Liquid–Liquid Equilibrium Data and Correlation for the Quaternary

Dec 15, 2017 - College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China ... were used to evaluate the feas...
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Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Liquid−Liquid Equilibrium Data and Correlation for the Quaternary Systems Water + Polyphenol (Hydroquinone, Catechol, and Resorcinol) + Methyl Isobutyl Ketone + Methylbenzene Sheng Yang,† Donghui Ma,‡ and Peizhe Cui*,§ †

School of Energy Science and Engineering, Central South University, Changsha 410083, China Sinopec Shanghai Research Institute of Petrochemical Technology, Shanghai 201208, China § College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China ‡

ABSTRACT: The wastewater containing polyphenol (hydroquinone, catechol, and resorcinol) is often found in many industrial processes. Liquid−liquid extraction is a commonly used method to separate this style wastewater. The liquid−liquid equilibrium for the quaternary systems of water + polyphenol (hydroquinone, catechol, and resorcinol) + methyl isobutyl ketone (MIBK) + toluene were measured at 298.15 K and 0.1 MPa. The potential for the mixture of MIBK + toluene to extract the polyphenol from its aqueous solution was examined, and the distribution coefficient and selectivity were used to evaluate the extractive ability for the mixed solvent of toluene and MIBK. The results show that mixed solvent has better extraction ability compared with single extractant (MIBK). The nonrandom two-liquid and universal quasi-chemical models were used to correlate experimental data, and the binary interaction parameters were obtained. The values of room-mean-square-deviation (RMSD) were used to evaluate the feasibility of the two models for the systems and all the values of RMSD were less than 2%, which shows that the two models can correlate the experimental data properly. Kim et al.17 Wang et al.18 measured LLE data for the ternary system water + benzyl alcohol + methylbenzene at different temperatures. To enhance the extraction efficiency of MIBK, toluene was mixed with MIBK as extractants to separate polyphenol from water. Many researchers have studied the extractive separation of water and phenol.19,20 For example, Martin et al.19 researched the extraction of phenol from water using hydrocarbons (toluene and ethylbenzene) and hydrocarbons (heptane and octane). Hwang et al.20 reported the systems of dimethyl carbonate + phenol + water and diphenyl carbonate + phenol+ water. But only a few of study reported the extraction of polyphenol from water. Yang et al.10 measured the LLE data for the systems of MIBK + water + hydroquinone, but the extraction ability for the mixed solvent of MIBK + toluene has not been researched in the literature. There are many studies on the separation process using mixed solvents.21−26 To obtain the essential parameters for extraction process, the phase behaviors of quaternary systems of water + polyphenol (hydroquinone, catechol, and resorcinol) + MIBK + toluene at 298.15 K and 0.1 MPa were studied. The mixed solvent of MIBK and toluene was used to separate polyphenol from its aqueous solution. The experimental data were correlated by NRTL27 and UNIQUAC28 models, the binary interaction parameters for the two models which are necessary for the

1. INTRODUCTION The wastewater containing polyphenol is produced in several industrial processes, such as petroleum refining, coking operation, coal gasification, and wood processing.1 In many industrial processes, the wastewater is handled by a biochemical method; however, the polyphenol (hydroquinone, catechol, and resorcinol) are toxic for bacteria. So, before the biochemical treatment of this wastewater, the polyphenol should be removed. Liquid−liquid extraction is an energy-efficient and efficient separation method,2,3 but the key issue is to find efficient extractants. Benzene, dissoproply ether, heavy benzene, isobutyl alcohol, ethyl acetate, isopropyl and isobutyl ketone (MIBK) were used as extractants to extract polyphenol from its aqueous solution.4−9 Some of them have been successfully used in industry, and MIBK is an efficient extraction solvent to separate organic components from water;10−13 however, the separation of polyphenol using MIBK has a low distribution coefficient. Toluene is a widely used solvent in the industry and an important raw material for organic chemicals,14−18 many researches studied the phase behavior for the systems containing water and toluene, Gomis et al.14 reported the vapor−liquid equilibrium (VLE) and vapor−liquid−liquid equilibrium (VLLE) for the systems of water + ethanol + toluene. Gramajo et al.15 studied the liquid−liquid equilibria (LLE) for the ternary systems containing water and toluene, Grenner et al.16 researched the phase behavior for systems of water + aniline + toluene; liquid−liquid equilibrium for the quaternary system of toluene + water + propionic acid + ethyl acetate was reported by © XXXX American Chemical Society

Received: June 30, 2017 Accepted: November 29, 2017

A

DOI: 10.1021/acs.jced.7b00598 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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extraction simulation design were obtained. The values of roommean-square-deviation (RMSD) were calculated to estimate whether the two models are suitable for systems studied in this paper.

Table 2. UNIQUAC Structural Parameters of Pure Componentsa

2. EXPERIMENT 2.1. Chemicals. The information on materials used in this work was listed in Table 1. The purities of chemical components Table 1. List of Chemicals component MIBK hydroquinone catechol resorcinol toluene water a

supplier Guangzhou Chemical reagent Factory Tianjin Kemiou Chemical reagent Co., Ltd. Tianjin Kemiou Chemical reagent Co., Ltd. Tianjin Kemiou Chemical reagent Co., Ltd. Shanghai Runjie Chemical reagent Co., Ltd. A.S.Watson Group.,Ltd.

a

the CAS registry number

mass fraction

108−10−1

0.99a

123−31−9

0.995a

120−80−9

0.995a

108−46−3

0.995a

108−88−3

0.999

a

7732−18−5

0.999a

component

r

q

water hydroquinone catechol resorcinol MIBK toluene

0.920 3.916 3.985 3.965 4.596 3.923

1.400 3.008 3.015 3.011 3.952 2.968

From refs 21 and 22.

process: from 383.15 to 500.15 K at a rate of 10 K/min, and maintained at 500.15 K for 2 min. The internal standard used in this work is ethanol. Nitrogen (>99.99% purity) was used as carrier gas with a flow rate of 30 mL/min. All the samples were measured at least three times.

3. RESULTS AND DISCUSSION 3.1. Experiment Data. The experimental data for quaternary systems of water + polyphenol (hydroquinone, catechol, and resorcinol) + MIBK + toluene at 298.15 K and 0.1 MPa are shown in Table 3, where wi is the mass fraction for every composition. To analyze the phase behaviors using mixed the solvent of MIBK + toluene properly, the experimental data were displayed in triangular diagrams as shown in Figures 1−3. The volume fraction of toluene in mixed solvent was fixed as 5%. The selectivity (S) estimates the efficiency for the mixed solvent and the distribution coefficient (D) measures the solvent capacity for the mixed solvent, the values of S and D were calculated by following equations:

Analysis by supplier.

were checked by gas chromatography (GC) by suppliers. The water used in this paper was deionized and distilled water. All materials were used without further purification. 2.2. Apparatus and Procedure. The equilibrium cell with a volume of 100 mL was used to obtain the LLE data. The prepared quaternary mixtures with different mass compositions were put into the equilibrium cell. The mass of samples was measured using an analytical balance (FA-2104N) purchased from Precision Science Instrument Co., Ltd., Shanghai, China. The volume fraction of toluene in mixed solvent was 5%. To maintain the temperature in the experiment, the equilibrium cell contains a heating jacket and is connected with a bath. The temperature was controlled with a thermostatic bath (Sc-15) purchased from Tianheng Instrument Factory of Zhejiang Ningbo in China. In the experimental procedure, the pH was adjusted to be 7 by adding hydrochloric acid into the water phase. The extraction process does not change the pH of the system, so there is no buffer solution added to the system. The value of pH was measured by pH-meter (pHS-25) purchased from Precision Science Instrument Co., Ltd., Shanghai, China. Before measurement the LLE data for the quaternary system, the time required until liquid−liquid equilibrium was studied. The experiment time until the content of polyphenol in the raffinate phase is constant was determined. The samples were stirred vigorously by magnetic stirrer for at least 2 h, and then settled for at least 10 h to ensure the two phases were completely separated. The experimental time was determined by measuring the concentration of polyphenol with mass fraction in raffinate. The composition of compounds were analyzed by gas chromatograph (GC-6820) equipped with a flame ionization detector (FID) and capillary column (DB-5MS, 30 m × 0.32 mm × 0.25 μm). The internal standard method were used to determine the mass fraction of every constituent in organic and aqueous phases, and the concentration of water was obtained by mass balance. The test conditions for the gas chromatograph were shown as follows: the temperature of injector was 533.15 K and the temperature of detector was 523.15 K, the column oven was maintained at 383.15 K for 2 min and then followed a heating

D=

w2o w2w

S=

(w2 /w3)o (w2 /w3)w

wo2

(1)

(2)

ww2

where is mass fraction of polyphenol in organic phase, is mass fraction of polyphenol in aqueous phase. wo3 and ww3 are mass fraction of water in the organic and aqueous phases, respectively. As can be seen from Table 3, the system for the MIBK + catechol + water + toluene has the maximum values of D and S, this can illustrate that the mixed solvent has the best extraction result on the MIBK + catechol + water + toluene system. Figure 4 shows the values of S for systems, it can be seen that the mixed solvent has higher selectivity for catechol than the other systems. The consistency of experimentally determined LLE data for different quaternary systems can be examined by the Hand29 and Bachman30 correlation: ⎛ w ⎞w ⎛ w ⎞o ln⎜ 2 ⎟ = a1 + b1 ln⎜ 2 ⎟ ⎝ w1 ⎠ ⎝ w3 ⎠

(3)

⎛ wo ⎞ w1o = a 2 + b2⎜ 1w ⎟ ⎝ w3 ⎠

(4)

where a and b are constants; the subscript 1 and 3 represents MIBK and water, respectively. The superscripts o and w represent organic phase and aqueous phase, respectively. Hand and Bachman plots are shown in Figure 5 and Figure 6, B

DOI: 10.1021/acs.jced.7b00598 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 3. LLE Data, Solute Distribution, D and Selectivity, S, for Quaternary Systems of MIBK (1) + Polyphenol (Hydroquinone, Catechol, and Resorcinol) (2) + Water (3) + Toluene (4) at 298.15 K and 0.1 MPa organic phase w1

a

w2

0.91941 0.90949 0.89123 0.85601 0.82757 0.77472 0.71916 0.66211 0.64108

0.0000 0.00742 0.01529 0.03403 0.05612 0.10321 0.15364 0.20831 0.22491

0.91886 0.90926 0.89161 0.85431 0.82371 0.77927 0.71292 0.65439 0.62908

0.0000 0.00714 0.01468 0.03552 0.05986 0.09845 0.15969 0.21566 0.23684

0.91967 0.90920 0.89278 0.85466 0.82584 0.78950 0.71807 0.65882 0.63282

0.0000 0.00725 0.01359 0.03524 0.05792 0.08839 0.15484 0.21148 0.23324

aqueous phase w3

w1

w2

MIBK (1) + Hydroquinone (2) + Water (3) + Toluene (4) 0.02361 0.01872 0.0000 0.02551 0.01763 0.00041 0.02632 0.01676 0.00084 0.02811 0.01543 0.00188 0.03106 0.01381 0.00305 0.03252 0.01063 0.00564 0.03479 0.00719 0.00835 0.03502 0.00319 0.01126 0.03773 0.00170 0.01229 MIBK (1) + Resorcinol (2) + Water (3) + Toluene (4) 0.02358 0.01877 0.0000 0.02549 0.01789 0.00035 0.02614 0.01712 0.00072 0.02803 0.01592 0.00175 0.03086 0.01441 0.00292 0.03239 0.01156 0.00485 0.03461 0.00754 0.00779 0.03498 0.00342 0.01052 0.03745 0.00222 0.01161 MIBK (1) + Catechol (2) + Water (3) + Toluene (4) 0.02360 0.01875 0.0000 0.02552 0.01786 0.00037 0.02631 0.01706 0.00069 0.02809 0.01582 0.00178 0.03101 0.01435 0.00297 0.03246 0.01189 0.00451 0.03471 0.00747 0.00786 0.03499 0.00317 0.01079 0.03765 0.00193 0.01190

w3

D

S

0.98071 0.98132 0.98162 0.98181 0.98215 0.98263 0.98322 0.98411 0.98445

18.10 18.20 18.10 18.40 18.30 18.40 18.50 18.30

696.18 678.87 632.22 581.83 552.95 520.01 519.88 477.49

0.98069 0.98109 0.98132 0.98141 0.98162 0.98246 0.98338 0.98456 0.98458

19.59 19.70 19.80 19.50 19.60 19.70 19.60 19.60

753.29 734.66 691.70 617.32 593.16 558.09 551.47 512.54

0.98067 0.98108 0.98138 0.98142 0.98161 0.98242 0.98333 0.98451 0.98455

20.40 20.39 20.30 20.50 20.30 20.50 20.50 20.40

785.18 765.42 710.66 652.08 615.71 582.45 577.00 536.32

Standard uncertainties u are u(T) = 0.1 K, u(P) = 0.01 MPa, u(w) = 0.0004.

Figure 2. LLE phase diagram for the systems of MIBK (1) + resorcinol (2) + water (3) + toluene (4) at T = 298.15 K and P = 0.1 MPa.

Figure 1. LLE phase diagram for the systems of MIBK (1) + hydroquinone (2) + water (3) + toluene (4) at T = 298.15 K and P = 0.1 MPa.

component systems and the required interaction parameters are given in eq 5.

respectively. Parameters of the Hand and Bachman correlation for each quaternary system were presented in Table 5. The sample correlation factor (R2) indicates the consistency of the data. 3.2. LLE Correlation. There are many papers correlated the LLE data by the NRTL and UNIQUAC models.31−33 In this paper, the two models were used to regress experimental data. The NRTL expression for the activity coefficient in multi-

ln γi =

τij = C

∑j τjiGjixj ∑k Gkixk

Δg ij RT

+

∑ j

⎛ ∑ τG x ⎞ ⎜⎜τij − v vj vj v ⎟⎟ ∑k Gkjxk ⎠ ∑k Gkjxk ⎝ Gijxj

Gij = exp( −αijτij)

(5) DOI: 10.1021/acs.jced.7b00598 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Figure 3. LLE phase diagram for the systems of MIBK (1) + catechol (2) + water (3) + toluene (4) at T = 298.15 K and P = 0.1 MPa.

Figure 6. Bachman plots of the system MIBK (1) + polyphenol (hydroquinone, catechol, and resorcinol) (2) + water (3) + toluene (4).

Table 4. NRTL and UNIQUAC Binary Interaction Parameters for at T = 298.15 K and p = 0.1 MPa i−j

1−2 1−3 1−4 2−3 2−4 3−4 1−2 1−3 1−4 2−3 2−4 3−4

Figure 4. Selectivity (S) for quaternary systems of for the systems of MIBK (1) + polyphenol (hydroquinone, catechol, and resorcinol) (2) + water (3) + toluene (4). wI2 is the mass fraction of polyphenol in aqueous phase: (■) MIBK (1) + hydroquinone (2) + water (3) + toluene (4); (●) MIBK (1) + resorcinol (2) + water (3) + toluene (4); (▲) MIBK (1) + catechol (2) + water (3) + toluene (4).

1−2 1−3 1−4 2−3 2−4 3−4

1−2 1−3 1−4 2−3 2−4 3−4 1−2 1−3 1−4 2−3 2−4 3−4

Figure 5. Hand plots of the system MIBK (1) + polyphenol (hydroquinone, catechol, and resorcinol) (2) + water (3) + toluene (4).

1−2

where xi is the mole fraction of component i, and, γi is the activity coefficient of component i, T is the absolute temperature. Δgij is binary interaction parameter, which needed to be regressed. αij is nonrandomness factor, and αij is equal to αji.

bij (K)

bji (K)

RMSD

NRTL Parameters MIBK (1) + Hydroquinone (2) + Water (3) + Toluene (4) 759.333 −297.075 0.0121 440.654 1490.510 −2315.390 1242.880 291.030 1432.630 1546.400 4420.420 123.838 −233.905 MIBK (1) + Resorcinol (2) + Water (3) + Toluene (4) 781.983 −332.639 0.0129 485.498 1477.790 −1534.350 1293.700 325.176 1415.300 2006.190 4716.350 1098.720 −392.807 MIBK (1) + Catechol (2) + Water (3) + Toluene (4) 1042.950 −448.622 0.011 465.416 1481.430 942.495 −747.600 432.626 1347.880 −386.450 5482.730 1846.400 −445.805 UNIQUAC Parameters MIBK (1) + Hydroquinone (2) + Water (3) + Toluene (4) −250.349 85.050 0.0154 −1255.930 423.635 764.166 −2867.840 −111.747 −313.688 −270.414 112.081 25.461 104.637 MIBK (1) + Resorcinol (2) + Water (3) + Toluene (4) −90.720 −82.958 0.0114 −1259.680 416.873 814.082 −2372.950 −1336.890 −109.941 −2535.370 −1755.540 22.763 127.018 MIBK (1) + Catechol (2) + Water (3) + Toluene (4) −13.551

−105.893

α

0.3 0.3 0.3 0.3 0.3 0.2 0.3 0.3 0.3 0.3 0.3 0.2 0.3 0.3 0.3 0.3 0.3 0.2

0.0185

The UNIQUAC model used in this work, the activity coefficient, and required parameters are given by eqs 6. D

DOI: 10.1021/acs.jced.7b00598 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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4. CONCLUSION In this work, the LLE data for quaternary systems of water + polyphenol (hydroquinone, catechol, and resorcinol) + MIBK + toluene were measured at 298.15 K and 0.1 MPa. The mixed solvent of MIBK + toluene was used as extractive agent. In Figures 1−3 the slope of tie-lines shows that the mixed solvent can separate the polyphenol from the mixtures of water and polyphenol, and the values of D and S also show the possibility of mixed solvents to extract polyphenol from its aqueous solution. The NRTL and UNIQUAC models were used to correlate the experimental data for the systems studied in this work. The values of RMSD denote that the two models can correlate the experimental data properly. The binary interaction parameters for the two models which are essential for industrial design and optimization of the extractive process were obtained through regression of the experimental data.

Table 5. Hand and Bachman Equations Parameters for Quaternary System Hand

Bachman

component

a1

b1

R2

a2

b2

R2

hydroquinone catechol resorcinol

1.106 1.100 1.106

3.746 3.793 3.745

0.999 0.998 0.999

0.974 0.974 0.974

0.007 0.007 0.007

1.000 1.000 1.000

Φi Φ θ z + qi ln i + li − i ∑ xjl j+qi xi 2 xi j Φi ⎛ ⎛ ⎞ θ′ j Γij ⎞⎟ ⎜ ⎜ ⎟ × 1 − ln⎜∑ θ′ j Γij⎟ − ∑ ⎜ ⎟ j ∑k θk Γkj ⎠ ⎝ j ⎠ ⎝

ln γi = ln

θi =

qixi ∑j qjxj

θ′i =

q′i xi rx Φi = i i ∑j qjxj ∑j rjxj

⎛ Δuij ⎞ ⎛ Δuji ⎞ τij = exp⎜ − ⎟Γij = exp⎜ − ⎟ ⎝ RT ⎠ ⎝ RT ⎠

■

Corresponding Author

*E-mail: [email protected].

(6)

ORCID

where z is the number of close interacting molecules around a central molecule and set to 10, and Φi and θi represent the volume fraction and the area fraction of component i, respectively. Δuij is the UNIQUAC model parameter needed to be regressed. The molecular volume structure parameter r and the molecular surface area parameters q were from the reference21,22 (Table 2). The binary interaction parameters for the two models were obtained through minimizing the objective function (OF), which is defined as follows: ⎡ (w exp − w cal)2 ⎤ ijk ijk ⎥ OF = ∑ ∑ ∑ ⎢ 2 ⎢ ⎥⎦ σ w ⎣ i=1 j=1 k=1 3

2

Sheng Yang: 0000-0001-8597-0791 Peizhe Cui: 0000-0001-6390-9287 Notes

The authors declare no competing financial interest.

■

REFERENCES

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n

(7)

where n is the number of data points, wexp indicates mass fraction for experimental data, wcal indicates mass fraction for calculates data, i represents component, j expresses phase, and k denotes tie-line. The values of RMSD were calculated to estimate applicability of the NRTL and UNIQUAC models for the three systems. ⎡ ∑3 ∑2 ∑n (w exp − w cal)2 ⎤1/2 ijk ijk i=1 j=1 k=1 ⎥ RMSD = ⎢ ⎢ ⎥ 6 n ⎣ ⎦

AUTHOR INFORMATION

(8)

where w is the mass fraction of each component and the subscripts i, j, and k denote the component, phase, and tie-line, respectively. As can be seen from Table 4, the NRTL model is more suitable for MIBK + catechol + water + toluene system and the UNIQUAC model is more suitable for MIBK + resorcinol + water + toluene system. And the maximum value for RMSD is less than 2%, this shows that the two models can correlate the systems properly. There are some good reasons for a single set of parameter was used in the data regression process.34,35 The RMSD obtained using a single set of binary parameters is significantly greater than that of the respective fit, so the experimental data for each system were regressed, respectively. E

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DOI: 10.1021/acs.jced.7b00598 J. Chem. Eng. Data XXXX, XXX, XXX−XXX