Chloroprene (C4H5Cl) is a synthetic compound used in the production of neoprene, a versatile material with applications in wetsuits, gaskets, and industrial coatings.
| IUPAC Name | 2-chlorobuta-1,3-diene |
| Molecular Formula | C4H5Cl |
| CAS Number | 126-99-8 |
| Synonyms | 1-chloro-2,3-butadiene, chlorobutadiene, 2-chloro-1,3-butadiene |
| InChI | InChI=1S/C4H5Cl/c1-2-3-4-5/h2-4H,1H2 |
Chloroprene Properties
Chloroprene Formula
The formula of chloroprene is C4H5Cl. It consists of four carbon atoms, five hydrogen atoms, and one chlorine atom. This chemical structure gives chloroprene its unique properties and applications in various industries.
Chloroprene Molar Mass
The molar mass of chlorobutadiene is calculated by adding the atomic masses of each element in its formula. The molar mass of chlorobutadiene is approximately 88.53 grams per mole (g/mol). This value is crucial for determining the amount of chlorobutadiene needed in chemical reactions.
Chloroprene Boiling Point
Chlorobutadiene has a boiling point of around 59 degrees Celsius (138 degrees Fahrenheit). This temperature represents the point at which chlorobutadiene changes from a liquid to a gaseous state when heated. The boiling point is significant in industrial processes that require the conversion of chlorobutadiene into its gaseous form.
Chloroprene Melting Point
Chlorobutadiene has a melting point of approximately -135 degrees Celsius (-211 degrees Fahrenheit). This temperature is the point at which solid chlorobutadiene transforms into a liquid state upon heating. The melting point is important in manufacturing processes where chlorobutadiene needs to be melted and shaped into various forms.
Chloroprene Density g/mL
Chlorobutadiene has a density of about 1.16 grams per milliliter (g/mL). Density is the measure of mass per unit volume and provides information about the compactness of a substance. The density of chlorobutadiene is utilized in calculating the volume and weight of chlorobutadiene needed for specific applications.
Chloroprene Molecular Weight
The molecular weight of chlorobutadiene is approximately 88.53 grams per mole (g/mol). It is the sum of the atomic weights of all the atoms in a chlorobutadiene molecule. The molecular weight is crucial for understanding the compound’s behavior, such as its reactivity and interactions with other substances.
Chloroprene Structure
Chlorobutadiene has a structure consisting of four carbon atoms bonded together in a chain, with a chlorine atom and two double bonds attached to the second carbon atom. This arrangement gives chlorobutadiene its characteristic properties, such as its resistance to heat, chemicals, and weathering.
Chloroprene Solubility
Chlorobutadiene is sparingly soluble in water but dissolves well in organic solvents such as acetone and benzene. Its solubility characteristics make it suitable for various applications, including coatings, adhesives, and synthetic rubber production. Understanding its solubility helps in determining its compatibility with different solvents and solvent-based processes.
| Appearance | Colorless liquid |
| Specific Gravity | 1.16 |
| Color | Colorless |
| Odor | Mild, characteristic |
| Molar Mass | 88.53 g/mol |
| Density | 1.16 g/mL |
| Melting Point | -135 °C (-211 °F) |
| Boiling Point | 59 °C (138 °F) |
| Flash Point | -17 °C (1 °F) |
| Water Solubility | Sparingly soluble |
| Solubility | Soluble in organic solvents |
| Vapor Pressure | 250 mmHg at 20 °C |
| Vapor Density | 3.08 (air = 1) |
| pKa | ~ 7.4 |
| pH | Neutral |
Chloroprene Safety and Hazards
Chlorobutadiene poses certain safety hazards that need to be considered. It is important to handle chlorobutadiene with caution and follow proper safety measures. Direct contact with chlorobutadiene may cause skin and eye irritation, so protective equipment such as gloves and goggles should be worn. Inhaling chlorobutadiene vapors can irritate the respiratory system, necessitating the use of proper ventilation. Chlorobutadiene is flammable and can form explosive mixtures with air, so it should be stored and handled away from open flames and sources of ignition. It is also crucial to dispose of chlorobutadiene waste in accordance with proper regulations to prevent environmental contamination.
| Hazard Symbols | Flammable, Irritant, Health Hazard |
| Safety Description | Flammable liquid. Harmful if swallowed or inhaled. Causes skin and eye irritation. Handle with caution. Use proper ventilation and personal protective equipment. Store away from ignition sources. Dispose of waste properly. |
| UN IDs | UN 1991 |
| HS Code | 2902.41.0000 |
| Hazard Class | Class 3 (Flammable liquids) |
| Packing Group | PG II |
| Toxicity | Moderately toxic |
Chloroprene Synthesis Methods
The chlorination of 1,3-butadiene, a colorless gas obtained from petroleum processing, is the primary method for synthesizing chlorobutadiene. This reaction, which takes place at temperatures ranging from 20-50 °C, involves the substitution of chlorine atoms for hydrogen atoms on the butadiene molecule. Typically, researchers use catalysts like iron or aluminum chloride to facilitate the reaction. The outcome of this process is the formation of chlorobutadiene.
The pyrolysis of isoprene, a liquid monomer obtained through the processing of natural rubber, is another method for synthesizing chlorobutadiene. This process involves heating isoprene to high temperatures, typically above 600 °C, in the presence of a catalyst, such as aluminum chloride or boron trifluoride. The heat and catalyst cause the isoprene molecules to break down, leading to the formation of chlorobutadiene.
Overall, the chlorination of butadiene remains the most commonly used method for synthesizing chlorobutadiene due to its cost-effectiveness and efficiency. However, both methods require careful handling and the use of proper safety measures due to the hazardous nature of the chemicals involved.
Chloroprene Uses
Chlorobutadiene has various applications across different industries due to its unique properties. Here are some of its uses:
- Neoprene Production: Chlorobutadiene is a key ingredient in the manufacturing of neoprene, a versatile synthetic rubber. Wetsuits, gloves, footwear, and other water-resistant products extensively utilize neoprene.
- Industrial Coatings: Chlorobutadiene-based coatings provide excellent resistance to chemicals, oils, and weathering. Applications such as tank linings, conveyor belts, and automotive components utilize these coatings.
- Adhesives and Sealants: Chlorobutadiene-based adhesives and sealants offer strong bonding properties and flexibility. The construction, automotive, and aerospace industries commonly use them to bond various materials.
- Electrical Insulation: The production of cables, wires, and connectors utilizes chlorobutadiene due to its electrical insulation properties. It provides protection against moisture, heat, and mechanical stress.
- Gaskets and O-rings: Chlorobutadiene’s resilience and resistance to chemicals make it suitable for manufacturing gaskets and O-rings used in mechanical and automotive applications.
- Belts and Hoses: Manufacturers employ chlorobutadiene in the production of belts and hoses due to its resistance to abrasion, heat, and oils, which ensures durability and reliability.
- Sports and Recreation: Chlorobutadiene-based materials find use in sporting goods such as gloves, diving suits, and protective gear, offering comfort, flexibility, and water resistance.
- Marine Applications: Chlorobutadiene’s resistance to saltwater and weathering makes it ideal for marine applications like boat fenders, dock bumpers, and underwater structures.
- Medical Products: Chlorobutadiene gloves and surgical products provide a barrier against contaminants, making them valuable in healthcare settings.
Chlorobutadiene’s versatility and desirable properties contribute to its widespread use in diverse industries, addressing a range of applications and requirements.
Questions:
Q: What is chloroprene?
A: Chlorobutadiene is a synthetic compound used in the production of neoprene, a versatile material with applications in various industries such as rubber manufacturing, coatings, and adhesives.
Q: Does chloroprene cause cancer?
A: Prolonged exposure to chlorobutadiene has been associated with an increased risk of certain cancers, including lung and liver cancer, based on studies conducted on animals. Human studies are limited but suggest a potential carcinogenic effect.
Q: What is chloroprene used for?
A: Chlorobutadiene is used in the production of neoprene, which is then utilized in products like wetsuits, gaskets, adhesives, coatings, electrical insulation, and various other applications requiring its unique properties.
Q: What is chloroprene rubber?
A: Chloroprene rubber, also known as polychloroprene or CR, is a type of synthetic rubber derived from chloroprene. It possesses excellent resistance to heat, chemicals, and weathering, making it suitable for various industrial applications.
Q: Where are chloroprene plants in the US?
A: Chlorobutadiene plants in the US are located in Pontchartrain Works, Louisiana, operated by Denka Performance Elastomer LLC.
Q: Is chloroprene biodegradable?
A: Chlorobutadiene is not readily biodegradable, and its breakdown in the environment is slow. It can persist for an extended period and potentially impact ecosystems.
Q: What is chloroprene rubber used for?
A: Chloroprene rubber is used in the production of products such as hoses, belts, cables, gaskets, O-rings, and other applications requiring durability, flexibility, and resistance to chemicals and oils.
Q: How to change chloroprene to polychloroprene?
A: Chlorobutadiene can be polymerized to form polychloroprene (CR) through a process called free-radical polymerization, which involves the use of initiators and suitable reaction conditions.
Q: Where to buy giant chloroprene balloons?
A: Giant chlorobutadiene balloons can be purchased from various party supply stores, online retailers, or specialized balloon suppliers.