STUDY OF SOLUBILITY IN SUPERCRITICAL FLUIDS: THERMODYNAMIC CONCEPTS AND MEASUREMENT METHODS - A REVIEW

Rad, Hadi Behjati; Sabet, Javad Karimi; Varaminian, Farshad

doi:10.1590/0104-6632.20190364s20170493

Hadi Behjati Rad

Semnan University, Faculty of Chemical, Petroleum and Gas Engineering, Semnan, Iran. E-mail: fvaraminian@semnan.ac.ir

Javad Karimi Sabet

Nuclear Science and Technology Research Institute, Material and Nuclear Fuel Research School, Tehran, Iran. E-mail: j_karimi@alum.sharif.edu

http://orcid.org/0000-0001-9937-7171

Farshad Varaminian

Semnan University, Faculty of Chemical, Petroleum and Gas Engineering, Semnan, Iran. E-mail: fvaraminian@semnan.ac.ir

http://orcid.org/0000-0002-5188-3611

* Corresponding author: Javad Karimi Sabet and Farshad Varaminian - E-mail: j_karimi@alum.sharif.edu; fvaraminian@semnan.ac.ir

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Figure 1
Phase behavior classification of binary mixtures obtained from the van der Waals equation of state. Points C₁ and C₂ are the critical points of components 1 and 2, respectively. UCST and LLV imply the upper critical solution temperature and three-phase equilibrium between two liquid phases and one vapor phase, respectively. Solid lines represent pure component vapor pressure curves, dashed curves are the critical mixture curve for a binary mixture, and open triangles are the critical endpoints (McHugh and Krukonis, 2013McHugh, M., Krukonis, V. Supercritical fluid extraction: principles and practice, Elsevier (2013).).

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Figure 2
Phase diagram for an asymmetric binary system consisting of a solid (second component) in the presence of supercritical carbon dioxide (first component) (Lucien and Foster, 2000Lucien, F. P., Foster, N. R. Solubilities of solid mixtures in supercritical carbon dioxide: a review. The Journal of Supercritical Fluids , 17, 111-134 (2000). https://doi.org/10.1016/S0896-8446(99)00048-0
https://doi.org/10.1016/S0896-8446(99)00... ).

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Figure 3
P-x projection of the phase diagram at a temperature which intersects the SLV line (Lucien and Foster, 2000Lucien, F. P., Foster, N. R. Solubilities of solid mixtures in supercritical carbon dioxide: a review. The Journal of Supercritical Fluids , 17, 111-134 (2000). https://doi.org/10.1016/S0896-8446(99)00048-0
https://doi.org/10.1016/S0896-8446(99)00... ).

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Figure 4
Gibbs phase triangle for a ternary system, the composition of the mixture is x_A=0.2, x_B=0.3 and x_C=0.5 (Deiters and Kraska, 2012Deiters, U. K., Kraska, T. High-Pressure Fluid Phase Equilibria: Phenomenology and Computation, Elsevier, (2012).).

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Figure 5
The schematic of an apparatus for determining fluid phase equilibrium using the analytic-recirculation method, (1) sample space, (2) pressure vessel, (3) heater, (4) manometer, (5) thermometer, (6) recirculation pumps, and (7) valves (Deiters and Kraska, 2012Deiters, U. K., Kraska, T. High-Pressure Fluid Phase Equilibria: Phenomenology and Computation, Elsevier, (2012).).

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Figure 6
The Schematic of an apparatus for determining fluid phase equilibrium using the synthetic method, (1) sample space, (2) pressure vessel, (3) heater, (4) piston, (5) stirrer, (6) manometer, (7) thermometer, and (8) valves (Deiters and Kraska, 2012Deiters, U. K., Kraska, T. High-Pressure Fluid Phase Equilibria: Phenomenology and Computation, Elsevier, (2012).).

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Figure 7
The schematic of an apparatus for determining fluid phase equilibrium using the flow of matter method, (1) compressor, (2) pressure vessel, (3) cold collector attached to precision scale, and (4) flow meter (Deiters and Kraska, 2012Deiters, U. K., Kraska, T. High-Pressure Fluid Phase Equilibria: Phenomenology and Computation, Elsevier, (2012).).

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Table 1
Comparison of semiempirical models for determining solubility in various systems.

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Table 2
Comparison of simulated and experimental solubility of acetaminophen and ibuprofen in supercritical CO₂ (Noroozi et al., 2016Noroozi, J., Karimi-Sabet, J., Ghotbi, C., Robert, M. A. Solvation Free Energy and Solubility of acetaminophen and ibuprofen in Supercritical Carbon Dioxide: Impact of the Solvent Model. The Journal of Supercritical Fluids , 109, 166-176 (2016). https://doi.org/10.1016/j.supflu.2015.11.009
https://doi.org/10.1016/j.supflu.2015.11... ).

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Model	Exampel of solute	Temperature (K)	Pressure (bar)	AARD%	Ref
Chrastil	Norfloxacin	308.2-328.2	100-303	33.90	(Chim et al., 2012)
	Ofloxacin	308.2-328.2	100-303	22.10	(Chim et al., 2012)
	Cefixime trihydrate	308-328	183-335	2.57	(Khamda et al., 2013)
	Oxymetholone	308-328	121-305	5.95	(Khamda et al., 2013)
	Artemisinin	313-333	110-310	8.32	(Gong and Cao, 2009)
	1-amino-4-hydroxyanthraquinone	323.15-383.15	125-250	15.00	(Tamura and Alwi, 2015)
	1-hydroxy-4-nitroanthraquinone	323.15-383.15	125-250	10.60	(Tamura and Alwi, 2015)
	Thymol	308-323	78-250	17.82	(Milovanovic et al., 2013)
	grape seed oil	313-343	200-500	0.80	(Duba and Fiori, 2016)
	bisphenol A	308-328	110-210	8.25	(Jin et al., 2013)
	N,N-dimethylformamide diethyl acetal	313-353	78-133	6.10	(Zhang et al., 2014)
	o-nitrobenzoic acid	308-328	100-210	5.91	(Tang et al., 2012)
Sung and Shim	1-amino-4-hydroxyanthraquinone	323.15-383.15	125-250	7.60	(Tamura and Alwi, 2015)
	1-hydroxy-4-nitroanthraquinone	323.15-383.15	125-250	5.10	(Tamura and Alwi, 2015)
	bisphenol A	308-328	110-210	3.39	(Jin et al., 2013)
	N,N-dimethylformamide diethyl acetal	313-353	78-133	4.63	(Zhang et al., 2014)
	o-nitrobenzoic acid	308-328	100-210	4.30	(Tang et al., 2012)
Adachi and Lu	Thymol	308-326	78-250	16.45	(Milovanovic et al., 2013)
	grape seed oil	313-343	200-500	0.26	(Duba and Fiori, 2016)
	bisphenol A	308-328	110-210	5.45	(Jin et al., 2013)
Sparks et al.	Norfloxacin	308.2-328.2	100-303	26.90	(Chim et al., 2012)
	Ofloxacin	308.2-328.2	100-303	8.60	(Chim et al., 2012)
	grape seed oil	313-343	200-500	0.26	(Duba and Fiori, 2016)
Bartle et al.	Norfloxacin	308.2-328.2	100-303	37.30	(Chim et al., 2012)
	Ofloxacin	308.2-328.2	100-303	23.10	(Chim et al., 2012)
	Cefixime trihydrate	308-328	183-335	3.73	(Khamda et al., 2013)
	Oxymetholone	308-328	121-305	5.86	(Khamda et al., 2013)
	grape seed oil	313-343	200-500	1.46	(Duba and Fiori, 2016)
	bisphenol A	308-328	110-210	8.67	(Jin et al., 2013)
Gordillo et al.	1-chloro-2,4-dinitrobenzene	308-313	95-145	1.27	(Reddy and Madras, 2011)
Gordillo et al.	m-dinitrobenzene	308-328	95-145	8.52	(Reddy and Madras, 2011)
Mendez-Santiago-Teja	Norfloxacin	308.2-328.2	100-303	38.10	(Chim et al., 2012)
	Ofloxacin	308.2-328.2	100-303	23.20	(Chim et al., 2012)
	Cefixime trihydrate	308-328	183-335	3.56	(Khamda et al., 2013)
	Oxymetholone	308-328	121-305	6.27	(Khamda et al., 2013)
	1-amino-4-hydroxyanthraquinone	323.15-383.15	125-250	1.40	(Tamura and Alwi, 2015)
	1-hydroxy-4-nitroanthraquinone	323.15-383.15	125-250	11.50	(Tamura and Alwi, 2015)
	Spironolactone	308-338	160-400	13.10	(Hezave et al., 2013)
	Artemisinin	313-333	110-310	8.33	(Gong and Cao, 2009)
	grape seed oil	313-343	200-500	1.46	(Duba and Fiori, 2016)
	bisphenol A	308-328	110-210	6.74	(Jin et al., 2013)
	1-chloro-2,4-dinitrobenzene	308-313	95-145	7.25	(Reddy and Madras, 2011)
	m-dinitrobenzene	308-328	95-145	11.50	(Reddy and Madras, 2011)
	o-nitrobenzoic acid	308-328	100-210	4.68	(Tang et al., 2012)
Kumar and Johnston	Cefixime trihydrate	308-328	183-335	2.49	(Khamda et al., 2013)
	Oxymetholone	308-328	121-305	9.20	(Khamda et al., 2013)
	1-amino-4-hydroxyanthraquinone	323.15-383.15	125-250	10.60	(Tamura and Alwi, 2015)
	1-hydroxy-4-nitroanthraquinone	323.15-383.15	125-250	6.80	(Tamura and Alwi, 2015)
	grape seed oil	313-343	200-500	0.26	(Duba and Fiori, 2016)
	bisphenol A	308-328	110-210	6.71	(Jin et al., 2013)
	Spironolactone	308-338	160-400	12.20	(Hezave et al., 2013)
	o-nitrobenzoic acid	308-328	100-210	6.61	(Tang et al., 2012)
Dell Valle and Aguilera	Thymol	308-323	78-250	16.27	(Milovanovic et al., 2013)
Dell Valle and Aguilera	grape seed oil	313-343	200-500	0.79	(Duba and Fiori, 2016)
Yu et al.	grape seed oil	313-343	200-500	0.56	(Duba and Fiori, 2016)
Yu et al.	bisphenol A	308-328	110-210	3.01	(Jin et al., 2013)
Jouyban-Chan-Foster	N,N-dimethylformamide diethyl acetal	313-353	78-133	4.56	(Zhang et al., 2014)
Jouyban-Chan-Foster	o-nitrobenzoic acid	308-328	100-210	6.03	(Tang et al., 2012)

Solute	Density (Kmol/m³)	TraPPE	-EPM2	Zhang	Exp
	Mole fraction × 10⁶
Acetaminophen (T=313 K)	14.30	0.53	0.29	0.16	0.37
	16.61	1.24	0.61	0.36	0.65
	18.50	2.44	1.14	0.66	1.08
	19.98	3.80	1.82	1.08	1.78
	Mole fraction × 10³
Ibuprofen (T=308 K)	16.24	1.40	1.08	0.66	1.35
	17.46	2.07	1.59	1.04	2.13
	18.81	3.15	2.13	1.39	3.23
	20.03	3.33	2.48	1.68	4.41

\ln y_{2} = \frac{Δ H_{2}^{f}}{R} (\frac{1}{T_{2, m}} - \frac{1}{T}) - (\frac{v_{2}}{RT}) {(δ_{1} - δ_{2})}^{2} - 1 + (\frac{v_{2}}{v_{1}}) - \ln (\frac{v_{2}}{v_{1}})

[1] * Corresponding author: Javad Karimi Sabet and Farshad Varaminian - E-mail: j_karimi@alum.sharif.edu; fvaraminian@semnan.ac.ir

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STUDY OF SOLUBILITY IN SUPERCRITICAL FLUIDS: THERMODYNAMIC CONCEPTS AND MEASUREMENT METHODS - A REVIEW

Abstract