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

Janke, Christopher J.; Mayes, Richard T.; Das, Sadananda; Dai, Sheng

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

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.

Inventors:: Janke, Christopher J.; Mayes, Richard T.; Das, Sadananda; Dai, Sheng

Issue Date:: 2020-07-07

Research Org.:: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1734993

Patent Number(s):: 10702852

Application Number:: 15/625,276

Assignee:: UT-Battelle, LLC (Oak Ridge, TN)

Patent Classifications (CPCs):: C - CHEMISTRY C02 - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE C02F - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE

D - TEXTILES D06 - TREATMENT OF TEXTILES OR THE LIKE D06M - TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS

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C - CHEMISTRY C02 - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE C02F - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
C02F1/285 - {using synthetic organic sorbents}

D - TEXTILES D06 - TREATMENT OF TEXTILES OR THE LIKE D06M - TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M11/38 - Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic System

D - TEXTILES D01 - NATURAL OR MAN-MADE THREADS OR FIBRES D01F - CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
D01F6/46 - of polyolefins

C - CHEMISTRY C02 - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE C02F - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
C02F2103/08 - Seawater, e.g. for desalination

D - TEXTILES D06 - TREATMENT OF TEXTILES OR THE LIKE D06M - TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M14/28 - of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds

C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08F - MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
C08F255/02 - on to polymers of olefins having two or three carbon atoms

D - TEXTILES D06 - TREATMENT OF TEXTILES OR THE LIKE D06M - TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M13/368 - Hydroxyalkylamines

B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY
B01J20/321 - {consisting of a polymer obtained by reactions involving only carbon to carbon unsaturated bonds}

C - CHEMISTRY C02 - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE C02F - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
C02F2101/006 - {Radioactive compounds}

B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY
B01J20/3085 - {Chemical treatments not covered by groups B01J20/3007 - B01J20/3078}

D - TEXTILES D01 - NATURAL OR MAN-MADE THREADS OR FIBRES D01D - MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
D01D5/247 - Discontinuous hollow structure or microporous structure

D - TEXTILES D06 - TREATMENT OF TEXTILES OR THE LIKE D06M - TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M14/10 - of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds

B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY
B01J20/265 - {modified or post-treated polymers
B01J20/3265 - {with an organic functional group containing a metal, e.g. a metal affinity ligand}
B01J20/3217 - {Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond}

C - CHEMISTRY C02 - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE C02F - TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
C02F2101/20 - Heavy metals or heavy metal compounds

D - TEXTILES D06 - TREATMENT OF TEXTILES OR THE LIKE D06M - TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
D06M10/008 - {Treatment with radioactive elements or with neutrons, alpha, beta or gamma rays}

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DOE Contract Number:: AC05-00OR22725

Resource Type:: Patent

Resource Relation:: Patent File Date: 06/16/2017

Country of Publication:: United States

Language:: English

Citation Formats


                    Janke, Christopher J., Mayes, Richard T., Das, Sadananda, and Dai, Sheng. Amidoxime-functionalized materials and their use in extracting metal ions from liquid solutions.  United States: N. p., 2020. 
        Web.

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                    Janke, Christopher J., Mayes, Richard T., Das, Sadananda, & Dai, Sheng. Amidoxime-functionalized materials and their use in extracting metal ions from liquid solutions.  United States.

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                    Janke, Christopher J., Mayes, Richard T., Das, Sadananda, and Dai, Sheng. Tue .  
        "Amidoxime-functionalized materials and their use in extracting metal ions from liquid solutions".  United States.  https://www.osti.gov/servlets/purl/1734993.

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@article{osti_1734993,

  title        = {Amidoxime-functionalized materials and their use in extracting metal ions from liquid solutions},

  author       = {Janke, Christopher J. and Mayes, Richard T. and Das, Sadananda and Dai, Sheng},

  abstractNote = {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.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2020},

  month        = {7}

}

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Works referenced in this record:

Uranium adsorbing material and process for preparing the same
patent, November 1986

Sugo, Takanobu; Okamoto, Jiro; Ishigaki, Isao
US Patent Document 4,622,366
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=4622366

Carbon/carbon composite materials and use thereof in electrochemical cells
patent, July 1998

Mrotek, Edward N.; Reichman, Benjamin; Yin, MengPing
US Patent Document 5,776,633
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=5776633

Electrode stack for capacitive device
patent, August 2010

Bourcier, Roy Joseph; St Clair, Todd Parrish; Nadjadi, Andrew R.
US Patent Document 7,766,981
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=7766981

Mesoporous carbon materials
patent, February 2012

Dai, Sheng; Wang, Xiqing
US Patent Document 8,114,510
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=8114510

Mesoporous carbons
patent, March 1984

Everett, Douglas H.; Bligh, Stephen G.; Rojas, Fernando
US Patent Document 4,439,349
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=4439349

Method and apparatus for capacitive deionization and electrochemical purification and regeneration of electrodes
patent, September 1999

Farmer, Joseph C.
US Patent Document 5,954,937
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=5954937

Robust carbon monolith having hierarchical porosity
patent, November 2008

Dai, Sheng; Guiochon, Georges A.; Liang, Chengdu
US Patent Document 7,449,165
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=7449165

Collector of dissolved metal from sea water having an amidoxime group and a hydrophilic group, a method for production thereof
patent, December 2001

Sugo, Takanobu; Katakai, Akio; Seko, Noriaki
US Patent Document 6,333,078
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=6333078

Surface-functionalized mesoporous carbon materials
patent, February 2016

Dai, Sheng; Gorka, Joanna; Mayes, Richard T.
US Patent Document 9,249,241
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=9249241

Fabricating solid carbon porous electrodes from powders
patent, June 1997

Kaschmitter, James L.; Tran, Tri D.; Feikert, John H.
US Patent Document 5,636,437
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=5636437

Method and apparatus for capacitive deionization and electrochemical purification and regeneration of electrodes
patent, October 2001

Tran, Tri D.; Farmer, Joseph C.; Murguia, Laura
US Patent Document 6,309,532
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=6309532

Flow-through capacitor and method
patent, August 2004

Andelman, Marc D.
US Patent Document 6,778,378
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=6778378

Method for making thin carbon foam electrodes
patent, August 1999

Pekala, Richard W.; Mayer, Steven T.; Kaschmitter, James L.
US Patent Document 5,932,185
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=5932185

Supercapacitor and electrochemical apparatus for water purification
patent, November 2010

Kang, Hyo-rang; Yang, Hojung
US Patent Document 7,835,137
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=7835137

Acid-functionalized polyolefin materials and their use in acid-promoted chemical reactions
patent, June 2016

Oyola, Yatsandra; Tian, Chengcheng; Bauer, John Christopher
US Patent Document 9,359,320
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=9359320

Ion-removal from water using activated carbon electrodes
patent, April 2001

Gadkaree, Kishor Purushottam; Mach, Joseph F.; Stempin, John L.
US Patent Document 6,214,204
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=6214204

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Similar Records

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

Abstract

Citation Formats

Uranium adsorbing material and process for preparing the same patent, November 1986

Carbon/carbon composite materials and use thereof in electrochemical cells patent, July 1998

Electrode stack for capacitive device patent, August 2010

Mesoporous carbon materials patent, February 2012

Mesoporous carbons patent, March 1984

Method and apparatus for capacitive deionization and electrochemical purification and regeneration of electrodes patent, September 1999

Robust carbon monolith having hierarchical porosity patent, November 2008

Collector of dissolved metal from sea water having an amidoxime group and a hydrophilic group, a method for production thereof patent, December 2001

Surface-functionalized mesoporous carbon materials patent, February 2016

Fabricating solid carbon porous electrodes from powders patent, June 1997

Method and apparatus for capacitive deionization and electrochemical purification and regeneration of electrodes patent, October 2001

Flow-through capacitor and method patent, August 2004

Method for making thin carbon foam electrodes patent, August 1999

Supercapacitor and electrochemical apparatus for water purification patent, November 2010

Acid-functionalized polyolefin materials and their use in acid-promoted chemical reactions patent, June 2016

Ion-removal from water using activated carbon electrodes patent, April 2001

Uranium adsorbing material and process for preparing the same
patent, November 1986

Carbon/carbon composite materials and use thereof in electrochemical cells
patent, July 1998

Electrode stack for capacitive device
patent, August 2010

Mesoporous carbon materials
patent, February 2012

Mesoporous carbons
patent, March 1984

Method and apparatus for capacitive deionization and electrochemical purification and regeneration of electrodes
patent, September 1999

Robust carbon monolith having hierarchical porosity
patent, November 2008

Collector of dissolved metal from sea water having an amidoxime group and a hydrophilic group, a method for production thereof
patent, December 2001

Surface-functionalized mesoporous carbon materials
patent, February 2016

Fabricating solid carbon porous electrodes from powders
patent, June 1997

Method and apparatus for capacitive deionization and electrochemical purification and regeneration of electrodes
patent, October 2001

Flow-through capacitor and method
patent, August 2004

Method for making thin carbon foam electrodes
patent, August 1999

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patent, June 2016

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patent, April 2001