Atmospheric Ternary Liquid–Liquid Equilibrium for the Diethyl

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Atmospheric Ternary Liquid−Liquid Equilibrium for the Diethyl Carbonate + 1‑Propanol + Water System at Temperature of 303.15, 313.15, 323.15, and 333.15 K Diana Rachmawati,† Ianatul Khoiroh,‡ Rizky Tetrisyanda,† and Gede Wibawa*,† †

J. Chem. Eng. Data Downloaded from pubs.acs.org by WEBSTER UNIV on 03/04/19. For personal use only.

Department of Chemical Engineering, Faculty of Industrial Technology, Sepuluh Nopember Institute of Technology (ITS), Kampus ITS Sukolilo, Surabaya 60111, Indonesia ‡ Department of Chemical and Environmental Engineering, Faculty of Engineering, University of Nottingham Malaysia Campus, Jalan Broga, Semenyih, 43500 Selangor Darul Ehsan, Malaysia S Supporting Information *

ABSTRACT: Liquid−liquid equilibrium (LLE) data for the ternary system composed of diethyl carbonate (DEC) + 1-propanol + water were measured under atmospheric pressure (101.32 ± 1 kPa) at temperature range of 303.15−333.15 K. The equilibrium data were found to be consistent with the Bachman−Brown method. The data were further correlated with the nonrandom two-liquid (NRTL) and the universal quasi-chemical (UNIQUAC) models, and 0.37% root-mean-square deviation was obtained between the experimental and calculated phase composition. Distribution coefficient and separation factor for this ternary system were calculated from the experimental data. and water.13−18 In our previous work, LLE data for a mixture composed of the DMC + 2-methyl-1-propanol or 2-methyl-2propanol + water systems have been measured at 303.15 and 313.15 K.19 Since the tropical country has maximum temperature above 303.15 K, the LLE data with a wider temperature range were necessary. Therefore, LLE data for the (DEC + 1-propanol + water) at 303.15, 313.15, 323.15, and 333.15 K were determined at atmospheric pressure in this work. The reliability of the experimental tie-line data was confirmed by using the Bachman−Brown correlation.20,21 The LLE data obtained were further correlated with the NRTL22 and the UNIQUAC23 activity coefficient models.

1. INTRODUCTION Methyl tert-butyl ether (MTBE) as a gasoline additive was found to be carcinogenic and pollutant in the groundwater.1−3 Ethanol, one of the short-chained alcohols, is the most promising gasoline additive alternative.4 However, the use of ethanol has several problems such as low heating value and tendency to induce phase splitting at low temperature.5 Therefore, it is of paramount importance to find cleaner alternatives to replace MTBE. Diethyl carbonate (DEC), also called carbonic acid diethyl ester, is an ideal candidate since it is readily miscible with diesel fuel, good blending octane, reduced CO and NOx emissions, low toxicity, and biodegradability.6 Moreover, DEC has a higher oxygen content of 40.7% w/w which leads to lower energy density and immiscibility with hydrocarbons.7 Compared to other potential oxygenate additives such as dimethyl carbonate (DMC), DEC has a higher heating value (74.3 MBtu·gal−1) which is significantly higher than DMC (55.6 MBtu·gal−1), lower vapor pressure, and better gasoline/water distribution coefficient.6 Liquid−liquid equilibrium (LLE) data and vapor−liquid equilibrium (VLE) data play an important role in understanding phase behavior for the multicomponent systems as a basis for designing a gasoline blending process and developing a solution theory. The VLE data for the fuel blend system containing DEC have been reported for several systems.8−11 It was found that gasoline distributed commercially contained water, from either humidity or leakage of the storage tanks.12 Therefore, the availability of LLE data is important to understand the phase behavior and the thermodynamic properties of systems containing water and alcohol with oxygenates. Recently, several studies have been reported for the ternary LLE systems containing DEC, alcohols, © XXXX American Chemical Society

2. EXPERIMENTAL SECTION 2.1. Materials. The chemicals used in these experiments were diethyl carbonate (DEC), 1-propanol, and water. The mass fraction purity reported by the manufacturers for DEC and 1-propanol was better than 0.995. Bidistilled water was used in this work. All materials were used as received without any additional purification process. The details of each compound used in this work are listed in Table 1. 2.2. Experimental Apparatus and Procedures. The experimental apparatus was the same as that reported in detail previously.19 Briefly, an equilibrium cell surrounded by a jacket was connected to a water bath to maintain the equilibrium Received: October 18, 2018 Accepted: February 13, 2019

A

DOI: 10.1021/acs.jced.8b00937 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 1. Purities and Suppliers of the Chemicals MWb component

supplier

CAS #

purity

diethyl carbonate 1-propanol bidistilled waterc

Wuhan Fortuna Chemical Co., China Merck, Germany

105-58-8 71-23-8

0.9992 0.9950

UNIQUAC parameterd

−1

a

g mol

118.13 60.10

r

q

4.41 2.78 0.92

3.90 2.51 1.40

Purity from supplier. bMW = molecular weight. cElectrical conductivity 3.0 μS·cm−1 at 298.15 K. dRef 23.

a

Table 2. Experimental LLE Data for the DEC (1) + 1-Propanol (2) + Water (3) System at T = 303.15−333.15 K and Pressure P = 101.32 kPaa

temperature. The total volume of the cell was found to be 40 cm3. The magnetic laboratory stirrer (Dragon Lab MS-H280Pro) was utilized to adjust the experimental temperatures. The equilibrium temperatures were controlled by a digital regulator (Anly At-502) equipped with an RTD Pt100 thermocouple. The uncertainty of the temperature, u(T), was found to be 0.1 K, while the uncertainty of pressure u(P) was 1 kPa, respectively. During the LLE experiment, the ternary solution was loaded to fill most of the equilibrium cell and leave only a small space for the stirring process. The pressure was adjusted by the use of a capillary pipe (8 cm × 2.5 cm × 0.5 mm) in order to ascertain that the experimental measurements were done at atmospheric pressure conditions. LLE measurements were performed at T = 303.15, 313.15, 323.15, and 333.15 K under atmospheric pressure. The uncertainty of temperature and pressure was ±0.2 K and ±1 kPa, respectively. About 40 cm3 ternary mixtures were prepared gravimetrically and were loaded in an equilibrium cell, stirred for 4 h, and then left to settle at constant temperature for 20 h until reaching equilibrium. At the end of the settling period, the twophase system, organic phase, and aqueous phase appeared. Phase compositions from both phases were analyzed by Shimadzu Plus 2010 gas chromatography (Japan) equipped with a thermal conductivity detector (TCD) and Q-Bond column. The carrier gas was high-purity helium with a flow rate of 8 mL·s−1, purge flow of 3 mL·s−1, and column flow of 2.3 mL·s−1 with a split ratio of 20:1. The injector, detector, and column temperatures were set to be 473.15, 523.15, and 513.15 K, respectively. The TCD was calibrated using binary calibration by plotting peak area fraction to mole fraction of component in the calibration curve. The solutions were prepared gravimetrically based on their binary pair (water/1-propanol and 1-propanol/DEC) for 12 calibration points. Samples from each phase were analyzed three times to obtain a mean value for each sample. The concentrations of the conjugated phases allowed us to construct the tie lines. The uncertainty in the mole fractions was about ±0.0003.

3. RESULTS AND DISCUSSION The experimental ternary LLE data for the DEC + 1-propanol + water system at T = 303.15, 313.15, 323.15, and 333.15 K under atmospheric pressure are presented in Table 2 and Table 3. The ternary diagrams, depicted in Figure 1, were constructed from the obtained experimental measurement. This figure shows that the DEC + 1-propanol + water systems exhibit Treybal type I ternary phase behavior with one pair of immiscible binary mixture of DEC + water and two pairs of completely miscible binary mixtures of 1-propanol + water and 1-propanol + DEC.24 Previously, the DEC + 1-propanol + water systems at 303.15 and 313.15 K have been studied.15 The comparison of experimental ternary data between literature data from Zeng et al. (2013)15 and this work at 303.15 and 313.15 K has been presented in Figure 2. The ternary plot shows that the experimental B

x1I

x2I

0.0437 0.0805 0.1289 0.1846 0.2575 0.3280 0.3815 0.5084 0.6403 0.7431 0.8398 0.9155

0.1815 0.2321 0.2589 0.2787 0.2899 0.2827 0.2684 0.2243 0.1666 0.1122 0.0549 0.0000

0.0414 0.0735 0.1253 0.1769 0.2514 0.3145 0.3652 0.4837 0.6081 0.7181 0.8218 0.9153

0.1765 0.2208 0.2555 0.2759 0.2900 0.2826 0.2688 0.2270 0.1759 0.1181 0.0589 0.0000

0.0337 0.0734 0.1155 0.1657 0.2371 0.3022 0.3583 0.4729 0.5902 0.7086 0.8079 0.8982

0.1532 0.2168 0.2441 0.2644 0.2823 0.2796 0.2680 0.2233 0.1795 0.1183 0.0607 0.0000

0.0602 0.1081 0.1569 0.2209 0.2830 0.3422 0.4637 0.5890 0.6951

0.1925 0.2346 0.2567 0.2726 0.2738 0.2640 0.2245 0.1737 0.1199

x3I T= 0.7748 0.6874 0.6122 0.5367 0.4526 0.3894 0.3502 0.2673 0.1931 0.1447 0.1053 0.0845 T= 0.7821 0.7056 0.6192 0.5473 0.4586 0.4029 0.3660 0.2893 0.2159 0.1637 0.1194 0.0847 T= 0.8132 0.7098 0.6404 0.5699 0.4807 0.4182 0.3737 0.3038 0.2303 0.1731 0.1314 0.1018 T= 0.7473 0.6573 0.5864 0.5064 0.4432 0.3938 0.3118 0.2373 0.1849

x1II 303.15 K 0.0053 0.0040 0.0032 0.0029 0.0032 0.0027 0.0026 0.0024 0.0023 0.0025 0.0017 0.0027 313.15 K 0.0059 0.0042 0.0034 0.0030 0.0029 0.0029 0.0027 0.0026 0.0022 0.0030 0.0020 0.0022 323.15 K 0.0078 0.0042 0.0037 0.0030 0.0028 0.0032 0.0028 0.0024 0.0025 0.0028 0.0017 0.0011 333.15 K 0.0048 0.0038 0.0033 0.0031 0.0033 0.0029 0.0024 0.0022 0.0020

x2II

x3II

0.0566 0.0457 0.0411 0.0387 0.0361 0.0320 0.0336 0.0315 0.0253 0.0211 0.0093 0.0000

0.9381 0.9503 0.9556 0.9584 0.9607 0.9654 0.9638 0.9661 0.9724 0.9764 0.9890 0.9973

0.0530 0.0440 0.0394 0.0372 0.0355 0.0310 0.0319 0.0299 0.0226 0.0178 0.0076 0.0000

0.9411 0.9518 0.9572 0.9598 0.9616 0.9661 0.9654 0.9675 0.9752 0.9793 0.9903 0.9978

0.0606 0.0436 0.0394 0.0358 0.0339 0.0310 0.0319 0.0267 0.0226 0.0170 0.0071 0.0000

0.9317 0.9522 0.9569 0.9612 0.9632 0.9658 0.9653 0.9709 0.9749 0.9802 0.9913 0.9989

0.0441 0.0390 0.0362 0.0342 0.0304 0.0313 0.0238 0.0188 0.0140

0.9511 0.9572 0.9605 0.9627 0.9663 0.9658 0.9738 0.9790 0.9840

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Table 2. continued x1I

x2I

x3I

0.7943

0.0592

0.1464

0.8776

0.0000

0.1224

x1II

x2II

x3II

0.0018

0.0061

0.9922

0.0021

0.0000

0.9979

T = 333.15 K

a

Standard uncertainties are u(T) = 0.1 K; u(xi) = 0.0003; and u(P) = 1 kPa where xi is in mole fraction. I is for organic phase and II for the aqueous phase.

Table 3. Bachman−Brown Parameter for the Ternary System of DEC + 1-Propanol + Water temperature

parametera

value

303.15 K

A B R2 A B R2 A B R2 A B R2

1.0068 0.0074 0.9997 1.0048 0.0072 0.9997 1.004 0.007 0.9997 1.0011 0.0077 0.9998

313.15 K

323.15 K

333.15 K

Figure 2. Experimental LLE for the ternary system of DEC + 1-propanol + water at 303.15 K (□) and 313.15 K (△), this work; and 303.15 K (■) and 313.15 K (▲), Zeng et al.15

a 2

R is the coefficient of determination.

Figure 3. Bachman−Brown plot for the ternary system of DEC + 1-propanol + water at 303.15 K (○), 313.15 K (□), 323.15 K (●), and 333.15 K (▲). Figure 1. Experimental LLE for the ternary system of DEC + 1-propanol + water at 303.15 K (■), 313.15 K (△), 323.15 K (●), and 333.15 K (○).

Table 4. NRTL and UNIQUAC Model TemperatureIndependent Parameters for the Ternary System of DEC + 1-Propanol + Water at 303.15−333.15 K

tie-line data connecting composition of both phases give good agreement. The experimental tie-line data were then checked using the Bachman−Brown correlation21 to confirm the reliability and check the consistency of the experimental tie-line. The tie-line consistency for LLE of the ternary system was proposed by Bachman (1940),20 and for the ternary system of DEC + 1-propanol + water, the following equation was used x1I x3II

=

Ax1I

NRTL parameter

+B (1) C

i−j

aij /K

aji(0)/K

aji(1)

α

RMSD

1−2 2−3 1−3

351.33 −6.09 8.41 246.67 −9.90 399.29 504.79 2.09 1426.38 UNIQUAC parameter

10.23 17.09 5.35

0.3

0.33%

(0)

aij(1)

i−j

aij(0)/K

aij(1)

aji(0)/K

aji(1)

RMSD

1−2 2−3 1−3

159.56 −20.97 354.31

−1.85 0.41 −0.67

59.69 162.53 193.66

1.13 −0.74 0.92

0.37%

DOI: 10.1021/acs.jced.8b00937 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Figure 4. LLE correlation for the ternary system of DEC + 1-propanol + water at (a) 303.15 K, (b) 313.15 K, (c) 323.15 K, and (d) 333.15 K. (−■−) experimental tie-line, () NRTL correlation, (- - -) UNIQUAC correlation.

experimental tie-line data. The binary energy parameters, aji, defined by a linear function of temperature, were used

where A and B are the Bachman−Brown correlation parameter; xI1 is the mole fraction of DEC in phase I (organic phase); and xII3 is the mole fraction of water in phase II (aqueous phase), respectively. The Bachman−Brown correlation for this experiment showed a good consistency by giving an R2 value of more than 0.9997 as shown in Table 3. The plot of the Bachman− Brown correlation in Figure 3 indicated that the experimental tie-line data were consistent. The solubility of diethyl carbonate + water from this work was compared with several literature data15,25,26 as shown in Figure S1 in the Supporting Information. It can be seen that the mutual solubility for each phase agrees well with those of the literature. The effect of temperature on phase boundary is presented in Figure 1. In the range of temperatures studied (303.15− 330.15 K), no significant effect was observed on the binodal curve for the DEC + 1-propanol + water system. This indicates that the studied mixture is more stable and may reduce the possibility of phase splitting in gasoline blending. Two activity coefficient models, the UNIQUAC and the NRTL models, were selected to correlate the experimental data at a temperature range of 303.15−330.15 K. In these models, the binary interaction parameters were obtained to represent the

y iT aij = aij(0) + aij(1)jjj − 273.15zzz { kK

(2)

where aij(0) and aij(1) are temperature-independent constants. The structural parameters for the UNIQUAC model, r and q, were taken from the literature.27 The value of alpha in the NRTL model for the LLE system polar mixture and nonpolar mixture was set between 0.2 and 0.47.22 The objective function (OF) as shown in eq 3 was utilized to determine the binary interaction parameter pairs OF =

∑ ∑ ∑ (xijkexp − xijkcal)2 k

i

(3)

j

Here i = 1 to 3 is the number of components; j = I, II denotes the phase; and k = 1 to n is the number of tie-lines. The root-meansquare deviation (RMSD) between the experimental and calculated values was evaluated by n

RMSD = D

exp cal 2 ∑k ∑j ∑i (xijk − xijk )

6n

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The best fit of the NRTL and UNIQUAC parameters, temperature range, along with the RMSD between experimental and calculated result are presented in Table 4. The experimental data together with the correlation results for all the investigated systems studied are displayed in Figure 4. In this figure, the tie lines measured in the present work are compared with those correlated with the NRTL and the UNIQUAC models for the studied system at several temperatures. The correlated results obtained from the models are shown to be in good agreement with the experimental ternary LLE data. The root-mean-square deviations for the NRTL and the UNIQUAC correlation models between the experimental and calculated phase composition were found to be 0.40% for the ternary system measured in this work. To observe better the influence of DEC addition on aqueous and organic phases, the distribution coefficient, D, and the separation factor, S, for DEC were calculated from the experimental tie-line data and defined as28−31 D=

S=

its mole fraction in the organic-rich phase. It is found that temperatures have no evident effect for the distribution coefficient for this system. The distribution coefficients and separation factors of DEC were decreasing as its mole fraction in the organic phase was increasing. This implies that the addition of DEC does not increase the solubility of DEC in the aqueous phase. This trend, however, was due to the presence of two ethyl groups in DEC which possessed hydrophobic character. DECs as gasoline additives were found to be more soluble with hydrocarbon compounds than water.32−34

4. CONCLUSIONS Liquid−liquid equilibrium (LLE) tie-line data for the DEC + 1-propanol + water system at T = 303.15, 313.15, 323.15, and 333.15 K under atmospheric pressure were determined experimentally. In the range of temperatures studied, the temperatures showed a slightly evident effect on phase boundary for the DEC + 1-propanol + water system. From the ternary diagram obtained in this work, it was found that the system studied shows Treybal type 1 behavior. The experimental ternary was correlated by both the NRTL and the UNIQUAC models with RMSD obtained of 0.37%.

x1II x1I

(5)

■

x1II/x1I x3II/x3I

(6)

ASSOCIATED CONTENT

S Supporting Information *

where superscripts I and II refer to the organic and aqueous phases. Figures 5 and 6 show the distribution coefficient and the separation factor of DEC at several temperatures as a function of

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.8b00937. Solubility comparison between experimental and literature data (PDF)

■

AUTHOR INFORMATION

Corresponding Author

*Fax: +62-31-5999282. Tel.: +62-31-5946240. E-mail: [email protected]. ORCID

Diana Rachmawati: 0000-0002-0933-0327 Gede Wibawa: 0000-0002-1255-9210 Notes

The authors declare no competing financial interest.

■

ACKNOWLEDGMENTS This research was supported by Penelitian Dasar Unggul Perguruan Tinggi (PDUPT) under Contract No. 128/SP2H/PTNBH/ DRPM/2018. The author would like to give credit to Rianti Widi Andari for her contributions to this experimental work.

Figure 5. Distribution coefficient of DEC in the ternary system of DEC + 1-propanol + water, D1, as a function of mole DEC in the organic-rich phase, x1I. 303.15 K (△), 313.15 K (○), 323.15 K (▲), 333.15 K (●).

■

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Figure 6. Separation factor, S, as a function of mole DEC in the organic-rich phase, x1I. 303.15 K (△), 313.15 K (○), 323.15 K (▲), 333.15 K (●). E

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