1-Butyl-1-methylpyrrolidinium hexafluorophosphate
[CAS# 330671-29-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ionic liquid
• Name: 1-Butyl-1-methylpyrrolidinium hexafluorophosphate
• Molecular Formula: C₉H₂₀F₆NP
• Molecular Weight: 287.23
• CAS Registry Number: 330671-29-9
• EC Number: 627-513-8
• SMILES: CCCC[N+]1(CCCC1)C.F[P-](F)(F)(F)(F)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

1-Butyl-1-methylpyrrolidino hexafluorophosphate (BMPLPF₆) is an ionic liquid that has attracted a lot of attention in recent years due to its unique properties and wide range of applications. This compound belongs to the family of ionic liquids, which are known for their excellent thermal stability, low volatility, and ability to dissolve a wide range of substances. The concept of ionic liquids dates back to the early 20th century, but the widespread interest and development in them surged in the late 20th and early 21st centuries. BMPLPF₆, like many other ionic liquids, was discovered in the ongoing research to find alternatives to traditional organic solvents. Researchers aimed to develop environmentally friendly and efficient solvents for various industrial and laboratory processes. The systematic exploration of pyrrolidine-based ionic liquids led to the synthesis and characterization of 1-butyl-1-methylpyrrolidino hexafluorophosphate.

The synthesis of BMPLPF₆ generally involves two steps: first, quaternization, where 1-methylpyrrolidine reacts with butyl bromide to form 1-butyl-1-methylpyrrolidine bromide (BMPLBr), followed by an anion exchange reaction of BMPLBr with potassium hexafluorophosphate (KPF₆) to replace the bromide ion with the hexafluorophosphate ion to give BMPLPF₆. The resulting ionic liquid is purified to remove any impurities or residual reactants, resulting in high-purity BMPLPF₆.

BMPLPF₆ is widely used as an electrolyte in electrochemistry. Its ionic nature and high ionic conductivity make it an excellent choice for a variety of electrochemical applications, including batteries, capacitors, and electrochemical sensors. Its stability and low volatility are particularly beneficial for high-temperature and long-term applications.

The unique solvation properties of BMPLPF₆ make it an ideal solvent for a variety of organic reactions. It has been used in a variety of catalytic processes, such as hydrogenation, oxidation, and alkylation reactions. Its ability to dissolve polar and nonpolar compounds improves reaction rates and selectivity, making it a valuable tool for synthetic chemists.

As an environmentally friendly alternative to traditional organic solvents, BMPLPF₆ plays a vital role in green chemistry. Its low volatility and nonflammability reduce the risk of environmental contamination and improve safety in laboratory and industrial settings. Researchers are continually exploring new ways to utilize BMPLPF₆ in sustainable chemical processes, including biomass conversion and carbon capture.

In materials science, BMPLPF₆ is used in the preparation and processing of advanced materials. It serves as a medium for the synthesis of nanoparticles, conductive polymers, and other functional materials. Its ionic nature and ability to stabilize charged species are particularly beneficial for the development of new materials with unique properties.

BMPLPF₆ is also used in a variety of analytical techniques. It is used as a mobile phase modifier in liquid chromatography to improve the separation of complex mixtures. Its high solubility for a wide range of analytes improves detection sensitivity and resolution in analytical applications.

References

2024. Ionic liquids in green energy storage devices: lithium-ion batteries, supercapacitors, and solar cells. Monatshefte für Chemie - Chemical Monthly, 155(3).
DOI: 10.1007/s00706-024-03178-4