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This section provides an overview for cyclohexanone oxime as well as their applications and principles. Also, please take a look at the list of 5 cyclohexanone oxime manufacturers and their company rankings. Here are the top-ranked cyclohexanone oxime companies as of December, 2024: 1.KANTO CHEMICAL CO.,INC., 2.Junsei Chemical Co.,Ltd., 3.Alfa Aesar, Thermo Fisher Scientific..
Table of Contents
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.
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.
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.
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.
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.
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.
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.
*Including some distributors, etc.
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Kanto Chemical Co. Inc., founded in 1944 and headquartered in Tokyo, Japan, is a reagent manufacturer with overseas affiliates in other countries, including China, France, USA, Taiwan, and Malaysia. Its product portfolio includes analytical reagents, ionic liquids, Iodine compounds, ultra-pure chemicals, and water analysis kits. The company is also developing regenerative medicine and genetics reagents and has over 50,000 products. It has several certifications, including ISO 9001, acquired in 1994, making it the first Japanese company in the reagent industry. Other certifications are ISO 14001, ISO 13485, and ISO/IEC 17025.
Junsei Chemical Co. Ltd., established in 1948 and headquartered in Tokyo, Japan, is a manufacturer of chemical reagents and chemical products, including commissioned synthesis of chemical products. Some of the products it makes include Sodium chloride solution, concentrated glycerin, calcium chloride, ascorbic acid, and nitric acid. The chemical products have a wide range of applications and can be used in pathological examination, as food additives, for analysis, and in the pharmaceutical industry. All its plants, including its research institute, are ISO4001 and ISO9001 certified, while its Saitama and Ibaraki plants are equipped with buildings that comply with GMP.
Merck, started in 1668 and based in Darmstadt, Germany, is a supplier of solutions and services for research, development, and manufacture of pharmaceutical and biotechnological drug therapies. The company serves the life science industry and has a broad portfolio of 300,000 products, including biopharmaceutical manufacturing, industrial microbiology, reagent, life science research, and water purification products. It is available in 66 countries, brings together six brands, and has several ISO certifications, including ISO 13485, ISO 14001, ISO 13485, and ISO 50001.
Millipore Sigma, formerly known as Sigma-Aldrich, was created in 175 through the merger of Sigma Chemical Company and Aldrich Chemical company and today is a subsidiary of Merck. Millipore Sigma is a life science and biotechnology company serving the industry with several products and services. Some of their product categories include peptide synthesis materials, biochemicals, building blocks, catalysts, chemical biology, chemical synthesis, flavors & fragrances, formulation, lab chemicals, lab safety, APIs, and stable isotopes. Services include characterization, contract manufacturing, custom products, software, support, testing, and mRNA development & manufacturing.
Alfa Aesar is based in Lancashire, United Kingdom. Alfa Aesar is part of Thermo Fisher Scientific, is a manufacturer and supplier of chemicals, metals, and life science products for research and development. Alfa Aesar’s product lines include chemicals, life science, materials & metals, catalysts, and analytical & lab ware. Chemical offerings include inorganic compounds, organic compounds, organometallic, and solvents. Life sciences include biotechnology products, cellular & molecular biology, genomics, and immunology. Materials & metal include alloys, carbon, etchants, and more. Catalysts include ferrocenes, fuel cell products, and precious metals & catalysts. Alfa Aesar also offers custom manufacturing options.
Ranking as of December 2024
Derivation Method| Rank | Company | Click Share |
|---|---|---|
| 1 | KANTO CHEMICAL CO.,INC. |
44.4%
|
| 2 | Junsei Chemical Co.,Ltd. |
22.2%
|
| 3 | Alfa Aesar, Thermo Fisher Scientific. |
11.1%
|
| 4 | MilliporeSigma |
11.1%
|
| 5 | Merck |
11.1%
|
Derivation Method
The ranking is calculated based on the click share within the cyclohexanone oxime page as of December 2024. Click share is defined as the total number of clicks for all companies during the period divided by the number of clicks for each company.Number of Employees
Newly Established Company
Company with a History
*Including some distributors, etc.
| Country | Number of Companies | Share (%) |
|---|---|---|
|
Japan
|
2 | 66.7% |
|
United Kingdom
|
1 | 33.3% |
