Ethyl acrylate (C₅H₈O₂) is a chemical compound used in the production of adhesives and coatings. It has a distinct fruity odor and can cause irritation to the skin and eyes.
| IUPAC Name | Ethyl propenoate |
| Molecular Formula | C₅H₈O₂ |
| CAS Number | 140-88-5 |
| Synonyms | Ethyl 2-propenoate, Ethyl prop-2-enoate, Acrylic acid ethyl ester |
| InChI | InChI=1S/C5H8O2/c1-3-6-5(7)4-2/h3-4H2,1-2H3 |
Ethyl Acrylate Properties
Ethyl Acrylate Formula
The formula of ethyl acrylate is C₅H₈O₂. It consists of five carbon atoms, eight hydrogen atoms, and two oxygen atoms. The formula represents the arrangement and number of atoms in a molecule of ethyl acrylate.
Ethyl Acrylate Molar Mass
The molar mass of ethyl propenoate is calculated by adding the atomic masses of its constituent elements. Ethyl propenoate has a molar mass of approximately 100.12 grams per mole. This value is useful in determining the amount of ethyl propenoate present in a given quantity.
Ethyl Acrylate Boiling Point
The boiling point of ethyl propenoate is an important physical property. It is the temperature at which ethyl propenoate changes from a liquid to a gas phase. Ethyl propenoate has a boiling point of around 99-101 degrees Celsius (210-214 degrees Fahrenheit).
Ethyl Acrylate Melting Point
The melting point of ethyl propenoate is another significant characteristic. It is the temperature at which ethyl propenoate changes from a solid to a liquid state. Ethyl propenoate has a relatively low melting point of approximately -71 degrees Celsius (-96 degrees Fahrenheit).
Ethyl Acrylate Density g/mL
The density of ethyl propenoate is a measure of its mass per unit volume. Ethyl propenoate has a density of about 0.954 grams per milliliter (g/mL) at 20 degrees Celsius (68 degrees Fahrenheit). This property is essential for understanding its behavior in different conditions.
Ethyl Acrylate Molecular Weight
The molecular weight of ethyl propenoate is the sum of the atomic weights of all the atoms in its chemical formula. Ethyl propenoate has a molecular weight of approximately 100.12 grams per mole. This value helps in various calculations involving the substance.
Ethyl Acrylate Structure
The structure of ethyl propenoate consists of a chain of five carbon atoms bonded together. One carbon atom is double-bonded to an oxygen atom, and another carbon atom is bonded to an ethyl group (C₂H₅). This structure gives ethyl propenoate its unique chemical properties.
Ethyl Acrylate Solubility
Ethyl propenoate is sparingly soluble in water but dissolves readily in organic solvents like ethanol and acetone. Its solubility in water is influenced by factors such as temperature and the presence of other substances. Understanding its solubility aids in its application and handling.
| Appearance | Colorless liquid |
| Specific Gravity | 0.954 g/mL |
| Color | Colorless |
| Odor | Fruity |
| Molar Mass | 100.12 g/mol |
| Density | 0.954 g/mL |
| Melting Point | -71 °C (-96 °F) |
| Boiling Point | 99-101 °C (210-214 °F) |
| Flash Point | 13 °C (55 °F) |
| Water Solubility | Slightly soluble |
| Solubility | Soluble in organic solvents |
| Vapour Pressure | 29 mmHg (at 20 °C) |
| Vapour Density | 3.5 (air = 1) |
| pKa | 4.53 |
| pH | Approximately 6-7 |
Ethyl Acrylate Safety and Hazards
Ethyl propenoate poses certain safety hazards that need to be considered. It is important to handle this substance with caution. Ethyl propenoate is flammable and can form explosive vapor-air mixtures. It is also an irritant to the skin, eyes, and respiratory system. Prolonged or repeated exposure may lead to dermatitis or respiratory sensitization. In case of contact, immediate rinsing with plenty of water is advised. Adequate ventilation is necessary when working with ethyl propenoate to prevent the buildup of vapors. Proper personal protective equipment, such as gloves and safety goggles, should be worn to minimize the risk of exposure.
| Hazard Symbols | Flammable, Irritant |
| Safety Description | Keep away from heat/sparks/open flames/hot surfaces. Avoid breathing dust/fume/gas/mist/vapors/spray. Wear protective gloves/eye protection/face protection. IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
| UN IDs | UN 1917 (for Ethyl Acrylate) |
| HS Code | 2916.11.00 |
| Hazard Class | Class 3 (Flammable Liquid) |
| Packing Group | PG II (Intermediate Packaging) |
| Toxicity | May cause skin and eye irritation; prolonged exposure may cause dermatitis or respiratory sensitization. Avoid ingestion or inhalation. Seek medical attention if symptoms persist. |
Ethyl Acrylate Synthesis Methods
Different methods can synthesize ethyl propenoate.
One common method is the esterification reaction between acrylic acid and ethanol. In this process, acrylic acid reacts with ethanol in the presence of a catalyst, such as sulfuric acid or p-toluenesulfonic acid. The reaction takes place under reflux conditions, with continuous removal of the water formed as a byproduct. This allows the reaction to proceed toward the formation of ethyl propenoate.
Another synthesis method involves the transesterification of methyl propenoate with ethanol. In this reaction, methyl propenoate reacts with ethanol in the presence of a base catalyst, such as sodium or potassium hydroxide. The transesterification process leads to the formation of ethyl propenoate and methanol as a byproduct. Typically, the reaction occurs at elevated temperatures, and operators separate and purify the product afterward.
An acid catalyst, such as p-toluenesulfonic acid, enables the direct esterification of acrylic acid with ethanol to produce ethyl propenoate. The reaction proceeds under controlled conditions to promote the formation of ethyl propenoate and minimize the generation of undesired byproducts.
These synthesis methods provide routes for the production of ethyl propenoate on an industrial scale. However, it is important to note that one should carry out these reactions with proper safety precautions and under suitable conditions to ensure the desired yield and purity of the final product.
Ethyl Acrylate Uses
Ethyl propenoate finds various applications across different industries. Here are some of its uses:
- Adhesive and Sealant Manufacturing: Ethyl propenoate is a key ingredient in the production of adhesives and sealants. It contributes to their ability to bond with different materials, such as metals, plastics, and wood.
- Coatings and Paints: In the formulation of coatings and paints, manufacturers utilize ethyl propenoate. It enhances their durability, adhesion, and weather resistance properties. One applies these coatings actively to surfaces such as automobiles, buildings, and furniture.
- Textile Finishing: Textile finishing processes employ ethyl propenoate. It helps improve the fabric’s wrinkle resistance, stiffness, and durability.
- Polymer Manufacturing: Manufacturers use ethyl propenoate as a monomer in polymer production. It serves as a building block for various copolymers, including ethyl propenoate-butyl acrylate copolymers. These copolymers exhibit desirable properties such as flexibility and impact resistance.
- Emulsion Polymers: Manufacturers utilize ethyl propenoate in the production of emulsion polymers, which have applications in paints, coatings, and adhesives. Emulsion polymers offer excellent film-forming properties and stability.
- Plastic Additives: Plastic manufacturers can use ethyl propenoate as an additive to actively enhance the flexibility and impact resistance of their products. It improves the overall performance and processing characteristics of the plastic material.
- Paper Coatings: Paper coatings employ ethyl propenoate to enhance their smoothness, printability, and resistance to moisture and oil.
- Leather Treatment: Manufacturers use ethyl propenoate to treat leather, enhancing its durability, water resistance, and flexibility.
The diverse range of applications of ethyl propenoate demonstrates its versatility and importance in various industries.
Questions:
Q: Who uses ethyl acrylate?
A: Industries such as adhesive, coatings, paints, textile, polymer, and plastic manufacturers utilize ethyl propenoate in their processes.
Q: Is ethyl acrylate in Invisalign?
A: Ethyl propenoate is not a component of Invisalign aligners. Invisalign aligners are made from a proprietary thermoplastic material known as SmartTrack, which does not contain ethyl propenoate.
Q: What contains ethyl acrylate?
A: Ethyl propenoate is found in products such as adhesives, coatings, paints, textile finishes, emulsion polymers, and plastic additives due to its versatile properties.
Q: Are ethyl acetate, butyl acetate, acrylates copolymer, like nitrocellulose?
A: Ethyl acetate, butyl acetate, and acrylates copolymer are different substances from nitrocellulose. They have distinct chemical compositions and properties.
Q: Will ethyl acetate corrode acrylic?
A: No, ethyl acetate does not corrode acrylic. It is generally compatible with acrylic materials and is commonly used as a solvent in acrylic-based products.