Ethylene carbonate
[CAS# 96-49-1]

Identification

• Classification: Organic raw materials >> Inorganic acid ester
• Name: Ethylene carbonate
• Synonyms: 1,3-Dioxolan-2-one; Ethylene glycol carbonate
• Molecular Formula: C₃H₄O₃
• Molecular Weight: 88.06
• CAS Registry Number: 96-49-1
• EC Number: 202-510-0
• SMILES: C1COC(=O)O1

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*, 1.321 g/mL (Expl.)
• Melting point: 35 - 38 °C (Expl.)
• Boiling point: 248.2 °C 760 mmHg (Calc.)^*, 244.3 - 245.3 °C (Expl.)
• Flash point: 160.0 °C (Calc.)^*, 143 °C (Expl.)
• Solubility: water: 214 g/L (20 °C) (Expl.)
• Index of refraction: 1.424 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302-H315-H319-H373
• Safety Statements: P260-P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Ethylene carbonate is an organic carbonate with the molecular formula C₃H₄O₃. Structurally, it is a five-membered cyclic carbonate consisting of a carbonyl group bonded to a ring containing two methylene units and an oxygen atom, forming a cyclic ester of carbonic acid. The compound is typically a colorless, odorless solid with a relatively high melting point and good thermal stability. It is highly polar and soluble in water as well as in a variety of organic solvents such as acetonitrile, dimethylformamide, and dimethyl sulfoxide.

Ethylene carbonate is primarily used as a solvent and electrolyte component in lithium-ion batteries. Its high dielectric constant, chemical stability, and ability to dissolve lithium salts make it a critical component in electrolytes, facilitating efficient ion transport and battery performance. It also contributes to the formation of stable solid-electrolyte interphases on electrode surfaces, which is essential for long-term cycling stability.

In addition to battery applications, ethylene carbonate is employed as a reactive intermediate in organic synthesis. Its cyclic carbonate functionality allows it to participate in ring-opening reactions to generate mono- or di-functionalized derivatives, which are useful in the synthesis of polycarbonates, pharmaceuticals, and fine chemicals. It can react with nucleophiles, such as amines and alcohols, to produce carbamates or hydroxyethyl derivatives.

Ethylene carbonate is typically produced by the reaction of ethylene oxide with carbon dioxide under catalytic conditions, a process that is both efficient and environmentally favorable due to the use of CO₂ as a feedstock. Handling precautions include avoiding exposure to strong acids or bases, which can hydrolyze the carbonate ring, and using standard measures for high-purity solvents.

Overall, ethylene carbonate is a highly versatile cyclic carbonate with applications in energy storage, organic synthesis, and polymer production. Its polar, thermally stable structure and reactive carbonate ring make it valuable as both a solvent and a chemical intermediate in industrial and laboratory settings.

References

2013. Hydrothermal Synthesis of Nickel Oxide Nanosheets for Lithium-Ion Batteries and Supercapacitors with Excellent Performance. Chemistry – An Asian Journal, 8(10).
DOI: 10.1002/asia.201300708

2012. Polymers containing phosphorus groups and polyethers: from synthesis to application. Chemistry Central Journal, 6(1).
DOI: 10.1186/1752-153x-6-132