Diglycolamide derivatives for separation and recovery of rare earth elements from aqueous solutions

Patent metadata

Field	Value
Publication number	US-12398444-B2
Application number	US-202117366172-A
Country	US
Kind code	B2
Filing date	Jul 2, 2021
Priority date	Jul 6, 2020
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

Rare earth extractant compounds having the following structure:

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from alkyl groups containing 1-30 carbon atoms and optionally containing an ether or thioether linkage connecting between carbon atoms, provided that the total carbon atoms in R 1 , R 2 , R 3 , and R 4 is at least 12; R 5 and R 6 are independently selected from hydrogen atom and alkyl groups containing 1-3 carbon atoms; and provided that at least one of the conditions (i)-(iv) apply as follows: presence of a distal branched group in at least one of R 1 -R 4 (condition i), asymmetry in R 1 -R 4 (condition ii), presence of amine-containing ring (condition iii), or presence of lactam ring (condition iv). Also described are hydrophobic water-insoluble solutions containing at least one extractant compound of Formula (1), as well as method for extracting rare earth elements from aqueous solution by contacting the aqueous solution with the water-insoluble solution.

First claim

What is claimed is:

1. A rare earth extractant compound having the following structure:

wherein:
R 1 , R 2 , R 3 , and R 4 are independently selected from alkyl groups containing 1-30 carbon atoms and optionally containing an ether or thioether linkage connecting between carbon atoms, provided that the total carbon atoms in R 1 , R 2 , R 3 , and R 4 is at least 12; and R 5 and R 6 are independently selected from hydrogen atom and alkyl groups containing 1-3 carbon atoms; and provided that the following condition applies:
at least one of R 1 , R 2 , R 3 , and R 4 is a distal branched alkyl group constructed of a linear alkyl backbone having at least four carbon atoms with an alpha carbon atom of the linear alkyl backbone attached to a nitrogen atom shown in Formula (1), and the linear alkyl backbone contains a substituting hydrocarbon group at a gamma carbon or higher positioned carbon on the linear alkyl backbone, wherein the substituting hydrocarbon group contains at least two carbon atoms, provided that the distal branched alkyl group contains a total of up to 30 carbon atoms.

2. The compound of claim 1 , wherein the distal branched alkyl group contains at least one substituting hydrocarbon group located at a gamma carbon of the linear alkyl backbone.

3. The compound of claim 1 , wherein the distal branched alkyl group contains at least one substituting hydrocarbon group located at a delta carbon of the linear alkyl backbone.

4. The compound of claim 1 , wherein the distal branched alkyl group contains at least one substituting hydrocarbon group located at an epsilon carbon of the linear alkyl backbone.

5. The compound of claim 1 , wherein the distal branched alkyl group contains at least two substituting hydrocarbon groups located at gamma or higher carbon positions of the linear alkyl backbone.

6. A liquid solution useful for extracting rare earth elements from aqueous solutions, the solution comprising a rare earth extractant compound dissolved in an aqueous-insoluble hydrophobic solvent, wherein the rare earth extractant compound has the following structure:

wherein:
R 1 , R 2 , R 3 , and R 4 are independently selected from alkyl groups containing 1-30 carbon atoms and optionally containing an ether or thioether linkage connecting between carbon atoms, provided that the total carbon atoms in R 1 , R 2 , R 3 , and R 4 is at least 12; and R 5 and R 6 are independently selected from hydrogen atom and alkyl groups containing 1-3 carbon atoms; and provided that of the following condition applies:
at least one of R 1 , R 2 , R 3 , and R 4 is a distal branched alkyl group constructed of a linear alkyl backbone having at least four carbon atoms with an alpha carbon atom of the linear alkyl backbone attached to a nitrogen atom shown in Formula (1), and the linear alkyl backbone contains a substituting hydrocarbon group at a gamma carbon or higher positioned carbon on the linear alkyl backbone, wherein the substituting hydrocarbon group contains at least two carbon atoms, provided that the distal branched alkyl group contains a total of up to 30 carbon atoms.

7. The liquid solution of claim 6 , wherein the aqueous-insoluble hydrophobic solvent is a hydrocarbon solvent.

8. The liquid solution of claim 6 , wherein the liquid solution further comprises an organoamine soluble in the aqueous-insoluble hydrophobic solvent.

9. The liquid solution of claim 8 , wherein the organoamine contains at least one hydrocarbon group containing at least four carbon atoms.

10. The liquid solution of claim 6 , wherein the liquid solution further comprises an alcohol soluble in the aqueous-insoluble hydrophobic solvent, and wherein the alcohol contains at least six carbon atoms.

11. The compound of claim 1 , wherein the substituting hydrocarbon group contains at least three carbon atoms, provided that the distal branched alkyl group contains a total of up to 30 carbon atoms.

12. The compound of claim 1 , wherein the substituting hydrocarbon group contains at least four carbon atoms, provided that the distal branched alkyl group contains a total of up to 30 carbon atoms.

13. The compound of claim 1 , wherein the rare earth extractant compound has the following structure:

Assignees

• Ut Battelle Llc

Inventors

• Jansone-Popova Santa
• Popovs Ilja
• Moyer Bruce A

Classifications

• C07D211/42

  attached in position 3 or 5 · CPC title

• C07D207/12

  Oxygen or sulfur atoms · CPC title

• C07D207/08 Primary

  with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms · CPC title

• C07C235/06

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• B01D11/0492

  Applications, solvents used · CPC title