Article pubs.acs.org/jced
Vapor Pressure Measurement and Isobaric Vapor−Liquid Equilibria for Binary Mixtures of ZE-2-Methyl-2-butenenitrile and 2‑Methyl-3butenenitrile Yu Cao,† Xuezhi Dai,‡ Hang Song,‡ Shun Yao,‡ and Xianqiu Lan*,‡ †
College of Life Science & Biotechnology, Mianyang Normal University, Mianyang 621000, China School of Chemical Engineering, Sichuan University, Chengdu 610065, China
‡
ABSTRACT: Vapor−liquid equilibrium (VLE) at P = 50.0 and 100.0 kPa have been determined for the binary system (ZE-2-methyl-2-butenenitrile + 2-methyl-3-butenenitrile). To analyze the binary data, the vapor pressures of ZE-2-methyl-2butenenitrile and 2-methyl-3-butenenitrile were determined, and the experimental values were correlated using an Antoinetype equation. The vapor pressures predicted by the Antoine equation had average relative deviations of 1.964% and 0.907% from the experimental values for ZE-2-methyl-2-butenenitrile and 2-methyl-3-butenenitrile, respectively. Thermodynamic consistency tests were performed for all of the VLE data using the point test, area test, and direct test, and all of the data passed the three tests. The VLE binary data were all calculated from activity coefficients correlated using the Wilson and NRTL models. The model parameters were obtained, and all of the models represent the experimental values quite well.
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INTRODUCTION The large-scale production of adiponitrile (AdN) has been an important catalytic industrial process since the discovery of Nylon-66, and 2-methyl-3-butenenitrile is a key intermediate in the catalytic process.1 Moreover, 2-methyl-3-butenenitrile was proved to be an excellent reaction reagent in some special chemical syntheses.2 In the case of 2-methyl-3-butenenitrile, the π-methylallyl metal complex was observed in solution. ZE-2Methyl-2-butenenitrile, the isomer of 2-methyl-3-butenenitrile, is thought to be a new intermediate in the biosynthesis of rhodiocyanosides.3 In some special applications, high purity of 2-methyl-3-butenenitrile or ZE-2-methyl-2-butenenitrile is needed. However, 2-methyl-3-butenenitrile can be converted to ZE-2-methyl-2-butenenitrile by a catalytic reaction. The 2methyl-3-butenenitrile product usually contains ZE-2-methyl-2butenenitrile, and the same problem exists in the ZE-2-methyl2-butenenitrile product. The binary mixture limits its application in several fields. Therefore, finding a separation method for this binary mixture that can be used in large-scale industrial production is necessary. Distillation, a traditional separation method, exhibits its superiority compared with other separation methods, especially in achieving economies of largescale industrial operation. The distillation method requires reliable knowledge of the vapor pressures of the pure compounds and vapor−liquid equilibrium (VLE) data, but VLE data for the binary system (ZE-2-methyl-2-butenenitrile + 2-methyl-3-butenenitrile) as well as the integrated vapor pressures of these pure components have not been reported to date. Only limited information has been reported, such as a © XXXX American Chemical Society
few boiling temperatures of ZE-2-methyl-2-butenenitrile (1 atm and 7 Torr)4,5 and 2-methyl-3-butenenitrile (only at 1 atm).6 In this work, the pure-component vapor pressures of ZE-2methyl-2-butenenitrile and 2-methyl-3-butenenitrile and the isobaric VLE data for the related binary system were measured and correlated. The measurement and correlation can provide important reference data for theoretical research and industrial applications.
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EXPERIMENTAL SECTION Chemicals. The chemicals ZE-2-methyl-2-butenenitrile and 2-methyl-3-butenenitrile were both obtained commercially (Chongqing Unisplendour Chemical Co., Ltd.) and then purified by rectification with about 100 theoretical plates in our laboratory before use. The specifications of the chemicals used are listed in Table 1. Apparatus and Procedure. The vapor pressure apparatus described in our previous work7 was employed in the experiment. It contains a stainless steel vapor−liquid balancing still, a pressure transmitter, a data acquisition system, an operation desk, and a 2XZ-4 vacuum pump and was designed by our lab for use in measuring VLE data. The procedure was the same as in our recent publication7 and was checked again with satisfactory results. A schematic representation and Received: November 9, 2015 Accepted: March 17, 2016
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DOI: 10.1021/acs.jced.5b00943 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Table 1. Specifications of the Chemical Samples compound
CAS no.
initial mass-fraction purity
purification method
final mass-fraction purity
analysis method
ZE-2-methyl-2-butenenitrile 2-methyl-3-butenenitrile
4403-61-6 16529-56-9
0.7686 0.9163
rectification rectification
0.955 0.994
gas chromatography gas chromatography
Table 2. Experimental Vapor Pressures of ZE-2-Methyl-2-butenenitrile and 2-Methyl-3-butenenitrilea ZE-2-methyl-2-butenenitrile
a
2-methyl-3-butenenitrile
T/K
Pexpt/kPa
T/K
Pexpt/kPa
T/K
Pexpt/kPa
T/K
Pexpt/kPa
294.11 298.30 304.65 311.10 314.64 319.36 325.87 330.26 333.50 339.65 344.85 347.25
2.658 3.391 4.671 6.157 7.224 8.987 11.654 14.720 16.187 20.709 22.979 25.246
351.09 354.46 357.95 362.37 366.05 370.15 374.68 378.35 381.63 385.89 388.85 396.65
28.579 32.179 36.312 42.044 46.454 52.987 61.120 69.652 74.585 83.651 91.650 103.516
297.57 304.35 309.86 315.95 318.68 321.34 324.85 327.15 331.76 335.25 339.53 343.65
2.701 3.664 4.608 6.064 6.731 7.521 8.987 9.900 11.747 13.480 15.747 18.680
352.65 356.05 359.56 364.85 369.25 373.25 376.09 379.75 382.83 387.65 391.95 394.25
25.346 29.212 33.212 38.545 44.678 50.010 55.477 62.676 68.942 79.228 90.160 95.760
The standard uncertainties u are u(T) = 0.01 K and ur(P) = 0.01.
Table 3. Coefficients Used To Calculate Pi° for the Pure Components relative deviation/% compound
A
B
C
mean
max
min
ZE-2-methyl-2-butenenitrile 2-methyl-3-butenenitrile
13.3290 16.6900
2945.3800 5136.4220
−55.1120 29.3300
1.964 0.907
6.758 2.513
0.059 0.022
was produced by an SPGH-300 hydrogen generator with a flow rate of 20 mL·min−1, and the flow rate of air was 150 mL·min−1. The column, injector, and detector temperatures for the binary systems were 363, 473, and 473 K, respectively. Very good peak separation was achieved under these conditions, and calibration analyses were carried out to convert the peak-area ratio to the mass composition of the sample. The average absolute deviation in the mole fraction was usually less than 0.001. At least three measurements were performed for each composition, and the average values are given in the following tables.
detailed description of the apparatus structure were provided in our previous paper.7 Temperature control for the still included two parts: a constant-temperature magnetic stirrer (Shanghai Sile Instrument Co., Ltd., China) for coarse adjustment of the temperature and a resistance wire winding around the still for fine adjustment of the temperature, which could ensure homogeneous steady heating. A mercury-in-glass thermometer with a standard uncertainty of 0.01 K was applied to record the temperatures. The pressure data were acquired using a pressure transmitter (Beijing Collihigh Sensing Technology Co., Ltd., China) with a relative standard uncertainty of 0.01 and the data acquisition system in the operation desk. In the measurements of isobaric VLE data, a mixture sample of desired proportions was prepared and injected into the vessel from the inlet with a syringe. The following experiments were performed under a dried inert air atmosphere at a constant pressure of 50 or 100 kPa. Under constant pressure, equilibrium conditions were assumed when a constant temperature was observed and kept for 15 min or longer. About 1.5 mL of the vapor and liquid samples were taken from the condensate and liquid outlets with syringes at almost the same time for GC analysis, and the temperature was recorded simultaneously. Analysis. Compositions of the liquid and vapor phases were determined using a GC7900 gas chromatograph with a flame ionization detector (FID), a TM-1701 capillary column (column length 30 m, diameter 0.32 mm), and a D-7900P chromatographic workstation (Shanghai Techcomp Instrument Co., Ltd., China). n-Propanol was used as an external standard for peak-area quantification. The carrier gas was high-purity nitrogen at a constant flow rate of 50 mL·min−1. The hydrogen
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RESULTS AND DISCUSSION
Pure-Component Vapor Pressures. The pure-component vapor pressures (P°) of ZE-2-methyl-2-butenenitrile and 2-methyl-3-butenenitrile were determined experimentally over the temperature ranges 294.11−396.65 K and 297.57−396.40 K, respectively. The pertinent results appear in Table 2. The measured vapor pressures were correlated using the Antoine equation: ln(Pi°/kPa) = Ai −
Bi T /K + Ci
(1)
The Antoine parameters Ai, Bi, and Ci calculated from the experimental data in Table 2 are collected in Table 3. The parameters were calculated by the multiple linear regression method using the experimental vapor pressure data. The relative deviations [(Pexpt − Pcalc)/Pexpt] × 100% for the pressures calculated by means of the Antoine equation using the values of the constants shown in Table 3 were also studied. The mean relative deviations between the vapor pressures calculated using the Antoine equation and the experimental B
DOI: 10.1021/acs.jced.5b00943 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Table 4. VLE Data for the Binary System ZE-2-Methyl-2-butenenitrile (1) + 2-Methyl-3-butenenitrile (2) at 50.0 and 100.0 kPaa P/kPa
T/K
x1
y1
γ1
γ2
GE/RT
ΔTb/K
Δy1b
ΔTc/K
Δy1c
50.0
371.85 371.45 370.85 370.35 369.85 369.45 368.95 368.75 368.15 395.25 395.00 394.65 394.35 394.05 393.80 393.50 393.20 393.00
0.1241 0.2124 0.3297 0.4180 0.5145 0.5961 0.7059 0.7524 0.8879 0.1246 0.2139 0.3269 0.4211 0.5078 0.5867 0.6878 0.7982 0.8879
0.1659 0.2575 0.3723 0.4553 0.5449 0.6209 0.7239 0.7672 0.8949 0.1497 0.2429 0.3534 0.4414 0.5231 0.5987 0.6947 0.8001 0.8889
1.1882 1.0903 1.0337 1.0119 0.9986 0.9939 0.9933 0.9935 0.9999 1.1264 1.0715 1.0292 1.0056 0.9959 0.9929 0.9903 0.9905 0.9943
0.9767 0.9793 0.9917 1.0071 1.0251 1.0398 1.0569 1.0654 1.0833 0.9839 0.9825 0.9898 1.0028 1.0157 1.0251 1.0414 1.0640 1.0707
0.0007 0.0019 0.0053 0.0091 0.0113 0.0121 0.0115 0.0108 0.0089 0.0006 0.0009 0.0025 0.0040 0.0056 0.0061 0.0060 0.0049 0.0026
0.16 0.35 0.45 0.41 0.36 0.31 0.22 0.18 −0.01 0.29 0.48 0.62 0.65 0.61 0.56 0.47 0.34 0.22
0.0169 0.0106 0.0029 −0.0020 −0.0055 −0.0062 −0.0050 −0.0045 −0.0012 0.0083 0.0064 0.0020 −0.0026 −0.0044 −0.0039 −0.0037 −0.0031 −0.0008
0.29 0.55 0.70 0.68 0.64 0.57 0.45 0.39 0.10 0.27 0.46 0.60 0.64 0.61 0.57 0.48 0.35 0.23
0.0138 0.0069 −0.0001 −0.0038 −0.0056 −0.0052 −0.0024 −0.0015 0.0013 0.0086 0.0065 0.0017 −0.0031 −0.0049 −0.0043 −0.0040 −0.0032 −0.0007
100.0
The standard uncertainties u are u(T) = 0.01 K, ur(P) = 0.01, and u(x1) = u(y1) = 0.002. bΔT = Texpt − Tcalc and Δy1 = yexpt − ycalc 1 1 were calculated using the Wilson model. cΔT and Δy1 were calculated using the NRTL model.
a
Table 5. Results of Consistency Tests for the Binary System ZE-2-Methyl-2-butenenitrile (1) + 2-Methyl-3-butenenitrile (2) point test (criterion: Δyi < 0.01, ΔP < 1.33 kPa)
area test (criterion: D − J < 10)
direct test of Van Ness
system condition
AADy1a
AADy2a
AADPb/kPa
D−J
RMS δ ln(γ1/γ2)c
consistency index
50.0 kPa 100.0 kPa
0.0072 0.0063
0.0074 0.0065
0.30 0.41
−1.99 3.69
0.039 0.029
2 2
AADyi = average absolute deviation in the vapor-phase mole fraction yi. bAADP = average absolute deviation in the pressure. cRMS δ ln(γ1/γ2) = calc 2 1/2 for the NRTL model. (∑Nm=1{[ln(γ1/γ2)]expt m − [ln(γ1/γ2)]m } /N) a
data were 1.964% and 0.907% for ZE-2-methyl-2-butenenitrile and 2-methyl-3-butenenitrile, respectively. Isobaric Binary Systems. The temperatures T, liquidphase mole fractions x1, and vapor-phase mole fractions y1 for ZE-2-methyl-2-butenenitrile (1) + 2-methyl-3-butenenitrile (2) mixtures at 100.0 and 50.0 kPa are reported in Table 4. The activity coefficients of pure liquid i (γi) were calculated from the equality of the component fugacities in the liquid and vapor phases under the assumptions of an ideal vapor phase and a Poynting factor of unity, i.e.,
γi =
methyl-3-butenenitrile (2) system are shown in Table 5. The results from point and area consistency tests indicated that the VLE data for this system are thermodynamically consistent. Moreover, the “direct test of consistency” discussed by Van Ness10 was also used to verify the quality of the binary VLE experimental data. In the direct test, a consistency index associated with the test characterizes the degree of departure of a data set from consistency. The proposed consistency index starts at 1 for highly consistent data and goes to 10 for data of very poor quality in accordance with an appropriate measure in the root-mean-square (RMS) value of δ ln(γ1/γ2). The residual in the logarithm of the activity coefficient ratio, δ ln(γ1/γ2), between the set of activity coefficients obtained from the experimental data and the set obtained from the correlation using the nonrandom two-liquid (NRTL) equation with two temperature dependence parameters was calculated. The δ ln(γ1/γ2) values for the binary system ZE-2-methyl-2butenenitrile (1) + 2-methyl-3-butenenitrile (2) at 50.0 and 100.0 kPa were both found to be 2. The results of the direct test suggested that all of the binary VLE data are acceptable. Correlation. The activity coefficients were correlated with the Wilson model,11 given by eq 3,
yi (P /kPa) xi(Pi°/kPa)
(2)
where xi and yi are the liquid- and vapor-phase mole fractions, respectively, at equilibrium for pure component i, P is the total pressure of the binary system, and Pi° is the vapor pressure of pure component i calculated using the Antoine equation. For the binary system ZE-2-methyl-2-butenenitrile (1) + 2-methyl3-butenenitrile (2), the equilibrium temperature decreased with increasing ZE-2-methyl-2-butenenitrile mole fraction. This can be explained by the fact that ZE-2-methyl-2-butenenitrile has a higher vapor pressure than 2-methyl-3-butenenitrile at the same temperature, and therefore, the boiling point decreases automatically if the mole fraction of ZE-2-methyl-2-butenenitrile increases. The experimental data were tested for thermodynamic consistency using the point test of Fredenslund et al.8 and the area test of Herington.9 The results of the consistency tests on the VLE data for the ZE-2-methyl-2-butenenitrile (1) + 2-
⎛ Λij Λji ⎞ ⎟ − ln γi = −ln(xi + Λijxj) + xj⎜⎜ xj + Λjixi ⎟⎠ ⎝ xi + Λijxj (3)
and the NRTL model, C
12
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Table 6. Values of the Correlation Parameters for the Activity Coefficients and Deviations for the Studied Binary System ZE-2Methyl-2-butenenitrile (1) + 2-Methyl-3-butenenitrile (2) equation parameters Wilson
deviations NRTL
RMST/K
RMSy1
system condition
Λ12
Λ21
(g12 − g11)/(J·mol−1)
(g21 − g22)/(J·mol−1)
Wilson
NRTL
Wilson
NRTL
50.0 kPa 100.0 kPa
0.8131 0.8435
1.0754 1.0768
−64.5535 48.8697
448.1094 237.9979
0.30 0.49
0.52 0.49
0.0076 0.0045
0.0060 0.0047
ln γi =
∑j xjτjiGji ∑k xkGki
+
∑ j
⎛ ∑ xτ G ⎞ ⎜⎜τij − k k kj kj ⎟⎟ ∑k xkGkj ⎠ ∑k xkGkj ⎝
ZE-2-methyl-2-butenenitrile and 2-methyl-3-butenenitrile were all close to 1, suggesting that the solutions showed ideal behavior.
xjGij
(4)
in which τij = (gij − gii)/RT
and
Gij = exp( −αijτij)
where R is the gas constant and αij = 0.3 in this study. The values of the parameters for both of the equations studied were obtained by the Marquardt method. The sum of the squares of the relative deviations in vapor-phase mole fraction was minimized during optimization of the parameters. The objective function (OF) used was the following: ⎛ y calc − y expt ⎞2 OF = ∑ ⎜⎜ i expt i ⎟⎟ yi ⎠ i=1 ⎝ n
(5)
ycalc i
where n is the number of components, is the vapor-phase mole fraction of component i calculated by the model, and yexpt i is the experimental vapor-phase mole fraction of component i. The correlation results were evaluated using the quantities RMST and RMSy1 defined as follows: ⎡ N (T calc − T expt)2 ⎤ m ⎥ RMST = ⎢ ∑ m ⎢⎣ m = 1 ⎥⎦ N
Figure 1. Plots of the experimental values of the activity coefficients, γ, against liquid-phase mole fraction, x1, at 50 kPa for the binary mixture ZE-2-methyl-2-butenenitrile (1) + 2-methyl-3-butenenitrile (2): ●, γ1; ■, γ2.
1/2
⎡ N RMSy1 = ⎢ ∑ ⎢⎣ m = 1
(y1calc m
− N
(6)
The reduced excess molar Gibbs free energy (GE/RT) was calculated from the equation
1/2 )2 ⎤ y1expt m ⎥
⎥⎦
n
GE /RT =
(7)
∑ xi ln γi i=1
where N is the number of data points, the Tcalc are the m temperatures calculated using the model for the isobaric binary calc systems, the Texpt m are the experimental temperatures, the y1m are the vapor-phase compositions calculated by the model for the isobaric binary systems, and the yexpt 1m are the experimental vapor-phase compositions. The values of the correlation parameters and the deviations between the experimental and calculated data are shown in Table 6. For the experimental binary system ZE-2-methyl-2-butenenitrile (1) + 2-methyl-3-butenenitrile (2), the RMS deviations in mole fraction were 0.0076 and 0.0045 at P = 50.0 kPa and P = 100.0 kPa, respectively, and the RMS deviations in temperature were 0.30 K and 0.49 K at P = 50.0 kPa and P = 100.0 kPa, respectively, for the Wilson model. For the NRTL model, the RMS deviations in mole fraction were 0.0060 and 0.0047 at P = 50.0 kPa and P = 100.0 kPa, respectively, and the RMS deviations in temperature were 0.52 K and 0.49 K at P = 50.0 kPa and P = 100.0 kPa, respectively. The temperature and mole fraction deviations of the two models for every experimental point are shown in Table 4. The experimental activity coefficients for these binary systems are plotted as functions of the liquid-phase mole fraction in Figures 1 and 2. The activity coefficient values for
(8)
Figure 2. Plots of experimental values of activity coefficients, γ, against liquid-phase mole fraction, x1, at 100 kPa for the binary mixture ZE-2methyl-2-butenenitrile (1) + 2-methyl-3-butenenitrile (2): ●, γ1; ■, γ2. D
DOI: 10.1021/acs.jced.5b00943 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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where n is the number of components. The variation of GE/RT with liquid-phase composition for the binary system is presented in Figure 3. The GE/RT values for the ZE-2-
Article
LIST OF SYMBOLS
Variables
P A, B, C P° T x y g OF n RMST RMSy N
pressure Antoine coefficients (eq 1) pure-component vapor pressure temperature mole fraction in the liquid phase mole fraction in the vapor phase NRTL binary interaction parameter objective function number of components root-mean-square deviation of the temperature root-mean-square deviation of the vapor-phase mole fraction number of data points
Greek Letters
γ activity coefficient α NRTL nonrandomness parameter Λ Wilson binary interaction parameter Subscripts/Superscripts
i j k m expt calc
Figure 3. Plots of reduced excess molar Gibbs free energy, GE/RT, against liquid-phase mole fraction, x1, for the binary mixture ZE-2methyl-2-butenenitrile (1) + 2-methyl-3-butenenitrile (2): ●, 50 kPa; ■, 100 kPa.
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methyl-2-butenenitrile +2-methyl-3-butenenitrile system are close to zero, indicating that ideal behavior is essentially exhibited by the system. All of the excess Gibbs free energies were positive deviations from ideal behavior.
REFERENCES
(1) Acosta-Ramírez, A.; Flores-Gaspar, A.; Muñoz-Hernández, M.; Arevalo, A.; Jones, W. D.; García, J. J. Nickel Complexes Involved in the Isomerization of 2-Methyl-3-butenenitrile. Organometallics 2007, 26, 1712−1720. (2) Acosta-Ramírez, A.; Flores-Gaspar, A.; Muñoz-Hernández, M.; Arévalo, A.; Jones, W. D.; García, J. J. Nickel Complexes Involved in the Isomerization of 2-Methyl-3-butenenitrile. Organometallics 2007, 26, 1712−1720. (3) Saito, S.; Motawia, M. S.; Olsen, C. E.; Møller, B. L.; Bak, S. Biosynthesis of rhodiocyanosides in Lotus japonicus: Rhodiocyanoside A is synthesized from (Z)-2-methylbutanaloxime via 2-methyl-2butenenitrile. Phytochemistry 2012, 77, 260−267. (4) Bennett, R. N.; Deans, A. A.; Harris, J. G. H.; Ritchie, P. D.; Shim, J. S. Studies in pyrolysis. Part XIII. Competitive alkyl−oxygen and acyl−oxygen scission in the pyrolysis of esters; αα-disubstituted cyanomethyl carboxylates. J. Chem. Soc. 1958, 0, 4508−4515. (5) Karl, M. DE 1253704, 1967. (6) Arthur, P., Jr.; Pratt, B. C. U.S. Patent 2,666,748, 1954. (7) Wang, D. C.; Yao, S.; Cao, Y.; Yao, T.; Song, H. Vapor pressures and isobaric (vapor + liquid) equilibrium data for the binary system of (RS-4-vinyl-1-cyclohexene + ZE-3-pentenenitrile) at (50.0 and 100.0) kPa. J. Chem. Thermodyn. 2016, 92, 55−59. (8) Fredenslund, A.; Gmehling, J.; Rasmussen, P. Vapor−Liquid Equilibria Using UNIFAC; Elsevier: Amsterdam, 1977. (9) Herington, E. F. G. Tests for consistency of experimental isobaric vapor liquid equilibrium data. J. Inst. Pet. 1951, 37, 457−470. (10) Van Ness, H. C. Thermodynamics in the treatment of vapor/ liquid equilibrium (VLE) data. Pure Appl. Chem. 1995, 67, 859−872. (11) Wilson, G. M. Vapor-liquid equilibria XI. A new expression for the excess free energy of mixing. J. Am. Chem. Soc. 1964, 86, 127−130. (12) Renon, H.; Prausnitz, J. M. Local compositions in thermodynamics for liquid mixtures. AIChE J. 1968, 14, 135−144.
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CONCLUSION In this work, the vapor pressures of ZE-2-methyl-2-butenenitrile and 2-methyl-3-butenenitrile as functions of temperature were measured and correlated with the Antoine equation. Isobaric binary VLE data at pressures of 50.0 and 100.0 kPa for the binary system ZE-2-methyl-2-butenenitrile (1) + 2-methyl3-butenenitrile (2) were determined and verified for thermodynamic consistency. The experimental VLE data can be correlated satisfactorily using the Wilson and NRTL models. The correlation results for Wilson and NRTL models for this binary system were both acceptable. The separation of ZE-2methyl-2-butenenitrile and 2-methyl-3-butenenitrile by normal rectification could be difficult because of the close VLE behaviors of these two compounds. Further VLE studies of related compounds seem to be needed to better explore the separation process.
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ith component jth component kth component index of experimental data points experimental calculated
AUTHOR INFORMATION
Corresponding Author
*Tel: +86-28-8540-5221. Fax: +86-28-8540-5221. E-mail:
[email protected]. Funding
This work was supported by the Scientific Research Foundation of Mianyang Normal University (QD2014A008) and the Educational Commission of Sichuan Province, China (16ZB0319). Notes
The authors declare no competing financial interest. E
DOI: 10.1021/acs.jced.5b00943 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
