What Is Cyclohexanone Oxime?
Cyclohexanone oxime is an organic compound with a six-membered ring containing an oxime group.
Its chemical formula is C6H11NO, and its CAS number is 100-64-1. It has a molecular weight of 113.16, a melting point in the range of 86-92°C, and a boiling point of 210°C. At room temperature, it appears as a white to a brown solid. Cyclohexanone oxime is soluble in water, ethanol, and acetone, with a water solubility of 16 g/kg.
Uses of Cyclohexanone Oxime
The primary use of cyclohexanone oxime is in the synthesis of ε-caprolactam, a synthetic intermediate of 6-nylon. The end product, 6-nylon, is a synthetic fiber with a melting point of 225°C and a heat resistance temperature of 80-140°C.
It has excellent abrasion resistance, impact resistance, oil resistance, chemical resistance, and electrical properties. It also features superior dyeability compared to 6,6-nylon, which is also a synthetic resin.
In addition to clothing, carpets, and fishing lines, 6-nylon is used as a thermoplastic engineering plastic in machinery, telecommunications equipment, parts for transportation equipment, general merchandise, construction materials, and films.
Properties of Cyclohexanone Oxime
Cyclohexanone oxime is a stable substance under normal storage conditions. Since it may be altered by light, it must be stored away from high temperatures and direct sunlight.
Mixture with strong oxidizing agents should also be avoided due to the risk of reaction. Potential hazardous decomposition products include carbon monoxide, carbon dioxide, and nitrogen oxides.
Types of Cyclohexanone Oximes
Cyclohexanone oxime exists in a variety of product types, primarily R&D reagent products and fine chemicals. Reagent products for research and development are available in different capacities, such as 25g, 100g, and 500g.
For information on fine chemicals and other chemical products, contact the manufacturer.
Other Information on Cyclohexanone Oxime
1. Synthesis of Cyclohexanone Oxime
Cyclohexanone oxime is synthesized using the condensation reaction of Cyclohexanone and hydroxylamine. Another synthesis method used industrially is the reaction of cyclohexane with nitrosyl chloride (NOCl).
In this reaction, cyclohexane is converted to nitrosobenzene by a photo-nitrosation method using NOCl, and the nitrosobenzene is hydrogenated to obtain cyclohexane oxime. The raw material, cyclohexane, is much cheaper than cyclohexanone, making it superior in terms of cost. This method was developed by Toray Industries, Inc. and is sometimes commonly referred to as the Toray method.
2. Epsilon-Caprolactam
The most well-known application of cyclohexanone oxime is the synthesis of ε-caprolactam. The method of producing ε-caprolactam using cyclohexanone oxime was discovered by O. Barach in 1900.
Later, in 1938, IG-Farben of Germany produced 6-nylon in a state ready for spinning by ring-opening polymerization of ε-caprolactam.
3. Synthetic Reaction and Beckmann Transition of ε-caprolactam
The basic synthesis of ε-caprolactam from Cyclohexanone oxime is a reaction using fuming sulfuric acid. This reaction produces about 1.7 tons of ammonium sulfate byproduct per ton of caprolactam because the sulfuric acid used in the reaction must be neutralized with ammonia.
For this reason, methods that do not use fuming sulfuric acid have been studied and reported by companies and academia. For example, Sumitomo Chemical developed a synthesis method using a high-silica MFI zeolite catalyst for gas-phase Beckmann rearrangement, which was industrialized in 2003.
This synthetic method is a catalytic synthetic method that does not produce any ammonium sulfate byproduct at all. Other methods that do not use sulfuric acid have been reported by other research teams, such as a method to obtain caprolactam by Beckmann rearrangement using a cyanuric chloride catalyst.