SolidâLiquid Phase Equilibria of Ternary Mixtures Containing 1,2

Article pubs.acs.org/jced

Solid−Liquid Phase Equilibria of Ternary Mixtures Containing 1,2‑Dihydroacenaphthylene and Dibenzofuran Wenjie Cong,† Qiuxiang Yin,†,‡ Junbo Gong,†,‡ Ying Bao,†,‡ Meijing Zhang,†,‡ Hongxun Hao,†,‡ Baohong Hou,†,‡ Yuhong Guo,† and Chuang Xie*,†,‡ †

School of Chemical Engineering & Technology, State Key Laboratory of Chemical Engineering, Tianjin University Collaborative Innovation Center of Chemical Science and Chemical Engineering (Tianjin), Tianjin 300072, People’s Republic of China

‡

S Supporting Information *

ABSTRACT: Ternary phase diagram data of 1,2-dihydroacenaphthylene-dibenzofuran mixtures in a series of alcohols, including methanol, ethanol, propan-2-ol, propan-1-ol, butan-1-ol, and pentan-1-ol were measured using a dynamic method at 308.15 and 313.15 K. The experimental data were correlated with the Wilson model (including pseudobinary systems), UNIQUAC model, and NRTL model. The results indicate that pseudobinary systems with the Wilson equation give a better description of the solubility of the ternary system. The eutectic point shifts toward dibenzofuran when the more polar methanol and ethanol are used. This shift may help achieve a more efficient separation of 1,2-dihydroacenaphthylene and dibenzofuran.

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INTRODUCTION Coal tar, the byproduct of coking coal industry, is a complicated mixture of a large number of phenols, polycyclic aromatic hydrocarbons (PAHs), and heterocyclic compounds. Wash oil is one of the most important distillation fractionations during the recycling of coal tar. It is an important source of common PAHs, and the only source of some special PAHs.1,2 The efficient separation of PAHs from wash oil is not only important to the recycling of the PAHs, but also helpful to environment protection. 1,2-Dihydroacenaphthylene (ANTH) and dibenzofuran (DBF) are the main PAH components in wash oil. ANTH (C12H10, CAS Registry No. 83-32-9, Figure 1) is a white needlelike crystal, which plays an important role in the production of photoelectric materials, pharmaceuticals, intermediate dyes, etc.3 DBF (C12H8O, CAS Registry No.132-64-9, Figure 1), a

white lamellar crystal, is the important raw materials for the synthesis of resin. The separation of ANTH and DBF from wash oil has received much attention and could be achieved via different methods such as rectification, extraction, crystallization, and the coupling of these methods.4 Among these methods, however, crystallization may be more suitable in industry on considering the low cost and the high product purity.5,6 To develop a crystallization process, the solid−liquid equilibria (SLE) data are necessary and should be well determined. The SLE for some ANTH/DBF-contained systems have been reported.7,8 The ANTH−DBF binary mixture was found as a simple eutectic system with an eutectic point of 0.421 (molar fraction of ANTH) at 328.2 K.8 Solubilities of single solute in pure solvents are available, such as ANTH in chloroderivative9 solvents, organic solvents,10,11 and solvent mixtures,12 DBF in different organic solvents,7,13 water,14 and supercritical carbon dioxide.12 For systems containing multisolutes, DBF-dibenzothiphene-benzene and DBF-fluorenebenzene were determined.15,16 There is little SLE data available for systems containing both ANTH and DBF. Received: January 13, 2014 Accepted: March 17, 2014 Published: March 25, 2014

Figure 1. Chemical structure of ANTH and DBF. © 2014 American Chemical Society

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dx.doi.org/10.1021/je500044s | J. Chem. Eng. Data 2014, 59, 1347−1352

Journal of Chemical & Engineering Data

Article

Table 1. Description of Materials Used in This Paper chemical name

source

1,2-dihydroacenaphthylene dibenzofuran methanol ethanol propan-1-ol propan-2-ol butan-1-ol pentan-1-ol

Baoshun Technology Co., Ltd. Aladdin Industrial Inc. Shanghai, China Tianjin Kewei Chemical Co., China Tianjin Kewei Chemical Co., China Tianjin Kewei Chemical Co., China Tianjin Kewei Chemical Co., China Tianjin Kewei Chemical Co., China Tianjin Kewei Chemical Co., China

a

initial mass fraction purity > > > > > > > >

0.980 0.980 0.997 0.997 0.997 0.998 0.996 0.996

purification method

final mass fraction purity

analysis method

recrystallization recrystallization none none none none none none

>0.997 >0.997

GCa GCa GCa GCa GCa GCa GCa GCa

Gas−liquid chromatography.

Table 2. Thermodynamic Properties of Components Used in This Work chemical name ANTH DBF methanol ethanol propan-2-ol propan-1-ol butan-1-ol pentan-1-ol

Tm/(K) 11

366.65 355.7021 176.427 158.827 185.2527 146.1527 184.2527 194.827

ΔHm/(J·mol−1)

149.8011 152.513 40.727 58.727 76.9027 75.1027 92.027 108.527

14.855 9.6016

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THERMODYNAMIC MODELS The solubility of solute i in a liquid can be expressed by ΔHmi ⎛ 1 1⎞ − ⎟ ⎜ R ⎝ Tmi T⎠

ln xi = −ln γi + −

■

⎞ ΔC Pi ⎛ Tmi T ⎜ln − mi + 1⎟ ⎝ ⎠ R T T

(2)

where γi, Tmi, ΔHmi, ΔCpi, and T stand for the activity coefficient, melting point, enthalpy of fusion, solute heat capacity difference between the solid and the liquid at the melting point of the solute, and equilibrium temperature, respectively. On the basis of eq 2, the activity coefficient of the solute in the liquid phase must be known to calculate the solubility. To express the activity coefficient as a function of temperature and solution composition, “local composition” models such as the Wilson, NRTL, and UNIQUAC models15 were applied. These models were used in this study to calculate the activity coefficient. The Wilson model, UNIQUAC model, and NRTL model were tested to describe the ternary SLE quantitatively. The characteristics of the compounds were collected in Table 2. The thermodynamic properties of solvents can be found in ref 6. Wilson Model. The Wilson model can be expressed in the following form:

EXPERIMENTAL SECTION Materials. Table 1 shows the description of materials used in the paper, including ANTH, DBF, methanol, ethanol, propan-2-ol, propan-1-ol, butan-1-ol, and pentan-1-ol. Solubility Measurements. Solubilities were determined by the dynamic (synthetic) method.17−19 Preweighed mixtures of ANTH and DBF were added into an excess of solvent to form a clear solution by maintaining the system at a fixed temperature for more than 1.44·104 s under magnetic stirring. An additional small amount of ANTH and DBF mixture with the same composition was precisely weighed and placed into the solution for 3.6·103 s to dissolve. This step was repeated until the additional solid cannot completely dissolve. And this ensures the solution is saturated for at least one of the solutes whether it is ANTH or DBF. At this point, the molar fraction solubility can be calculated according to eq 1: m1/M1 3 ∑i = 1 mi /Mi

Vi/(cm3·mol−1)

9

21860 1860021

In this work, the SLE of ANTH−DBF mixtures in a series of alcohols, including methanol, ethanol, propan-1-ol, propan-2-ol, butan-1-ol, and pentan-1-ol, were determined at 308.15 K and 313.15 K by using a dynamic method. The experimental data was correlated and interpreted using the Wilson model, the UNIQUAC model, and the NRTL model. These SLE data could be useful for the separation process of ANTH and DBF mixtures from wash oil.

x1 =

ΔCp/(J·mol−1·K)

11

ln γi = 1 − ln(∑ Λijxj) −

(1)

j

where m and M represent the mass and the molecular weight of the components, respectively. The numerator is related to the solute components. Each solubility measurement was repeated three times. The accuracy of temperature measurements is ± 0.1 K using a JULABO Circulator (type CF41). All of the masses were determined using a balance (model ML204, Mettler-Toledo, Switzerland) with an accuracy of ± 1·10−7 kg.

∑ k

Λkixk ∑j Λkjxj

(3)

where Λij is expressed as Λij =

Vj Vi

exp[− (gij − gii)/RT )] =

Vj Vi

exp[−Δgij /RT )] (4)

where Vi and Vj are the mole volumes of component i and j (their values have been given in Table 2). gij − gii is the cross1348



Article n

interaction energy parameter in the ternary solution. The ternary solution contains three binary systems. Each binary system has two parameters. Thus six parameters in total are needed to describe the ternary system. We also correlated these ternary data using pseudobinary systems.20 These pseudobinary samples were prepared with constant mass ratios (MS) of ANTH/DBF (for example, MS: 1:9; 3:7; 4:6; 5:5; 6:4). The activity coefficient was calculated by the Wilson model, and the interaction parameters were fitted to the pseudobinary system by the application of least-squares method. Activity coefficients obtained from the ternary data were used to predict the ternary solubility by using eq 2. Thermodynamic properties needed in eq 2 were determined by the mixture law. ΔHP = x1(ΔHm1) + x 2(ΔHm2)

(5)

MP = x1M1 + x 2M 2

(6)

VP = x1V1 + x 2V2

(7)

ln γi =

∑ j τjiGjixj n

∑l Glixl

n

+

∑ j

n ∑r xrτrjGrj ⎤ xjGij ⎡ ⎢ ⎥ τ − ij n n ∑l Gljxl ⎥⎦ ∑l Gljxl ⎢⎣

(11)

with Gij = exp( −ατij) τij =

gij − gjj

=

(12)

Δgij

(13) RT RT where i = 1, 2, 3, j = 1, 2, 3, and Δg12, Δg21, Δg13, Δg31, Δg23, and Δg32 are the cross interaction energy parameters; α is the parameter related to the nonrandomness of the solution. In the optimization process, α was usually chosen as fixed values. In this work, α values equal to 0.4, 0.5, 0.6 were used for the correlation of every ternary system of ANTH−DBF−solvent.

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RESULTS AND DISCUSSION Figures 2 to 4 show the solubility of ANTH and DBF mixtures in the six alcohols at 308.15 K and 313.15 K. In all the solvents

where ΔHp is the enthalpy of fusion of pseudobinary mixture, Mp is the molar weight of pseudobinary mixture, and Vp is the molar volume of the mixture. The melting point needed was calculated by interpolation of the binary solid−liquid equilibrium data8 and listed in the Supporting Information. UNIQUAC Model. The UNIQUAC model can be expressed as ln γi = ln

Φi Φ θ ⎛Z⎞ + ⎜ ⎟qi ln i + li − i ⎝ ⎠ Φi xi xi 2

− qi ln(∑ θτ j ji) + qi − qi ∑ j

∑ xjlj j

∑k θkτkj

(8)

Z (ri − qi) − (ri − 1) 2

li =

θi =

qixi ∑j qjxj

;

Φi =

Figure 2. Ternary phase diagram of the ANTH−DBF mixture in methanol and ethanol. The solid lines are calculated values based on the Wilson model: ○, methanol; △, ethanol; x1, molar fraction of DBF in the solution; x2, molar fraction of ANTH in the solution; x3, molar fraction of solvent in the solution.

θτ j ij

(9)

rx i i ; ∑j rjxj

⎛ uji ⎞ ⎟ τji = exp⎜ − ⎝ RT ⎠

(10)

where ri and qi are connected with molecular van der Waals volumes and molecular surface areas, the values of which have been given in Table 3. NRTL Model. The NRTL model can be expressed in the following form: Figure 3. Ternary phase diagram of ANTH−DBF mixture in propan2-ol and propan-1-ol. The solid lines are calculated values based on the Wilson model: □, propan-2-ol; ▲, propan-1-ol; x1, molar fraction of DBF in the solution; x2, molar fraction of ANTH in the solution; x3, molar fraction of solvent in the solution.

Table 3. Solute and Solvent Properties Used in the UNIQUAC Modela chemical name

ri

qi

ANTH DBF methanol ethanol propan-1-ol propan-2-ol butan-1-ol pentan-1-ol

5.9922 5.8023 1.4324 2.575525 3.249926 3.249126 3.924326 4.598726

3.9622 3.9923 1.4324 2.58825 3.12826 3.12426 3.66826 4.20826

investigated, the mixtures form simple eutectic systems. The solubility increases with increasing temperature. At a given temperature, the order of solubility in these alcohols is pentan1-ol > butan-1-ol > propan-1-ol > propan-2-ol > ethanol > methanol. This is basically consistent with the order of relative polarity of these solvents. In other words, the mixture’s solubility increases with the increasing polarity (lengths of the alkyl group) of these alcohols. This behavior can generally be explained using the empirical rule “like dissolves like” according

a

ri and qi are structural (area and volume) parameters used in the UNIQUAC model. 1349



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Table 6. APDs of Pseudobinary Mixtures in Different Solvents

a

Figure 4. Ternary phase diagram of ANTH−DBF mixture in butan-1ol and pentan-1-ol. The solid lines are calculated values based on the Wilson model: +, butan-1-ol; ■, pentan-1-ol; x1, molar fraction of DBF in the solution; x2, molar fraction of ANTH in the solution; x3, molar fraction of solvent in the solution.

1 N

N

∑ i=1

xical − xiexp 100 xiexp

MSa = 2:8

MSa = 4:6

MSa = 5:5

MSa = 6:4

methanol ethanol propan-1-ol propan-2-ol butan-1-ol pentan-1-ol

0.039 0.0063 0.016 0.029 0.007 0.017

0.043 0.0053 0.033 0.017 0.0119 0.042

0.035 0.0076 0.007 0.008 0.0044 0.009

0.006 0.0112 0.035 0.003 0.0093 0.045

MS is mass ratio of ANTH/DBF.

along the respective saturated curves in the ternary systems. Table 4 shows that the Wilson model fits the experimental data well within 6% APD in all the solvents except pentanol. However, the UNIQUAC model and the NRTL model cannot predict the solubility satisfactorily (as shown in Tables 4 to 5) in all the investigated systems. Table 6 reports the calculated solubility based on the pseudobinary treatment (see Experimental Section). The APD ranges from 0.7 % to 4.0 % which indicates a good agreement between the experimental data and the calculated values. Figure 5 shows the calculated eutectic compositions (mole ratio of ANTH in the solute mixture) versus the relative

to the poor polarity of ANTH and DBF. The only exception is propan-2-ol, which may be attributed to the steric-hindrance effect of the solvent. The Wilson model, UNIQUAC model, and NRTL model were used to correlate the solubility data. The model parameters (shown in the Supporting Information) were obtained by using a nonlinear least-squares method to minimize the objective function f = (xcal − xexp)/xexp. The average percent deviation (APD), a parameter to evaluate the applicability and accuracy of the models, is defined as APD (%) =

solvent

(14)

where N refers to the number of experimental points for each exp solvent; xcal stand for the calculated and experimental i and xi solubility, respectively. The APDs of different correlation models are shown in Tables 4 to 6. Table 4. APDs of Wilson Model and UNIQUAC Model for ANTH−DBF−Solvent System Wilson model

UNIQUAC model

solvent

308.15 K

313.15 K

308.15 K

313.15 K


0.07787 0.05916 0.05491 0.05313 0.05046 0.14041

0.03756 0.03658 0.05345 0.05102 0.06729 0.18242

0.16986 0.15525 0.15868 0.13364 0.33532 0.14731

0.14029 0.17542 0.15921 0.13717 0.30822 0.08350

Figure 5. Experimental eutectic compositions versus the relative polarity of solvents. xexp E is the molar fraction of ANTH in the ANTH− DBF mixture at the eutectic point, and εr is the relative polarity of solvents.

polarity of the six alcohols. Noteworthily, the eutectic composition is dependent on the solvent. For less polar propan-1-ol, propan-2-ol, butan-1-ol, and pentan-1-ol, the eutectic compositions stay constant (at 0.42 of ANTH−DBF binary system). While for more polar solvents like methanol

Figures 2 to 4 compare the experimental data (discrete points) to the calculated values (lines) via the Wilson model

Table 5. APDs of the NRTL Model for the ANTH−DBF−Solvent System αa = 0.4

a

αa = 0.5

αa = 0.6

solvent

308.15 K

313.15 K

308.15 K

313.15 K

308.15 K

313.15 K


0.14690 0.25107 0.22026 0.22023 0.21384 0.08296

0.14794 0.21167 0.26161 0.23996 0.20299 0.08496

0.13721 0.24782 0.20605 0.17439 0.14155 0.08802

0.12548 0.18939 0.19894 0.17463 0.11475 0.08223

0.12514 0.19125 0.15359 0.16662 0.13768 0.06278

0.10576 0.18499 0.20630 0.18364 0.18947 0.09188

α is the parameter related to the nonrandomness of the solution in NRTL model. 1350



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and ethanol, the eutectic compositions shift to 0.37. This may be attributed to the fact that the solvent−solute interaction remarkably influences the solute−solute interaction when the polarity of solvent exceeds a certain threshold. The shift of eutectic composition may be helpful for a better separation of ANTH and DBF. Figure 6 represents an

Article

AUTHOR INFORMATION

Corresponding Author

*Tel: +86-22-27405754. Fax: +86-22-27374971. E-mail: [email protected]. Funding

This research is financially supported by National Natural Science Foundation of China (No. 21376165), Specialized Research Fund for the Doctoral Program of Higher Education (Grant No.: SRFDP-20110032120016), and Key Project of Tianjin Science and Technology Supporting Programme (No. 13ZCZDNC02000). Notes

The authors declare no competing financial interest.

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Figure 6. Schematic diagram of separation of ANTH and DBF in the ternary system.

evaporative crystallization for a ternary system from the starting point of O. Pure ANTH will crystallize from the solution while the solution composition will locate at point Q. The point Q will move toward the eutectic point (E) during the elimination of the solvent from the solution via evaporation. Once the point Q reaches the eutectic point, DBF will appear, before which the separation should be stopped. If the eutectic point shifts toward DBF (for example to point É), it will provide more operating space and achieve a more efficient separation of ANTH and DBF.

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CONCLUSIONS The ternary SLE data for an ANTH−DBF mixture in a series of alcohols, including methanol, ethanol, propan-2-ol, propan-1-ol, butan-1-ol, and pentan-1-ol were determined by using a dynamic method. All the ternary mixtures investigated in this work form simple eutectic systems. The solubility order in these alcohols is pentan-1-ol > butan-1-ol > propan-1-ol > propan-2-ol > ethanol > methanol, which basically follows the relative polarity of the solvents. In comparison to the UNIQUAC and NRTL model, the Wilson model can give a better prediction of the SLE data with 6% APD. The pseudobinary system in combination with the Wilson model can provide a better estimation of the ternary SLE data with the APDs ranging from 0.7% to 4.0%. Besides the solubility, the eutectic composition is also affected by the solvent. The shift of the eutectic point toward DBF is attributed to the high polarity of the solvents. This shift could be used to help design a more efficient evaporative crystallization process of ANTH and DBF from the wash oil.

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ASSOCIATED CONTENT

S Supporting Information *

Additional tables and figures as described in the text. This material is available free of charge via the Internet at http:// pubs.acs.org. 1351



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SolidâLiquid Phase Equilibria of Ternary Mixtures Containing 1,2

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