1641-36-7Relevant articles and documents
Drug specific, tuning of an ionic liquid's hydrophilic-lipophilic balance to improve water solubility of poorly soluble active pharmaceutical ingredients
McCrary, Parker D.,Beasley, Preston A.,Gurau, Gabriela,Narita, Asako,Barber, Patrick S.,Cojocaru, O. Andreea,Rogers, Robin D.
, p. 2196 - 2202 (2013)
Amphotericin B and itraconazole were used to demonstrate that ionic liquids can be designed or chosen to provide tunable hydrophilicity in one ion and lipophilicity in the other allowing one to match the structural requirements needed to solubilize poorly water soluble active pharmaceutical ingredients. These liquid, amphiphilic excipients could be used as both drug delivery systems and solubilization agents to improve the aqueous solubility of many drugs. The solubility in deionized water, simulated gastric fluid, simulated intestinal fluid, and phosphate buffer solution was greatly improved over current methods for drug delivery by utilizing designed ionic liquids as excipients.
Thermodynamic properties of binary mixtures of n-butylammonium-based ionic liquids with ethanol at T = (293.15–313.15) K
Bittencourt, Samara Storion,Hoga, Heloisa Emi,Torres, Ricardo Belchior,D’Angelo, José Vicente Hallak
, p. 1 - 21 (2018)
In this study, density, speed of sound and viscosity of binary mixtures of ionic liquids + ethanol have been measured as a function of composition at T = (293.15–313.15) K and atmospheric pressure. The ionic liquids studied were: {n-butylammonium acetate (N4Ace), n-butylammonium propanoate (N4Pro), n-butylammonium hexanoate (N4Hex), and n-butylammonium decanoate (N4Dec)}. Excess molar volume, (Formula presented.), deviation in isentropic compressibility, (Formula presented.), deviation in viscosity, (Formula presented.), and excess Gibbs energy of activation of viscous flow, (Formula presented.), were obtained from experimental results and correlated with the Redlich–Kister polynomial equation. Ionic liquids were synthesized and characterized using 1H-NMR, 13C-NMR and FTIR spectroscopy techniques. For all systems studied, the values of (Formula presented.), (Formula presented.) and (Formula presented.) were negative over the entire composition range, whereas (Formula presented.) values were positive over the entire composition range. The results obtained were discussed in terms of structural effects and intermolecular interactions between like and unlike molecules.
Thermodynamic Properties and Intermolecular Interactions of a Series of N-Butylammonium Carboxylate Ionic Liquids
Wei, Ying,Xu, Tongtong,Zhang, Xinyuan,Di, Yang,Zhang, Qingguo
, p. 4475 - 4483 (2018)
A series of new N-butylammonium carboxylate ionic liquids (N-butylammonium formate, N-butylammonium acetate, N-butylammonium propionate, and N-butylammonium butyrate) were synthesized by a one-step method and characterized. The thermodynamic properties such as surface tension, density, electrical conductivity, and dynamic viscosity of the ILs were measured as functions of temperature. Important parameters such as molecular volume, crystal energy, thermal expansion coefficient, standard molar entropy, and the surface properties are estimated by the empirical equations. The Vogel-Fulcher-Tamman (VFT) equation is used to explore the dependence of electrical conductivities and dynamic viscosities on temperature. The relationship between the molar conductivity and the fluidity of the ILs was examined through the use of Walden plots. To describe intermolecular interactions of the N-butylammonium carboxylate ILs, the optimized structures and energetics of ILs are calculated by DFT calculations. The calculated energies showed that the increase in the interaction energies between the ion clusters is the same as the trend of experimental viscosities.
Ionicity and proton transfer in protic ionic liquids
Stoimenovski, Jelena,Izgorodina, Ekaterina I.,MacFarlane, Douglas R.
, p. 10341 - 10347 (2010)
Proton transfer in protic ionic liquids is poorly understood. Some acid/base proton transfer reactions do not proceed to the extent that is expected from ΔpKaaq data from aqueous solutions, yet some do. In this work we have investigated protic ionic liquids obtained by proton transfer from a common acid, acetic acid, to a range of amine bases of similar pKaaq values. Probe indicator observations, transport property data allowing the construction of Walden plots and computational studies all suggest that there is a clear distinction between the behaviour of simple primary vs. tertiary amines, the proton transfer being more complete in the former case than the latter. The origins of this seem to be related to the hydrogen bonding ability of the ammonium ions in providing a good solvating environment for the ions produced by the proton transfer.
Density, viscosity, and refractive index properties for the binary mixtures of n -butylammonium acetate ionic liquid + alkanols at sveral temperatures
Xu, Yingjie,Yao, Jia,Wang, Congmin,Li, Haoran
, p. 298 - 308 (2012)
Densities and viscosities were determined for the binary mixtures of n-butylammonium acetate ionic liquid (N4AC) with methanol, ethanol, n-propanol, and n-butanol at temperatures of (293.15, 298.15, 303.15, 308.15, and 313.15) K under atmospheric pressure. The refractive indices of the above-mentioned binary mixtures were measured at 298.15 K. Excess molar volumes VE, viscosity deviations Δη, and refractive index deviations Δn D were obtained from the experimental data and fitted with the Redlich-Kister equation. The correlation results were in good agreement with the experimental data, and optimal fitting parameters were presented. The results were interpreted in terms of interactions and structural factors of N4AC + alkanols mixtures.
Separate mechanisms of ion oligomerization tune the physicochemical properties of n-butylammonium acetate: Cation-base clusters vs. Anion-acid dimers
Berton, Paula,Kelley, Steven P.,Wang, Hui,Myerson, Allan S.,Rogers, Robin D.
, p. 25544 - 25554 (2017/10/13)
We investigated the ability of the ions comprising protic ionic liquids to strongly interact with their neutral acid and base forms through the characterization of n-butylammonium acetate ([C4NH3][OAc]) in the presence of excess n-butylamine (C4NH2) or excess acetic acid (HOAc). The conjugate and parent acid or base form new nonstoichiometric, noncovalently bound species (i.e., oligomeric ions) which change the physical and chemical properties of the resulting liquids, thus offering tunability. The effects of adding C4NH2 or HOAc to [C4NH3][OAc] on the resulting thermal and spectroscopic properties differ and suggest that C4NH2 interacts primarily with [C4NH3]+ to form 3-dimensional polymeric networks likely similar to those in H2O/[H3O]+, while HOAc interacts primarily with [OAc]- to form oligomeric ions (e.g., [H(OAc)2]-). The densities of the systems increased with the increase of acid content and reached a maximum when the acid molar fraction was 0.90, but decreased with increasing amine concentration. The viscosities decreased significantly with increasing acid or base concentration. The solvent properties of the mixtures were assessed by measuring the solubilities of benzene, ethyl acetate, diethyl ether, heptane, ibuprofen free acid, and lidocaine free base. The solubilities of the organic solutes and active pharmaceutical ingredients can be tuned with the concentration of acid or amine in the mixtures. In addition, crystallization of the active pharmaceutical ingredients can be induced with the modification of the composition of the mixtures. These observations support the usage of these mixtures for the synthesis and purification of acid or basic active pharmaceutical ingredients in the pharmaceutical industry.
Synthesis and characterization of new low-cost ILs based on butylammonium cation and application to lignocellulose hydrolysis
De Andrade Neto, José Carlos,De Souza Cabral, Allex,De Oliveira, Lucas Rissato Dognani,Torres, Ricardo Belchior,Morandim-Giannetti, Andreia De Araújo
, p. 279 - 287 (2016/03/01)
Fourteen ionic liquids (ILs) were obtained and characterized by nuclear magnetic resonance and infra-red spectroscopy. One of these liquids, n-butylammonium acetate, was used in the treatment of coir fiber prior to acid hydrolysis. For this purpose, the fiber was pulped with 8% (w/w) sodium hydroxide for 6 h under 2.5 atm pressure at 137 °C and then treated with IL for 2 h at 90 °C. The samples were hydrolyzed in acetic acid at different concentrations and temperatures. The reducing sugar concentrations were determined in all samples, and the optimal hydrolysis conditions were established (32.2% acetic acid at 122.4 °C). The reaction time was also studied, and the conversion was maximized at 3 h. Under the best hydrolysis conditions, crude fiber, pulping fiber, and IL-treated fiber were hydrolyzed to yield 8.53%, 47.58%, and 89.75% of reducing sugars, respectively.
Synthesis of N4-substituted derivatives of 1-[2- (phosphonomethoxy)ethyl]cytosine and its diisopropyl ester as a model reaction for the synthesis of N4-substituted derivatives of cidofovir
Chalupova, Sarka,Holy, Antonin,Masojidkova, Milena
, p. 2066 - 2074 (2007/10/03)
We have studied the reaction of 1-[2-(phosphonomethoxy)ethyl]cytosine (1) and its diisopropyl ester (2) with triethylammonium hydrogensulfite in 60% aqueous methanol. In the presence of some primary or secondary amine salts, at 25-70 °C, this reaction affords transaminated derivatives 4a-4e and 5a, 5b as main products accompanied by uracil compounds. However, with certain amines the reaction failed.
