Thermodynamics of solvation of some linear and branched aliphatic aldehydes in water and heptane

Gatta, Giuseppe Della; Badea, Elena; Saczuk, Magdalena

doi:10.1016/j.jct.2010.04.017

Cited by 8 publications

(1 citation statement)

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“…That penalty is mostly reflected in the entropy of cavitation that is not as negative as in the linear alkyl chain in about 10 J K −1 mol −1 . 47 The differentiation between the entropies of solution in all the pairs of isomers are following the trend of ~10 J K −1 mol −1 of entropy of solution increase between the branched and linear ILs as observed from Fig. 3.…”

Section: Resultssupporting

confidence: 64%

The effect of the cation alkyl chain branching on mutual solubilities with water and toxicities

Kurnia

Sintra

Neves

et al. 2014

Phys. Chem. Chem. Phys.

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The design of ionic liquids has been focused on the cation-anion combinations but other more subtle approaches can be used. In this work the effect of the branching of the cation alkyl chain on the design of ionic liquids (ILs) is evaluated. The mutual solubilities with water and toxicities of a series of bis(trifluoromethylsulfonyl)-based ILs, combined with imidazolium, pyridinium, pyrrolidinium, and piperidinium cations with linear or branched alkyl chains, are reported. The mutual solubility measurements were carried out in the temperature range from (288.15 to 323.15) K. From the obtained experimental data, the thermodynamic properties of the solution (in the water-rich phase) were determined and discussed. The COnductor like Screening MOdel for Real Solvents (COSMO-RS) was used to predict the liquid-liquid equilibrium. Furthermore, molecular dynamic simulations were also carried out aiming to get a deeper understanding of these fluids at the molecular level. The results show that the increase in the number of atoms at the cation ring (from five to six) leads to a decrease in the mutual solubilities with water while increasing their toxicity, and as expected from the well-established relationship between toxicities and hydrophobicities of ILs. The branching of the alkyl chain was observed to decrease the water solubility in ILs, while increasing the ILs solubility in water. The inability of COSMO-RS to correctly predict the effect of branching alkyl chains toward water solubility on them was confirmed using molecular dynamic simulations to be due to the formation of nano-segregated structures of the ILs that are not taken into account by the COSMO-RS model. In addition, the impact of branched alkyl chains on the toxicity is shown to be not trivial and to depend on the aromatic nature of the ILs.This journal is

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Section: Resultssupporting

confidence: 64%