Solubility of trioctylmethylammonium chloride in supercritical carbon dioxide and the influence of co-solvents on the solubility behavior

Pitchaiah, K.C.; Lamba, Neha; Sivaraman, N.; Madras, Giridhar

doi:10.1016/j.supflu.2018.04.002

Cited by 27 publications

(11 citation statements)

References 58 publications

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“…Thus, there is no reason to expect that our results should be so similar to the imidazolium IL results. Importantly, a recent report by Sivaraman and co-workers using a tetraalkylammonium IL, similar to the phosphonium used here, did show appreciable solubility, on the order of (0.5 -12.7) x 10 −5 in neat scCO 2 at 313, 323, and 333K over a pressure range of 10-30 MPa [92]. It is interesting to note that only after many attempts to show surfactant dissolution in CO 2 , only a few designer fluorinated surfactants were shown to appreciably dissolve in scCO 2 [31,58,59,93,94].…”

Section: Steady-state Anisotropysupporting

confidence: 69%

“…The evaluation of potential contributions that might be responsible for the C153 response observed herein, including local density augmentation, C153 dimerization (aggregation), and the presence of IL and/or C153/IL aggregates in solution, led us to conclude that the observed effects suggest that IL influences our measurements. The recent demonstration of IL solubility in neat scCO 2 by Sivaraman and co-workers [92] provides context against which we consider our spectroscopic data. Time-resolved fluorescence measurements showed two time constants, with the shorter component used to account for scattered light and the longer time associated with C153 lifetimes.…”

Section: Discussionmentioning

confidence: 99%

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Spectroscopic Studies of a Phosphonium Ionic Liquid in Supercritical CO2

2020

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Fluorescence spectroscopy was used to study a solution comprised of coumarin 153 (C153)+ trihexyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide ([P6,6,6,14]+ [Tf2N]−)+ supercritical CO2 (scCO2). We compare the spectroscopy of C153 in neat scCO2 to that of C153/scCO2 with the addition of ionic liquid (IL). Excitation and emission peak frequencies of C153 in scCO2 and in IL/scCO2 diverged at reduced densities (ρr = ρ/ρc) below the CO2 critical density. At low fluid density, spectral changes in the IL/scCO2 solutions showed evidence that C153 experiences a very different microenvironment—one that is unlike neat scCO2. The data show that the presence of IL clearly influences the C153 excitation and emission profiles. Excitation was broadened and red shifted by >2000 cm−1 and the presence of an additional low-energy emission component that was red shifted by ~3000 cm−1 was clearly visible and not observed in neat scCO2. The solution heterogeneity was controlled by changing the scCO2 density and at high fluid density, both the excitation and emission spectra were more similar to those in neat scCO2. Steady-state anisotropy also showed that at low fluid density, the C153 emission was significantly polarized. Aggregation of C153 has been reported in the literature and this led us to hypothesize the possibility that C153 dimer (aggregation) formation may be occurring in scCO2. Another possible explanation is that dye–IL aggregates may dissolve into the scCO2 phase due to C153 acting as a “co-solvent” for the IL. Time-resolved intensity decay measurements yielded only slightly non-exponential decays with accompanying time constants of ~3–4 ns that were significantly shorter than the 5–6 ns time constants in neat scCO2, which are suggestive of C153–IL interactions. However, these data did not conclusively support dimer formation. Pre-exponential factors of the time constants showed that almost all of the emission was due to monomeric C153.

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Section: Steady-state Anisotropysupporting

confidence: 69%

Section: Discussionmentioning

confidence: 99%

Spectroscopic Studies of a Phosphonium Ionic Liquid in Supercritical CO2

2020

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“…Moreover, the solubility needs to be determined at wide range of temperatures and pressures in order to size and design the process at industrial scale [ 21 ]. Different studies have been carried out to measure the solubility of active pharmaceutical ingredients (APIs) in supercritical CO 2 as solvent via different techniques [ 14 , 22 ]. Therefore, for a API candidate to be processed using supercritical-based technology the solubility must be measured at different conditions, e.g.…”

Section: Introductionmentioning

confidence: 99%

Chloroquine (antimalaria medication with anti SARS-CoV activity) solubility in supercritical carbon dioxide

Pishnamazi

Hosseini

Zabihi

et al. 2021

Journal of Molecular Liquids

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Unfortunately, malaria still remains a major problem in tropical areas, and it takes thousands of lives each year and causes millions of infected cases. Besides, on December 2019, a new virus known as coronavirus appeared, that its rapid prevalence caused the World Health Organization (WHO) to consider it a pandemic. As a potential drug for controlling or treating these two undesired diseases at the cellular level, chloroquine and its derivatives are being investigated, although they possess side effects, which must be reduced for effective and safe treatments. With respect to the importance of this medicine, the current research aimed to calculate the solubility of chloroquine in supercritical carbon dioxide, and evaluated effect of pressure and temperature on the solubility. The pressure varied between 120 and 400 bar, and temperatures between 308 and 338 K were set for the measurements. The experimental results revealed that the solubility of chloroquine lies between 1.64 × 10 −5 to 8.92 × 10 −4 (mole fraction) with different functionality to temperature and pressure. Although the solubility was indicated to be strong function of pressure and temperature, the effect of temperature was more profound and complicated. A crossover pressure point was found in the solubility measurements, which indicated similar behaviour to an inflection point. For the pressures higher than the crossover point, the temperature indicated direct effect on the solubility of chloroquine. On the other hand, for pressures less than the crossover point, temperature enhancement led to a reduction in the solubility of chloroquine. Moreover, the obtained solubility results were correlated via semi-empirical density-based thermodynamic correlations. Five correlations were studied including: Kumar & Johnston, Mendez-Santiago-Teja, Chrastil, Bartle et al., and Garlapati & Madras. The best performance was obtained for Mendez-Santiago-Teja's correlation in terms of average absolute relative deviation percent (12.0%), while the other examined models showed almost the same performance for prediction of chloroquine solubility.

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“…This is because, at a higher temperature, the ethanol as a modifier has higher ability (i) to break solute-matrix interactions, (ii) overlay the active sites thereby preventing re-adsorption or partitioning of the solute back onto these active sites, and (iii) decreases the activation energy barrier of desorption. The particular bioactive compounds have a high molecular weight, thus containing a significantly low vapor pressure due to the abundance of hydrocarbons in their molecular structure (Pitchaiah et al 2018). Thus, the vapor pressure of solutes in the range of 40-80 °C is a dominant factor on the solubility of SIN and ISO.…”

Section: Solubility Datamentioning

confidence: 99%

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

et al. 2021

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In the current study, the solubility of potent bioactive compounds from cat's whiskers (Orthosiphon stamineus), viz. sinensetin (SIN) and isosinensetin (ISO), is measured in ethanol-assisted supercritical carbon dioxide (SC-CO 2 ). Experiments were conducted at temperature and pressure of 40-80 °C and 10-30 MPa, respectively. Three semi-empirical models of Chrastil, del Valle-Aguilera, and Gonzalez were used to correlate the compounds' solubility in SC-CO 2 + ethanol. The highest solubility of SIN and ISO was obtained at 3.945 and 2.323 mg/L, respectively, at 10 MPa and 80 °C. The solubility data revealed the direct effect of temperature, while the pressure has a dual effect of both increasing and decreasing the compounds' solubility. This study revealed the influence of solute's melting point, dipole moment and molecular structure on its solubility in SC-CO 2 + ethanol system. Therefore, SIN has higher solubility in SC-CO 2 + ethanol system due to its lower melting and dipole moment compared to its isomer, ISO. In addition, the solubility of the SIN and ISO data was satisfactorily correlated with all semi-empirical models, with less than 4.0% of the AARD%. The enthalpy of vaporization and solvation for SIN and ISO in SC-CO 2 extraction were determined.

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Solubility of trioctylmethylammonium chloride in supercritical carbon dioxide and the influence of co-solvents on the solubility behavior

Cited by 27 publications

References 58 publications

Spectroscopic Studies of a Phosphonium Ionic Liquid in Supercritical CO2

Spectroscopic Studies of a Phosphonium Ionic Liquid in Supercritical CO2

Chloroquine (antimalaria medication with anti SARS-CoV activity) solubility in supercritical carbon dioxide

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

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