Importance of weak interactions in the formulation of organic phases for efficient liquid/liquid extraction of metals

Abstract Recent experimental studies demonstrate the need to take into account weak interactions in the understanding of solvent extraction processes. This well-established industrial technology now beneficiates of a supramolecular approach, complementary to the traditional analysis based on coordination chemistry. In this article, we focus on the integration of a colloidal approach in the analysis of solvent extraction systems: organic phases used are complex fluids, in which extracting molecules self-assemble into reverse aggregates. We detail the available analytical tools used towards characterization of these organic phases and emphasize the recent results in aggregation-driven extraction. All experimental data are discussed in light of theoretical approaches which propose adequate thermodynamic models and shed light on the importance of entropy on the phenomena. Diluent effects and synergism have been successfully rationalized, efficient new formulations based on a physicochemical analysis have been proposed and the door is now open for further development at industrial scale.

[1]  R. Chiarizia,et al.  Aggregation in Organic Solutions of Malonamides: Consequences for Water Extraction , 2009 .

[2]  T. Zemb,et al.  Complexation-induced supramolecular assembly drives metal-ion extraction. , 2014, Chemistry.

[3]  Luc Belloni,et al.  Recycling metals by controlled transfer of ionic species between complex fluids: en route to “ienaics” , 2014, Colloid and Polymer Science.

[4]  O. Diat,et al.  Metal Recognition Driven by Weak Interactions: A Case Study in Solvent Extraction. , 2016, Chemphyschem : a European journal of chemical physics and physical chemistry.

[5]  J. Dufrêche,et al.  Reverse Aggregates as Adaptive Self-Assembled Systems for Selective Liquid-Liquid Cation Extraction , 2013 .

[6]  M. Nilsson,et al.  Synergistic Extraction of Dysprosium and Aggregate Formation in Solvent Extraction Systems Combining TBP and HDBP , 2013 .

[7]  J. Dufrêche,et al.  Liquid-Liquid Extraction of Acids by a Malonamide: II-Anion Specific Effects in the Aggregate-Enhanced Extraction Isotherms , 2014 .

[8]  B. Jönsson Surfactants and Polymers in Aqueous Solution , 1998 .

[9]  D. Bourgeois,et al.  Palladium Isolation and Purification from Nitrate Media: Efficient Process Based on Malonamides , 2019, Solvent Extraction and Ion Exchange.

[10]  H. Eicke,et al.  Is water critical to the formation of micelles in apolar media , 1978 .

[11]  K. Bohinc,et al.  Multicomponent Model for the Prediction of Nuclear Waste/Rare-Earth Extraction Processes , 2018, Langmuir : the ACS journal of surfaces and colloids.

[12]  F. Testard,et al.  Solvent Penetration and Sterical Stabilization of Reverse Aggregates based on the DIAMEX Process Extracting Molecules: Consequences for the Third Phase Formation , 2007 .

[13]  D. Bourgeois,et al.  Palladium Extraction by a Malonamide Derivative (DMDOHEMA) from Nitrate Media: Extraction Behavior and Third Phase Characterization , 2014 .

[14]  S. Dourdain,et al.  Perfluoroalkyl- vs alkyl substituted malonamides: Supramolecular effects and consequences for extraction of metals , 2017 .

[15]  B. Moyer,et al.  LIQUID–LIQUID EQUILIBRIUM ANALYSIS IN PERSPECTIVE II. COMPLETE MODEL OF WATER, NITRIC ACID, AND URANYL NITRATE EXTRACTION BY DI-2-ETHYLHEXYL SULFOXIDE IN DODECANE , 2001 .

[16]  M. Dietz Ionic Liquids as Extraction Solvents: Where do We Stand? , 2006 .

[17]  K. Osseo-asare,et al.  Aggregation, reversed micelles, and microemulsions in liquid-liquid extraction: the tri-n-butyl phosphatediluent-water-electrolyte system , 1991 .

[18]  J. Dufrêche,et al.  Effect of long-range interactions on ion equilibria in liquid–liquid extraction , 2015 .

[19]  A. Ouadi,et al.  Ionic liquid-based uranium(VI) extraction with malonamide extractant: cation exchange vs. neutral extraction , 2016 .

[20]  S. Dourdain,et al.  Synergistic Extraction of Rare Earth Elements from Phosphoric Acid Medium using a Mixture of Surfactant AOT and DEHCNPB , 2017 .

[21]  R. Neuman,et al.  AGGREGATION BEHAVIOR OF COBALT(II), NICKEL(II), AND COPPER(II) BIS(2-ETHYLHEXYL) PHOSPHATE COMPLEXES IN n-HEPTANE , 1998 .

[22]  P. Bauduin,et al.  Self-assembling properties of malonamide extractants used in separation processes , 2008 .

[23]  Wai-Yim Ching,et al.  Long Range Interactions in Nanoscale Science. , 2010 .

[24]  P. Mohapatra,et al.  Chemistry of diglycolamides: promising extractants for actinide partitioning. , 2012, Chemical reviews.

[25]  A. Ouadi,et al.  Is a universal model to describe liquid-liquid extraction of cations by use of ionic liquids in reach? , 2013, Dalton transactions.

[26]  L. Belloni Ionic condensation and charge renormalization in colloidal suspensions , 1998 .

[27]  Z. Kolarik Ionic Liquids: How Far Do they Extend the Potential of Solvent Extraction of f-Elements? , 2013 .

[28]  M. Bešter-Rogač,et al.  Temperature and salt-induced micellization of dodecyltrimethylammonium chloride in aqueous solution: a thermodynamic study. , 2009, Journal of colloid and interface science.

[29]  A. Steinemann,et al.  Exchange of solubilized water and aqueous electrolyte solutions between micelles in apolar media , 1976 .

[30]  D. Harries,et al.  Macromolecular compaction by mixed solutions: Bridging versus depletion attraction , 2016 .

[31]  D. Harries,et al.  Is the depletion force entropic? Molecular crowding beyond steric interactions , 2015 .

[32]  R. Netz,et al.  Electrostatistics of counter-ions at and between planar charged walls: From Poisson-Boltzmann to the strong-coupling theory , 2001 .

[33]  L. Girard,et al.  Solvent Extraction: Structure of the Liquid-Liquid Interface Containing a Diamide Ligand. , 2016, Angewandte Chemie.

[34]  R. Chiarizia,et al.  Application of the Baxter Model for Hard Spheres with Surface Adhesion to SANS Data for the U(VI)−HNO3, TBP−n-Dodecane System , 2003 .

[35]  J. Jestin,et al.  Synergy in Extraction System Chemistry: Combining Configurational Entropy, Film Bending, and Perturbation of Complexation. , 2015, Langmuir : the ACS journal of surfaces and colloids.

[36]  D. Guillaumont,et al.  Liquid-Liquid Extraction of Acids and Water by a Malonamide: I-Anion Specific Effects on the Polar Core Microstructure of the Aggregated Malonamide , 2014 .

[37]  L. Belloni,et al.  Attractive interactions between reverse aggregates and phase separation in concentrated malonamide extractant solutions , 1999 .

[38]  J. Jestin,et al.  Synergism by coassembly at the origin of ion selectivity in liquid-liquid extraction. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[39]  K. Bohinc,et al.  Colloidal Model for the Prediction of the Extraction of Rare Earths Assisted by the Acidic Extractant , 2019, Langmuir : the ACS journal of surfaces and colloids.

[40]  V. Solov'ev,et al.  Determination of successive complexation constants in an ionic liquid: complexation of UO(2)(2+) with NO(3)(-) in C(4)-mimTf(2)N studied by UV-Vis spectroscopy. , 2010, The journal of physical chemistry. B.

[41]  R. Chiarizia,et al.  Third-Phase Formation in the Extraction of Phosphotungstic Acid by TBP in n-Octane , 2010 .

[42]  Sumit Kumar,et al.  Dynamic light scattering study on the aggregation behaviour of N,N,N',N'-tetraoctyl diglycolamide (TODGA) and its correlation with the extraction behaviour of metal ions. , 2010, Journal of colloid and interface science.

[43]  C. Berthon,et al.  Characterisation of the supramolecular structure of malonamides by application of pulsed field gradients in NMR spectroscopy. , 2007, Physical chemistry chemical physics : PCCP.

[44]  Muammer Kaya,et al.  Recovery of metals and nonmetals from electronic waste by physical and chemical recycling processes. , 2016, Waste management.

[45]  J. Dufrêche,et al.  Reverse aggregate nucleation induced by acids in liquid-liquid extraction processes. , 2014, Physical chemistry chemical physics : PCCP.

[46]  G. Cote,et al.  Extraction of Lanthanides(III) and Am(III) by Mixtures of Malonamide and Dialkylphosphoric Acid , 2007 .

[47]  J. Dufrêche,et al.  Thermodynamic Description of Synergy in Solvent Extraction: I. Enthalpy of Mixing at the Origin of Synergistic Aggregation. , 2016, Langmuir : the ACS journal of surfaces and colloids.

[48]  Vladimir S. Kislik,et al.  Solvent extraction : classical and novel approaches , 2012 .

[49]  D. Guillaumont,et al.  Understanding the synergistic effect on lanthanides(III) solvent extraction by systems combining a malonamide and a dialkyl phosphoric acid , 2017 .

[50]  C. Tondre,et al.  EFFECT OF NITRIC ACID EXTRACTION ON PHASE BEHAVIOR, MICROSTRUCTURE AND INTERACTIONS BETWEEN PRIMARY AGGREGATES IN THE SYSTEM DIMETHYLDIBUTYLTETRADECYLMALONAMIDE (DMDBTDMA) / n-DODECANE / WATER: A PHASE ANALYSIS AND SMALL ANGLE X-RAY SCATTERING (SAXS) CHARACTERISATION STUDY , 1998 .

[51]  S. Dourdain,et al.  Ionic liquids as diluents in solvent extraction: first evidence of supramolecular aggregation of a couple of extractant molecules. , 2015, Chemical communications.

[52]  X. L. Le Goff,et al.  Impact of the Long-Range Electronic Effect of a Fluorous Ponytail on Metal Coordination during Solvent Extraction. , 2017, Chemphyschem : a European journal of chemical physics and physical chemistry.

[53]  B. Moyer,et al.  Trefoil-Shaped Outer-Sphere Ion Clusters Mediate Lanthanide(III) Ion Transport with Diglycolamide Ligands. , 2017, Journal of the American Chemical Society.

[54]  T. Zemb,et al.  Depletion of water-in-oil aggregates from poor solvents: Transition from weak aggregates towards reverse micelles , 2015 .

[55]  D. Harries,et al.  Balance of enthalpy and entropy in depletion forces , 2013, 1310.2100.

[56]  Yushu S. Chen,et al.  The role of curvature effects in liquid-liquid extraction: assessing organic phase mesoscopic properties from MD simulations. , 2017, Soft matter.

[57]  H. Aly,et al.  Extraction Behaviors of Trivalent Lanthanides from Nitrate Medium by Selected Substituted Malonamides , 2006 .

[58]  F. Testard,et al.  Influence of the extracted solute on the aggregation of malonamide extractant in organic phases: Consequences for phase stability , 2010 .

[59]  L. Mei,et al.  Europium, uranyl, and thorium-phenanthroline amide complexes in acetonitrile solution: an ESI-MS and DFT combined investigation. , 2015, Dalton transactions.

[60]  Ryan P. Lively,et al.  Seven chemical separations to change the world , 2016, Nature.

[61]  Christopher D. Williams,et al.  A Telescoping View of Solute Architectures in a Complex Fluid System , 2018, ACS central science.

[62]  K. Nash,et al.  Probing organic phase ligand exchange kinetics of 4f/5f solvent extraction systems with NMR spectroscopy , 2016 .

[63]  Yuan Yang,et al.  Tributyl Phosphate Aggregation in the Presence of Metals: An Assessment Using Diffusion NMR Spectroscopy. , 2016, The journal of physical chemistry. B.

[64]  D. Dyrssen,et al.  Solvent extraction of metal ions with mixed ligands—I: Adduct formation of Cu(II) and Zn(II) chelate complexes of thenoyltrifluoroacetone and β-isopropyltropolone , 1964 .

[65]  D. Guillaumont,et al.  Synergism in a HDEHP/TOPO Liquid-Liquid Extraction System: An Intrinsic Ligands Property? , 2016, The journal of physical chemistry. B.

[66]  C. Musikas,et al.  EXTRACTION BY N,N,N',N-TETRAALKYL -2 ALKYL PROPANE -1,3 DIAMIDES. I. H2O, HNO3 and HClO4 , 1994 .

[67]  M. A. Hughes,et al.  The mechanism of extraction of HNO3 and neodymium with diamides , 1994 .

[68]  C. Tondre,et al.  Aggregation and Protonation Phenomena in Third Phase Formation: An NMR Study of the Quaternary Malonamide/Dodecane/Nitric Acid/Water System , 2001 .

[69]  R. Motokawa,et al.  Extraction Performance of a Fluorous Phosphate for Zr(IV) from HNO3 Solution: Comparison with Tri-n-Butyl Phosphate , 2019, Solvent Extraction and Ion Exchange.

[70]  Yushu S. Chen,et al.  Stability of reverse micelles in rare-earth separation: a chemical model based on a molecular approach. , 2017, Physical chemistry chemical physics : PCCP.

[71]  D. F. Evans,et al.  Micelle formation in ethylammonium nitrate, a low-melting fused salt , 1982 .

[72]  Lifeng Zhang,et al.  Metallurgical recovery of metals from electronic waste: a review. , 2008, Journal of hazardous materials.

[73]  D. Bourgeois,et al.  A simple process for the recovery of palladium from wastes of printed circuit boards , 2020, Hydrometallurgy.

[74]  J. Dufrêche,et al.  A predictive model of reverse micelles solubilizing water for solvent extraction. , 2016, Journal of colloid and interface science.

[75]  J. Dufrêche,et al.  Thermodynamic Description of Synergy in Solvent Extraction: II Thermodynamic Balance of Driving Forces Implied in Synergistic Extraction. , 2017, Langmuir : the ACS journal of surfaces and colloids.

[76]  Emma R. Schofield,et al.  Proton Chelating Ligands Drive Improved Chemical Separations for Rhodium. , 2019, Inorganic chemistry.

[77]  M. Jensen,et al.  Influence of aggregation on the extraction of trivalent lanthanide and actinide cations by purified Cyanex 272, Cyanex 301, and Cyanex 302 , 2002 .

[78]  Mario Corti,et al.  Nanometric Surface Oscillation Spectroscopy of Water-Poor Microemulsions. , 2018, Langmuir : the ACS journal of surfaces and colloids.

[79]  Ken A. Dill,et al.  Molecular driving forces : statistical thermodynamics in biology, chemistry, physics, and nanoscience , 2012 .

[80]  N. Kumari,et al.  Dynamic light scattering studies on the aggregation behavior of tributyl phosphate and straight chain dialkyl amides during thorium extraction , 2014 .

[81]  R. A. Grant,et al.  Solvent extraction: the coordination chemistry behind extractive metallurgy. , 2014, Chemical Society reviews.

[82]  O. Diat,et al.  Elucidation of the structure of organic solutions in solvent extraction by combining molecular dynamics and X-ray scattering. , 2014, Angewandte Chemie.

[83]  D. Dreisinger,et al.  A critical review on solvent extraction of rare earths from aqueous solutions , 2014 .

[84]  Aurora E. Clark,et al.  Amphiphile-Based Complex Fluids: The Self-Assembly Ensemble as Protagonist , 2018, ACS central science.