Fluid Phase Equilibria 325 (2012) 2834

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Fluid Phase Equilibria

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Correlation and prediction of the solubilities of solid n-alkanes in supercritical

carbon dioxide using the CarnahanStarlingvan der Waals model with a
density-dependent parameter
Hongru Li a, , Shufen Li b , Bingqian Shen a
a
State Key Laboratory of Medicinal Chemical Biology and Tianjin Key Laboratory of Molecular Drug Research, College of Pharmacy, Nankai University, Tianjin 300071, PR China
b
Key Laboratory for Green Chemical Technologies of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, PR China

a r t i c l e i n f o a b s t r a c t

Article history: In this paper, the solubilities of some solid n-alkanes in supercritical carbon dioxide were correlated and
Received 26 January 2012 predicted using the CarnahanStarlingvan der Waals model with a density-dependent parameter of a12 .
Received in revised form 21 March 2012 It was found that the parameter values of a12 for solid n-alkanes in CO2 at different temperatures are equal
Accepted 4 April 2012
at the crossover pressure of 24 MPa, and a12 can be correlated with carbon number of the corresponding
Available online 13 April 2012
solid n-alkanes. At a given temperature, the linear t of parameters a12 versus the density of the solvent
was used for solubility correlation, resulting in an average absolute average relative deviation of 11.82%,
Keywords:
which is comparable with that of the PengRobinson equation of state combined with the van der Waals
Supercritical carbon dioxide
Solid n-alkanes
two-parameter mixing rule model. The regressed slope m and intercept n of the linear t can also be
CarnahanStarlingvan der Waals model correlated with the carbon number of solid n-alkanes. The solubilities of solid n-alkanes can be predicted
Solubility with a12 at the crossover pressure and slope m or with intercept n and slope m.
Prediction 2012 Elsevier B.V. All rights reserved.

1. Introduction
Supercritical uid technology has received widespread atten-
tion over recent years for its application in the extraction,
distillation, reaction, particle preparation, and waterless dyeing
processes. The solubilities of compounds used in the supercritical
process are the key parameters in process design. Experimentally
acquiring solubility data is time consuming and laborious. Thus, a
theory model that can estimate solubility data is highly desirable.
The compressed gas model is widely used in solubility cor-
relation and prediction [13]. In the compressed gas model, the
selection of the appropriate equation of state and mixing rule is
important [4,5]. The PengRobinson equation of state (PR-EOS),
combined with the classic van der Waals mixing rule, can be used in
the correlation. However, it encounters some difculty in solubility
prediction because parameters kij and lij , which are often used to
correct the asymmetry of the energy and shape of the unlike-pair
molecules, are empirical and do not follow trends based on phys-
ical properties [6,7]. These parameters must be correlated from
existing data, and the prediction of the solubility is sensitive to the
parameters [8].
In recent years, numerous mixing rules, such as the co-volume
dependent mixing rule [9,10], local composition mixing rules [7],
and EOS/Gex type mixing rules [11,12], have been proposed. How-
ever, all these rules require complicated calculations. In particular,
most mixing rules need the critical properties of solute, which are
difcult to acquire accurately. Furthermore, the mixing rule based
on the corresponding state of critical properties could not describe
the highly asymmetric system accurately [13].
Johnston and Eckert [13] proposed a model based on the
CarnahanStarlingvan der Waals (CSVDW) equation of state
(EOS). The CSVDW model can be used to predict the solubility of
naphthalene, phenanthrene, and anthracene in supercritical ethy-
lene when the reduced density of the solvent is above 1.5. The
advantage of this model is that only one meaningful parameter is
used, while the critical properties of solutes are avoided.
In this paper, the CSVDW model with a density-dependent
parameter of a12 was used to correlate and predict the solubili-
ties of some solid n-alkanes in supercritical carbon dioxide. This
model results in an average absolute average relative deviation
(AARD) comparable with that of the PR-EOS combined with the van
der Waals two-parameter mixing rule (PR-EOSVDW2) model. Fur-
thermore, the CSVDW model can predict the solubilities of solid
n-alkanes quantitatively.
2. Soliduid equilibria model

Corresponding author. Tel.: +86 022 23504368; fax: +86 022 23507760. For the binary system containing supercritical CO2 and solid
E-mail address: lihongru@nankai.edu.cn (H. Li). solute in the phase equilibria condition, the fugacity of the pure

0378-3812/$ see front matter 2012 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.uid.2012.04.004
 H. Li et al. / Fluid Phase Equilibria 325 (2012) 2834 29

solute (the supercritical uid is assumed to be insoluble in the The CSVDW-EOS is derived by replacing the repulsive term in the
solute phase) is equated to its fugacity in the supercritical phase. van der Waals equation with the CarnahanStarling hard sphere
model.
f S = f SCF (1)

 p  1 +  + 2 3 a
vS2 p = RT (14)
f2S = 2sat psat b (1 )
3 v2
2 exp RT
dp (2)
psat
2
where  is the reduced density of the uid and  = b /v. v is the
f SCF = y2 2 p (3) molar volume of the supercritical phase and can be calculated with
the method mentioned in the PR-EOSVDW2 model.
where 2sat is the fugacity coefcient of the pure solute and can be
For the binary system,
regarded as the unity, vS2 is the molar volume, psat 2
is the satura-
tion pressure of the solute at the given temperature, y2 is the mole b = y1 b1v + y2 b2v b1v (15)
fraction, and 2 is the fugacity coefcient of the solute in the super- where b1v and b2v are the van der Waals volumes of CO2 and solute,
critical solution. If the variation of the solute volume with pressure respectively. They can be calculated with the method proposed by
is neglected, the mole fraction of solute in the supercritical solution Bondi [15]. y1 and y2 are the mole fractions of CO2 and solute,
can be calculated by combining Eqs. (1)(3). respectively. As y2 is always much smaller than unity, it is assumed
2sat psat
2
exp(vS2 (p psat
2
)/RT ) that the repulsive parameter is strongly depended on the van der
y2 = (4) Waals volumes of CO2 (b1v = 19.7 cm3 mol1 ). For the attraction
2 p
parameter a, the mixing rule is
The fugacity coefcient of the solute in the supercritical solution 
2 can be calculated using PR-EOSVDW2 or CSVDW-EOS. a= yi yj aij (16)
The PR-EOS is i j
RT am
p= (5) According to the CSVDW model, the fugacity coefcient of the
v bm v2 + 2bm v b2m solute in the supercritical solution 2 can be expressed by the fol-
0.457235R2 Tc2 lowing equation:
a= (6)
pc 3 3 9 2 + 8 2(y1 a12 + y2 a22 ) pv
ln 2 = ln (17)
   (1 )
3 RT v RT
T
0.5 = 1 + (0.37464 + 1.54226 0.269922 ) 1 The y2 a22 term can be ignored if the solubility of the solute is
Tc
sufciently low and no specic interaction, such as a hydrogen
(7) bond between solute molecules, exists. By combining Eqs. (4) and
(17), the mole fraction of solute in the supercritical solvent can be
0.077796RTc expressed by the following:
b= (8)
pc
y2 p vS (p psat ) 3 3 9 2 + 8 2(1 y2 )a12 pv
where v is the molar volume of the supercritical phase. As the solute ln = 2 + + ln
psat RT (1 )
3 RT v RT
is innitely dilute in the supercritical phase, the molar volume of (18)
the supercritical CO2 can be used as the molar volume of super-
critical phase. The former can be calculated using Matlab programs
with the equation proposed by Stryjek and Vera [14]. Tc is the crit-
ical temperature, pc is the critical pressure, and is the acentric 3. Results and discussion
factor. The van der Waals two-parameter mixing rules are
 The solubilities of the solid n-alkanes in supercritical CO2 were
am = yi yj aij (9) analyzed by the CSVDW model. Solubility data of solid n-alkanes
i j have been reported in a lot of papers, but different papers reported
 different data [1619]. In this work, therefore, only the data with
bm = yi yj bij (10) high concentration and small difference have been adopted. The
i j properties of the solutes and the solubility references are listed in
 Table 1. Every experimental solubility datum was inserted in Eq.
aij = (1 kij ) ai aj (11) (18), and a corresponding a12 was calculated.
bi + bj Figs. 1 and 2 show the change in a12 with pressure for dotria-
bij = (1 lij ) (12) contane and tritriacontane in supercritical CO2 . The value of a12 is
2
shown to decrease with pressure. At a pressure of 24 MPa, the val-
where indices i and j refer to solute and supercritical uid, ues of a12 at different temperatures overlap. The change in a12 with
respectively, and kij and lij are two adjustable binary interaction pressure actually has a similar trend for all solid n-alkanes, whose
parameters. The fugacity coefcient of the solute in the supercritical solubilities in supercritical CO2 are reported in Refs. [1618]. a12
solution 2 is given by the following equation: represents the unlike-pair molecular interaction, and this inter-
 p(v b)

1 nb pv action is determined by the distance, motion, and collision of
ln 2 = ln + 1 the molecules. Hence, the pressure of 24 MPa can be regarded as
RT b n2 RT
crossover pressure.



a 1 1 n2 a 1 nb When the pressure is lower, the uid has higher compressibility,
+ and the temperature mainly affects the density of uid and the dis-
2 2bRT a n n2 b n2
tance of molecules. In this condition, higher temperature indicates
 
v + b(1 2) larger distance between the solute and the solvent molecules. In
ln (13) turn, this condition results in smaller repulsive forces and relatively
v + b(1 + 2)
larger attractive forces. Thus, a12 is larger at higher temperatures.
30 H. Li et al. / Fluid Phase Equilibria 325 (2012) 2834

Table 1
Properties of solid n-alkanes and solubility references.

Compounds Critical Critical pressurea , Acentric Molar volumeb , vS2 Temperature, Sublimation p range (Mpa) Solubility data
temperaturea , Tc pc (bar) factora , (cm3 mol1 ) T (K) pressurec , psub reference
(K) (bar)

CO2 304.2d 73.76d 0.255d

C24 H50 794.11 8.55 1.0422 423.794 308 2.73725E10 1024 [16]
310 4.563E10 12.945.9 [17]

C25 H52 801.84 8.16 1.0800 440.199 308 6.57585E11 1024 [16]
313 2.33383E10 15.236 [17]

C26 H54 809.94 7.80 1.1173 546.700 313 6.28108E11 13.841.3 [17]

C27 H56 816.36 7.47 1.1542 472.916 313 1.58246E11 1052.3 [17]
308 9.29777E13 1024 [16,18]

C28 H58 823.20 7.16 1.1907 489.353 313 4.06661E12 927.5 [18]
318 1.69799E11 1025 [16,18]
308 2.46793E13 1024 [16]

C29 H60 829.80 6.88 1.2268 505.737 313 1.07299E12 12.417.8 [17]
318 4.45436E12 1024 [16]

C30 H62 836.16 6.61 1.2625 522.185 308 5.4189E14 925 [18]
318 1.2172E12 10.525
308 3.15823E15 1024 [16]

C32 H66 848.26 6.14 1.3326 554.980 318 8.72554E14 1024

328 1.96904E12 1024
308 9.26218E16 1024 [16]

C33 H68 854.02 5.92 1.3671 570.211 318 2.49277E14 1024

328 5.48853E13 1024
333 2.40216E12 1024

C36 H74 870.27 5.36 1.4685 617.958 308 1.07277E17 1024 [16]
318 4.48385E16 1024
a
CGs method from Poling et al. [20].
b
Got from Ref. [21] and the data for hexacosane and heptacosane are interpolated with the data of other solid n-alkanes.
c
Got from Ref. [22] and the data for hexatriacontane are extrapolated with the data of other solid n-alkanes.
d
From Ref. [14].

With increased pressure, the solvent becomes sufciently dense
and less compressible, the repulsive force gradually dominates the
structure of the uid, and the distance between solute and solvent
is a near constant. In this condition, higher temperature implies
more intensive molecular motion and collision, resulting in weaker
unlike-pair molecular interaction. The effects of temperature on
the solutesolvent interaction indicate a tradeoff at the crossover
pressure. As the solid n-alkanes have similar structure and elec-
tron distribution, their sizes are much larger than carbon dioxide,
and therefore the interaction mode between the different solid n-
alkanes and the solvent around is almost the same. This is why the
crossover pressure is independent of the nature of solute here. The
values of a12 for the solid n-alkanes at the crossover pressure of
24 MPa are listed in Table 2.
Fig. 3 shows a linear relationship between the value of a12 at the
crossover pressure and the carbon number of the solute. Johnston
and Eckert [13] predicted the solubility of naphthalene, phenan-
threne, and anthracene in supercritical ethylene with a xed value
of a12 because this parameter is constant when the reduced density
of the solvent is above 1.5. However, this condition does not apply
to solid n-alkanes in supercritical CO2 . The value of a12 changes with
pressure and temperature, having a meeting point at the crossover
pressure of 24 MPa. To predict the solubility correctly, a suitable
a12 must be determined. As a12 represents the solutesolvent

Fig. 1. Parameter a12 in the CSVDW model versus pressure p for dotriacontane in Fig. 2. Parameter a12 in the CSVDW model versus pressure p for tritriacontane in
supercritical CO2 . supercritical CO2 .
Experimental data are reported in Ref. [16]. Experimental data are reported in Ref. [16].
 H. Li et al. / Fluid Phase Equilibria 325 (2012) 2834 31

Table 2
Values of a12 at the crossover pressure of 24 MPa for solid n-alkanes.

Compounds Na a12 (106 Mpa cm3 mol1 )

C24 H50 24 1.6126

C25 H52 25 1.6692
C28 H58 28 1.8495
C29 H60 29 1.9131
C32 H66 32 2.0981
C33 H68 33 2.1628
C39 H80 36 2.3653
a
Carbon number of solid n-alkanes.

Fig. 5. Parameter a12 in the CSVDW model versus density for tritriacontane in
supercritical CO2 .
Experimental data are reported in Ref. [16].

supercritical solvent.
 
y2 p vS (p psat ) 3 3 9 2 + 8 2(1 y2 ) 44,000m
v +n
ln sat = 2 +
p RT (1 )
3 RT v
pv
+ ln (20)
RT
The parameters m and n are evaluated by regressing the solubilities
Fig. 3. Parameter a12 in the CSVDW model versus carbon number N for solid n- of solid n-alkanes in supercritical CO2 with the AARD, as dened
alkanes in supercritical CO2 at 24 MPa. below, as the objective function.
Experimental data are reported in Ref. [16].  
100  y2 y2 
N exp cal
AARD% = exp % (21)
N y2
1
interaction determined by the distance of two molecules when
For comparison with the CSVDW model, the PR-EOSVDW2
temperature remains constant, thus, a12 may be correlated with the
model is used to correlate the solubilities of n-alkanes. Parame-
density of the supercritical solvent, which reects the distance of
ters kij and lij are regressed, with AARD as the objective function.
molecules indirectly. In Figs. 4 and 5, a12 exhibits a linear decrease
The results are shown in Table 3 and Figs. 6 and 7.
with the density of supercritical solvent at a given temperature.
The AARD of the CSVDW model is somehow bigger than that
Thus, the relationship between a12 and the density of the solvent
of the PR-EOSVDW2 model in correlation when the temperature
can be expressed as follows:
is higher and pressure is lower (corresponding to the lower density
44, 000 m of the solvent). But when the pressure is higher (corresponding
a12 = m + n = +n (19) to the higher density of the solvent), the CSVDW model gives
v
better correlation results. These results can be attributed to the
where  is the density of supercritical CO2 (kg cm3 ). A combina- simplication of the repulsive term in this model. The simplica-
tion of Eqs. (18) and (19) gives the mole fraction of solute in the tion is under the assumption that the solute does not signicantly
affect the excluded volume or the repulsive forces of the mixture
but this is not the case when the density of the supercritical sol-
vent is low [13]. When the density of the supercritical solvent is

Fig. 4. Parameter a12 in the CSVDW model versus density for dotriacontane in
supercritical CO2 . Fig. 6. Correlation results of the CSVDW model and the PR-EOSVDW2 model for
Experimental data are reported in Ref. [16]. tetracosane in supercritical CO2 at 310 K.
32 H. Li et al. / Fluid Phase Equilibria 325 (2012) 2834

Table 3
Correlation results of the PR-EOSVDW2 and CSVDW models.

Compounds Temperature, T PR-EOSVDW2 CSVDW Reference

kij lij AARD% m n AARD%

C24 H50 308 0.2467 0.3616 6.11 1206.57 2696800 7.08 [16]
310 0.2155 0.3332 8.78 1322.19 2836700 6.01 [17]

C25 H52 308 0.2436 0.3672 6.50 1304.88 2842800 6.99 [16]
313 0.2042 0.3223 3.48 1447.94 2974800 2.17 [17]

C26 H54 313 0.2107 0.3336 11.23 1551.51 3093000 6.09 [17]

C27 H56 313 0.2109 0.3422 16.32 1681.32 3254600 14.57 [17]

308 0.2333 0.3832 6.60 1594.72 3289400 6.71 [16]

308 0.1431 0.2445 35.67 2085.18 3680500 43.84 [18]
C28 H58 313 0.1752 0.2876 31.19 1942.57 3503700 35.34 [18]
318 0.2095 0.3414 8.40 1757.59 3325000 15.12 [16]
318 0.2002 0.3249 10.21 1784.54 3338400 13.94 [18]

308 0.2307 0.3862 7.39 1694.98 3434200 7.16 [16]

C29 H60 313 0.2164 0.3477 5.02 1795.09 3420400 4.88 [17]
318 0.2051 0.3453 8.32 1866.18 3479600 14.97 [16]

C30 H62 308 0.2518 0.4218 4.87 1695.66 3491000 5.54 [18]
318 0.2107 0.3666 9.26 1891.55 3580400 6.55 [18]

308 0.2006 0.3717 12.76 2095.47 3985900 12.34 [16]

C32 H66 318 0.1847 0.3439 14.23 2233.35 3977900 20.47 [16]
328 0.1809 0.3282 7.38a 2230.71 3847200 13.18a [16]

308 0.2040 0.3810 13.86 2175.76 4109500 13.01 [16]

C33 H68 318 0.1772 0.3413 16.58 2365.99 4150600 21.93 [16]
328 0.1700 0.3233 8.79a 2385.38 4035600 14.27a [16]

333 0.2000 0.3644 19.24a 2294.08 3913700 11.03a [16]

C36 H74 308 0.1798 0.3775 13.80 2549.34 4661000 12.08 [16]
318 0.1498 0.3309 14.16 2777.61 4701200 18.76 [16]

Average AARD% 10.59 11.82

a
Excluding the rst point in the data.

high, this simplication is more reasonable. It can be seen from
Figs. 6 and 7 that both of the two models show the retrograde
behavior of the solubility under high pressure. The difference is
that the CSVDW model shows a slighter retrograde behavior while
the PR-EOSVDW2 model shows a more drastic one. The slight ret-
rograde behavior of the CSVDW model can be explained by the
domination of the repulsive force between the solvent and solute
with the increasing of the solvents density. When the solvents
density is high enough (corresponding to the high pressure), the
solvent is relatively incompressible and the interaction between
the solvent and the solute is relatively stable. So the solubilities
of the solute would tend to be stable. The PR-EOSVDW2 model
gives a drastic retrograde behavior, which shows a big discrepancy
with the theory of association proposed by Chrastil [23]. The reason
may be that for the compressed gas model, the reference pressure
is nearly at zero (sublimation pressure of the solute), requiring the
PR equation of state to be accurate throughout the critical region
is a stringent requirement [6]. The CSVDW model, by reasonable
simplication of its repulsive term, is more suitable for the high-
pressure zone and can gives better correlation results.
Although the average AARD of the CSVDW model is slightly
bigger than that of the PR-EOSVDW2 model, the CSVDW model
has an advantage in that its m and n parameters show a linear
relationship with the carbon number of solid n-alkanes at a given
temperature (Fig. 8). For the PR-EOSVDW2 model, the parameters
are sensitive to the solubility data. The errors in solubility determi-
nation will result in a set of parameters without evident regularity
(Fig. 9). The linear relationship of parameters in the CSVDW model

Fig. 8. Parameters of m and n in the CSVDW model versus carbon number N for
Fig. 7. Correlation results of the CSVDW model and the PR-EOSVDW2 model for solid n-alkanes in supercritical CO2 at 308 K.
hexacosane in supercritical CO2 at 313 K. Experimental data are reported in Ref. [16].
 H. Li et al. / Fluid Phase Equilibria 325 (2012) 2834 33

Fig. 9. Parameters of kij and lij in the PR-EOSVDW2 model versus carbon number Fig. 11. Prediction results for heptacosane in supercritical CO2 at 313 K.
N for solid n-alkanes in supercritical CO2 at 308 K.
Experimental data are reported in Ref. [16].
pressure and slope m is that the value of a12 at the crossover pres-
Table 4
sure is independent of the temperature and only varies with the
Prediction results for solid n-alkanes. solute. By contrast, intercept n changes with temperature, even for
a specic solute. The prediction results, as presented in Table 4 and
Compounds AARD%
Figs. 10 and 11, are satisfactory. The CSVDW model can be used to
308 K 313 K 318 K predict the solubilities of solid n-alkanes quantitatively.
C24 H50 12.27 (7.79) [16]
C25 H52 7.45 (9.15) [16] 6.34 [17] 4. Conclusions
C26 H54 11.36 [17]
C27 H56 14.73 [17]
C28 H58 8.26 (15.42) [16] 43.44 (30.27) [16] The CSVDW model with a density-dependent parameter can
C29 H60 18.32 (30.70) [16] 5.34 [17] 42.75 (32.42) [16] be used to correlate and predict the solubilities of the solid n-
C30 H62 38.30(57.30) [18] 14.51(29.09) [18] alkanes in supercritical CO2 with only the sublimation pressure and
C32 H66 12.93 (21.89) [16] 43.36 (40.99) [16] solid molar volume of solute. In solubility correlation, the proposed
C33 H68 27.00 (37.53) [16] 43.13 (33.16) [16]
C36 H80 20.73 (10.57) [16] 41.62 (37.01) [16]
model results in an average AARD of 11.82%, which is comparable
with that of the PR-EOSVDW2 model. But in the high pressure
Predicted with a12 at the crossover pressure and slope m in the parentheses.
region, the CSVDW model gives better correlation results than
the PR-EOSVDW2 model according to the solubility data in Ref.
and the carbon number of solid n-alkanes at other temperatures are [17]. The CSVDW model avoids using the critical properties of the
as follows: solute and is predictive. For solid n-alkanes in supercritical CO2 , the
interaction parameter a12 is the linear function of the density of the
At 313 K, m = 87.058N + 709.829, r 2 = 0.948 (22)
solvent. Slope m and intercept n can be correlated with the carbon
2
n = 112445.714N + 177777.143, r = 0.970 (23) number of solid n-alkanes. At the crossover pressure of 24 MPa, the
2 values of a12 at different temperatures are equal and can also be
At 318K, m = 127.374N + 1824.881, r = 0.998 (24)
correlated with the carbon number of solid n-alkanes. The solubil-
2
n = 171609.709N 1496010.000, r = 0.999 (25) ities of solid n-alkanes can be predicted with a12 at the crossover
pressure and slope m or with intercept n and slope m.
The solubility of the solid n-alkanes in supercritical CO2 can be pre-
Although the parameters used in the proposed method are still
dicted by determining the value of a12 at the crossover pressure
correlated with the solubility data, the parameters are more mean-
(calculated from the linear regression in Fig. 3) and the slope m
ingful, and their trends of change are predictive. The CSVDW
or the slope m and intercept n (m and n are calculated from the
model is easy to use and can predict the solubilities of solid n-
linear regression with carbon number N of solid n-alkanes). The
alkanes in supercritical CO2 quantitatively.
advantage of predicting the solubilities with a12 at the crossover

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