422177

Ethyl vinyl ether

contains 0.1% KOH as stabilizer, 99%

• Synonym(s): Ethoxyethylene
• Linear Formula: C₂H₅OCH=CH₂
• CAS Number: 109-92-2
• Molecular Weight: 72.11
• Beilstein: 605351
• EC Number: 203-718-4
• MDL number: MFCD00009248
• UNSPSC Code: 12162002
• eCl@ss: 39021025
• PubChem Substance ID: 24866417
• NACRES: NA.23

Properties

• Assay: 99%
• form: liquid
• contains: 0.1% KOH as stabilizer; 0.1% potassium hydroxide as stabilizer
• refractive index: n20/D 1.376 (lit.)
• bp: 33 °C (lit.)
• mp: −116 °C (lit.)
• density: 0.753 g/mL at 25 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: CCOC=C
• InChI: 1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3
• InChI key: FJKIXWOMBXYWOQ-UHFFFAOYSA-N

Description

General description

Ethyl vinyl ether, also known as ethoxy ethane is highly reactive due to the presence of the vinyl group and the ether functionality. It can polymerize via different methods like radical polymerization, cationic polymerization, oroxidative polymerization, yielding poly(ethyl vinyl ether) or PVE. It is widely used as a monomer to synthesize copolymers and block polymers with thermal stability and flexibility for various applications such as the synthesis of silicone hydrogel for contact lenses, tissue engineering, 3D bioprinting, drug delivery, and Li-ion batteries.

Application

Ethyl vinyl ether can be used as:

• A monomer to synthesize amphiphilic block copolymers to fabricate protein-repelling polymersomes to produce spherical nanoparticles. These nanoparticles can be used as drug carriers.
• A precursor to synthesize polymer electrolytes and cathode materials for solid-state lithium-ion batteries via UV photopolymerizations.
• A monomer to synthesize poly(vinyl ether)s with controlled molecular weight and narrow dispersity via photoinduced free radical-promoted cationic reversible addition–fragmentation chain transfer (RAFT) polymerization. These polymers are used to fabricate 3D objects with different thicknesses by employing stereolithography-based 3D printing.

• H-bonded Reusable Template Assisted para-Selective Ketonisation: This study discusses the use of ethyl vinyl ether in catalytic processes involving palladium and hexafluoroisopropanol to achieve para-selectivity in ketonisation, relevant for synthesizing complex organic compounds used in pharmaceuticals and materials science (A Maji, A Dahiya, G Lu, T Bhattacharya, 2018).


• Mechanistic Insight into Photocontrolled Cationic Polymerization: Explores the photocontrolled polymerization of ethyl vinyl ether, providing valuable knowledge for the development of light-responsive materials, which could have applications in drug delivery and smart material systems (Q Michaudel, T Chauviré, V Kottisch, 2017).

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H336,H412
• Precautionary Statements: P210 - P233 - P240 - P241 - P242 - P273
• Hazard Classifications: Aquatic Chronic 3 - Flam. Liq. 2 - STOT SE 3
• Target Organs: Central nervous system
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 1
• Flash Point(F): -49.0 °F
• Flash Point(C): -45 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves