Measurements and Comparative Study of Ternary Liquid–Liquid

Article pubs.acs.org/jced

Measurements and Comparative Study of Ternary Liquid−Liquid Equilibria for Water + Acrylic Acid + Cyclopentyl Methyl Ether at (293.15, 303.15, and 313.15) K and 100.249 kPa Hongxun Zhang* School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou, Henan 450001, China ABSTRACT: Extraction followed by heterogeneous azeotropic distillation is an effective and energy-saving method to separate acrylic acid from aqueous solution. In this work, the liquid−liquid equilibria data for the system of water + acrylic acid + cyclopentyl methyl ether at three temperatures were determined at 100.249 kPa. The reliability of the liquid− liquid equilibria data was ascertained by using Hand and Othmer−Tobias correlations. The separation factors of cyclopentyl methyl ether at different temperatures were compared. NRTL and UNIQUAC models were used to correlate the liquid−liquid equilibria experimental data. Moreover, a comparative study on the three solvents, including cyclopentyl methyl ether, isobutyl ethanoate, and 4-methyl-2-pentanone, was made in terms of basic physical properties and extraction ability.

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INTRODUCTION Acrylic acid (or prop-2-enoic acid) is an important chemical intermediate used to produce a water treatment agent, phosphorus-free detergent, superabsorbent resin, and specialty or general purpose acrylate. There will be an increased demand for acrylic acid (AA) with the increasing regard for environment protection.1,2 In our previous work, we have introduced the production of AA.3−9 The typical method for producing AA is gas-phase catalytic oxidation of propylene.8 In this case, a crude aqueous AA is obtained when the gas produced by the oxidation reaction is cooled and absorbed in water. The crude aqueous acrylic acid is then subjected to purification including at least dehydration, thereby obtaining acrylic acid with high purity. The azeotropic distillation method is widely used to purify acrylic acid at present. However, the energy consumption of azeotropic distillation acid is very high because water in the crude aqueous phase of AA must to be distilled from the top of the column with an entrainer such as isobutyl ethanoate (IBE) or 4-methyl-2-pentanone (MIBK). Extraction followed by heterogeneous azeotropic distillation was considered to be an effective, energy-saving method to separate acrylic acid from crude aqueous acrylic acid.10−15 The most important requirement for this method is a suitable solvent. Cyclopentyl methyl ether (CPME) is an excellent solvent which can be used as not only extractant but also entrainer because of it has high hydrophobicity, is relatively stable under acidic and alkaline conditions, and has a low latent heat of evaporation and narrow explosion range.16−20 However, there is no report about the liquid−liquid equilibrium (LLE) of the ternary system water + acrylic acid + CPME. In this work, the LLE data of water + acrylic acid + CPME at (293.15, 303.15, and 313.15) K were determined at 100.249 © XXXX American Chemical Society

kPa. The experimental data were modeled by NRTL and UNIQUAC activity-coefficient models. In addition, comparative study between this work and our previous work was demonstrated.3,4 CMPE was compared with IBE and MIBK in terms of physical properties and extraction ability.

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EXPERIMENT SECTION Chemicals. Double-distilled water was prepared in our laboratory. The electrical conductivity of the fresh distilled water was measured using a conductivity meter (sensION+, HACH) at 293.15 K, and the value was 0.0001 S·m−1. CPME with a mass percent of 99.9 % was purchased from Alfa Aesar Inc. AA was purchased from the Sinopharm Chemical Reagent Co., Ltd. with a minimum mass percent purity of 99.5 %. All of the chemicals mentioned above were checked with chromatographic analysis and used without further purification. The densities and refractive indexes of the pure chemicals were measured at 293.15 K using a DE-120W densimeter and a WYA-2S Abbe refractometer, respectively. The uncertainties of density and refractive index are ±0.1 kg·m−3 and 0.0001, respectively. The experimental values of purity, density, and refractive index are listed in Table 1 together with those reported in the literature21 or stated by supplier. Apparatus and Procedure. The LLE data of water + acrylic acid + CPME were measured by using a jacketed glass cell, a magnetic agitator, and a thermostatically controlled bath (501A type, Shanghai, China) at atmospheric pressure. The atmospheric pressure is about 100.249 kPa at Zhengzhou city. Received: November 29, 2014 Accepted: March 25, 2015

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Table 1. Purities, Densities, Refractive Indexes, and UNIQUAC Structure Parameters of Chemicals Used in This Work

chemical name

ρ(T = 293.15 K) kg·m−3

minimum purity

water acrylic acid CPME a

purity mass percent a

nD(T = 293.15 K) b

GC analysis

exptl

lit.

99.95 99.75 99.95

998.25 1051.22 860.43

998.20 1051.10 860.00

99.5 99.9

UNIQUAC parameters

b

exptl

lit.

1.3334 1.4223 1.4187

1.3334 1.4224 1.4189

ri

qi

0.9200 2.6467 4.2142

1.4000 2.4000 3.2480

Stated by supplier. bTaken from Lange’s Handbook of Chemistry.

Table 2. Experimental LLE Data (Mass Fraction w), Distribution Ratio (D1, D2) and Separation Factor (S) for the Water (1) + Acrylic Acid (2) + CPME (3) System at (293.15, 303.15, and 313.15) K and 100.249 kPaa solvent-rich phase

water-rich phase w2I

w1

0.0086 0.0237 0.0486 0.0671 0.0806 0.1025 0.1188 0.1551 0.1983

0.0000 0.1510 0.2295 0.2952 0.3283 0.3571 0.3849 0.4211 0.4418

0.0102 0.0365 0.0668 0.0836 0.0986 0.1216 0.1456 0.1689 0.1979

0.0156 0.0412 0.0745 0.0889 0.1069 0.1342 0.1596 0.1813 0.2152

w1

I

II

w2II

D1

D2

S

0.9889 0.9475 0.9173 0.8803 0.8546 0.8224 0.7753 0.7513 0.7172

0.0000 0.0234 0.0480 0.0864 0.1066 0.1306 0.1683 0.1882 0.2109

0.0250 0.0530 0.0762 0.0943 0.1246 0.1532 0.2064 0.2765

6.4530 4.7813 3.4167 3.0797 2.7343 2.2870 2.2375 2.0948

257.9835 90.2436 44.8240 32.6544 21.9384 14.9251 10.8385 7.5765 60.1230

0.0000 0.1649 0.2453 0.2858 0.3192 0.3608 0.3806 0.4002 0.4241

0.9832 0.9295 0.8976 0.8727 0.8395 0.7898 0.7578 0.7365 0.7038

0.0000 0.0396 0.0698 0.0918 0.1175 0.1591 0.1815 0.1995 0.2211

0.0393 0.0744 0.0958 0.1175 0.1540 0.1921 0.2293 0.2812

4.1641 3.5143 3.1133 2.7166 2.2678 2.0970 2.0060 1.9181

106.0430 47.2224 32.4996 23.1296 14.7292 10.9140 8.7474 6.8215 31.2634

0.0000 0.1621 0.2402 0.2838 0.3134 0.3557 0.3735 0.3924 0.4150

0.9808 0.9186 0.8818 0.8622 0.8255 0.7737 0.7422 0.7183 0.6856

0.0000 0.0457 0.0793 0.0976 0.1272 0.1697 0.1931 0.2121 0.2346

0.0449 0.0845 0.1031 0.1295 0.1735 0.2150 0.2524 0.3139

3.5470 3.0290 2.9078 2.4638 2.0961 1.9342 1.8501 1.7690

79.0853 35.8520 28.2013 19.0262 12.0843 8.9949 7.3299 5.6357 24.5262

T/K = 293.15

avg T/K = 303.15

avg T/K = 313.15

avg a

Standard uncertainties u are u(T) = 0.05 K, u(p) = 1.5 kPa, and u(w) = 0.005.

Considering the fluctuation of atmospheric pressure, the uncertainty of pressure was estimated to be within ± 1.5 kPa. The temperature uncertainty was ± 0.05 K. An electronic balance (AUY220, Shimadzu) with standard uncertainty of 0.0001 g was used to weigh the weights of the reagents investigated in this work. The specific experiment procedures were reported in the literature.16 Sample Analysis. A GC-122 series gas chromatograph equipped with a thermal conductivity detector (TCD) was used to determine the compositions of the samples. A 2 m × 3 mm inner diameter stainless steel column packed with a Porapak QS (80/100) was used for the chromatographic analysis. The

oven temperature of the gas chromatograph was 473.15 K, whereas the temperatures of injector and detector were both 493.15 K. Hydrogen was used as carrier gas and kept at 0.8 cm3· s−1. The bridge current of the TCD was 150 mA. The injection volume was kept constant at 0.2 mm3. The peak separations achieved under the chromatographic conditions were very good. The internal standard and correction factor methods were used to analyze the compositions of the samples. Isopropyl alcohol was used as internal standard. The analysis results from the correction factor method are identical with the ones from the internal standard method. The uncertainty in the mass fraction of the LLE data was usually within 0.005. B

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RESULT AND DISCUSSION Experimental LLE Data. Table 2 lists the LLE data, expressed in mass fraction, of the ternary system water + acrylic acid + CPME at (293.15, 303.15, and 313.15) K. The LLE phase diagram of the ternary system at three temperatures is shown in Figure 1.

Di =

S=

wiI wiII

(3)

D2 D1

(4)

Where, w represents mass fraction of water or acrylic acid; ditto for the superscript I and II. D1 and D2 represent the distribution coefficient of water and acrylic acid, respectively; and S represents the separation factor of CPME. The values of D1, D2, and S are listed in Table 1. The separation factor (S) of CPME versus the mass fraction of acrylic acid in the solvent-rich phase (wI2) at three temperatures is shown in Figure 2.

Figure 1. LLE phase diagram of water (1) + acrylic acid (2) + CPME (3) system at (293.15, 303.15, and 313.15) K and 100.249 kPa.

The Othmer−Tobias22 equation and Hand23 equation were used to examine the reliability of the experimental data. The equations are represented as follows: ⎛ 1 − wI ⎞ ⎛ 1 − w II ⎞ 3 1 ⎟ = a + b ln⎜ ⎟ ln⎜ I II w w ⎠ ⎝ ⎝ ⎠ 3 1

Figure 2. Separation factor (S) of CPME versus the mass fraction of acrylic acid in the CPME-rich phase (wI2) for water (1) + acrylic acid (2) + CPME (3) system at (293.15, 303.15, and 313.15) K and 100.249 kPa.

(1)

⎛ wI ⎞ ⎛ w II ⎞ ln⎜ 2I ⎟ = m + n ln⎜ 2II ⎟ ⎝ w1 ⎠ ⎝ w3 ⎠

Data Correlation. The NRTL and UNIQUAC models24−26 were used to correlate the LLE data investigated in this work. The adjustable parameter (τij) of those two models and the objective function of regression algorithm can be seen in the literature.3 Data regression for the water + acrylic acid + CPME system was carried out by Aspen Plus software (version 8.0). The interaction parameters, aij, in the NRTL model were set as zero. The pure component structural parameters (r, q) in the UNQUAC model were obtained from Aspen Plus database and listed in Table 1. The regressed interaction parameters and the root-mean-square deviations (rmsd) between experimental and calculated data are listed in Table 4. The rmsd is defined as

(2)

where the superscripts I and II represent solvent-rich phase and water-rich phase, respectively, and subscripts 1, 2, and 3 represent water, acrylic acid, and CPME, respectively. The letters a and b are parameters in the Othmer−Tobias equation, m and n in the Hand equation. The parameters at three temperatures of these two equations are listed in Table 3. From Table 3, it can be seen that the linear correlation coefficients (R2) are all not less than 0.9861. The standard deviations (SDs) are all not greater than 0.0821. Distribution coefficient and separation factor can be used to evaluate the extraction ability of the solvent. The distribution coefficient (D) and the separation factor (S) are calculated as follows:

⎛ n 2 3 ⎛ (w calcd − w exptl)2 ⎞⎞1/2 ijk ijk ⎟⎟ rmsd = ⎜∑ ∑ ∑ ⎜⎜ ⎟⎟ ⎜ 6 n ⎠⎠ ⎝k=1 j=1 i=1 ⎝

(5)

Table 3. Constants of the Othmer−Tobias and Hand Equations Othmer−Tobias T/K

a

b

293.15 303.15 313.15

1.4183 1.3274 1.3245

1.0129 1.0123 1.0708

R

Hand 2a

0.9878 0.9874 0.9873

a

SD

m

n

R2a

SDa

0.0821 0.0744 0.0756

0.9648 0.9780 0.9557

0.7276 0.8016 0.8379

0.9861 0.9938 0.9930

0.0789 0.0471 0.0508

a 2

R is linear correlation coefficient, SD is standard deviation. C

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Table 4. NRTL and UNIQUAC Parameters for the System Water (1) + Acrylic Acid (2) + CPME (3) at (293.15, 303.15, and 313.15) K and 100.249 kPa component

NRTL

UNIQUAC

T/K

i−j

bij/K

bji/K

αij

rmsd

aij

aji

bij/K

bji/K

rmsd

293.15

1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3

560.93 1251.65 −531.38 562.68 1360.59 −466.60 594.56 1384.56 −432.11

182.04 767.72 1291.29 204.43 703.28 1164.07 113.37 734.63 1347.72

0.457 0.315 0.470 0.457 0.315 0.470 0.457 0.315 0.470

0.0066

0.66 −10.00 28.37 0.40 −25.19 34.19 0.28 −31.68 33.09

−0.18 −12.48 32.83 −0.16 −8.95 29.32 −0.03 −7.16 27.64

−425.92 3025.86 −8144.58 −430.92 7715.10 −10000.00 −430.92 10000.00 −10000.00

140.83 −3658.54 −9749.43 200.83 −2713.72 −10000.00 180.83 −2099.28 −10000.00

0.0121

303.15

313.15

0.0056

0.0066

0.0072

0.0054

where wcalcd and wexptl ijk ijk are the calculated and the experimental mass fractions of component i in phase j on tie-line k, and n is the number of tie-lines, respectively. The experimental tie-line data of the ternary system water + acrylic acid + CPME at (293.15, 303.15, and 313.15) K are shown in Figures 3 to 5 together with calculated binodal curve using NRTL and UNIQUAC models.

Figure 4. Comparison between experimental LLE tie-lines data and calculated tie-lines using NRTL and UNIQUAC models for the ternary system water (1) + acrylic acid (2) + CPME (3) at 303.15 K.

Figure 3. Comparison between experimental LLE tie-lines data and calculated tie-lines using NRTL and UNIQUAC models for the ternary system water (1) + acrylic acid (2) + CPME (3) at 293.15 K.

Comparative Study. CMPE, IBE, and MIBK were compared in terms of physical properties and separating power. The LLE data of water + AA + solvent (IBE or MIBK) have been reported in our previous work.3,4 The basic physical properties of CPME, IBE, and MIBK are listed in Table 5.17,21,27−30 From Table 5, we can see that the boiling point, latent heat of vaporization, and azeotropic point with water of CPME are the lowest of the three solvents. Moreover, the mutual solubility with water of CPME is relatively small. Among the three solvents, CPME may have the greatest energy-saving potential when using extraction followed by heterogeneous azeotropic distillation to separate acrylic acid from water. The distribution coefficients of water (D1) in the three solvents and the separation factors (S) of three solvents at 293.15 K are compared in Figure 6 and Figure 7, respectively. It can be seen from Figure 6 that the distribution coefficients of

Figure 5. Comparison between experimental LLE tie-lines data and calculated tie-lines using NRTL and UNIQUAC models for the ternary system water (1) + acrylic acid (2) + CPME (3) at 313.15 K.

water in CPME at 293.15 K are obviously smaller than those in the other two solvents. This means that the water content is relatively low in the CPME-rich phase, and high in the waterD

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Table 5. Physical Properties of CPME, IBE, and MIBK property −3

density (293.15 K) [kg·m ] vapor specific gravity (air = 1) boiling point [K] viscosity (293.15 K) [cP] latent heat of vaporization (bp) [kJ·kg−1] azeotropic point with water [K] solubility in water [g/100 g] solubility of water in the solvent [g/100 g] a

CPMEa

IBEa

MIBKa

860 3.45 379.15 0.55 289.66 356.15b 1.1 (296.15 K) 0.3 (296.15 K)

871.2 4 391.15 0.697 308.8 360.6c 0.67 (293.15 K) 1.64 (293.15 K)

797.8 3.5 389.65 0.585 364.12 361.05d 1.7 (293.15 K) 1.9 (293.15 K)

Azeotrope (wt %). bComposition = CPME, 83.7; H2O,16.3. cComposition = IBE, 80.5; H2O, 19.5. dComposition = MIBK, 75.7; H2O, 24.3.

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CONCLUSIONS The LLE data of the water + acrylic acid + CPME system at (293.15, 303.15, and 313.15) K were determined at atmospheric pressure. The reliability of the LLE data was examined by using the Othmer−Tobias and Hand equations, respectively. The result shows the LLE data are reliable. The experimental LLE data were correlated by using NRTL and UNIQUAC models. All of the rmsds are not more than 0.0121. The separation factor of CPME decreases with increasing temperature. Therefore, it is beneficial to extract acrylic acid from water using CPME in a lower temperature. A comparative study on CPME, IBE, and MIBK indicates that CPME, as a solvent, has a lot of advantages such as low boiling point, low latent heat of vaporization, and low azeotropic point and mutual solubility with water. It can be concluded that CPME has a strong separation ability and great energy-saving potential in the process of extraction followed by heterogeneous azeotropic distillation to separate acrylic acid from water.

Figure 6. Distribution coefficient (D1) of water in the three solvents versus the mass fraction of acrylic acid in the solvent-rich phase (wI2) at 293.15 K.

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AUTHOR INFORMATION

Corresponding Author

*Tel.: +86 371 67756725. Fax: +86 371 67756718. E-mail: [email protected]. Funding

This work is supported by the Natural Science Fund of The Education Department of Henan Province (Grant No. 12B530001) and the major project of teaching reform fund of Henan University of Technology (2014GJYJ-A11). Notes

The authors declare no competing financial interest.

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Figure 7. Separation factor (S) of the three solvents versus the mass fraction of acrylic acid in solvent-rich phase (wI2) at 293.15 K.

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