LiquidâLiquid Extraction of Cyclopentanone from Aqueous Solution

Article Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Liquid−Liquid Extraction of Cyclopentanone from Aqueous Solution with Methylcyclohexane or Propyl Acetate at Different Temperatures Liping Wang, Saisai Zhou, Midong Shi, Bing Jia, Hai Liu, and Qingsong Li*

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State Key Laboratory of Heavy Oil Processing, College of Chemical Engineering, China University of Petroleum - East China, Qingdao, Shandong 266580, China ABSTRACT: Our research extends the knowledge into the liquid−liquid extraction regarding ternary mixtures of water + cyclopentanone + extractants (methylcyclohexane and propyl acetate) at 308.2, 318.2, and 328.2 K and 101.3 kPa. The extracting capabilities of the selected extractants were explored when it came to the distribution coefficient and selectivity on the basis of the liquid−liquid equilibrium values, while the consistency of the dependability of the tie-line values was corroborated utilizing both the Bachman and Hand empirical equations. In addition, the binary interaction energy parameters of the compounds were achieved by two classic activity coefficient models (i.e., NRTL and UNIQUAC); satisfactory results were yielded with all the fitting root-mean square deviations (rmsd %) ≤ 0.71.

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INTRODUCTION Cyclopentanone (CPO) is attracting particular interest as a versatile compound largely utilized for the manufacturing of biologically and industrially significant chemicals.1,2 CPO has been corroborated to be promising on commercial efficacy in the preparation of pharmaceuticals, fungicides, and perfume ingredients.3−5 Meanwhile, it can be used as a feedstock for the production of polyolefin stabilizers and C15 and C17 fuel precursors.6,7 Due to the widespread use of CPO in industry, all kinds of reaction processes have been studied for the synthesis of CPO. According to the references,6−9 the method of synthesizing CPO in an aqueous medium by furfural is feasible. Unfortunately, this approach produces enormous quantities of industrial wastewater containing CPO. Therefore, separation of CPO from water is becoming increasingly important and urgent. It is well established that ordinary distillation has been used to separate the CPO from water solutions, and it makes the separation difficult, energy-consuming, and less efficient.10 In contrast, solvent extraction is a satisfactory separation strategy on account of that it is easy to operate and energy-saving. Thus, the extraction technique was applied to separate CPO from the water system via different solvents in our present study. For obtaining the liquid−liquid equilibrium (LLE) data for relevant components, Thidarat Wongsawa and Gaoyin He et al. measured the ternary LLE data for water + cyclopentanone + solvents (MIBK, ethyl acetate, benzene, and toluene).11,12 It is worth mentioning, that looking for new and more effective extractants for the recovery of CPO is still the primary factor. In this article, methylcyclohexane and propyl acetate were selected for extracting CPO from water because of their low viscosity, low vapor pressure, and slight solubility in water.13,14 The objective of this work was to explore the feasibility of extracting CPO from water using methylcyclohexane or propyl © XXXX American Chemical Society

acetate at 308.2, 318.2, and 328.2 K and 101.3 kPa. As far as we know, there have been no reports regarding these ternary mixtures. First, the effectiveness of extracting CPO from aqueous solution was assessed by calculating the values of the distribution parameter and selectivity,15,16 and the results suggested that methylcyclohexane revealed a large separation factor of extraction. Then, Bachman and Hand equations were chosen to attest the dependability of the tie-line results.17,18 Finally, all measured LLE data were correlated to yield the binary interaction energy parameters via NRTL19 and UNIQUAC20 activity coefficient models.

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EXPERIMENTAL DESIGN Materials. All chemical materials and their characteristics used in this study are presented in Table 1. Double-distilled water was used in the current research. Cyclopentanone, methylcyclohexane, and propyl acetate with mass percent purity higher than 99.0% were supplied by Aladdin Industrial Corporation (China). Moreover, the purity of these chemicals was detected by an Agilent GC6820 gas chromatographer, and all chemicals were used directly with no further purification. Experimental Set-up. The experimental values regarding (water + cyclopentanone + methylcyclohexane or propyl acetate) mixtures were determined at 308.2, 318.2, and 328.2 K under 101.3 kPa. More detailed information on the experimental apparatus had been intensively investigated in our earlier studies, and the dependability of the experimental set-up has been assessed.21,22 The mixture of chemical reagents was charged into a glass-sealed cell, with vigorous stirring over 3 h, and then Received: December 25, 2017 Accepted: July 9, 2018

A

DOI: 10.1021/acs.jced.7b01109 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Material Descriptions component

CAS

source

chemical formula

mass percent purity

analysis method

cyclopentanone methylcyclohexane propyl acetate double-distilled waterb

120-92-3 108-87-2 109-60-4 7732-18-5

Aladdin Industrial Corporation Aladdin Industrial Corporation Aladdin Industrial Corporation self-made

C5H8O C7H14 C5H10O2 H2O

0.9972 0.9983 0.9976

GCa GC GC

Gas chromatography. bThe electrical conductivity of water is 8.35 μs/cm.

a

set aside for more than 12 h. By testing the setting time, it was shown that 12 h was enough to bring the ternary mixture to equilibrium. In this study, the temperature was kept constant at the desired temperature by a thermostatically controlled water bath, which had a standard uncertainty of approximately 0.1 K.23 Analysis. After the ternary mixture formed a two phase equilibrium, the samples were taken out by a microsyringe from both phases, respectively, and analyzed by a GC (Agilent GC6820 gas chromatographer). Briefly, this series of chromatograph was equipped with a 3 m × 3 mm Porapak N column and a thermal conductivity detector (TCD). Good peak detection was achieved according to the design of the operating procedures as follows. The temperature of the detector and injector port was fixed at 523.2 K, and they stayed at an initial temperature of 388.2 K for 3 min. The column temperature was enhanced to 523.2 at 20 K/min. Notably, hydrogen was utilized as the carrier gas at the rate of 1 cm3/s. In advance, a standard analysis method was enforced to switch the peak area ratio into a mass composition, and isopropyl alcohol was selected as the standard substance. A series of LLE data were achieved by altering the feed composition, and each sample was repeated three times to ensure data reliability. Uncertainty Calculation. Two classifications, which were named as “A” and “B”, were adopted to calculate the uncertainty.23 The uncertainty of quantity q in this work was calculated by type “A”, and relevant equations are shown below

Table 2. Experimental Tie-Line Data for the Ternary Water (1) + Cyclopentanone (2) + Methylcyclohexane (3) System at 308.2−328.2 K and 101.3 kP.a organic phase

aqueous phase

T (K)

xI1

xI2

xII1

xII2

D

S

308.2

0.0028 0.0033 0.0040 0.0049 0.0056 0.0072 0.0088 0.0141 0.0032 0.0040 0.0048 0.0058 0.0075 0.0090 0.0138 0.0215 0.0036 0.0045 0.0058 0.0064 0.0078 0.0104 0.0133 0.0212

0.0329 0.0692 0.1122 0.1584 0.2086 0.2617 0.3241 0.3894 0.0326 0.0697 0.1153 0.1635 0.2137 0.2666 0.3289 0.3865 0.0359 0.0758 0.1203 0.1732 0.2295 0.2913 0.3623 0.4259

0.9953 0.9913 0.9873 0.9836 0.9805 0.9775 0.9747 0.9723 0.9960 0.9923 0.9887 0.9851 0.9821 0.9799 0.9769 0.9748 0.9960 0.9925 0.9893 0.9860 0.9830 0.9804 0.9778 0.9755

0.0046 0.0086 0.0125 0.0163 0.0193 0.0223 0.0251 0.0276 0.0039 0.0076 0.0112 0.0147 0.0177 0.0199 0.0229 0.0250 0.0039 0.0074 0.0106 0.0139 0.0168 0.0194 0.0220 0.0243

7.12 8.05 8.94 9.73 10.80 11.74 12.92 14.13 8.28 9.19 10.32 11.13 12.08 13.37 14.34 15.44 9.19 10.25 11.38 12.46 13.63 14.98 16.44 17.49

2535 2416 2219 1951 1901 1600 1426 976 2598 2256 2146 1905 1574 1457 1012 699 2570 2237 1945 1927 1729 1418 1208 807

318.2

328.2

n

s 2(qk ) =

∑ (qj − q ̅ )2 /(n − 1) j=1

(1) a

2

2

s (q ̅ ) = s (qk )/n

(2)

u(xi) = s(X̅i )

(3)

Standard uncertainties u are u(T) = 0.1K, u(P) = 1.0 kPa, u(xI1) = 0.0011, u(xI2) = 0.0027, u(xII1 ) = 0.0041, and u(xII2 ) = 0.0013.

cyclopentanone and methylcyclohexane, demonstrating that the miscibility between methylcyclohexane and water was near zero. With regard to propyl acetate, it possessed a larger miscibility with water. For the water + cyclopentanone + propyl acetate system, the immiscible regions were diminished gradually with the increase of temperature, as shown in Figure 8. However, the effect of temperature on the immiscible zones of the water + cyclopentanone + methylcyclohexane system was almost negligible. In this work, the distribution parameter (D) and selectivity (S)15,16 were computed to assess the solvent separation efficiency, the equations are described as follows:

The standard deviation [s(qk)] was used to describe the variability of observations qk or its dispersion regarding its average value q̅, determined according to the experimental data. Therefore, for the input amount Xi, the type A standard uncertainty u(xi) of its estimate xi = x̅ i is u(xi) = s(Xi).

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RESULTS AND DISCUSSION Experimental Values. Experimental LLE values regarding the ternary mixtures of water + cyclopentanone + methylcyclohexane as well as water + cyclopentanone + propyl acetate were determined at 308.2, 318.2, and 328.2 K, displayed in Tables 2 and 3, respectively. All of the concentrations were represented by mole fraction. Figures 1, 2, 3, 4, 5, and 6 present triangle diagrams regarding these ternary mixtures at the measured temperature scope. The effect of the temperature on the equilibrium behavior of the water + cyclopentanone + methylcyclohexane and water + cyclopentanone + propyl acetate systems is drawn in Figures 7 and 8. In Figure 7, phase points of the aqueous and organic phases were, respectively, located at the composition lines of

D=

x 2I x 2II

(4) I

() S= () x2 x1

x2 x1

xI1

II

(5)

xII1

here and refer to, respectively, the mole fraction of water in the organic and water phases. While xI2 and xII2 designated, B



Article

Table 3. Experimental Tie-Line Data for the Ternary Water (1) + Cyclopentanone (2) + Propyl Acetate (3) System at 308.2−328.2 K and 101.3 kPaa organic phase

aqueous phase

T (K)

xI1

xI2

xII1

xII2

D

S

308.2

0.1079 0.1186 0.1335 0.1424 0.1471 0.1668 0.1861 0.1973 0.1579 0.1735 0.1750 0.1815 0.1912 0.2147 0.2196 0.2409 0.1951 0.1967 0.2034 0.2123 0.2323 0.2487 0.2701 0.3065

0.0860 0.1284 0.1712 0.2136 0.2567 0.2940 0.3295 0.3683 0.0850 0.1262 0.1697 0.2110 0.2515 0.2864 0.3271 0.3999 0.0814 0.1236 0.1667 0.2048 0.2416 0.2755 0.3510 0.3702

0.9868 0.9848 0.9828 0.9809 0.9788 0.9761 0.9739 0.9722 0.9905 0.9892 0.9875 0.9858 0.9837 0.9819 0.9770 0.9745 0.9909 0.9892 0.9874 0.9855 0.9834 0.9818 0.9776 0.9754

0.0038 0.0058 0.0080 0.0103 0.0127 0.0153 0.0178 0.0204 0.0033 0.0050 0.0069 0.0088 0.0109 0.0129 0.0171 0.0206 0.0031 0.0048 0.0067 0.0085 0.0106 0.0126 0.0172 0.0197

22.72 22.08 21.34 20.79 20.28 19.20 18.55 18.08 25.47 25.05 24.56 23.93 23.06 22.13 19.09 19.44 26.18 25.60 25.02 23.97 22.69 21.95 20.35 18.75

208 183 157 143 135 112 97 89 160 143 139 130 119 101 85 79 133 129 121 111 96 87 74 60

318.2

328.2

Figure 2. Ternary phase diagram for the water (1) + cyclopentanone (2) + methylcyclohexane (3) system at 318.2 K and 101.3 kPa: (*) experimental data; (☆) feed composition; (△) NRTL model; and (●) UNIQUAC model.

a

Standard uncertainties u are u(T) = 0.1 K, u(P) = 1.0 kPa, u(xI1) = 0.0029, u(xI2) = 0.0021, u(xII1 ) = 0.0044, and u(xII2 ) = 0.0015.


noted that, the distribution coefficients decreased as the CPO concentration in the water phase increased when propyl acetate was employed as the extractant. Furthermore, the slope factor of tie lines reflected the same tendency. That is because the distribution coefficient represented the solute-carrying capability of the extractant.24,25 With the increase of temperature, the distribution coefficients increased when methylcyclohexane or propyl acetate was used as the extractant, the order of which was D308.2 K < D318.2 K < D328.2 K. Whereas, it can be found that, the distribution parameter was basically temperature-independent of the whole. The selectivity assessed the efficiency of the extraction solvent, demonstrating the ease of solute extraction. In Figure 9, it was possible to observe that the selectivity diminished gradually with the increase of the CPO concentration using the aforementioned two solvents at a certain temperature. In the meantime, the selectivity decreased with the increasing temperature, the order of which was S308.2 K > S318.2 K > S328.2 K, indicating that the lower temperature was preferable. As presented in Tables 2 and 3, the values of the distribution parameter as well as


respectively, the mole fraction of cyclopentanone in the above two phases. In both ternary systems, the values of D and S are also presented in Tables 2 and 3. As shown in Tables 2 and 3, the distribution parameters increased with increasing CPO concentration in the water phase when methylcyclohexane was used as the extractant. Simultaneously, for the temperature effect, the selectivity regarding the mixtures of water + cyclopentanone + methylcyclohexane and water + cyclopentanoefne + propyl acetate is illustrated in Figure 9. It can be C



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Figure 7. Effect of temperature on the phase equilibrium behavior for the water (1) + cyclopentanone (2) + methylcyclohexane (3) system.

Figure 4. Ternary phase diagram for the water (1) + cyclopentanone (2) + propyl acetate (3) system at 308.2 K and 101.3 kPa: (*) experimental data; (☆) feed composition; (△) NRTL model; and (●) UNIQUAC model.

Figure 8. Effect of temperature on the phase equilibrium behavior for the water (1) + cyclopentanone (2) + propyl acetate (3) system. Figure 5. Ternary phase diagram for the water (1) + cyclopentanone (2) + propyl acetate (3) system at 318.2 K and 101.3 kPa: (*) experimental data; (☆) feed composition; (△) NRTL model; and (●) UNIQUAC model.

Figure 9. Experimental selectivity versus mole fraction of cyclopentanone in the aqueous phase at 101.3 kPa. (■) Methylcyclohexane 308.2 K; (red ●) methylcyclohexane 318.2 K; (blue ▲) methylcyclohexane 328.2 K; (pink ▼) propyl acetate 308.2 K; (green ⧫) propyl acetate 318.2 K; and (gray ★) propyl acetate 328.2 K.

Figure 6. Ternary phase diagram for the water (1) + cyclopentanone (2) + propyl acetate (3) system at 328.2 K and 101.3 kPa: (*) experimental data; (☆) feed composition; (△) NRTL model; and (●) UNIQUAC model.

selectivity regarding the adopted two solvents were all greater than 1, which suggested that it was feasible to recover CPO D



Article

Table 4. Bachman and Hand Equation Parameters and Regression Coefficients (R2) for the Water (1) + Cyclopentanone (2) + Solvents (3) System at Different Temperaturesa Bachman equation

Hand equation

solvent

T (K)

a

b

R2

c

d

R2

methylcyclohexane

308.2 318.2 328.2 308.2 318.2 328.2

−0.0404 −0.0362 −0.0297 −0.0154 −0.0129 −0.0101

1.0336 1.0304 1.0239 1.0049 1.0069 1.0036

0.9997 0.9998 0.9998 0.9999 0.9999 0.9999

5.0296 5.0584 5.4624 4.4473 4.6564 4.8941

1.5943 1.5546 1.6104 1.2101 1.2072 1.2397

0.9800 0.9819 0.9796 0.9971 0.9939 0.9954

propyl acetate

a 2

R is the correlation coefficient of Bachman and Hand equations.

Figure 11. Hand plots for the ternary systems at T = 308.2, 318.2, and 328.2 K. (a) Water + cyclopentanone + methylcyclohexane system and (b) water + cyclopentanone + propyl acetate system. (red ▲) 308.2 K; (blue ●) 318.2 K; and (■) 328.2 K.

Figure 10. Bachman plots for ternary systems at T = 308.2, 318.2, and 328.2 K. (a) Water + cyclopentanone + methylcyclohexane system and (b) water + cyclopentanone + propyl acetate system. (red ▲) 308.2 K; (blue ●) 318.2 K; and (■) 328.2 K.

ÄÅ I ÉÑ ÄÅ II ÉÑ ÅÅ x ÑÑ ÅÅ x ÑÑ Å Ñ 2 lnÅÅÅ I ÑÑÑ = c + lnÅÅÅÅ 2II ÑÑÑÑ ÅÅ x3 ÑÑ ÅÅ x1 ÑÑ ÅÇ ÑÖ Ç Ö

from water utilizing the above extractants. Given greater selectivity of the ternary systems, methylcyclohexane as an extractant is more suitable for separating the CPO + water mixture in the low concentration region than propyl acetate. Estimation of Experimental Values. The reliability of the ternary tie-line results was fitted using the Bachman empirical equation17 and Hand empirical equation,18 respectively x3I = a + b[x3I/x1II]

(7)

Here a, b, c, and d denote the fitting parameters of eqs 6 and 7.While xI2 and xI3 denote the related concentrations of CPO and solvents in the upper layer, and xII1 and xII2 denote the related concentrations of water and CPO in the lower layer, respectively. In this article, the values of a, b, c, and d are summarized in Table 4, while the linear diagrams plotted by the Bachman and Hand empirical equations are presented in Figures 10 and 11,

(6) E



Article

The consistency among the experimental and correlating LLE values was determined via the corresponding root-meansquare deviation (rmsd %) value,29,30 as described in eq 9.

respectively. Both plots show a linear behavior, with the Bachman and Hand correlation cofficients (R2) being close to 1, which indicated the satisfactory reliability of our experimental values. Modeling LLE Values. The NRTL19 and UNIQUAC20 models were utilized for correlating the experimental results via Aspen Plus (software 8.4). With regard to the UNIQUAC model, the structural parameters (r and q) of the pure components are, respectively, measures of the molecular-geometric volume and molecular-geometric area. These values of water, cyclopentanone, methylcyclohexane, and propyl acetate have be reported in the literature,12,26,27 and are listed in Table 5. In the NRTL model, the nonrandomnes

1/2 M 2 3 l o o (xlmn − xlmn ̂ )2 | o o rmsd% = 100m } ∑∑∑ o o o o 6M n n=1 m=1 l=1 ~

where arguments M, x, x̂, l, m, and n were identical to those in the eq 8. The results of rmsd % regarding the studied ternary mixtures are tabulated in Table 6. It was clear that all rmsd % values were between 0.16 and 0.71, as shown in Table 6, demonstrating that both thermodynamic models can provide reasonable and accurate predictions for simulated experimental data. Moreover, as plotted in Figures 1−6, a satisfactory coincidence can be achieved among the experimental and correlating values.

Table 5. UNIQUAC Structural Parameters component

r

q

double-distilled water cyclopentanone methylcyclohexane propyl acetate

0.92a 3.03a 3.92b 3.19c

1.40a 2.44a 2.97b 2.40c

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CONCLUSIONS This study revealed the phase equilibrium values regarding the ternary mixtures of water + cyclopentanone + methylcyclohexane or propyl acetate at 308.2, 318.2, and 328.2 K and 101.3 kPa. The obtained results revealed that all values of D and S were much larger than 1, and methylcyclohexane appeared to increase the values of the selectivity, indicating that methylcyclohexane could be the most suitable solvent. The reliability of the experimental values was tested utilizing the Bachman and Hand empirical equations, and the results indicated that the experimental data were reliable. The comparative results of rmsd % revealed that the NRTL model was more appropriate than the UNIQUAC models in the above ternary systems. Moreover, our study indicated the promising of recovery CPO from wastewater employing a solvent extraction.

a

From ref 14. bFrom ref 26. cFrom ref 27.

parameter αij was commonly in the range of 0.2−0.47.28 The regression parameters of the above two methods could be obtained via minimizing the difference squared between the phase equilibrium compositions. The composition objective function (OF) was calculated according to M

OF =

2

3

̂ − xlmn ̂ )2 ∑ ∑ ∑ (xlmn

(8)

n=1 m=1 l=1

(9)

where M refers to the number of tie-lines, and x and x̅ denote, respectively, the experimental and calculated values. The parameters n, m, and l represent, respectively, the tie-line, phase, and component. The optimized binary interaction energy parameters for the immiscible mixture are summarized in Table 6. The LLE results calculated with both models are also plotted in Figures 1−6.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected].

Table 6. Binary Interaction Parameters of NRTL and UNIQUAC Models for the Water (1) + Cyclopentanone (2) + Solvents (3) System at Different Temperatures NRTL parameters

UNIQUAC parameters

solvent

T (K)

i−j

gij−gjj (J/mol)

gji−gii (J/mol)

α

methylcyclohexane

308.2

1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3 1−2 1−3 2−3

4847.19 19027.83 3226.03 4287.28 20175.65 7159.07 5571.75 20442.54 3750.60 8670.27 10029.09 4364.50 9097.35 12352.74 3035.85 10666.55 12949.71 2963.23

4767.06 11447.65 81.16 4669.84 12119.98 −2986.70 4490.28 11488.58 −690.41 −539.94 2475.21 −2922.01 −256.45 1172.59 −2105.12 −1302.90 820.20 −1875.04

0.2 0.2 0.3 0.2 0.2 0.3 0.2 0.2 0.3 0.2 0.2 0.3 0.2 0.2 0.3 0.2 0.2 0.3

318.2

328.2

propyl acetate

308.2

318.2

328.2

rmsd (%) 0.33

0.43

0.20

0.20

0.38

0.39

uij−ujj (J/mol)

uji−uii (J/mol)

−1225.15 2059.72 1706.42 −1666.25 2141.97 3037.86 −1504.79 2250.62 2481.91 −1258.79 304.50 1940.46 −1622.00 702.83 1615.38 718.33 930.76 143818.96

6115.18 8837.28 −497.91 6891.73 9047.86 −1219.91 6735.65 8904.92 −833.26 4098.41 4614.85 −1385.16 7031.47 3630.35 −1271.61 3771.71 5925.85 −510.19

rmsd (%) 0.69

0.71

0.68

0.16

0.47

0.40

a

Here g and u are the interaction parameters of NRTL and UNIQUAC models, respectively. F



Article

ORCID

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Qingsong Li: 0000-0003-1425-8822 Notes

The authors declare no competing financial interest.

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REFERENCES

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