Sodium methanolate
[CAS# 124-41-4]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic sodium
• Name: Sodium methanolate
• Synonyms: Sodium methoxide; Sodium methylate
• Molecular Formula: CH₃NaO
• Molecular Weight: 54.02
• CAS Registry Number: 124-41-4
• EC Number: 204-699-5
• SMILES: C[O-].[Na+]

Properties

• Density: 0.945 g/mL
• Melting point: -2 °C
• Boiling Point: 93 °CFlash point
• Water solubility: reacts

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H228-H251-H290-H302-H314-H318
• Safety Statements: P210-P234-P235-P240-P241-P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P370+P378-P390-P405-P406-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
Acute toxicity	Acute Tox.	4	H302
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Serious eye damage	Eye Dam.	1	H318
Flammable solids	Flam. Sol.	1	H228
Skin corrosion	Skin Corr.	1A	H314
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	1	H370
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Pyrophoric solids	Pyr. Sol.	1	H250

• Transport Information: UN 1431

Discovery and Applications

Sodium methanolate, also known as sodium methylate, is an organic compound with the formula NaOCH3. It is a white, hygroscopic solid that is soluble in methanol and other polar solvents. Sodium methanolate is primarily used as a strong base in organic synthesis, where it plays a crucial role in various chemical reactions. The compound is a derivative of methanol, where the hydroxyl group (-OH) is replaced by a sodium atom, resulting in a highly reactive species.

The discovery of sodium methanolate can be traced back to the mid-20th century, during a period of increased interest in the development of efficient chemical reagents. Researchers were exploring methods to produce alkoxides, which are essential intermediates in organic synthesis. The synthesis of sodium methanolate is typically achieved by reacting sodium metal with methanol, a straightforward process that produces sodium methanolate along with hydrogen gas. This method exemplifies a classic approach to generating alkoxides from their corresponding alcohols.

In organic chemistry, sodium methanolate serves as a powerful nucleophile and base. It is widely employed in the synthesis of various organic compounds, particularly in the preparation of esters, ethers, and other functionalized molecules. One of its notable applications is in the transesterification reaction, where it catalyzes the conversion of triglycerides into biodiesel. This process involves the reaction of triglycerides with methanol, leading to the production of fatty acid methyl esters and glycerol. Sodium methanolate's efficiency in this reaction has made it a preferred choice in biodiesel production, contributing to the growing interest in renewable energy sources.

In addition to its role in biodiesel synthesis, sodium methanolate is also used in the production of pharmaceuticals and agrochemicals. Its ability to facilitate nucleophilic substitutions makes it an important reagent in the synthesis of various bioactive compounds. Furthermore, sodium methanolate is utilized in polymer chemistry, particularly in the preparation of poly(methyl methacrylate) (PMMA) and other methacrylate-based polymers, which are widely used in coatings, adhesives, and medical devices.

Safety considerations are paramount when handling sodium methanolate. It is a highly reactive and flammable substance that can cause skin and eye irritation upon contact. Proper personal protective equipment (PPE), including gloves and goggles, is essential during its use. Additionally, due to its hygroscopic nature, sodium methanolate should be stored in a dry environment to prevent degradation and moisture absorption.

Research into sodium methanolate continues to evolve, with ongoing studies focusing on its applications in green chemistry and sustainable processes. The search for more environmentally friendly methods of chemical synthesis aligns with the principles of green chemistry, and sodium methanolate's utility in various reactions positions it as a valuable reagent in this field.

In conclusion, sodium methanolate is a significant chemical compound with diverse applications in organic synthesis, biodiesel production, and the pharmaceutical industry. Its discovery marked a milestone in the development of alkoxides as essential reagents in chemistry. As the demand for sustainable and efficient chemical processes grows, sodium methanolate's relevance is likely to increase, further establishing its role in modern chemical research and industry.

References

1979. Methanolysis of cholesteryl esters: Conditions for quantitative preparation of methyl esters. Analytical Biochemistry.
DOI: 10.1016/0003-2697(79)90381-6

2023. Synthesis of Diethanolamide Surfactant from Palm Oil by Esterification and Amidation Processes. The 6th Mechanical Engineering, Science and Technology (MEST 2022) International Conference.
DOI: 10.2991/978-94-6463-134-0_9

2024. Experimental Investigation of a Rapid Rate Cyclone Type Transesterification Reactor. Proceedings of the 9th International Symposium on Hydrogen Energy, Renewable Energy and Materials.
DOI: 10.1007/978-981-97-3686-7_14