Sodium ethoxide
[CAS# 141-52-6]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic sodium
• Name: Sodium ethoxide
• Synonyms: Sodium ethylate
• Molecular Formula: C₂H₅NaO
• Molecular Weight: 68.05
• CAS Registry Number: 141-52-6
• EC Number: 205-487-5
• SMILES: CC[O-].[Na+]

Properties

• Density: 0.868
• Boiling point: 91 ºC
• Refractive index: 1.385
• Flash point: 22 ºC
• Water solubility: Miscible

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Hazard Statements: H228-H251-H314-H318
• Precautionary Statements: P210-P235-P240-P241-P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P370+P378-P405-P407-P410-P413-P420-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Self-heating substances or mixtures	Self-heat.	1	H251
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Flammable solids	Flam. Sol.	1	H228
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	4	H302
Self-heating substances or mixtures	Self-heat.	2	H252
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 3206

Discovory and Applicatios

Sodium ethoxide, represented by the chemical formula C₂H₅ONa, is an alkoxide compound formed by the reaction of sodium metal with ethanol. It appears as a white, hygroscopic solid that is highly soluble in ethanol and other organic solvents. Sodium ethoxide is classified as a strong base and is widely used in various chemical applications, particularly in organic synthesis and as a reagent in numerous reactions.

The discovery of sodium ethoxide dates back to the early studies of alkoxide chemistry, which gained prominence in the 19th century. Chemists were exploring the reactivity of alkali metals with alcohols to form alkoxides, which led to the identification of various alkoxide compounds, including sodium ethoxide. The synthesis typically involves the direct reaction of sodium with an excess of ethanol, resulting in the formation of sodium ethoxide and the release of hydrogen gas. This reaction is both straightforward and efficient, making sodium ethoxide a readily available reagent in the laboratory.

Sodium ethoxide is primarily used as a strong base in organic synthesis. Its basicity allows it to deprotonate various compounds, making it a useful reagent in the formation of enolates, which are crucial intermediates in many organic reactions. For example, sodium ethoxide is commonly employed in aldol condensations, where it assists in generating enolate ions from carbonyl compounds. These enolates can then react with other carbonyl compounds to form β-hydroxy carbonyl compounds, which are key building blocks in the synthesis of more complex organic molecules.

Another significant application of sodium ethoxide is in the preparation of esters and ethers. It serves as a catalyst in the transesterification of fats and oils, a process essential in biodiesel production. In this context, sodium ethoxide facilitates the reaction between triglycerides and alcohols to yield fatty acid esters. This application is particularly relevant in the growing field of renewable energy, where biodiesel is becoming an increasingly important alternative to fossil fuels.

In addition to its use in organic synthesis, sodium ethoxide is also applied in the field of materials science. It is involved in the synthesis of various metal alkoxides, which are precursors for producing metal oxides through sol-gel processes. Metal oxides derived from sodium ethoxide can be used in applications such as catalysts, sensors, and thin films for electronics. The ability to control the properties of these metal oxides through the choice of alkoxide precursors has made sodium ethoxide a valuable compound in advanced materials research.

Sodium ethoxide has also been utilized in the pharmaceutical industry, where it plays a role in the synthesis of various active pharmaceutical ingredients (APIs). Its ability to facilitate specific chemical transformations enables the production of compounds that may be challenging to synthesize using other methods. This aspect of sodium ethoxide's utility underscores its significance in the development of new drugs and therapeutic agents.

While sodium ethoxide is a highly effective reagent, it must be handled with care due to its corrosive nature and potential hazards. It can react violently with water, releasing flammable hydrogen gas and creating caustic solutions. Therefore, it is essential to store sodium ethoxide in airtight containers, away from moisture and incompatible substances. Proper personal protective equipment, including gloves and safety goggles, should be used when handling this compound.

In summary, sodium ethoxide is a versatile alkoxide compound with a wide range of applications in organic synthesis, materials science, and pharmaceuticals. Its discovery marked a significant advancement in the understanding of alkoxide chemistry, paving the way for its use as a crucial reagent in various chemical processes. The ongoing exploration of sodium ethoxide's properties and applications continues to reveal its importance in modern chemistry.

References

2015. A Novel Coumarin-Based Fluorescent Probe for the Detection of Hydrazine Both in Aqueous Solution and Vapor State. Journal of Fluorescence. Yu-Hao Xiao, Gang Xi, Xuan-Xuan Zhao, Shuai Zhou, Ze-Quan Zhou, Bao-Xiang Zhao.
DOI: 10.1007/s10895-015-1586-1

2016. Substituted tetrazoles as multipurpose screening compounds. Molecular Diversity. Nicole Rüger, Georg Michael Fassauer, Christian Bock, Thomas Emmrich, Anja Bodtke, Andreas Link.
DOI: 10.1007/s11030-016-9711-x

2006. Improving the Quality of the Quartz Fiber Postcore Bond Using Sodium Ethoxide Etching and Combined Silane/Adhesive Coupling. Journal of Endodontics. Francesca Monticelli, Raquel Osorio, Manuel Toledano, Cecilia Goracci, Franklin R. Tay, Marco Ferrari.
DOI: 10.1016/j.joen.2005.10.061