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WO2025198666A1 - Compositions, systèmes et procédés d'extraction d'un ou plusieurs métaux d'une solution - Google Patents

Compositions, systèmes et procédés d'extraction d'un ou plusieurs métaux d'une solution

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Publication number
WO2025198666A1
WO2025198666A1 PCT/US2024/057479 US2024057479W WO2025198666A1 WO 2025198666 A1 WO2025198666 A1 WO 2025198666A1 US 2024057479 W US2024057479 W US 2024057479W WO 2025198666 A1 WO2025198666 A1 WO 2025198666A1
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WO
WIPO (PCT)
Prior art keywords
lithium
reagent composition
group
combinations
metal
Prior art date
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Pending
Application number
PCT/US2024/057479
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English (en)
Inventor
Jack Bender
Richelle LYNDON
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Energy Exploration Technologies Inc
Original Assignee
Energy Exploration Technologies Inc
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Filing date
Publication date
Application filed by Energy Exploration Technologies Inc filed Critical Energy Exploration Technologies Inc
Publication of WO2025198666A1 publication Critical patent/WO2025198666A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B26/00—Obtaining alkali, alkaline earth metals or magnesium
    • C22B26/10—Obtaining alkali metals
    • C22B26/12—Obtaining lithium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0426—Counter-current multistage extraction towers in a vertical or sloping position
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0446—Juxtaposition of mixers-settlers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0492—Applications, solvents used
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D9/00—Crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
    • C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
    • C22B3/22—Treatment or purification of solutions, e.g. obtained by leaching by physical processes, e.g. by filtration, by magnetic means, or by thermal decomposition
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
    • C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
    • C22B3/26—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds
    • C22B3/32—Carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
    • C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
    • C22B3/26—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds
    • C22B3/40—Mixtures
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B26/00—Obtaining alkali, alkaline earth metals or magnesium
    • C22B26/10—Obtaining alkali metals
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P10/00—Technologies related to metal processing
    • Y02P10/20—Recycling

Definitions

  • the disclosure relates to compositions, systems and methods for extracting one or more metals (e.g., lithium) from a solution (e.g., an aqueous brine).
  • a solution e.g., an aqueous brine
  • Lithium batteries are at the forefront of electricity storage technologies because inter alia they charge faster, last longer and have a higher power density to provide more battery life in a lighter package than conventional batteries. Lithium storage devices are useful for electrification of the transportation sector, electric vehicles, battery storage for electric utilities and in many other applications to reduce carbon emissions and store electricity.
  • Lithium is typically extracted from underground deposits of brine water and ore comprised of compounds containing lithium. Brines from salars and salt lakes, as well as spodumene ores, are the primary sources of lithium, while geothermal brines represent secondary sources. Lithium-containing brine obtained from a source is initially concentrated to a suitable concentration (e.g., about 6,000 ppm Li) for viable recovery. Conventional methods of lithium extraction rely on brine evaporation in open ponds to maximize element concentration for further purification; however, these methods are very slow (evaporation of ponds to the desired level can take up to 24 months) and strongly dependent on region-specific weather conditions that vary throughout the year. When the brine contains a low concentration of magnesium, conventional lithium extraction methods are only able to extract little or no lithium. There is a need for improved systems and methods to recover metals such as lithium from aqueous solutions having low concentrations of magnesium.
  • reagent compositions comprising: at least one amide extractant capable of selectively extracting one or more metals, compounds thereof (e.g., compounds other than salts), salts thereof, or combinations thereof, from an aqueous solution; and optionally comprising at least one modifier, at least one diluent, or a combination thereof.
  • the one or more metals may include lithium, magnesium, calcium, boron, potassium, sodium, or combinations thereof.
  • the one or more metals include a lithium salt, magnesium salt, calcium salt, boron salt, potassium salt, sodium salt or combinations thereof.
  • the one or more metals include lithium or a lithium salt.
  • the at least one amide extractant comprises an amide compound chosen from the following Formula (I), Formula (II), Formula (III), or combinations thereof: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 and R 11 is each independently hydrogen, a methyl group, an ethyl group, a straight or branched C3-C20 alkyl group, a C3-C12 cycloalkyl group having a single ring structure, a Cs-Cio aromatic ring group, a C1-C20 alkylphenyl group, a dihydrobenzodi oxene group, a straight or branched C1-C20 alkanol group, a straight or branched C1-C20 alky ldiol group, a straight or branched C3-C20 alkenyl group, a straight or branched C3-C20 alkenyl group, a straight
  • the at least one amide extractant may be present in the reagent composition in an amount of greater than 0 wt%, or about 1 wt% to about 99 wt%, or any individual value or sub-range within these ranges, based on the total weight of the reagent composition.
  • a weight ratio of the at least one amide extractant to the at least one modifier is about 1:10 to about 100: 1, or any individual value or sub-range within this range.
  • the reagent compositions further include a diluent such as an alcohol, an organophosphorous solvent, or a combination thereof.
  • a diluent such as an alcohol, an organophosphorous solvent, or a combination thereof.
  • Suitable diluents include, but are not limited to, octanol, tri decanol, 2-ethyl-l -hexanol, 3-methyl-l -butanol, isoamyl alcohol, 2-hexyl decanol, octanoic acid, trioctylphosphine oxide (e.g., Cyanex® 923), petroleum distillates solvent (e.g., Orform® SX80), aromatic C9-C10 solvent (e.g., Shellsol® Al 50), a kerosene (e.g., Orform® SX1 1), dibutyl carbitol, dichloromethane, trioctylmethylammonium chloride (e.g
  • the at least one diluent may be present in the reagent composition in an amount of greater than 0 wt%, or about 1 wt% to about 99 wt%, or any individual value or sub-range w ithin these ranges, based on the total weight of the reagent composition
  • the reagent compositions include at least one modifier.
  • Suitable modifiers include one or more functional group having a dipole moment and/or that is attached to a highly polar ionic bond.
  • the at least one modifier comprises an aliphatic component that is attracted to non-polar moieties of the at least one amide extractant.
  • the at least one modifier includes one or more functional group chosen from a diether, amide, imide, ketone, alcohol, ether, alkyl phosphine, phosphate, ester, phosphonic acid, phosphonic acid, phosphoric acid and/or nitrile.
  • Suitable modifiers include, but are not limited to, 1 ,6-di-t-butoxy hexane, di(ethylene glycol) di butyl ether, 1,4-bis-t-butoxy butane. 2-ethylhexyl succinimide. 4-t-butylcyclohexanone.
  • IDA iminodiacetic acid
  • TXIB 2,2,4-trimethyl-l,3- pentanediol diisobutyrate
  • TDA ethyoxylated isotri decyl phosphate
  • cy decanol 1- methyl-3-octylimidazolium chloride, trihexyltetradecylphosphonium chloride, l-decyl-3- methylimidazolium tetrafluoroborate, 7-ethyl-2-methyl-undecanol, hexyl 3- methylimidazolium chloride, trimethyl nonanol.
  • about 70% to about 99%, or about 95%, or any individual value or sub-range within these ranges, of the lithium is stripped from the metal rich organic phase.
  • the overall extraction of lithium from the aqueous solution is greater than about 70%, greater than about 80%, greater than about 90%, greater than about 92%, or about 70% to about 99%, about 80% to about 93, or any individual value or sub-range within these ranges.
  • the selectivity of the reagent composition for lithium over magnesium is about 1 to about 50, about 5 to about 30, or about 10 to about 25.
  • FIG. 1 shows a schematic representation of a zwitterionic extractant when contacted with a solution containing inorganic salts forming an inorganic-organic double salt (IODS) can be formed using lithium chloride (LiCl) as an example.
  • IODS inorganic-organic double salt
  • FIG. 2 is a schematic of a direct metal extraction sy stem for recovering a target metal (e.g., lithium) from an aqueous feed solution (e.g., a brine).
  • a target metal e.g., lithium
  • aqueous feed solution e.g., a brine
  • a depurator vessel includes a single depurator vessel as well as more than one depurator vessel.
  • the term “about” in connection with a measured quantity refers to the normal variations in that measured quantity as expected by one of ordinary skill in the art in making the measurement and exercising a level of care commensurate with the objective of measurement and the precision of the measuring equipment. In certain embodiments, the term “about” includes the recited number ⁇ 10%, such that “about 10” would include from 9 to 11. [0021] The term “at least about'’ in connection with a measured quantity refers to the normal variations in the measured quantity, as expected by one of ordinary skill in the art in making the measurement and exercising a level of care commensurate with the objective of measurement and precisions of the measuring equipment and any quantities higher than that.
  • the term “at least about” includes the recited number minus 10% and any quantity that is higher such that “at least about 10” would include 9 and anything greater than 9. This term can also be expressed as “about 10 or more.” Similarly, the term “less than about” typically includes the recited number plus 10% and any quantity' that is lower such that “less than about 10” would include 11 and anything less than 11. This term can also be expressed as “about 10 or less.”
  • Weight percent if not otherwise indicated, is based on an entire composition free of any volatiles, that is, based on dry solids content. Parts per million (ppm) unless otherwise indicated is on the basis of weight.
  • metal refers to the recited metal element and includes compounds (i.e.. other than salts) containing the metal, salts containing the metal and/or combinations thereof.
  • lithium refers to lithium compounds, lithium salts and lithium-containing molecules.
  • trace or “trace amount” as used herein refers to the amount of a component in a solution being less than about 1 part per million by weight (ppmw).
  • substantially free refers to trace amounts of a component in a fluid, less than trace amounts of the component in the fluid or a non-detectable amount of the component in the fluid.
  • reagent compositions containing one or more amide extractants for selectively extracting one or more target metals (e.g., lithium), compounds thereof, salts thereof (e.g., lithium chloride), or combinations thereof from a solution (e.g., an aqueous brine).
  • target metals e.g., lithium
  • compounds thereof, salts thereof e.g., lithium chloride
  • a solution e.g., an aqueous brine.
  • the reagent compositions described herein provide high extraction and stripping performances in, for example, aqueous brines containing about 10 g/L lithium, lithium compounds and/or lithium salts together with magnesium, magnesium compounds and/or magnesium salts dissolved or suspended therein.
  • Reagent compositions as described herein are suitable to extract the one or more metals, compounds thereof, salts thereof, or combinations thereof in a solvent extraction process without the need to centrifuge and/or separate the organic and aqueous phases.
  • reagent compositions as disclosed provide good kinetics in liquid-liquid solvent extraction operations.
  • the reagent compositions include zwitterionic amide extractants for use in methods of solvent extraction of one or more alkali metals (e.g., lithium and/or lithium containing compounds such as lithium salts including lithium chloride).
  • the extractants and methods described herein can be highly selective for one or more target metals or metal containing compounds such as metal salts (e.g., lithium chloride).
  • it was determined that the reagent compositions as described herein are suitable to concentrate the metal and/or metal compounds (e.g., LiCl) dramatically with a selectivity that was far greater than expected.
  • the solvent extraction methods according various embodiments herein are operable using a conventional solvent extraction process and the system is suitable for stripping with water to a relatively high concentration of metal or metal compounds (e.g., lithium chloride) in the recovery solution. It has been found that the extraction of the metals and metal-containing compounds and the production of a recovery stream containing the concentrated metals and/or compounds is suitable for downstream use as battery grade (e.g., lithium salt) production.
  • metal or metal compounds e.g., lithium chloride
  • Amide extractants as described herein may be zwitterionic extractants having a positive charge and a negative charge on the same organic molecule. This makes these compounds intra-ion organic salts, and are often self-associating in the bulk organic.
  • an inorganic-organic double salt can be formed as shown in FIG. 1 using lithium chloride (LiCl) as an example. Without being bound by any particular theory, it is believed that transfer of the LiCl occurs by making an emulsion to increase the surface area.
  • the extractant is suitable to bond with the lithium salt at the interface forming the IODS.
  • the emulsion may be allowed to coalesce once extraction is complete so the phases can be separated.
  • the organic solution is typically washed or scrubbed to remove entrained water or loaded impurities. It is then stripped with water. This is considered an atypical liquid-liquid solvent extraction process due to the lack of an activation/deactivation mechanism using acid/base.
  • zwitterions can work essentially as neat formulations of extractant and modifier.
  • the unloaded formulation is a two-component system: at least one amide extractant; and at least one modifier.
  • the amide extractant and modifier and their respective concentrations may be chosen based on a particular aqueous solution containing one or more target metals, compounds thereof, salts thereof, or combinations thereof.
  • Extractants and chemicals useful in the systems and methods described herein can be synthesized at a relatively low cost with low toxicity.
  • Systems and methods according to embodiments are anticipated to be less expensive and product a higher purity of target metal (e.g., lithium) than using conventional adsorption technologies.
  • the inventive systems and methods can be integrated with traditional solvent extraction processes and/or bipolar electrodialysis (BPED) processes to further purify and concentrate the target metal (e.g., lithium).
  • BPED bipolar electrodialysis
  • reagent compositions comprising one or more extractant(s) that are selective for one or more target metals including compounds thereof, salts thereof, and/or combinations thereof.
  • the reagent compositions contain at least one amide extractant suitable to extract lithium and/or lithium salts.
  • Suitable extractants include amide extractants, for example, containing an amide compound and/or an amide base structure including sulfonamides.
  • the metal-selective reagent compositions described herein can be a solution of a polar or nonpolar organic/inorganic liquid phase or a mixture of polar and/or nonpolar liquids that contain, for example, C, S, N, O, halides etc.
  • the reagent compositions contain aliphatic or aromatic amides, diamides, polyamides, diketoamides, thioamides, carbazide, and/or semi-carbazide and may have a density of at least about 0.5 g/L.
  • the amide extractant does not use a proton transfer mechanism. Without being bound by any particular theory, it is believed that extractants as described herein work by inducing a zwitterionic charge based on resonance structures.
  • the extractants described herein may be suitable to extract lithium as a salt (e.g., lithium chloride, etc.).
  • the reagent compositions may be free of an extractant that uses a proton transfer mechanism.
  • the one or more target metals or metal compounds may be dissolved and/or dispersed within a solvent (e.g., an aqueous solution).
  • a solvent e.g., an aqueous solution
  • the solvent is a metal- containing aqueous solution, for example, a metal -containing brine, brine from a salar, product stream from a pond evaporation process, product stream from a processing plant, or combinations thereof.
  • the aqueous solution is a brine containing greater than about 60,000 ppm of magnesium, compounds thereof, salts thereof, or combinations thereof, and at least about 150 ppm of lithium, compounds thereof, salts thereof, or combinations thereof.
  • the at least one amide extractant are independently capable of selectively extracting lithium, magnesium, calcium, boron, potassium, or sodium, or combinations thereof.
  • the at least one amide extractant is capable of selectively extracting one or more lithium compounds, one or more magnesium compounds, one or more calcium compounds, one or more boron compounds, one or more potassium compounds, or one or more sodium compounds, or combinations thereof.
  • suitable extractants may be capable of extracting one or more lithium salt, one or more magnesium salt, one or more calcium salt, one or more boron salt, one or more potassium salt, or one or more sodium salt, or combinations thereof.
  • suitable extractants are capable of selectively extracting, lithium, one or more lithium compounds such as one or more lithium salts, or combinations thereof.
  • the at least one amide extractant selectively extracts a lithium salt over one or more magnesium salts, one or more calcium salts, one or more boron salts, one or more potassium salts, or one or more sodium salts, and/or combinations thereof.
  • Suitable amide extractants for use in reagent compositions as described herein include one or more amide compound chosen from the following Formula (I), Formula (II), Formula (III), or combinations thereof: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 and R 11 is each independently hydrogen, a methyl group, an ethyl group, a straight or branched C3-C20 alkyl group, a C3-C12 cycloalkyl group having a single ring structure, a Cs-Cio aromatic ring group, a C1-C20 alkylphenyl group, a dihydrobenzodi oxene group, a straight or branched C1-C20 alkanol group, a straight or branched C1-C20 alky I diol group, a straight or branched C3-C20 alkenyl group, a straight or branched C
  • R 5 . R 7 , R 8 , R 9 , R 10 and R 11 may be substituted with a N. O or S. and wherein R 6 is a bond, a methyl group, an ethyl group, a straight or branched C3-C20 alkyl group, a C3-C12 cycloalkyl group having a single ring structure, a Ce-Cio aromatic ring group, a C3-C20 alkylphenyl group, a straight or branched C3-C20 alkenyl group, a straight or branched C3-C20 alkynyl group, a thiol group, wherein at least one carbon atom of R 6 may be substituted w ith N, O or S.
  • At least one amide extractant in the reagent composition is of Formula (I), wherein R 1 and R 2 is each independently a straight or branched C3-C8 alkyl and R 3 is H.
  • at least one amide extractant is of Formula (II) wherein R 4 and R 7 is each independently a straight or branched C3-C8 alkyl, R 5 and R 8 are H, and R 6 is a Cs-Ce cycloalkyl.
  • at least one amide extractant is of Formula (I) wherein R 2 is a straight or branched C3-C8 alkyl, R 3 is H and R 1 is methyl.
  • At least one amide extractant in the reagent composition is of Formula (I) wherein R 2 is H, R 1 and R 3 is each independently a straight or branched C3-C8 alkyl.
  • at least one amide extractant is of Formula (I) wherein R 2 is a straight or branched C3-C8 alky l, R 3 is H, and R 1 is an ethyl group.
  • at least one amide extractant is of Formula (I) wherein R 2 is a Ce aromatic ring group, R 3 is H, and R 1 is a methyl group.
  • At least one amide extractant is of Formula (I) wherein R 2 is H, R 3 a Ci alkylphenyl group, and R 1 is a straight or branched C3-C8 alkyl group.
  • at least one amide extractant is of Formula (II) w herein R 7 , R 8 and R 4 are H, R 6 is a bond, and R 5 is a straight or branched C3-C8 alkyl.
  • at least one amide extractant is of Formula (I) wherein R 2 is a straight or branched C3-C8 alkyl, R 3 is H and R 1 is a dihydrobenzodioxene group.
  • At least one amide extractant is of Formula (I) wherein R 2 is a Ce aromatic ring group, R 3 is H, and R 1 is a straight or branched C3-C8 alkyl. In yet further embodiments, at least one amide extractant is of Formula (I), wherein R 2 and R 3 are H, and R 1 is a C3-C8 alky ldiol group. In further embodiments, at least one amide extractant is of Formula (I) wherein R 2 is an O substituted C3-C8 alkanol, R 3 is H, and R 1 is a straight or branched Cs-Cs alkyl. In yet further embodiments, at least one amide extractant is of Formula (III) wherein R 10 is H and R 9 and R 11 is each independently a straight or branched C3-C8 alkyl.
  • the at least one amide extractant may be present in the reagent composition in an amount of about 5 wt % to about 100 wt%, about 10 wt% to about 90 wt%, about 20 wt% to about 800 wt%, about 30 wt% to about 70 wt%, about 40 wt% to about 50 wt%, about 10 wt% to about 50 wt%, or any individual value or sub-range within these ranges, based on the total weight of the reagent composition.
  • the amide extractant is present in the reagent composition in an amount of at least about 5 wt%, at least about 10 wt%, at least about 15 wt%, at least about 20 wt%, at least about 25 wt%, at least about 30 wt%, at least about 40 wt%, at least about 50 wt%, or any individual value or subrange within these ranges.
  • the amide extractant is present in the reagent composition in an amount of about 45 wt%, about 46 wt%, about 47 wt%, about 48 wt%, about 49 wt%, about 50 wt%, about 51 wt%, about 52 wt%, about 53 wt%, about 54 wt, or about 55 wt%. In some embodiments, the amide extractant is present in the reagent composition in an amount of about 50 wt%.
  • the reagent compositions described herein further include at least one modifier, at least one diluent, or a combination thereof.
  • “Modifiers” refer to chemical compounds designed to affect the properties of other molecules, materials and/or solutions.
  • “Diluents” refer to one or more substance that is added to the reagent compositions to alter the concentration of other components (e.g., one or more extractant, one or more modifier) contained therein and/or to alter the viscosity of the reagent composition.
  • Modifiers as described herein may be used to stabilize the IODS. This can be helpful as the polarity of the organic solvent is not high enough to stabilize the highly ionic character of the IODS.
  • Suitable modifiers for inclusion in reagent compositions as described herein include compounds having one or more functional group with a dipole moment and/or that are attached to a highly polar ionic bond. This may “shield” the ionic moieties and helps to solubilize the IODS.
  • the at least one modifier has an aliphatic component that is attracted to non-polar moieties of the at least one amide extractant.
  • the at least one modifier includes one or more functional group chosen from a diether, imide, ketone, alcohol, ether, alkyl phosphine, phosphate, ester, phosphonic acid, phosphonic acid, phosphoric acid and/or nitrile.
  • Suitable modifiers for use in reagent compositions as described herein may be chosen from 1,6-di-t-butoxy hexane, di(ethylene glycol) dibutyl ether. 1 ,4-bis-t-butoxy butane, 2- ethylhexyl succinimide, 4-t-butylcyclohexanone, l-butyl-3-methylimidazolium methyl sulfate, iminodiacetic acid (IDA), dodecanol, 2,2,4-trimethyl-l,3-pentanediol diisobutyrate (TXIB), ethoxylatedisotridecyl phosphate (TDA), cy decanol, l-methyl-3-octylimidazolium chloride, trihexyltetradecylphosphonium chloride, l-decyl-3-methylimidazolium tetrafluoroborate, 7-
  • IDA
  • the at least one modifier is present in the reagent composition in an amount of about 0 wt% to about 95 wt%, about 5 wt% to about 80 wt%, about 10 wt% to about 80 wt%, about 20 wt% to about 70 wt%, about 30 wt% to about 60 wt%, about 50 wt% to about 90 wt%, or any individual value or sub-range within these ranges, based on the total weight of the reagent composition.
  • the modifier is present in the reagent composition in an amount of at least about 25 wt%, at least about 30 wt%, at least about 40 wt%, at least about 50 wt%, or any individual value or sub-range within these ranges. In one or more embodiments, the modifier is present in the reagent composition in an amount of about 40 wt%, about 41 wt%, about 42 wt%, about 43 wt%, about 44 wt%, about 45 wt%, about 46 wt%, about 47 wt%, about 48 wt%, about 49 wt%, about 50 wt%. about 51 wt%, or about 52 wt%. In some embodiments, the modifier is present in the reagent composition in an amount of about 50 wt%.
  • the weight ratio of the amide extractant to the modifier in the reagent composition is about 1: 100 to about 100: 1, about 1:90 to about 90: 1, about 1 :80 to about 80: 1, about 1: 70 to about 70: 1, about 1 :60 to about 60: 1, about 1:50 to about 50: 1, about 1 :40 to about 40: 1, about 1 :30 to about 30: 1, about 1:25 to about 25: 1, about 1 :20 to about 20: 1, about 1: 15 to about 15: 1, about 1 :10 to about 10: 1, about 1:5 to about 5: 1, about 1:2 to about 1:2, about 1 : 10 to about 100: 1, or any individual value or sub-range within these ranges.
  • the weight ratio of the amide extractant to the modifier is at least about 1 : 10, at least about 1:5, at least about 1 :2, at least about 1 : 1, at least about 2: 1, at least about 5: 1, at least about 10: 1, or any individual value or sub-range within these ranges.
  • Suitable diluents include, but are not limited to, an alcohol, an organophosphorous solvent, or a combination thereof.
  • the compositions contain organic and inorganic solvents including, but not limited to, tributyl phosphate, alcohols, kerosene, sulfonated kerosene, ionic liquids.
  • the at least one diluent may be chosen from octanol, tridecanol, 2-ethy 1-1 -hexanol.
  • 3-methyl-l -butanol isoamyl alcohol, 2-hexyl decanol, octanoic acid, trioctylphosphine oxide (e.g., Cyanex® 923), petroleum distillates solvent (e.g., Orform® SX80), aromatic C9-C10 solvent (e.g., Shellsol® A150), a kerosene (e.g., Orform® SX11), dibutyl carbitol, dichloromethane, trioctylmethylammonium chloride (e.g., Aliquat 336), chloroform, or a combination of any two or more thereof.
  • solvent e.g., Orform® SX80
  • aromatic C9-C10 solvent e.g., Shellsol® A150
  • a kerosene e.g., Orform® SX11
  • dibutyl carbitol dichloromethane
  • trioctylmethylammonium chloride e
  • the at least one diluent is present in the reagent composition in an amount of about 0 wt% to about 90 wt%, about 5 wt% to about 80 wt%, about 10 wt% to about 70 wt%, about 20 wt% to about 60 wt%, about 40 wt% to about 50 wt%, or any individual value or sub-range within these ranges, based on the total weight of the reagent composition.
  • the diluent is present in the reagent composition in an amount of about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt%. In some embodiments, the diluent is present in the reagent composition in an amount of about 0 wt% or less than about 1 wt%.
  • Reagent compositions are comprised of an amide extractant and optionally may be combined with at least one modifier and/or at least one diluent.
  • a diluent is combined with the amide extractant, for example, to provide a target reagent concentration and/or to provide a target viscosity.
  • Suitable reagent concentrations for an amide extractant in a diluent are about 1 wt% to about 99 wt%, or any individual value or sub-range within these ranges.
  • the viscosity of the amide extractant is adjusted by combining the extractant(s) with a diluent while mixing at about 20°C to about 50°C, about 30°C to about 50°C, or any individual value or sub-range within these ranges, to form one or more reagent having a low viscosity' of about 0.1 cP to about 15 cP, or any individual value or sub-range within this range.
  • the amide extractant are combined to form an extractant mixture.
  • Each extractant or the extractant mixture may be combined with a modifier while mixing at about 20°C to about 50°C, about 30°C to about 50°C, or any individual value or subrange within these ranges, to form the reagent composition.
  • a diluent may or may not be present and/or combined with the amide extractant and/or the mixture of the extractant with the modifier.
  • the amide extractant may be combined with the modifier over a range of suitable concentrations and ratios to form the reagent composition.
  • the viscosity of the resulting reagent composition may be about 0.1 cP to about 100 cP. or any individual value or sub-range within this range.
  • systems described herein include recovering a metal from an aqueous solution, comprising: a metal separation and transfer system comprising an adsorbent selective to adsorb a target metal from an aqueous feed solution, the metal separation and transfer system comprising an inlet for a solvent to elute the adsorbent to form an eluate comprising the target metal; an extraction system in fluid communication with the eluate, wherein the extraction system forms a target metal rich solution; and a purification system in fluid communication with the target metal rich solution, wherein the purification system isolates the target metal from the target metal rich solution.
  • a metal separation and transfer system comprising an adsorbent selective to adsorb a target metal from an aqueous feed solution, the metal separation and transfer system comprising an inlet for a solvent to elute the adsorbent to form an eluate comprising the target metal
  • an extraction system in fluid communication with the eluate, wherein the extraction system forms a target metal rich solution
  • the systems and methods include a liquid-liquid solvent extraction system suitable for extracting one or more target metals (e.g., lithium), compounds thereof, salts thereof (e.g., LiCl), or combinations thereof, from an aqueous steam (e.g., a brine), alone or in combination with one or more of a purification system, a concentration system and/or a conversion system.
  • a target metals e.g., lithium
  • aqueous steam e.g., a brine
  • suitable aqueous solutions contain low to high concentrations of magnesium (e.g., about 0 ppm to about 10,000 ppm) in combination with low to high concentrations of lithium (e g., about 1 ppm to about 25.000 ppm).
  • suitable aqueous solutions contain magnesium at a high concentration (e g., 10,000 ppm) together with a low to high concentration of lithium (e.g., about 1 ppm to about 25,000 ppm).
  • Suitable aqueous solutions which can be processes by systems and methods described herein additionally can include low to high concentration of calcium (e.g., about 0 ppm to about 5,000 ppm), a low to high concentration of potassium (e.g., about 0 ppm to about 30,000 ppm), a low to high concentration of sodium (e.g., about 0 ppm to about 40.000 ppm), and/or a low to high concentration of boron (e.g., about 0 ppm to about 5,000 ppm).
  • the aqueous feed 202 contains salts of at least about 0.01 v .% Li, at least about 0.01 wt% Mg, at least about 0.01 wt% Na, at least about 0.01 wt% Ca, at least about 0.01 wt% B, and at least about 0.01 wt% K, or any individual values or sub-ranges within these ranges.
  • the aqueous feed 202 contains salts of about 0.01 wt% to about 10 wt% Li, about 0.01 wt% to about 10 wt% Mg, about 0.01wt% to about 10 wt% Na, about 0.01 wt% to about 10 wt% Ca, about 0.01 wt% to about 10 wt% B, and 0.01 wt% to about 10 wt% K.
  • Systems and methods disclosed herein can perform lithium-selective separation via solvent extraction at temperatures of about 0 °C to about 100 °C. Similarly, the inventive systems and methods can perform lithium-selective transfers to downstream processes at about 0 °C to about 100 °C. The concentration of lithium in the transferred fluid can range from about 150 ppm to about 100.000 ppm.
  • the phase break may occur within about 1 minute to about 30 minutes with or without external aids.
  • External aids can include, but are not limited to, heat, fractal mixing, centrifugal separation, and/or membrane separation.
  • the separation operation does not necessarily require acid and base adjustment.
  • Lithium can be stripped off of the lithium-loaded organic solution exiting the solvent extraction system using deionized water at about room temperature to about 50°C.
  • the strip solution is replenished with fresh reagent composition and recycled to the solvent extraction process to increase the target metal (e.g., lithium) concentration in the strip solution to a high concentration (e.g., about 25,000 ppm Li).
  • a system 200 for recovering one or more target metals (e.g., lithium), compounds thereof, salts thereof, or combinations thereof from an aqueous feed solution (e.g., a brine) according to embodiments herein is shown in FIG. 2.
  • An aqueous feed solution containing one or more metals (e.g., a brine) enters a liquid-liquid solvent extraction system 204.
  • a suitable aqueous feed solution 202 contains one or more metals, compounds thereof, salts thereof, or combinations thereof. Suitable metals include, but are not limited to, lithium, magnesium, calcium, potassium, sodium, and/or boron.
  • the aqueous feed solution 202 can be a product solution from another operation, an eluate from an adsorption process, a recycle stream from another operation, a product stream from a lithium battery recycling operation, a natural brine and/or a manufactured brine.
  • the aqueous feed solution contains about 1 ppm to about 25,000 ppm of lithium, about 0 ppm to about 10,000 ppm of magnesium, about 0 ppm to about 5,000 ppm of calcium, about 0 ppm to about 30,000 ppm of potassium, about 0 ppm to about 40,000 ppm of sodium, and/or about 0 ppm to about 5,000 ppm of boron, or any individual value or sub-range within these ranges.
  • the aqueous feed comprises lithium at a concentration of about 10 ppm to about 25,000 ppm, about 100 ppm to about 20,000 ppm, about 1000 ppm to about 15.000 ppm, about 5.000 ppm to about 12.000 ppm. or any individual value or sub-range within these ranges.
  • the aqueous feed 202 comprises magnesium at a concentration of about 100 ppm to about 10,000 ppm, about 200 ppm to about 8,000 ppm, about 300 ppm to about 5,000 ppm, about 500 ppm to about 2.000 ppm. or any individual value or sub-range within these ranges.
  • the aqueous feed comprises calcium at a concentration of about 0.1 ppm to about 5,000 ppm, about 0.2 ppm to about 4,000 ppm, about 0.4 ppm to about 3,000 ppm, about 0.5 ppm to about 2,000 ppm, or any individual value or sub-range within these ranges.
  • the aqueous feed solution 202 can include water, dilute acids, dilute bases or neutral aqueous solution of alkali metal halides, sulfates and/or nitrates, which can build a target metal (e g., Li) concentration of more than 2 wt% at room temperature or higher temperatures.
  • a target metal e g., Li
  • the aqueous feed solution 202 contains potassium at a concentration of about 50 ppm to about 30,000 ppm of potassium, about 100 ppm to about 25,000 ppm, about 200 ppm to about 20,000 ppm, about 500 ppm to about 15,000 ppm, about 1,000 ppm to about 10,000 ppm, or any individual value or sub-range within these ranges.
  • the aqueous may contain sodium at a concentration of about 50 ppm to about 40,000 ppm, about 100 ppm to about 30,000 ppm. about 500 ppm to about 20,000 ppm, about 1,000 ppm to about 10,000 ppm, or any individual value or sub-range within these ranges.
  • the aqueous feed may contain boron at a concentration of about 1 ppm to about 5,000 ppm of boron, about 2 ppm to about 4,000 ppm, about 5 ppm to about 3,000 ppm, about 10 ppm to about 2,000 ppm, or any individual value or sub-range within these ranges.
  • a metal depleted aqueous solution 206 is formed.
  • the metal depleted aqueous solution 206 may be recycled back to combine with the aqueous feed solution 202 and/or may be sent to another process for purification and/or removal of one or more additional metal, compounds thereof, salts thereof, or combinations thereof using solvent extraction, and/or may be sent to another metal removal process.
  • phase break occurs within 1 to 30 minutes with or without external aids to divide the combined solution into the metal depleted aqueous phase 206 and the metal rich organic phase 208.
  • External aids can include, but are not limited to, heat, fractal mixing, centrifugal separation, and/or membrane separation.
  • the solvent extraction operation 204 does not necessarily require acid and base adjustment.
  • the inventive reagent compositions may be combined with an organic solvent (e.g., a kerosene) to form the organic solution.
  • the at least one amide extractant in the reagent composition is suitable to selectively extract one or more target metals including compounds thereof, salts thereof, or combinations thereof from the aqueous fee solution 202 into the organic solution.
  • combining one or more reagent composition with the organic solvent increases the extraction efficiency, selectivity and/or extraction rate for one or more target metal including compounds thereof, salts thereof, and/or combinations thereof.
  • the metal rich organic solution 208 contains mass ratios of Mg/Li, Ca/Li. K/Li. Na/Li, Na/Li of less than about 50. or any individual value or sub-range within these ranges. In some embodiments, the metal rich organic solution 208 contains mass ratios of Mg/Li, Ca/Li, K/Li, Na/Li, Na/Li independently about 1 :50 to about 50:1, about 1 :40 to about 40: 1, about 1:30 to about 30: 1, about 1:20 to about 20:1. about 1 : 10 to about 10: 1, about 1 :5 to about 5: 1, about 1 :2 to about 2: 1, or any individual value or sub-range within these ranges.
  • the metal rich organic phase may be configured to flow to one or more downstream unit operation processes 210 to recover the one or more target metals that have been extracted from the aqueous solution.
  • the downstream unit operations 210 are chosen from another solvent extraction, organic/inorganic sorbents, metal organic frameworks/imprinted polymers, ion exchange, liquid membranes, reverse osmosis, nanofiltration, electrodialysis, or combinations thereof.
  • the one or more downstream unit operations 210 can independently or together for a metal rich solution 212 that optionally can be combined with the metal rich solution 208.
  • Metal rich solution 212 may be directed to a final processing system 214 to separate the one or more target metals, compounds thereof, salts thereof, or combinations thereof from the metal rich solution 208, 212 to provide a pure metal product 216 (e.g., lithium, a lithium salt, such as LiCl. etc.) suitable for use in other processes and products (e.g., lithium batteries).
  • the post-processed solutions 216 contain lower metal impurities (e.g., Mg, Ca, K, Na, B), compounds thereof, salts thereof, or combinations thereof and/or a higher concentration of the one or more target metals (e.g., Li), compounds thereof, salts thereof, or combinations thereof.
  • the metal rich solution 212 contains mass ratios of Mg/Li, Ca/Li, K/Li, Na/Li, Na/Li of less than about 50, or any individual value or sub-range within these ranges.
  • the metal rich organic solution 212 contains mass ratios of Mg/Li, Ca/Li. K/Li, Na/Li. Na/Li independently about 1:50 to about 50: 1, about 1:40 to about 40:1, about l:30 to about 30: 1, about 1:20 to about 20: 1, about L lO to about 10: 1, about 1:5 to about 5: 1, about 1:2 to about 2:1, or any individual value or sub-range within these ranges.
  • the resulting metal rich solution(s) 208, 212 may be converted into one or more target metal product 216 (e.g., lithium hydroxide, lithium carbonate, etc.) using BPED and/or crystallization in a final processing operation 214.
  • a post-treatment final processing 214 through an ion transport mechanism such as EDR, reverse osmosis, nanofiltration, BPED, adsorption, absorption, or combinations thereof can be used to regenerate metal depleted solutions 218 exiting the final processing 218 and generate a higher metal concentrate solution.
  • the described systems and methods may regenerate one or more target metal selective separation medium and the target metal selective transferring medium in a continuous flow process for reuse in the solvent extraction system 204 and/or various unit operations 210.
  • Systems and methods disclosed herein can perform lithium-selective separation at temperatures of about 0 °C to about 100 °C. Similarly, the inventive systems and methods can perform lithium-selective transfers at about 0 °C to about 100 °C.
  • the concentration of lithium in the transferred fluid can range from about 0 ppm to about 100,000 ppm.
  • the one or more target metals, compounds thereof, salts thereof, or combinations thereof can be stripped off of the metal rich organic solution 208, 212 from the solvent extraction system 204 and/or the one or more downstream unit operations 210 using deionized water at about room temperature to about 50°C.
  • the strip solution can be recycled to increase the lithium concentration in the strip solution to high concentration (e.g., about 25,000 ppm Li).
  • inventive reagent compositions comprising: adsorbing a target metal from an aqueous solution onto an adsorbent selective for the target metal; eluting the adsorbent to form an eluate comprising the target metal; extracting the target metal from the eluate to form a target metal rich solution; and purifying the target metal rich solution to isolate the target metal from the target metal rich solution.
  • Reagent compositions according to embodiments herein are suitable for use in a liquidliquid solvent extraction process.
  • an aqueous feed solution e.g., a lithium-containing brine
  • organic solution e.g., a large organic to aqueous ratio may be needed to extract a target metal, compound thereof, salt thereof, or combinations thereof (e.g., lithium, lithium salt, lithium chloride, etc.) as the molar ratio of the extractant to the target metal may be about 1 : 1.
  • the aqueous solution may be a metal-containing brine (e.g., a lithium-containing brine), brine from a salar.
  • the aqueous feed solution contains lithium, magnesium, calcium, boron, potassium, sodium, or combinations thereof.
  • the aqueous feed solution comprises a lithium salt, magnesium salt, calcium salt, boron salt, potassium salt, sodium salt, or combinations thereof.
  • the aqueous feed solution comprises lithium or a lithium salt.
  • the one or more target metals, compounds thereof, salts thereof, or combinations for extraction using the described methods may be lithium chloride, lithium sulfate, lithium hydroxide, lithium nitrate, or combinations thereof.
  • the aqueous solution is a brine containing greater than about 60,000 ppm of magnesium, compounds thereof, salts thereof, or combinations thereof, and at least about 150 ppm of lithium, compounds thereof, salts thereof, or combinations thereof.
  • the aqueous solution may be contacted with a magnesium selective reagent composition, a calcium selective reagent composition, a boron selective reagent composition, or combinations thereof, prior to contacting the aqueous solution with the reagent composition to extract the one or more metals.
  • Removing magnesium, calcium, and/or boron metals, compounds thereof, salts thereof, or combinations thereof may improve the selectivity of a downstream lithium, compounds thereof, salts thereof, or combinations thereof solvent extraction process.
  • the inventive reagent compositions may be combined with an organic solvent (e.g., a kerosene) to form the organic solution.
  • the at least one amide extractant in the reagent composition is suitable to selectively extract one or more target metals including compounds thereof, salts thereof, or combinations thereof from the aqueous fee solution 202 into the organic solution.
  • combining one or more reagent composition with the organic solvent increases the extraction efficiency, selectivity and/or extraction rate for one or more target metal including compounds thereof, salts thereof, and/or combinations thereof.
  • the methods include stripping the one or more metals from the metal rich organic phase.
  • the stripping of the reagent can be accomplished with water.
  • the metal depleted organic solvent may be returned to the solvent extraction process for further contact with incoming aqueous feed.
  • the metal depleted organic solvent is replenished with fresh reagent composition to ensure efficiency of the continuous process.
  • the concentration of lithium salt e.g., lithium chloride
  • the concentration of lithium salt can be increased to at least 20,000 ppm at which point the stripping efficiency drops below 90%. This does not limit the concentration of the strip solution but may alter the amount of extractant necessary to keep extraction efficiency in an effective range.
  • about 70% to about 99%, or at least about 95%, or any individual value or subrange within these ranges of the one or more metals is stripped from the metal rich organic phase.
  • the methods include contacting the aqueous solution with the reagent composition as described herein.
  • the reagent composition may be contained in an organic solvent to form an organic solution.
  • the method further include extracting the one or more metals, compounds thereof, salts thereof, or combinations thereof from the aqueous solution into the organic solution containing the reagent composition until reaching equilibrium to form a metal depleted aqueous phase and a metal rich organic phase.
  • the methods include separating the metal depleted aqueous phase from the metal compound rich organic phase.
  • the methods may further include contacting the metal depleted aqueous phase with fresh reagent composition and further extracting the one or more metals, compounds thereof, salts thereof, or combinations thereof, from the aqueous solution into the metal rich organic phase (or fresh organic solution) until reaching equilibrium. This process may be repeated to further extract more target metal(s) from the aqueous phase using fresh reagent composition until the metal compound depleted aqueous phase is free or substantially free of the one or more target metals, compounds thereof, salts thereof, or combinations thereof.
  • the methods further include emulsifying the metal rich organic phase.
  • Emulsifying the organic phase can increase the surface area of the extractants to provide more bonding sites for the amide extractant to bond with the one or more target metals, compounds thereof, salts thereof, or combinations thereof.
  • the target metal is lithium, lithium-containing compounds, lithium salts, or combinations thereof, and the selectivity of the amide extractant, or a mixture thereof for lithium over magnesium is about 1 to about 50, about 5 to about 30, or about 10 to about 25.
  • Example 1 Contact evaluations of amide extractants with aqueous brine solutions
  • Table 2 shows analyses of the strip solutions from the experiment conducted with respect to Table 1. As shown in Table 2, the strip solutions show suitable Li/divalent and Li/monovalent selectivity.
  • Table 8 shows the extraction results when other extractants were used to extract lithium from a synthetic brine solution.
  • the elevated stripping temperature aided in both the effectiveness of the stripping process and the viscosity of the solution. Concentrating the stripping solution up to about 25000 ppm Li can be achieved with the amide extractant.
  • Neat amide reagents were stirred in a closed vessel with a brine (i. e. , water) over a 19- week period.
  • the reagent concentration in samples were determined using gas chromatography analysis.
  • the reagent concentration did not change over the 19-week period. This indicates that there was no loss of reagent due to degradation. Since entrainment constantly occurs in a solvent extraction system, the reagent is still lost from the system; however, because degradation of the amide reagents is so low, no negative effects are expected. Without being bound by any particular theory, it is believed that a reagent would have to degrade by about 30-40% over 20 weeks for there to be an impact during the solvent extraction process.
  • Table 11 shows the composition of the feed solutions for various low concentration magnesium-containing brines.
  • Table 11 shows the selectivity data for the extractions while Table 12 shows the extraction and strip data for the experiments.
  • Table 14 shows the composition of the feed solutions for the real and synthetic Brine F used in this example. Table 1 - Composition of the feed tested in these experiments
  • Extractant El provided adequate loading of lithium with no measurable loss of aqueous.

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Abstract

Sont divulgués des compositions de réactif contenant au moins un agent d'extraction d'amide permettant d'extraire sélectivement un ou plusieurs métaux, des composés de ceux-ci, des sels de ceux-ci ou des combinaisons de ceux-ci, d'une solution aqueuse ; et éventuellement au moins un modificateur et/ou un diluant. Sont en outre divulgués des procédés d'extraction d'un ou plusieurs métaux d'une solution aqueuse, consistant à mettre en contact la solution aqueuse avec une composition de réactif telle que décrite ci-dessus ; et à extraire le ou les métaux, composés de ceux-ci, sels de ceux-ci ou combinaisons de ceux-ci, de la solution aqueuse dans la composition de réactif jusqu'à atteindre l'équilibre pour former une phase aqueuse appauvrie en métal et une phase organique riche en métal.
PCT/US2024/057479 2024-03-20 2024-11-26 Compositions, systèmes et procédés d'extraction d'un ou plusieurs métaux d'une solution Pending WO2025198666A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3306712A (en) * 1963-12-30 1967-02-28 Dow Chemical Co Extraction of lithium halides from calcium-containing brines in the presence of urea and alcohol-ketone
US8454816B1 (en) * 2009-09-11 2013-06-04 Simbol Inc. Selective recovery of manganese and zinc from geothermal brines
US20210324495A1 (en) * 2018-07-10 2021-10-21 Basf Se Process for the recycling of spent lithium ion cells

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3306712A (en) * 1963-12-30 1967-02-28 Dow Chemical Co Extraction of lithium halides from calcium-containing brines in the presence of urea and alcohol-ketone
US8454816B1 (en) * 2009-09-11 2013-06-04 Simbol Inc. Selective recovery of manganese and zinc from geothermal brines
US20210324495A1 (en) * 2018-07-10 2021-10-21 Basf Se Process for the recycling of spent lithium ion cells

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