Influence of temperature and alkyl chain length on physicochemical properties of trihexyl- and trioctylammonium based protic ionic liquids

Keshapolla, Dasthaiah; Kancharla, Srinivasarao; Gardas, Ramesh L.

doi:10.1016/j.jct.2019.02.015

Cited by 38 publications

(26 citation statements)

References 59 publications

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“…Undeniably, in the last few years, the biomedical and pharmaceutical industry has turned increasing attention towards ILs due to their yet unexplored potential as bioactive agents or to their ability to solubilize and stabilize drugs [ 33 , 34 , 35 , 36 , 37 , 38 , 39 ]. Furthermore, the cation and/or anion amphiphilic nature can be finely balanced to trigger the self-assembling behavior of ILs [ 40 , 41 , 42 , 43 , 44 ]. In this framework, fatty acids raised remarkable interest as building blocks for ILs containing natural hydrophobic tails [ 45 , 46 , 47 , 48 , 49 , 50 ] and such materials were investigated in pharmaceutical applications [ 42 , 51 , 52 , 53 , 54 ].…”

Section: Introductionmentioning

confidence: 99%

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

et al. 2020

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For topical treatment of skin cancer, the design of pH-responsive nanocarriers able to selectively release the drug in the tumor acidic microenvironment represents a reliable option for targeted delivery. In this context, a series of newly synthesized surface-active fatty acid-protic ionic liquids (FA-PILs), based on tetramethylguanidinium cation and different natural hydrophobic fatty acid carboxylates, have been investigated with the aim of developing a pH-sensitive nanostructured drug delivery system for cutaneous administration in the skin cancer therapy. The capability of FA-PILs to arrange in micelles when combined with each other and with the non-ionic surfactant d-α-Tocopherol polyethylene glycol succinate (vitamin E TPGS) as well as their ability to solubilize imiquimod, an immuno-stimulant drug used for the treatment of skin cancerous lesions, have been demonstrated. The FA-PILs-TPGS mixed micelles showed pH-sensitivity, suggesting that the acidic environment of cancer cells can trigger nanostructures’ swelling and collapse with consequent rapid release of imiquimod and drug cytotoxic potential enhancement. The in vitro permeation/penetration study showed that the micellar formulation produced effective imiquimod concentrations into the skin exposed to acid environment, representing a potential efficacious and selective drug delivery system able to trigger the drug release in the tumor tissues, at lower and less irritating drug concentrations.

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Section: Introductionmentioning

confidence: 99%

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

et al. 2020

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“…A similar observation was reported by Bhattacharyya et al in which the thermal stability of an amino acid ionic liquid with longer alkyl chain attached to the nitrogen, [N 1 , 1 , 14 , 2O12 ][Lys], has a higher thermal stability than another amino acid ionic liquid, [N 1 , 1 , 6 , 2O12 ][Lys], with a relatively shorter alkyl chain branch [ 40 ]. According to Keshapolla et al and Bandres et al, the relationship between high thermal stability and long alkyl chain attached to the ionic liquid could be attributed to the presence of strong intermolecular and intramolecular forces in the alkyl chain [ 41 , 42 ]. In addition, it was observed that the T d values of PILs with a common cation are relatively close to one another and a similar observation was recorded by Cai et al, involving a series of ionic liquids namely triethanolamine methanesulfonate [TEA][mesy], triethanolamine trifluoromethanesulfonate [TEA][OTf] and triethanolamine benzenesulfonate [TEA][Bsa] [ 43 ].…”

Section: Resultsmentioning

confidence: 99%

“…Comparable observations using PIL with ethylammonium cation were also found by several researchers, in which an increasing trending packing efficiency was proportional with the decreasing of molecular weight [ 51 , 55 ]. Notably, the increased alkyl chain length in both cation and anion of the PIL has promoted the steric hindrance and asymmetric nature in the PIL structure as bigger and bulkier PILs result in a lower density value for the PILs [ 40 , 41 ]. This trend can be observed in [BEHA][C6] and [BEHA][C7] as they exhibit the lowest density values.…”

Section: Resultsmentioning

confidence: 99%

“…The volume occupied by one mole of a compound at a given temperature and pressure is denoted as molar volume, V m . The molar volume was calculated by using an empirical equation as shown in Equation (2) and utilizing the experimental densities [ 41 , 58 , 59 , 60 , 61 ]: V m = M/( ρ . N A ) where V m is the molar volume, M is the molar mass of the ammonium-based PILs, ρ is the density of PILs at 303.15 K and N A is Avogadro’s number.…”

Section: Resultsmentioning

confidence: 99%

“…The increasing number of carbon atoms in the alkyl chain of carboxylate anion has resulted in the increment of the S° of the ammonium-based PILs. From the calculated values obtained, [BEHA]-based PILs depicted the highest standard entropy due to their larger size compared to [EHA]-based PILs, which causes the least interaction between cation and anion [ 41 ]. In this work, the standard entropy of [EHA] and [BEHA] PILs increases in the sequence of [C5] < [C6] < [C7].…”

Section: Resultsmentioning

confidence: 99%

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Experimental Investigation on Thermophysical Properties of Ammonium-Based Protic Ionic Liquids and Their Potential Ability towards CO2 Capture

et al. 2022

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Ionic liquids, which are extensively known as low-melting-point salts, have received significant attention as the promising solvent for CO2 capture. This work presents the synthesis, thermophysical properties and the CO2 absorption of a series of ammonium cations coupled with carboxylate anions producing ammonium-based protic ionic liquids (PILs), namely 2-ethylhexylammonium pentanoate ([EHA][C5]), 2-ethylhexylammonium hexanoate ([EHA][C6]), 2-ethylhexylammonium heptanoate ([EHA][C7]), bis-(2-ethylhexyl)ammonium pentanoate ([BEHA][C5]), bis-(2-ethylhexyl)ammonium hexanoate ([BEHA][C6]) and bis-(2-ethylhexyl)ammonium heptanoate ([BEHA][C7]). The chemical structures of the PILs were confirmed by using Nuclear Magnetic Resonance (NMR) spectroscopy while the density (ρ) and the dynamic viscosity (η) of the PILs were determined and analyzed in a range from 293.15K up to 363.15K. The refractive index (nD) was also measured at T = (293.15 to 333.15) K. Thermal analyses conducted via a thermogravimetric analyzer (TGA) and differential scanning calorimeter (DSC) indicated that all PILs have the thermal decomposition temperature, Td of greater than 416K and the presence of glass transition, Tg was detected in each PIL. The CO2 absorption of the PILs was studied up to 29 bar at 298.15 K and the experimental results showed that [BEHA][C7] had the highest CO2 absorption with 0.78 mol at 29 bar. The CO2 absorption values increase in the order of [C5] < [C6] < [C7] anion regardless of the nature of the cation.

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Insight into the Effect of Physicochemical Properties on CO2 Absorption Behavior of Imidazole Anion-Functionalized Ionic Liquids

Wang,

He,

Chen

et al. 2023

J Solution Chem

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Three imidazole anion-functionalized ionic liquids (IFILs) with tributylethylphosphonium ([P 4442 ] + ) cation and imidazolate ([Im] − ), 4-methylimidazolate ([4-MeIm] − ), or 4-bromimidazolate ([4-BrIm] − ) anions were prepared to study the effect of physicochemical properties on CO 2 absorption behavior. Density (ρ), viscosity (η), speed of sound (u) of the studied IFILs were measured, and molecular volume (V m ), standard entropy (S 0 ), lattice energy (U POT ), and isentropic compressibility coe cient (κ s ) were calculated accordingly. CO 2 absorption behavior of [P 4442 ][Im] at T = 313.15-333.15 K and p = 0.2 and 1 bar were investigated as an example. The results show that with the increase of temperature, ρ, η, u, and U POT decrease, while V m , S 0 , and κ s increase, due to a decrease in electrostatic interaction correspondingly. The orders of ρ, u, η, V m , and S 0 values are as follows:while U POT and κ s are in reverse order. Interestingly, CO 2 capture capacity of IFILs is approximately linear with η or κ s . Due to low η and high κ s , CO 2 absorption capacity of [P 4442 ][Im] is almost independent of temperature and partial pressure, as high as 0.90 mol CO 2 /mol IL at 333.15 K and 0.2 bar, indicating that [P 4442 ][Im] has potential applications for CO 2 absorption at high temperature and low pressure.

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Influence of temperature and alkyl chain length on physicochemical properties of trihexyl- and trioctylammonium based protic ionic liquids

Cited by 38 publications

References 59 publications

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

Experimental Investigation on Thermophysical Properties of Ammonium-Based Protic Ionic Liquids and Their Potential Ability towards CO2 Capture

Insight into the Effect of Physicochemical Properties on CO2 Absorption Behavior of Imidazole Anion-Functionalized Ionic Liquids

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