1,2,3-triazolium ionic liquids
Inventors
Luebke, David • Nulwala, Hunaid • Tang, Chau
Assignees
Publication Number
US-8907105-B1
Publication Date
2014-12-09
Expiration Date
2031-09-01
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Abstract
The present invention relates to compositions of matter that are ionic liquids, the compositions comprising substituted 1,2,3-triazolium cations combined with any anion. Compositions of the invention should be useful in the separation of gases and, perhaps, as catalysts for many reactions.
Core Innovation
The invention relates to compositions of ionic liquids comprising substituted 1,2,3-triazolium cations combined with various anions. These ionic liquids exhibit advantageous properties such as increased carbon dioxide solubility and polymerization capability, which are proposed to provide improved performance over other classes of ionic liquids in applications such as gas separation and potentially as catalysts.
The problem addressed by the invention arises from the vast number of possible ionic liquid compounds (estimated up to 10^18), making the selection of suitable ionic liquids for applications like gas separations challenging. Although certain aromatic heterocyclic ionic liquids have been explored for gas separations, few have been widely used, highlighting the need to develop novel ionic liquids with improved and tunable properties.
The invention solves this problem by providing a novel class of tri-substituted 1,2,3-triazolium ionic liquids synthesized through highly modular and regio-specific click chemistry. The triazolium core allows systematic probing of ionic liquid properties with excellent molecular control, ease of synthesis, and favorable thermal stability arising from increased dipole moments. The compositions include a tri-substituted 1,2,3-triazolium salt structure where substituents R1, R2, and R3 are independently selected from a wide group including hydrogen, halogens, alkanes, alkenes, and substituted aryl or heteroaryl groups, paired with any suitable anion.
Claims Coverage
The patent claims cover several inventive features focused on the composition and use of tri-substituted 1,2,3-triazolium ionic liquids with various substituents and anions.
Ionic liquid composition comprising tri-substituted 1,2,3-triazolium cations
An ionic liquid composition comprising a tri-substituted 1,2,3-triazolium core where substituents R1, R2, and R3 are independently selected from groups including hydrogen, halogen, alkane/alkene chains (C1-C25), heteroatom-containing chains, unsubstituted or substituted aryl and heteroaryl groups with specific substituents, paired with an anion X−.
Composition with alkane substituent at R2 and specific anions
The tri-substituted ionic liquid where R2 is a C1 to C25 straight-chain or branched alkane, and the anion X− is selected from iodide, bromide, chloride, acetate, and bis[(trifluoromethyl)sulfonyl]amide (Tf2N).
Specific ionic liquid compositions with defined substituents and anions
A selection of ionic liquids explicitly recited comprising specific 1,2,3-triazolium cations with detailed substituents such as vinyl, pyridine, phenyl, benzyl, propyl, hexyl, trimethylsilyl methyl groups, paired with iodide or bis[(trifluoromethyl)sulfonyl]amide anions, representing a set of exemplary compositions of the invention.
The claims collectively cover the novel tri-substituted 1,2,3-triazolium ionic liquid compositions with diverse substituent options and anions, including specific exemplary ionic liquids, establishing the scope of compositions encompassed by the invention.
Stated Advantages
Increased carbon dioxide solubility compared to other classes of ionic liquids.
Improved polymerization capability in some embodiments.
High modularity and regio-specificity of the 1,2,3-triazolium core allowing systematic exploration of functional properties.
Ease of synthesis using click chemistry with excellent molecular control, high yield, stereospecificity, and mild reaction conditions.
Greater dipole moment leading to enhanced thermal stability of the ionic liquids.
Documented Applications
Use of the ionic liquids for the separation or purification of gases, specifically including the separation of carbon dioxide from gaseous mixtures.
Use as supported ionic liquid membranes (SILMs) to selectively solubilize impurities in a gas stream, improving gas separation efficiency.
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