Ethyl vinyl ether
[CAS# 109-92-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: Ethyl vinyl ether
• Synonyms: Ethoxyethene
• Molecular Formula: C₄H₈O
• Molecular Weight: 72.11
• CAS Registry Number: 109-92-2
• EC Number: 203-718-4
• SMILES: CCOC=C

Properties

• Density: 0.754
• Melting point: -116 °C
• Boiling point: 36 °C
• Refractive index: 1.376-1.378
• Flash point: -45 °C
• Water solubility: 7.8 g/L (25 °C)

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H225-H319-H336
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264+P265-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P319-P337+P317-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Flammable liquids	Flam. Liq.	2	H225
Specific target organ toxicity - single exposure	STOT SE	3	H336
Flammable liquids	Flam. Liq.	1	H224
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1302

Discovery and Applications

Ethyl vinyl ether, with the chemical formula C4H8O, is a versatile compound. Ethyl vinyl ether was first synthesized and characterized in the early 20th century when chemists were exploring the reactivity of vinyl compounds and their derivatives. Its discovery helped expand the range of available ethers and provided new pathways for organic reactions. Ethyl vinyl ether has an ethoxy group (-OCH₂CH₃) attached to a vinyl group (-CH=CH₂). It is a colorless, volatile liquid with an ethereal odor. It has a boiling point of about 35°C and is soluble in organic solvents but slightly soluble in water.

Ethyl vinyl ether is a versatile reagent in organic chemistry due to its ability to undergo a variety of transformations. It is often used in the synthesis of pharmaceuticals, agrochemicals, and fragrances. Its vinyl group is able to participate in polymerization and cross-coupling reactions, which expands its usefulness in the synthesis of complex organic molecules.

As a specialty solvent, ethyl vinyl ether finds application in the polymer industry, particularly in the production of specialty resins and coatings. It can act as a cosolvent or reaction medium during polymerization, helping to form specific polymer structures and properties.

Ethyl vinyl ether has been explored as a fuel additive. Its oxygen-containing functional groups can improve the combustion efficiency of fuels, thereby reducing emissions and improving fuel performance.

Ethyl vinyl ether is extremely flammable and should be handled with care. Proper storage and handling procedures, including adequate ventilation and fire protection, are essential to reduce risks. Information on its acute toxicity is limited, but it is generally considered to be low. However, prolonged or repeated exposure may irritate the respiratory system and skin.

Ethyl vinyl ether is biodegradable under aerobic conditions, although the specific degradation pathways may vary. Its environmental impact is primarily related to its flammability and potential as a volatile organic compound (VOC).

References

2021. Bottlebrush polymers with flexible enantiomeric side chains display differential biological properties. Nature Chemistry.
DOI: 10.1038/s41557-021-00826-8

2013. Ozone-Induced Dissociation of Conjugated Lipids Reveals Significant Reaction Rate Enhancements and Characteristic Odd-Electron Product Ions. Journal of The American Society for Mass Spectrometry.
DOI: 10.1007/s13361-012-0521-9

2012. CO2-Activation for γ-Butyrolactones and Its Application in the Total Synthesis of (±)-Heteroplexisolide E. Chemistry - An Asian Journal.
DOI: 10.1002/asia.201200467