Sodium Trifluoromethanesulfonate 2926-30-9 CF₃SO₃Na

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  Sodium triflate Uses  

Sodium trifluoromethanesulfonate (Sodium triflate) is an organic sodium salt with the trifluoromethanesulfonate (TfO⁻) anion. It shares many of the properties of other triflate salts, such as high solubility in organic solvents, thermal stability, and the ability to act as a source of the trifluoromethanesulfonate group, which has valuable applications in various chemical reactions and materials science. Below are some of its key uses:

1. Electrolytes in Energy Storage
   Lithium-ion and Lithium-Sulfur Batteries: Sodium trifluoromethanesulfonate can be used in the formulation of electrolytes for lithium-ion batteries or lithium-sulfur batteries. Its high solubility and electrochemical stability make it an effective salt to improve ionic conductivity, enhance battery efficiency, and increase the stability of the electrolyte in high-performance energy storage devices.
    Supercapacitors: It can also be used as a salt in electrolytes for supercapacitors, where its properties help in improving the charge/discharge cycles and conductivity of the device.

2. Fluorination Reactions
   Fluorination Agent: The trifluoromethanesulfonate (TfO) group can be used in fluorination reactions, where it serves as a trifluoromethylating agent. This means it can introduce a trifluoromethyl group (-CF₃) into organic molecules. Trifluoromethyl groups are highly valued in pharmaceuticals, agrochemicals, and materials science due to their ability to modify the physical and chemical properties of compounds, such as increasing metabolic stability or bioactivity.
    Formation of Triflate Esters: Sodium triflate is used to form triflate esters from alcohols. Triflate esters are highly reactive and can be further utilized in nucleophilic substitution reactions, cross-coupling reactions, and other organic transformations.

3. Catalyst in Organic Synthesis
    Lewis Acid Catalysis: Sodium trifluoromethanesulfonate can serve as a mild Lewis acid catalyst in various organic reactions, including Friedel–Crafts alkylation, acylation, and other electrophilic aromatic substitution reactions. The highly electrophilic nature of the TfO⁻ anion enhances the reactivity of many organic substrates, promoting these transformations.
    Activation of Carbonyl Compounds: It can activate carbonyl compounds for further reactions, such as in esterification, dehydration, or condensation reactions.
    Nucleophilic Substitution: As a source of the triflate group, it can facilitate nucleophilic substitution reactions, such as in the synthesis of aryl triflates or alkyl triflates.

4. Fluorinated Organics Synthesis
    Pharmaceuticals and Agrochemicals: The trifluoromethanesulfonate group is often introduced into molecules to modify their chemical reactivity, solubility, or metabolic stability. As a result, sodium trifluoromethanesulfonate is valuable in the synthesis of fluorinated pharmaceuticals and agrochemicals. The trifluoromethyl group can enhance properties such as lipophilicity, bioavailability, and resistance to metabolic degradation.
    Specialty Materials: Sodium trifluoromethanesulfonate can also be used in the production of fluorinated polymers and other specialty materials that require the unique properties imparted by the trifluoromethyl group.

5. Polymerization Initiation and Catalysis
   Catalyst for Polymerization: It can be used as a catalyst or co-catalyst in the polymerization of vinyl monomers or in ring-opening polymerization (ROP) reactions. The triflate anion, combined with the sodium cation, can act as a coordination site for monomers, helping to initiate or propagate polymer chains.
    Polymerization of Fluorinated Monomers: Sodium triflate is particularly useful for polymerizing fluorinated monomers, which are important for the synthesis of high-performance polymers with properties such as high thermal stability, chemical resistance, and low friction.

6. Electrochemical Applications
   Electrolyte in Superionic Conductors: Sodium trifluoromethanesulfonate is used in the preparation of superionic conductors, which are materials that exhibit high ionic conductivity at relatively low temperatures. These materials are often used in the development of solid-state batteries and other advanced electrochemical systems.
    Ionic Liquids and Electrochemical Devices: It is sometimes incorporated into ionic liquids, which are used in electrochemical devices like fuel cells and sensors. The high ionic conductivity of Sodium triflate enhances the performance of these devices.

7. Green Chemistry Applications
   Solvent and Reaction Medium: Sodium trifluoromethanesulfonate can be part of green chemistry processes, as it can serve as a non-volatile solvent or a medium for reactions that require environmentally friendly solvents. Its low toxicity and high stability make it an alternative to traditional organic solvents in various industrial applications.

8. Ion Pairing in Solution
   Electrolyte and Ionic Pairing: Sodium triflate can be used in the formulation of electrolytes or in applications requiring ionic pairing, particularly in electrochemical and analytical settings. It is used to form stable ion pairs with metal ions or organic cations in solution, enhancing their solubility and stability.

9. Surface Modification
   Surface Functionalization: In material science, Sodium triflate is used to modify the surfaces of materials, particularly polymers and nanomaterials. The trifluoromethanesulfonate group can alter the surface properties of materials, such as improving their hydrophobicity or enhancing their interaction with other chemical species.

Summary of Key Applications:

• Electrolytes for lithium-ion batteries, supercapacitors, and energy storage devices.

• Fluorination and trifluoromethylation in organic synthesis (e.g., pharmaceuticals, agrochemicals).

• Catalysis in organic reactions, including esterification, Friedel–Crafts reactions, and nucleophilic substitutions.

• Polymerization catalysis, especially for fluorinated monomers and specialty polymers.

• Electrochemical applications in batteries, superionic conductors, and sensors.

• Green chemistry applications as a low-toxicity solvent and reaction medium.

• Ion pairing and surface modification for material applications.

Sodium trifluoromethanesulfonate’s unique properties, such as high stability, solubility, and the ability to impart the trifluoromethanesulfonate group to various substrates, make it valuable across a broad range of chemical and industrial processes.