Amidoxime-functionalized materials and their use in extracting metal ions from liquid solutions

Patent metadata

Field	Value
Publication number	US-11247191-B2
Application number	US-202016895609-A
Country	US
Kind code	B2
Filing date	Jun 8, 2020
Priority date	Jun 16, 2016
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

A method of producing a functionalized material that extracts metal ions from solution, the method comprising: (i) providing a precursor material having nitrile groups appended to its surface; and (ii) reacting said nitrile groups with hydroxylamine or a derivative thereof in the presence of a polar aprotic solvent at a temperature of 60-80° C. for at least 1 hour, to convert at least a portion of said nitrile groups to amidoxime and imide dioxime groups, followed by reaction with a base capable of hydrolyzing any remaining nitrile groups to carboxylic acid groups; wherein said functionalized material has a higher uranium absorption capacity than a functionalized material produced under same conditions except that the nitrile groups are reacted with hydroxylamine in only a protic solvent. The invention is also directed to functionalized materials produced by the above-described method, and methods for using the functionalized material for extracting metal ions from metal-containing solutions.

First claim

What is claimed is:

1. A method for extracting metal ions from a liquid solution containing metal ions, the method comprising contacting said liquid solution with a functionalized material useful in absorbing metal ions from aqueous solutions, the functionalized material produced by a method comprising:
(i) providing a precursor material having nitrile groups appended to its surface, wherein said precursor material is produced by graft co-polymerization of a nitrile-containing vinylic monomer and itaconic acid, thereby producing a precursor material having nitrile groups and carboxylic acid groups derived from itaconic acid on the surface of the precursor material; and
(ii) reacting said nitrile groups with hydroxylamine or a derivative thereof in the presence of a polar aprotic solvent having a boiling point of at least 100° C., at a temperature of 60-80° C. for at least 1 hour, to convert at least a portion of said nitrile groups to amidoxime and imide dioxime groups, followed by reaction with a base to hydrolyze any remaining nitrile groups to carboxylic acid groups;
wherein said functionalized material has a higher uranium absorption capacity than a functionalized material produced under same conditions except that the nitrile groups are reacted with hydroxylamine or a derivative thereof in only a protic solvent.

2. The method of claim 1 , wherein said imide dioxime groups are present in higher concentration as compared to a functionalized material produced by reacting said nitrile groups under the conditions provided in step (ii) of claim 1 except that a temperature of less than 60° C. is used.

3. The method of claim 1 , wherein said metal ions are selected from at least one of transition, lanthanide, and actinide metal ions.

4. The method of claim 3 , wherein said metal ions comprise uranium ions.

5. The method of claim 1 , wherein said liquid solution is seawater.

6. The method of claim 1 , wherein said precursor material has a fibrous shape, thereby producing a functionalized fiber useful in the absorption of metal ions from aqueous solutions.

Assignees

• Ut Battelle Llc

Inventors

• Janke Christopher J
• Mayes Richard T
• Das Sadananda
• Dai Sheng

Classifications

• D06M14/28

  of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• D06M14/10

  of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• D06M10/008

  Treatment with radioactive elements or with neutrons, alpha, beta or gamma rays · CPC title

• B01J20/321

  consisting of a polymer obtained by reactions involving only carbon to carbon unsaturated bonds · CPC title

• B01J20/265 Primary

  modified or post-treated polymers (polymer carriers or substrates subjected to further impregnating or coating B01J20/3208) · CPC title