Isobaric Vapor–Liquid Equilibrium Data for Binary Systems of Anisole

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Isobaric Vapor−Liquid Equilibrium Data for Binary Systems of Anisole with Methyl Acetate, Ethyl Acetate, n‑Propyl Acetate, and Isopropyl Acetate at 93.9 kPa Bharat R. Bhoi,† Nilesh A. Mali,*,‡ and Sunil S. Joshi‡ ‡

Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, Maharashtra, India † Department of Chemical Engineering, Dr. Babasaheb Ambedkar Technological University, Lonere, Raigad - 402103, Maharashtra, India S Supporting Information *

ABSTRACT: The present work reports experimental isobaric vapor−liquid equilibrium data at 93.9 kPa pressure using a dynamic recirculation still for four binary pairs of acetates with anisole. The suitability of the experimental data for modeling was established by performing the Herington area test, Van Ness test, and mean absolute deviation test. Binary interaction parameters necessary for process modeling were derived through the regression of the VLE data for Wilson, NRTL, and UNIQUAC activity coefficient models with a suitable objective function. VLE data in the form of T−x, y plots indicates no formation of azeotropes for all pairs.

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INTRODUCTION In the perfume industry, anisole is widely used as a flavoring agent because of its aromatic odor. It also finds applications in the pharmaceutical industry. Synthetic anethole, which is used as an intermediate in many processes, can be prepared from anisole. It has also good demand from the pharmaceutical and agrochemical industries as an intermediate chemical. Some applications in distillation and as a solvent in extractive distillation for the separation of azeotropic mixtures have also been reported.1 Esters are also used as flavoring agents in the food and perfume industries. They are also used to synthesize surfactants, e.g., soaps and detergents. Hence, vapor−liquid equilibrium (VLE) data for anisole with various esters will be useful for designing separation equipment such as distillation columns and extraction columns where these solvents coexists. So, far VLE data of anisole with various hydrocarbons was reported in the literature by Torres et al.2 and Mali et al.,3 but data for binary systems of anisole with esters is not available. Per the NIST literature database,4 only the limiting activity coefficient data was reported for the ethyl acetate−anisole binary system by Thomas et al.5 The present work reports isobaric VLE data in the form of T−x, y at local atmospheric pressure of 93.9 kPa for anisole + methyl acetate, anisole + ethyl acetate, anisole + n-propyl acetate, and anisole + isopropyl acetate. Regression with a suitable objective function was performed for Wilson, NRTL, and UNIQUAC activity coefficient models to estimate the binary interaction parameters. © XXXX American Chemical Society

EXPERIMENTAL SECTION Materials. Details of the chemicals used in the experimental work are reported in Table 1. Boiling points and refractive Table 1. Component, Supplier, and Purity of Chemicals chemical

CAS no.

anisole methyl acetate ethyl acetate n-propyl acetate isopropyl acetate

100-66-3 79-20-9 141-78-6 109-60-4 108-21-4

supplier Loba Loba Loba Loba Loba

Chemie Chemie Chemie Chemie Chemie

purity (mass %) 99 99 99.5 98 99

indices of all chemicals used were measured, and the results are tabulated in Table 2. All chemicals were used directly for the experiment, and no additional purification was done. Measured refractive index (nD) and boiling point (Tb) values of all components were compared with the literature data in Table 2. Apparatus Details and Experimental Procedure. The apparatus proposed in our earlier work3 was used for the experimental analysis. It is a dynamic type apparatus in which both vapor and liquid phases are circulated continuously through an equilibrium chamber until equilibrium is achieved. Received: January 19, 2018 Accepted: April 16, 2018

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Table 2. Refractive Indices (nD) and Boiling Points (Tb) refractive index (nD) at 298.15 K chemical

literature

anisole methyl acetate ethyl acetate n-propyl acetate isopropyl acetate

measureda

6

1.5150 1.36028 1.37108 1.38289 1.374579

Table 4. Experimental VLE Data for the System Methyl Acetate (1) + Anisole (2) at 93.9 kPaa

boiling point (K) literature (at 101.325 kPa)

1.51554 1.35869 1.36970 1.38169 1.37463

7

427.15 329.8511 350.2511 374.410 361.910

measured (at 93.9 kPa)a 423.92 327.90 347.92 372.17 359.68

a

Standard uncertainties u are u(nD) = 0.003, u(T) = 0.1 K, and u(P) = 0.1 kPa.

Equilibrium was confirmed based on the constant temperature of the equilibrium chamber. Once equilibrium was achieved, samples of equilibrium liquid and vapor were withdrawn and analyzed for the composition. The equilibrium sample composition was also checked with time to confirm vapor−liquid equilibrium. The experiment was concluded when the compositions of two equilibrium samples withdrawn at some time interval were the same. Similar experiments were performed for different feed compositions to cover the complete composition range for the binary system. A very small quantity of sample (less than 1 mL) was withdrawn so that the equilibrium was not disturbed. The reliability of the equipment was already established in our previous works through a comparison of the experimental VLE data with the data reported in the literature.3,12 Equilibrium Composition Analysis. Equilibrium compositions of vapor and liquid samples were determined using a refractive index measurement with a refractometer (ATAGO RX7000i). The refractive index of the equilibrium sample was measured, and the composition was estimated using a calibration equation correlating the refractive index with the mole fraction.

T/K

X1

Y1

γ1

327.90 329.25 330.26 332.45 336.69 339.39 344.15 351.39 364.10 375.33 400.92 410.44 423.92

1.0000 0.9495 0.9147 0.8395 0.7129 0.6429 0.5374 0.4142 0.2655 0.1798 0.0608 0.0320 0.0000

1.0000 0.9983 0.9970 0.9938 0.9870 0.9823 0.9717 0.9508 0.8962 0.8226 0.5177 0.3393 0.0000

1.000 1.003 1.004 1.010 1.024 1.034 1.051 1.067 1.088 1.092 1.104 1.121

γ2

α21

1.174 1.136 1.125 1.072 1.029 1.018 1.015 1.010 1.008 1.006 1.001 1.000

0.033 0.032 0.033 0.033 0.032 0.034 0.037 0.042 0.047 0.060 0.064

a Standard uncertainties u are u(x1) = 0.001, u(y1) = 0.001, u(T) = 0.1 K, and u(P) = 0.1 kPa.

Table 5. Experimental VLE Data for the System Ethyl Acetate (1) + Anisole (2) at 93.9 kPaa

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RESULTS AND DISCUSSION Calibration Curves for Composition Analysis. The calibration curves’ data and plots generated at 293.15 K are listed in the Supporting Information in Tables S1−S4 and Figures S1−S4, respectively. The refractive index data of known composition samples was regressed with a fifth-order polynomial equation to obtain the equation parameters. All equations with parameters are listed in Table 3, where x is the mole fractions of acetates and y is the refractive index. Experimental VLE Data. VLE experimentation was performed at a pressure of 93.9 kPa for all binary pairs, which was the atmospheric pressure where the experiments were conducted. The data in the form of T−x, y is tabulated in Tables 4−7. The corresponding T−x, y plots are shown in Figures 1−4. The reliability of the experimental data was established by checking the thermodynamic consistency of the data using Herington, Van Ness, and mean absolute deviation tests as discussed in the next section.

T/K

X1

Y1

γ1

347.92 349.40 351.38 353.45 357.23 361.53 366.40 372.90 381.28 393.64 406.38 414.49 423.92

1.0000 0.9465 0.8805 0.8162 0.7115 0.5981 0.4932 0.3822 0.2736 0.1600 0.0785 0.0384 0.0000

1.0000 0.9952 0.9887 0.9817 0.9681 0.9480 0.9214 0.8779 0.8058 0.6592 0.4425 0.2615 0.0000

1.000 1.001 1.002 1.003 1.006 1.026 1.044 1.063 1.081 1.097 1.103 1.110

γ2

α21

1.187 1.141 1.100 1.045 1.024 1.013 1.007 1.006 1.003 1.002 1.001 1.000

0.086 0.084 0.083 0.081 0.082 0.083 0.086 0.091 0.098 0.107 0.113

a Standard uncertainties u are u(x1) = 0.001, u(y1) = 0.001, u(T) = 0.1 K, and u(P) = 0.1 kPa.

Data Reduction. Raoult’s law modified with an activity coefficient to account for liquid-phase nonideality was used for VLE modeling as given by eq 1.13

yP = xiγiPi sat i

(1)

Pisat,

Vapor pressure, was estimated using Antoine’s equation (eq 2) with the constants listed in Table 8. ⎛ Bi ⎞ log10Pi sat = Ai − ⎜ ⎟ ⎝ T + Ci ⎠

(2)

The activity coefficient, γi, was calculated with the Wilson, NRTL, and UNIQUAC activity coefficient models. The saturated liquid-phase partial molar volume of pure component i was calculated by Rackett equation14 (eq 3).

Table 3. Calibration Curves Equation binary pair methyl acetate + anisole ethyl acetate + anisole n-propyl acetate + anisole isopropyl acetate + anisole

polynomial equation y y y y

= = = =

−0.2034x5 + 0.6018x4 − 0.6422x3 + 0.2253x2 − 0.1369x + 1.5166 −0.0679x5 + 0.1652x4 − 0.1418x3 + 0.0301x2 − 0.13x + 1.5168 0.0226x5 − 0.0536x4 + 0.0517x3 − 0.021x2 − 0.1324x + 1.5168 −0.1946x5 + 0.5106x4 − 0.46x3 + 0.1613x2 − 0.1567x + 1.5166 B

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Table 6. Experimental VLE Data for the System n-Propyl Acetate (1) + Anisole (2) at 93.9 kPaa T/K

X1

Y1

γ1

372.17 373.42 374.72 377.20 380.89 384.52 389.01 393.25 399.19 405.96 413.97 419.00 423.92

1.0000 0.9477 0.8930 0.8026 0.6865 0.5868 0.4793 0.3911 0.2855 0.1866 0.0921 0.0436 0.0000

1.0000 0.9887 0.9760 0.9519 0.9141 0.8727 0.8145 0.7513 0.6476 0.5068 0.3053 0.1621 0.0000

1.000 1.004 1.010 1.016 1.022 1.027 1.032 1.038 1.045 1.050 1.051 1.047

γ2

α21

1.076 1.071 1.060 1.045 1.035 1.027 1.022 1.020 1.017 1.012 1.004 1.000

0.206 0.206 0.205 0.206 0.207 0.210 0.213 0.217 0.223 0.231 0.235

Figure 2. T−x, y plot for ethyl acetate (1) + anisole (2); □, T−y (experiment at 93.9 kPa); ◊, T−x (experiment at 93.9 kPa); , Wilson model; ···, NRTL model; and ---, UNIQUAC model.

a

Standard uncertainties u are u(x1) = 0.001, u(y1) = 0.001, u(T) = 0.1 K, and u(P) = 0.1 kPa.

Table 7. Experimental VLE Data for the System Isopropyl Acetate (1) + Anisole (2) at 93.9 kPaa T/K

X1

Y1

γ1

359.68 360.92 362.15 365.69 369.50 373.30 378.12 383.95 391.40 399.22 412.15 417.38 423.92

1.0000 0.9538 0.9102 0.7963 0.6855 0.5885 0.4833 0.3770 0.2686 0.1796 0.0711 0.0369 0.0000

1.0000 0.9935 0.9869 0.9673 0.9428 0.9149 0.8741 0.8152 0.7228 0.6012 0.3334 0.1972 0.0000

1.000 1.001 1.002 1.004 1.010 1.018 1.028 1.041 1.056 1.069 1.086 1.092

γ2

α21

1.142 1.125 1.077 1.054 1.039 1.026 1.016 1.008 1.004 1.001 1.000 1.000

0.135 0.134 0.132 0.132 0.133 0.135 0.137 0.141 0.145 0.153 0.156

Figure 3. T−x, y plot for n-propyl acetate (1) + anisole (2); □, T−y (experiment at 93.9 kPa); ◊, T−x (experiment at 94.2 kPa); , Wilson model; ···, NRTL model; and ---, UNIQUAC mode.

a

Standard uncertainties u are u(x1) = 0.001, u(y1) = 0.001, u(T) = 0.1 K, and u(P) = 0.1 kPa.

Figure 1. T−x, y plot for methyl acetate (1) + anisole (2); □, T−y (experiment at 93.9 kPa); ◊, T−x (experiment at 93.9 kPa); , Wilson model; − − − , NRTL model; and ···, UNIQUAC model.

Figure 4. T−x, y plot for isopropyl acetate (1) + anisole (2); □, T−y (experiment at 93.9 kPa); ◊, T−x (experiment at 94.2 kPa); , Wilson model; ···, NRTL model; and ---, UNIQUAC model.

2/7

Vi = VciZci(1 − Tr)

(3)

Tr =

Vc and Zc are the critical parameters of component i given in Table 9, and Tr is the reduced temperature calculated from eq 4.

T Tci

(4)

Relative volatility (α21) was calculated using eq 5, C

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Table 8. Antoine Constants17 Antoine constants chemical

A

B

C

anisole methyl acetate ethyl acetate n-propyl acetate isopropyl acetate

4.17726 4.20364 4.22809 4.14386 4.55172

1489.756 1164.426 1245.702 1283.861 1490.877

−69.607 −52.69 −55.189 −64.378 −34.098

Table 9. Critical Parameters17 3

chemical

Vc (cm /mol)

Zc

Tc (K)

anisole methyl acetae ethyl acetate n-propyl acetate isopropyl acetae

0.343 0.229 0.288 0.347 0.343

0.268 0.257 0.257 0.257 0.258

646.1 506.51 523.26 549.69 531.07

anisole18

methyl acetate19

ethyl acetate20

n-propyl acetate21

isopropyl acetate22

r q

4.1667 3.2080

2.8042 2.5760

3.4786 3.116

4.153 3.656

4.1522 3.6520

a

α21

a

α21exp

Wilson

NRTL

UNIQUAC

329.25 330.26 332.45 336.69 339.39 344.15 351.39 364.10 375.33 400.92 410.44

0.0327 0.0321 0.0327 0.0328 0.0324 0.0338 0.0366 0.0419 0.0473 0.0603 0.0643

0.0338 0.0335 0.0330 0.0330 0.0334 0.0344 0.0368 0.0419 0.0471 0.0603 0.0656

0.0331 0.0332 0.0333 0.0339 0.0344 0.0355 0.0375 0.0420 0.0466 0.0586 0.0634

0.0329 0.0328 0.0328 0.0332 0.0336 0.0347 0.0370 0.0417 0.0465 0.0586 0.0634

T T T T T

temperature range (K) = = = = =

K K K K K

383.03−437.26 274.91−328.99 288.73−348.98 312.22−374.03 234.09−362.05

T/K

α21exp

Wilson

NRTL

UNIQUAC

373.42 374.72 377.20 380.89 384.52 389.01 393.25 399.19 405.96 413.97 419.00

0.2062 0.2057 0.2053 0.2059 0.2072 0.2097 0.2126 0.2174 0.2233 0.2308 0.2354

0.2114 0.2106 0.2097 0.2092 0.2093 0.2100 0.2112 0.2136 0.2170 0.2218 0.2252

0.2139 0.2128 0.2114 0.2104 0.2102 0.2106 0.2117 0.2139 0.2172 0.2221 0.2255

0.2086 0.2084 0.2083 0.2086 0.2093 0.2103 0.2116 0.2137 0.2165 0.2204 0.2231

Standard uncertainties u are u(T) = 0.1 K and u(P) = 0.1 kPa.

Table 14. Experimental and Calculated Relative Volatility Values for Isopropyl Acetate (1) + Anisole (2) at 93.9 kPaa α21

Standard uncertainties u are u(T) = 0.1 K and u(P) = 0.1 kPa.

Table 12. Experimental and Calculated Relative Volatility Values for Ethyl Acetate (1) + Anisole (2) at 93.9 kPaa

a

T/K

α21exp

Wilson

NRTL

UNIQUAC

360.92 362.15 365.69 369.50 373.30 378.12 383.95 391.40 399.22 412.15 417.38

0.1351 0.1343 0.1320 0.1322 0.1331 0.1347 0.1372 0.1408 0.1452 0.1529 0.1561

0.1335 0.1333 0.1330 0.1330 0.1335 0.1345 0.1363 0.1393 0.1431 0.1501 0.1531

0.1267 0.1271 0.1284 0.1300 0.1316 0.1339 0.1370 0.1413 0.1460 0.1543 0.1577

0.1299 0.1301 0.1308 0.1317 0.1328 0.1345 0.1369 0.1404 0.1443 0.1512 0.1540

Standard uncertainties u are u(T) = 0.1 K and u(P) = 0.1 kPa.

α21

a

bar, bar, bar, bar, bar,

α21

Table 11. Experimental and Calculated Relative Volatility Values for Methyl Acetate (1) + Anisole (2) at 93.9 kPaa T/K

= = = = =

Table 13. Experimental and Calculated Relative Volatility Values for n-Propyl Acetate (1) + Anisole (2) at 93.9 kPaa

Table 10. UNIQUAC Parameters parameter

units P P P P P

y2

T/K

α21exp

Wilson

NRTL

UNIQUAC

349.40 351.38 353.45 357.23 361.53 366.40 372.90 381.28 393.64 406.38 414.49

0.0857 0.0840 0.0827 0.0813 0.0816 0.0830 0.0860 0.0908 0.0985 0.1073 0.1127

0.0848 0.0839 0.0834 0.0831 0.0833 0.0845 0.0870 0.0912 0.0985 0.1069 0.1125

0.0849 0.0846 0.0844 0.0846 0.0850 0.0861 0.0883 0.0920 0.0986 0.1063 0.1115

0.0820 0.0819 0.0821 0.0827 0.0835 0.0850 0.0876 0.0916 0.0983 0.1058 0.1107

α21 =

x2 1 − y2

(5)

1 − x2

UNIQUAC model parameters r and q were taken from the literature as given in Table 10. The objective function used for activity coefficient model regression is given by eq 6. The objective function was minimized by varying the binary interaction parameters of the model. ⎡ ⎛ exp ⎤ cal ⎞2 ⎛ P exp − P cal ⎞2 ⎥ 1 ⎢ ⎜ y1 − y1 ⎟ OF = ⎢∑ ⎜ ⎟ + ⎜⎝ P exp ⎟⎠ ⎥ N y1exp ⎠ ⎣ ⎝ ⎦

Standard uncertainties u are u(T) = 0.1 K and u(P) = 0.1 kPa.

(6)

Experimental and calculated relative volatility values were compared, and the results are given in Tables 11−14. A D

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Table 15. Herington and Van Ness Consistency Tests Results Van Ness test Herington test

Wilson

NRTL

UNIQUAC

systems

|D − J|

Δy

Δp

Δy

Δp

Δy

Δp

results

methyl acetate + anisole ethyl acetate + anisole n-propyl acetate + anisole isopropyl acetate + anisole

9.73 9.54 6.96 9.14

0.05 0.05 0.24 0.12

0.29 0.22 0.40 0.39

0.13 0.12 0.25 0.08

0.60 0.24 0.37 0.26

0.14 0.13 0.31 0.08

0.50 0.32 0.59 0.13

passed passed passed passed

For the Van Ness test, Δy and Δp for n data points, as calculated using eqs 9 and 10, respectively, should be less than or equal to 1.16

Table 16. Criteria of the Absolute Mean Deviation Consistency Test23 sr. no

deviation parameter

1

formula

1 δy = N

vapor mole fraction

2

δP =

total pressure (kPa)

1 N

criteria

N

∑ (yi ,j

cal

exp

− yi , j )

Δy =

δy ≤ 0.01

i=1

δP ≤ 1.33

Δp =

i=1

Table 17. Results of the Absolute Mean Deviation Consistency Test sr. no

binary system

δy

δP (kPa)

1 2 3 4

methyl acetate + anisole ethyl acetate + anisole n-propyl acetate + anisole isopropyl acetate + anisole

0.0014 0.0015 0.0030 0.001

0.47 0.22 0.35 0.13

x =1

D = 100 ×

2

γ1

∫x = 0 ln γ dx1

(7)

2

⎛ T − Tmin ⎞ J = 150 × ⎜ max ⎟ Tmin ⎠ ⎝

n i=1

Pi cal − Pi exp Pi exp

(10)

CONCLUSIONS Vapor−liquid equilibrium data for binary systems anisole + methyl acetate, anisole + ethyl acetate, anisole + n-propyl acetate, and anisole + isopropyl acetate was generated at atmospheric pressure of 93.9 kPa in the form of T−x, y plots. A dynamic-type recirculation apparatus was used to generate the experimental data. The thermodynamic consistency was checked by Herington, Van Ness, and mean absolute deviation tests, and the data was found to be thermodynamically consistent. From the T−x, y plots and relative volatility data of the mixture, it was observed that the mixtures can be

γ

1

∑ 100

(9)

i=1

■

∫x =1 0 ln γ1 dx1 x1= 1

1 n

− yi exp |

Superscripts exp and cal indicate experimental and calculated values, respectively. Consistency parameter values are tabulated in Table 15. The consistency of the data was also checked using a mean absolute deviation which is based on the absolute average deviation between the experimental and calculated total pressure and vapor-phase composition. The criteria and results of the mean absolute deviation test are as given in Tables 16 and 17, respectively. A regression exercise for deriving binary interaction parameters of all three models indicated good fitting to the data and the consistency of the VLE data with the three tests. Binary interaction parameters of the models estimated through the regression exercise are listed in Table 18.

graphical comparison of both relative volatility values is given in the Supporting Information in Figures S5−S8. D and J parameters as given by eqs 7 and 8, and then the |D − J| values were calculated for the Herington method, which needs to be less than 10 for consistent VLE data.15 1

∑ 100|yi cal

N

∑ (Pi cal − Pi exp)

n

1 n

(8)

Table 18. Binary Interaction Parameters Estimated through the Regression of Activity Coefficient Models binary system methyl acetate + anisole

ethyl acetate + anisole

n-propyl acetate + anisole

isopropyl acetate + anisole

interaction parameter

NRTLa

Wilsonb

UNIQUACc

A12 A21 α A12 A21 α A12 A21 α A12 A21 α

260.124 211.047 0.3 264.307 166.810 0.3 184.659 141.234 0.3 112.674 179.812 0.3

−146.332 987.993

525.136 −470.352

405.654 181.886

86.604 −113.765

10.976 320.181

429.318 −453.645

72.446 332.976

−5.234 −40.029

a The interaction parameters for the NRTL model: A12(J mol−1) = (gij − gii)/R. bThe interaction parameters for the Wilson model: A12(J mol−1) = (λij − λii)/R. cThe interaction parameters for the UNIQUAC model: A12(J mol−1) = (Uij − Uii)/R.

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separated easily using conventional distillation. The Wilson, NRTL, and UNIQUAC models were correlated with the experimental data, and binary interaction parameters were determined. The prediction of all activity coefficient models closely matches the experimental VLE data with the regressed binary interaction parameters. No azeotropic behavior was observed for any pair.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.8b00063. Refractive index vs mole fraction data for various binary pairs of anisole with acetates and a comparison of relative volatility (α) data for various binary pairs of anisole with acetates (PDF)

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AUTHOR INFORMATION

Corresponding Author

*Tel: +91 20 25902176. Fax: +91 20 21762621. E-mail: na. [email protected]. ORCID

Nilesh A. Mali: 0000-0001-6832-9230 Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS The authors are thankful to CSIR-National Chemical Laboratory, Pune (Maharashtra), India for supporting the present work.

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REFERENCES

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DOI: 10.1021/acs.jced.8b00063 J. Chem. Eng. Data XXXX, XXX, XXX−XXX