Article

Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX pubs.acs.org/jced

Liquid−Liquid Equilibrium for Ternary System n‑Butanol + n‑Hexane

+ Ethylene Glycol at 298.15−323.15 K
Qingsong Li,* Midong Shi, Liping Wang, Gaoyin He, and Fan Gan
The State Key Lab of Heavy Oil Processing, College of Chemical Engineering, China University of PetroleumEast China, Qingdao,
Shandong 266580, China

ABSTRACT: The liquid−liquid equilibrium (LLE) experiments for n-butanol + n-

hexane + ethylene glycol were carried out and LLE data were measured at 298.15,
303.15, 308.15, 313.15, and 323.15 K under atmospheric pressure. The analysis results
of the effects of n-butanol content and temperature on extraction showed that high n-
butanol content was not favorable for extraction, and temperature had little effect on
extraction. Moreover, the NRTL and UNIQUAC models were applied to correlate the
LLE data, and the correlated data indicated that the UNIQUAC model showed a better
correlation performance.

■ INTRODUCTION
Fischer−Tropsch (FT) synthesis is a kind of indirect coal
liquefaction technology, which uses the synthetic gas as raw
material. Paraffin hydrocarbons, olefins, and oxygenated
compounds are the main products.1 High temperature
Fischer−Tropsch (HTFT) synthesis is the key technology of
Fischer−Tropsch synthesis. The content of olefins in HTFT
synthetic oils is about 25%,2 and the linear α-olefins in olefins
are extremely precious chemical raw materials and have high
economic value.3−6 Therefore, separation and purification of
linear α-olefins from high temperature FT synthetic oil are of
great significance.
n-Hexene is an important linear α-olefin, which can be used
as chemical raw materials of plasticizers, synthetic lubricants,
and fatty acids,7−10 and the content of n-hexene in the C6
fraction of HTFT synthetic oils is about 45%.11 Thus, n-hexene
is an ideal composition obtained from the high temperature FT
synthetic oil. n-Hexene can be separated from the C6 fraction
liquid−liquid equilibrium of n-butanol + n-butyl acetate +1-
octyl-3-methylimidazolium hexafluorophosphate. Nagata17 re-
ported the liquid−liquid equilibria of acetonitrile + n-butanol +
cyclohexane or n-heptane or n-octane at 298.15 K. However, no
more data were reported.
In C6 fraction of high temperature FT synthetic oils, n-
hexane is one of the most important substances, which has a
relatively high boiling point. Thus, n-hexane was used as a
model compound in the present work, and ethylene glycol was
selected as an extractant. The liquid−liquid equilibrium data for
n-butanol + n-hexane + ethylene glycol were measured at
298.15, 303.15, 308.15, 313.15, and 323.15 K under
atmospheric pressure. The extraction performance of ethylene
glycol was evaluated by a distribution coefficient and separation
factor. Also, the effects of temperature and n-butanol content
on the LLE data were analyzed. Moreover, NRTL and
UNIQUAC models were applied to correlate the LLE data of
this system.

with distillation technology; however, oxygen-containing
compounds in the C6 fraction can form an azeotrope with n-
hexene and other C6 hydrocarbon components.11 Therefore,
oxygen-containing compounds should be first removed before
separating n-hexene from the C6 fraction.
Solvent extraction has good application in the separation of
mixtures, such as azeotrope and high boiling components,
therefore this method was selected to separate oxygen-
containing compounds. n-Butanol is one oxygen-containing
compound in the C6 fraction.11 In the present work, it was
separated from the C6 fraction with the solvent extraction
method. At present, the liquid−liquid equilibria of n-butanol
comprise a mostly aqueous system.12−15 What is more, the
liquid−liquid phase equilibria of n-butanol in anhydrous
systems was also reported. Cai et al.16 investigated the
■
EXPERIMENTAL SECTION
Chemicals. n-Hexane was purchased from Aladdin Indus-
trial Corporation. n-Butanol and ethylene glycol were
purchased from Sinopharm Chemical Reagent. The purities
of relevant chemicals were checked with Agilent GC6820 gas
chromatograph and used without further purification. The
detailed information on all chemicals was listed in Table 1. The
mass fraction of water in n-butanol and ethylene glycol was
lower than 0.1% and 0.7%, respectively.
Received: June 23, 2017
Accepted: November 27, 2017

© XXXX American Chemical Society A DOI: 10.1021/acs.jced.7b00577

J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data Article

Table 1. Suppliers and Purity of the Chemicals The LLE data for n-butanol + n-hexane + ethylene glycol at
298.15, 303.15, 308.15, 313.15, and 323.15 K were measured in
CAS Reg. mass fraction analysis
component NO. source purity method a 50 mL liquid−liquid equilibrium kettle. The prepared mixture
n-butanol 71-36-3 Sinopharm ≥0.9950 GCa
of known mass ratio was first added into the equilibrium cell.
n-hexane 110-54-3 Aladdin ≥0.9900 GCa
Then the cell was sealed by a rubber stopper with a
ethylene 107-21-1 Sinopharm ≥0.9900 GCa thermometer with a range of 297.15−324.15 K and a standard
glycol uncertainty of 0.05 K and fixed on a magnetic stirrer. After
a
Gas chromatograph. heating the equilibrium cell to the desired temperature with an
accuracy of 0.1 K, the mixture was stirred vigorously for 3 h.
Then, the magnetic stirrer was stopped and the mixture was left
Apparatus and Procedure. The apparatus and exper- undisturbed for 12 h to reach liquid−liquid equilibrium.
imental procedure were described in detail in our previous The samples from n-hexane and ethylene glycol phases were
work.18,19 In the present work, the experiments on the taken out respectively by a microsyringe and analyzed using the
extraction of n-butanol from n-hexane with ethylene glycol as above-mentioned gas chromatograph with a thermal con-
extractant were carried out. The mass concentration range of n- ductivity detector (TCD) and Porapak N column (3 mm × 3
butanol in n-hexane−n-butanol solution was 0−45%, and based m). The injector and detector temperatures were 523 K, and
on the concentration range of n-butanol in n-hexane-n-butanol the column temperature was kept at 373 K for 1.0 min, then
solution, the composition of seven phase points was analyzed. increased to 523 K at a rate of 20 °C/min and kept for 1.5 min.
The composition of each phase was sequentially measured by To ensure the accuracy of measurement, the standard deviation
changing the mass of n-butanol. of measurement was less than 1%.

Table 2. LLE Data for n-Butanol (1) + n-Hexane (2) + Ethylene Glycol (3) at Different Temperatures 298.15−323.15 K under
100 kPa Pressurea
n-hexane phase (I) ethylene glycol phase (II)
T/K x1 x2 x3 x1 x2 x3 D S
298.15 0.0087 0.9913 <0.0001 0.0553 0.0034 0.9413 6.38 1858
0.0226 0.9773 <0.0001 0.1089 0.0067 0.8844 4.81 706
0.0411 0.9478 0.0111 0.1441 0.0102 0.8458 3.51 327
0.0647 0.9216 0.0137 0.1844 0.0168 0.7988 2.85 157
0.0969 0.8829 0.0202 0.2425 0.0314 0.7261 2.50 70
0.1393 0.8229 0.0378 0.2760 0.0442 0.6798 1.98 37
0.1860 0.7560 0.0580 0.3189 0.0765 0.6047 1.71 17
303.15 0.0092 0.9908 <0.0001 0.0577 0.0039 0.9384 6.29 1614
0.0236 0.9764 <0.0001 0.1081 0.0069 0.8850 4.58 646
0.0410 0.9550 0.0040 0.1537 0.0119 0.8344 3.75 300
0.0653 0.9257 0.0090 0.1850 0.0173 0.7977 2.83 152
0.0985 0.8850 0.0165 0.2329 0.0289 0.7382 2.36 72
0.1399 0.8286 0.0315 0.2812 0.0480 0.6708 2.01 35
0.1943 0.7521 0.0536 0.3296 0.0774 0.5931 1.70 16
308.15 0.0098 0.9902 <0.0001 0.0585 0.0042 0.9374 5.97 1418
0.0247 0.9753 <0.0001 0.0998 0.0063 0.8940 4.04 629
0.0422 0.9541 0.0036 0.1449 0.0114 0.8437 3.43 287
0.0679 0.9226 0.0095 0.1847 0.0176 0.7977 2.72 142
0.1051 0.8729 0.0219 0.2321 0.0295 0.7384 2.21 65
0.1451 0.8166 0.0383 0.2788 0.0473 0.6739 1.92 33
0.1993 0.7433 0.0574 0.3323 0.0826 0.5851 1.67 15
313.15 0.0112 0.9834 0.0054 0.0536 0.0040 0.9423 4.79 1172
0.0251 0.9708 0.0042 0.0996 0.0071 0.8934 3.97 547
0.0457 0.9466 0.0076 0.1439 0.0117 0.8445 3.14 256
0.0741 0.9131 0.0128 0.2195 0.0250 0.7555 2.96 108
0.1075 0.8723 0.0202 0.2612 0.0378 0.7010 2.43 56
0.1505 0.8107 0.0388 0.2889 0.0572 0.6539 1.92 27
0.2072 0.7283 0.0645 0.3318 0.0935 0.5747 1.60 12
323.15 0.0136 0.9853 0.0011 0.0597 0.0045 0.9358 4.39 955
0.0300 0.9680 0.0020 0.1227 0.0101 0.8671 4.09 391
0.0508 0.9439 0.0053 0.1659 0.0166 0.8175 3.26 186
0.0761 0.9148 0.0091 0.2062 0.0235 0.7703 2.71 106
0.1102 0.8690 0.0208 0.2632 0.0374 0.6994 2.39 55
0.1652 0.7947 0.0401 0.3101 0.0637 0.6262 1.88 23
0.2144 0.7343 0.0513 0.3626 0.1105 0.5269 1.69 11

a
Standard uncertainties u are u(T) = 0.1 K, u(p) = 0.5 kPa, u(x) = 0.0008.

B DOI: 10.1021/acs.jced.7b00577
J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data Article

Figure 1. Triangular phase diagrams for n-butanol + n-hexane + ethylene glycol at different temperatures (298.15−323.15 K): (□) experimental
data; (○) NRTL model; (△) UNIQUAC model.

■ RESULTS AND DISCUSSION

Experimental Data. The experimental LLE data for n-
butanol + n-hexane + ethylene glycol were measured at 298.15,
303.15, 308.15, 313.15, and 323.15 K and atmospheric pressure
by the equilibrium kettle method and presented in Table 2. The
concentrations were expressed by mole fraction. The triangular
phase diagrams of studied ternary system were shown in Figure
1. The upper right and lower left phase points were the
composition of the n-hexane phase and the ethylene glycol
phase, respectively.
C DOI: 10.1021/acs.jced.7b00577
The phase diagrams at different temperatures showed a large
two-phase region, which indicated that there was feasibility to
extract n-butanol from n-hexane−n-butanol with ethylene
glycol. The slopes of the tie-line data showed that there was
greater solubility of n-butanol in the ethylene glycol phase.
Moreover, from the LLE data in Table 2, it could be seen that
the mutual solubility between ethylene glycol and n-hexane was
small, which meant a small loss of ethylene glycol and n-hexane
in the extraction process.
Evaluation of Extraction Capacity. The extraction ability
of ethylene glycol was evaluated by distribution coefficient (D)
and separation factor (S).
J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data
x1II
D=
x1I
x 2I
S=D×
x 2II
xI1 xI2
where and were mole fraction of n-butanol and n-hexane
in n-hexane phase, respectively, and xII1 and xII2 were the mole
fraction of n-butanol and n-hexane in the ethylene glycol phase,
respectively.
The data of distribution coefficient and separation factors
were also presented in Table 2. The distribution coefficients
were greater than 1, which demonstrated that the ability of n-
butanol transferring to the ethylene glycol phase was stronger
than to the n-hexane phase, and the extraction of n-butanol was
feasible. The separation factor showed large values, which
demonstrated a high selectivity to n-butanol for ethylene glycol,
and ethylene glycol had an excellent extraction capacity.
Effect of n-Butanol Concentration. Figures 2 and 3
showed the variation of distribution coefficient and separation
Figure 2. Distribution coefficient versus mole fraction of n-butanol in
the ethylene glycol phase for n-butanol + n-hexane + ethylene glycol
system: (□) 298.15 K; (○) 303.15 K; (△) 308.15 K; (▽) 313.15 K;
(☆) 323.15 K.
factor, respectively, versus mole fraction of n-butanol in the
ethylene glycol phase according to expression style in the
literature.19 The results showed that both distribution
coefficient and separation factor decreased with increasing n-
butanol content in the ethylene glycol phase, which indicated
that the extraction capacity of ethylene glycol decreased. Also,
when the content of n-butanol in ethylene glycol phase was
lower than 0.20, the separation factor decreased rapidly;
however, the separation factor had little change at higher
content of n-butanol, which indicated that the increase in n-
butanol content in the system was very unfavorable to n-
butanol extraction.
Effect of Temperature. In this work, the effect of
temperature on LLE data and extraction capacity of ethylene
glycol were studied. From the phase diagrams of n-butanol + n-
hexane + ethylene glycol system at 298.15, 303.15, 308.15,
313.15, and 323.15 K, the immiscible area changed little with
the temperature rising, which indicated that the influence of
temperature on the mutual solubility of the system could be
Article
(1)
(2)
Figure 3. Separation factor versus mole fraction of n-butanol in
ethylene glycol phase for n-butanol + n-hexane + ethylene glycol
system: (□) 298.15 K; (○) 303.15 K; (△) 308.15 K; (▽) 313.15 K;
(☆) 323.15 K.
neglected. Figure 4 showed the variation of n-butanol with
ethylene glycol in ethylene glycol phase at different temper-
Figure 4. Relationship between n-butanol and ethylene glycol in
ethylene glycol phase at different temperatures: (□) 298.15 K; (○)
303.15 K; (△) 308.15 K; (▽) 313.15 K; (☆) 323.15 K.
atures. It was seen that the linear relationships between n-
butanol and ethylene glycol were completely coincident, which
indicated that temperature had no effect on the equilibrium
concentration of n-butanol in ethylene glycol. Figure 5 gave the
relationship of n-butanol in ethylene glycol phase against in n-
hexane phase at different temperatures, which showed that the
relationship between n-butanol in two phases varied slightly
with the increasing temperature, however, the variations were
very small. The results indicated that temperature had a
minimal influence on the distribution of n-butanol in two
phases.
As shown in Figures 2 and 3, the variations of distribution
coefficient and separation factor with the temperatures were
given, respectively. For distribution coefficient, with the
increase of n-butanol content in the system, the effect of
temperature on the distribution coefficient decreases gradually.
For separation factor, the separation factor curve had almost no
change with increasing temperature. The results indicated that
D DOI: 10.1021/acs.jced.7b00577
J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data Article

energy parameters which could be obtained when the objective

Figure 5. Distribution curves of n-butanol in ethylene glycol phase
against that in the n-hexane phase at different temperatures: (□)
298.15 K; (○) 303.15 K; (△) 308.15 K; (▽) 313.15 K; (☆) 323.15 K.
the influence of temperature on n-butanol extraction was not
obvious.
function (OF) was minimized.
N 2 3
OF = ∑ ∑ ∑ (xijkexp‐xijkcal)2
k=1 j=1 i=1 (3)
where the subscripts i, j, and k represent to the component,
phase and tie-line, respectively; N represent to the number of
tie-lines; xexp cal
ijk and xijk were the experimental and calculated mole
fraction, respectively.
The volume and surface area parameters (r and q) for n-
butanol, n-hexane, and ethylene glycol in the UNIQUAC
model were listed in Table 3. The nonrandomness parameters
α in the NRTL model, which were listed in Table 4, were first
given according to the polarity of the mixture system.
Moreover, other NRTL model parameters were obtained by
correlating the LLE data.
The correlating data also were obtained when minimizing the
OF to get the model parameters. The agreement between the
experimental and correlating LLE data was judged by the root-
mean-square deviation (RMSD).

■
DATA CORRELATION
UNIQUAC and NRTL models are usually used to correlate
LLE data.20−25 Utilization of the two models has been reported
Table 3. Volume and Surface Area Parameters (r and q) in
the UNIQUAC Model
component r q
n-butanol 3.4543a 3.0520a
n-hexane 4.4998b 3.8560b
ethylene glycol 2.4086c 2.2479c
a
Reference 28. bReference 29. cReference 30.
for LLE in the ethylene glycol-containing systems. For instance,
Mohsen-Nia et al.26 measured the liquid−liquid equilibrium for
ternary mixtures of ethylene glycol + toluene + n-octane and
correlated these data using the NRTL and UNIQUAC model.
Aspi et al.27 reported the LLE data of cyclohexane + benzene +
dimethylformamide + ethylene glycol, and the regression data
obtained by NRTL model showed a good agreement with the
experimental data. In the mentioned literature,20−27 the
utilization of NRTL and UNIQUAC models in correlating
the LLE data obtained satisfactory regression results. Thus, in
the present work, NRTL and UNIQUAC models were used to
correlate the LLE data of n-butanol + n-hexane + ethylene
glycol system at 298.18−323.15 K. The regression software
Aspen Plus 7.2 was employed to obtain the binary interaction
⎧
⎪
N 2 3 (x exp‐x cal)2 ⎫
⎪
1/2
ijk ijk
RMSD = ⎨∑ ∑ ∑ ⎬
⎪ 6N ⎪
⎩k=1 j=1 i=1 ⎭ (4)
The temperature-independent binary interaction parameters
obtained when correlating the LLE data and the values of
RMSD were listed in Table 4. It could be seen that RMSD
values for NRTL and UNIQUAC models at 298.15−323.15 K
were 0.0347 and 0.0296, respectively, which indicated that the
LLE data for the studied system was correlated successfully, and
the UNIQUAC model with a smaller RMSD value showed a
better correlation performance.
In Figure 1 the phase diagrams for n-butanol + n-hexane +
ethylene glycol also showed the calculated LLE data from
NRTL and UNIQUAC models. It could be seen that there was
a certain error between the calculated and the experimental
value, but in general the phase diagrams demonstrated good
agreement at all five temperatures.
■ CONCLUSIONS
The LLE of ternary system n-butanol + n-hexane + ethylene
glycol was investigated at 298.15, 303.15, 308.15, 313.15, and
323.15 K under atmospheric pressure. The values of
distribution coefficient and separation factor were greater
than 1, which demonstrated that n-butanol extraction from n-
hexane−n-butanol solution using ethylene glycol as extractant
was feasible. The analysis results of the influences of n-butanol
content and temperatures on extraction showed that the
extraction capacity of ethylene glycol decreased with the
increase of n-butanol in the system, and temperature had little

Table 4. Binary Interaction Parameters of NRTL and UNIQUAC Models for n-Butanol + n-Hexane + Ethylene Glycol System at
(298.15-323.15) K

model i−j aij bij aji bji αij = αji RMSD

NRTL 1−2 1.914673 −160.301 −3.59362 887.3329 0.3 0.0347
1−3 −3.95705 628.6606 34.75851 −10000 0.3
2−3 −22.7673 10000 15.66035 −3224.31 0.2
UNIQUAC 1−2 −1.5663 706.8373 1.336 −610.719 0.0296
1−3 −3.83399 1718.345 −5.90885 −1113.9
2−3 −3.66388 −2081.99 1.963524 −1218.71

E DOI: 10.1021/acs.jced.7b00577
J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data Article

effect on extraction. Moreover, the experimental data were
correlated with NRTL and UNIQUAC models. The regression
results indicated that there were good agreement between the
calculated and the experimental data at all five temperatures,
and UNIQUAC model showed a better correlation perform-
ance.
(17) Nagata, I. Liquid-liquid equilibria for the acetonitrile + methanol
+ saturated hydrocarbon and acetonitrile + 1-butanol + saturated
hydrocarbon systems. Thermochim. Acta 1987, 114, 227−238.
(18) Dai, F. F.; Xin, K.; Song, Y. H.; Shi, M. D.; Yu, Y. M.; Li, Q. S.
Liquid-liquid equilibria for the extraction of phenols from alkane using
ethylene glycol. Fluid Phase Equilib. 2016, 409, 466−471.
(19) Shi, M. D.; He, G. Y.; Gan, F.; Yu, X. M.; Li, Q. S. Extraction of

■ AUTHOR INFORMATION
Corresponding Author
Low Concentration Aqueous Solution of Methylal: Liquid−Liquid
Equilibrium in Water + Methylal + (Cyclohexane and n-Heptane)
Ternary Systems. J. Chem. Eng. Data 2017, 62, 2183.
(20) He, G. Y.; Wang, L. P.; Shi, M. D.; Li, Q. S.; Yu, Y. M. Liquid−
*E-mail: licup01@163.com. liquid equilibria in the ternary systems {water + cyclopentanone +
benzene or toluene} at different temperatures: Experimental data and
ORCID
correlation. J. Mol. Liq. 2017, 236, 314−319.
Qingsong Li: 0000-0003-1425-8822 (21) Xin, K.; Song, Y. H.; Dai, F. F.; Yu, Y. M.; Li, Q. S. Liquideliquid
Notes equilibria for the extraction of furfural from aqueous solution using
different solvents. Fluid Phase Equilib. 2016, 425, 393−401.
The authors declare no competing financial interest. (22) Shen, Z. P.; Wang, Q. B.; Shen, B. W.; Chen, C. X.; Xiong, Z. H.

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F DOI: 10.1021/acs.jced.7b00577
J. Chem. Eng. Data XXXX, XXX, XXX−XXX