Dimethyl carbonate
[CAS# 616-38-6]

Identification

• Classification: Chemical pesticide >> Herbicide >> Carbamate herbicide
• Name: Dimethyl carbonate
• Synonyms: Methyl carbonate; Carbonic acid dimethyl ester
• Molecular Formula: C₃H₆O₃
• Molecular Weight: 90.08
• CAS Registry Number: 616-38-6
• EC Number: 210-478-4
• SMILES: COC(=O)OC

Properties

• Density: 1.069 g/mL (Expl.)
• Melting point: 2-4 °C (Expl.)
• Boiling point: 90 °C (Expl.)
• Refractive index: 1.369 (Expl.)
• Flash point: 16 °C (Expl.)
• Water solubility: insoluble (Expl.)

Safety Data

• Hazard Symbols: GHS02 Danger
• Risk Statements: H225
• Safety Statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 1161

Discovery and Applications

Dimethyl carbonate (DMC) is an organic compound with the chemical formula (CH₃O)₂CO. It is a colorless, volatile liquid that has a sweet odor and is widely used as a solvent and reagent in various industrial processes. DMC is regarded as a green alternative to more toxic chemicals like phosgene and methyl chloroformate due to its low toxicity, biodegradability, and versatility in a variety of chemical applications. Its discovery and development have been driven by the need for safer and more sustainable chemical processes in industries such as pharmaceuticals, polymers, and energy production.

Dimethyl carbonate was first synthesized in the mid-19th century, although its industrial applications did not become significant until the latter half of the 20th century. Early work on the compound focused on its synthesis from methanol and carbon dioxide, using various catalysts under specific conditions. The increased interest in DMC during the 1970s and 1980s was driven by the search for environmentally safer alternatives to traditional chemicals used in the production of polycarbonates, solvents, and other organic compounds. One of the key breakthroughs in DMC production came from advances in catalysis and the use of renewable carbon dioxide, a process that was seen as more sustainable than other methods that relied on hazardous raw materials.

One of the most important applications of dimethyl carbonate is as a solvent. It is used in a wide range of industries, including pharmaceuticals, coatings, adhesives, and paints. Its ability to dissolve both polar and nonpolar compounds makes it an ideal solvent for various formulations, and it is often used as a substitute for more toxic solvents such as methylene chloride or acetone. DMC's low toxicity and relatively low evaporation rate also make it safer for use in products that come into contact with humans, such as cosmetics and household cleaners.

In addition to its use as a solvent, dimethyl carbonate is a critical reagent in the production of polycarbonate plastics. Polycarbonates are durable, transparent, and lightweight materials that are used in a variety of applications, including the manufacture of eyewear lenses, optical discs, automotive parts, and electrical components. DMC is used as a precursor in the synthesis of these polycarbonates through a reaction with bisphenol A (BPA), a compound that serves as the backbone for polycarbonate production. The use of DMC in polycarbonate manufacturing is considered environmentally friendly, as it avoids the use of phosgene, a highly toxic and dangerous chemical previously used in the production of these plastics.

Dimethyl carbonate is also used in the synthesis of methyl esters and other chemicals. It acts as a methylating agent, introducing the methyl group (-CH₃) into various chemical reactions. This property is particularly useful in the production of methyl ethers, which are valuable intermediates in the synthesis of pharmaceuticals, agrochemicals, and fragrances. DMC's reactivity and versatility make it an important tool in the chemical industry for producing a variety of valuable compounds.

Another significant application of dimethyl carbonate is in the field of energy storage. DMC is used as an electrolyte solvent in lithium-ion batteries, which are commonly used in portable electronics and electric vehicles. The compound helps improve the stability and performance of the battery by enhancing the ionic conductivity and reducing the risk of overheating, thus contributing to the overall safety and efficiency of these energy storage devices.

Furthermore, DMC has been explored as a potential green solvent in biodiesel production. It can react with fatty acids in vegetable oils to produce biodiesel and methanol, offering a safer and more environmentally friendly alternative to conventional transesterification processes that use methanol and sodium hydroxide. The development of DMC-based biodiesel processes could play a role in the future of renewable energy production.

In conclusion, dimethyl carbonate is a highly versatile and valuable chemical with a broad range of applications. Its role as a solvent, reagent, and precursor in the production of polycarbonates and other important chemicals underscores its significance in the chemical and materials industries. Additionally, its environmentally friendly characteristics make it an important component in the development of sustainable products and processes.

References

2024. Optimization of AlOOH powder characteristics for enhanced separator performance and stability in lithium-ion batteries. Journal of the Korean Ceramic Society, 61(3).
DOI: 10.1007/s43207-024-00464-z

2024. LiNbO3 coating improves property of LiNi0.5Mn1.5O4 for lithium-ion battery cathode materials. Ionics, 30(6).
DOI: 10.1007/s11581-024-05991-7

2024. Enhanced electrochemical performance of Li-rich cathode materials at high temperatures through fluorine and magnesium modification. Journal of Materials Science: Materials in Electronics, 35(24).
DOI: 10.1007/s10854-024-14011-3