Solubilities of Isophthalic Acid in Ternary Mixtures of Acetic Acid+


Mar 16, 2018 - ... the mass ratios of water to acetic acid were 0, 1:9, and 1:4, and the mass ... The experimental results indicated that the solubili...
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Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Solubilities of Isophthalic Acid in Ternary Mixtures of Acetic Acid + Water + Benzoic Acid from 292.55 to 372.10 K Shuyu Ning, Weifeng Chen, Teng Pan, Youwei Cheng,*,1 Lijun Wang, and Xi Li Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, P. R. China ABSTRACT: Solubilities of isophthalic acid in ternary mixtures of acetic acid + water + benzoic acid were determined by the static analytical method. The temperature range was from 292.55 to 372.10 K, the mass ratios of water to acetic acid were 0, 1:9, and 1:4, and the mass fractions of benzoic acid in initial solvent ranged from 0 to 20.1%. The experimental results indicated that the solubility of isophthalic acid increased with the introduction of benzoic acid to the binary solvents of acetic acid and water, and that could be explained by Hansen’s three-dimensional parameters and like-dissolves-like rule. Then the experimental solubilities were correlated by the nonrandom two liquids (NRTL) model, and the model parameters were regressed. The values calculated by the NRTL model showed good agreement with the experiment data.



INTRODUCTION Aromatic dicarboxylic acids such as terephthalic acid (TA) and isophthalic acid (IA) are used to produce various polyester products, important examples of which are polyethylene terephthalate (PET) and its copolymers.1−4 These aromatic dicarboxylic acids are produced by the catalytic oxidation of the corresponding dimethyl aromatic compounds. For example, TA and IA are produced by the liquid-phase oxidation of paraxylene (PX) and meta-xylene (MX), respectively. During liquidphase oxidation, oxidation reactors are fed with one or more aromatic hydrocarbons, fresh or recycled acetic acid water solvent, Co/Mn/Br catalyst components, and a molecular oxygen-containing gas, and also discharge crude aromatic dicarboxylic acids slurry at the same time.5−7 PX, MX, ethylbenzene (EB), and ortho-xylene (OX) are often present together in the C8 aromatic product streams. For the chemical and physical similarity of these C8 isomers, costly adsorptive separation and isomerization steps are involved in the PX production process. The selective adsorption of PX from the C8 aromatics will form a PX-depleted effluent, and the PXdepleted could return toward equilibrium concentration in an isomerization step. As MX is enriched to more than 70 wt % in the PX-depleted stream, it could be separated to produce MX and IA by further oxidation. But the expensive MX adsorptive separation process is another obstruction. Therefore, we had proposed a new oxidation process for the mixtures of MX and EB,8,9 in which the mixtures of MX and EB obtained from the PX-depleted stream could be converted into IA and benzoic acid (BA) by the liquid-phase oxidation process, and then IA and BA could be separated by crystallization. Although solubilities of IA had been reported in water, acetic acid, and the binary acetic acid + water solvents,1,10,11 the oxidation of EB was involved in the oxidation of the mixtures, and liquid-state BA was presented in the binary acetic acid + water solvent. It is © XXXX American Chemical Society

important to learn the IA solubility characteristic in ternary mixtures of acetic acid + water + benzoic acid, which is the key physical parameter to the crystallization and purification of crude isophthalic acid. Therefore, it is necessary to determine the solubility of IA in the ternary mixtures of acetic acid + water + BA.



EXPERIMENTAL SECTION

Chemicals. Isophthalic acid was supplied by Shanghai Aladdin Biological Technology Co., Ltd. Benzoic acid and acetic acid of analytical grade and phosphoric acid of guaranteed grade were supplied by Sinopharm Chemical Reagent Co., Ltd. High performance liquid chromatography (HPLC) grade methyl alcohol and acetonitrile from USA Tedia Company, Inc. were used as the flow-phase in HPLC analysis. Deionized water was used throughout all the experiments, and all the chemicals were used without further purification (Table 1). Apparatus and Procedure. The determination experiments of the solubilities were carried out in a glass bottle with a working volume of 250 mL, which had three mouths used for feeding, mechanical stirring, and temperature measurement separately. The bottle was sealed by rubber stoppers to prevent the evaporation of solvents and was put in a thermostatic oil bath which was stirred continuously. The temperature was controlled within ±0.1 K of the desired temperature with a thermoelectric controlling system, and the uncertainty in the temperature measurements was estimated to be ±0.1 K for all the experiments. The mass of chemicals required in the experiments was determined by an electronic analytical balance Received: November 3, 2017 Accepted: March 9, 2018

A

DOI: 10.1021/acs.jced.7b00958 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 1. Description of Materials Used in This Worka

a

chemical name

CASRN

source

mass fraction purity

purification method

analysis method

isophthalic acid benzoic acid acetic acid phosphoric acid methyl alcohol acetonitrile

121-91-5 65-85-0 64-19-7 7664-38-2 67-56-1 75-05-8

Shanghai Aladdin Biological Technology Co., Ltd. Sinopharm Chemical Reagent Co., Ltd. Sinopharm Chemical Reagent Co., Ltd. Sinopharm Chemical Reagent Co., Ltd. USA Tedia Company, Inc. USA Tedia Company, Inc.

≥0.990 ≥0.995 ≥0.995 ≥0.85 ≥0.999 ≥0.999

none none none none none none

GCb

GCb GCb

Both the analysis method and the mass fraction purity were provided by the suppliers. bGas−liquid chromatography.

with an uncertainty of 0.0001 g. When the solid−liquid equilibrium was reached, the upper clarified liquid was sampled and analyzed by HPLC. The reliability of the experimental apparatus had been verified in our previous work.12,13 Solubility Measurements. For each solubility experiment, excessive amount of IA was added into the preprepared solvent (150 mL) in a three-mouth flask. Then the equilibrium flask was set in the precision thermostatic oil bath to maintain the temperature. When the oil reached the specified temperature, the mechanical stirrer was turned on to stir the solid−liquid mixtures at a speed of 200 rpm for a period, and then it was switched off to keep the mixtures still for another period. Finally, the upper clarified liquid was sampled and diluted with methanol for further quantitative analysis. The concentration of IA in the samples was determined by a Agilent 1100 Series high performance liquid chromatograph, and every sample was analyzed twice, in which the relative error was within ±1%. An Agilent SB-C18 analytical HPLC column (4.6 mm × 250 mm) and a DAD detector were used. Gradient elution was used for complete separation of the samples at room temperature, and the flow rate of mobile phase was 1.00 mL/min. The flow phase consisted of methanol, water (consisted of 0.1% phosphoric acid), and acetonitrile, and the following gradient elution program was adopted: from 0 to 3 min, 10% methanol, 70% water, and 20% acetonitrile; from 3 to 8 min, the mixture composition changed linearly with time to become 20% methanol, 50% water and 30% acetonitrile; from 8 to 12 min, the mixture composition changed linearly with time to become 35% methanol, 25% water, and 40% acetonitrile; and from 12 min on, the composition of the flow phase remained unchanged. Each analysis took about 15 min, and the retention time of IA in the HPLC chromatogram was about 5.7 min.

Figure 1. Influence of stirring time on the determination of the solubility of isophthalic acid in acetic acid at 328.15 K when standing time was 60 min.

Figure 2. Influence of standing time on the determination of the solubility of isophthalic acid in acetic acid at 328.15 K when stirring time was 60 min



RESULTS AND DISCUSSION Credibility Analysis. To determine the appropriate operating conditions to achieve phase equilibrium, the influence of the time for stirring and standing on the determination of IA was investigated before the experiments. The typical experiment point that determined the solubility of IA in acetic acid at 328.15 K was chosen as the object, and the results were shown in Figure 1 and 2, which indicated that stirring 30 min and standing 50 min could lead the solution to balance fully. In the following solubility experiments, stirring 60 min and standing 90 min were adopted to ensure the accuracy of the solubility data. To verify the reliability of the above experimental method, the solubilities of IA in pure acetic acid determined by the above method was compared with the previous works.10,11 The results (Figure 3) show that the experimental data are in good agreement with the previous literature, and the maximum relative deviation is less than 3%, which may result from measurement errors and the differences in experimental

Figure 3. Determined solubilities and literature data of isophthalic acid in pure acetic acid: ○, experimental data of this work; □, experimental data of reference 10; −, calculation data of reference 10; △, experimental data of reference 11; dash line, calculation data of reference 11.

methods. So, this method is credible and could be adopted in further solubility determined experiments. B

DOI: 10.1021/acs.jced.7b00958 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 2. Mole Fraction Solubilities of Isophthalic Acid (1) in Acetic Acid (2) + Benzoic Acid (4) Binary Solvent Mixtures at Temperature T and Pressure p = 0.1 MPaa ω4 0

0.050

0.100

T/K

xexp×104

xcal×104

δRD/%

ω4

T/K

xexp×104

xcal×104

δRD/%

292.55 301.85 311.55 321.55 331.35 342.50 352.50 362.05 372.10 295.50 304.00 312.90 322.75 332.45 342.65 352.50 362.10 371.95 293.65 304.05 312.90 322.90 332.70

6.05 7.74 10.23 13.23 17.49 24.13 31.37 40.71 51.91 6.83 8.86 11.70 14.84 19.22 24.79 32.00 41.04 51.92 7.05 9.59 12.46 16.28 20.71

5.67 7.68 10.37 13.89 18.22 24.41 31.31 39.28 49.35 6.74 8.82 11.51 15.22 19.74 25.62 32.58 40.84 51.20 6.80 9.43 12.24 16.18 20.96

−6.22 −0.71 1.34 4.98 4.17 1.16 −0.17 −3.50 −4.93 −1.22 −0.50 −1.64 2.51 2.74 3.35 1.80 −0.47 −1.39 −3.61 −1.69 −1.74 −0.59 1.19

0.100

342.70 352.45 362.25 371.90 297.50 303.40 314.45 322.85 332.50 342.45 352.50 362.40 371.85 298.55 304.10 314.05 322.85 332.65 342.50 352.50 362.05 372.10

26.35 33.30 43.81 55.56 7.84 9.68 13.40 16.92 21.63 28.10 35.14 44.34 57.92 8.77 10.52 14.16 18.24 23.20 29.76 37.85 48.71 61.29

26.95 34.14 43.06 54.02 8.15 9.79 13.51 17.02 21.90 28.08 35.85 45.50 57.26 8.85 10.49 13.99 17.78 22.92 29.30 37.44 47.38 61.17

2.28 2.50 −1.72 −2.77 4.04 1.08 0.88 0.59 1.26 −0.07 2.01 2.62 −1.14 0.86 −0.32 −1.15 −2.49 −1.20 −1.52 −1.08 −2.73 −0.20

0.150

0.201

a ω4 is the mass fraction of BA in the initial solvent; xexp and xcal are experimental and calculated values of mole fraction solubility, respectively; δRD is the relative deviation. The standard uncertainty for temperature is u(T) = 0.1 K. The relative standard uncertainty of ω4 is ur(ω4) = 0.01. The relative standard uncertainty for pressure and solubility are ur(p) = 0.05 and ur(x) = 0.03, respectively.

Table 3. Mole Fraction Solubilities of Isophthalic Acid (1) in Acetic Acid (2) + Water (3) + Benzoic Acid (4) Ternary Solvent Mixtures Where the Mass Ratio of Water to Acetic Acid Was 1:9 at Temperature T and Pressure p = 0.1 MPaa ω4 0

0.046

0.100

T/K

xexp×104

xcal×104

δRD/%

ω4

T/K

xexp×104

xcal×104

δRD/%

292.75 302.05 311.45 322.25 331.95 341.75 352.05 361.45 370.95 292.85 302.25 312.05 321.65 331.25 342.25 352.05 361.95 370.95 292.85 301.55 312.25 321.95

4.53 6.33 8.25 11.40 15.17 20.20 26.08 33.96 43.59 4.89 6.77 9.04 12.09 16.21 21.94 28.80 39.23 50.73 5.31 7.08 9.77 13.08

4.53 6.13 8.24 11.48 15.32 20.34 27.16 35.09 45.12 4.95 6.66 9.01 12.02 15.94 21.85 28.74 37.67 47.94 5.40 7.07 9.76 13.00

−0.13 −3.18 −0.09 0.73 0.98 0.74 4.16 3.35 3.51 1.02 −1.63 −0.32 −0.51 −1.66 −0.41 −0.22 −3.98 −5.49 1.56 −0.24 −0.04 −0.62

0.100

331.65 341.65 351.55 360.85 369.85 292.75 302.35 312.05 321.65 331.35 340.75 351.85 360.75 369.85 302.85 312.35 321.85 331.95 342.95 352.65 362.15 371.95

17.21 22.63 29.55 39.46 51.13 5.77 7.77 10.27 14.06 18.27 23.76 31.39 41.88 53.83 8.26 11.02 14.82 18.50 26.27 33.06 44.28 57.20

17.19 22.81 30.03 38.76 49.56 5.79 7.76 10.36 13.69 18.05 23.49 31.96 40.87 52.63 8.37 11.06 14.53 19.32 26.23 34.32 44.76 59.19

−0.07 0.80 1.63 −1.76 −3.07 0.38 −0.19 0.82 −2.66 −1.19 −1.11 1.83 −2.41 −2.22 1.33 0.42 −1.94 4.43 −0.16 3.82 1.09 3.47

0.149

0.199

ω4 is the mass fraction of BA in the initial solvent; xexp and xcal are experimental and calculated values of mole fraction solubility respectively; δRD is the relative deviation. The standard uncertainty for temperature is u(T) = 0.1 K. The relative standard uncertainty of ω4 is ur(ω4) = 0.01. The relative standard uncertainty for pressure and solubility are ur(p) = 0.05 and ur(x) = 0.03, respectively. a

calculated values of mole fraction solubility, respectively, and ω4 stands for the mass fraction of BA in the initial solvent. The data in the tables present that within the temperature range of

Solubility Data. The solubility data of IA in binary mixtures of acetic acid + BA and ternary mixtures of acetic acid + water + BA are shown in Tables 2−4. xexp and xcal are experimental and C

DOI: 10.1021/acs.jced.7b00958 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 4. Mole Fraction Solubilities of Isophthalic Acid (1) in Acetic Acid (2) + Water (3) + Benzoic Acid (4) Ternary Solvent Mixtures Where the Mass Ratio of Water to Acetic Acid Was 1:4 at Temperature T and Pressure p = 0.1 MPaa ω4 0

0.050

0.100

T/K

xexp×104

xcal×104

δRD/%

ω4

T/K

xexp×104

xcal×104

δRD/%

297.40 304.05 313.35 322.40 332.10 341.85 351.75 361.60 370.20 295.65 303.60 312.90 322.55 332.20 342.00 351.90 360.50 369.95 294.15 303.60 312.85 322.25

4.13 5.42 7.56 10.11 12.97 18.06 24.10 32.17 42.61 4.40 6.09 8.93 11.36 15.22 19.98 26.71 35.67 45.52 4.82 6.89 9.11 12.10

4.32 5.45 7.47 10.04 13.64 18.35 24.56 32.49 41.18 4.58 6.01 8.17 11.11 14.96 20.04 26.70 34.07 44.28 4.86 6.66 8.97 12.02

4.67 0.49 −1.17 −0.61 5.12 1.61 1.90 1.00 −3.35 4.09 −1.35 −8.58 −2.20 −1.73 0.31 −0.04 −4.49 −2.72 0.87 −3.29 −1.52 −0.62

0.100

332.25 342.10 351.90 361.45 370.80 302.90 312.45 322.30 331.75 341.60 351.35 361.10 370.60 317.45 322.10 331.55 341.50 346.40 351.40 361.10 366.65 370.45

16.07 21.08 28.15 37.56 49.43 7.12 9.51 13.04 17.01 22.31 30.50 39.96 51.84 12.02 13.97 18.48 24.86 28.06 32.45 41.68 48.23 54.48

16.25 21.70 28.74 37.63 48.88 7.14 9.64 13.01 17.21 22.88 30.21 39.80 52.11 12.06 13.84 18.22 24.21 27.82 32.05 42.23 49.54 55.32

1.12 2.90 2.08 0.17 −1.13 0.22 1.39 −0.25 1.18 2.57 −0.96 −0.41 0.52 0.35 −0.94 −1.40 −2.61 −0.88 −1.24 1.34 2.71 1.54

0.150

0.200

ω4 is the mass fraction of BA in the initial solvent; xexp and xcal are experimental and calculated values of mole fraction solubility, respectively; δRD is the relative deviation. The standard uncertainty for temperature is u(T) = 0.1 K. The relative standard uncertainty of ω4 is ur(ω4) = 0.01. The relative standard uncertainty for pressure and solubility are ur(p) = 0.05 and ur(x) = 0.03, respectively. a

In eq 2, x1, x2, x3, and x4 are respectively the mole fractions of IA, water, acetic acid, and BA when the solution reaches equilibrium. Gij and τij are the model parameters of the NRTL equation, which can be calculated by the following equations.

the measurements (from 292.55 to 372.10 K), the solubilities of IA in all the mixtures showed an increasing trend as the temperature increased, which was the same as the phenomenon of the solubilities of IA in acetic acid + water binary solvents.1 Correlation of Experimental Data. Generally, according to the thermodynamic description of solid−liquid equilibrium, it can be approximately expressed by an equation that involves the properties of pure solute, such as enthalpy of fusion △fusH, melting point Tfus, etc. In the solution mixtures, there was only IA in the solid phase, so the equilibrium equation could be reduced to eq 1.14,15 ln(γ1x1) = −

ΔfusH ⎛ 1 1 ⎞ ⎟ ⎜ − R ⎝T Tfus ⎠

Gij = exp( −αijτij),

τij =

4

∑ j = 1 τj1Gj1xj 4 ∑k = 1 Gk1xk

4

+

∑ j=1

(3)

gij − gjj (4)

RT

In eq 3, when the experimental value is not enough, the value of αij can be fixed at 0.3, which has been recommended by Renon and Prausnitz.19,20 In eq 4, gij is an energy parameter characterizing the interaction of substance i and j, and (gij − gjj) is linearly related to temperature which can be easily obtained from the report of Renon and Prausnitz, thus eq 4 can be simplified as eq 5.14

(1)

In eq 1, γ1 is the activity coefficient of solute; x1 is the real mole fraction of solute in the solution which was expressed as xexp in this work; R is the ideal gas constant (R = 8.314 J/(mol·K)); T is the absolute temperature; △fusH is the molar enthalpy of fusion of solute; and Tfus is the fusion temperature. It has been obtained from the literature that the molar enthalpy of fusion of IA is 43200 J/mol and the melting point of IA is 617.41 K.16 There are many equations that could express the relationship between activity coefficients and mole fractions,17,18 and the nonrandom two-liquid (NRTL) equation and Wilson equation are adopted often. NRTL can be applied in both partially miscible and completely miscible mixtures. The NRTL activity coefficient model used in this work is expressed as follows.19 Inγ1

αij = αji

τij = a ij +

bij T

(5)

In eq 5, aij and bij are the binary interaction parameters of the NRTL equation. Using eq 1, eq 2, eq 3, and eq 5 as model equations, all the solubility data of IA in acetic acid + BA binary mixtures and acetic acid + water + BA ternary mixtures were correlated. The model parameters were optimized by the leastsquares method in MATLAB, and the objective function used in the optimization process was defined as eq 6. 2⎫ ⎧ n ⎡ xexp, i − xcal, i ⎤ ⎪ ⎪ ⎢ ⎥ ⎬ F = min⎨∑ ⎪ i = 1 ⎢⎣ xexp, i ⎥⎦ ⎪ ⎩ ⎭

4 ⎛ ∑ xτ G ⎞ ⎜τ1j − k = 1 k kj kj ⎟ 4 4 ∑k = 1 Gkjxk ⎟⎠ ∑k = 1 Gkjxk ⎜⎝

xjGij

(6)

In eq 6, n is the number of experimental points, xexp,i and xcal,i are respectively experimental and calculated values of mole

(2) D

DOI: 10.1021/acs.jced.7b00958 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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fraction solubility in each experiment. The regressed results of which were presented in Table 5. And the comparison between the calculated results and the experimental data are also shown in Figures 4−6. Table 5. Binary Parameters of the NRTL Model for the Quaternary Mixtures IA (1) + Acetic Acid (2) + Water (3) + BA (4) i

j

aij

aji

bij/K

bji/K

IA IA IA H2O H2O HAc

H2O HAc BA HAc BA BA

0.3330 0.2513 −0.9198 5.669 1.966 3.606

0.4855 4.655 −28.28 −2.843 −3.211 −4.481

−505.8 −480.1 −220.8 −4220 −22.19 418.5

350.5 −1293 1.131 × 104 3297 732.3 −191.3

Figure 6. Mole fraction solubilities of isophthalic acid in acetic acid + water + benzoic acid ternary solvent mixtures where the mass ratio of water to acetic acid was 1:4 at the temperature T and pressure p = 0.1 MPa; ■, 0% BA; ●, 5.0% BA; ▲, 10.0% BA; □, 15.0% BA; ○, 20.0% BA; −, calculated from the NRTL model.

with the experimental values. The NRTL model with binary parameters could be well applied to correlate the experimental data.



DISCUSSION From Figures 4 to 6, it is found that the introduction of BA in the solvents increased the solubilities of IA, and the more BA dissolved in the solutions, the higher were the solubility values of IA determined within the experimental range of the mass fraction of BA (from 0 to 20.1%). This phenomenon can be explained by solubility parameters. The Hildebrand solubility parameter (δ) is defined as the square root of the cohesive energy density, which could provide a numerical estimate of the degree of interaction between nonpolar materials and predict the miscibility of materials from the similarity of the parameters.21,22 Since the solvents in this work were polar materials, the Hildebrand solubility parameter cannot be well applied to the systems. Hansen’s threedimensional solubility parameters theory is applicative in this circumstance, which takes into account interactions such as dispersion, polarity, and hydrogen bonding. The Hansen’s three-dimensional parameters of these materials were listed in Table 6, and the parameters consisted of dispersion (δd), polar

Figure 4. Mole fraction solubilities of isophthalic acid in acetic acid + benzoic acid binary solvent mixtures at the temperature T and pressure p = 0.1 MPa: ■, 0% BA; ●, 5.0% BA; ▲, 10.0% BA; □, 15.0% BA; ○, 20.1% BA; −, calculated from the NRTL model.

Table 6. Hansen Solubility Parameters for The Materials of This Work

Figure 5. Mole fraction solubilities of isophthalic acid in acetic acid + water + benzoic acid ternary solvent mixtures where the mass ratio of water to acetic acid was 1:9 at the temperature T and pressure p = 0.1 MPa; ■, 0% BA; ●, 4.6% BA; ▲, 10.0% BA; □, 14.9% BA; ○, 19.9% BA; −, calculated from the NRTL model.

The relative deviation (RD) between the experimental value xexp and the calculated value xcal and the average relative deviation (ARD) are defined as follows. RDi % =

xexp, i − xcal, i xexp, i

ARD =

δt

δd

δp

δh

29.34 21.81 47.80 21.40 23.64 26.06

25.32 18.19 15.60 14.52 14.63 14.74

1.60 6.99 15.99 7.97 8.77 9.57

14.74 9.81 42.28 13.49 16.37 19.25

(δp), and hydrogen bonding (δh) components, and their total solubility parameters could be calculated by eq 8.

n

× 100,

materials isophthalic acid benzoic acid water acetic acid acetic acid/water(9:1 wt/wt) acetic acid/water(4:1 wt/wt)

1 ∑ abs(RDi) n i=1

δd 2 + δp2 + δ h 2

δt = (7)

The relative deviations for all experimental points are summarized in Tables 2−4, and the average relative deviation is 1.78%, which reflects that the calculated values coincide well

δd =

∑ Φiδd,i , δp = ∑ Φiδp,i , δ h = ∑ Φiδ h,i i

E

(8)

i

i

(9)

DOI: 10.1021/acs.jced.7b00958 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Here, Φi represents the volume fraction of each solvent in the solution, and δd,i, δp,i, δh,i are the Hansen’s three-dimensional parameters of each solvent in the solution. In Table 6, the solubility parameters of pure materials IA, BA, water, and acetic acid were acquired from the relative literature,21,23 while the Hansen parameters of acetic acid + water mixture solvents were calculated by eqs 8 and 9.23 Likewise, the Hansen parameters of acetic acid + BA and acetic acid + water + BA mixtures were calculated, and the results were compared and shown in Figure 7.

data and the correlation equations in this work could be used for analyzing and simulating the separation and purification process of IA in the MX-EB mixed oxidation process.



AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected] ORCID

Youwei Cheng: 0000-0001-7494-3974 Notes

The authors declare no competing financial interest.



REFERENCES

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Figure 7. Ratio δd /δt in different mixture solvents: □, acetic acid + BA; ○, acetic acid + water + BA where mass ratio of water to acetic acid was 1:9; △, acetic acid + water + BA, where mass ratio of water to acetic acid was 1:4.

As a substance with low polarity, IA’s intermolecular force mainly comes from dispersion forces. Similar with that in IA, the intermolecular forces in BA are also mainly dispersion forces, while hydrogen bonding and dispersion forces dominate the interactions between the molecules in acetic acid and acetic acid + water mixture solvents. Just as shown in Figure 7, with the increase of BA mass fraction in the mixture solvents, the ratio of dispersion forces in the intermolecular forces increased to approach the value of IA (δd /δt = 0.86). Therefore, the miscibility of IA and the mixture solvents increased according to the like-dissolves-like rule, which is reflected as the solubility of IA increased in the phase equilibrium. On the contrary, the δh value of the solvents increased significantly with the increase of water content, that could be caused by the hydrogen bonds between water molecules and between water and acetic acid molecules.



CONCLUSION In the present work, solubilities of IA in binary mixtures of acetic acid + BA and ternary mixtures of acetic acid + water + BA were determined. For the binary solvents of acetic acid + water, significant changes in the solubility of IA were observed as BA was introduced. The addition of BA favored the solubilization of IA, and more BA composition in the solvents would result in more IA in the solution within the experimental range. This phenomenon could be explained by Hansen’s threedimensional parameters theory and like-dissolves-like rule. As BA increases in the ternary mixtures of acetic acid + water + BA, the Hansen’s three-dimensional parameters (δ) of the mixtures approach to the values of IA, meaning that the miscibility between the solvents and IA increases and the solubility of IA in the ternary mixtures increases. Furthermore, the experimental solubilities were correlated by the NRTL model, and the results showed that this model was very applicable to these quaternary mixtures. These experimental F

DOI: 10.1021/acs.jced.7b00958 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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DOI: 10.1021/acs.jced.7b00958 J. Chem. Eng. Data XXXX, XXX, XXX−XXX