Tetraethylammonium hydroxide
[CAS# 77-98-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Urea
• Name: Tetraethylammonium hydroxide
• Synonyms: TEA hydroxide
• Molecular Formula: C₈H₂₁NO
• Molecular Weight: 147.26
• CAS Registry Number: 77-98-5
• EC Number: 201-073-3
• SMILES: CC[N+](CC)(CC)CC.[OH-]

Properties

• Density: 1.023 g/mL (Expl.)
• Refraction index: 1.373 (Expl.)
• Boiling point: 110 °C
• Flash point: 16 °C (Expl.)
• Water solubility: SOLUBLE

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H290-H302-H311-H314-H318-H370-H372-H410
• Safety Statements: P234-P260-P262-P264-P264+P265-P270-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P308+P316-P316-P317-P319-P321-P330-P361+P364-P363-P390-P391-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Specific target organ toxicity - single exposure	STOT SE	1	H370
Acute toxicity	Acute Tox.	3	H311
Skin corrosion	Skin Corr.	1A	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	2	H300
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

• Transport Information: UN 3267

Discovery and Applications

Tetraethylammonium hydroxide (TEAOH) is a quaternary ammonium hydroxide with the chemical formula (C2H5)4NOH. It consists of a tetraethylammonium cation, where four ethyl groups are attached to a central nitrogen atom, and a hydroxide anion. This compound is typically found as an aqueous solution, where it dissociates into tetraethylammonium ions and hydroxide ions. It is a strong base that is used in various chemical processes and applications.

Tetraethylammonium hydroxide is often synthesized by reacting tetraethylammonium salts, such as tetraethylammonium bromide or tetraethylammonium chloride, with a strong base like sodium hydroxide. The reaction produces Tetraethylammonium hydroxide and the corresponding sodium salt. This compound, like other quaternary ammonium hydroxides, is of interest due to its strong basicity and ability to act as a non-corrosive alternative to other strong bases such as sodium hydroxide or potassium hydroxide.

One of the primary applications of tetraethylammonium hydroxide is in the field of organic synthesis. It serves as a strong, non-corrosive base for reactions like deprotonation, alkylation, and nucleophilic substitution. The compound is used in various synthetic routes, particularly when a selective base is required that does not form insoluble salts with organic acids. Additionally, tetraethylammonium hydroxide is employed in the synthesis of a wide range of organic compounds, including heterocycles, alkylated derivatives, and ionic liquids.

In the area of ionic liquid chemistry, tetraethylammonium hydroxide plays a crucial role in the preparation of ionic liquids. These ionic liquids are salts that remain liquid at or near room temperature and are increasingly used as solvents in chemical reactions, particularly in green chemistry. Ionic liquids made from tetraethylammonium hydroxide have found applications in a wide range of industrial processes, including catalysis, extraction, and electrochemical applications.

Tetraethylammonium hydroxide has also been explored in the field of electrochemistry, where it is used as a component of ionic liquid electrolytes. These electrolytes are used in energy storage devices, such as batteries and capacitors, and in electrochemical reactions. The compound's strong basicity and ability to stabilize certain ions make it a valuable component in the development of new electrochemical systems and materials.

Moreover, tetraethylammonium hydroxide has applications in analytical chemistry, particularly in ion exchange and separation processes. It is used in some forms of chromatography and is a useful reagent in the preparation of membranes and other separation materials.

Despite its usefulness in various chemical applications, tetraethylammonium hydroxide must be handled with care. As a strong base, it is highly caustic and can cause serious damage to tissues upon contact. Appropriate safety measures, including the use of gloves, goggles, and proper ventilation, are essential when working with this compound.

In conclusion, tetraethylammonium hydroxide is a versatile chemical with a wide range of applications in organic synthesis, ionic liquid chemistry, electrochemistry, and analytical chemistry. Its strong basicity and role in the preparation of ionic liquids and electrochemical systems make it valuable in both industrial and research settings.

References

2024 Research Status of Copper Film Slurries for Through-Silicon Via Process. Journal of Electronic Materials, 1, 11629.
DOI: 10.1007/s11664-024-11629-1

2024 Effects of potassium-mediated electrical communication inhibition on nitrogen removal in microbial fuel cells. Environmental Research, 1, 119822.
DOI: 10.1016/j.envres.2024.119822

2024 Recent Advancements of SAPO-34 and ZSM-5 Zeolite in Converting Methanol to Olefin: A Review. Arabian Journal for Science and Engineering, 1, 9786.
DOI: 10.1007/s13369-024-09786-w