Ethyl vinyl ether (C4H8O) is a volatile organic compound used as a solvent and in the production of polymers. It possesses a pleasant odor and is flammable.
| IUPAC Name | Ethoxyethene |
| Molecular Formula | C4H8O |
| CAS Number | 109-92-2 |
| Synonyms | Vinyl ethyl ether, Ethoxyethylene, EVE, EEE, VEVE |
| InChI | InChI=1S/C4H8O/c1-2-5-4-3-6-1/h1-4H2 |
Ethyl Vinyl Ether Properties
Ethyl Vinyl Ether Formula
The chemical formula of ethoxyethylene is C4H8O. It represents the composition of this compound, indicating that it contains four carbon atoms, eight hydrogen atoms, and one oxygen atom.
Ethyl Vinyl Ether Molar Mass
The molar mass of ethoxyethylene is calculated by summing the atomic masses of its constituent elements. In this case, it is approximately 72.11 grams per mole. Molar mass helps determine the amount of substance present in a given sample.
Ethyl Vinyl Ether Boiling Point
Ethoxyethylene has a boiling point of around 35-36 degrees Celsius (95-97 degrees Fahrenheit). This relatively low boiling point suggests that it can easily vaporize and transform into a gaseous state when heated.
Ethyl Vinyl Ether Melting Point
The melting point of ethoxyethylene is approximately -102 degrees Celsius (-152 degrees Fahrenheit). This indicates that it is a volatile compound that exists as a liquid at room temperature and freezes into a solid at very low temperatures.
Ethyl Vinyl Ether Density g/mL
The density of ethoxyethylene is about 0.73 grams per milliliter. This value signifies the mass of the compound per unit volume. The density of a substance is important for various applications, including determining its buoyancy and solubility.
Ethyl Vinyl Ether Molecular Weight
The molecular weight of ethoxyethylene is approximately 72.11 grams per mole. It represents the sum of the atomic weights of all atoms in a molecule. Molecular weight is crucial in various chemical calculations, such as stoichiometry and determining concentrations.
Ethyl Vinyl Ether Structure
Ethoxyethylene consists of a carbon chain with four carbon atoms (C4), one oxygen atom (O), and one ethyl group (-C2H5) attached to a vinyl group (-CH=CH2). The structure resembles a linear carbon chain with an oxygen atom in the middle, connected to two carbon groups.
Ethyl Vinyl Ether Solubility
Ethoxyethylene is moderately soluble in water, with a solubility of around 6.2 grams per 100 milliliters at 25 degrees Celsius (77 degrees Fahrenheit). However, it exhibits better solubility in organic solvents such as ethanol and acetone. The solubility of ethoxyethylene is influenced by its polarity and molecular interactions with the solvent molecules.
| Appearance | Colorless liquid |
| Specific Gravity | 0.73 g/mL |
| Color | Colorless |
| Odor | Pleasant |
| Molar Mass | 72.11 g/mol |
| Density | 0.73 g/mL |
| Melting Point | -102 °C |
| Boiling Point | 35-36 °C |
| Flash Point | -20 °C |
| Water Solubility | Moderate |
| Solubility | Soluble in organic solvents like ethanol, acetone |
| Vapour Pressure | 159 mmHg at 25 °C |
| Vapour Density | 2.5 (air = 1) |
| pKa | 12.7 |
| pH | Neutral |
Ethyl Vinyl Ether Safety and Hazards
Ethoxyethylene poses certain safety hazards and should be handled with caution. It is highly flammable, with a flash point of -20 degrees Celsius (-4 degrees Fahrenheit), meaning it can ignite easily. It should be kept away from open flames, sparks, and heat sources. The compound may also cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. Adequate ventilation is necessary to minimize exposure. Ethoxyethylene should be stored in tightly sealed containers away from incompatible substances. It is important to follow proper handling procedures, wear appropriate protective equipment, and consult safety data sheets for comprehensive safety information.
| Hazard Symbols | Flammable (F) |
| Safety Description | Keep away from heat/sparks/open flames. Use in well-ventilated areas. Avoid contact with eyes, skin, and clothing. |
| UN IDs | UN 1151 |
| HS Code | 29091900 |
| Hazard Class | Class 3 – Flammable liquids |
| Packing Group | PG II |
| Toxicity | May cause irritation to the skin, eyes, and respiratory system. Avoid prolonged or repeated exposure. |
Ethyl Vinyl Ether Synthesis Methods
Various methods can synthesize ethoxyethylene. One common approach involves the reaction between ethanol and acetylene in the presence of a strong base catalyst, such as potassium hydroxide (KOH). The reaction proceeds through an elimination process, where the hydroxyl group (-OH) from ethanol combines with a hydrogen atom from the acetylene molecule, forming water. The formation of the vinyl ether bond between the acetylene molecule and the remaining -C2H5 group from ethanol follows this step.
Another method involves the reaction between ethyl alcohol and vinyl acetate in the presence of an acid catalyst, such as sulfuric acid (H2SO4). The acid catalyst helps in the esterification process, where the alcohol and the acid combine to form an ester compound. In this case, the resulting ester undergoes a subsequent thermal decomposition, leading to the formation of ethoxyethylene.
The reaction between ethyl alcohol and acetylene in the presence of a palladium catalyst can prepare ethoxyethylene. This method, known as the Pd-catalyzed coupling reaction, enables the direct conversion of the alcohol and acetylene into the desired vinyl ether.
These synthesis methods provide routes for the production of ethoxyethylene, which finds applications in various industries such as polymer manufacturing, solvents, and chemical intermediates. Proper handling and adherence to safety protocols are essential during the synthesis process due to the flammability and potential hazards associated with ethoxyethylene.
Ethyl Vinyl Ether Uses
Here are some of the common uses of ethoxyethylene due to its unique properties:
- Solvent: Ethoxyethylene serves as a solvent for various organic compounds, particularly in the production of resins, varnishes, and lacquers.
- Polymerization: It acts as a monomer in the synthesis of different polymers, such as poly(vinyl ether) and poly(ethoxyethylene), which find applications in adhesives, coatings, and surface modifiers.
- Chemical Intermediates: It acts as a precursor for synthesizing other compounds. It undergoes various chemical reactions to produce valuable intermediates used in pharmaceuticals, agrochemicals, and fragrance industries.
- Fuel Additive: Industries utilize it as an additive in gasoline to enhance combustion efficiency and reduce emissions.
- Laboratory Reagent: It serves as a reagent in organic synthesis, specifically in preparing vinyl compounds, ethers, and other functionalized organic molecules.
- Flavor and Fragrance: It plays a role in the production of artificial flavors and fragrances, imparting pleasant and desirable odors to various consumer products.
- Chemical Research: It finds application as a reference compound in chemical analysis techniques such as gas chromatography and spectroscopy.
- Extraction Solvent: It serves as a solvent for the extraction of natural products, such as essential oils and flavors.
The versatile nature of ethoxyethylene allows it to contribute to diverse industries, fulfilling roles ranging from solvents and monomers to reagents and additives.
Questions:
Q: Can ethyl vinyl ether conjugate?
A: No, ethoxyethylene does not exhibit conjugation due to the absence of conjugated pi bonds in its structure.
Q: What is the role of ethyl vinyl ether in ROMP reactions?
A: Ethoxyethylene serves as a comonomer in ring-opening metathesis polymerization (ROMP) reactions, participating in the formation of polymers with unique properties and structures.
Q: Ethyl vinyl ether alcohol?
A: Ethoxyethylene does not have an alcohol functional group; it is an ether compound.
Q: Ethyl vinyl ether IR spectrum?
A: The infrared (IR) spectrum of ethoxyethylene typically shows characteristic peaks around 3000-3100 cm^-1 (C-H stretch) and 1600-1650 cm^-1 (C=C stretch).
Q: Ethyl vinyl ether density?
A: The density of ethoxyethylene is approximately 0.73 grams per milliliter (g/mL).
Q: Can ethyl vinyl ether conjugate?
A: No, ethoxyethylene does not exhibit conjugation due to its molecular structure lacking conjugated pi bonds.
Q: Ethyl vinyl ether stability?
A: Ethoxyethylene is relatively stable but should be handled and stored carefully due to its flammability and potential hazards.
Q: Ethyl vinyl ether manufacturers?
A: Ethoxyethylene is produced by various chemical manufacturers and suppliers globally, including companies specializing in fine chemicals and reagents.