Acrylonitrile is a chemical used in the production of plastics and synthetic fibers. It is highly flammable and toxic if ingested or inhaled. Its use requires careful handling and disposal.
| IUPAC name | Prop-2-enenitrile |
| Molecular formula | C3H3N |
| CAS number | 107-13-1 |
| Synonyms | Vinyl cyanide, Cyanoethylene, 2-Propenenitrile |
| InChI | InChI=1S/C3H3N/c1-2-3-4/h2H,1H2 |
Acrylonitrile Properties
Acrylonitrile Formula
The chemical formula for acrylonitrile is C3H3N. It is an unsaturated nitrile compound that contains a carbon-carbon triple bond and a carbon-nitrogen bond. The triple bond makes acrylonitrile highly reactive, which is why it is commonly used in the production of plastics and synthetic fibers.
Acrylonitrile Molar Mass
The molar mass of vinyl cyanide is 53.06 g/mol. This value is calculated by adding up the atomic masses of each element in the chemical formula, which are 36 g/mol for carbon, 1.01 g/mol for hydrogen, and 14.01 g/mol for nitrogen.
Acrylonitrile Boiling Point
Vinyl cyanide has a boiling point of 77.3 °C (171.1 °F). This low boiling point is due to the weak intermolecular forces between the molecules of vinyl cyanide. As a result, it evaporates easily and is highly volatile.
Acrylonitrile Melting Point
The melting point of vinyl cyanide is -84.5 °C (-120.1 °F). This low melting point is due to the weak intermolecular forces between the molecules of vinyl cyanide. As a result, it exists in a liquid state at room temperature.
Acrylonitrile Density g/mL
The density of vinyl cyanide is 0.81 g/mL. This value indicates that vinyl cyanide is less dense than water, which has a density of 1 g/mL. As a result, vinyl cyanide floats on top of water.
Acrylonitrile Molecular Weight
The molecular weight of vinyl cyanide is 53.06 g/mol. This value is calculated by adding up the atomic masses of each element in the chemical formula, which are 36 g/mol for carbon, 1.01 g/mol for hydrogen, and 14.01 g/mol for nitrogen.
Acrylonitrile Structure
Vinyl cyanide has a linear structure, with the carbon-carbon triple bond and carbon-nitrogen bond in the same plane. The triple bond gives vinyl cyanide its high reactivity, which is useful in the production of polymers and other industrial chemicals.
Acrylonitrile Solubility
Vinyl cyanide is only slightly soluble in water, with a solubility of 3.5 g/L at room temperature. It is more soluble in organic solvents such as ethanol, acetone, and benzene. This solubility behavior is due to the polarity of the vinyl cyanide molecule, which makes it more compatible with other non-polar solvents.
| Appearance | Colorless liquid |
| Specific Gravity | 0.81 g/mL |
| Color | Colorless |
| Odor | Faintly sweet |
| Molar Mass | 53.06 g/mol |
| Density | 0.81 g/mL |
| Melting Point | -84.5 °C (-120.1 °F) |
| Boiling Point | 77.3 °C (171.1 °F) |
| Flash Point | -4 °C (25 °F) |
| Water Solubility | 3.5 g/L |
| Solubility | Soluble in organic solvents |
| Vapour Pressure | 82.6 kPa at 25 °C |
| Vapour Density | 1.82 (air = 1) |
| pKa | 2.98 |
| pH | 7 (neutral) |
Acrylonitrile Safety and Hazards
Vinyl cyanide is a highly flammable and toxic substance. Its fumes can irritate the respiratory system, skin, and eyes, and prolonged exposure can cause serious health problems. Vinyl cyanide vapors can also cause headaches, nausea, and dizziness. In addition, vinyl cyanide is a known carcinogen and can cause cancer in humans. Proper safety precautions must be taken when handling vinyl cyanide, including the use of personal protective equipment such as gloves, goggles, and respirators. It is also important to store vinyl cyanide in a well-ventilated area away from sources of ignition and to dispose of it properly to prevent contamination of the environment.
| Hazard Symbols | T, F, N |
| Safety Description | Highly flammable and toxic |
| UN IDs | UN 1648 |
| HS Code | 2926.10.00 |
| Hazard Class | 3 – Flammable liquid |
| Packing Group | II – Medium danger |
| Toxicity | Highly toxic, carcinogenic |
Acrylonitrile Synthesis Methods
The most commonly used process for producing vinyl cyanide is by ammoxidation of propylene. This process involves reacting propylene with ammonia and air using a catalyst. The reaction occurs at high temperatures and pressures and produces a mixture of vinyl cyanide, hydrogen cyanide, and water. The process involves separating and purifying the mixture to obtain pure vinyl cyanide.
Another method for producing vinyl cyanide is the oxidation of propylene with hydrogen cyanide. This process produces a mixture of vinyl cyanide and acetonitrile, which can be separated by distillation. The high toxicity of hydrogen cyanide makes it less common to use this method.
Vinyl cyanide can also be synthesized by the ammoxidation of ethylene, but this method is less efficient than the propylene process. The process involves using a catalyst to react with ethylene, ammonia, and air, which results in the production of vinyl cyanide and water.
Acrylonitrile Uses
Vinyl cyanide has a variety of uses across several industries, including:
- Production of synthetic fibers: Vinyl cyanide is a key raw material for the production of synthetic fibers such as acrylic, modacrylic, and carbon fibers.
- Manufacturing of plastics: The production of plastics like ABS (vinyl cyanide-butadiene-styrene), widely used in the automotive and electronics industries, utilizes vinyl cyanide.
- Production of nitrile rubber: Producers use vinyl cyanide as a significant element in manufacturing nitrile rubber, a versatile material utilized in various applications such as gloves, gaskets, seals, and hoses.
- Manufacturing of resins and adhesives: Manufacturers use vinyl cyanide to produce resins and adhesives for different purposes, including coatings, laminates, and composites.
- Chemical intermediates: Vinyl cyanide serves as a chemical intermediate for the production of various chemicals, such as adiponitrile, acrylamide, and methvinyl cyanide.
- Agricultural chemicals: Several agricultural chemicals, including herbicides, insecticides, and fungicides, use vinyl cyanide as a raw material in their production.
Questions:
Q: How many pi bonds are there in one molecule of acrylonitrile?
A: There are two pi bonds in one molecule of vinyl cyanide.
Q: Where is acrylonitrile made?
A: Vinyl cyanide is primarily made through the ammoxidation of propylene, which is a process that takes place in industrial plants.
Q: Which artificial nail products are made from acrylonitrile butadiene styrene?
A: Acrylonitrile butadiene styrene (ABS) is a common material used in the production of artificial nail tips and overlays.
Q: How many pi bonds are there in one molecule of acrylonitrile?
A: There are two pi bonds in one molecule of vinyl cyanide.
Q: What fiber is a polymer of acrylonitrile?
A: Acrylic fiber is a polymer of vinyl cyanide and is commonly used in the production of clothing and textiles.
Q: What is acrylonitrile butadiene styrene?
A: Acrylonitrile butadiene styrene (ABS) is a thermoplastic polymer that is commonly used in the production of various products such as toys, automotive parts, and household appliances.