Cyclohexanone facts for kids
Quick facts for kids Cyclohexanone |
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Preferred IUPAC name
Cyclohexanone
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| Other names | oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone |
| Identifiers | |
| CAS number | |
| PubChem | |
| DrugBank | DB02060 |
| KEGG | C00414 |
| ChEBI | CHEBI:17854 |
| SMILES | C1CCC(=O)CC1 |
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InChI
InChI=1/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
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| Properties | |
| Molecular formula | |
| Molar mass | 0 g mol-1 |
| Appearance | Colorless liquid |
| Odor | Peppermint or acetone-like |
| Density | 0.9478 g/mL, liquid |
| Melting point | |
| Boiling point | |
| 8.6 g/100 mL (20 °C) | |
| Solubility in all organic solvents | Miscible |
| log P | 0.81 |
| Vapor pressure | 5 mmHg (20 °C) |
| −62.04·10−6 cm3/mol | |
| Refractive index (nD) | 1.447 |
| Viscosity | 2.02 cP at 25 °C |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−270.7 kJ·mol−1 |
| Std enthalpy of combustion ΔcH |
−3519.3 kJ·mol−1 |
| Standard molar entropy S |
+229.03 J·K−1·mol−1 |
| Hazards | |
| NFPA 704 |
2
1
0
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| Explosive limits | 1.1–9.4% |
| U.S. Permissible exposure limit (PEL) |
TWA 50 ppm (200 mg/m3) |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Cyclohexanone is a special type of organic compound that looks like a ring of six carbon atoms. One of these carbon atoms is double-bonded to an oxygen atom, forming what chemists call a "ketone" group. It's a clear, oily liquid that smells a bit like peppermint or acetone. If you leave it out for a while, it might turn a light yellow color.
This chemical doesn't mix well with water but blends easily with many other organic liquids. Every year, millions of tons of cyclohexanone are made. Its main job is to help create nylon, a very important material used in many products we see every day.
Contents
How is Cyclohexanone Made?
Cyclohexanone was first discovered in 1888 by a scientist named Edmund Drechsel. He found it while using electricity to break down phenol in water. He figured out that the phenol first changed into another chemical called cyclohexanol, and then into cyclohexanone.
Making it in the Lab
In a science lab, cyclohexanone can be made from cyclohexanol. This process involves using special chemicals like chromium trioxide or sodium hypochlorite to change cyclohexanol into cyclohexanone. Sodium hypochlorite is a safer and more common chemical to use for this.
Making it for Industry
For large-scale production, cyclohexanone is often made by mixing cyclohexane with air. This process usually uses cobalt as a helper chemical, called a catalyst.
- C6H12 + O2 → (CH2)5CO + H2O
This method also creates cyclohexanol as a side product. The mixture of cyclohexanone and cyclohexanol is very important for making adipic acid. Adipic acid is a key ingredient for nylon.
Another way to make cyclohexanone is by adding hydrogen to phenol.
- C6H5OH + 2 H2 → (CH2)5CO
This process can also be adjusted to make more cyclohexanol if needed.
A company called ExxonMobil developed a different method. They start with benzene and turn it into cyclohexylbenzene. This new chemical is then changed into a hydroperoxide, which finally breaks down into phenol and cyclohexanone. This method is interesting because it produces two useful chemicals without creating acetone as a byproduct.
What is Cyclohexanone Used For?
Most of the cyclohexanone produced worldwide is used to make materials for Nylon 6,6 and Nylon 6. These are two common types of nylon.
About half of the world's cyclohexanone becomes adipic acid. Adipic acid is one of the two main ingredients needed to make nylon 6,6. To do this, the mixture of cyclohexanone and cyclohexanol (called "KA oil") is treated with nitric acid.
The other half of the cyclohexanone is turned into a chemical called cyclohexanone oxime. With the help of sulfuric acid, this oxime changes into caprolactam. Caprolactam is the main ingredient for making nylon 6.
Important Safety Information
Cyclohexanone is a chemical that should always be handled with care. It can irritate your skin and eyes. It is important to remember that all chemicals, including cyclohexanone, should only be handled by trained adults in a safe environment, following all safety rules. Always wear proper safety gear, like gloves and eye protection, when working with chemicals.
