Article pubs.acs.org/jced
Solubility of 4‑Hydroxybenzaldehyde in Supercritical Carbon Dioxide with and without Cosolvents Jun-su Jin,*,† Yi-wei Wang,† Hai-fei Zhang,‡ Xing Fan,† and Hao Wu*,§ †
Beijing Key Laboratory of Membrane Science and Technology, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, China ‡ Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, United Kingdom § High-Tech Research Institute, Beijing University of Chemical Technology, Beijing 100029, China ABSTRACT: The operating conditions of measuring the equilibrium solubility of 4-hydroxybenzaldehyde in supercritical carbon dioxide (SCCO2) were chosen at temperatures of (308, 318, and 328) K and five pressure points from (11.0 to 21.0) MPa, while the solubility data in SCCO2 with three different cosolvents (ethanol, ethyl acetate, and acetone) at 0.04 (mol·mol−1) were obtained at 318 K and the aforementioned pressure. The solubility of 4-hydroxybenzaldehyde revealed that the presence of cosolvents could greatly improve the dissolving ability of solvent. The solubilities of solutes with five kinds of functional groups substituted for the formyl group (−CHO) of 4-hydroxybenzaldehyde have been investigated on the aspects of melting point and intermolecular force. The data of 4-hydroxybenzaldehyde in pure SCCO2 were successfully correlated with three semiempirical models (Chrastil, Méndez-Santiago, and Teja (M-S-T) and Bartle models) for a deviation of (6.82 to 8.50) %, while the data with cosolvents were calculated by three different models (modified Chrastil, modified M-S-T, and Sovova models) for a deviation of (2.98 to 8.87) %. The thermodynamic properties of 4-hydroxybenzaldehyde were investigated.
■
INTRODUCTION Supercritical fluid technology (SFT) has received extensive attention during the past few decades for many industrial areas and high-tech fields such as food, pharmaceuticals, polymers, and so on.1−3 Supercritical fluid (SCF) has shown desirable properties of no surface tension, no residue, and quick diffusion, compared to other solvents. SCCO2 has been researched in detail because of its benign characteristics such as nontoxicity, environmentally acceptability, inexpensiveness, and especially its temperate operating conditions. The equilibrium solubility in high-pressure equilibrium is fundamental for the design of the SCF process, and there is a great deal of solubility data measured in SCCO2.4−8 However, so far as we know, there are no equilibrium solubility data of 4hydroxybenzaldehyde in SCCO2 with and without cosolvents reported so far. 4-Hydroxybenzaldehyde is an important intermediate in the pharmaceutical and spice industry, and it is also used for pesticides.9 There are two typical functional groups, hydroxyl and formaldehyde, in the 4-hydroxybenzaldehyde molecule, which should influence effectively the solubility of 4hydroxybenzaldehyde in SCCO2 with and without cosolvents. Moreover, it is necessary to investigate in detail the solubility of solid solute with its benzene ring coupling by different functional groups, such as hydroxyl (−OH), carboxyl (−COOH), aldehyde (−CHO), nitro (−NO2), ethoxycarbonyl (−C3H5O2), propyl ester groups (−C4H7O2), and so on. The obtained data can help to rationalize how the characteristic functional groups of solid solute affect its solubility in SCCO2. © 2014 American Chemical Society
In addition, the equilibrium solubility data of different solutes mentioned before are still demanded to satisfy the industrial requirements of SFT processes, such as extraction, catalysis, and separation in supercritical fluid, and reparation of drug particles using supercritical fluid pellets.10−13 In this work, the equilibrium solubility of 4-hydroxybenzaldehyde in SCCO2 was determined at temperatures of (308, 318, and 328) K and five pressure points from (11.0 to 21.0) MPa. The influence of different cosolvents (ethanol, ethyl acetate, and acetone) at a mole fraction of 0.04 was investigated at 318 K and the same experimental pressure. The equilibrium solubility data of 4-hydroxybenzaldehyde in SCCO2 was correlated with three semiempirical models respectively for the absence and presence of cosolvents. It is one branch of our research to make a thorough inquiry on the equilibrium solubility of benzene derivatives in SCCO2 by comparing the various functional groups and different positions on the benzene ring.
■
EXPERIMENTAL METHODS
Materials. 4-Hydroxybenzaldehyde is purchased from Aladdin Chemistry Co. Ltd. High-purity carbon dioxide and the carrier gas of nitrogen used for chromatography are supplied by Beijing Praxair Industrial Gas Co. Ltd. Ethanol, which is used for ultraviolet spectrophotometer analysis and the Received: December 12, 2013 Accepted: April 4, 2014 Published: April 16, 2014 1521
dx.doi.org/10.1021/je401082x | J. Chem. Eng. Data 2014, 59, 1521−1527
Journal of Chemical & Engineering Data
Article
Table 1. Physical Properties of Substances
a
puritya
compound
formula
CAS
4-hydroxybenzaldehyde carbon dioxide nitrogen ethanol ethyl acetate acetone
C7H6O2 CO2 N2 C2H6O C4H8O2 C3H6O
123-08-0 124-38-9 7727-37-9 64-17-5 141-78-6 67-64-1
> > > > > >
98.0 99.9 99.999 99.7 99.5 99.5
molecular weight/g·mol−1 122.12 44.00 28.01 46.07 88.11 58.08
The purity is based on mass fraction.
regression coefficient of more than 0.9999. Each equilibrium solubility data point was measured more than five times, and the result is their average. The uncertainty of equilibrium solubility measured in pure SCCO2 and SCCO2 with cosolvents was found to be 0.0108·10−5 and 0.0115·10−5. Correlation Models. To predict the solubility behavior, many models have been established to correlate the experimental solubility. Most of the models are based on a semiempirical relationship. Considering the presence of cosolvents in a ternary system (4-hydroxybenzaldehyde + cosolvents + SCCO2) which affects on the equilibrium solubility, some scholars indicated that the modified models have agreeable accuracy to correlate the experiment results. The models used in this work to correlate experiment results of 4hydroxybenzaldehyde in a binary system (4-hydroxybenzaldehyde + SCCO2) were Chrastil,18 M-S-T,19 and Bartle20 models, while those in the ternary system were calculated by the modified Chrastil,21 modified M-S-T,22 and Sovova23 models. The detailed descriptions of the above six models are shown in ref 7.
cosolvent, is purchased from Beijing Chemical Reagent Factory. The other cosolvents, ethyl acetate and acetone, are purchased from Beijing Chemical Reagent Factory. The physical properties of compounds used in this experiment are listed in Table 1.14 Apparatus and Procedure. The apparatus and procedure which was used to measure the solubility of 4-hydroxybenzaldehyde with and without cosolvents in SCCO2 have been given in our previous work.15−17 The description of the procedure is as follows. A pump (Nova, model 5542121) was used to compress CO2 which flowed from the CO2 cylinder into the surge flask. Then the pressurized CO2 which left from the surge flask passed through the pressure-regulating valve and entered into the preheating cell which was enwound by a heating coil. Alternatively, at the presence of cosolvents in the experiments, a pump (Beijing Weixing Factory, model LB-10C, accuracy ± 0.01 mL·min−1) was used to transport the cosolvents. The cosolvent passed through a cosolvent regulating valve and mixed sufficiently with pure CO2 in the preheating cell. The high-pressure equilibrium cell (volume 150 mL) which contained 8 g of 4-hydroxybenzaldehyde was injected with the forenamed mixed fluid. The aforesaid cell was immersed in a water bath (Chongqing Yinhe Experimental Instrument Corporation, model CS-530, accuracy ± 0.5 K). The operating conditions in the cell were gauged by a resistance thermometer (Beijing Chaoyang Automatic Instrument Factory, model XMT, uncertainty 0.1 K) for temperature and a pressure gauge (Heise, model CTUSA, uncertainty 0.05 MPa) for pressure. Through mass transfer, the system attained phase equilibrium after 30 min in the equilibrium cell. The SCCO2 streamed from the cell and decompressed to gaseous state. Lastly, the solute was separated out from CO2 and deposited in a two connected U-shape tube. A wet gas flow meter (Changchun Instrument Factory, model LML-2, accuracy ± 0.01 L) for gauging the flow rate of CO2 was employed. Analytical Method. In this work, after each termination of experimental sampling, the two connected U-shape tube which was used to collect the sample was washed by ethanol three times, and the washing solvent was shifted into the volumetric flask (50 mL) for standardization. The flask was immersed into ultrasonic cleaner (Kun Shan Ultrasonic Instruments Co., Ltd., model KQ-250DE) to make a sufficient solution; then an injection of 1 μL was taken from the flask into gas chromatography (Shimadzu, model GC-2014C) to be analyzed. A reversed phase mode was used to operate the analytical column (Shimadzu Shim-Pack CLC-ODS, 150 mm × 4.6 mm, 5 μm). The flow rate of nitrogen used for carrier gas was controlled with 1.2 mL·min−1. The operating condition of chromatography was 423 K for the column and 533 K for both sample injector and detector compartments. The calibration curve was measured by a group of standard samples with a
■
RESULTS AND DISCUSSION Solubility in SCCO2 of Binary Systems. The operating conditions, the solubility data (yb) of 4-hydroxybenzaldehyde in pure SCCO2, and the density (ρ) of SCCO2 in corresponding operating conditions are listed in Table 2. Each measured data point is shown as the mean (standard error of the mean (SEM)) for five replicated sample measurements. It can be seen from Table 2 that the solubility of 4-hydroxybenzaldehyde in pure SCCO2 is 0.73·10−5 to 13.77·10−5. Figure 1 describes that a crossover pressure region ranges from (12.0 to 14.0) MPa. The value of yb rises with pressure escalating when the temperature is unchanging. This phenomenon is explained that the density of solvent increases with the pressure increase. Therefore, an obvious improvement appears on the dissolving ability of solvent. In addition, the higher the pressure is, the stronger of the interaction between the solute molecular and solvent molecular will be. The effect of temperature is complicated. It mainly affects the vapor pressure of 4hydroxybenzaldehyde and density of SCCO2. As the temperature increases, the vapor pressure of 4-hydroxybenzaldehyde increases, while the density of SCCO2 decreases, and the former leads to the solubility increasing, while the latter has cross-current to the solubility. As shown in Figure 1, when the pressure is beyond (12.0 to 14.0) MPa, the major factor which affects the solubility is the vapor pressure of 4-hydroxybenzaldehyde, which rises with temperature increasing. Thus, the experimental solubility increases with temperature increasing. But, below (12.0 to 14.0) MPa, the main factor which influences solubility is the density of SCCO2. The density decreases with temperature increasing, which leads to the experimental solubility decreases with temperature increasing. 1522
dx.doi.org/10.1021/je401082x | J. Chem. Eng. Data 2014, 59, 1521−1527
Journal of Chemical & Engineering Data
Article
Table 3. Mole Fraction Solubility (yb′) of 4Hydroxybenzaldehyde in SCCO2 with Cosolvents at a Mole Fraction of 0.04 and Cosolvent Effect Factor ( f) at a Temperature of 318 K and Pressures from 11.0 MPa to 21.0 MPaa
Table 2. Mole Fraction Solubility (yb) of 4Hydroxybenzaldehyde in SCCO2 at Temperatures of 308 K, 318 K, and 328 K and Pressures from 11.0 MPa to 21.0 MPaa T/K
P/MPa
ρb/g·L−1
105·yb
308
11.0 13.0 15.0 18.0 21.0 11.0 13.0 15.0 18.0 21.0 11.0 13.0 15.0 18.0 21.0
743.95 785.70 815.06 848.04 873.67 603.15 693.65 741.97 789.24 822.91 414.90 571.33 653.50 723.08 767.88
2.01 2.58 3.25 4.38 5.20 1.72 3.24 4.72 6.52 8.85 0.73 3.77 6.98 10.56 13.77
318
328
cosolvent ethanol
ethyl acetate
acetone
a Standard uncertainties u are the following: u(T) = 0.1 K; u(P) = 0.05 MPa; u(yb) = 0.0108·10−5. bρ is the density of pure CO2, which is obtained from the National Institute of Standards and Technology (NIST) fluid property database.
P/MPa
105·yb′
f
11.0 13.0 15.0 18.0 21.0 average value 11.0 13.0 15.0 18.0 21.0 average value 11.0 13.0 15.0 18.0 21.0 average value
1.90 4.32 5.88 8.47 11.27
0.95 1.67 1.81 1.93 2.17 1.71 1.61 1.76 1.93 2.33 2.44 2.01 4.82 2.40 1.89 1.86 2.02 2.60
2.77 5.69 9.11 15.18 21.60 3.52 9.03 13.20 19.59 27.78
a Standard uncertainties u are the following: u(T) = 0.1 K; u(P) = 0.05 MPa; u(yb′) = 0.0115·10−5.
Figure 1. Experimental solubility (yb) of 4-hydroxybenzaldehyde in SCCO2 as a function of pressure: ▲, 308 K; ●, 318 K; ■, 328 K.
Figure 2. Experimental solubility (yb′) of 4-hydroxybenzaldehyde in SCCO2 with cosolvents (▲, ethanol; ●, ethyl acetate; ■, acetone) in a mole fraction of 0.04 as a function of pressure.
Solubility in SCCO2 of the Ternary System. In this work, three cosolvents (ethanol, ethyl acetate, and acetone) are chosen at a mole fraction of 0.04. The operating conditions, which are 318 K and pressures of (11.0 to 21.0) MPa, and the equilibrium solubility of 4-hydroxybenzaldehyde (yb′) are listed in Table 3. The limit of yb′ is from 1.90·10−5 to 27.78·10−5. To reveal the function of cosolvents in the ternary system more obviously, a definition named cosolvent effect factor (f) is added as the following eq 1:
f=
3, all three cosolvents (ethanol, ethyl acetate, acetone) enhance the solubility of solute; the average value is 1.71 for ethanol, 2.01 for ethyl acetate, and 2.60 for acetone, respectively. The cosolvent effect follows the order of ethanol < ethyl acetate < acetone. Some researchers explained this phenomenon. Foster and Ting24,25 pointed out that the existence of cosolvent improved the density of solvent and, thus, enhanced the dissolving ability of solvent, while other scholars believed the polarity and hydrogen bond were major factors to affect the solubility. In addition, the dipole moment which described the strength of polarity for the cosolvents are ethanol (5.70·10−30 C·m), ethyl acetate (5.94·10−30 C·m), and acetone (9.50·10−30 C·m). Thus, the polarity of the cosolvents follows the order of ethanol < ethyl acetate < acetone.26 Compared to CO2
yb ′ yb
(1)
Figure 2 illustrates that the solubility of 4-hydroxybenzaldehyde in SCCO2 has a great improvement in the presence of each cosolvent. On the basis of the average values of f in Table 1523
dx.doi.org/10.1021/je401082x | J. Chem. Eng. Data 2014, 59, 1521−1527
Journal of Chemical & Engineering Data
Article
Table 4. Comparison Solubility of Solutes with Six Kinds of Functional Groups
explained that the nitro (−NO2) group on the benzene ring of the solutes is one of the electrophilic groups which may enhance solute solubility in pure SCCO2.32 The melting point of 4-hydroxybenzaldehyde is analogous to that of ethyl 4hydroxybenzoate and has a similar solubility in SCCO2. From Table 4, the melting point of solute could be an important factor on solubility of solid solute in SCCO2, which should be studied in detail with a great deal of solubility data. The objective of this study may help researchers develop models for a better description of the phase equilibrium of the supercritical system. Correlation Results. In this work, the equilibrium solubility data in pure SCCO2 have been correlated by Chrastil, MéndezSantiago and Teja, and Bartle models. The correlation parameters are presented in Table 5. The result of the correlation defines the average absolute relative deviation (AARD) as the following:
molecules, the dissolving ability of the modified solvent improved, which led to the highest solubility enhancement of the polar solute. Effects of Functional Groups on Equilibrium Solubility in SCCO2. The equilibrium solubility in SCCO2 of six kinds of functional groups on the opposite location of hydroxyl (−OH) on the benzene ring of different solutes are listed in Table 4 at the similar range of temperature and pressure. Comparing the solubility of ethyl 4-hydroxybenzoate27 and propyl 4-hydroxybenzoate28 (with a homologous ester functional group (−C3H5O2 and −C4H7O2) on the opposite location of hydroxyl (−OH) on the benzene ring of solutes) in Table 4, the latter has a lower melting point but higher solubility than that of the former. The molecular cohesion capability is usually decided by its intrinsic valence bonds and may be represented by its melting point. A higher melting point indicates that there is a stronger self-aggregation force among solute molecules, suggesting that it is difficult for solvent molecular to dissociate solute molecular from its ensemble. This may explain the trend observed for ethyl 4-hydroxybenzoate and propyl 4-hydroxybenzoate in Table 4. Moreover, the solid solute of hydroquinone29 and 4-hydroxybenzoic acid,30 which can form intermolecular hydrogen bonds due to the presence of hydroxyl (−OH) and carboxyl (−COOH), has a much higher melting point and much lower solubility than other five solutes which are listed in Table 4. However, ethyl 4-hydroxybenzoate and 4nitrophenol31 have a similar melting point but show a significant difference in solubility. This phenomenon could be
AARD(%) =
100 n
n
∑ 1
|ycal − yexp | yexp
(2)
where ycal is the calculated value, yexp is the experimental data, and n is the total number of data points. In the binary system, 15 points of experimental data are correlated with the AARDs fewer than 8.50 %, which shows better results. The Chrastil model has the best correlation with the AARD of 6.82 %. To compare the correlated results with those published in the literature, Figure 3 also includes the 1524
dx.doi.org/10.1021/je401082x | J. Chem. Eng. Data 2014, 59, 1521−1527
Journal of Chemical & Engineering Data
Article
by the M-S-T model were obtained for the solutes with a similar molecular structure. The correlation parameters of 4-hydroxybenzaldehyde in SCCO2 with each cosolvents for five solubility points are calculated with the modified Chrastil, the modified M-S-T, and Sovova models, which are listed in Table 5. All of the calculated results of AARD are fewer than 8.87 %. The result of the GChrastil model with the cosolvent of ethanol obtained the best agreement compared with others. Enthalpy of Sublimation Calculation. The thermodynamic enthalpy values of some solid solutes, including total enthalpy, sublimation enthalpy, and solvation enthalpy, could be calculated by some researchers. They took advantage of the parameters in Chrastil and Bartle models.7,18,20 The constant a2 in the Chrastil model is related to the total enthalpy (H1) changing as eq 3, where R is the gas constant, H1 is equal to the sum of the enthalpy of vaporization H2, which is obtained by eq 4 through the parameter a2 of Bartle model, and the enthalpy of solvation (H3). According to eqs 3 to 5, the enthalpy of each binary system can be approximated.
Table 5. Correlation Parameters for the Solubility of 4Hydroxybenzaldehyde in SCCO2 for the Binary and Ternary Systems and AARD (%) of Different Modelsa compounds without cosolvents
models Chrastil M-S-T Bartle
ethanol
G-Chrastil S-M-S-T
ethyl acetate
Sovova G-Chrastil S-M-S-T
acetone
Sovova G-Chrastil S-M-S-T Sovova
correlation parameters a0 = −12.96;a1 = −8.991·103; a2 = 5.90 a0 = −1.440·104; a1 = 3.35; a2 = 30.28 a0 = −1.179·104; a1 = 0.01; a2 = 31.77 a0 = −45.79; a1 = 6.62; a2 = 0; a3 = 0 a0 = −4.052·103; a1 = 3.46; a2 = 0; a3 = 0 a0 = 3.36; a1 = 0; a2 = 1.47 a0 = −51.76; a1 = 7.59; a2 = 0; a3 = 0 a0 = −4.236·103; a1 = 3.91; a2 = 0; a3 = 0 a0 = 5.52; a1 = 0; a2 = 1.55 a0 = −50.99; a1 = 7.52; a2 = 0; a3 = 0 a0 = −4.102·103; a1 = 3.87; a2 = 0; a3 = 0 a0 = 4.68; a1 = 0; a2 = 1.41
AARD (%) 6.82 7.76 8.50 2.98 3.15 3.98 8.31 8.87 3.05 3.19
H1 = Ra 2
3.28
(3)
(a2 of Chrastil model, listed in Table 5)
4.43
H2 = −Ra 2
a
For Chrastil, M-S-T, Bartle, G-Chrastil, S-M-S-T models: a0 is the constant of each model; a1, a2, and a3 are the parameters of ρ, T, and y3, respectively. For the Sovova model: a0 is the constant; a1 and a2 are the parameters of y3 and y1, respectively.
(4)
(a2 of Bartle model, listed in Table 5) H3 = H1 − H2
(5)
Jin et al.33,34 calculated the aforementioned enthalpy of otolidine and bisphenol A and compared the enthalpy values between two solutes. Tabernero et al.35 used the semiempirical models to determine the enthalpy of some solid solutes in SCFs and listed enthalpies of different pharmaceuticals. Hojjati et al.36 and Fuente et al.37 made use of the above-mentioned method to calculate the thermodynamic enthalpy. The total enthalpy (H1) of 4-hydroxybenzaldehyde is −82.36 kJ·mol−1 obtained by the parameter a2 of the Chrastil model, while the sublimation enthalpy (H2) is 106.42 kJ·mol−1 calculated by the parameter a2 of the Bartle model. The solvation enthalpy (H3) could be obtained by the subtraction of total enthalpy to sublimation enthalpy, which is −188.78 kJ· mol−1.
■
CONCLUSIONS The mole fraction of 4-hydroxybenzaldehyde in SCCO2 is measured at temperatures of (308, 318, and 328) K and the pressure range from (11.0 to 21.0) MPa with a range from (0.73·10−5 to 13.77·10−5). A crossover pressure region of 4hydroxybenzaldehyde in pure SCCO2 is between (12.0 and 14.0) MPa. The solubility of different solutes with six kinds of functional groups on the opposite location of hydroxyl on the benzene ring is compared and analyzed. The solubility data in SCCO2 are correlated by three widely used models, and the AARD is 6.82 % for Chrastil, 7.76 % for M-S-T, and 8.50 % for Bartle models. The thermodynamic property is −82.36 kJ· mol−1 for the total enthalpy, 106.42 kJ·mol−1 for the sublimation enthalpy, and −188.78 kJ·mol−1 for the solvation enthalpy. The cosolvents with a mole fraction of 0.04 significantly improve the solubility of 4-hydroxybenzaldehyde in SCCO2. The average cosolvent effect factor is 1.71 for ethanol, 2.01 for ethyl acetate, and 2.60 for acetone. The equilibrium solubility in SCCO2 with the presence of cosolvents is correlated by the modified Chrastil, modified
Figure 3. Comparison of experimental solubility of different solutes in pure SCCO2 and calculated results by the M-S-T model at (308, 318, and 328) K. Each error bar is the deviation of experimental solubility from the M-S-T model. ●, 4-hydroxybenzaldehyde; ■, 4-hydroxybenzoic acid; ▼, 4-nitrophenol; ▲, ethyl 4-hydroxybenzoate.
other three deviation plots, such as 4-hydroxybenzoic acid, 4nitrophenol, and ethyl 4-hydroxybenzoate, which has a different functional group on the opposite location of hydroxyl (−OH) on the benzene ring of different solutes (listed in Table 4) at a similar range of temperature and pressure. To clearly compare the differences between our results with those already reported, the error values of each experimental point have been expanded 5 times higher than the real one. The AARD value by is 7.76 % for 4-hydroxybenzaldehyde, 8.25 % for 4-hydroxybenzoic acid, 7.43 % for 4-nitrophenol, and 14.17 % for ethyl 4hydroxybenzoate, which indicates the similar correlated results 1525
dx.doi.org/10.1021/je401082x | J. Chem. Eng. Data 2014, 59, 1521−1527
Journal of Chemical & Engineering Data
Article
(16) Tang, Z.; Jin, J. S.; Zhang, Z. T.; Yu, X. Y.; Xu, J. N. Solubility of 3,5-dinitrobenzoic acid in supercritical carbon dioxide with cosolvent at temperatures from (308 to 328) K and pressures from (10.0 to 21.0) MPa. J. Chem. Eng. Data 2010, 55, 3834−3841. (17) Jin, J. S.; Dou, Z. M.; Liu, H. T.; Wu, H.; Zhang, Z. T. Solubility of o-nitrobenzoic acid in modified supercritical carbon dioxide at (308 to 328) K. J. Chem. Eng. Data 2012, 57, 2217−2220. (18) Chrastil, J. Solubility of solids and liquids in supercritical gases. J. Phys. Chem. 1982, 86, 3016−3021. (19) Méndez-Santiago, J.; Teja, A. S. The solubility of solids in supercritical fluids. Fluid Phase Equilib. 1999, 158−160, 501−510. (20) Bartle, K. D.; Clifford, A. A.; Jafar, S. A.; Shilstone, G. F. Solubilities of solids and liquids of low volatility in supercritical carbon dioxide. J. Phys. Chem. 1991, 20, 713−756. (21) González, J. C.; Vieytes, M. R.; Botana, A. M.; Vieites, J. M.; Botana, L. M. Modified mass action law-based model to correlate the solubility of solids and liquids in entrained supercritical carbon dioxide. J. Chromatogr., A 2001, 910, 119−125. (22) Sauceau, M.; Letourneau, J. J.; Richon, D.; Fages, J. Enhanced density-based models for solid compound solubilities in supercritical carbon dioxide with cosolvents. Fluid Phase Equilib. 2003, 208, 99− 113. (23) Sovova, H. Solubility of ferulic acid in supercritical carbon dioxide with ethanol as cosolvent. J. Chem. Eng. Data 2001, 46, 1255− 1257. (24) Foster, N. R.; Singh, H.; Yun, S. L. J.; Tomasko, D. L.; Macnaughton, S. J. Polar and nonpolar cosolvent effects on the solubility of cholesterol in supercritical fluids. Ind. Eng. Chem. Res. 1993, 32, 2849−2853. (25) Ting, S. S. T.; Macnaughton, S. J.; Tomasko, D. L.; Foster, N. R. Solubility of naproxen in supercritical carbon dioxide with and without cosolvents. Ind. Eng. Chem. Res. 1993, 32, 1471−1481. (26) Sengwa, R. J.; Sankhla, S.; Shinyashik, N. Dielectric parameters and hydrogen bond interaction: study of binary alcohol mixtures. J. Solution Chem. 2008, 37, 137−153. (27) Li, W. M.; Jin, J. S.; Tian, G. H.; Zhang, Z. T. Single-component and mixture solubilities of ethyl p-hydroxybenzoate and ethyl paminobenzoate in supercritical CO2. Fluid Phase Equilib. 2008, 264, 93−98. (28) Cheng, K. W.; Tang, M.; Chen, Y. P. Solubilities of benzoin, propyl 4-hydroxybenzoate and mandelic acid in supercritical carbon dioxide. Fluid Phase Equilib. 2002, 201, 79−96. (29) Garc̀a-González, J.; Molina, M. J.; Rodrìguez, F.; Mirada, F. Solubilities of hydroquinone and p-quinone in supercritical carbon dioxide. Fluid Phase Equilib. 2002, 200, 31−39. (30) Lucien, F. P.; Foster, N. R. Influence of matrix composition on the solubility of hydroxybenzoic acid isomers in supercritical carbon dioxide. Ind. Eng. Chem. Res. 1996, 35, 4686−4699. (31) Shamsipur, M.; Fat’hi, M. R.; Yamini, Y.; Ghiasvand, A. R. Solubility determination of nitrophenol derivatives in supercritical carbon dioxide. J. Supercrit. Fluids 2002, 23, 225−231. (32) Zhao, F. Y.; Fujita, S.; Sun, J. M.; Ikushima, Y.; Arai, M. Hydrogenation of nitro compounds with supported platinum catalyst in supercritical carbon dioxide. Catal. Today 2004, 98, 523−528. (33) Jin, J. S.; Dou, Z. M.; Su, G. X.; Zhang, Z. T.; Liu, H. T. Solubility of o-tolidine in pure and modified supercritical carbon dioxide. Fluid Phase Equilib. 2012, 315, 9−15. (34) Jin, J. S.; Wang, Y. B.; Liu, H. T.; Zhang, Z. T. Determination and calculation of solubility of bisphenol A in supercritical carbon dioxide. Chem. Eng. Res. Des. 2013, 91, 158−164. (35) Tabernero, A.; Martín del Valle, E. M.; Galán, M. A. On the use of semiempirical models of (solid + supercritical fluid) systems to determine solid sublimation properties. J. Chem. Thermodyn. 2011, 43, 711−718. (36) Hojjati, M.; Vatanara, A.; Yamini, Y.; Moradi, M.; Najafabadi, A. R. Supercritical CO2 and highly selective aromatase inhibitors: Experimental solubility and empirical data correlation. J. Supercrit. Fluids 2009, 50, 203−209.
M-S-T, and Sovova models, and the results of the AARD are less than 8.87 %.
■
AUTHOR INFORMATION
Corresponding Authors
*Tel.: +86-10-64434788. Fax: +86-10-64436781. E-mail:
[email protected] (H.W.). *E-mail:
[email protected] (J.-s.J.). Funding
This research was financially supported by National Natural Science Foundation of China (No. 21176012), Natural Science Foundation of Jiangsu Province (No. BK2012595) and Petrochina Limited Company (No. 2012A-2012-01). The authors are grateful to the support of this research from the Mass Transfer and Separation Laboratory in Beijing University of Chemical Technology. Notes
The authors declare no competing financial interest.
■
REFERENCES
(1) Rozzi, N. L.; Singh, R. K. Supercritical fluids and the food industry. Compr. Rev. Food Sci. Food Saf. 2002, 1, 33−44. (2) Zordi, N. D.; Kikic, I.; Moneghini, M.; Solinas, D. Solubility of pharmaceutical compounds in supercritical carbon dioxide. J. Supercrit. Fluids 2012, 66, 16−22. (3) Yoon, S. D.; Byun, H. S. Molecularly imprinted polymers for selective separation of acetaminophen and aspirin by using supercritical fluid technology. J. Chem. Eng. Data 2013, 226, 171−180. (4) Lucien, F. P.; Foster, N. R. Solubilities of solid mixtures in supercritical carbon dioxide: a review. J. Supercrit. Fluids 2000, 17, 111−134. (5) Guptar, R. B.; Shim, J. J. Solubility in supercritical carbon dioxide; CRC Press: Boca Raton, FL, 2007. (6) Fonseca, J. M. S.; Dohrn, R.; Peper, S. High-pressure fluid-phase equilibria: experimental methods and systems investigated (2005− 2008). Fluid Phase Equilib. 2011, 300, 1−69. (7) Škerget, M.; Knez, Ž .; Knez-Hrnčič, M. Solubility of solids in suband supercritical fluids: a review. J. Chem. Eng. Data 2011, 56, 694− 719. (8) Teoh, W. H.; Mammucari, R.; Foster, N. R. Solubility of organometallic complexes in supercritical carbon dioxide: a review. J. Organomet. Chem. 2013, 724, 102−116. (9) Ruiz, C. C.; Bayona, A. H.; Sanchez, F. G. Derivative spectrophotometric determination of vanillin and p-hydroxy benzaldehyde in vanilla bean extracts. J. Agric. Food Chem. 1990, 38, 178−181. (10) Sónia, A. O. S.; Juan, J. V.; Carlos, M. S.; Carlos, P. N.; Armando, J. D. S. Supercritical fl A. extraction of phenolic compounds from Eucalyptus globules Labill bark. J. Supercrit. Fluids 2012, 71, 71− 79. (11) Wang, Y. Z.; Wang, S. Z.; Guo, Y.; Xu, D. H.; Gong, Y. M.; Tang, X. Y.; Ma, H. H. Oxidative degradation of lurgi coal-gasification wastewater with Mn2O3, Co2O3, and CuO catalysts in supercritical water. Ind. Eng. Chem. Res. 2012, 51, 16573−16579. (12) Cristancho, C. A. M.; Peper, S.; Johannsen, M. Supercritical fluid simulated moving bed chromatography for the separation of ethyl linoleate and ethyl oleate. J. Supercrit. Fluids 2012, 66, 129−136. (13) Wang, L. H.; Che, X.; Xu, H.; Zhou, L. L.; Han, J.; Zou, M. J.; Liu, J.; Liu, Y.; Liu, J. W.; Zhang, W.; Cheng, G. A novel strategy to design sustained-release poorly water-soluble drug mesoporous silica microparticles based on supercritical fluid technique. Int. J. Pharm. 2013, 454, 135−142. (14) Available online: http://www.chemblink.com/products/123-080.htm (last accessed on July 11, 2013). (15) Li, J. L.; Jin, J. S.; Zhang, Z. T.; Wang, Y. B. Measurement and correlation of solubility of benzamide in supercritical carbon dioxide with and without cosolvent. Fluid Phase Equilib. 2011, 307, 11−15. 1526
dx.doi.org/10.1021/je401082x | J. Chem. Eng. Data 2014, 59, 1521−1527
Journal of Chemical & Engineering Data
Article
(37) Fuente, J. C.; Oyarzun, B.; Quezada, N.; Valle, J. M. Solubility of carotenoid pigments (lycopene and astaxanthin) in supercritical carbon dioxide. Fluid Phase Equilib. 2006, 247, 90−95.
1527
dx.doi.org/10.1021/je401082x | J. Chem. Eng. Data 2014, 59, 1521−1527
