LiquidâLiquid Equilibrium of Isobutyl Acetate + Isobutyl Alcohol +

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

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Liquid−Liquid Equilibrium of Isobutyl Acetate + Isobutyl Alcohol + Imidazolium-Based Ionic Liquids at 298.15 and 308.15 K Xianglin Meng,† Xiaowei Liu,† Jun Gao,† Dongmei Xu,*,† Lianzheng Zhang,† and Yinglong Wang‡ †

College of Chemical and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590, China College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China

‡

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S Supporting Information *

ABSTRACT: For separation of the azeotrope isobutyl acetate and isobutyl alcohol, imidazolium-based ionic liquids 1-hexyl-3-methylimidazolium hexafluorophosphate [Hmim][PF6] and 1-octyl-3-methylimidazolium hexafluorophosphate [Omim][PF6] were applied as the extractants in the extraction process. The liquid−liquid equilibrium (LLE) data for the ternary systems isobutyl acetate + isobutyl alcohol + ([Hmim][PF6]/[Omim][PF6]) were determined at temperature of 298.15 and 308.15 K. To evaluate extraction performance of the ILs, the selectivity and distribution coefficient were calculated from the experimental data. The effect of the alkyl chain length of the cations and the temperature on the LLE for the systems were explored. In addition, the experimental LLE data were correlated by the NRTL model, and the binary interaction parameters of the NRTL model were optimized.

1. INTRODUCTION Isobutyl acetate (IBAC) is an important chemical solvent, which is widely used in chemical industry.1 Usually, IBAC can be prepared by esterification of acetic acid with isobutyl alcohol (IBA).2 Since IBAC can form a minimum boiling point azeotrope with IBA,3 IBAC cannot be separated from the reaction mixture by conventional distillation. Generally, to separate azeotropic mixtures, some special distillation technologies are required, such as extractive distillation,2,4−6 pressure-swing distillation,2,7 azeotropic distillation.8,9 In addition, liquid−liquid extraction10−14 is also often used to separate the azeotrope because of its ability to save energy. As for the extractants of liquid−liquid extraction, recently, ionic liquids as a kind of new environmentally friendly green solvents are often considered to be the alternatives to replace traditional organic solvents because of their advantages, including low-volatility, thermal stability, and designability.15−19 However, to our knowledge, no literatures have reported the liquid−liquid phase equilibrium for the ternary systems of IBAC + IBA + ILs until now. Cháfer et al.20 reported the liquid−liquid equilibrium data for the system (IBAC + IBA + water/glycerol). Bai et al.21 determined isobaric VLE data for the system (IBAC + IBA + N, Ndimethylacetamide). Munoz et al.2 separated the azeotrope of (IBA + IBAC) by extractive distillation and pressure-swing distillation. In this work, two imidazolium-based ionic liquids [Hmim][PF6] and [Omim][PF6] were selected to separate the azeotrope of IBAC and IBA. The LLE data for the ternary systems (isobutyl acetate + isobutyl alcohol + [Hmim][PF6]) and (isobutyl acetate + isobutyl alcohol + [Omim][PF6]) were determined. The tie-line data were fitted by the NRTL model. © XXXX American Chemical Society

The influence of the alkyl chain length of cation on the extraction performance was explored on the basis of the distribution and selectivity coefficient.

2. EXPERIMENTAL SECTION 2.1. Chemicals. The chemical reagents used in this work were all purchased commercially and the purities of the chemicals IBAC, IBA, [Hmim][PF6], and [OmimPF6]) are 0.997, 0.995, and 0.98/0.98, respectively. To remove the trace moisture in the ionic liquids, the ionic liquids were dried at 363.15 K under 20 kPa in a vacuum drying oven before used. The structures of the cations and anion of the selected ILs are presented in Table 1, and the detailed information on chemicals is listed in Table 2. 2.2. Apparatus and Procedure. For the LLE measurement, the procedures were reported in our previous work.22 Table 1. Relevant Information of ILs Cations and Anion

Received: November 6, 2018 Accepted: January 10, 2019

A

DOI: 10.1021/acs.jced.8b01045 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 2. Relevant Information of Chemicals name

CAS

isobutyl acetate

110-19-0

isobutanol

78-83-1

[Hmim] [PF6]

304680-35-1

[Omim] [PF6]

304680-36-2

suppliers Shanghai Macklin Biochemical Co., Ltd. Shanghai Sinopharm Chemical Reagent Co., Ltd. Lanzhou Zhongke Ketko Industry & Trade Co., Ltd. Lanzhou Zhongke Ketko Industry & Trade Co., Ltd.

mass purity

analysis method

≥0.997b

GCa

≥0.995

b

Table 3. Experimental LLE Data (Mole Fraction), Distribution Coefficient (D), Selectivity (S) for the Ternary System (IBAC + IBA + [Hmim][PF6]) in Different Temperature (298.15 and 308.15 K) under 101.3 kPaa

a

T/K

GC

IBA-rich phase

IL-rich phase

xI1

xI2

xII1

IBAC (1) 0.6410 0.7018 0.7526 0.8001 0.8467 0.8832 0.9230 0.9641 0.9985 IBAC (1) 0.6292 0.6945 0.7491 0.8013 0.8456 0.8864 0.9266 0.9627 0.9922

+ IBA (2) 0.3435 0.3065 0.2649 0.2273 0.1811 0.1434 0.1058 0.0494 0.0000 + IBA (2) 0.3485 0.3001 0.2611 0.2188 0.1725 0.1312 0.0959 0.0487 0.0000

298.15 ≥0.980b

GCa

≥0.980b

GCa

0.3402 0.2882 0.2403 0.1952 0.1500 0.1143 0.0753 0.0346 0.0000

a

Gas chromatography. bAnalysis by the suppliers.

For the mixture preparation, to cover the entire two-phase region, the mass of IL was kept unchanged, the mass of ester was increased, and that of the alcohol was correspondingly reduced. After that, the equilibrium cell with the prepared mixture was placed in a thermostatic water bath (DF-101S, Jintan Xinbao electronic equipment Co., Ltd.). The mixture was vigorously stirred at least 4 h to make the component contact intimately and then settled for 16 h to obtain the equilibrium state. During the settlement, any disturbance should be avoided. Then, the samples from the upper layer (IBAC rich phase) and lower layer (IL rich phase) were withdrawn by syringe, respectively, and the samples were analyzed by GC at least three times. 2.3. Analysis. The sample compositions were analyzed by GC (Lunan GC SP-6890), which was equipped with a Headspace Autosampler (AHS-6890A, Beijing Zhongyiyusheng Technology Co., Ltd.), a packed column (Porapak Q 3 mm × 2 m), and a TCD detector. The peak area of the samples was analyzed by the N2000 chromatography workstation, which was developed by Zhengjiang University. Before analyzing the samples, a series of different standard mixtures was used to calibrate GC, which was prepared by an analytical balance (AR124CN, Changzhou Aohaosi, China). The purity of hydrogen as a carrier gas was 99.999%. The analysis temperatures are as follows: oven temperature, 473.15 K, detector temperature, 463.15 K, and injection temperature, 473.15 K. For the analysis of the selected ILs, the gravimetric method was used to determine the content of the ILs in the samples.23

308.15 0.3489 0.2868 0.2400 0.1910 0.1486 0.1104 0.0705 0.0353 0.0000

xII2

S

D

+ [Hmim][PF6] (3) 0.4102 1.5778 0.3856 1.9355 0.3781 2.1943 0.3726 2.5001 0.3720 2.7482 0.3578 3.0967 0.3559 3.6422 0.3378 4.0664 0.3305 + [Hmim][PF6] (3) 0.4450 1.4123 0.4380 1.6596 0.4346 1.8760 0.4250 2.1600 0.4141 2.3704 0.4090 2.5743 0.3988 3.1603 0.3996 3.3201 0.3885

1.0097 1.0635 1.1025 1.1642 1.2073 1.2545 1.4043 1.4247

0.9988 1.0467 1.0883 1.1455 1.1607 1.1879 1.3600 1.3781

a Standard uncertainties: u(T) = 0.05 K, u(p) = 0.1 kPa, and u(x) = 0.0124.

Table 4. Experimental LLE Data (Mole Fraction), Distribution Coefficient (D), Selectivity (S) for the Ternary System (IBAC + IBA + [Omim][PF6]) in Different Temperature (298.15 and 308.15 K) under 101.3 kPaa T/K

IBA-rich phase

IL-rich phase

xI1

xII1

298.15 0.1563 0.1298 0.1106 0.0896 0.0702 0.0532 0.0340 0.0169 0.0000

3. RESULTS AND DISCUSSION 3.1. LLE Experimental Data. The LLE experimental data for the systems (IBAC + IBA + [Hmim][PF6]) and (IBAC + IBA + [Omim][PF6]) were determined at 298.15 and 308.15 K under 101.3 kPa, which are listed in Tables 3 and 4. Additionally, the feed compositions in the experiments are listed in Tables S1 and S2 in the Supporting Information. The subscripts 1, 2, and 3 refer to IBAC, IBA, and ILs, and superscripts I and II represent the upper phase and lower phase, respectively. To explore the phase behavior of the ternary systems, the LLE data were plotted in Figures 1−4. As shown in Figures 1−4, the phase behavior of the two ternary systems belongs to Treybal’s type I,24 where only two components were partially miscible. For the investigated ternary systems, IBA and ILs are partially miscible. 3.2. Distribution Coefficient and Selectivity. For liquid−liquid extraction, the distribution coefficient can

308.15 0.1272 0.1211 0.1113 0.0935 0.0730 0.0535 0.0340 0.0197 0.0000

xI2

xII2

S

IBAC (1) + IBA (2) + [Omim][PF6] (3) 0.8239 0.1885 0.5860 1.695 0.8590 0.1691 0.5738 1.951 0.8813 0.1501 0.5555 2.152 0.9048 0.1255 0.5421 2.338 0.9255 0.1039 0.5255 2.605 0.9434 0.0813 0.5153 2.794 0.9633 0.0550 0.5076 3.068 0.9810 0.0292 0.4994 3.399 0.9949 0.0000 0.4916 IBAC (1) + IBA (2) + [Omim][PF6] (3) 0.8337 0.1477 0.6877 1.407 0.8464 0.1457 0.6564 1.520 0.8686 0.1425 0.6377 1.745 0.8924 0.1235 0.6265 1.881 0.9173 0.1034 0.6088 2.134 0.9399 0.0784 0.5872 2.345 0.9612 0.0522 0.5770 2.561 0.9762 0.0319 0.5720 2.759 0.9920 0.0000 0.5703

D 1.205 1.303 1.357 1.401 1.479 1.526 1.617 1.730

1.160 1.177 1.281 1.320 1.416 1.464 1.537 1.616

a

Standard uncertainties: u(T) = 0.05 K, u(p) = 0.1 kPa, and u(x) = 0.0124.

represent the extractant dosage, and the selectivity is often used to describe the extraction ability in the extraction process. To evaluate the extraction ability of the selected ILs, the B



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Figure 1. Phase diagram for the ternary mixture IBAC (1) + IBA (2) + [Hmim][PF6] (3) at T = 298.15 K: (■ - ■), experimental tie-line data; (○ -- ○), NRTL calculation results

Figure 3. Phase diagram for the ternary mixture IBAC (1) + IBA (2) + [Omim][PF6] (3) at T = 298.15 K: (■ - ■), experimental tie-line data; (○ -- ○), NRTL calculation results.

Figure 2. Phase diagram for the ternary mixture IBAC (1) + IBA (2) + [Hmim][PF6] (3) at T = 308.15 K: (■ - ■), experimental tie-line data; (○ -- ○), NRTL calculation results.

Figure 4. Phase diagram for the ternary mixture IBAC (1) + IBA (2) + [Omim][PF6] (3) at T = 308.15 K: (■ - ■), experimental tie-line data; (○ -- ○), NRTL calculation results.

distribution coefficient and selectivity of IBAC were calculated from the LLE data. The distribution coefficient and selectivity are expressed as follows:25,26 D=

S=

distribution coefficient and selectivity, the diagrams of the distribution coefficient and selectivity versus the concentration of IBAC in the IBAC rich phase are plotted in Figures 5 and 6, respectively. From Figures 5 and 6, as the temperature increases, the distribution coefficient and selectivity decrease slightly, Meanwhile, in Figures 1−4, as the solubility increases with the temperature increasing, the area of the heterogeneous region in the ternary phase diagrams decreased. Xu et al.27 explored the LLE for (water +2-Propanol + [Dmim][NTf2]) at different temperatures. In their work, the experimental results indicate that two-phase region also decreased with the increasing temperature. Also, as shown in Figure 6, the extraction ability of the selected ILs follows the order: [Hmim][PF6] > [Omim][PF6], which indicates that the shorter alkyl chain of the cation, the stronger the extraction ability of the ionic liquid, which is consistent with the results

x1II x1I

(1)

(x1II/x1I)

xI1

x 2II/x 2I

(2)

xII1

where and refer to the mole fraction of IBAC in IBACrich phase and IL-rich phase, respectively; xI2 and xII2 refer to the mole fraction of IBA in IBAC-rich phase and IL-rich phase. The calculated results of D and S are listed in Tables 3 and 4. All the values of S in each system are greater than 1, which indicates that the selected ionic liquids are capable of separating IBAC and IBA. To illustrate the change of the C



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group of IBA and increases the mutual solubility between ionic liquid and IBA.31 3.3. Data Correlation. To correlate the LLE experiment data containing ILs, the NRTL model32 has been applied by the researchers.33−36 The model is presented as follows: ÄÅ ÉÑ ∑j τjiGjixj ∑l xlτljGlj ÑÑÑ xjGij ÅÅÅ Å ÑÑ ÅÅτij − lnγi − +∑ Å ÑÑ ∑ ∑k Gkixk ∑ G x G x Å ÑÖ k kj k Ñ k kj k Å j (3) Ç Gij = exp( −ατij) τij =

(4)

Δgij (5)

RT

where xi refers to the mole fraction of component i, T is the experimental temperature, γi refers to the activity coefficient of component i, and Δgij is the binary parameter, α is nonrandomness parameter and is fixed to 0.3. To correlate the LLE data and regress the binary parameters, the objective function was used and is expressed as follows:

Figure 5. Distribution coefficient (D) plots against with the mole fraction of IBAC in the upper phase (xI1): [Hmim][PF6], (●), 298.15K; [Hmim][PF 6 ], (○), 308.15K; [Omim][PF6], (■), 298.15K; [Omim][PF6], (□), 308.15K].

M

OF =

2

3

∑ ∑ ∑ (xijkexp − xijkcal)2 (6)

k=1 j=1 i=1 exp

cal

where x and x indicate experimental data and calculated results, M refers to the number of tie-lines, and the subscripts i, j, and k represent the component, phase, and tie-line, respectively. To access the correlation performance by the NRTL model, the root-mean-square deviation (RMSD) was often used as evaluation criteria in many literatures37−39 and is expressed as follows: ÄÅ É ÅÅ M 2 3 (x exp − x cal)2 ÑÑÑ1/2 ÅÅ ÑÑ ijk ijk ÑÑ RMSD = ÅÅÅ∑ ∑ ∑ ÑÑ ÅÅ 6 M ÅÇÅ k = 1 j = 1 i = 1 ÑÑÖÑ (7) The regressed parameters of NRTL model and the value of the RMSD for the ternary systems are listed in Table 5. The Table 5. Regressed Values of Binary Parameters and RMSD binary interaction parameters i−j

Figure 6. Selectivity (S) plots against with the mole fraction of IBAC in the upper phase (xI1): [Hmim][PF6], (●), 298.15K; [Hmim][PF6], (○), 308.15K; [Omim][PF6], (■), 298.15K; [OmimPF6], (□), 308.15K.

1−2 1−3 2−3

reported in the literatures. Xu et al.28 adopted [Bmim][PF6] and [Hmim][PF6] to extract n-propyl acetate from the mixture of (n-propyl acetate + n-propanol) and n-butyl acetate from the mixture of (n-butyl acetate + n-butanol) respectively. The experimental results indicate that the shorter alkyl chain of cation is favorable to separate esters from the mixtures. Pereiro et al.29 separated the azeotrope of (ethyl acetate +2-propanol) by imidazolium-based ionic liquids with [PF6]−, and concluded that the shorter alkyl chain of cation is helpful to extract ethyl acetate from the azeotrope. The reason causing the phenomenon maybe is that the nonpolarity of [Omim][PF6] is stronger than [Hmim][PF6] due to its longer alkyl chain length. Thus, the alkyl group of IBA can form the stronger van der Waals interactions with the cation of [Omim]− compared to [Hmim]−,29,30 which decreases the polarity of the −OH

1−2 1−3 2−3

Δgij(kJ·mol−1)

Δgji(kJ·mol−1)

IBAC (1) + IBA (2) + [Hmim][PF6] −2.0981 −3.7968 7.6605 −1.2936 11.4711 30.8732 IBAC (1) + IBA (2) + [Omim][PF6] 2.7296 −5.0636 3.1041 −5.6229 14.5653 −0.5857

α

RMSD

(3) 0.3

0.0336

(3) 0.0211 0.3

values of RMSD are less than 0.034, which indicates that the correlated results by the NRTL model are in agreement with the experimental data. Meanwhile, for comparison, the calculated results are also plotted in Figures 1−4.

4. CONCLUSIONS In this work, to separate the azeotrope of IBAC and IBA, two imidazolium-based ionic liquids [Hmim][PF6] and [Omim][PF6] were selected as the extractants. The LLE data for the ternary systems of (IBAC + IBA + [Hmim][PF6]) and (IBAC D



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+ IBA + [Omim][PF6]) were determined at 298.15 and 308.15 K under 101.3 kPa. The phase diagrams for the ternary systems belong to Treybal’s typeI. The distribution coefficient and selectivity were calculated. All the values of the selectivity are all greater than unity, which indicates the separation of the azeotrope of IBAC and IBA by the ILs is feasible. As the temperature and the alkyl chain length of the cation increase, the extraction ability of the ionic liquids slightly decreases. [Hmim][PF6] shows the best extraction ability compared to [Omim][PF6]. The LLE experimental data were correlated by NRTL model, and the values of RMSD are less than 0.034, which indicates that the NRTL model can well correlate the LLE experimental data.

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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.8b01045.

■

Feed compositions (mole fraction) for the system IBAC (1) + IBA (2) + ILs (3) (PDF)

AUTHOR INFORMATION

Corresponding Author

*Tel.: +86 532 86057798; E-mail: [email protected]. ORCID

Jun Gao: 0000-0003-1145-9565 Dongmei Xu: 0000-0002-5770-0513 Yinglong Wang: 0000-0002-3043-0891 Notes

The authors declare no competing financial interest.

■

ACKNOWLEDGMENTS This work was supported by the National Natural Science Foundation of China (Grant 21878178), Shandong Provincial Key Research & Development Project (2018GGX107001) and A Project of Shandong Province Higher Educational Science and Technology Program (J18KA072).

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REFERENCES

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