Solubility of Phenylphosphinic Acid in Supercritical Carbon Dioxide and the Influence of Methanol on the Solubility Behavior

Abstract

The solubility of phenylphosphinic acid (PPA) was measured for the first time in supercritical carbon dioxide (SCCO2) at 313, 323, and 333 K with pressure ranging from 10–20 MPa using a dynamic flow technique. The solubility of PPA in neat SCCO2 ranged from 0.1 × 10–5 to 18 × 10–5 mol/mol. The influence of cosolvent, methanol, on solubility behavior was studied by measuring the solubility of PPA in SCCO2 + methanol medium (1 and 4 mol % methanol) at 313 and 323 K with pressure varying from 10–20 MPa. The highest solubility of PPA in the SCCO2 + methanol mixture is 29.4 × 10–4 mol/mol at 313 K and 20 MPa with a methanol composition of 4 mol %. The solubilities in neat SCCO2 were correlated using different semiempirical equations (Mendez–Teja, Chrastil, and Bartle) with an average deviation of <10%. The solubility in the presence of methanol was correlated with four semiempirical/empirical models (modified Chrastil, modified Mendez–Teja, Garlapati model, and Jouyban equation); among these models, Jouyban model resulted in better correlation with an average deviation of 5%.

Experimental Measurement and Thermodynamic Modeling of Capecitabine (an Anticancer Drug) Solubility in Supercritical Carbon Dioxide in a Ternary System: Effect of Different Cosolvents

“…It was proved that the polar solute solubility in sc-CO 2 is significantly enhanced by adding a small amount of a polar cosolvent. Remarkable effect of the addition of a little amount (less than 10%) of various kinds of polar solvents such as methanol, , ethanol, , acetone, dimethyl sulfoxide (DMSO), and menthol , on solute solubility increment in sc-CO 2 has been extensively reported, previously.…”

Improving and measuring the solubility of favipiravir and montelukast in SC-CO2 with ethanol projecting their nanonization

“…Several studies have demonstrated that a strategy for improving these values is by incorporating a polar or non-polar cosolvent that can increase the solvating potential of SC-CO 2 perhaps lowering the operating pressure. 15–41 A selection of some relevant studies on improving the solubility of solutes in ternary systems (SC-CO 2 + cosolvent + solute) are included in Table 1. In a recent study, Sodeifian et al found that employing menthol as a cosolvent increased the solubility of ketoconazole in SC-CO 2 at 308–338 K and 12–30 MPa from a range value between 2.00 × 10 −7 and 8.02 × 10 −5 to the drug solubility values of 1.20 × 10 −5 to 1.96 × 10 −4 .…”

“…In the current work, ethanol was used for the rst time as a cosolvent approved for pharmaceutical applications with the aim of improving the solubility of favipiravir and montelukast in SC-CO 2 and promoting further research dealing with their nanonization through techniques using SC-CO 2 as a solvent, such as rapid expansion of supercritical uid solutions (RESS). In this study ethanol was used at concentrations of 1 and 3 mol% when measuring the solubilities of favipiravir and montelukast in SC-CO 2 at various pressures and temperatures (308-338 K) (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30). Additionally, six density-based semiempirical models, namely; MST, 50 Sodeian-Sajadian, 51 González et al, 52 Soltani-Mazloumi, 53 Garlapati-Madras, 54 and Jouyban et al, 55 with four to seven adjustable parameters were used to correlate the solubilities of favipiravir and montelukast in both studied ternary systems.…”

Solubility of sinensetin and isosinensetin from Cat’s Whiskers (Orthosiphon stamineus) leaves in ethanol-assisted supercritical carbon dioxide extraction: experimental and modeling

“…There are several methods for measuring solubility in SC-CO 2 . The most substantially applied by researchers to calculate the solubility of SC-CO 2 systems is using a dynamic approach (John et al 2019;Ongkasin et al 2019;Zhu et al 2016). This method is proved effective since a high number of fractionation data can be obtained in a short period.…”

“…As a result, the solubility of extract yield does not match the compound solubility of natural plant extraction. Moreover, the data on solute solubility in SC-CO 2 research are mostly based on the pure compound (Antonie and Pereira 2019;Guo et al 2019;John et al 2019;Ongkasin et al 2019). To date, no data on the solubility of SIN and ISO in SC-CO 2 extraction from cat's whiskers have been published.…”