Caprolactam (C₆H₁₁NO) is a chemical compound used in the production of nylon. It is obtained through the process of cyclohexanone oxidation and plays a crucial role in the textile industry.
| IUPAC Name | Azepan-2-one |
| Molecular Formula | C₆H₁₁NO |
| CAS Number | 105-60-2 |
| Synonyms | Hexahydro-2H-azepin-2-one, Caproic lactam, Cyclohexanelactam |
| InChI | InChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8) |
Caprolactam Properties
Caprolactam Formula
The formula for caprolactam is C₆H₁₁NO. It consists of six carbon atoms, eleven hydrogen atoms, one nitrogen atom, and one oxygen atom. This formula represents the arrangement of atoms in a molecule of caprolactam.
Caprolactam Molar Mass
The molar mass of caproic lactam is calculated by adding up the atomic masses of all the atoms in its formula. In the case of caproic lactam (C₆H₁₁NO), the molar mass is approximately 113.16 grams per mole.
Caprolactam Boiling Point
Caproic lactam has a boiling point of around 270 degrees Celsius. This is the temperature at which caproic lactam undergoes a phase transition from a liquid to a gas. The boiling point of caproic lactam determines its volatility and plays a significant role in industrial processes involving this compound.
Caprolactam Melting Point
The melting point of caproic lactam is approximately 68.5 degrees Celsius. This is the temperature at which caproic lactam changes its state from a solid to a liquid. The melting point is an important characteristic that affects its handling and processing in various applications.
Caprolactam Density g/ml
Caproic lactam has a density of about 1.03 grams per milliliter. Density is a measure of how much mass is packed within a given volume. The density of caproic lactam is an essential property for determining its behavior in different solutions and mixtures.
Caprolactam Molecular Weight
The molecular weight of caproic lactam is approximately 113.16 grams per mole. It is the sum of the atomic weights of all the atoms in a molecule of caproic lactam. Molecular weight is a crucial factor in calculating concentrations and determining the amount of caproic lactam needed in various chemical processes.
Caprolactam Structure
Caproic lactam has a cyclic structure consisting of a six-membered ring with alternating carbon and nitrogen atoms, along with an attached carbonyl group. This unique structure gives caproic lactam its characteristic properties and makes it a versatile compound for applications in industries such as textiles and plastics.
Caprolactam Solubility
Caproic lactam is sparingly soluble in water, with a solubility of approximately 2.5 grams per liter at room temperature. However, it is more soluble in organic solvents like ethanol and acetone. The solubility of caproic lactam determines its behavior when mixed with other substances and plays a role in various manufacturing processes.
| Appearance | Colorless crystals |
| Specific Gravity | 1.03 g/cm³ |
| Color | Colorless |
| Odor | Mild odor |
| Molar Mass | 113.16 g/mol |
| Density | 1.03 g/cm³ |
| Melting Point | 68.5 °C |
| Boiling Point | 270 °C |
| Flash Point | 150 °C |
| Water Solubility | 240 g/L |
| Solubility | Soluble in organic solvents like ethanol, acetone |
| Vapour Pressure | 0.11 mmHg at 25 °C |
| Vapour Density | 3.92 (air = 1) |
| pKa | 13.6 |
| pH | 5.0 – 7.0 |
Caprolactum Safety and Hazards
Caproic lactam poses certain safety hazards that must be taken into consideration. It is important to handle caproic lactam with care and adhere to proper safety measures. Contact with caproic lactam may cause skin and eye irritation, so protective gloves and goggles should be worn. Inhalation of caproic lactam vapors can lead to respiratory irritation, so adequate ventilation is necessary. In case of ingestion, immediate medical attention is required. Caproic lactam is combustible and can release toxic fumes when heated. Therefore, it should be stored away from ignition sources and incompatible substances. Proper handling, storage, and disposal procedures must be followed to minimize the risks associated with caproic lactam.
| Hazard Symbols | Irritant |
| Safety Description | May cause skin and eye irritation. |
| UN IDs | UN 2920 |
| HS Code | 2933.79.90 |
| Hazard Class | 6.1 (Toxic substances) |
| Packing Group | III |
| Toxicity | Moderate to low toxicity |
Caprolactum Synthesis Methods
Various methods can synthesize caproic lactam.
One common method is the Beckmann rearrangement. In this process, a strong acid, such as sulfuric acid, reacts with cyclohexanone oxime and produces caproic lactam. The reaction proceeds through the formation of an intermediate, which rearranges to form caproic lactam.
Another method involves the catalytic hydrogenation of phenol. Phenol is first converted to cyclohexanone through a series of reactions. A strong acid, such as sulfuric acid, reacts with cyclohexanone oxime to produce caproic lactam.
In a two-step process, cyclohexane can synthesize caproic lactam. The first step involves the oxidation of cyclohexane to produce cyclohexanol, followed by the oxidation of cyclohexanol to yield cyclohexanone. Ammonia treats cyclohexanone under high temperature and pressure conditions, resulting in the formation of caproic lactam.
The oxidation of cyclohexane produces adipic acid, which synthesizes caproic lactam. Adipic acid is first converted to its corresponding diamide, which is then cyclized to produce caproic lactam.
These synthesis methods highlight the versatility of caproic lactam production, allowing for different starting materials and reaction pathways. The choice of synthesis method depends on factors such as cost, availability of raw materials, and desired purity of the final product.
Caprolactum Uses
Caproic lactam has various applications across industries. Here are some of its uses:
- Nylon Production: Caproic lactam, a key raw material, heavily contributes to the production of nylon-6, which finds wide applications in textiles, carpets, and industrial fibers.
- Engineering Plastics: Caproic lactam plays a crucial role in manufacturing high-performance engineering plastics, such as nylon resins, which have applications in automotive components, electrical connectors, and consumer goods.
- Films and Coatings: Caproic lactam plays a crucial role in producing films and coatings that provide durability and abrasion resistance. Industries utilize these films in packaging, protective coatings, and laminates.
- Synthetic Fibers: Caproic lactam contributes to the production of synthetic fibers other than nylon, such as polyurethane elastane fibers used in textiles, sports apparel, and swimwear.
- Adhesives and Sealants: Caproic lactam enables the formulation of adhesives and sealants, offering strong bonding properties and flexibility.
- Wire and Cable Coatings: Caproic lactam coats wires and cables to provide protection against moisture, chemicals, and abrasion.
- Industrial Applications: Caproic lactam finds use in various industrial applications, including as a solvent for dyes, pigments, and pharmaceutical intermediates.
- Agricultural Industry: Caproic lactam stabilizes pesticides and herbicides, ensuring their efficacy and prolonging their shelf life.
- Additives and Modifiers: Caproic lactam enhances properties such as flame resistance, impact resistance, and thermal stability, serving as an additive or modifier in various industries.
- Research and Development: Caproic lactam serves as a starting material for chemical synthesis, enabling the development of new compounds and materials.
These diverse applications showcase the significance of caproic lactam across multiple industries, highlighting its versatility and wide-ranging utility.
Questions:
Q: What is caprolactam?
A: Caproic lactam is a chemical compound used in the production of nylon and other synthetic fibers, as well as in the manufacturing of various plastics and coatings.
Q: How to dispose of caprolactam?
A: Caproic lactam should be disposed of in accordance with local regulations, usually through authorized hazardous waste disposal facilities or methods recommended by environmental agencies.
Q: Is caprolactam a regulated air pollutant?
A: No, caproic lactam is not generally regulated as an air pollutant, but emissions from its production or industrial processes should still be managed within applicable environmental regulations.
Q: Is caprolactam a HAP?
A: No, caproic lactam is not considered a Hazardous Air Pollutant (HAP) as designated by the U.S. Environmental Protection Agency (EPA) or other regulatory bodies.
Q: Do caprolactams occur naturally?
A: No, caproic lactams are synthetic compounds and do not occur naturally.
Q: Is caprolactam used in manufacturing polyester fiber?
A: No, caproic lactam is not used in the manufacturing of polyester fiber. It is primarily utilized in the production of nylon and other synthetic fibers.
Q: Is caprolactam flammable?
A: Yes, caproic lactam is flammable and can ignite when exposed to a flame or ignition source.
Q: Does caprolactam off-gas?
A: Caproic lactam can release volatile organic compounds (VOCs) and emissions during its production and certain industrial processes, which should be managed and controlled to minimize environmental impact.