Extraction of Butyric Acid by Phosphonium Decanoate Ionic Liquid

Liquid–liquid equilibrium data for butyric acid (BA) extraction by phosphonium decanoate ionic liquid (IL) were measured and modeled. An extended more general extraction mechanism taking into account differences in IL anion basicities was suggested. The overall extraction mechanism involving three submechanisms of competitive and noncompetitive extraction of BA and water coextraction was successfully applied to the system with phosphonium decanoate. Formation of (p, 1) complexes with p of up to 16 molecules of BA with 1 ion pair of IL was supposed. A 3 times lower value of the stability constant of the first IL–BA bond in decanoate compared with phosphinate ILs could result in easier regeneration of acid-loaded IL in vacuum distillation. Aggregation and micellar structures in water-saturated IL were confirmed by dynamic light scattering measurements. The concentration dependence of equilibrium solvent-phase viscosities goes through a maximum that corresponds with a minimum in the dependencies of density a...

[1]  Š. Schlosser,et al.  Influence of Anion and Cation Structure of Ionic Liquids on Carboxylic Acids Extraction , 2019, Front. Chem..

[2]  J. Jacquemin,et al.  A new insight into pure and water-saturated quaternary phosphonium-based carboxylate ionic liquids: Density, heat capacity, ionic conductivity, thermogravimetric analysis, thermal conductivity and viscosity , 2018, The Journal of Chemical Thermodynamics.

[3]  Š. Schlosser,et al.  Specific phenomena in carboxylic acids extraction by selected types of hydrophobic ionic liquids , 2018, Chemical Papers.

[4]  Š. Schlosser,et al.  Density, Viscosity, and Structure of Equilibrium Solvent Phases in Butyric Acid Extraction by Phosphonium Ionic Liquid , 2017 .

[5]  Š. Schlosser,et al.  New Mechanism and Model of Butyric Acid Extraction by Phosphonium Ionic Liquid , 2016 .

[6]  O. Antzutkin,et al.  Atomistic Insight into Tetraalkylphosphonium-Bis(oxalato)borate Ionic Liquid/Water Mixtures. I. Local Microscopic Structure. , 2015, The journal of physical chemistry. B.

[7]  Shobha Sharma,et al.  Composition dependent structural organization in trihexyl(tetradecyl)phosphonium chloride ionic liquid-methanol mixtures. , 2015, The Journal of chemical physics.

[8]  Š. Schlosser,et al.  Physical properties of phosphonium ionic liquid and its mixtures with dodecane and water , 2014 .

[9]  Š. Schlosser,et al.  Extraction of butyric acid with a solvent containing ammonium ionic liquid , 2013 .

[10]  J. Araújo,et al.  Extraction of l-lactic, l-malic, and succinic acids using phosphonium-based ionic liquids , 2012 .

[11]  Š. Schlosser,et al.  Mass-transfer in pertraction of butyric acid by phosphonium ionic liquids and dodecane , 2011 .

[12]  Š. Schlosser,et al.  Extraction of butyric acid by a solvent impregnated resin containing ionic liquid , 2011 .

[13]  João A. P. Coutinho,et al.  Thermophysical properties of pure and water-saturated tetradecyltrihexylphosphonium-based ionic liquids , 2011 .

[14]  A. Pádua,et al.  Three commentaries on the nano-segregated structure of ionic liquids , 2010 .

[15]  Luís M. N. B. F. Santos,et al.  Solubility of Water in Tetradecyltrihexylphosphonium-Based Ionic Liquids , 2008 .

[16]  Š. Schlosser,et al.  Pertraction of lactic acid through supported liquid membranes containing phosphonium ionic liquid , 2008 .

[17]  Š. Schlosser,et al.  Liquid-liquid equilibria of butyric acid for solvents containing a phosphonium ionic liquid , 2008 .

[18]  Štefan Schlosser,et al.  Extraction of lactic acid by phosphonium ionic liquids , 2007 .

[19]  Š. Schlosser,et al.  Pertraction of organic acids through liquid membranes containing ionic liquids , 2006 .

[20]  A. Pádua,et al.  Nanostructural organization in ionic liquids. , 2006, The journal of physical chemistry. B.

[21]  A. Daugulis,et al.  Phosphonium ionic liquids for degradation of phenol in a two-phase partitioning bioreactor , 2005, Applied Microbiology and Biotechnology.

[22]  A. Covington,et al.  Re-evaluation of stoichiometric dissociation constants from electrochemical cell data for propionic and n-butyric acids at (0 to 60) °C and for some other aliphatic carboxylic acids at (18 or 25) °C in aqueous sodium chloride solutions , 2004 .

[23]  C. King,et al.  Extraction of carboxylic acids with amine extractants. 1. Equilibria and law of mass action modeling , 1990 .

[24]  A. Eyal,et al.  Extraction of strong mineral acids by organic acid-base couples , 1982 .

[25]  Taichi Sato,et al.  The Extraction of Bivalent Transition Metals from Aqueous Chloride Solutions by Long-chain Alkyl Quaternary Ammonium Carboxylates , 1982 .