Fluid Phase Equilibria 268 (2008) 153–158

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Fluid Phase Equilibria

journal homepage: www.elsevier.com/locate/fluid

Molecular connectivity indices method for correlating and

estimating solubility of fatty acids, alcohols, esters and
triglycerides in supercritical carbon dioxide
Hongru Li, Shufen Li ∗
Key Laboratory for Green Chemical Technologies of the Ministry of Education, School of Chemical Engineering and Technology,
Tianjin University, No. 92#, Weijin Street, Tianjin C.P. 300072, PR China

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

Article history: A new method to correlate and estimate the solubility of fatty acids, alcohols, esters and triglycerides
Received 14 January 2008 in supercritical CO2 is proposed. This method is based on the idea of molecular connectivity indices and
Received in revised form 19 March 2008 Chrastil’s equation. The Chrastil’s equation was used to correlate the solubility of solutes in supercriti-
Accepted 20 March 2008
cal CO2 and the parameters in Chrastil’s equation were expressed as the linear functions of the solutes’
Available online 28 March 2008
molecular connectivity indices. This method proves to be simple because only knowledge on the chemi-
cal structure of the solute is needed. The results showed that the correlation coefficient was higher than
Keywords:
0.9662 in the correlation and the solubility can be predicted on an order-of-magnitude basis.
Molecular connectivity indices
Solubility © 2008 Published by Elsevier B.V.
Supercritical carbon dioxide
Correlation
Estimation

1. Introduction
Potential applications of supercritical fluid (SCF) technology in
the processing of fats and oils have been extensively studied over
the last three decades. Early research focused mainly on the extrac-
tion of oil from seeds [1–3] and at present the research on oil points
to strong interest in purification and fractionation with SCFs [4–6].
Besides, SCFs are also used as reaction media in recent investiga-
tions [7–10].
Knowledge on the solubility of materials in the supercritical
solvents is beneficial for the design of any SCF process. As the
experimental approach is time consuming and the reliability of
the results depends strongly on the purity of samples and the
experimental techniques [11], estimation models are still required.
Several correlations have been developed in order to correlate and
extrapolate solubility data at various pressures and temperatures.
The equation of state (EOS) method [12–17], where the SCF is
treated as a high-pressure gas, and the solubility parameter method
[18,19], where the SCF is treated as a liquid, have a strong the-
oretical basis. However, there are some limitations in their use,
e.g., the absence of the physicochemical properties of the pure
solute such as sublimation pressure, critical properties and acen-
∗ Corresponding author. Tel.: +86 22 27402720; fax: +86 22 27402720.
E-mail address: shfli@tju.edu.cn (S. Li).
tric factor, fusion enthalpy, melting point, solid molar volume and
liquid molar volume. The physicochemical properties of solutes are
often obtained by estimation, which causes errors in the solubil-
ity prediction. Besides, these theoretical methods are based on the
assumption that the solute is solid. But in some cases, the melting
point of the solid decreases with increasing pressure because of the
solubility of the supercritical solvent in the melt phase. Bamberger
et al. [20] found that for some fatty acids and triglycerides, their
melting point is depressed under pressure in CO2 . Nilsson and Hud-
son [21] also observed a melting point depression for tripalmitin.
In this case, the dissolution of supercritical CO2 in the solutes can-
not be neglected and the prediction of solubility with theoretical
methods is more difficult.
Thermodynamic models based on the cluster solvation con-
cept [22–26] were applied for correlating the solubility of solid in
supercritical fluid. These methods show satisfactory results. The
semi-empirical approach, Chrastil’s model, which is one of the
cluster solvation models, correlates solubility as the function of
temperature and density of supercritical solvent [25,26]. It is simple
and has a wide range of application because it does not require any
physicochemical property data for the solute. Satisfying correlation
results can be achieved with Chrastil’s equation for both solid and
liquid solutes. Recently, a group contribution method was used to
correlate the parameters in Chrastil’s equation [27]. This method is
simple and avoids complicated calculations of solubility. However,
it is based on the assumption that the same group, such as methyl or

0378-3812/$ – see front matter © 2008 Published by Elsevier B.V.

doi:10.1016/j.fluid.2008.03.014
154 H. Li, S. Li / Fluid Phase Equilibria 268 (2008) 153–158

methylene group, in different molecules has an equal contribution of molecular structure that encodes degree of skeletal branching
to the values of parameters in Eq. (1). This assumption neglects the [39]. The expressions for the simple connectivity index 1  and the
effect of microchemical environment around the groups, so errors valence connectivity index 1 v are as follows:
are inevitable using this assumption.
The objective of this study was to develop a new method to  −1/2
1
estimate the parameters of Chrastil’s equation with molecular con- = (ıi ıj )k (2)
nectivity indices (MCIs), which are based on the chemical structure k

of the solute. The solubility of fatty acids, fatty alcohols, fatty

acid esters and triglycerides were correlated and estimated with
 −1/2
1
v = (ıvi ıvj ) (3)
Chrastil’s equation and MCIs. k
k

2. Methods
ıi is the number of non-hydrogen atoms to which the non-hydrogen
atom i is bonded. If ıi is replaced by ıvi , which is modified to
Experimental solubility data were collected from literature
incorporate multiple bonding, heteroatoms and valence states and
(listed in Table 1) for the following systems: fatty acid systems
calculated by the method proposed by Kier and Hall [37–39], the
containing lauric acid (C12), myristic acid (C14), palmitic acid
valence connectivity index 1 v can be obtained.
(C16), oleic acid (C18:1), stearic acid (C18); fatty alcohol sys-
As the physicochemical properties of the solute such as size,
tems containing hexadecanol (C16–OH), octadecanol (C18–OH),
shape and vaporization enthalpy have quantitative relation with
eicosanol (C20–OH); fatty acid ester systems containing methyl
MCIs [36–38], the values of k, a and b in Chrastil’s equation are
oleate (mC18:1), methyl linoleate (mC18:2), EPAEE (eC20:5),
assumed to have relations with MCIs of the molecule, which was
DHAEE (eC22:6); triglyceride systems containing trilaurin (LLL),
observed by Jin et al. [40] for aromatic compounds. However, if
trimyristin (MMM), tripalmitin (PPP), triolein (OOO), and tri-
each parameter, such as k, a, b, in Eq. (1) is expressed as function
caprylin (CCC).
of MCIs, more parameters would be introduced. As a result, more
Modelling of these data was carried out using a density based
solubility data of the solutes in a homologous series should be pro-
correlation as proposed by Chrastil [25]. Chrastil’s equation is based
vided. Since the number of the solubility data for the solutes in a
on a cluster solvation model and can be expressed as follows:
homologous series is limited in the literature, the number of param-
a  eters in Chrastil’s equation is reduced by considering isothermal
ln s = k ln  + +b (1)
T solubilities. At constant temperature, Eq. (1) simplifies to Eq. (4).

where s is the solubility of the solute (g/L),  is the density of SC-

ln s = k ln  + Q (4)
CO2 (g/L), and T is the temperature (K). Chrastil’s equation is based
on the assumption of a solvate complex formation between the
solute and CO2 molecules and parameter k is the number of CO2 As the solvent is supercritical CO2 for all the solutes studied
molecules in the solvate complex. Parameter a is dependent on the in this paper, the values of k and Q are mainly related with the
total enthalpy of the reaction, which includes the vaporization and properties of the solute, which are determined by the structure of
solvation enthalpies of the solute. Parameter b is dependent on the the solute molecule. The values of k and Q in Chrastil’s equation are
molecular weight of the solute and the solvent and the association assumed to have a linear relationship with 1 v /f and 1 , where
constant. f stands for the number of functional groups of the solute. Under
MCIs () have been widely used as structure descriptors, which this assumption, the relation of the solubility and MCIs at constant
contain a large amount of information on the molecular struc- temperature is given by the following general expression:
tural features [36–39]. The most widely used MCIs for chainlike    
molecules are the first order connectivity indices: 1  and 1 v . 1 v 1 v
ln s =  ln  + ϕ (5)
The first order connectivity indices are the direct representation f, 1  f, 1 

Table 1 where (1 v /f, 1 ) and ϕ(1 v /f, 1 ) are linear functions of 1 v /f ,
The MCIs of fatty acids, fatty alcohols, fatty acid esters and triglycerides and the 1 and 1 v /f , 1 , respectively, and are used to express the polarity
references for solubility data used
and skeleton of the solute molecule [33–35].
Materials 1
 1
v 1
v /f References The linear functions (1 v /f, 1 ) and ϕ(1 v /f, 1 ) are regressed
Lauric acid 6.7700 5.9884 5.9884 [28] by multivariable linear regression using the solubility data and
Myristic acid 7.7700 6.9884 6.9884 [29,30] MCIs of the solutes with similar structure. Once the linear func-
Palmitic acid 8.7700 7.9884 7.9884 [29,31] tions are determined, the solubility of the solute, whose structure
Stearic acid 9.7700 8.9884 8.9884 [32]
is similar to the solutes used in regression, can be estimated by the
Oleic acid 9.7700 8.6382 4.3191 [33]
Hexadecanol 8.4142 8.0233 8.0233 [31] corresponding correlation with its MCIs. The regression results are
Octadecanol 9.4142 9.0233 9.0233 [32] determined by calculating the correlation coefficient (r) and the p
Eicosanol 10.4142 10.0233 10.0233 [32] value from the significance test. The estimation results are evalu-
Methyl oleate 10.3080 9.0270 4.5135 [34] ated using the average absolute relative deviation (AARD) between
Methyl linoleate 10.3080 8.1937 2.7312 [34]
Eicosapentaenoic acid 11.8080 9.2307 1.5384 [34]
the measured and calculated data. The AARD is defined as
ethyl ester (EPAEE)
 
1   sexp − scal 
Docosahexaenoic acid 12.8080 9.8637 1.4091 [34] N
AARD% =
 sexp  × 100
ethyl ester (DHAEE) (6)
Trilaurin 22.0275 19.6723 6.5774 [29] N
i=1
Trimyristin 25.0275 22.6723 7.5774 [29]
Tripalmitin 28.0275 25.6723 8.5774 [29]
Tricaprylin 15.0275 13.6723 4.5574 [35] Where N is the number of experimental data; sexp and scal are the
Triolein 31.0275 27.6218 4.6036 [26] experimental and calculated solubility.
 H. Li, S. Li / Fluid Phase Equilibria 268 (2008) 153–158 155

Table 2
The regression results of the solubility of fatty acids, alcohols, esters and triglycerides in SC-CO2 using MCIs and Chrastil’s equation

Components of the system Equation Temperature a b c d e f r pa

(K)

Myristic acid + palmitic acid + stearic acidb (7) 308 −6.8948 1.4579 0 0 −11.3977 68.8087 0.9811 0.10
Myristic acid + palmitic acid + stearic acidc (7) 308 3.8760 0.1382 0 0 −2.5749 −10.0062 0.9912 0.04
Myristic acid + palmitic acid + lauric acid (7) 313 −11.9994 2.4791 0 0 −18.3197 109.6376 0.9970 0.06
Myristic acid + palmitic acid + oleic acid + lauric (8) 313 −8.9448 2.1095 0 −11.7089 −4.3054 79.5182 1.0000 0.00
acid
Hexadecanol + octadecanol + eicosanolb (7) 308 1.5818 0.3108 0 0 −3.2493 2.3637 0.9920 0.02
Hexadecanol + octadecanol + eicosanolc (7) 308 4.5986 0.0347 0 0 −1.3715 −18.8319 0.9961 0.01
Methyl oleate + methyl (8) 313 13.1009 1.4577 0 −9.7033 −0.8610 −72.4369 0.9662 0.08
linoleate + EPAEE + DHAEE
Methyl oleate + methyl (9) 313 −32.4655 3.9344 3.4626 −25.9257 −23.6018 226.6460 0.9767 0.06
linoleate + EPAEE + DHAEE
Methyl oleate + methyl (8) 333 7.7436 0.0565 0 −0.4494 −0.3888 −41.8431 0.9670 0.03
linoleate + EPAEE + DHAEE
Methyl oleate + methyl (9) 333 −5.4543 0.5016 1.1232 −3.3283 −7.7354 44.3671 0.9710 0.03
linoleate + EPAEE + DHAEE
Hexadecanol + octadecanol + eicosanol + myristic (8) 308 −1.8881 0.7232 0 −1.1918 −5.0566 28.4601 0.9724 0.10
acid + palmitic acid + stearic acid
Hexadecanol + octadecanol + palmitic (8) 308 −5.6893 1.2655 0 −4.5862 −5.1532 52.6373 0.9917 0.03
acid + stearic acid
Hexadecanol + octadecanol + palmitic (8) 318 39.8342 −4.0598 0 28.6032 −2.2586 −255.6387 0.9878 0.03
acid + stearic acid
Hexadecanol + octadecanol + palmitic (8) 328 14.9905 −0.8240 0 6.7595 −1.7910 −91.1533 0.9863 0.05
acid + stearic acid
Hexadecanol + octadecanol + palmitic (8) 338 15.6636 −0.9283 0 6.9928 −1.3757 −94.9315 0.9905 0.05
acid + stearic acid
Trilaurin + trimyristin + tripalmitin + (9) 313 20.7394 0.6941 −0.6808 −6.2213 4.5007 −124.9721 0.9840 0.23
tricaprylin + triolein
a
p value is got from significance test.
b
All solubility data from the literature are included in the regression.
c
The low-pressure (P < 10 MPa) solubility data are excluded in the regression.

3. Results and discussion
3.1. Correlation with MCIs and Chrastil’s equation
The MCIs of the solutes were calculated with the method pro-
posed by Kier and Hall [36–38] and the results are listed in Table 1.
The solubility of fatty acids, fatty alcohols, fatty acid esters and
triglycerides was correlated using Eq. (5). The performance of the
regression models was evaluated with the correlation coefficient
(r) and the p value from the significance test. The regression results
are listed in Table 2.
For the homologous series of saturated fatty acid systems or
fatty alcohol systems, the solute can be distinguished by 1 v /f or
1 . So (1 v /f, 1 ) and ϕ(1 v /f, 1 ) in the general expression can
are also a reason for the poor regression results. In fact, there are
obvious differences between the solubility data of lauric acids from
different literature sources [28,29] when the pressure approaches
the critical points of CO2 . So the low-pressure solubility data, espe-
cially the data deviating from Chrastil’s equation, should be treated
with caution in the application of the proposed model. Besides, the
regression result also depends on the accuracy of the solubility data.
For the saturated fatty acid–unsaturated fatty acid, the saturated
fatty acid–fatty alcohol systems and the fatty acid ester systems
containing methyl oleate, methyl linoleate, eicosapentaenoic acid
ethyl ester (EPAEE) and docosahexaenoic acid ethyl ester (DHAEE),
regression analysis with the four-parameter-equation (Eq. (7)) can-

be expressed as function of 1 v /f or 1 . The expression is as follows:

 
a + b1 v
ln s = ln  + e1  + f (7)
f

The regression analysis was carried out using four-parameter-

equation (Eq. (7)) and the regression results for fatty alcohols were
satisfying, where the p value was 0.02 (Fig. 1). For the saturated
fatty acid systems containing myristic acid, palmitic acid and
stearic acid (Fig. 2) and the systems containing lauric acid, myristic
acid and palmitic acid, the p values were larger than 0.05. This
can be attributed to the inclusion of low-pressure solubility data.
Cluster formation does not take place on a large scale when the
pressure is low [41]. In this case, the low-pressure solubility data
do not fit Chrastil’s equation well since Chrastil’s equation is based
on a cluster solvation model. So regression with Eq. (7) cannot
give good results. If the low-pressure solubility data (P < 10 MPa)
were excluded in the regression, the results could be better not
only for fatty acid systems (p = 0.04) but also for fatty alcohol Fig. 1. Correlation results of the solubility of fatty alcohols in SC-CO2 with Eq. (7),
systems (p = 0.01). The experimental errors in the solubility data T = 308 K.
156 H. Li, S. Li / Fluid Phase Equilibria 268 (2008) 153–158

Fig. 2. Correlation results of the solubility of fatty acids in SC-CO2 with Eq. (7),
Fig. 4. Correlation results of the solubility of fatty acids and fatty alcohols in SC-CO2
T = 308 K.
with Eq. (8), T = 308 K.

not give good results. Satisfying results could be achieved when

the solubility was correlated with the five-parameter-equation (Eq.
(8)). The results are shown in Table 2, Figs. 3–5. Regression with the
six-parameter-equation (Eq. (9)) can only improve the correlation
results slightly while more solubility data will be needed in the
prediction. So Eq. (8) was preferred for these systems.
 
a + b1 v d1 v
ln s = ln  + + e1  + f
f f
 
a + b1 v d1 v
ln s = ln  + + e1  + f
f + c1  f fatty acid ester systems.
The correlation results improve when more parameters are
included in the equations. This phenomenon can be attributed to
the structure differences of the solutes. A single index of 1  or 1 v /f
is insufficient as a complete structure representation for the wide
range of structure features that occur in the molecules. So 1 v /f
and 1  are introduced simultaneously to express the parameter Q
in Chrastil’s equation. For the fatty acid ester systems, the regres-
sion results were less satisfying than for fatty acid–fatty alcohol
systems and the saturated fatty acid–unsaturated fatty acid sys-
tems because the structure of these solutes is more complicated
due to the existence of multi-unsaturated bonds.
The solubility of triglyceride systems containing trilaurin,
trimyristin, tripalmitin, tricaprylin and triolein were regressed with
the six-parameter-equation (Eq. (9)). The regression results (Fig. 6)
were not as good as for the fatty acid, fatty alcohol and fatty acid
ester systems. This can be explained by the complex structure of
triglycerides. The first order MCIs of 1 , 1 v and the number of
functional groups f were insufficient to represent the wide range of
(8)
structure feature that occurs in these molecules. So it is concluded
that the expressions containing the first order MCIs are more suit-
(9) able for chainlike molecule systems such as fatty acid, fatty alcohol,
The results of above correlation shows that the four-parameter-
equation (Eq. (7)) can be used to correlate the solubility of
homologues systems such as fatty acid and fatty alcohol systems;
the five-parameter-equation (Eq. (8)) can be used to correlate the
solubility of solutes with similar structures such as fatty acids and
fatty alcohols, saturated fatty acids and unsaturated fatty acids,
saturated fatty acid esters and unsaturated fatty acid esters; the
six-parameter-equation (Eq. (9)) can be used to correlate the solu-
bility of triglycerides but the correlation results are not as good as
for chainlike molecules such as fatty acids, fatty alcohols and fatty
acid esters.

Fig. 3. Correlation results of the solubility of fatty acids and unsaturated fatty acids Fig. 5. Correlation results of the solubility of fatty acid esters in SC-CO2 with Eq. (8),
in SC-CO2 with Eq. (8), T = 313 K. T = 313 K.
 H. Li, S. Li / Fluid Phase Equilibria 268 (2008) 153–158 157

Oleic acid: unpredictablec

Stearic acid
DHAEE

49.38
54.69

65.82

25.47
10.30
51.56
Stearic acid: 53.89
Stearic acid: 38.84
Lauric acid: 60.65
Lauric acid: 69.16
Eicosanol: 18.91
Eicosanol: 5.28

Palmitic acid
EPAEE

53.46

30.79

30.73
33.76
37.87
19.41
Estimation with MCIs and Chrastil’s equation ARRD%

Estimation with MCIs and Chrastil’s equation ARRD%

Estimation with MCIs and Chrastil’s equation ARRD%

Palmitic acid: 84.34
Palmitic acid: 42.60

Palmitic acid: 33.84

Palmitic acid: 45.72

Octadecanol: 12.56
Octadecanol: 6.70
Fig. 6. Correlation results of the solubility of triglyceride systems in SC-CO2 with

Methyl linoleate
Eq. (9), T = 313 K.

Octadecanol
50.49

22.05
12.89

30.19
41.52
47.37
At 308 K, the set of parameters for the family of fatty
acids (myristic acid + palmitic acid + stearic acid) differs from
the sets of parameters for two different combined systems:
(hexadecanol + octadecanol + palmitic acid + stearic acid) and

Myristic acid: 58.64

Myristic acid: 49.09
Myristic acid: 26.39
Myristic acid: 69.85
Hexadecanol: 15.80
(hexadecanol + octadecanol + eicosanol + myristic acid + palmitic

Hexadecanol: 7.71
The estimation results of the solubility of fatty acids, alcohols, esters and triglycerides in SC-CO2 using MCIs and Chrastil’s equation

acid + stearic acid), so is the case for the family of fatty alcohols

Unpredictablec
Unpredictable
Methyl oleate

Hexadecanol
(hexadecanol + octadecanol + eicosanol). The reason is that the
equations and solubility data used in regression are different. The
parameters in Eqs. (7)–(9) are sensitive to the change of the solu-

74.91
47.73
16.14
8.58
bility data set used in regression because the number of solubility
data for each solute is limited. So a separate set of parameters
for each family of compounds is preferred. The performance of a
simultaneous correlation of the complete set of data of all alcohols
Equation

Equation

Equation
and acids decreases slightly relative to that of the correlation of
(7)
(7)
(7)
(8)
(7)
(7)

(8)

(8)
the individual component.

3.2. Estimation with MCIs and Chrastil’s equation

Temperature (K)

Temperature (K)

Temperature (K)

The solubility is unpredictable when the prediction AARD is equal to or above 100.
In order to evaluate the estimation performance of above equa-

The low-pressure (P < 10 MPa) solubility data are excluded in the estimation.
tions, the solubility of each solute in a system (listed in Table 3)
was estimated by the solubility of the other solutes in the same
328
308
308

308
308

308

338
333
313
313

313

318

All solubility data from the literature are included in the estimation.
system. The estimation steps are as follows: first, the parameters
in the corresponding equations were regressed with the known
solutes’ solubility (excluding the solubility of the solute to be pre-
dicted) and MCIs; then, the solubility of this solute was calculated
by substituting its MCIs into the equations with known parame-
ters.
Myristic acid + palmitic acid + oleic acid + lauric acid

The estimation results are listed in Table 3. It can be seen that the
Methyl oleate + methyl linoleate + EPAEE + DHAEE

performance of estimation depends on the structural similarity of

the solutes in the system. For the saturated fatty acid systems, fatty
Myristic acid + palmitic acid + stearic acidb
a
Myristic acid + palmitic acid + stearic acid

alcohol systems and saturated fatty acid–fatty alcohol systems,

Myristic acid + palmitic acid + lauric acid

Hexadecanol + octadecanol + eicosanolb

Hexadecanol + octadecanol + eicosanola

whose structures were similar, the estimation errors (AARD%) were

Hexadecanol + octadecanol + palmitic

lower. For the saturated fatty acid–unsaturated fatty acid systems

and fatty acid ester systems, the estimation errors (AARD%) were
relatively higher. The estimation errors of oleic acid and methyl
Components of the system

Components of the system

Components of the system

oleate were quite large because the structure differences between

the solute estimated and the solutes used in parameter regression
acid + stearic acid

were large. The results reveal that the correlations proposed in this
paper are suitable for solubility estimation of the solutes whose
structures are similar to the solutes with known solubility. The
Table 3

estimation performance is equivalent with that of other method

a

[15–17,27].
158 H. Li, S. Li / Fluid Phase Equilibria 268 (2008) 153–158
4. Conclusions
The proposed method can correlate and estimate the solubility
of fatty acids, alcohols, esters and triglycerides in supercritical CO2
in the absence of experimental data. This method is based on the
idea of using molecular connectivity indices (MCIs) in combina-
tion with Chrastil’s equation. The correlation and estimation of the
solubility of solutes in supercritical CO2 only requires MCIs in the
calculations. The MCIs can be calculated easily once the molecular
structure of the solute concerned is known. The method is predic-
tive in nature and the solubility of solutes whose structure is similar
to the solutes with known solubility can be predicted. This method
proves to be simple because the physicochemical properties of the
solute, which are difficult to obtain by experimental methods, are
not needed. The correlation and estimation results of this method
are satisfying. The results showed that the correlation coefficient
was higher than 0.9662 in the correlation and the solubility can be
predicted on an order-of-magnitude basis.
List of symbols
a, b, c, d, e, f parameters defined in Eqs. (7)–(9)
f number of functional groups of the solute
k, a, b parameters defined in Eq. (1)
N number of experimental data
p value from the significance test
P pressure
Q parameters defined in Eq. (4)
r correlation coefficient
s solubility of the solute
sexp , scal experimental and calculated solubility
T absolute temperature
Greek letters
1
first order simple connectivity index of molecule
1 v first order valence connectivity index of molecule
ıi , ıj simple ı value of the atom i and j
ıvi , ıvj valence ı value of the atom i and j
 density of SC-CO2
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