Vinyl ether (C4H6O) is a chemical compound used in various applications. It possesses unique properties, such as reactivity and low toxicity, making it valuable in industries like pharmaceuticals and organic synthesis.
| IUPAC Name | Ethoxyethene |
| Molecular Formula | C4H6O |
| CAS Number | 109-93-3 |
| Synonyms | Divinyl ether; 1,1′-Oxybisethene; Oxirane, Divinyl oxide, Vinether |
| InChI | InChI=1S/C4H6O/c1-2-5-4-3-1/h1-4H2 |
Vinyl Ether Properties
Vinyl Ether Formula
The formula for vinyl ether is C4H6O. It consists of four carbon atoms, six hydrogen atoms, and one oxygen atom. This molecular formula represents the composition of vinyl ether, providing information about the types and number of atoms present in a single molecule.
Vinyl Ether Molar Mass
The molar mass of divinyl ether is calculated by adding up the atomic masses of all the atoms in its formula. The molar mass of C4H6O (divinyl ether) is approximately 70.09 grams per mole. This value is crucial for various calculations, such as determining the amount of divinyl ether needed in reactions.
Vinyl Ether Boiling Point
Divinyl ether has a boiling point of around 34.6 degrees Celsius (94.3 degrees Fahrenheit). This temperature indicates the point at which divinyl ether undergoes a phase change from a liquid to a gas under standard atmospheric pressure. The relatively low boiling point makes divinyl ether useful in certain applications and processes.
Vinyl Ether Melting Point
The melting point of divinyl ether is approximately -116 degrees Celsius (-177 degrees Fahrenheit). This temperature denotes the point at which divinyl ether transitions from a solid to a liquid state. The low melting point is significant as it affects the handling and storage of divinyl ether.
Vinyl Ether Density g/mL
The density of divinyl ether is around 0.734 grams per milliliter (g/mL). Density refers to the mass of a substance per unit volume. The density of divinyl ether provides information about its compactness or concentration, which can be useful for various applications, including formulation and dosage calculations.
Vinyl Ether Molecular Weight
The molecular weight of divinyl ether is approximately 70.09 grams per mole. It represents the mass of one mole of divinyl ether molecules. The molecular weight is crucial for various calculations, including determining the number of molecules or moles present in a given quantity of divinyl ether.
Vinyl Ether Structure
The structure of divinyl ether consists of two carbon-carbon double bonds (C=C) and an oxygen atom bonded to two of the carbons (C-O). This arrangement gives divinyl ether its unique properties and reactivity. Understanding the structure is important for studying its behavior in chemical reactions and interactions with other substances.
Vinyl Ether Solubility
Divinyl ether is sparingly soluble in water but can dissolve in organic solvents such as ethanol, acetone, and chloroform. Its solubility depends on factors like temperature and the nature of the solvent. Knowledge of divinyl ether’s solubility is crucial when considering its applications, formulations, and compatibility with other substances.
| Appearance | Colorless liquid |
| Specific Gravity | 0.734 g/mL |
| Color | N/A |
| Odor | Sweet, ether-like odor |
| Molar Mass | 70.09 g/mol |
| Density | 0.734 g/mL |
| Melting Point | -116°C (-177°F) |
| Boiling Point | 34.6°C (94.3°F) |
| Flash Point | -40°C (-40°F) |
| Water Solubility | Sparingly soluble |
| Solubility | Soluble in organic solvents |
| Vapour Pressure | 155 mmHg at 20°C |
| Vapour Density | 2.50 (air = 1) |
| pKa | N/A |
| pH | N/A |
Vinyl Ether Safety and Hazards
Divinyl ether poses certain safety hazards that must be taken into account. It is flammable and can form explosive mixtures with air. Therefore, it should be stored and handled away from open flames or sources of ignition. Divinyl ether vapors can cause irritation to the respiratory system and eyes. Direct contact with the skin may result in dermatitis or chemical burns. Adequate ventilation and personal protective equipment should be used when working with divinyl ether. Additionally, it is essential to follow proper disposal procedures to prevent environmental contamination. Overall, adherence to safety protocols is crucial to minimize risks associated with divinyl ether.
| Hazard Symbols | Flammable, Harmful |
| Safety Description | Keep away from open flames. Use in a well-ventilated area. Avoid direct contact with skin and eyes. Properly dispose of waste. |
| UN IDs | UN 1159 |
| HS Code | 2909.19.00 |
| Hazard Class | Class 3 (Flammable liquids) |
| Packing Group | PG II |
| Toxicity | Harmful if swallowed or inhaled. May cause irritation or burns to the skin and eyes. |
Vinyl Ether Synthesis Methods
There are several methods for synthesizing divinyl ether.
One common approach is the reaction between ethanol and acetylene in the presence of an acidic catalyst, such as sulfuric acid or p-toluenesulfonic acid. This results in the formation of divinyl ether as a product. Another method involves the addition of an alkoxide ion to acetylene, which generates a divinyl ether intermediate that can be further converted into divinyl ether by protonation.
One can prepare divinyl ether by reacting an alcohol with vinyl halides, such as vinyl chloride or vinyl bromide, through an etherification reaction. This reaction requires the presence of a base, such as sodium or potassium carbonate, to facilitate the formation of the desired divinyl ether.
To synthesize divinyl ether, one can react alkynes with alkyl halides in the presence of a strong base, such as sodium amide. This process, known as the Favorskii rearrangement, results in the conversion of the alkyl halide into a divinyl ether.
The reaction of aldehydes or ketones with ethyl divinyl ether, using Lewis acid catalysts like zinc chloride or aluminum chloride, allows for the preparation of divinyl ether derivatives. This process, known as the Prins reaction, enables the formation of various divinyl ether derivatives.
Vinyl Ether Uses
Divinyl ether finds utility in various applications due to its unique properties. Here are some common uses:
- Divinyl ether plays a crucial role as a precursor in synthesizing pharmaceutical compounds and aids in producing anesthesia agents, muscle relaxants, and other medicinal substances.
- Organic synthesis benefits greatly from the versatility of divinyl ether as it serves as a versatile building block in various reactions, including cross-coupling reactions, polymerizations, and cycloadditions, resulting in valuable organic compounds.
- Divinyl ether acts as an intermediate in the production of a wide range of chemicals, such as solvents, adhesives, coatings, and plasticizers, enabling the creation of tailored compounds for specific applications.
- The rapid polymerization of divinyl ether under ultraviolet light makes it a valuable component in UV-curable coatings and adhesives, providing durable and fast-curing coatings for applications in the automotive, electronics, and printing industries.
- Copolymerization of divinyl ether with other monomers generates copolymers possessing unique properties for various applications, such as drug delivery systems, biomaterials, and coatings.
- By functioning as a cross-linking agent, divinyl ether enhances the production of cross-linked polymers, which exhibit improved mechanical strength, chemical resistance, and thermal stability, thus proving valuable in various industries.
- Divinyl ether serves as a vital tool in laboratory research and development, enabling scientists to explore new reactions, develop novel materials, and advance scientific understanding, owing to its reactivity and versatility.
Questions:
Q: Are vinyl ethers stable?
A: Divinyl ethers are generally stable compounds, but their stability can vary depending on specific structural features and reaction conditions.
Q: How to draw the structure of vinyl ether?
A: To draw the structure of Divinyl ether, represent a carbon-carbon double bond (C=C) with one carbon bonded to an oxygen atom (C-O).
Q: What is vinyl ether/maleic acid in Polygrip?
A: Divinyl ether/maleic acid copolymer is used in Polygrip as a denture adhesive. It helps provide adhesion between the denture and gums.
Q: How to make vinyl ether?
A: Divinyl ether can be made through various methods, such as the reaction between ethanol and acetylene or the etherification of alcohols with vinyl halides.
Q: How to synthesize vinyl ethers?
A: Divinyl ethers can be synthesized through different routes, including reactions involving alcohols, alkynes, and alkyl halides, as well as Prins reactions and Favorskii rearrangements.
Q: Is vinyl ether a Michael acceptor?
A: Divinyl ethers are not typically considered Michael acceptors as they do not possess an α,β-unsaturated carbonyl group that is characteristic of Michael acceptors.
Q: What is the role of ethyl vinyl ether in ROMP reactions?
A: Ethyl vinyl ether can serve as a co-monomer in Ring-Opening Metathesis Polymerization (ROMP) reactions, contributing to the formation of polymer chains with specific properties.
Q: Ethyl vinyl ether alcohol?
A: Ethyl vinyl ether alcohol does not exist as a distinct compound. Ethyl Divinyl ether is a separate compound and not an alcohol.