Vinylene carbonate
[CAS# 872-36-6]

Identification

• Classification: Organic raw materials >> Inorganic acid ester
• Name: Vinylene carbonate
• Synonyms: 1,3-Dioxo-2-one
• Molecular Formula: C₃H₂O₃
• Molecular Weight: 86.05
• CAS Registry Number: 872-36-6
• EC Number: 212-825-5
• SMILES: C1=COC(=O)O1

Properties

• Density: 1.355 g/mL (Expl.)
• Melting point: 19-22 °C (Expl.)
• Boiling point: 162 °C (Expl.)
• Refractive index: 1.421 (Expl.)
• Flash point: 83 °C (Expl.)
• Water solubility: 11.5 g/100 mL (Expl.)

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H311-H315-H317-H318-H361-H373-H411
• Safety Statements: P203-P260-P261-P262-P264-P264+P265-P270-P272-P273-P280-P301+P317-P302+P352-P305+P354+P338-P316-P317-P318-P319-P321-P330-P332+P317-P333+P317-P361+P364-P362+P364-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	3	H311
Reproductive toxicity	Repr.	2	H361
Eye irritation	Eye Irrit.	2	H319
Flammable liquids	Flam. Liq.	4	H227
Skin sensitization	Skin Sens.	1B	H317

Discovery and Applications

Vinylene carbonate is an organic compound with the chemical formula C3H4O3, primarily used in the production of lithium-ion batteries, polymer chemistry, and other specialized chemical applications. This compound is a cyclic ester, featuring a structure that includes an alkene group (vinyl) bonded to a carbonate ring. Its unique molecular architecture contributes to its useful properties in various industrial applications. Vinylene carbonate has gained attention for its role as an electrolyte additive in lithium-ion batteries, where it improves the performance and longevity of the batteries.

The discovery of vinylene carbonate dates back to the mid-20th century, when researchers began exploring new chemical substances with applications in the emerging field of electrochemistry. Its synthesis involves a straightforward process, often achieved by the reaction of ethylene carbonate with a vinyl group, typically through a ring-opening mechanism or by reacting alkene derivatives with carbon dioxide. The initial uses of vinylene carbonate were focused on its chemical reactivity, especially its potential as a solvent and additive in polymerization reactions. Over time, however, its application in energy storage technologies, particularly in lithium-ion batteries, became the primary area of interest.

In lithium-ion batteries, vinylene carbonate is commonly used as an additive in the electrolyte solution. When incorporated into the electrolyte, vinylene carbonate undergoes a process known as "solid electrolyte interface" (SEI) formation. The SEI is crucial for the long-term stability of the battery, as it prevents the electrolyte from degrading and ensures efficient ion transport within the battery during charge and discharge cycles. The addition of vinylene carbonate helps to stabilize the SEI, reducing the risk of performance degradation and prolonging the life of the battery. This has made it an essential component in high-performance lithium-ion batteries used in electric vehicles, consumer electronics, and energy storage systems.

Beyond its role in energy storage, vinylene carbonate also has applications in polymer chemistry. It is utilized as a monomer in the production of various types of polymers, including polycarbonate and polyurethane, where it contributes to the formation of copolymers with unique properties such as enhanced thermal stability and mechanical strength. Vinylene carbonate's versatility in polymer applications has made it a useful component in the manufacture of plastics and coatings for a wide range of industrial products.

Moreover, vinylene carbonate is being explored for use in other niche applications, such as in the development of organic photovoltaic cells (OPVs) and other organic electronics. The compound’s ability to participate in reactions that modify the electronic properties of materials makes it a potential candidate for use in the creation of more efficient and durable organic electronic devices.

As the demand for sustainable energy solutions and high-performance materials grows, vinylene carbonate's role in battery technology and materials science is expected to expand further. Its combination of electrochemical stability, chemical reactivity, and versatility in polymer chemistry ensures that it will continue to be a valuable compound in both current and future technological applications.

References

2024. Tailoring Cathode-Electrolyte Interface for High-Power and Stable Lithium-Sulfur Batteries. Nano-Micro Letters, 17(1).
DOI: 10.1007/s40820-024-01573-4

2024. Ester-based electrolytes for graphite solid electrolyte interface layer stabilization and low-temperature performance in lithium-ion batteries. Carbon Letters, 34(4).
DOI: 10.1007/s42823-024-00749-7

2024. Based on an environmental-friendly society, material modification technique to improve the performance of the lithium-ion battery. Environment, Development and Sustainability, 26(10).
DOI: 10.1007/s10668-024-05663-6