Cyclohexanone

Base Information

• Chemical Name: Cyclohexanone
• CAS No.: 108-94-1
• Deprecated CAS: 11119-77-0,9075-99-4
• Molecular Formula: C6H10O
• Molecular Weight: 98.1448
• Hs Code.: 2914.22
• European Community (EC) Number: 203-631-1
• ICSC Number: 0425
• NSC Number: 5711
• UN Number: 1915
• UNII: 5QOR3YM052
• DSSTox Substance ID: DTXSID6020359
• Nikkaji Number: J2.872J
• Wikipedia: Cyclohexanone
• Wikidata: Q409178
• Metabolomics Workbench ID: 38285
• ChEMBL ID: CHEMBL18850
• Mol file: 108-94-1.mol

Synonyms:cyclohexanone

Chemical Property of Cyclohexanone

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 3.4 mm Hg ( 20 °C)
• Melting Point: -16.4 °C
• Refractive Index: n20/D 1.450(lit.)
• Boiling Point: 155.65 °C
• PKA: 17(at 25℃)
• Flash Point: 44 °C
• PSA: 17.07000
• Density: 0.947 g/cm³
• LogP: 1.51960
• Storage Temp.: Flammables area
• Solubility.: 90g/l
• Water Solubility.: 150 g/L (10 ºC)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 98.073164938
• Heavy Atom Count: 7
• Complexity: 68.2
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Cyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20-41-38-20/21/22
• Safety Statements: 25-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: C1CCC(=O)CC1
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance and the vapour are irritating to the eyes, skin and respiratory tract. Exposure far above the OEL could cause lowering of consciousness.
• Uses: Cyclohexanone is an important chemical raw material, being the major intermediates of making nylon, caprolactam and adipic acid. It is also an important industrial solvent, for example, for paints, especially for those containing nitrocellulose, vinyl chloride polymers and their copolymers or methacrylate polymer paints. Used as an excellent solvent for pesticides such as organophosphate insecticide. It is used as a solvent for dyes, viscous solvents for piston aviation lubricants, solvents for greases, waxes and rubbers. Also used as leveling agent for dyeing and fading silk; degreasing agents for polishing metal; wood coloring paint; also used for cyclohexanone stripping, decontamination and spot removal. Cyclohexanone and cyanoacetic acid can have condensation reaction to generate cyclohexylidene acetic acid, and then followed by elimination and decarboxylation to get cyclohexene acetonitrile, and finally giving cyclohexene ethylamine by hydrogenation [3399-73-3]. Cyclohexene ethylamine is a intermediate for some drugs. Industrial solvent for cellulose acetate resins, vinyl resins, rubber, and waxes; solventsealer for polyvinyl chloride; in printing industry; coating solvent in audio and videotape production Cyclohexanone is used as an industrial solvent and paint remover. It acts as a precursor to nylon 6,6 and nylon 6 and cyclohexanone oxime, which gives caprolactam on rearrangement. Further, it is used as a chemical reaction medium, adhesives, sealants and agricultural products. Cyclohexanone is used in the productionof adipic acid for making nylon; in thepreparation of cyclohexanone resins; and asa solvent for nitrocellulose, cellulose acetate,resins, fats, waxes, shellac, rubber, and DDT..
• Production method: In the 1940s, the industrial production of cyclohexanone mainly applied hydrogenation of phenol to generate cyclohexanol, followed by dehydrogenation to give cyclohexanone. In the 1960s, with the development of petrochemical industry, the cyclohexane oxidation production method gradually dominated. In 1967, the one step method of phenol hydrogenation, developed by the Netherlands National Mining Company (DSM) was industrialized. This method has short production process, good product quality and high yield, but the raw materials of phenol and catalyst are expensive, so the majority of the industry still adopts the cyclohexane oxidation method. 1. Phenol method takes nickel as a catalyst; first apply hydrogenation of phenol to give cyclohexanol, followed by dehydrogenation to give cyclohexanone using zinc as the catalyst for zinc. 2. Cyclohexane oxidation method uses cyclohexane as the raw material; first apply non-catalyst condition; use oxygen-rich air for oxidation to give cyclohexyl hydroperoxide, followed by decomposition into the mixture of cyclohexanol, cyclohexanone, alcohol and ketone in the presence of tert-butyl chromate catalyst; further apply a series of distillation refinement to get qualified products. Raw material consumption quota: cyclohexane (99.6%) 1040kg / t. 3. Benzene hydrogenation oxidation method; benzene subjects to hydrogenation (with hydrogen) at 120-180 ℃ in the presence of nickel catalyst to generate cyclohexane; cyclohexane has oxidation reaction with air at 150-160 ℃, 0.908MPa to obtain the mixture of cyclohexanol and cyclohexanone; separate them to obtain the cyclohexanone product. Cyclohexanol is dehydrogenated at 350-400 ° C in the presence of a zinc-calcium catalyst to produce cyclohexanone. Raw material consumption quotas: benzene (99.5%) 1144kg / t, hydrogen (97.0%) 1108kg / t, caustic soda (42.0%) 230kg / t.
• Description: Cyclohexanone, a colorless liquid is a cyclic ketone. It is an important building block for the synthesis of a variety of organic compounds. Majority of the cyclohexanone synthesized is utilized as an intermediate in the synthesis of nylon.Used as a polyvinyl chloride (PVC) solvent, cyclohexanone caused contact dermatitis in a woman manufacturing PVC fluidotherapy bags. Cyclohexanone probably does not cross react with cyclohexanone resin. A cyclohexanone-derived resin used in paints and varnishes caused contact dermatitis in painters.
• Physical properties: Clear, colorless to pale yellow, oily liquid with a peppermint-like odor. Experimentally determined detection and recognition odor threshold concentrations were identical: 480 μg/m3 (120 ppmv) (Hellman and Small, 1974).

Technology Process of Cyclohexanone

There total 1712 articles about Cyclohexanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

chloro-trimethyl-silane (75-77-4) + cycloxexanone dimethyl ketal (933-40-4) → Trimethylmethoxysilane (1825-61-2) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + methyl iodide (74-88-4)

Guidance literature:

With potassium iodide; In acetonitrile; at 45 - 50 ℃; for 2h;

Reference yield: 40.0%

C15H21NO2 → C15H21NO2 (1227639-08-8) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + 4-dimethylamino-benzaldehyde (100-10-7)

Guidance literature:

With (1R,2R)-2-(diethylamino)cyclohexanaminium trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 6h; optical yield given as %ee; enantioselective reaction; Resolution of racemate;

DOI:10.1002/chem.201000181

Reference yield: 34.0%

(C4H9)3SnOC6H10CH(CH3)COOCH3 (66957-29-7) → ethylidenecyclohexane (1003-64-1) + tributyltin methoxide (1067-52-3) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + methyl 2-(tributylstannyl)propionate (142653-20-1)

Guidance literature:

byproducts: CO2; 52 % decompn. at 150°C/0.8 Torr for 8 h;

DOI:10.1016/S0022-328X(00)84723-3

upstream raw materials:

diazomethane

methanol

diethyl ether

cyclopentanone

Downstream raw materials:

2-pyrrolidin-1-ylmethyl-cyclohexanone

2-allylcyclohexan-1-one

1-(1-Cyclohexen-1-yl)pyrrolidine

1-cyclohexylpiperidine

Refernces

• 1、 Kats, M. M.,Shul'pin, G. B.. "PHOTOOXIDATION OF ALKANES AND BENZENE BY POLYVANADATE IN CF3CO2H". . p. 2233. Retrieved 1990.
• 2、 Merckle,Bluemel. "Improved Rhodium Hydrogenation Catalysts Immobilized on Oxidic Supports". . p. 584 - 588. Retrieved 2003.
• 3、 Hamar-Thibault, Sylvaine,Moutet, Jean-Claude,Tingry, Sophie. "Polypyrrole films containing rhodium(I) and iridium(I) complexes: Improvement in their synthesis and electrocatalytic activity in aqueous media". . p. 31 - 37. Retrieved 1997.
• 4、 De Souza, Priscilla M.,Rabelo-Neto, Raimundo C.,Borges, Luiz E. P.,Jacobs, Gary,Davis, Burtron H.,Sooknoi, Tawan,Resasco, Daniel E.,Noronha, Fabio B.. "Role of keto intermediates in the hydrodeoxygenation of phenol over Pd on oxophilic supports". . p. 1318 - 1329. Retrieved 2015.
• 5、 Mekrattanachai, Pagasukon,Cao, Changyan,Li, Zhaohua,Li, Huining,Song, Weiguo. "Cobalt immobilized on hydroxyapatite as a low-cost and highly effective heterogeneous catalyst for alkenes epoxidation under mild conditions". . p. 37303 - 37306. Retrieved 2018.
• 6、 Zhang, Pengling,Wang, Liang,Ren, Limin,Zhu, Longfeng,Sun, Qi,Zhang, Jian,Meng, Xiangju,Xiao, Feng-Shou. ""Solvent-free" synthesis of thermally stable and hierarchically porous aluminophosphates (SF-APOs) and heteroatom-substituted aluminophosphates (SF-MAPOs)". . p. 12026 - 12033. Retrieved 2011.
• 7、 Brown, Herbert C.,Kulkarni, Surendra U.,Rao, C. Gundu,Patil, Vemanna D.. "ORGANOBORANES FOR SYNTHESIS. 4. OXIDATION OF ORGANOBORANES WITH PYRIDINIUM CHLOROCHROMATE. A DIRECT SYNTHESIS OF ALDEHYDES FROM TERMINAL ALKENES VIA HYDROBORATION". . p. 5515 - 5522. Retrieved 1986.
• 8、 Li, Zelong,Liu, Jianhua,Xia, Chungu,Li, Fuwei. "Nitrogen-functionalized ordered mesoporous carbons as multifunctional supports of ultrasmall Pd nanoparticles for hydrogenation of phenol". . p. 2440 - 2448. Retrieved 2013.
• 9、 El-Korso, Sanaa,Khaldi, Ilyes,Bedrane, Sumeya,Choukchou-Braham, Abderrahim,Thibault-Starzyk, Frédéric,Bachir, Redouane. "Liquid phase cyclohexene oxidation over vanadia based catalysts with tert-butyl hydroperoxide: Epoxidation versus allylic oxidation". . p. 89 - 96. Retrieved 2014.
• 10、 Becker, James Y.,Zinger, Baruch. "Anodic Oxidation of Heterocumulenes in Acetonitrile". . p. 2327 - 2329. Retrieved 1982.