0.0691 0.0852 0.0996 0.1108 0.1222 0.1401 0.0240 0.0437 0.0614 0.1013 0.1126 0.1212 0.1312 0.1391 0.0227 0.0432 0.0607 0.0761 0.0891 0.1007 0.1114 0.1211 0.0215 0.0409 0.0724 0.0842 0.0955 0.1057 0.1142 0.1233 0.0224 0.0429 0.0618 0.0728 0.0864 0.1137 0.1241 0.1323

w3 0.9729 0.9402 0.9165 0.8937 0.8607 0.8466 0.8355 0.8242 0.8134 0.9742 0.9255 0.9043 0.8870 0.8656 0.8542 0.8387 0.8309 0.8112 0.9767 0.9436 0.9151 0.8971 0.8573 0.8448 0.8404 0.8252 0.8129 0.9779 0.9303 0.9067 0.8891 0.8699 0.8555 0.8474 0.8314 0.8188 0.9782 0.9353 0.9161 0.8780 0.8635 0.8541 0.8452 0.8375 0.8232 0.9789 0.9407 0.9150 0.8928 0.8781 0.8647 0.8329 0.8226 0.8085

D

S

1.30 1.14 1.05 0.84 0.78 0.73 0.69 0.67

37.11 30.53 26.85 18.38 15.88 14.42 12.61 11.70

1.08 0.98 0.90 0.82 0.75 0.70 0.66 0.60

21.23 19.56 18.13 13.98 13.16 10.63 10.26 8.15

1.04 0.90 0.82 0.66 0.63 0.59 0.58 0.56

30.66 19.85 17.26 12.31 10.83 10.85 8.85 7.48

0.84 0.78 0.72 0.67 0.62 0.59 0.56 0.55

16.90 14.08 12.37 10.22 8.78 8.41 6.90 5.98

0.80 0.75 0.64 0.59 0.57 0.54 0.52 0.51

17.55 15.75 10.76 9.04 8.47 7.95 7.36 6.19

0.74 0.73 0.71 0.62 0.60 0.65 0.62 0.58

18.73 15.62 13.48 10.35 9.58 9.04 8.20 6.53

a

Standard uncertainties u are u(T) = 0.01 K, u(P) = 0.7 kPa, and u(w) = 0.003. bw1: mass fraction of isopropyl acetate. w2: mass fraction of isopropanol. w3: mass fraction of water. C



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Figure 1. Ternary phase diagram for the isopropyl acetate (1) + isopropanol (2) + water (3) system at 298.15 K: (☆) feed composition, (□) experimental data, (○) NRTL model, and (△) UNIQUAC model.



Figure 5. Ternary phase diagram for the isopropyl acetate (1) + isopropanol (2) + water (3) system at 318.15 K: (☆) feed composition, (□) experimental data;, (○) NRTL model, and (△) UNIQUAC model.


ij w3β yz w3β = a 2 + b2jjj zz j w1α zz k {


concentration of isopropyl acetate in the isopropyl acetate-rich phase is expressed in mass fraction. a1, b1, a2, and b2 are constants. The parameters of the Othmer−Tobias and Bachman equations are shown in Table 3. Simultaneously, the plots of

(4)

where w1α and w3β are related, the concentration of water in the water-rich phase is expressed in mass fraction, and the D



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Table 3. Solubility Data in Mass Fraction for the Isopropyl Acetate−Water System Measured from 298.15 to 323.15 K under 101.3 kPa and Comparison with Literature Dataa isopropyl acetate in water T/K

wexp

298.15

0.0271

303.15

0.0258

308.15

0.0233

313.15 318.15

0.0221 0.0218

323.15

0.0211

wlit 0.026029,b 0.022030 0.024429 0.023229,b 0.022925 0.021929 0.020929,b 0.020729 0.020025

water in isopropyl acetate wexp 0.0168 0.0176 0.0209 0.0228 0.0232 0.0254

wlit 0.016229,b 0.022030 0.017529 0.019829,b 0.020025 0.0220129 0.021529,b 0.022329 0.025025

a

Standard uncertainties u are u(T) = 0.1 K, u(p) = 1 kPa, and u(w) = 0.003. bThe binaries were taken from the interpolation of the data in ref 29.

Figure 9. Bachman equation plots of the isopropyl acetate + isopropanol + water system from 303.15 to 323.15 K.

3.2. Uncertainty Calculation. There are two parameters A and B19 that are used to calculate the uncertainty. The uncertainty in each quantity q was checked with type A in this work. The corresponding calculation formulas are described as follows n

s 2(qk ) =

∑ (qj − q ̅ )2 /(n − 1)

(5)

j=1

s 2(q ̅ ) = s 2(qk )/n

(6)

u(wi) = s(Wi̅ )

(7)

where the standard deviation (s(qk)) is obtained to characterize the variability of the observed values qk or their dispersion about their mean q̅, more specifically. Consequently, for input amount Xi, the standard uncertainty in type A, u(wi), of its estimate wi = W̅ i is u(wi) = s(W̅ i). 3.3. Experimental Correlation. In this article, the LLE data were simulated using thermodynamic models NRTL and UNIQUAC with Aspen Plus software to calculate the activity coefficients. Among them, the NRTL model can well represent many LLE systems by correctly selecting nonrandom parameters. Moreover, nonrandom parameter αij of the NRTL model has a value of 0.3, as shown in Table 4. For the UNIQUAC model, structural parameters r and q of the pure components are obtained from the Aspen Plus physical properties databanks and listed in Table 5. The root-mean-square deviation (RMSD) used in this study was calculated on the basis of the following equation32−35

Figure 7. Comparison of our experimental data with those reported in the literature for the water−isopropyl acetate liquid−liquid two-phase system.

Othmer−Tobias and Bachman correlations are shown in Figures 8 and 9 with correlation factor R2 varying from 0.9921 to 0.9994, which indicates the successful reliability and consistency of our LLE data.

Table 4. Parameters of Othmer−Tobias and Bachman Equations for the Isopropyl Acetate + Isopropanol + Water Systema Othmer−Tobias

Figure 8. Othmer−Tobias equation plots of the isopropyl acetate + isopropanol + water system from 303.15 to 323.15 K.

Bachman 2

T/K

a1

b1

R

298.15 303.15 308.15 313.15 318.15 323.15

1.4720 2.0680 1.8569 1.9704 1.9603 1.4743

1.2656 2.2612 1.1425 2.2803 2.3680 1.3742

0.9941 0.9921 0.9931 0.9948 0.9931 0.9932

a2

b2

R2

0.7899 0.7688 0.7933 0.7967 0.8050 0.7828

0.0066 0.0086 0.0058 0.0052 0.0047 0.0063

0.9986 0.9994 0.9987 0.9985 0.9988 0.9983

a 2

R is the correlation coefficient.

E



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Table 5. UNIQUAC Structural Parameters (r and q)a component

r

q

isopropyl acetate isopropanol water

4.1523 2.9137 0.9200

3.6250 2.5276 1.4000

Table 7. Plait Point for the Isopropyl Acetate (1) + Isopropanol (2) + Water (3) System from 298.15 to 323.15 K Estimated Using NRTL and UNIQUAC Model Parameters Plait point

a

Taken from Aspen Plus physical properties databanks. 1/2 l n 2 3 (w exp − w cal)2 | o o o o ijk ijk o o RMSD = m } ∑∑∑ o o o o 6n ok=1 j=1 i=1 o n ~

T/K

model

W1

W2

298.15

NRTL UNIQUAC NRTL UNIQUAC NRTL UNIQUAC NRTL UNIQUAC NRTL UNIQUAC NRTL UNIQUAC

0.1452 0.1303 0.1371 0.1355 0.1143 0.1191 0.1142 0.1099 0.0865 0.0953 0.1518 0.1533

0.4053 0.3993 0.3985 0.3931 0.3634 0.3760 0.3639 0.3705 0.3872 0.3875 0.4115 0.4083

303.15

(8)

308.15

where wexp and wcal represent the experimental mass fractions and values calculated by models, respectively. Subscripts i and j refer to the component and the phase, respectively. Subscript k is the quantity of tie lines, and n is the total quantity of tie lines. The binary interaction parameter pairs (gij − gjj, gji − gii, uij − ujj, and uij − ujj) were obtained by minimizing the flowing objective function (OF):

313.15

n

OF =

2

318.15 323.15

4. CONCLUSIONS The experimental LLE data for ternary system (isopropyl acetate + isopropanol + water) were determined successfully from 303.15 to 323.15 K at 101.3 kPa. The LLE data were checked by the Othmer−Tobias and Bachman equations, and the linearity of the plots for different systems indicates the coherence and accuracy of our data. The distribution coefficient and selectivity are also reported. Thermodynamic models NRTL and UNIQUAC were applied to correlate and predict the LLE data, both of which accurately describe the phase behavior of the system in our study and yield relevant binary interaction parameters. This study supplemented the lack of liquid−liquid phase equilibrium data between water−isopropyl acetate and isopropanol−isopropyl acetate−water, which provided a large operating range extraction process. Moreover, our study indicated the possibility of separating isopropyl acetate and isopropanol with water. However, the low distribution

3

∑∑∑

exp (wijk

−

cal 2 wijk )

(9)

k=1 j=1 i=1

The experimental data calculated through thermodynamic models UNIQUAC and NRTL for all systems studied are wellplotted in Figures 1−6, confirming that both models are suitable for simulating the extraction process of isopropanol. The binary interaction parameter pairs for NRTL and UNIQUAC models along with RMSD values for the studied systems from 303.15 to 323.15 K are shown in Table 6, and the RMSD values range from 0.0005 to 0.0013. This indicates that both models are qualified to predict the LLE data for the studied systems. Besides, Plait point estimations for the type I isopropyl acetate + isopropanol + water system used thermodynamic models NRTL and UNIQUAC, and the results are given in Table 7.

Table 6. Binary Energy Parameters of NRTL and UNIQUAC Models for the Isopropyl Acetate (1) + Isopropanol (2) + Water (3) System NRTL parameters T/K

i−j

gij − gjj

298.15

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

3026.95 2644.75 −693.21 2290.73 3744.16 −1404.00 1907.78 4093.37 −1972.18 2099.23 3639.75 −2119.76 1512.27 4061.29 −1848.09 1930.06 3642.37 −1684.79

303.15

308.15

313.15

318.15

323.15

a

gji − gii

a

3834.89 11 152.71 9034.54 2641.01 10 409.27 9100.46 1683.27 11 086.22 9029.78 2998.74 10 537.80 10 493.98 1478.08 10 869.41 9023.79 3811.47 11 039.26 9710.79

UNIQUAC parameters α 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3

RMSD/% 0.07

0.13

0.09

0.11

0.12

0.07

uij − ujja

uji − uiia

1889.91 2351.28 −362.69 1986.80 3618.39 −249.54 2595.03 3554.28 −727.07 2141.67 3695.51 −869.90 2016.35 3884.01 −639.46 2105.80 3425.87 −718.61

−249.23 746.87 1425.81 −325.26 709.88 1624.80 −713.52 887.70 1865.95 −745.44 656.58 2137.76 −663.53 693.99 1936.56 −781.32 853.00 1540.73

RMSD/% 0.08

0.05

0.13

0.13

0.05

0.03

a

Parameters are given in J/mol. F



Article

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coefficient may lead to material waste and application limitations in large-scale industrial production.

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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.

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REFERENCES

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