Extraction of bisphenol F three isomers from water with 1‐octyl‐3‐methylimidazolium tetrafluoroborate ionic liquid

Abstract

The extraction for three isomers of bisphenol F (BPF) was studied in a hydrophobic ionic liquid/water biphasic extraction system. The influences of some factors, such as ionic liquid structure, phase ratio, temperature, pH value, and NaCl concentration on the extraction of BPF three isomers were investigated, and excellent efficiency with more than 99.0 % extraction efficiency was obtained using 1‐octyl‐3‐methylimidazolium tetrafluoroborate ([Omim][BF4]) as an extractant. The extraction mechanism of the hydrogen bonds interaction between [Omim][BF4] and BPF three isomers were proven by 1H‐NMR spectrum and the density functional theory (DFT). From the 1H‐NMR spectrum, the immediate disappearance of the BPF isomer hydroxyl protons upon addition of [Omim][BF4] was found, which indicated the existence of hydrogen bond interaction between BPF isomer and [Omim][BF4]. Through the computer simulation, the hydrogen bonds strength decreased in the order of 2,2′‐BPF > 2,4′‐BPF > 4,4′‐BPF, which is consistent with the descending order of distribution coefficients obtained through the experiments. These results are promising for the liquid‐liquid extraction and enrichment of phenols in related industrial processes.

Estimation of liquid‐liquid equilibrium of type 2 systems (water + valeric acid + monobasic ester or dibasic ester or alcohol) using SERLAS, SERLAS‐modified, and SERLAS‐integrated

“…(3) SERLAS‐i is an extension of the molecular LSER method which captures the physics of hydrogen‐bond formation combined with the group‐contribution methodology and Hildebrand's regular solution theory applicable to polar and associating compounds. At the same time the use of nine molecular descriptors of compounds very different in structure guarantees a large range of applicability of SERLAS‐i to more complex systems and allows for an improved calculative description of the real behaviour of various kinds of mixtures including a ionic liquid, with particular focus on phase behaviour of quaternary LLE systems . By combining Senol's VLE model SERAS (solvation energy relation for associated systems) with SERLAS‐i along with appropriately rearranging the limiting conditions, we will be able to simulate accurately the phase behaviour of complex VLE and VLLE systems .…”

“…Nonetheless, interaction parameters are missing for many complex compounds including ionic liquids and dibasic esters, and predictions with existing parameters have shown appreciable error . Recently, to improve the accuracy of phase equilibrium calculations, newly developed equations of state (EOS), such as APACT, SAFT, HM, CPA‐EOS, DFT, and COSMO‐RS, have originated from the statistical fluid theory coupled with quantum chemistry of LLE, wherein efforts are being made to model novel, complex solvent structures …”

Experimental Methods in Chemical Engineering: Nuclear Magnetic Resonance

“…NMR detects chemical bonds and 1 H spectroscopy detects the hydrogen bond interactions between bisphenol F and an extracting agent in ionic liquids. DFT (Gaussian 09®) supports the experimental data, proving that the extraction mechanism passed through hydrogen bond interaction . The food domain is a missing discipline in Can.…”

Equilibrium study on the reactive extraction of heterocyclic monocarboxylic acids from the aqueous solution using Alamine 300/diluent composite solvent: Optimization and modeling of the solvent effect

“…Particularly, dipole moments and cohesive energy densities are due to polar and dispersion forces that enable to value the magnitude of dipole–dipole interactions in the bulk 22–24 . It is worth noting that the intermolecular hydrogen bonding of components through accepting or donating a proton is also of great importance 5–8,21,25 . Previous studies of reactive mixtures range from experimental studies covering solute–carrier molecular interaction to numerical simulation and thermodynamic modeling studies of phase equilibria, as well as density functional theory (DFT)‐based calculations of hydrogen bond energy levels and lifetimes 7–11,13,15,25–27 .…”

“…It is worth noting that the intermolecular hydrogen bonding of components through accepting or donating a proton is also of great importance 5–8,21,25 . Previous studies of reactive mixtures range from experimental studies covering solute–carrier molecular interaction to numerical simulation and thermodynamic modeling studies of phase equilibria, as well as density functional theory (DFT)‐based calculations of hydrogen bond energy levels and lifetimes 7–11,13,15,25–27 . A noteworthy fact is that isothermal titration calorimetry (ITC) measurements in combination with the simulation data by DFT/Gaussian software provide an improved possibility to elucidate the mechanism of protein‐ligand and solute‐extractant interactions and to easily discriminate between different thermodynamic binding models 21,28–30 …”