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

Patent metadata

Field	Value
Publication number	US-10702852-B2
Application number	US-201715625276-A
Country	US
Kind code	B2
Filing date	Jun 16, 2017
Priority date	Jun 16, 2016
Publication date	Jul 7, 2020
Grant date	Jul 7, 2020

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 of producing a functionalized material useful in absorbing metal ions from aqueous solutions, the 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 step (ii) is conducted at a temperature of 60-80° C. for 1-24 hours.

3. The method of claim 1 , wherein step (ii) is conducted at a temperature of 65-80° C. for 1-24 hours.

4. The method of claim 1 , wherein step (ii) is conducted at a temperature of 70-80° C. for 1-24 hours.

5. The method of claim 1 , wherein step (ii) is conducted at a temperature of 60-80° C. for 1-6 hours.

6. The method of claim 1 , wherein step (ii) is conducted at a temperature of 65-80° C. for 1-6 hours.

7. The method of claim 1 , wherein step (ii) is conducted at a temperature of 70-80° C. for 1-6 hours.

8. The method of claim 1 , wherein said polar aprotic solvent is a sulfoxide solvent.

9. The method of claim 1 , wherein said polar aprotic solvent is an amide solvent.

10. The method of claim 1 , wherein said substrate has a polyolefin composition.

11. The method of claim 1 , wherein said graft polymerization is a radiation-induced graft polymerization.

12. 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.

13. The method of claim 1 , wherein said precursor material has a fiber 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

• D06M14/10

  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

• D01D5/247

  Discontinuous hollow structure or microporous structure · CPC title

• D06M11/38

  Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table · CPC title

• D06M13/368

  Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases · CPC title