A New Triketone Ligand for Extraction of Lithium from Brines**

Evans, Barbara R.; Popovs, Ilja; Johnson, Katherine R.; Einkauf, Jeffrey D.; Moyer, Bruce A.; Paranthaman, Mariappan Parans

doi:10.1002/cssc.202401600

Title: A New Triketone Ligand for Extraction of Lithium from Brines**

Journal Article · 15 September 2024 · ChemSusChem

DOI: https://doi.org/10.1002/cssc.202401600 · OSTI ID:2477526

^[1];

^[1]

Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Recovery of lithium from brines by liquid-liquid solvent extraction (LLE) with diketones and synergistic co-ligands has been investigated for decades, but industrial application has been limited. In pursuit of a ligand with improved properties, a series of ketonamides with beta-carbonyl groups were designed, synthesized, and tested in extraction of lithium from sulfate and carbonate simulants of clay mineral tailing leachates. The best performing ligand, a novel tricarbonyl amide, was characterized for lithium extraction with and without four synergistic co-ligands. Further, the tricarbonyl amide combined with the synergistic co-ligand Cyanex-923 was absorbed on a resin support. The ligand-modified resin was tested for performance in extraction of dilute brine simulants and up to 60 % recovery of lithium was achieved.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Energy Efficiency Office. Advanced Materials & Manufacturing Technologies Office (AMMTO); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 2477526

Journal Information:: ChemSusChem, Journal Name: ChemSusChem Journal Issue: 3 Vol. 18; ISSN 1864-5631

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

References (27)

Organocatalytic Enantio‐ and Diastereoselective Conjugate Addition to Nitroolefins: When β‐Ketoamides Surpass β‐Ketoesters Du, Haiying; Rodriguez, Jean; Bugaut, Xavier Chemistry – A European Journal, Vol. 20, Issue 27 https://doi.org/10.1002/chem.201402192	journal	June 2014
Separation and purification of lithium by solvent extraction and supported liquid membrane, analysis of their mechanism: a review: Separation and purification of lithium Swain, Basudev Journal of Chemical Technology & Biotechnology, Vol. 91, Issue 10 https://doi.org/10.1002/jctb.4976	journal	April 2016
Environmentally benign techniques of lithium extraction from salt lakes: a review Hu, Yaoxian; Su, Hui; Zhu, Zhaowu Environmental Chemistry Letters, Vol. 22, Issue 1 https://doi.org/10.1007/s10311-023-01669-0	journal	November 2023
Materials for lithium recovery from salt lake brine Xu, Ping; Hong, Jun; Qian, Xiaoming Journal of Materials Science, Vol. 56, Issue 1 https://doi.org/10.1007/s10853-020-05019-1	journal	August 2020
A review of lithium extraction from natural resources Liu, Yubo; Ma, Baozhong; Lü, Yingwei International Journal of Minerals, Metallurgy and Materials, Vol. 30, Issue 2 https://doi.org/10.1007/s12613-022-2544-y	journal	December 2022
Separation of lithium from other alkali metal ions by reversed phase chromatography Lee, D. A. Journal of Chromatography A, Vol. 26 https://doi.org/10.1016/S0021-9673(01)98890-9	journal	January 1967
Extraction equilibria of lithium with N , N -bis(2-ethylhexyl)-3-oxobutanamide and tributyl phosphate in kerosene and FeCl 3 Ji, Lianmin; Li, Lijuan; Shi, Dong Hydrometallurgy, Vol. 164 https://doi.org/10.1016/j.hydromet.2016.06.022	journal	September 2016
Novel approaches for lithium extraction from salt-lake brines: A review Liu, Gui; Zhao, Zhongwei; Ghahreman, Ahmad Hydrometallurgy, Vol. 187 https://doi.org/10.1016/j.hydromet.2019.05.005	journal	August 2019
Recovery of lithium from mineral resources: State-of-the-art and perspectives – A review Li, Huan; Eksteen, Jacques; Kuang, Ge Hydrometallurgy, Vol. 189 https://doi.org/10.1016/j.hydromet.2019.105129	journal	November 2019
Recent advances in lithium extraction from lithium-bearing clay minerals Zhao, Hao; Wang, Yang; Cheng, Hongfei Hydrometallurgy, Vol. 217 https://doi.org/10.1016/j.hydromet.2023.106025	journal	March 2023
Mechanism and process for the extraction of lithium from the high magnesium brine with N,N-bis(2-ethylhexyl)-2-methoxyacetamide in kerosene and FeCl3 Ji, Lianmin; Zhang, Licheng; Shi, Dong Journal of Industrial and Engineering Chemistry, Vol. 113 https://doi.org/10.1016/j.jiec.2022.05.053	journal	September 2022
Towards a low-carbon society: A review of lithium resource availability, challenges and innovations in mining, extraction and recycling, and future perspectives Tabelin, Carlito Baltazar; Dallas, Jessica; Casanova, Sophia Minerals Engineering, Vol. 163 https://doi.org/10.1016/j.mineng.2020.106743	journal	March 2021
Global lithium resources: Relative importance of pegmatite, brine and other deposits Kesler, Stephen E.; Gruber, Paul W.; Medina, Pablo A. Ore Geology Reviews, Vol. 48 https://doi.org/10.1016/j.oregeorev.2012.05.006	journal	October 2012
Recovery of lithium from spodumene-bearing pegmatites: A comprehensive review on geological reserves, beneficiation, and extraction Kundu, Tonmoy; Rath, Swagat S.; Das, Surya Kanta Powder Technology, Vol. 415 https://doi.org/10.1016/j.powtec.2022.118142	journal	February 2023
Lithium recovery from brines: A vital raw material for green energies with a potential environmental impact in its mining and processing Flexer, Victoria; Baspineiro, Celso Fernando; Galli, Claudia Inés Science of The Total Environment, Vol. 639 https://doi.org/10.1016/j.scitotenv.2018.05.223	journal	October 2018
Lithium Recovery from the Mother Liquor Obtained in the Process of Li₂CO₃ Production Wang, Junfeng; Yang, Shicheng; Bai, Ruibing Industrial & Engineering Chemistry Research, Vol. 58, Issue 3 https://doi.org/10.1021/acs.iecr.8b05495	journal	January 2019
Lithium Recovery from Oil and Gas Produced Water: A Need for a Growing Energy Industry Kumar, Amit; Fukuda, Hiroki; Hatton, T. Alan ACS Energy Letters, Vol. 4, Issue 6 https://doi.org/10.1021/acsenergylett.9b00779	journal	May 2019
Synergistic Solvent Impregnated Resin for Adsorptive Separation of Lithium Ion Onishi, Kenta; Nakamura, Takahide; Nishihama, Syouhei Industrial & Engineering Chemistry Research, Vol. 49, Issue 14 https://doi.org/10.1021/ie100145d	journal	June 2010
The Separation of Lithium from Alkali Metal Ions^1,2 Guter, Gerald A.; Hammond, George S. Journal of the American Chemical Society, Vol. 78, Issue 20 https://doi.org/10.1021/ja01601a009	journal	October 1956
Assessment of lithium criticality in the global energy transition and addressing policy gaps in transportation Greim, Peter; Solomon, A. A.; Breyer, Christian Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-18402-y	journal	September 2020
Revealing the relationship between liquid fragility and medium-range order in silicate glasses Shi, Ying; Deng, Binghui; Gulbiten, Ozgur Nature Communications, Vol. 14, Issue 1 https://doi.org/10.1038/s41467-022-35711-6	journal	January 2023
Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds Allen, Frank H.; Kennard, Olga; Watson, David G. Journal of the Chemical Society, Perkin Transactions 2, Issue 12 https://doi.org/10.1039/p298700000s1	journal	January 1987
Novel Extraction of Chromatographic Resins Based on Tetraalkyldiglycolamides: Characterization and Potential Applications Horwitz, E. P.; McAlister, D. R.; Bond, A. H. Solvent Extraction and Ion Exchange, Vol. 23, Issue 3 https://doi.org/10.1081/SEI-200049898	journal	May 2005
Synthesis and first X-ray structures of cobalt(II) and cobalt(III) complexes bearing 2,4-dioxo-alkanoic acid dialkylamide ligands Wang, Jian; Morra, Nicholas A.; Zhao, Hongda Canadian Journal of Chemistry, Vol. 87, Issue 1 https://doi.org/10.1139/v08-151	journal	January 2009
Lithium Recovery from Aqueous Resources and Batteries: A Brief Review Li, Ling; Deshmane, Vishwanath G.; Paranthaman, M. Parans Johnson Matthey Technology Review, Vol. 62, Issue 2 https://doi.org/10.1595/205651317X696676	journal	April 2018
Price bubbles in lithium markets around the world Restrepo, Natalia; Uribe, Jorge M.; Guillen, Montserrat Frontiers in Energy Research, Vol. 11 https://doi.org/10.3389/fenrg.2023.1204179	journal	June 2023
Technology for the Recovery of Lithium from Geothermal Brines Stringfellow, William T.; Dobson, Patrick F. Energies, Vol. 14, Issue 20 https://doi.org/10.3390/en14206805	journal	October 2021

Similar Records

Supercritical fluid extraction of thorium and uranium ions from solid and liquid materials with fluorinated [beta]-diketones and tributyl phosphate

Journal Article · 1994 · Environmental Science and Technology; (United States) · OSTI ID:7243165

Lin, Y; Wai, C M; Jean, F M; +1 more

Hafnium extraction from acidic chloride solutions by Cyanex 923

Journal Article · 1996 · Solvent Extraction and Ion Exchange · OSTI ID:374494

El-Ammouri, E; Distin, P A

New directions and principles for solvent extraction for recovery of lithium from aqueous brines and mineral leachates: A brief review

Journal Article · 2025 · Sustainable Materials and Technologies · OSTI ID:3002661

Evans, Barbara R.; Jayanthi, Kumar; Popovs, Ilja; +2 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Brines
Co-ligands
Lithium
Solvent extraction
β-Diketone

Title: A New Triketone Ligand for Extraction of Lithium from Brines**

Citation Formats

References (27)

Similar Records

Related Subjects