n-Butyl vinyl ether
[CAS# 111-34-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: n-Butyl vinyl ether
• Synonyms: 1-(Ethenyloxy)butane
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• CAS Registry Number: 111-34-2
• EC Number: 203-860-7
• SMILES: CCCCOC=C

Properties

• Density: 0.77
• Melting point: -92 °C
• Boiling point: 94 °C
• Refractive index: 1.4005-1.4025
• Flash point: -9 °C
• Water solubility: 3 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H225-H315-H317
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P272-P280-P302+P352-P303+P361+P353-P321-P332+P317-P333+P317-P362+P364-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
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 2352

Discovery and Applications

n-Butyl vinyl ether (BVE), with the chemical formula C8H12O, is an organic compound with a wide range of uses. The discovery of n-butyl vinyl ether dates back to the early 20th century, when vinyl ethers were being explored more extensively. It is synthesized by reacting acetylene with n-butanol in the presence of a catalyst, which is either an alkali metal or a metal halide. n-Butyl vinyl ether is characterized by its ether functionality, where a butyl group (C₄H₉) is bonded to a vinyl group (CH₂=CH−O−). This structure allows the vinyl group to provide a site for polymerization and addition reactions, and is reactive toward a variety of electrophiles and nucleophiles. BVE is soluble in a wide range of organic solvents, enhancing its usefulness in a variety of chemical reactions and formulations. Its relatively low boiling point (~94°C) and volatility make it suitable for processes that require easy removal or evaporation of the solvent.

n-Butyl vinyl ether is widely used as a monomer in the production of polymers and copolymers. It polymerizes via free radical, anionic or cationic mechanisms to form poly(n-butyl vinyl ether) and various copolymers. These polymers are used in coatings, adhesives and films for their flexibility, adhesive properties and resistance to moisture and chemicals.

BVE can be copolymerized with other monomers to introduce functional groups into the polymer chain. This modification allows the synthesis of specialty polymers with tailored properties, such as improved thermal stability, chemical resistance and specific mechanical properties. These functional polymers are used in high-performance materials, including automotive parts and electronics.

In polymer networks, n-butyl vinyl ether acts as a crosslinker, enhancing the mechanical strength and stability of the resulting material. Crosslinked polymers produced with BVE are used to make elastomers, resins and composites used in construction and industrial applications.

n-Butyl vinyl ether is a valuable organic synthesis intermediate that participates in a variety of addition, substitution and rearrangement reactions. It introduces vinyl ether functionality into complex molecules, facilitating the synthesis of pharmaceuticals, agrochemicals and fine chemicals.

BVE is used as a protecting group for alcohols and amines in organic synthesis. Its vinyl ether moiety can introduce sensitive functional groups, protecting them from unwanted reactions in the synthetic sequence. The protecting group can then be removed under mild conditions, restoring the original functionality.

Due to its solvent properties, n-butyl vinyl ether is used in formulations to dissolve other compounds and facilitate chemical reactions. Its volatility also allows for easy evaporation of solvents, such as coatings and inks.

n-butyl vinyl ether-based polymers are used in the formulation of coatings and adhesives, with desirable properties such as flexibility, bond strength, and resistance to environmental factors. These materials are used in automotive finishes, protective coatings, and industrial adhesives.

In the electronics industry, BVE-derived polymers are used as insulating materials, encapsulants, and coatings for electronic components. Their electrical properties and stability help improve the performance and lifespan of electronic devices.

Research on n-butyl vinyl ether-based materials has explored their potential in biomedical applications, including drug delivery systems, tissue engineering, and medical adhesives. The biocompatibility and versatility of BVE polymers offer opportunities for the development of advanced medical devices and therapies.

References

2024. Synthesis of degradable polymers via 1,5-shift radical isomerization polymerization of vinyl ether derivatives with a cleavable bond. Polymer Journal.
DOI: 10.1038/s41428-023-00869-3

2023. Formulated poly (butyl vinyl ether) adhesives as alternative materials for direct ink writing (DIW) 3D printing. MRS Communications.
DOI: 10.1557/s43579-023-00477-5

1954. Synthesis of sulfur compounds by the aid of vinyl ethers and acetylene. Communication 7. Peculiarities of the reaction of addition, contrary to Markov Nikov's rule, of hydrogen sulfide to butyl vinyl ether. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science.
DOI: 10.1007/bf01177619