chemical engineering research and design 8 8 ( 2 0 1 0 ) 893–898

Contents lists available at ScienceDirect

Chemical Engineering Research and Design

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

Prediction of solute solubility in supercritical carbon

dioxide: A novel semi-empirical model

Sh. Jafari Nejad ∗ , H. Abolghasemi, M.A. Moosavian, M.G. Maragheh

School of Chemical Engineering, College of Engineering, University of Tehran, P.O. Box 11365-4563, Tehran, Iran

a b s t r a c t

Solubility data of solutes in supercritical fluids (SCF) are crucial for designing extraction processes, such as extraction
using SCF or micronization of drug powders. A new empirical equation is proposed to correlate solute solubility in
supercritical carbon dioxide (SC CO2 ) with temperature, pressure and density of pure SC CO2 . The proposed equation
is ln y2 = J0 + J1 P2 + J2 T2 + J3 ln  where y2 is the mole fraction solubility of the solute in the supercritical phase, J0 − J3 are
the model constants calculated by least squares method, P (bar) is the applied pressure, T is temperature (K) and  is
the density of pure SC CO2 . The accuracy of the proposed model and three other empirical equations employing P, T
and  variables was evaluated using 16 published solubility data sets by calculating the average of absolute relative
deviation (AARD). The mean AARD for the proposed model is 7.46 (±4.54) %, which is an acceptable error when
compared with the experimental uncertainty. The AARD values for other equations were 11.70 (±23.10), 6.895 (±
3.81) and 6.39 (±6.41). The mean AARD of the new equation is significantly lower than that obtained from Chrastil et
al. model and has the same accuracy as compared with Bartle et al. and Mèndez-Santiago–Teja model. The proposed
model presents more accurate correlation for solubility data in SC CO2 . It can be employed to speed up the process
of SCF applications in industry.
© 2010 The Institution of Chemical Engineers. Published by Elsevier B.V. All rights reserved.

Keywords: Supercritical carbon dioxide; Solubility; Empirical equation; AARD

1. Introduction is non-toxic, non-flammable, non-explosive and readily avail-

In the past two decades, there has been an increasing inter-
est in the use of supercritical fluids (SCFs) as an alternative
to the use of organic solvents in many industrial applications,
such as in chemical and biochemical reactions, extraction and
purification processes, particle production or, more recently,
in materials and polymer processing. Supercritical fluid tech-
nology is becoming increasingly popular in the chemical
and pharmaceutical areas. In addition to applications in
food, petroleum and chemical industries, there are a num-
ber of applications in the pharmaceutical industry including
particle size reduction of drugs, preparation of drug-loaded
microspheres and microemulsions (Dondeti and Desai, 1999;
Coimbra et al., 2005).
Carbon dioxide is the most commonly used supercritical
fluid. The critical temperature and pressure of carbon diox-
ide are relatively low (304 K and 73.7 bar, respectively) and it
able at low cost (Lucien and Foster, 2000).
Supercritical fluid extraction (SFE) using an extractant
supercritical CO2 mixture instead of an extractant–organic sol-
vent mixture has recently been recognized to be promising as
an advanced method for separation of metals from liquid sam-
ples or even from solid samples for the purpose of analytical
pretreatment or hydrometallurgy. Hence, an increasing num-
ber of studies on the development of SFE of metals (Furton
et al., 1995; Lin et al., 1995; Smart et al., 1997; Wang and Wai,
1996; Toews et al., 1996; Laintz and Tachikawa, 1994; Iso et al.,
1995; Meguro et al., 1996) is available. One of several important
advantages of SFE is that extraction efficiency and extraction
selectivity can be enhanced by tuning the pressure and/or
temperature. Also, SFE can minimize the amount of solvent
waste. Examples of SFE applications include, e.g., an SFE
method for the separation of metal ions such as uranium(VI)
and fission product elements from nitric acid solution into

∗
Corresponding author. Tel.: +98 9111842269.
E-mail address: shjn20@yahoo.com (Sh. Jafari Nejad).
Received 5 July 2009; Received in revised form 8 December 2009; Accepted 9 December 2009
0263-8762/$ – see front matter © 2010 The Institution of Chemical Engineers. Published by Elsevier B.V. All rights reserved.
doi:10.1016/j.cherd.2009.12.006
894 chemical engineering research and design 8 8 ( 2 0 1 0 ) 893–898

a supercritical fluid, mixed solutes in a supercritical fluid and

Nomenclature a single solute in mixed supercritical fluids or supercritical
fluid plus an organic solvent. Different aspects of the solubil-
AARD average-absolute-relative deviation ity of mixed solutes in supercritical carbon dioxide (SC CO2 )
A , B and C constants in Eq. (5) have been reviewed recently (Lucien and Foster, 2000). In this
˛ , ˇ , k constants in Eq. (2) work, the solubility of a solute in SC CO2 has been considered.
˛1 , ˛2 , C constants in Eq. (4) Different equations have been presented for mathematical
˛ and ˇ the model constants in Eq. (8) modeling of solubility data in SC CO2 . One can categorize
˙˛H 2 effective hydrogen bond acidity these models into two groups, theoretical or semi-empirical
B0 − B3 constants in Eq. (3) equations (similar to models based on equations of state) and
˙ˇ2H effective hydrogen bond basicity empirical equations (such as density based equations).
C0 − C5 the curve-fitting parameters in Eq. (6) Models derived from equations of state need complicated
D0 − D5 the model constants in Eq. (7) computational procedures that are not provided in commonly
E enhancement factor (Py2 /P2 ) used commercial software. Also, these models employ the
H sum of the enthalpies of vaporization and sol- solute properties, such as critical properties, acentric factor,
vation of solute (J mol−1 ) molar volumes and vapor pressure, which often cannot be eas-
Hsub enthalpy of sublimation of the solute (J mol−1 ) ily determined experimentally. The numerical values of the
IARD individual absolute relative deviations solute properties can affect solubility predictions using mod-
J0 − J3 constants in Jafari Nejad et al. model, Eq. (11) els derived from equations of state. For example, Garnier et
LSER linear salvation energy relationship al. (1999) investigated the effect of different numerical values
M0 − M5 the model constants in Eq. (10) of sublimation pressure estimated or collected from the liter-
N the number of experimental data points ature, on solubility predictions using thermodynamic models
P pressure (bar) based on cubic equations of state. The authors demonstrated
P2 sublimation pressure of solute (bar) that the large deviations between experimental and calculated
Pref standard pressure of 1 bar solubilities are due to an error in sublimation pressure. Using
p, q constants in Eq. (1) 21 data sets of hydrocarbon solubilities in SC CO2 , the average
 density (kg m−3 ) percentage error lies between 15.3% and 35.1% (Garnier et al.,
ref a reference density assumed as 700 kg m−3 1999).
R reduced density The empirical models are based on simple error minimiza-
R ideal gas constant (J mol−1 K−1 ) tion using least squares method and, for most of them; there
2∗ the dipolarity/polarizability is no need to use physicochemical properties. In this study,
S solubility (kg m−3 ) our focus was on calculating the solubility of a single solute in
SFE supercritical fluid extraction SC CO2 using empirical models and a new empirical equation
SCF supercritical fluid is presented. The accuracy of this and previously published
SC CO2 supercritical carbon dioxide models are critically examined using 16 solubility data of dif-
T temperature (K) ferent compounds in SC CO2 . The results demonstrated that,
TR reduced temperature by using the proposed equation, accurate solubility calcula-
Vx McGowen’s intrinsic volume for the solute (m3 ) tions using readily available independent variables (pressure,
V2 the molar volume of the solid (m3 mol−1 ) temperature and density of pure SC CO2 ) can be achieved.
WSCF molecular weight of supercritical fluid
(kg kg mol−1 ) 2. Theoretical
Wsolute molecular weight of solute (kg kg mol−1 )
y2 the mole fraction solubility of the solute in the The solubility (S) of the compound increases with increasing
supercritical phase density () of CO2 fluid, showing a linear relationship:
ycal
2 the calculated solubility of solute
exp
y2 the experimental solubility of solute
ln S = p ln  + q (1)
ı1 the solubility parameter of SC CO2 (bar0.5 )
ı2 solubility parameter of the solid (bar0.5 )
Chrastil (1982) derived an equation, which relates the sol-
ubility of a solute in a SCF with the density of the pure SCF
and the absolute temperature. This model is based on the
supercritical CO2 containing an organophosphorus extractant supposition that one molecule of solute, A, associates with
such as tributyl phosphate (TBP) or diisodecylphosphoric acid k molecules of solvent, B, to form a solvate-complex ABk ,
(DIDPA) (Iso et al., 1995; Meguro et al., 1996). in equilibrium with the system. The definition of the equi-
Solubility data in supercritical fluids are important infor- librium constant, obtained through several thermodynamic
mation for the design of extraction process. Mathematical considerations, leads to the following expression for the solute
modeling of solubility data in supercritical fluids could also solubility:
provide better understanding of the dissolution phenomenon
and can be used for solubility prediction at interested pres- ˛
sures and temperatures after measuring a minimum number ln S = k ln  + + ˇ (2)
T
of experimental data, which could speed up the development
of a supercritical fluid process. In this expression, S (kg m−3 ), is the solubility of the solute
In the mathematical modeling of solubility data in super- in the supercritical phase,  (kg m−3 ), the density of the pure
critical fluids, one should keep in mind that the solubility supercritical fluid, k the association number, ˛ a constant,
systems can be categorized in three groups, a single solute in defined as H/R (where H is the sum of the enthalpies of
 chemical engineering research and design 8 8 ( 2 0 1 0 ) 893–898 895

vaporization and solvation of the solute and R the gas con-
stant) and ˇ is another constant related to the molecular
weight of the solute and solvent. The parameters, k, ˛ and
ˇ are obtained by performing a multiple linear regression on
the experimental solubility data.
Del Valle and Aguilera (1988) then added one more term to
Eq. (2). The resulting equation is:
B1 B3
ln S = B0 + + B2 ln  + 2 (3)
T T
where B0 − B3 are the model constants.
Although  is a function of temperature and pressure, the
individual pressure term is not included in Eqs. (2) and (3).
Therefore, it is expected that those equations produce less
reliable results for solubility data at different pressures and
should be used at isobaric conditions.
Bartle et al. (1991) proposed a simple density-based semi-
empirical model to correlate the solubility of solute in SCF:
 yP  ˛2
ln = ˛1 + + C( − ref ) (4)
Pref T
where Pref is assumed as a standard pressure of 1 bar, ref is
a reference density assumed as 700 kg m−3 and ˛1 , ˛2 and C,
are empirical constants. In this model, the parameter ˛2 is
related to the enthalpy of sublimation of the solute, Hsub , by
the expression Hsub = −R˛2 , where R is the gas constant.
Based on the theory of dilute solutions, Mèndez-Santiago
and Teja (2000) proposed a simple linear expression to corre-
late the solubility of solutes in a SCF:
T ln(yP) = A + B  + C T (5)
where A , B and C are constants, considered as temperature
independent, and obtained by a multiple linear regression of
solubility experimental data.
The next model correlates the mole fraction solubility of a
solute (y2 ) with pressure (P, bar) and temperature (T K) (Yu et
al., 1994). The model is:
where E is enhancement factor (Py2 /P2 ) in which P2 is subli-
mation pressure of the solute, V2 is the molar volume of the
solid, ı1 is the solubility parameter of SC CO2 , ı2 denotes the
solubility parameter of the solid, R is the universal gas con-
stant, and ˛ and ˇ are the model constants calculated using
the least squares technique.
Bush and Eckert (1997) proposed a linear salvation energy
relationship (LSER) for predicting enhancement factor in SC
CO2 :
log E = −1.04 + 5.14Vx − 2.88TR Vx + 1.16R + 0.52R 2∗
 
− 0.11R + 0.83TR ˛H
2 − 0.22R ˛H
2

+ 0.70R ˇ2H (9)
where the independent variables are Vx , denotes McGowen’s
intrinsic volume for the solute, TR , reduced temperature, R ,
H
reduced density, 2∗ , the dipolarity/polarizability, ˛2 , the
H
effective hydrogen bond acidity and ˇ2 , the effective hydro-
gen bond basicity. The main disadvantage of the LSER model
is that the numerical values of the model variables are not
available for most of the compounds of interest (such as phar-
maceuticals). Also, Toews et al. (1996) reported an average
error of ≈56% for solubility calculations. Since Eqs. (8) and
(9) require physicochemical properties, such as P2 , ı2 or V2 ,
which are not readily available and calculating these parame-
ters using group contribution methods or other computational
techniques would cause other error sources, these models
were not included in this work.
Jouyban et al. (2002) proposed another empirical model.
The model is:
M4 T
ln y2 = M0 + M1 P + M2 P2 + M3 PT + + M4 ln  (10)
P
where M0 − M5 are the model constants and  is the density of
pure SC CO2 at different pressures and temperatures.
Reviewing published experimental solubility data in SC CO2
and previously presented models indicate the existence of:

(a) Non-linear relationship between ln y2 and pressure in

y2 = C0 + C1 P + C2 P2 + C3 PT(1 − y2 ) + C4 T + C5 T 2 (6)
isothermal conditions.
(b) Non-linear relationship between ln y2 and temperature in
where C0 − C5 are the curve-fitting parameters and (1 − y2 ) rep-
isobaric conditions.
resents the mole fraction of the solvent (supercritical carbon
(c) Linear relationship between ln y2 and ln  in a certain
dioxide). This model employs a function of the dependent vari-
range of pressure and temperature.
able (y2 ) as an independent variable (PT(1 − y2 )). This means
that in order to calculate y2 at a given temperature and pres-
sure, one should know y2 values. Considering the terms mentioned and in order to provide
Gordillo et al. (1999) proposed another empirical model. more accurate solubility calculations, the following empirical
The model is: equation is proposed:

ln y2 = D0 + D1 P + D2 P2 + D3 PT + D4 T + D5 T 2 (7) ln y2 = J0 + J1 P2 + J2 T 2 + J3 ln  (11)

where J0 − J3 are the model constants and obtained by least

where D0 − D5 are the model constants. The superiority of Eq.
squares method from experimental solubility data,  (kg m−3 )
(7) over Eqs. (4)–(6) has been shown using penicillin G solubility
is the density of pure SC CO2 at different pressures (bar) and
data in SC CO2 (Ziger and Eckert, 1983).
temperatures (K) and y2 is the mole fraction. Solubility of a
Ziger and Eckert (1983) used a solution model, based on the
solute is calculated by means of Eq. (12):
regular solution theory to correlate the enhancement factor in
supercritical fluids:
MWsolute y2
S= (12)
   MWSCF (1 − y2 )
V2 (2ı1 ı2 − ı21 ) ı 2
ln E = ˛ − ln 1− 1 +ˇ (8)
RT P
where in this equation S (kg m−3 ) is the solute solubility.
896 chemical engineering research and design 8 8 ( 2 0 1 0 ) 893–898

Table 1 – The details of solubility of solutes in supercritical carbon dioxide collected from the literature.
System no. Solute Refs. Number of data Temperature (K) Pressure (bar)
points (N)

1 Tributylphosphate (TBP) Our experimental 24 303.15–363.15 150–250

2 Diisodecylphosphoric acid (DIDPA) Our experimental 9 313.15–343.15 150–250
3 4,4-Diaminodiphenylmethane (DADPM) Khimeche et al. (2007) 27 313.15–333.15 110–200
4 1,5-Naphthalenediamine (1,5-NDA) Khimeche et al. (2007) 27 313.15–333.15 110–200
5 O-Phtalic acid Tian et al. (2007) 15 308.15–328.15 80–210
6 P-Aminobenzoic acid Tian et al. (2007) 15 308.15–328.15 80–210
7 Spiroindolinonaphthoxazine Coimbra et al. (2005) 21 308–328 105–256
photochromic dye
8 Irgacure® 2959 Coimbra et al. (2008) 21 308.2–328.2 101–256
9 N-Phenylacetamide Huang et al. (2007) 24 308.2–328.2 104.4–225
10 2-Methyl-N-phenylacetamide Huang et al. (2007) 21 308.2–328.2 121.6–225
11 4-Methyl-N-phenylacetamide Huang et al. (2007) 21 308.2–328.2 121.6–225
12 Rosuvastatin (RV) Hojjati et al. (2007) 45 308–348 121.6–354.6
13 Simvastatin (SV) Hojjati et al. (2007) 45 308–348 121.6–354.6
14 Atorvastatin (AV) Hojjati et al. (2007) 45 308–348 121.6–354.6
15 Lovastatin (LV) Hojjati et al. (2007) 45 308–348 121.6–354.6
16 Fluvastatin (FV) Hojjati et al. (2007) 45 308–348 121.6–354.6

The individual absolute relative deviations (IARD) of calcu- experimental data are correct. In this study, just the solubility
lated solubilities from observed values are used as an accuracy data of TBP (Jafari Nejad et al., 2009) and DIDPA are our experi-
criterion to compare the calculated solubilities with experi- mental data which the DIDPA solubility data is not published.
mental values. IARD was calculated by: It should be noted that in this study the constants of differ-
ent models are calculated by least squares method. Jouyban
 exp 
|ycal
2 − y2 |
et al. obtained an equation empirically from correlating den-
IARD (%) = 100 exp (13)
y2 sity of pure SC CO2 data at 80–450 bar and 300–450 K collected
from Angus et al. (1976). In this study, density of pure SC CO2
The average-absolute-relative-deviation (AARD), defined obtained from Jouyban et al. (2002) equation.
as:
4. Results and discussion
100  |ycal − yexp |
2 2
AARD (%) = exp (14)
N y2 In Table 2 different parameters (J0 − J3 ) and AARD (%), for
16 experimental data sets produced by our model by least
In this equation, N is the number of experimental data squares method, are presented.
exp
points, ycal
2 is the calculated solubility and y2 is the exper- In Table 3 AARDs for 16 experimental data sets produced
imental solubility data point. by various equations studied are presented.
Careful examination of Table 3 reveals that the proposed
3. Materials and methods model is more accurate and in some cases has the same
accuracy as compared with previously published empiri-
The available solubility data (in mole fraction) of compounds cal equations. The mean differences between global AARD
have been collected from the literature. The details of the data (=(AARD)/(total number of data sets)) for the proposed model
and their references are listed in Table 1. and previously published equations are statistically signifi-
In order to compare the accuracy of the proposed cor- cant. Some data sets (such as system number 16) produced
relation with the other models, it is assumed that all the relatively high AARD values for all models and others pro-

Table 2 – Different parameters (J0 − J3 ) and AARDs (%), for 16 experimental data sets produced by our model.
System no. Solute J0 J1 J2 J3 AARD (%)

1 Tributylphosphate (TBP) −10.83525 −6.44 E−6 1.65 E−5 1.01405 5.92

2 Diisodecylphosphoric acid (DIDPA) −82.52018 −2.46 E−6 6.94 E−5 10.44314 6.03
3 4,4-Diaminodiphenylmethane (DADPM) −45.69125 −8.4 E−7 8.46 E−5 4.218746 10.19
4 1,5-Naphthalenediamine (1,5-NDA) −39.69028 8.14 E−7 6.8 E−5 3.220887 7.37
5 O-Phtalic acid −23.84588 2.89 E−6 3.41 E−5 1.187063 8.01
6 P-Aminobenzoic acid −22.23137 2.41 E−6 2.83 E−5 1.051885 6.37
7 Spiroindolinonaphthoxazine photochromic dye −77.14035 2.37 E−6 0.000114 7.843147 6.91
8 Irgacure® 2959 −48.00923 1.56 E−6 9.83 E−5 4.353167 2.46
9 N-Phenylacetamide −42.99189 7.37 E−6 0.00011 3.498502 7.80
10 2-Methyl-N-phenylacetamide −70.55891 5.82 E−6 0.000164 6.769209 4.60
11 4-Methyl-N-phenylacetamide −56.34128 1.02 E−6 0.000135 5.117291 6.50
12 Rosuvastatin (RV) −51.88155 2.34 E−6 7.83 E−5 5.046358 8.87
13 Simvastatin (SV) −59.20337 4.18 E−6 8 E−5 6.180793 10.01
14 Atorvastatin (AV) −77.03011 5.45 E−6 0.000136 7.978313 10.08
15 Lovastatin (LV) −34.45827 −1.27 E−6 5.64 E−5 2.786027 6.26
16 Fluvastatin (FV) −51.98193 6.41 E−6 9.42 E−5 4.818774 12.00
 chemical engineering research and design 8 8 ( 2 0 1 0 ) 893–898 897

Table 3 – AARD for 16 experimental data sets produced by various equations.

System no. AARD (%) for AARD (%) for Chrastil AARD (%) for AARD (%) for Mèndez-Santiago
our model et al. model Bartle et al. model and Teja model

1 5.92 7.63 8.65 6.89

2 6.03 6.30 7.64 10.09
3 10.19 7.76 9.79 1.94
4 7.37 1.81 8.12 1.06
5 8.01 9.23 8.10 4.79
6 6.37 7.34 7.96 3.85
7 6.91 7.90 6.60 6.30
8 2.46 3.30 5.30 4.70
9 7.80 6.82 5.80 4.82
10 4.60 5.56 4.17 7.33
11 6.50 6.69 6.49 6.42
12 8.87 18.50 4.1 7.4
13 10.01 21.70 7.00 10.10
14 10.08 34.80 3.60 8.40
15 6.26 14.30 6.30 5.40
16 12.00 27.60 10.70 12.80

Mean (%) 7.46 11.70 6.895 6.39

Fig. 1 – Mean (global) AARD values for different equations.
duced lower AARD values. The global AARD values for 16 data
sets are shown in Fig. 1. The mean AARD for the proposed
model is 7.46 (±4.54) %, which is an acceptable error when
compared with the experimental uncertainty. The AARD val-
ues for other equations were 11.70 (±23.10), 6.895 (±3.81) and
6.39 (±6.41). The mean AARD of the new equation is signif-
icantly lower than that obtained from Chrastil et al. model
and has the same accuracy as compared with Bartle et al and
Mèndez-Santiago–Teja model (In other words, there are no sig-
nificant differences between the global AARD for the proposed
model, Bartle et al. model and Mèndez-Santiago–Teja model).
The proposed model presents more accurate correlation for
solubility data in SC CO2 . It can be employed to speed up the
process of SCF applications in industry.
5. Conclusion
In conclusion, the proposed model produces reasonably accu-
rate correlation of the mole fraction solubility of solutes in
SC CO2 with respect to pressure, temperature and density of
pure SC CO2 . The independent variables (P, T and ) are readily
available. The model is applicable for interpolation of unmea-
sured solubility data after training the model by calculating
the model constants. The model can also be utilized to screen
experimental solubility data to detect possible outliers.
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