Tetrabutylammonium perchlorate
[CAS# 1923-70-2]

Identification

• Classification: Surfactant >> Cationic surfactant >> Quaternary ammonium salt type
• Name: Tetrabutylammonium perchlorate
• Molecular Formula: C₁₆H₃₆N.ClO₄
• Molecular Weight: 341.92
• CAS Registry Number: 1923-70-2
• EC Number: 217-655-5
• SMILES: CCCC[N+](CCCC)(CCCC)CCCC.[O-]Cl(=O)(=O)=O

Properties

• Solubility: soluble (ethanol), very slightly soluble (water) (Expl/)
• Melting point: 210-217 °C (Expl.)

Safety Data

• Hazard Symbols: GHS03;GHS07 Danger
• Risk Statements: H272-H315-H319-H335
• Safety Statements: P210-P220-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Oxidising solids	Ox. Sol.	2	H272
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - single exposure	STOT SE	3	H336

• Transport Information: UN 1479

Discovery and Applications

Tetrabutylammonium perchlorate (C16H36NClO4) is a quaternary ammonium salt composed of a tetrabutylammonium cation (C4H9)4N+ and a perchlorate anion (ClO4−). It is typically synthesized by reacting tetrabutylammonium hydroxide with perchloric acid or sodium perchlorate. The resulting compound is a white crystalline solid that is soluble in polar solvents like water, methanol, and acetonitrile.

Tetrabutylammonium perchlorate is primarily utilized in research and industrial applications as a phase-transfer catalyst. In organic chemistry, phase-transfer catalysts facilitate the transfer of reactants between immiscible phases, such as an aqueous and an organic phase. By aiding in the transfer of anions, such as halides or perchlorates, from the aqueous to the organic phase, it significantly enhances reaction rates, especially in nucleophilic substitution reactions.

The compound has also been used in electrochemical applications, particularly in the development of ionic liquids and electrolytes for electrochemical cells. Due to its high ionic conductivity and stability, tetrabutylammonium perchlorate has found use in the design of lithium-ion and other types of batteries, where it can improve the efficiency of energy storage and conversion processes.

Additionally, tetrabutylammonium perchlorate is employed in the preparation of other specialized chemicals and reagents. It is commonly used in the synthesis of perchlorate salts of various organic cations, which can be used in a wide range of chemical reactions. Its role as a reagent in organic synthesis has been documented in various studies, where it serves as a source of perchlorate ions in reactions that require these anions.

In conclusion, tetrabutylammonium perchlorate is a versatile chemical compound with applications in organic synthesis, phase-transfer catalysis, and electrochemical systems. Its ability to facilitate reactions involving immiscible phases and its role in enhancing the ionic conductivity of electrolytes make it valuable in both research and industrial processes.

References

2024. Investigation of the Combination of Indoline and Naphthalimide in the Preparation of Photosensitizers for Photovoltaic Devices. Journal of Electronic Materials, 53(11).
DOI: 10.1007/s11664-024-11538-3

2024. Electrochemical Conversion of Triclosan as a Greener Alternative to Chemical Oxidation. Electrocatalysis, 15(5).
DOI: 10.1007/s12678-024-00892-9

2010. A photo- and electrochemically-active porphyrin-fullerene dyad electropolymer. Photochemical & Photobiological Sciences, 9(6).
DOI: 10.1039/c0pp00013b