Solid–Liquid Equilibria for Six Binary Mixtures of Pentanedioic Acid

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Solid−Liquid Equilibria for Six Binary Mixtures of Pentanedioic Acid, Octanedioic Acid, 3‑Methylheptanedioic Acid, 2,2-Dimethylbutanedioic Acid, and 2,3-Dimethylbutanedioic Acid Tzu-Chi Wang* and Chia-Hao Chang Department of Chemical and Materials Engineering and Master Program of Nanomaterials, Chinese Culture University, Taipei, Taiwan, ROC ABSTRACT: Solid−liquid equilibria for six organic binary mixtures, namely, pentanedioic acid (1) + 3-methylheptanedioic acid (3) (eutectic temperature TE = 329.94 K, eutectic composition x1E = 0.497); pentanedioic acid (1) + 2,2-dimethylbutanedioic acid (4) (TE = 354.07 K, x1E = 0.740); pentanedioic acid (1) + 2,3-dimethylbutanedioic acid (5) (TE = 338.95 K, x1E = 0.415); octanedioic acid (2) + 3-methylheptanedioic acid (3) (TE = 352.54 K, x1E = 0.144); octanedioic acid (2) + 2,2-dimethylbutanedioic acid (4) (TE = 386.49 K, x1E = 0.416); and octanedioic acid (2) + 2,3-dimethylbutanedioic acid (5) (TE = 368.30 K, x1E = 0.193, are measured in this study using differential scanning calorimetry. Simple eutectic behaviors for these systems are observed. The experimental results are correlated using the Wilson and nonrandom two-liquid activity coefficient models, and satisfactory results are presented.

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INTRODUCTION In the world of unit operation, there are various kinds of combinations of compounds and conditions. To tackle the ensuing problems, suitable methods must be applied to obtain viable solutions. In industrial applications in which a crystallization operation at relatively low temperatures occurs, such as the separation of isomeric or thermolabile compounds, the traditional distillation approach has its limits. This is where solid−liquid equilibrium (SLE) measurements prevail. The SLE data of various systems therefore are required for the development of separation processes. The motivation of this study is to fill the gap of experimental data that are not available in previous literature. Besides the traditional methods of either the cooling curve or visual measurement1 used to obtain SLE data, an alternative approach has been developed. The differential scanning calorimeter (DSC), a device that records the heat effect occurring in the phase transformation, provides researchers a time-saving tool with more accurate results. With the measurement of peak temperatures and heats of phase transformation, phase boundaries of SLE are determined.2 When the DSC method is applied, experimental SLE data on metal, polymer, and organic compound systems have been reported in literature.3−7 Furthermore, mathematical models for correlating the SLE results from DSC experiments have also been presented in the literature.5,8−10 This study is dedicated to, using DSC method, the measurement of novel SLE data of six binary organic mixtures: pentanedioic acid (C5H8O4) + 3-methylheptanedioic acid (C6H10O4); pentanedioic acid + 2,2-dimethylbutanedioic acid (C6H10O4); pentanedioic acid + 2,3-dimethylbutanedioic acid © 2013 American Chemical Society

(C6H10O4); octanedioic acid (C7H6O2) + 3-methylheptanedioic acid; octanedioic acid + 2,2-dimethylbutanedioic acid; and octanedioic acid + 2,3-dimethylbutanedioic acid. The Wilson11 and nonrandom two-liquid (NRTL)12 activity coefficient models are employed in correlating the experimental data. The eutectic temperatures and compositions from model correlation for all six binary mixtures are finally demonstrated to be in good agreement with the ones obtained from experimental observations.

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EXPERIMENTAL SECTION In the preparation of these mixtures, considerable caution is exercised. Octanedioic acid, pentanedioic acid, 3-methylheptanedioic acid, 2,2-dimethylbutanedioic acid, and 2,3-dimethylbutanedioic acid are bought from Aldrich. These chemicals are applied in the state of their purchase with no further purification for the purpose of consistencyusually having a purity greater than mass fraction w = 0.99. The melting temperatures and the enthalpies of fusion of these compounds are taken in this study employing the DSC (Perkin-Elmer DSC 4000). These measured pure component properties are compared with literature data, and the results are listed in Table 1. Satisfactory agreement on the first two pure fluids properties are observed where literature data are available. To achieve the final goal without any miss, every step of the experiment is taken with meticulous care. For each binary Received: July 29, 2013 Accepted: September 20, 2013 Published: October 22, 2013 3233

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Table 1. Comparison of the Measured Melting Temperatures and Heats of Fusion with Literature Data for Pure Compounds ΔfusHom/kJ·mol−1

Tm/K compound

source

pentanedioic acid 3-methylpetanedioic acid 2,2- dimethylbutanedioic acid 2,3-dimethylbutanedioic acid octanedioic acid

purity (mass fraction)

Aldrich Aldrich Aldrich Aldrich Aldrich

this study

0.99 0.99 0.99 0.99 0.99

literature 20

369.1 358.6 413.0 392.5 414.4

370.1 358.621 413.021 392.521 416.218

this study

literature

± ± ± ± ±

20.9019 28.9821 38.1121 16.9021 29.1619

21.53 28.98 38.11 16.90 30.52

0.13 0.04 0.07 0.21 0.5

Table 2. Measured Solid−Liquid Equilibrium Data for Three Binary Systems 100 x1 0.00 4.95 9.86 15.05 20.57 25.36 30.31 35.27 64.74 69.81 0.00 4.17 9.86 14.91 20.11 25.36 30.19 35.18 40.12 44.95 0.00 5.54 10.16 14.56 20.39 24.51 30.82 59.52 65.14 0.00 2.11 a

TE/K

TL/K

100 x1

TE/K

100 x1

TL/K

Pentanedioic Acid (1) + 3-Methylheptanedioic Acid (3) N/A 358.61 74.64 324.31 351.64 328.42 356.78 79.53 333.51 356.39 331.46 354.58 85.54 327.42 358.78 331.17 351.39 89.95 328.86 362.15 331.89 348.91 94.43 328.04 364.56 331.67 346.99 100.00 N/A 369.13 331.78 344.61 333.40 340.60 330.45 343.69 332.17 347.99 Pentanedioic Acid (1) + 2,2-Dimethylbutanedioic Acid (4) N/A 412.95 50.13 352.34 379.27 351.34 408.03 55.08 351.51 375.28 351.35 404.30 59.88 351.44 369.58 351.51 402.03 64.74 353.69 362.87 351.82 399.24 69.94 351.94 360.65 352.79 396.58 85.05 352.27 359.35 353.46 393.01 89.95 350.64 362.02 351.61 390.44 95.19 346.63 365.34 350.86 386.21 100.00 N/A 369.13 352.20 383.50 Pentanedioic Acid (1) + 2,3-Dimethylbutanedioic Acid (5) N/A 392.48 69.75 336.72 351.45 327.75 385.78 75.28 340.59 352.85 338.64 381.81 79.92 338.10 356.63 336.19 378.35 84.84 336.27 358.98 338.13 374.60 89.47 339.83 361.63 341.70 366.84 94.88 340.17 365.60 337.97 358.14 100.00 N/A 369.13 336.98 346.85 338.55 349.94 Octanedioic Acid (2) + 3-Methylheptanedioic Acid (3) N/A 358.61 54.95 350.93 390.78 348.45 357.54 59.96 350.04 393.47

4.88 8.09 20.04 24.96 29.86 34.91 40.00 44.88 50.01 0.00 5.28 10.05 15.33 19.86 24.99 29.86 34.73 60.03 65.12 0.00 5.08 9.85 15.29 30.02 34.67 39.97 45.00 50.12 55.05

TE/K

TL/K

100 x1

TE/K

Octanedioic Acid (2) + 3-Methylheptanedioic Acid (3) 349.60 356.26 65.12 351.19 350.00 354.89 69.87 348.67 350.61 361.96 75.11 350.65 350.69 365.86 80.10 347.57 350.72 369.05 85.13 349.46 351.32 373.92 90.10 346.91 351.07 380.96 94.97 345.19 351.37 384.27 100.00 N/A 350.56 388.00 Octanedioic Acid (2) + 2,2-Dimethylbutanedioic Acid (4) N/A 412.95 69.87 384.41 382.92 407.22 75.27 384.15 385.09 405.06 80.05 382.81 384.77 401.62 84.88 384.69 384.63 397.81 89.77 385.72 383.94 395.20 95.26 382.49 384.12 392.95 100.00 N/A 385.44 388.80 384.73 393.84 384.66 396.19 Octanedioic Acid (2) + 2,3-Dimethylbutanedioic Acid (5) N/A 392.48 60.20 370.29 369.53 384.96 65.21 371.41 367.37 380.85 70.07 372.04 368.37 377.37 74.90 368.93 369.95 375.43 79.92 371.41 372.39 381.91 84.64 371.82 371.06 384.26 90.03 370.61 370.04 384.93 94.99 367.53 369.40 388.92 100.00 N/A 370.75 389.47

TL/K 395.20 397.65 400.41 404.74 406.75 409.16 411.65 414.44

397.77 400.54 401.09 405.69 409.28 413.48 414.44

393.79 394.71 397.41 402.36 403.86 405.65 409.05 411.38 414.44

NA: not available.

heavier (molecular weight) component in the binary mixture. The sample is then kept at this temperature for 1 min before cooling at a rate of 10 K·min−1, to 303.15 K. The sample stays at this temperature for 30 min to finish the pretreatment procedure. Samples for pentanedioic acid (1) + 2,3dimethylbutanedioic acid (5), octanedioic acid (2) + 3-methylheptanedioic acid (3), and octanedioic acid (2) + 2,3-dimethylbutanedioic acid (5) are heated at the rate of 1 K·min−1. However, samples of pentanedioic acid (1) + 3-methylheptanedioic acid (3), pentanedioic acid (1) + 2,2-dimethylbutanedioic acid (4), and octanedioic acid (2) + 2,2-dimethylbutanedioic acid (4) are heated at a slower rate of 0.5 K·min−1 or

mixture, a 4 mg sample of a specific weight composition is kept in a high-pressure airtight aluminum container purchased from Perkin-Elmer. The balance (Shimadzu C9AS-AUW220D) used in this experiment has an accuracy of ± 0.01 mg. To clean the devices, the DSC is infused with nitrogen gas first and then heated to 673.2 K. Before its application in the SLE measurements, the DSC is calibrated with high-purity indium and zinc. To prevent the thermal histories of the previous use interfering with the accuracy of the experiment and to homogenize the sample mixture, each mixture undergoes a first-stage heating. With a heating rate of 10 K·min−1, the mixture is heated to a temperature above the melting temperature of the 3234

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Table 3. Optimally Fitted Binary Parameters and the Deviations of Regression form the Wilson and NRTL Models Wilson parametersa

NRTL parameter (α12 is 0.3 in this study)

AADTb/%

system

[(λ12 − λ11)/R]/K, [(λ21 − λ22)/R]/K

[(g12 − g22)/R]/K, [(g21 − g11)/R]/K

Wilson NRTL

pentanedioic acid (1) + 3-methylheptanedioic acid (3) pentanedioic acid (1) + 2,2-dimethylbutanedioic acid (4) pentanedioic acid (1) + 2,3-dimethylbutanedioic acid (5) octanedioic acid (2) + 3-methylheptanedioic acid (3) octanedioic acid (2) + 2,2-dimethylbutanedioic acid (4) octanedioic acid (2) + 2,3-dimethylbutanedioic acid (5)

27.59/-259.73 468.01/-515.71 −151.51/278.22 199.64/1.8282 486.78/-500.30 304.3/37.19

−600.73/717.25 1096.2/-778.7 −360.15/308.78 5.5/3498.5 −760.44/580.60 −160.56/510.83

0.14 0.27 0.43 0.22 0.4 0.39

0.14 0.42 0.41 0.38 0.49 0.38

0.25522

Liquid molar volumes: V/((m3)/(kmol)), T/K. V = ((0.245421+(1−T/807) )/(0.67612)) for pentanedioic acid (1); V = 0.11186 + 0.00013872 × T for octanedioic acid (2); V = 0.087037 + 0.00011062 × T for 3-methylheptanedioic Acid (3); V = 0.088476 + 0.00010552 × T for 2,2-dimethylbutanedioic Acid (4); V = 0.087254 + 0.0001084 × T for 2,3-dimethylbutanedioic acid (5). bAADT = 100/N∑kN= 1|((TL(calc) − TL(expt))/(TL(expt)))|. a

1 K·min−1 in order to clearly identify the peaks in the DSC curves. The eutectic temperatures and the liquidus temperatures are taken as the onset temperatures and the modified peak temperatures, respectively, from the DSC measurements, as is illustrated in our previous study.6 Repeated runs are conducted to confirm the reproducibility of experimental results. The uncertainty for temperature measurement is about ± 1 K. The maximum uncertainties for some experimental liquidus and solidus temperatures are 3−5 K. Reproducibility of our experimental results was justified by repeated experiments for each sample mixture.

Table 4. Comparison of the Eutectic Point Results from Different Methods for Three Binary Mixtures

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MODEL AND CORRELATION In this study, the thermodynamic relationship for SLE is obtained by using the equal fugacity criterion.13 Assuming that the difference between the heat capacities of the liquid and that of the solid is negligible, we have: ln(γix i) = −

o ⎛T ⎞ ΔfusHmi m,i − 1⎟ ⎜ ⎠ RTm,i ⎝ T

(1)

ΔfusHom

where the constant γ deontes the activity coefficient; is the molar enthalpy of fusion; Tm is the melting temperature; and x is the equilibrium liquid composition in mole fraction. In eq 1, the value γ, the activity coefficient, is representative of the nonideal solution behavior. This value is correlated by the Wilson and NRTL models. The Wilson model is expressed as ⎛ ⎞ Λ12 Λ 21 ln γ1 = − ln(x1 + Λ12x 2) + x 2⎜ − ⎟ Λ 21x1 + x 2 ⎠ ⎝ x1 + Λ12x 2

⎞ ⎛ Λ12 Λ 21 ln γ2 = − ln(x 2 + Λ 21x1) − x1⎜ − ⎟ Λ 21x1 + x 2 ⎠ ⎝ x1 + Λ12x 2

⎤ ⎞2 ⎛ G12 τ21G21 ⎥ ln γ2 = x1 τ12⎜ ⎟ + 2 ⎢⎣ ⎝ x 2 + x1G12 ⎠ (x1+x 2G21) ⎥⎦

(7)

ln G12 = −α12τ12

(8)

⎡

2⎢

(3)

(4)

⎛ λ − λ 22 ⎞ V ⎟ Λ 21 = 1 exp⎜ − 21 ⎝ V2 RT ⎠

(5)

τ12 =

where R is the gas constant, and V1 and V2 are the liquid molar volumes, which are determined by DIPPR14 or Elbro’s group contribution method.15 The two adjustable parameters are (λ12 − λ11)/R and (λ21 − λ22)/R. The NRTL equations are presented as ⎤ ⎡ ⎛ ⎞2 G21 τ12G12 ⎥ ln γ1 = x 2 2⎢τ21⎜ ⎟ + ⎢⎣ ⎝ x1 + x 2G21 ⎠ (x 2+x1G12)2 ⎥⎦

TE/K

(2)

⎛ λ − λ11 ⎞ V2 ⎟ exp⎜ − 12 ⎝ V1 RT ⎠

Λ12 =

eutectic composition, x1

method

Pentanedioic Acid (1) + 3-Methylheptanedioic Acid (3) Wilson model 0.508 328.52 NRTL model 0.506 328.38 Clarke−Glew equation 0.497 329.94 Pentanedioic Acid (1) + 2,2-Dimethylbutanedioic Acid (4) Wilson model 0.746 352.78 NRTL model 0.737 348.58 Clarke−Glew equation 0.740 354.07 Pentanedioic Acid (1) + 2,3-Dimethylbutanedioic Acid (5) Wilson model 0.518 337.89 NRTL model 0.501 331.12 Clarke−Glew equation 0.437 340.08 Octanedioic Acid (2) + 3-Methylheptanedioic Acid (3) Wilson model 0.159 353.33 NRTL model 0.105 363.38 Clarke−Glew equation 0.144 352.54 Octanedioic Acid (2) + 2,2-Dimethylbutanedioic Acid (4) Wilson model 0.486 376.66 NRTL model 0.492 374.16 Clarke−Glew equation 0.416 386.49 Octanedioic Acid (2) + 2,3-Dimethylbutanedioic Acid (5) Wilson model 0.271 372.93 NRTL model 0.271 372.91 Clarke−Glew equation 0.193 368.30

g12 − g22 RT

ln G21 = −α12τ21

τ21 =

g21 − g11 RT

(9)

where (g12 − g22)/R and (g21 − g11)/R are adjustable parameters which are independent of composition and temperature. On the one hand, α12, the nonrandomness factor of the NRTL model is set to be 0.3. On the other hand, the adjustable parameters for each binary mixture, whether in the Wilson model or the NRTL model, are calculated with the minimization of the following objective function (obj), which is the mean sum of the ratio of the

(6) 3235

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Figure 1. Comparison of the experimental and calculated liquidus temperature for the binary mixture of pentanedioic acid (1) + 3-dethylheptanedioic acid (3) (●, liquidus temperature; ▲, eutectic temperature; ---, Wilson model; , Clarke−Glew equation).

Figure 2. Comparison of the experimental and calculated liquidus temperature for the binary mixture of pentanedioic acid (1) + 2,2-dimethylbutanedioic acid (4) (●, liquidus temperature; ▲, eutectic temperature; ---, Wilson model; , Clarke−Glew equation).

Figure 3. Comparison of the experimental and calculated liquidus temperature for the binary mixture of pentanedioic acid (1) + 2,3-dimethylbutanedioic acid (5) (●, liquidus temperature; ▲, eutectic temperature; ---, Wilson model; , Clarke−Glew equation). 3236

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Figure 4. Comparison of the experimental and calculated liquidus temperature for the binary mixture of octanedioic acid (2) + 3-methylheptanedioic acid (3) (●, liquidus temperature; ▲, eutectic temperature; ---, Wilson model; , Clarke−Glew equation).

Figure 5. Comparison of the experimental and calculated liquidus temperature for the binary mixture of octanedioic acid (2) + 2,2-dimethylbutanedioic acid (4) (●, liquidus temperature; ▲, eutectic temperature; ---, Wilson model; , Clarke−Glew equation).

The best-fitted parameters of the Wilson and NRTL models are then evaluated from liquidus data points. It is demonstrated that satisfactory experimental data can be obtained under the assignment of optimal binary parameters (shown in Table 3) to either the Wilson or the NRTL model. Also shown in Table 3 are the absolute average deviations (AADT) in the calculated liquidus temperatures. The AADT values fall within the ranges of experimental uncertainty for all six binary mixtures. The absolute average deviations of both the activity coefficient models are nearly the same, all less than 0.46 % of liquidus temperatures. For the six binary mixtures of this research, Table 4 displays the eutectic compositions and temperatures. From the table it can be observed that the data calculated and the data measured are in satisfactory agreement. The numbers listed in this table are the results gleaned by using the Clarke−Glew equation,16,17 the Wilson model, or the NRTL model. The Clarke−Glew equation is a general-purpose regression equation widely used in the field of thermodynamics to find an appropriate fitting curve for measured data.

difference between the calculated and experimentally determined liquidus temperatures TL: N

obj =

⎛ 1 ⎞⎧ TL(calc) − TL(expt) ⎫ ⎟⎨ ⎬ N ⎠⎩ TL(expt) ⎭

∑ ⎜⎝ k=1

k

(10)

The subscript k denotes the kth data point. After the assignment of these optimal parameters the SLE phase boundaries can be in turn determined with these models. The data and corresponding comparison between the experimentally measured and calculated results are presented in the next sections.

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RESULTS AND DISCUSSION Table 2 shows the measured temperaturesthe eutectic temperatures (TE) and the liquidus temperatures (TL)of all the combination of the six binary mixtures at various compositions (mole fractions). The uncertainties of the measurement for both the experimentally determined temperatures and compositions are estimated as ± 1 K (with the maximum uncertainty of 3−5 K) and ± 0.002 mol fraction, respectively. 3237

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Figure 6. Comparison of the experimental and calculated liquidus temperature for the binary mixture of octanedioic acid (2) + 2,3-dimethylbutanedioic acid (5) (●, liquidus temperature; ▲, eutectic temperature; ---, Wilson model; , Clarke−Glew equation).

Notes

The calculated phase boundaries for the six binary systems pentanedioic acid (1) + 3-methylheptanedioic acid (3); pentanedioic acid (1) + 2,2-dimethylbutanedioic acid (4); pentanedioic acid (1) + 2,3-dimethylbutanedioic acid (5); octanedioic acid (2) + 3-methylheptanedioic acid (3); octanedioic acid (2) + 2,2-dimethylbutanedioic acid (4); and octanedioic acid (2) + 2,3-dimethylbutanedioic acid (5) are illustrated in Figures 1 to 6 with their graphical presentations, respectively. The eutectic composition and temperature for pentanedioic acid (1) + 3-methylheptanedioic acid (3) are determined as x1E = 0.497 and TE = 329.94 K; for pentanedioic acid (1) + 2,2-dimethylbutanedioic acid (4), x1E = 0.740 and TE = 354.07 K; for pentanedioic acid (1) + 2,3-dimethylbutanedioic acid (5), x1E = 0.437 and TE = 340.08 K; for octanedioic acid (2) + 3-methylheptanedioic acid (3), x1E = 0.144 and TE = 352.54 K; for octanedioic acid (2) + 2,2-dimethylbutanedioic acid (4), x1E = 0.416 and TE = 386.49 K; and for octanedioic acid (2) + 2,3dimethylbutanedioic acid (5), x1E = 0.193 and TE = 368.30 K.

The authors declare no competing financial interest.

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CONCLUSION The solid−liquid equilibrium (SLE) measurements of various mixtures are indispensable in theoretical research and practical applications alike when these mixtures occur in the process. This study measures the solid−liquid equilibrium for six binary mixtures of organic dicarboxylic acids by using DSC. All these binary systems show simple eutectic behavior. The measured liquidus temperatures are applied to the calculation of data correlation in both the Wilson and the NRTL activity coefficient models. Satisfactory correlation results are obtained for both models, and their optimally fitted binary parameters are reported. The measured liquidus results are also applied to find the fitting curve of the Clarke−Glew equation. It is also observed that the smoothing data and the eutectic results derived from both models are in satisfactory agreement. Novel eutectic composition and temperature data are finally presented for six binary systems. The differences in their eutectic temperatures and compositions are consistent with the trend of the melting temperatures of pure components.

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REFERENCES

(1) Wittig, R.; Constantinescu, D.; Gmehling, J. Binary Solid−Liquid Equilibria of Organic Systems Containing ε-Caprolactone. J. Chem. Eng. Data 2001, 46, 1490−1493. (2) Hammani, A.; Mehrotra, A. K. Nonisothermal Crystallization Kinetics of n-Paraffins with Chain Lengths between Thirty and Fifty. Thermochimica 1992, 211, 137−153. (3) Flotter, E.; Hollander, B.; de Loos, T. W.; de Swaan Arons, J. Ternary System (n-Heptane + Docosane + Tetracosane): The Solubility of Mixtures of Docosane in Heptane and Data on Solid− Liquid and Solid−Solid Equilibria in the Binary System (Docosane + Tetracosane). J. Chem. Eng. Data 1997, 42, 562−565. (4) Takiyama, H.; Suzuki, H.; Uchida, H.; Matsuoka, M. Determination of Solid−Liquid Phase Equilibria by Using Measured DSC Curves. Fluid Phase Equilib. 2002, 194−197, 1107−1117. (5) Huang, C. C.; Chen, Y. P. Measurements and Model Prediction of the Solid−Liquid Equilibria of Organic Binary Mixtures. Chem. Eng. Sci. 2000, 55, 3175−3185. (6) Chen, Y. P.; Tang, M.; Kuo, J. C. Solid−Liquid Equilibria for Binary Mixtures of N-Phenylacetamide with 4-Aminoacetopheneone, 3-Hydroxyacetophenone and 4-Hydorxyacetophenone. Fluid Phase Equilib. 2005, 232, 182−188. (7) Zhou, C.; Shi, X.; Chen, L.; Wang, H. The Measurement of Solid−Liquid Equilibrium Data of Binary and Ternary Organic Systems for Imidacloprid + 2-Nitroaminoimidazoline + NMP by DSC. Fluid Phase Equilib. 2011, 302, 123−126. (8) Matsuoka, M.; Ozawa, R. Determination of Solid−Liquid-Phase Equilibria of Binary Organic Systems by Differential Scanning Calorimetry. J. Cryst. Growth 1989, 96, 596−604. (9) Wang, T. C.; Lai, T. Y.; Chen, Y. P. Solid−Liquid Equilibria for Hexanedioic Acid + Benzoic Acid, Benzoic Acid + Pentanedioic Acid, and Hexanedioic Acid + Pentanedioic Acid. J. Chem. Eng. Data 2010, 55, 5797−5800. (10) Wang, T. C.; Deng, K. G. Solid−Liquid Equilibria for Three Binary Mixtures of Benzoic Acid with Heptanedioic Acid, 3Methylpentanedioic Acid, and 2,3-Dimethylbutanedioic Acid. J. Chem. Eng. Data 2012, 57, 78−81. (11) Wilson, G. M. Vapor−Liquid Equilibrium. XI: A New Expression for the Excess Free Energy of Mixing. J. Am. Chem. Soc. 1964, 86, 127−130. (12) Renon, H.; Prausnitz, J. M. Local Compositions in Thermodynaic Excess Functions for Liquid Mixtures. AIChE J. 1968, 14, 135−144.

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Fax: +886-2-2861-4011. 3238

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(13) Prausnitz, J. M.; Lichtenthaler, R. N.; Azevedo, E. G. A. Molecular Thermodynamics of Fluid-Phase Equilibria; Prentice Hall: NY, 1999. (14) Rowley, R. L.; Wilding, W. V.; Oscarson, J. L.; Yang, Y.; Zundel, N. A.; Daubert, T. E.; Danner, R. P. DIPPR Data Compilation of Pure Compound Properties; Design Institute for Physical Properties, AIChE: New York, 2003. (15) Ihmels, E. C.; Gmehling, J. Extension and Revision of the Group Contribution Method GCVOL for the Prediction of Pure Compound Liquid Densities. Ind. Eng. Chem. Res. 2003, 42, 408−412. (16) Hefter, G. T.; Tomkins, R. P. T. Experimental Determination of Solubilities. John Wiley & Sons: Chichester, UK, 2003. (17) Gamsjäger, H.; Lorimer, J. W.; Salomon, M.; Shaw, D. G.; Tomkins, R. P. T. The IUPAC-NIST Solubility Data Series: A Guide to Preparation and Use of Compilations and Evaluations. J. Phys. Chem. Ref. Data 2010, 39 (2), 023101. (18) Cingolani, A.; Berchiesi, G. Thermodynamic Properties of Organic Compounds. Note 1. A DSC Study of Phase Transitions in Aliphatic Dicarboxylic Acids. J. Therm. Anal. 1974, 6, 87. (19) Wilhoit, R. C.; Shiao, D. Thermochemistry of Biologically Important Compounds. Heats of Combustion of Solid Organic Acids. J. Chem. Eng. Data 1964, 9, 595. (20) Othmer, K. Encyclopedia of Chemical Technology; Inter-Science: NY, 1978. (21) Wang, T. C.; Li, Y. J.; Chen, Y. P. Solid−Liquid Equilibria for Six Binary Mixtures Involving Heptanedioic Acid, Pentanedioic Acid, Hexanedioic Acid, 2,3-Dimethylbutanedioic Acid, 2,2-Dimethylbutanedioic Acid, and 3-Methylheptanedioic Acid. J. Chem. Eng. Data 2012, 57, 3519−3524.

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