Superbase-derived protic ionic liquids

Dai, Sheng; Luo, Huimin; Baker, Gary A.

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Title: Superbase-derived protic ionic liquids

Abstract

Protic ionic liquids having a composition of formula (A.sup.-)(BH.sup.+) wherein A.sup.- is a conjugate base of an acid HA, and BH.sup.+ is a conjugate acid of a superbase B. In particular embodiments, BH.sup.+ is selected from phosphazenium species and guanidinium species encompassed, respectively, by the general formulas: ##STR00001## The invention is also directed to films and membranes containing these protic ionic liquids, with particular application as proton exchange membranes for fuel cells.

Inventors:: Dai, Sheng; Luo, Huimin; Baker, Gary A.

Issue Date:: Tue Sep 03 00:00:00 EDT 2013

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

Sponsoring Org.:: USDOE

OSTI Identifier:: 1092764

Patent Number(s):: 8524388

Application Number:: 12/690,224

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

Patent Classifications (CPCs):: C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08J - WORKING-UP

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01B - CABLES

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C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08J - WORKING-UP
C08J2379/08 - Polyimides
C08J5/2256 - {based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation}

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01B - CABLES
H01B1/122 - {Ionic conductors}

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01M - PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
H01M2300/0045 - Room temperature molten salts comprising at least one organic ion
H01M8/0289 - Means for holding the electrolyte
H01M8/0295 - Matrices for immobilising electrolyte melts

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02E - REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
Y02E60/50 - Fuel cells

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DOE Contract Number:: AC05-00OR22725

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Dai, Sheng, Luo, Huimin, and Baker, Gary A. Superbase-derived protic ionic liquids.  United States: N. p., 2013. 
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                    Dai, Sheng, Luo, Huimin, & Baker, Gary A. Superbase-derived protic ionic liquids.  United States.

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                    Dai, Sheng, Luo, Huimin, and Baker, Gary A. Tue .  
        "Superbase-derived protic ionic liquids".  United States.  https://www.osti.gov/servlets/purl/1092764.

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@article{osti_1092764,

  title        = {Superbase-derived protic ionic liquids},

  author       = {Dai, Sheng and Luo, Huimin and Baker, Gary A.},

  abstractNote = {Protic ionic liquids having a composition of formula (A.sup.-)(BH.sup.+) wherein A.sup.- is a conjugate base of an acid HA, and BH.sup.+ is a conjugate acid of a superbase B. In particular embodiments, BH.sup.+ is selected from phosphazenium species and guanidinium species encompassed, respectively, by the general formulas: ##STR00001## The invention is also directed to films and membranes containing these protic ionic liquids, with particular application as proton exchange membranes for fuel cells.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue Sep 03 00:00:00 EDT 2013},

  month        = {Tue Sep 03 00:00:00 EDT 2013}

}

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Works referenced in this record:

Physical Properties of Ionic Liquids Consisting of the 1-Butyl-3-Methylimidazolium Cation with Various Anions and the Bis(trifluoromethylsulfonyl)imide Anion with Various Cations
journal, January 2008

Jin, Hui; O'Hare, Bernie; Dong, Jing
The Journal of Physical Chemistry B, Vol. 112, Issue 1
https://doi.org/10.1021/jp076462h

New Types of Brönsted Acid–Base Ionic Liquids-Based Membranes for Applications in PEMFCs
journal, May 2007

Fernicola, Alessandra; Panero, Stefania; Scrosati, Bruno
ChemPhysChem, Vol. 8, Issue 7
https://doi.org/10.1002/cphc.200600782

Brønsted acid–base ionic liquids for fuel cell electrolytes
journal, January 2007

Nakamoto, Hirofumi; Watanabe, Masayoshi
Chem. Commun., Issue 24
https://doi.org/10.1039/B618953A

The distillation and volatility of ionic liquids
journal, February 2006

Earle, Martyn J.; Esperança, José M. S. S.; Gilea, Manuela A.
Nature, Vol. 439, Issue 7078
https://doi.org/10.1038/nature04451

Brønsted acid–base ionic liquids and their use as new materials for anhydrous proton conductors
journal, January 2003

Susan, Md. A. B. H.; Noda, Akihiro; Mitsushima, Shigenori
Chemical Communications, Issue 8
https://doi.org/10.1039/b300959a

A New Strategy for Synthesis of Novel Classes of Room-Temperature Ionic Liquids Based on Complexation Reaction of Cations
journal, January 2006

Huang, Jing-Fang; Luo, Huimin; Dai, Sheng
Journal of The Electrochemical Society, Vol. 153, Issue 2
https://doi.org/10.1149/1.2150161

Polarity Measurement for Ionic Liquids Containing Dissociable Protons
journal, November 2004

Ogihara, Wataru; Aoyama, Takahiro; Ohno, Hiroyuki
Chemistry Letters, Vol. 33, Issue 11
https://doi.org/10.1246/cl.2004.1414

Ultrastable Superbase-Derived Protic Ionic Liquids
journal, February 2009

Luo, Huimin; Baker, Gary A.; Lee, Je Seung
The Journal of Physical Chemistry B, Vol. 113, Issue 13
https://doi.org/10.1021/jp901312d

Protic Ionic Liquids: Preparation, Characterization, and Proton Free Energy Level Representation ^†
journal, May 2007

Belieres, Jean-Philippe; Angell, C. Austen
The Journal of Physical Chemistry B, Vol. 111, Issue 18
https://doi.org/10.1021/jp067589u

Binary inorganic salt mixtures as high conductivity liquid electrolytes for >100 °C fuel cells
journal, January 2006

Belieres, Jean-Philippe; Gervasio, Don; Angell, C. Austen
Chem. Commun., Issue 46
https://doi.org/10.1039/B611150E

Guanidinophosphazenes: Design, Synthesis, and Basicity in THF and in the Gas Phase
journal, November 2005

Kolomeitsev, Alexander A.; Koppel, Ilmar A.; Rodima, Toomas
Journal of the American Chemical Society, Vol. 127, Issue 50
https://doi.org/10.1021/ja053543n

Protic Ionic Liquids: Properties and Applications
journal, January 2008

Greaves, Tamar L.; Drummond, Calum J.
Chemical Reviews, Vol. 108, Issue 1, p. 206-237
https://doi.org/10.1021/cr068040u

Similar Records in DOE Patents and OSTI.GOV collections:

Ultrastable Superbase-Derived Protic Ionic Liquids

Journal Article Luo, Huimin; Baker, Gary A.; Lee, Je Seung; ... - Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry

Protic ionic liquids are synthesized via proton transfer from acids to organic bases. One of the key issues associated with conventional protic ionic liquids is the thermal instability resulting from temperature-induced decomposition via reverse proton transfer. This shortcoming significantly hampers the use of these protic ionic liquids in separations, electrochemical capacitors, fuel cells, and so forth. Herein we show that it is possible to prepare protic ionic liquids with thermal stabilities approaching those of common aprotic ionic liquids. Our new class of protic ionic liquids, derived via integrated neutralization and metathesis of superbasic phosphazenes or guanidines, exhibits exceptionally low vapormore » « less
DOI: https://doi.org/10.1021/jp901312d
Carbon Dioxide Capture by Superbase-Derived Protic Ionic Liquids

Journal Article Wang, Congmin [ORNL]; Luo, Huimin [ORNL]; Dai, Sheng [ORNL]; ... - Angewandte Chemie International Edition

Protic ionic liquids (PILs) from a superbase and fluorinated alcohol, imidazole, pyrrolinone, or phenol were designed to capture CO{sub 2} based on the reactivity of their anions to CO{sub 2}. These PILs are capable of rapid and reversible capture of about one equivalent of CO{sub 2}, which is superior to those sorption systems based on traditional aprotic ILs.
DOI: https://doi.org/10.1002/anie.201002641
Carbon Dioxide Capture by Superbase-Derived Protic Ionic Liquids

Journal Article Dai, Sheng [ORNL]; Luo, Huimin [ORNL]; Li, Haoran [Zhejiang University]; ... - ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Protic ionic liquids (PILs) from a superbase and fluorinated alcohol, imidazole, pyrrolinone, or phenol were designed to capture CO{sub 2} based on the reactivity of their anions to CO{sub 2}. These PILs are capable of rapid and reversible capture of about one equivalent of CO{sub 2}, which is superior to those sorption systems based on traditional aprotic ILs.
Superbase-derived protic ionic liquids with chelating fluorinated anions

Journal Article Bell, Jason R [ORNL]; Luo, Huimin [ORNL]; Dai, Sheng [ORNL] - Tetrahedron Letters

Eighteen new protic ionic liquids were synthesized in one step from five organic superbases and five commercially available fluorinated -diketones. Physical properties of the ionic liquids, including thermal decomposition temperature were determined. Nine of the ionic liquids were examined as extraction media for La3+, with some very large distribution coefficients obtained.
DOI: https://doi.org/10.1016/j.tetlet.2011.05.037
Superbase-derived protic ionic liquid extractants for metal ion separation

Journal Article Bell, Jason R. [Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Energy and Transportation Science Div.]; Dai, Sheng [Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Energy and Transportation Science Div.]; Luo, Huimin [Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Div.] - Separation and Purification Technology

Solvent extraction of La³⁺ and Ba²⁺ by an ionic liquid extractant in an imidazolium-based ionic liquid diluent was investigated. Seven protic ionic liquid extractants were examined and these protic ILs are based on five organic superbases and either 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadione (Hfod) or 1,1,1,5,5,5-hexafluoroacetylacetone (Hhfac) -diketones as anion. For fod-based extractants, the extraction efficiencies and separation factors were found to be concentration dependent. The effects of aqueous phase acidity, extractant structure, and extractant concentration on separation properties of La³⁺ and Ba²⁺ are discussed in this paper.
Cited by 17
DOI: https://doi.org/10.1016/j.seppur.2014.04.023

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Title: Superbase-derived protic ionic liquids

Abstract

Citation Formats

Physical Properties of Ionic Liquids Consisting of the 1-Butyl-3-Methylimidazolium Cation with Various Anions and the Bis(trifluoromethylsulfonyl)imide Anion with Various Cations journal, January 2008

New Types of Brönsted Acid–Base Ionic Liquids-Based Membranes for Applications in PEMFCs journal, May 2007

Brønsted acid–base ionic liquids for fuel cell electrolytes journal, January 2007

The distillation and volatility of ionic liquids journal, February 2006

Brønsted acid–base ionic liquids and their use as new materials for anhydrous proton conductors journal, January 2003

A New Strategy for Synthesis of Novel Classes of Room-Temperature Ionic Liquids Based on Complexation Reaction of Cations journal, January 2006

Polarity Measurement for Ionic Liquids Containing Dissociable Protons journal, November 2004

Ultrastable Superbase-Derived Protic Ionic Liquids journal, February 2009

Protic Ionic Liquids: Preparation, Characterization, and Proton Free Energy Level Representation † journal, May 2007

Binary inorganic salt mixtures as high conductivity liquid electrolytes for >100 °C fuel cells journal, January 2006

Guanidinophosphazenes: Design, Synthesis, and Basicity in THF and in the Gas Phase journal, November 2005

Protic Ionic Liquids: Properties and Applications journal, January 2008

Physical Properties of Ionic Liquids Consisting of the 1-Butyl-3-Methylimidazolium Cation with Various Anions and the Bis(trifluoromethylsulfonyl)imide Anion with Various Cations
journal, January 2008

New Types of Brönsted Acid–Base Ionic Liquids-Based Membranes for Applications in PEMFCs
journal, May 2007

Brønsted acid–base ionic liquids for fuel cell electrolytes
journal, January 2007

The distillation and volatility of ionic liquids
journal, February 2006

Brønsted acid–base ionic liquids and their use as new materials for anhydrous proton conductors
journal, January 2003

A New Strategy for Synthesis of Novel Classes of Room-Temperature Ionic Liquids Based on Complexation Reaction of Cations
journal, January 2006

Polarity Measurement for Ionic Liquids Containing Dissociable Protons
journal, November 2004

Ultrastable Superbase-Derived Protic Ionic Liquids
journal, February 2009

Protic Ionic Liquids: Preparation, Characterization, and Proton Free Energy Level Representation ^†
journal, May 2007

Binary inorganic salt mixtures as high conductivity liquid electrolytes for >100 °C fuel cells
journal, January 2006

Guanidinophosphazenes: Design, Synthesis, and Basicity in THF and in the Gas Phase
journal, November 2005

Protic Ionic Liquids: Properties and Applications
journal, January 2008