Article

pubs.acs.org/jced

Measurements of Liquid−Liquid Equilibria for the Quaternary

System 2‑Methoxy-2-methylpropane + Phenol + Hydroquinone +
Water at 313.15 K
Yun Chen,* Yong Lei, Xiuxi Li, and Yu Qian
Department of Chemistry and Chemical Engineering, South China University of Technology, 381 Wushan Road, Guangzhou,
510640, P. R. China

ABSTRACT: Liquid−liquid equilibria (LLE) data for the

quaternary system 2-methoxy-2-methylpropane (MTBE) +
phenol + hydroquinone + water and its one ternary subsystem
MTBE + hydroquinone + water were measured at 313.15 K
and atmospheric pressure. The distribution of phenol and
hydroquinone between the organic phase and the aqueous
phase was investigated. The reliability of the experimental tie-
line data of the quaternary system was verified by the Hand
and Bachman correlations. The experimental data were
correlated with the nonrandom two-liquid (NRTL) and
universal quasichemical activity coefficient (UNIQUAC)
models. The binary interaction parameters of these two
models were reported. Both models correlated the exper-
imental data successfully. Experimental LLE data were compared with the values calculated by these two models, and good
agreement was obtained for the ternary and quaternary systems.

■ INTRODUCTION
A large amount of wastewater was produced by cooling and
washing the crude gas in coal-pressurized gasification. It usually
contains phenolic compounds, ammonia, carbon dioxide,
hydrogen sulfide, fatty acid, tar, and so forth; these wastewaters
are often characterized by a deep red color, foul odor, and pH
8−10.1,2 The concentration of phenol in the wastewater could
reach 10 000 mg·L−1, which makes biological treatment more
difficult. Moreover, the polyhydric phenols, such as dihydric
phenols and trihydric phenols, appear in concentrations of
The aim of this work is to determine the liquid−liquid data
for the design and simulation of removing phenols from coal-
gasification wastewater using MTBE. In this paper, LLE
measurements for the quaternary system MTBE + phenol +
hydroquinone + water and its one ternary subsystem MTBE +
hydroquinone + water were performed at T = 313.15 K and
atmospheric pressure. The LLE data were correlated by two
activity coefficient models: the nonrandom two-liquid
(NRTL)7 and universal quasichemical activity coefficient
(UNIQUAC)8 models, and the binary interaction parameters
of these two models were determined by using Aspen Plus.

thousands of parts per million. These polyhydric phenols are
extremely resistant to biological oxidation.3 Phenols are very
harmful to the environment because they are toxic even at low
concentrations. Therefore, it is crucial to remove these
substances before the wastewater is discharged. The treatment
of phenols in coal-gasification wastewater usually consists of
two steps including the solvent extraction process and the
biological treatment.4
Reliable phase equilibrium data are essential for the design of
industrial units for the phenol extraction process. In previous
work, liquid−liquid equilibria (LLE) data for a partially miscible
ternary system (2-methoxy-2-methylpropane (MTBE) +
phenol + water) at different temperatures were reported by
Lei et al.5 MTBE, a fuel additive, probably due to its high
polarity and the possibility of establishing H-bonds with
phenol, was found to be largely superior to hydrocarbons as an
extracting agent.6 The LLE data also indicate that it is feasible
to remove phenol by extraction with MTBE from wastewater.
■
EXPERIMENTAL SECTION
Chemicals. MTBE was obtained from Sinpharm Chemical
Reagent Co., Ltd. Phenol was obtained from GuangZhou
Chemical Reagent Factory. Hydroquinone and 1-octanol were
obtained from TianJin Kemiou Chemical Reagent Co., Ltd.
Methanol was obtained from ShangHai LingFeng Chemical
Reagent Co., Ltd. The content of water in the chemicals was
measured using a Karl Fischer titrator (HB43, Mettler Toledo),
and the amount was less than 5·10−5 g·g−1. The density was
obtained with DH-120T density meter supplied by HongTuo
instruments (Dong Guan) Co., Ltd. with an accuracy of 0.0001
g·cm−3. The refractive index was measured by an Abbe
refractometer (WYA-2S) with an uncertainty of ± 0.0002.
Received: May 21, 2013
Accepted: September 4, 2013
Published: September 16, 2013

© 2013 American Chemical Society 2793 dx.doi.org/10.1021/je400488x | J. Chem. Eng. Data 2013, 58, 2793−2798
Journal of Chemical & Engineering Data
Table 1. Purity, Density, and Refractive Index of Chemicals at 293.15 K and Atmospheric Pressure
density (g·cm−3)
component purity (mass fraction) exp.
MTBE 0.99 0.7398
methanol 0.999 0.7921
1-octanol 0.995 0.8229
phenol 0.995 1.0581b
hydroquinone 0.99 1.328
a
From ref 9. bAt 314.45 K. cFrom ref 10.
The purity of the materials was checked by gas chromatog-
raphy. All of the chemicals in the study were used without
further purification. Deionized and distilled water was used in
all experiments. The purity, density, and refractive index of the
chemicals are listed in Table 1 along with the literature values.
Procedure. The LLE measurement was carried out by using
a 100 mL glass equilibrium cell equipped with a heating jacket
to keep the temperature constant. The cell temperature was
controlled by a thermostatic bath with an uncertainty of ± 0.1
K. The weights of the components were measured by an
electronic balance (Mettler Toledo) with an accuracy of ± 0.1
mg. About 80 mL of the quaternary mixture was added into the
glass cell, vigorously agitated by a magnetic stirrer for at least 2
h, and then left to settle for at least 10 h to reach phase
equilibrium. After the mixture was split into two liquid phases,
the samples of both phases were withdrawn by a syringe.
The analysis was performed by using a gas chromatograph
(GC6820, Agilent Technologies) equipped with a flame
ionization detector (FID) and a DB-5MS capillary column
(30 m × 0.32 mm × 0.25 μm). The determination of
composition is based on the internal standard. Methanol was
selected as the internal standard of MTBE and N-octanol as the
internal standard of phenol and hydroquinone. Water
concentration was obtained by mass balance. The injector
and detector temperatures were set at (533.15 and 523.15) K.
The initial temperature of oven was kept at 303.15 K for 2 min
and then increased at a rate of 30 K·min−1 to reach 453.15 K.
The carrier gas was nitrogen with a rate of 30 mL·min−1
throughout the column. Each sample was analyzed at least three
times, and the deviation obtained from the average value was
less than 2 %. To obtain the uncertainty in the equilibrium mass
fraction values, we prepared some known mixtures in the
homogeneous region close to the binodal curve by mass. These
mixtures were analyzed by the chromatograph. The mass
fraction measurement uncertainties for the four materials were:
MTBE 0.0011, phenol 0.00021, hydroquinone 0.00042, and
water 0.01.
Before the experiment, the quaternary mixtures were
prepared by mixing MTBE and aqueous solution. The aqueous
solution was prepared by adding water into the (hydroquinone
+ phenol) mixtures until the mass fraction of phenol and
hydroquinone reached 0.03. Figure 1 shows the method
schematically, where M denotes the content (mass fraction) of
hydroquinone in (hydroquinone + phenol) mixtures. The
approximate values of M1, M2, and M3 are 0.242, 0.495, and
0.748, respectively.
■
RESULTS AND DISCUSSION
LLE Experimental Data. The LLE data of the ternary
system are listed in Table 2. The LLE data of the quaternary
system MTBE + phenol + hydroquinone + water are presented
2794
Article
refractive index
lit. exp. lit.
a
0.7407 1.3689 1.3692a
0.7913a 1.3281 1.3286a
0.8239a 1.4288 1.4292a
1.0576a,b 1.5418b 1.54178a,b
1.3320c
Figure 1. Schematic representation of MTBE + phenol + hydro-
quinone + water at 313.15 K. M1, M2, and M3 are quaternary sectional
planes.
in Table 3 and shown in Figure 2. All concentrations are
expressed in mass fraction.
Considering the extraction temperature of phenols from
coal-gasification wastewater in the industry, the LLE data were
determined at T = 313.15 K. As this study is focused on the
recovery of dilute phenol and hydroquinone in coal-gasification
wastewater, the LLE data are determined in a small range of
concentration, which can be seen from Tables 2 and 3 and
Figure 2.
To study the influence of the content of hydroquinone in
(hydroquinone + phenol) mixtures on the phase distribution of
phenol and hydroquinone, the distribution coefficient (D) and
the selectivity (S) can be calculated from Tables 2 and 3. The D
and S are defined as follows:
wiO
D=
wiW (1)
(wi /w4)O
S=
(wi /w4)W (2)
where i refers to the component phenol or hydroquinone, w is
the mass fraction, and the superscripts O and W denote the
organic phase and the aqueous phase, respectively.
The distribution curves of phenol and hydroquinone, shown
in Figures 3 and 4, consist of the experimental and calculated
mass fraction of phenol and hydroquinone for the quaternary
system. The distribution coefficient of phenol slightly decreases
when the content of hydroquinone in (hydroquinone +
phenol) mixtures increases. However, the distribution coef-
ficient of hydroquinone increases when the content of phenol
increases, and the increasing becomes more obvious when the
concentration of hydroquinone increases. These results indicate
that MTBE with highly concentrated phenol could be beneficial
for the removal of hydroquinone. This could be very significant
as the hydroquinone is very difficult to extract. As the
distribution coefficient of phenol is much greater than that of
hydroquinone, MTBE could contain a high concentration of
phenol in first stage of the counter-current extraction, which
dx.doi.org/10.1021/je400488x | J. Chem. Eng. Data 2013, 58, 2793−2798
Journal of Chemical & Engineering Data Article

Table 2. Experimental LLE Data (Mass Fraction) for the Ternary System MTBE (1) + Hydroquinone (2) + Water (3) at 313.15
K at 0.1 MPaa
organic phase aqueous phase
w1 w2 w3 w1 w2 w3
0.973476 0.007026 0.019498 0.020028 0.002417 0.977555
0.975492 0.005971 0.018537 0.021448 0.001483 0.977069
0.978032 0.004007 0.017961 0.022305 0.000705 0.976990
0.979933 0.003220 0.016847 0.022770 0.000561 0.976669
0.981121 0.002691 0.016188 0.023573 0.000402 0.976025
0.981974 0.002281 0.015745 0.023774 0.000369 0.975857
0.982062 0.002205 0.015733 0.024067 0.000356 0.975577
0.983464 0.001547 0.014989 0.024456 0.000252 0.975292
0.9853 0 0.0147 0.025 0 0.975
a
Standard uncertainties u are u(T) = 0.1 K, u(w1) = 0.0011, u(w2) = 0.00042, and u(w3) = 0.01.

Table 3. Experimental LLE Data (Mass Fraction) for the Quaternary System MTBE (1) + Phenol (2) + Hydroquinone (3) +
Water (4) at 313.15 K at 0.1 MPaa
organic phase aqueous phase
w1 w2 w3 w4 w1 w2 w3 w4
M1 = 0.242
0.896335 0.066504 0.008936 0.028225 0.016447 0.001196 0.001554 0.980803
0.930670 0.036650 0.005857 0.026823 0.017502 0.000665 0.001154 0.980679
0.942965 0.028057 0.004436 0.024542 0.018101 0.000517 0.000949 0.980433
0.949529 0.022904 0.003765 0.023802 0.018365 0.000472 0.000761 0.980402
0.961430 0.016237 0.002527 0.019806 0.019389 0.000316 0.000597 0.979698
0.963090 0.016036 0.002279 0.018595 0.020318 0.000275 0.000433 0.978974
0.972862 0.009473 0.001489 0.016176 0.022066 0.000182 0.000304 0.977448
0.979512 0.004577 0.000724 0.015187 0.024031 0.000097 0.000139 0.975733
M2 = 0.495
0.919596 0.034510 0.016678 0.029216 0.017002 0.000653 0.003908 0.978437
0.952676 0.014731 0.007312 0.025280 0.019826 0.000260 0.001742 0.978172
0.960384 0.011900 0.005946 0.021770 0.021955 0.000206 0.001330 0.976509
0.966989 0.008178 0.004635 0.020198 0.022895 0.000168 0.001041 0.975896
0.974180 0.005757 0.002716 0.017348 0.023552 0.000103 0.000569 0.975776
0.977744 0.004501 0.001166 0.016589 0.025289 0.000073 0.000246 0.974393
M3 = 0.748
0.935374 0.014510 0.023207 0.026909 0.016111 0.000292 0.005776 0.977821
0.953069 0.009445 0.016327 0.021159 0.017799 0.000196 0.004202 0.977803
0.964609 0.005508 0.009055 0.020828 0.019911 0.000117 0.002372 0.977601
0.969247 0.004062 0.007183 0.019509 0.020992 0.000092 0.001915 0.977002
0.973896 0.002899 0.005989 0.017216 0.021673 0.000065 0.001369 0.976892
0.978482 0.001915 0.003622 0.015981 0.023108 0.000050 0.001040 0.975802
0.980452 0.001475 0.003011 0.015062 0.023960 0.000045 0.000651 0.975344
0.982602 0.000830 0.001772 0.014796 0.024388 0.000034 0.000345 0.975233
a
Standard uncertainties u are u(T) = 0.1 K, u(w1) = 0.0011, u(w2) = 0.00021, u(w3) = 0.00042, and u(w4) = 0.01.

would contribute to the removal of hydroquinone in the latter where a1, b1 and a2, b2 are the parameters of the Hand and
extraction. This phenomenon is similar to liquid−liquid Bachman correlations. The parameters together with the
equilibrium for the quaternary system of water−isopropyl regression coefficients (R2) are given in Table 4. All of the
ether−phenol−hydroquinone.11 values of R2 are greater than 0.97. These results indicate a good
Hand12 and Bachman13 correlations were applied to assess consistency and a high reliability of the experimental data.
the reliability of the experimental tie-line data of the quaternary Data Correlation. The experimental LLE data were
system. The correlations are given by eqs 2 and 3, respectively.
correlated by using the NRTL and UNIQUAC correlations.
⎛ w ⎞O ⎛ w ⎞W The nonrandomness parameter (αij) for the NRTL correlation
ln⎜ 2 + 3 ⎟ = a1 + b1 ln⎜ 2 + 3 ⎟ was fixed at 0.2 or 0.3. For the UNIQUAC correlation, the
⎝ w1 ⎠ ⎝ w4 ⎠ (3) structural parameters (r and q) referred to the literature,14−16
and the values are shown in Table 5. The binary interaction
⎛ wO ⎞ parameters (Aij and Aji) were obtained from Aspen Plus by
w1O = a 2 + b2⎜ 1W ⎟ minimizing the objective function (OF) given in the following
⎝ w4 ⎠ (4) equation:
2795 dx.doi.org/10.1021/je400488x | J. Chem. Eng. Data 2013, 58, 2793−2798
Journal of Chemical & Engineering Data Article

Figure 4. Distribution curve: the mass fraction of hydroquinone in the

aqueous phase (wW 3 ) against the mass fraction of hydroquinone in the
organic phase (wO3 ) at 313.15 K.

Table 4. Hand and Bachman Correlation Parameters for the

System MTBE + Phenol + Hydroquinone + Water
Hand Bachman
M a1 b1 R2 a2 b2 R2
0.242 1.0779 3.7140 0.9867 0.9302 0.0476 0.9983
0.495 0.8579 1.5777 0.9757 0.9190 0.0565 0.9989
0.748 0.9849 1.7037 0.9899 0.9241 0.0521 0.9988

Table 5. UNIQUAC Structural (Area and Volume)

Parameters
component r q
MTBE 4.0678 3.6320
phenol 3.5517 2.6800
hydroquinone 3.91562 3.0080
water 0.9200 1.4000

m 2 n ⎡ exp cal 2 ⎤
(Tkexp − Tkcal)2 (wijk − wijk )
OF = ∑ ∑ ∑ ⎢⎢ + ⎥
⎥⎦
i=1 j=1 k=1 ⎣ σT2 2
σw
(5)
where m and n are the number of components and the number
Figure 2. LLE phase diagrams for the system MTBE + phenol + of the tie-lines, wexp and Texp are the experimental mass fraction
hydroquinone + water at 313.15 K: (a) M1 = 0.242, (b) M2 = 0.495, and temperature, and wcal and Tcal are the calculated mass
(c) M3 = 0.748; ■, experimental data. fraction and temperature, respectively. The subscripts i, j, and k
refer to the component, the phase, and the tie-line, respectively.
σT and σw denote the standard deviation of the temperature and
the mass fraction.
The root-mean-square-deviation (RMSD) was used to
ascertain the agreement between the experimental data and
the calculated data. The RMSD value is defined as

⎡ ∑m ∑2 ∑n (w exp − w cal)2 ⎤1/2

RMSD = 100⎢ ⎥
i=1 j=1 k=1 ijk ijk
⎢ 2mn ⎥
⎣ ⎦ (6)

The binary interaction parameters of the NRTL and

Figure 3. Distribution curve: the mass fraction of phenol in the
aqueous phase (wW 2 ) against the mass fraction of phenol in the organic
phase (wO2 ) at 313.15 K.
2796
UNIQUAC models for the ternary systems are listed in
Table 6, along with the RMSDs between the experimental and
the calculated values. The agreement between the calculated
and the experimental LLE data is good.
To represent the quaternary system from information of
ternary systems, two binary interaction parameters for the
(phenol + hydroquinone) pairs were fitting from the
dx.doi.org/10.1021/je400488x | J. Chem. Eng. Data 2013, 58, 2793−2798
Journal of Chemical & Engineering Data Article

Table 6. Binary Interaction Parameters of the NRTL and UNIQUAC Models for the Ternary System at T = 313.15 K
component NRTL UNIQUAC
i−j Aij/K Aji/K αij RMSD Aij/K Aji/K RMSD
MTBE (1) + Hydroquinone (2) + Water (3)
1−2 −1495.6015 −900.40807 0.3 0.107 550.379533 719.331901 0.104
1−3 331.225417 1415.94862 0.2 −571.16528 −104.18182
2−3 351.043104 −3054.177 0.2 704.604847 898.856816

Table 7. Binary Interaction Parameters of NRTL and UNIQUAC Models for the Quaternary System at T = 313.15 Ka
component NRTL UNIQUAC
i−j Aij/K Aji/K αij RMSD Aij/K Aji/K RMSD
MTBE (1) + Phenol (2) + Hydroquinone (3) + Water (4)
1−2 −308.915085 −406.354464 0.3 0.221 −685.464555 411.080058 0.258
1−3 −1495.6015 −900.40807 0.3 550.379533 719.331901
1−4 341.460154 1411.192685 0.2 −572.70049 −103.19794
2−3 10000 −1299.4945 0.2 1472.99942 304.218043
2−4 −932.724732 2386.53906 0.2 1431.69887 −1018.06426
3−4 351.043104 −3054.177 0.2 704.604847 898.856816
a
Two binary interaction parameters fitted from the LLE data.

Table 8. Binary Interaction Parameters of NRTL and UNIQUAC Models for the Quaternary System at T = 313.15 Ka
component NRTL UNIQUAC
i−j Aij/K Aji/K αij RMSD Aij/K Aji/K RMSD
MTBE (1) + Phenol (2) + Hydroquinone (3) + Water (4)
1−2 2136.77778 −1099.4516 0.3 0.162 −862.077554 432.361923 0.164
1−3 −1379.4985 −983.5252 0.3 646.562235 361.819518
1−4 351.009775 1441.20259 0.2 −550.420207 −115.334846
2−3 −4278.2406 5699.63745 0.2 1218.64656 −2020.97188
2−4 −484.24873 929.677439 0.2 −1107.48837 −111.47125
3−4 −1327.4146 −101.4147 0.2 398.585243 579.482463
a
Twelve binary interaction parameters fitted from the LLE data.

quaternary (liquid−liquid) data by fixing the remaining 10
binary interaction parameters at the values or mean values
obtained from ternary subsystems. The parameters and the
RMSDs are given in Table 7.
When 12 binary interaction parameters characterizing the
quaternary system are fitted from the LLE data, the RMSD
decreases for both NRTL and UNIQUAC models, giving a
better presentation of the quaternary system. Table 8 shows the
binary interaction parameters for the quaternary system. It can
be seen that both models give a good representation of the tie-
line data for the quaternary system.
the 10 binary interaction parameters at the values or mean
values obtained from ternary subsystems and then optimizing
the remaining two parameters for the (phenol + hydroquinone)
pairs. However, when 12 binary interaction parameters
characterizing the quaternary system were fitted from the
LLE data with two models, the agreement between the
experimental data and the calculated data can be improved.
The research is helpful for the design and simulation of the
extraction process and the recovery of phenols from the coal-
gasification wastewater.

■ CONCLUSIONS
LLE data for the ternary system (MTBE + hydroquinone +
water) and the quaternary system (MTBE + phenol +
hydroquinone + water) were investigated at 313.15 K and
atmosphere pressure. For the quaternary system, the
distribution curves of phenol and hydroquinone are shown in
Figure 3 and 4, and it can be observed that the changes of
hydroquinone content could affect the distribution coefficient
of phenol and hydroquinone. The reliability of the LLE data of
the quaternary system was evaluated by the Hand and Bachman
correlations, and a good consistency was obtained.
The experimental ternary and quaternary data were
accurately correlated with the NRTL and UNIQUAC models.
Both models give a good presentation of the systems. The
quaternary LLE data can be satisfactorily correlated by fixing
■ AUTHOR INFORMATION
Corresponding Author
*Tel.: 86-20-87112046. Fax: 86-20-87112046. E-mail:
yunchen@scut.edu.cn.
Funding
Financial support from Project of the Science and Technology
New Star of Pearl River in Guangzhou (2011J2200056) and
National Science Foundation of China (nos. 20906028,
21136003, and 21176089) are gratefully appreciated.
Notes
The authors declare no competing financial interest.
■ REFERENCES
(1) Shi, Y.; Fu, Z. Coal pressurized gasification wastewater treatment;
Chemical Industry Press: Beijing, 2001.

2797 dx.doi.org/10.1021/je400488x | J. Chem. Eng. Data 2013, 58, 2793−2798

Journal of Chemical & Engineering Data Article

(2) Gai, H.; Jiang, Y.; Qian, Y.; Zhuo, L.; Zhang, L. Chem. Eng.
(China) 2007, 35, 49−52.
(3) Greminger, D. C.; Burns, G. P.; Lynn, S.; Hanson, D. N.; King, C.
J. Solvent extraction of phenols from water. Ind. Eng. Chem. Process
Des. Dev. 1982, 21, 51−54.
(4) Yu, Z.; Chen, Y.; Feng, D.; Qian, Y. Process Development,
Simulation, and Industrial Implementation of a New Coal-Gasification
Wastewater Treatment Installation for Phenol and Ammonia Removal.
Ind. Eng. Chem. Res. 2010, 49, 2874−2881.
(5) Lei, Y.; Chen, Y.; Li, X.; Qian, Y.; Yang, S.; Yang, C. Liquid−
liquid Equilibria for the Ternary System 2-Methoxy-2-methylpropane
+ Phenol + Water. J. Chem. Eng. Data 2013, 58, 1874−1878.
(6) Busca, G.; Berardinelli, S.; Resini, C.; Arrighi, L. Technologies for
the removal of phenol from fluid streams: A short review of recent
developments. J. Hazard. Mater. 2008, 160, 265−288.
(7) Renon, H.; Prausnitz, J. M. Local compositions in thermody-
namic excess functions for liquid mixtures. AIChE J. 1968, 14, 135−
144.
(8) Abrams, D. S.; Prausnitz, J. M. Statistical thermodynamics of
liquid mixtures: A new expression for the excess Gibbs energy of partly
or completely miscible systems. AIChE J. 1975, 21, 116−128.
(9) Cheng, N. Solvents Handbooks, 4th ed.; Chemical Industry Press:
Beijing, 2007.
(10) Liu, G.; Ma, L.; Liu, J. Physical Properties Handbook of Chemicals;
Chemical Industry Press: Beijing, 2013.
(11) Xu, X.; Luo, G.; Yang, C.; Zhang, G. Determination and
Correlation of Liquid−Liquid Equilibrium Data for the Quaternary
system of Water-Isopropyl Ether-Phenol-Hydroquinone. Petrochem.
Technol. (China) 2001, 30, 538−540.
(12) Hand, D. Dineric Distribution. J. Phys. Chem. 1929, 34, 1961−
2000.
(13) Bachman, I. Tie Lines in Ternary Liquid Systems. Ind. Eng.
Chem., Anal Ed. 1940, 12, 38−39.
(14) Alkandary, J. A.; Aljimaz, A. S.; Fandary, M. S.; Fahim, M. A.
Liquid−liquid equilibria of water + MTBE + reformate. Fluid Phase
Equilib. 2001, 187−188, 131−138.
(15) Mafra, M. R.; Krähenbühl, M. A. Liquid−Liquid Equilibrium of
(Water + Acetone) with Cumene or α-Methylstyrene or Phenol at
Temperatures of (323.15 and 333.15) K. J. Chem. Eng. Data 2006, 51,
753−756.
(16) Yang, C.; Qian, Y.; Jiang, Y.; Zhang, L. Liquid−liquid equilibria
for the quaternary system methyl isobutyl ketone−water−phenol−
hydroquinone. Fluid Phase Equilib. 2007, 258, 73−77.

2798 dx.doi.org/10.1021/je400488x | J. Chem. Eng. Data 2013, 58, 2793−2798