Hydrophobic amine-based binary mixtures of active pharmaceutical and food grade ingredients: characterization and application in indium extraction from aqueous hydrochloric acid media

Edgecomb, Joseph; Tereshatov, Evgeny; Zante, Guillaume; Boltoeva, Maria; Folden, III, Charles M.

doi:10.1039/d0gc02452j

Title: Hydrophobic amine-based binary mixtures of active pharmaceutical and food grade ingredients: characterization and application in indium extraction from aqueous hydrochloric acid media

Journal Article · Wed Sep 23 00:00:00 EDT 2020 · Green Chemistry

DOI:https://doi.org/10.1039/d0gc02452j· OSTI ID:1668867

Edgecomb, Joseph ^[1]; Tereshatov, Evgeny ^[2]; Zante, Guillaume ^[3]; Boltoeva, Maria ^[3]; Folden, III, Charles M. ^[2]

Texas A&M University, College Station, TX (United States); Saint Martin’s University, Lacey, WA (United States)
Texas A&M University, College Station, TX (United States)
Université de Strasbourg (France)

The wide spread use of hazardous and expensive solvents for the liquid-liquid extraction (LLE) of critical metals has been a growing source of waste in the metal refinement industry. We have developed and characterized room temperature liquid hydrophobic binary mixtures based on common pharmaceutical and food grade compounds as sustainable, cost effective alternatives to both ionic liquids and conventional solvents. Additionally, we introduce liquid mixtures with Proton Sponge® (1,8-bis(dimethylamino)naphthalene), one of the strongest known organic bases. These mixtures have been applied to the LLE of indium(III) ions from hydrochloric acid solutions, displaying an extraction efficiency greater than 99% in some systems. Here, a systematic approach to identifying the underlying mechanism of extraction, in particular relating to the charge, solubility, and complexation of the indium species in the organic phase has been developed.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Texas A & M Univ., College Station, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Nuclear Physics (NP); USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: FG02-93ER40773; NA-0003180

OSTI ID:: 1668867

Alternate ID(s):: OSTI ID: 1670231

Journal Information:: Green Chemistry, Vol. 2020, Issue 22; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (70)

Assessment of critical minerals: updated application of an early-warning screening methodology McCullough, Erin; Nassar, Nedal T. Mineral Economics, Vol. 30, Issue 3 https://doi.org/10.1007/s13563-017-0119-6	journal	September 2017
Chromatographic and potentiometric determination of dissociation constants of weakly basic Aroma compounds Bitteur, S.; Rosset, R. Chromatographia, Vol. 27, Issue 5-6 https://doi.org/10.1007/BF02260445	journal	March 1989
Preparation and evaluation of ibuprofen beads by melt solidification technique Paradkar, Anant R.; Maheshwari, Manish; Ketkar, Anant R. International Journal of Pharmaceutics, Vol. 255, Issue 1-2 https://doi.org/10.1016/S0378-5173(03)00081-4	journal	April 2003
Indium and thallium extraction into betainium bis(trifluoromethylsulfonyl)imide ionic liquid from aqueous hydrochloric acid media Volia, M. F.; Tereshatov, E. E.; Boltoeva, M. New Journal of Chemistry, Vol. 44, Issue 6 https://doi.org/10.1039/C9NJ04879K	journal	January 2020
Global Substance Flow Analysis of Indium Yoshimura, Akihiro; Daigo, Ichiro; Matsuno, Yasunari MATERIALS TRANSACTIONS, Vol. 54, Issue 1 https://doi.org/10.2320/matertrans.M2012279	journal	January 2013
Enhanced rectal bioavailability of ibuprofen in rats by poloxamer 188 and menthol Yong, Chul Soon; Yang, Chae Ha; Rhee, Jong-Dal International Journal of Pharmaceutics, Vol. 269, Issue 1 https://doi.org/10.1016/j.ijpharm.2003.09.013	journal	January 2004
Deep Eutectic Solvents (DESs) and Their Applications Smith, Emma L.; Abbott, Andrew P.; Ryder, Karl S. Chemical Reviews, Vol. 114, Issue 21 https://doi.org/10.1021/cr300162p	journal	October 2014
Assessing the greenness of some typical laboratory ionic liquid preparations Deetlefs, Maggel; Seddon, Kenneth R. Green Chem., Vol. 12, Issue 1 https://doi.org/10.1039/B915049H	journal	January 2010
Sunscreen Use in Photodermatoses DeLeo, Vincent Dermatologic Clinics, Vol. 24, Issue 1 https://doi.org/10.1016/j.det.2005.09.004	journal	January 2006
Synthesis of Isocyanates from Carboxylic Acids Using Diphenylphosphoryl Azide and 1,8- bis (Dimethylamino) naphthalene Gilman, Jeffrey W.; Otonari, Yoshiko A. Synthetic Communications, Vol. 23, Issue 3 https://doi.org/10.1080/00397919308009785	journal	February 1993
Accuracy of calculated pH-dependent aqueous drug solubility Bergström, Christel A. S.; Luthman, Kristina; Artursson, Per European Journal of Pharmaceutical Sciences, Vol. 22, Issue 5 https://doi.org/10.1016/j.ejps.2004.04.006	journal	August 2004
Methyl Anthranilate as an Aroma Constituent of American wine Nelson, R. R.; Acree, T. E.; Lee, C. Y. Journal of Food Science, Vol. 42, Issue 1 https://doi.org/10.1111/j.1365-2621.1977.tb01217.x	journal	January 1977
Solvent-Free Synthesis of Zeolites from Solid Raw Materials Ren, Limin; Wu, Qinming; Yang, Chengguang Journal of the American Chemical Society, Vol. 134, Issue 37 https://doi.org/10.1021/ja3044954	journal	September 2012
Purification of crude In(OH) ₃ using the functionalized ionic liquid betainium bis(trifluoromethylsulfonyl)imide Deferm, Clio; Luyten, Jan; Oosterhof, Harald Green Chemistry, Vol. 20, Issue 2 https://doi.org/10.1039/C7GC02958F	journal	January 2018
A new approach to PVC-plasticizer interaction by using a Tg concentration power equation Vilics, Tiberiu; Schneider, Hans Adam; Manoviciu, Virginia Polymer, Vol. 38, Issue 8 https://doi.org/10.1016/S0032-3861(96)00722-7	journal	April 1997
Thallium Transfer from Hydrochloric Acid Media into Pure Ionic Liquids Tereshatov, Evgeny E.; Boltoeva, Maria Yu.; Mazan, Valerie The Journal of Physical Chemistry B, Vol. 120, Issue 9 https://doi.org/10.1021/acs.jpcb.5b08924	journal	February 2016
Sustainable hydrophobic terpene-based eutectic solvents for the extraction and separation of metals Schaeffer, Nicolas; Martins, Mónia A. R.; Neves, Catarina M. S. S. Chemical Communications, Vol. 54, Issue 58 https://doi.org/10.1039/C8CC04152K	journal	January 2018
Tunable solvents: Shades of green Abou-Shehada, Sarah; Clark, James H.; Paggiola, Giulia Chemical Engineering and Processing: Process Intensification, Vol. 99 https://doi.org/10.1016/j.cep.2015.07.005	journal	January 2016
Prospect of ionic liquids and deep eutectic solvents as new generation draw solution in forward osmosis process Dutta, Supritam; Nath, Kaushik Journal of Water Process Engineering, Vol. 21 https://doi.org/10.1016/j.jwpe.2017.12.012	journal	February 2018
Improved transdermal permeability of ibuprofen by ionic liquid technology: Correlation between counterion structure and the physicochemical and biological properties Wu, Hao; Deng, Zhaizhu; Zhou, Bijian Journal of Molecular Liquids, Vol. 283 https://doi.org/10.1016/j.molliq.2019.03.046	journal	June 2019
Evidence for a New Crystalline Phase of Racemic Ibuprofen Dudognon, Emeline; Danède, Florence; Descamps, Marc Pharmaceutical Research, Vol. 25, Issue 12 https://doi.org/10.1007/s11095-008-9655-7	journal	June 2008
Application, function, and effects of menthol in cigarettes: A survey of tobacco industry documents Wayne, Geoffrey Ferris; Connolly, Gregory Nicotine & Tobacco Research, Vol. 6, Issue 1 https://doi.org/10.1080/14622203310001649513	journal	February 2004
Ultrasound-assisted ionic liquid-based microextraction combined with least squares support vector machines regression for the simultaneous determination of aluminum, gallium, and indium in water and coal samples Ghasemi, Jahan B.; Zolfonoun, Ehsan Environmental Monitoring and Assessment, Vol. 184, Issue 6 https://doi.org/10.1007/s10661-011-2237-x	journal	July 2011
First evidence of metal transfer into hydrophobic deep eutectic and low-transition-temperature mixtures: indium extraction from hydrochloric and oxalic acids Tereshatov, E. E.; Boltoeva, M. Yu.; Folden, C. M. Green Chemistry, Vol. 18, Issue 17 https://doi.org/10.1039/C5GC03080C	journal	January 2016
Homogeneous Liquid–Liquid Extraction of Metal Ions with a Functionalized Ionic Liquid Vander Hoogerstraete, Tom; Onghena, Bieke; Binnemans, Koen The Journal of Physical Chemistry Letters, Vol. 4, Issue 10 https://doi.org/10.1021/jz4005366	journal	May 2013
Nanostructure, hydrogen bonding and rheology in choline chloride deep eutectic solvents as a function of the hydrogen bond donor Stefanovic, Ryan; Ludwig, Michael; Webber, Grant B. Physical Chemistry Chemical Physics, Vol. 19, Issue 4 https://doi.org/10.1039/C6CP07932F	journal	January 2017
Ionic deep eutectic solvents for the extraction and separation of natural products Huang, Jie; Guo, Xiuyun; Xu, Tianyi Journal of Chromatography A, Vol. 1598 https://doi.org/10.1016/j.chroma.2019.03.046	journal	August 2019
Study of pH-dependent solubility of organic bases. Revisit of Henderson-Hasselbalch relationship Völgyi, Gergely; Baka, Edit; Box, Karl J. Analytica Chimica Acta, Vol. 673, Issue 1 https://doi.org/10.1016/j.aca.2010.05.022	journal	July 2010
Physicochemical studies of lidocaineâmenthol binary systems for enhanced membrane transport Kang, L. International Journal of Pharmaceutics, Vol. 206, Issue 1-2 https://doi.org/10.1016/S0378-5173(00)00505-6	journal	September 2000
First Transition Metal Complex of 1,8-Bis(dimethylamino)naphthalene ( proton sponge ) Yamasaki, Tomoki; Ozaki, Nobutaka; Saika, Yasunari Chemistry Letters, Vol. 33, Issue 7 https://doi.org/10.1246/cl.2004.928	journal	July 2004
Liquid pharmaceuticals formulation by eutectic formation Abbott, Andrew P.; Ahmed, Essa I.; Prasad, Kamalesh Fluid Phase Equilibria, Vol. 448 https://doi.org/10.1016/j.fluid.2017.05.009	journal	September 2017
Copper 3-methylanthranilate [bis(2-amino-3-methylbenzoato)copper(II)] Boudreau, S. M.; Haendler, H. M. Acta Crystallographica Section C Crystal Structure Communications, Vol. 42, Issue 8 https://doi.org/10.1107/S0108270186093800	journal	August 1986
Some solid state properties of enantiomers and their racemates Chickos, J. S.; Garin, D. L.; Hitt, M. Tetrahedron, Vol. 37, Issue 12 https://doi.org/10.1016/S0040-4020(01)97981-5	journal	January 1981
Use of extraction chromatography in the recycling of critical metals from thin film leach solutions Schaeffer, Nicolas; Grimes, Sue M.; Cheeseman, Chris R. Inorganica Chimica Acta, Vol. 457 https://doi.org/10.1016/j.ica.2016.11.020	journal	March 2017
Structure of a zinc 3-methylanthranilate complex: (2-amino-4-methylbenzoato)hydroxozinc(II) Boudreau, S. M.; Haendler, H. M. Acta Crystallographica Section C Crystal Structure Communications, Vol. 48, Issue 4 https://doi.org/10.1107/S0108270191010703	journal	April 1992
Insights into the Nature of Eutectic and Deep Eutectic Mixtures Martins, Mónia A. R.; Pinho, Simão P.; Coutinho, João A. P. Journal of Solution Chemistry, Vol. 48, Issue 7 https://doi.org/10.1007/s10953-018-0793-1	journal	August 2018
Removal of alkali and transition metal ions from water with hydrophobic deep eutectic solvents van Osch, Dannie J. G. P.; Parmentier, Dries; Dietz, Carin H. J. T. Chemical Communications, Vol. 52, Issue 80 https://doi.org/10.1039/C6CC06105B	journal	January 2016
Selective recovery of indium from iron-rich solutions using an Aliquat 336 iodide supported ionic liquid phase (SILP) Van Roosendael, Stijn; Regadío, Mercedes; Roosen, Joris Separation and Purification Technology, Vol. 212 https://doi.org/10.1016/j.seppur.2018.11.092	journal	April 2019
Menthol-based Eutectic Mixtures: Hydrophobic Low Viscosity Solvents Ribeiro, Bernardo D.; Florindo, Catarina; Iff, Lucas C. ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 10 https://doi.org/10.1021/acssuschemeng.5b00532	journal	September 2015
Measurement and Prediction of Solubility of Paracetamol in Water−Isopropanol Solution. Part 1. Measurement and Data Analysis Hojjati, H.; Rohani, S. Organic Process Research & Development, Vol. 10, Issue 6 https://doi.org/10.1021/op060073o	journal	November 2006
Perspective on Solvent Use in the Pharmaceutical Industry Constable, David J. C.; Jimenez-Gonzalez, Conchita; Henderson, Richard K. Organic Process Research & Development, Vol. 11, Issue 1 https://doi.org/10.1021/op060170h	journal	January 2007
Low-Transition-Temperature Mixtures (LTTMs): A New Generation of Designer Solvents Francisco, María; van den Bruinhorst, Adriaan; Kroon, Maaike C. Angewandte Chemie International Edition, Vol. 52, Issue 11 https://doi.org/10.1002/anie.201207548	journal	February 2013
Liquid-Liquid Extraction of Trivalent Gallium, Indium and Thallium from Hydrochloric Acid Solutions by Trioctyl Phosphine Oxide. Sato, Taichi Shigen-to-Sozai, Vol. 112, Issue 2 https://doi.org/10.2473/shigentosozai.112.123	journal	January 1996
The effect of hydrogen bonding on the glass transition temperatures of polymer mixtures Kwei, T. K. Journal of Polymer Science: Polymer Letters Edition, Vol. 22, Issue 6 https://doi.org/10.1002/pol.1984.130220603	journal	June 1984
Hydrophobic eutectic mixtures as volatile fatty acid extractants van den Bruinhorst, Adriaan; Raes, Sanne; Maesara, Sausan Atika Separation and Purification Technology, Vol. 216 https://doi.org/10.1016/j.seppur.2018.12.087	journal	June 2019
Development of hydrophobic deep eutectic solvents for extraction of pesticides from aqueous environments Florindo, C.; Branco, L. C.; Marrucho, I. M. Fluid Phase Equilibria, Vol. 448 https://doi.org/10.1016/j.fluid.2017.04.002	journal	September 2017
Removal of transition metals from rare earths by solvent extraction with an undiluted phosphonium ionic liquid: separations relevant to rare-earth magnet recycling Vander Hoogerstraete, Tom; Wellens, Sil; Verachtert, Katrien Green Chemistry, Vol. 15, Issue 4 https://doi.org/10.1039/c3gc40198g	journal	January 2013
Resin Ion Exchange and Liquid-Liquid Extraction of Indium and Thallium from Chloride Media Tereshatov, E. E.; Boltoeva, M. Yu.; Folden, C. M. Solvent Extraction and Ion Exchange, Vol. 33, Issue 6 https://doi.org/10.1080/07366299.2015.1080529	journal	July 2015
Superheated water extraction, steam distillation and SFE of peppermint oil Ammann, Andreas; Hinz, Dirk C.; Addleman, R. Shane Fresenius' Journal of Analytical Chemistry, Vol. 364, Issue 7 https://doi.org/10.1007/s002160051406	journal	August 1999
Recovery of indium based on the combined methods of ionic liquid extraction and electrodeposition Matsumiya, Masahiko; Sumi, Maori; Uchino, Yuuki Separation and Purification Technology, Vol. 201 https://doi.org/10.1016/j.seppur.2018.02.027	journal	August 2018
Update on Ibuprofen: Review Article Busson, Mervyn Journal of International Medical Research, Vol. 14, Issue 2 https://doi.org/10.1177/030006058601400201	journal	March 1986
Non-aqueous solvent extraction of indium from an ethylene glycol feed solution by the ionic liquid Cyphos IL 101: speciation study and continuous counter-current process in mixer–settlers Deferm, Clio; Onghena, Bieke; Nguyen, Viet Tu RSC Advances, Vol. 10, Issue 41 https://doi.org/10.1039/D0RA04684A	journal	January 2020
Well-Designed Hydrophobic Deep Eutectic Solvents As Green and Efficient Media for the Extraction of Artemisinin from Artemisia annua Leaves Cao, Jun; Yang, Meng; Cao, Fuliang ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 4 https://doi.org/10.1021/acssuschemeng.6b03092	journal	February 2017
Green and Sustainable Solvents in Chemical Processes Clarke, Coby J.; Tu, Wei-Chien; Levers, Oliver Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00571	journal	January 2018
Efficient and Selective Extraction of ^99m TcO ₄ ^– from Aqueous Media Using Hydrophobic Deep Eutectic Solvents Phelps, Tim E.; Bhawawet, Nakara; Jurisson, Silvia S. ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 11 https://doi.org/10.1021/acssuschemeng.8b03950	journal	October 2018
Non-ionic hydrophobic eutectics – versatile solvents for tailored metal separation and valorisation Schaeffer, Nicolas; Conceição, João H. F.; Martins, Mónia A. R. Green Chemistry, Vol. 22, Issue 9 https://doi.org/10.1039/D0GC00793E	journal	January 2020
Stabilizing Unstable Amorphous Menthol through Inclusion in Mesoporous Silica Hosts Cordeiro, Teresa; Castiñeira, Carmem; Mendes, Davide Molecular Pharmaceutics, Vol. 14, Issue 9 https://doi.org/10.1021/acs.molpharmaceut.7b00386	journal	May 2017
Transdermal delivery from eutectic systems: enhanced permeation of a model drug, ibuprofen Stott, P. Journal of Controlled Release, Vol. 50, Issue 1-3 https://doi.org/10.1016/S0168-3659(97)00153-3	journal	January 1998
Hydrophobic deep eutectic solvents as water-immiscible extractants van Osch, Dannie J. G. P.; Zubeir, Lawien F.; van den Bruinhorst, Adriaan Green Chemistry, Vol. 17, Issue 9 https://doi.org/10.1039/C5GC01451D	journal	January 2015
Basicity of 1,8-bis(dimethylamino)naphthalene and 1,4-diazabicyclo[2.2.2]octane in water and dimethylsulfoxide Benoit, Robert L.; Lefebvre, Diane; Fréchette, Monique Canadian Journal of Chemistry, Vol. 65, Issue 5 https://doi.org/10.1139/v87-170	journal	May 1987
New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing Francisco, María; van den Bruinhorst, Adriaan; Kroon, Maaike C. Green Chemistry, Vol. 14, Issue 8 https://doi.org/10.1039/c2gc35660k	journal	January 2012
Characterization of supersaturated lidocaine/polyacrylate pressure sensitive adhesive systems: Thermal analysis and FT-IR Cui, Yong; Frank, Sylvan G. Journal of Pharmaceutical Sciences, Vol. 95, Issue 3 https://doi.org/10.1002/jps.20445	journal	March 2006
Fundamental Properties of Local Anesthetics: I. The Dependence of Lidocaineʼs Ionization and Octanol:Buffer Partitioning on Solvent and Temperature Sanchez, Virgil; Arthur, Richard G.; Strichartz, Gary R. Anesthesia & Analgesia, Vol. 66, Issue 2 https://doi.org/10.1213/00000539-198666020-00011	journal	January 1986
Ionic liquids and deep eutectic solvents for biodiesel synthesis: a review: Ionic liquids for biodiesel synthesis Zhao, Hua; Baker, Gary A. Journal of Chemical Technology & Biotechnology, Vol. 88, Issue 1 https://doi.org/10.1002/jctb.3935	journal	November 2012
Extraction of thallium and indium isotopes as the homologues of nihonium into the ionic liquids Cubova, Katerina; Semelova, Miroslava; Nemec, Mojmir Journal of Radioanalytical and Nuclear Chemistry, Vol. 318, Issue 3 https://doi.org/10.1007/s10967-018-6270-x	journal	October 2018
Speciation of indium( iii ) chloro complexes in the solvent extraction process from chloride aqueous solutions to ionic liquids Deferm, Clio; Onghena, Bieke; Vander Hoogerstraete, Tom Dalton Transactions, Vol. 46, Issue 13 https://doi.org/10.1039/C7DT00618G	journal	January 2017
Purification of indium by solvent extraction with undiluted ionic liquids Deferm, Clio; Van de Voorde, Michiel; Luyten, Jan Green Chemistry, Vol. 18, Issue 14 https://doi.org/10.1039/C6GC00586A	journal	January 2016
Extraction of Gallium(III) from Hydrochloric Acid Solutions by Trioctylammonium-based Mixed Ionic Liquids Katsuta, Shoichi; Okai, Miho; Yoshimoto, Yuki Analytical Sciences, Vol. 28, Issue 10 https://doi.org/10.2116/analsci.28.1009	journal	January 2012
An Overview of Clinical Pharmacology of Ibuprofen Bushra, Rabia; Aslam, Nousheen Oman Medical Journal, Vol. 25, Issue 3 https://doi.org/10.5001/omj.2010.49	journal	July 2010
Thermodynamic studies of mixtures for topical anesthesia: Lidocaine–salol binary phase diagram Lazerges, Mathieu; Rietveld, Ivo B.; Corvis, Yohann Thermochimica Acta, Vol. 497, Issue 1-2 https://doi.org/10.1016/j.tca.2009.08.016	journal	January 2010

Similar Records

Extraction and separation of iridium(Ⅳ) and rhodium(Ⅲ) from hydrochloric acid media by a quaternary ammonium-based hydrophobic eutectic solvent

Journal Article · Sun Apr 25 00:00:00 EDT 2021 · Separation and Purification Technology · OSTI ID:1668867

Zakusilova, Vira; Zante, Guillaume; Tereshatov, Evgeny E.; +2 more

Indium and thallium extraction into betainium bis(trifluoromethylsulfonyl)imide ionic liquid from aqueous hydrochloric acid media

Journal Article · Tue Jan 21 00:00:00 EST 2020 · New Journal of Chemistry · OSTI ID:1668867

Volia, M. F.; Tereshatov, E. E.; Boltoeva, M.; +1 more

Effect of hydrophobic ionic liquids aqueous solubility on metal extraction from hydrochloric acid media: Mathematical modelling and trivalent thallium behavior

Journal Article · Sat Aug 29 00:00:00 EDT 2020 · Separation and Purification Technology · OSTI ID:1668867

Tereshatov, Evgeny E.; Mazan, Valérie; Boltoeva, Maria; +1 more

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY

Title: Hydrophobic amine-based binary mixtures of active pharmaceutical and food grade ingredients: characterization and application in indium extraction from aqueous hydrochloric acid media

Citation Formats

References (70)

Similar Records

Related Subjects