Cyclohexanone is a colorless liquid used as a solvent and in the production of nylon and other chemicals. It has a distinct ketone odor.
| IUPAC Name | Cyclohexanone |
| Molecular Formula | C6H10O |
| CAS Number | 108-94-1 |
| Synonyms | Anone, Pimelic ketone, Ketohexamethylene, Cyclohexyl ketone |
| InChI | InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2 |
Cyclohexanone Properties
Cyclohexanone Formula
The formula of cyclohexyl ketone is C6H10O. It consists of six carbon atoms, ten hydrogen atoms, and one oxygen atom. This chemical formula represents the composition of cyclohexyl ketone at the atomic level.
Cyclohexanone Molar Mass
The molar mass of cyclohexyl ketone is calculated by summing up the atomic masses of its constituent elements. It is approximately 98.15 grams per mole. Molar mass provides valuable information about the quantity of substance in a given sample.
Cyclohexanone Boiling Point
Cyclohexyl ketone has a boiling point of around 155 degrees Celsius. This indicates the temperature at which the liquid cyclohexyl ketone changes into its gaseous state. The boiling point is an essential property in various industrial processes and applications.
Cyclohexanone Melting Point
The melting point of cyclohexyl ketone is approximately -30 degrees Celsius. It represents the temperature at which the solid form of cyclohexyl ketone transitions into a liquid state. The melting point is crucial for determining the physical behavior of the substance.
Cyclohexanone Density g/mL
The density of cyclohexyl ketone is around 0.947 grams per milliliter. Density is a measure of the mass per unit volume of a substance. It provides information about how compactly the molecules are packed together in a given volume.
Cyclohexanone Molecular Weight
The molecular weight of cyclohexyl ketone is roughly 98.15 grams per mole. It represents the sum of the atomic weights of all the atoms in one molecule of cyclohexyl ketone. Molecular weight is significant for various calculations and reactions involving the substance.
Cyclohexanone Structure
Cyclohexyl ketone has a cyclic structure consisting of a six-membered carbon ring with an oxygen atom attached. This structure is also known as a ketone functional group. It plays a vital role in determining the chemical and physical properties of cyclohexyl ketone.
Cyclohexanone Solubility
Cyclohexyl ketone is soluble in a wide range of organic solvents, such as ethanol, ether, and chloroform. However, it has limited solubility in water. Solubility is a crucial factor in determining the applicability of cyclohexyl ketone in different chemical processes and formulations.
| Appearance | Colorless liquid |
| Specific Gravity | 0.947 g/mL |
| Color | Colorless |
| Odor | Distinct ketone odor |
| Molar Mass | 98.15 g/mol |
| Density | 0.947 g/mL |
| Melting Point | -30 °C |
| Boiling Point | 155 °C |
| Flash Point | 46 °C |
| Water Solubility | 68 g/L at 25 °C |
| Solubility | Soluble in organic solvents such as ethanol, ether, and chloroform |
| Vapor Pressure | 11 mmHg at 25 °C |
| Vapor Density | 3.35 (Air = 1) |
| pKa | 19.15 (at 25 °C) |
| pH | Neutral (7) |
Cyclohexanone Safety and Hazards
Cyclohexyl ketone poses certain safety hazards that need to be considered. It is a flammable liquid with a flash point of 46 °C, requiring caution when handling or storing it. It can cause eye and skin irritation upon contact, so proper personal protective equipment is recommended. Inhalation of its vapors can lead to respiratory discomfort. Moreover, cyclohexyl ketone should not be ingested as it may cause harmful effects. It is crucial to work with cyclohexyl ketone in well-ventilated areas and to avoid prolonged exposure. Proper storage, handling, and disposal procedures must be followed to ensure the safety of individuals and the environment.
| Hazard Symbols | Flammable, Irritant |
| Safety Description | Keep away from open flames and heat sources. Avoid contact with eyes and skin. Use in well-ventilated areas. Handle with appropriate protective equipment. Store and dispose of properly. |
| UN IDs | UN 1915 |
| HS Code | 29142200 |
| Hazard Class | 3 (Flammable Liquid) |
| Packing Group | III |
| Toxicity | Cyclohexanone is harmful if swallowed and can cause skin and eye irritation. Inhalation of vapors may cause respiratory discomfort. Proper precautions should be taken to minimize exposure. |
Cyclohexanone Synthesis Methods
Various methods synthesize cyclohexyl ketone, including the oxidation of cyclohexane. This process involves reacting cyclohexane with oxygen in the presence of a catalyst, such as platinum or palladium, at elevated temperatures. The oxidation reaction converts cyclohexane into cyclohexanol, which further undergoes oxidation to form cyclohexyl ketone using a strong oxidizing agent like potassium permanganate.
Another method entails the hydrogenation of phenol. This process involves subjecting phenol to hydrogenation under high pressure and temperature conditions, utilizing a metal catalyst such as nickel or palladium. The hydrogenation process transforms phenol into cyclohexyl ketone.
Furthermore, cyclohexyl ketone can be obtained through the oxidation of cyclohexanol. The oxidation of cyclohexanol involves using a mild oxidizing agent such as sodium hypochlorite or chromic acid to oxidize cyclohexanol and generate cyclohexyl ketone.
Furthermore, there are methods that involve the use of more specialized reagents. For example, the oxidation of cyclohexene with air or oxygen in the presence of a catalyst can yield cyclohexyl ketone. Alternatively, the reaction of adipic acid with hydrogen peroxide in the presence of a catalyst can also produce cyclohexyl ketone.
These various synthesis methods offer different routes for the production of cyclohexyl ketone, allowing for flexibility in industrial applications and research purposes. The choice of method depends on factors such as the availability of starting materials, reaction conditions, and desired purity of the final product.
Cyclohexanone Uses
Cyclohexyl ketone finds numerous applications in various industries due to its versatile properties. Here are some common uses of cyclohexyl ketone:
- Solvent: Cyclohexyl ketone serves as a solvent for a wide range of substances, including resins, waxes, oils, and cellulose ethers. It is particularly useful in the production of coatings, adhesives, and dyes.
- Nylon Production: Cyclohexyl ketone is a key intermediate in the production of nylon-6. It undergoes a reaction with adipic acid to form adipic ester, which is then polymerized to create nylon-6 fibers and plastics.
- Paint and Varnish Remover: Due to its strong solvent properties, cyclohexyl ketone is utilized in paint and varnish removers. It effectively dissolves and removes various types of coatings.
- Pharmaceutical Manufacturing: Cyclohexyl ketone serves as a starting material in the synthesis of several pharmaceuticals and drug intermediates. It plays a crucial role in the production of medications for pain relief, antibiotics, and other therapeutic agents.
- Rubber Industry: Cyclohexyl ketone is used in the rubber industry as a processing aid and accelerator. It enhances the elasticity, durability, and resistance properties of rubber compounds.
- Chemical Reagent: It acts as a reagent in various organic synthesis reactions, including the production of cyclohexanol, cyclohexene, and adipic acid. It is also employed in the preparation of other organic compounds.
- Fragrance and Flavor Industry: Cyclohexyl ketone is utilized in the creation of fragrances and flavors due to its characteristic ketone odor. It imparts a pleasant scent and taste to a variety of consumer products.
The diverse applications of cyclohexyl ketone make it an important chemical in numerous industries, contributing to the production of various consumer goods, materials, and pharmaceuticals.
Questions:
Q: Is cyclohexanone flammable?
A: Yes, cyclohexyl ketone is flammable.
Q: What is cyclohexanone used for?
A: Cyclohexyl ketone is used as a solvent, in nylon production, as a paint remover, in pharmaceutical manufacturing, and in the rubber industry, among other applications.
Q: How much cyclohexanone should I get from cyclohexanol?
A: The conversion of cyclohexanol to cyclohexyl ketone is typically complete, resulting in a theoretical yield of nearly 100%.
Q: How is cyclohexanone made?
A: Cyclohexyl ketone can be produced through various methods, such as the oxidation of cyclohexane, hydrogenation of phenol, or oxidation of cyclohexanol.
Q: Is cyclohexanone an electrolyte?
A: No, cyclohexyl ketone is not an electrolyte as it does not dissociate into ions in solution.
Q: Starting with cyclohexanone, how could you prepare the diketone below?
A: The diketone can be prepared by treating cyclohexyl ketone with a suitable oxidizing agent, such as chromic acid or potassium permanganate.
Q: Is cyclohexanone soluble in water?
A: Cyclohexyl ketone has limited solubility in water, but it is soluble in various organic solvents.
Q: During the synthesis of adipic acid from cyclohexanone, what is the spot test for?
A: The spot test detects the presence of cyclohexyl ketone in adipic acid synthesis by observing a characteristic color change.
Q: How to calculate theoretical yield of synthesis of cyclohexanone?
A: Theoretical yield of cyclohexyl ketone can be calculated based on the stoichiometry of the reaction and the amount of limiting reagent used.
Q: Is cyclohexanone water soluble?
A: Cyclohexyl ketone has limited solubility in water.