Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids

Abstract

The partition coefficients, P IL/w, of several compounds, some of them of biological and pharmacological interest, between water and room-temperature ionic liquids based on the imidazolium, pyridinium, and phosphonium cations, namely 1-octyl-3-methylimidazolium hexafluorophosphate, N-octylpyridinium tetrafluorophosphate, trihexyl(tetradecyl)phosphonium chloride, trihexyl(tetradecyl)phosphonium bromide, trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide, and trihexyl(tetradecyl)phosphonium dicyanamide, were accurately measured. In this way, we extended our database of partition coefficients in room-temperature ionic liquids previously reported. We employed the solvation parameter model with different probe molecules (the training set) to elucidate the chemical interactions involved in the partition process and discussed the most relevant differences among the three types of ionic liquids. The multiparametric equations obtained with the aforementioned model were used to predict the partition coefficients for compounds (the test set) not present in the training set, most being of biological and pharmacological interest. An excellent agreement between calculated and experimental log P IL/w values was obtained. Thus, the obtained equations can be used to predict, a priori, the extraction efficiency for any compound using these ionic liquids as extraction solvents in liquid-liquid extractions.

Phosphonium salts and P-ylides

“…Aimed at developing guidelines for efficient processes, theoretical studies as well as phase diagrams for multiphasic systems were investigated in detail. Experimental and theoretical studies were performed by Rabari et 190 Coutinho and co-workers reported phase diagrams for a series of ionic 192 In particular, the latter PIL was immobilised in alginate capsules and used for the removal of Cd(II) from HCl aqueous solutions. 193 In a study by Soto and co-workers, the liquidliquid equilibria of a ternary system comprising water, n-dodecane and [P 66614 ][Ntf 2 ] were determined.…”

Development of a dispersive liquid-liquid microextraction technique for the analysis of aryloxyphenoxy-propionate herbicides in soy-based foods

“…PB-RTILs are made of tetraalkylphosphonium cations with different anions and have some additional advantages compared to the nitrogen-based RTILs (NB-RTILs), such as very high thermal and chemical stability, higher solvation properties and they are cheaper [18]. There are about 20 different types of PB-RTILs commercially available.…”

“…As a counterpart, due to the typical high viscosities of the RTILs, a dilution with solvents such as methanol or acetonitrile can be necessary before injection into the HPLC column, which decreases the enrichment factor [18].…”

Effect of Methyl Jasmonate on Production of Paclitaxel and Related Taxanes in a Hydrophobic Ionic Liquid-Medium Two Phase Culture System

“…As harmless solvents in contrast to conventional organic solvents, ILs have attracted attention because of their special features such as high thermal stability, negligible volatility, and selective solubility. ILs have been applied for extraction and separation of bioactive compounds of hydrophobic 3-indole-butyric acid, ferulic acid and caffeine acid found in plants [7][8][9][10][11][12][13]. Magnetic ILs such as benzyltrioctylammonium bromotrichloroferrate (III) and 1,12-di(3-hexadecylbenzimidazolium) dodecane bis[(trifluoromethyl)-sulfonyl]imide bromotrichloroferrate (III) have higher extraction efficiencies for DNA molecules [14].…”