: CS1 maint: uses authors parameter ( link) ^ "Phenol - The essential chemical industry online".Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. National Institute for Occupational Safety and Health (NIOSH). Immediately Dangerous to Life or Health Concentrations (IDLH). ^ a b c Sigma-Aldrich Co., Cyclohexanone.^ Data extract from Landolt-Börnstein IV/25: Viscosity of Pure Organic Liquids and Binary Liquid Mixtures.^ a b c d NIOSH Pocket Guide to Chemical Hazards.^ NIOSH Pocket Guide to Chemical Hazards.^ International Chemical Safety Card 0425.Like cyclohexanol, cyclohexanone is not carcinogenic and is moderately toxic, with a TLV of 25 ppm for the vapor. Illicit use Ĭyclohexanone has been used in the illicit production of phencyclidine and its analogs and as such is often subject to additional checks before purchase. It also forms an enamine with pyrrolidine. It forms a trimethylsilylenol ether upon treatment with trimethylsilylchloride in the presence of base. In the presence of light, it undergoes alpha-chlorination to give 2-chlorocyclohexanone. In addition to the large scale reactions conducted in service of the polymer industry, many reactions have been developed for cyclohexanone. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6: Laboratory reactions The other half of the cyclohexanone supply is converted to cyclohexanone oxime. For this application, the KA oil (see above) is oxidized with nitric acid. About half of the world's supply is converted to adipic acid, one of two precursors for nylon 6,6. The great majority of cyclohexanone is consumed in the production of precursors to Nylon 6,6 and Nylon 6. An alternative method utilizes the safer and more readily available oxidant sodium hypochlorite. Laboratory methods Ĭyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide ( Jones oxidation). Therefore, this newer process without producing the acetone by-product appears attractive and is similar to the cumene process as a hydroperoxide is formed and then decomposed to yield two key products. This latter product is oxidized to a hydroperoxide and then cleaved to phenol and cyclohexanone. ĮxxonMobil developed a process in which benzene is hydroalkylated to cyclohexylbenzene. This process can also be adjusted to favor the formation of cyclohexanol. Alternatively, cyclohexanone can be produced by the partial hydrogenation of phenol: In some cases, purified cyclohexanol, obtained by hydration of cyclohexene, is the precursor. ![]() The oxidation involves radicals and the intermediacy of the hydroperoxide C 6H 11O 2H. This process co-forms cyclohexanol, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid. Include all valence lone pairs in your answer Include counter-ions, eg., Na", I, in your submission, but draw them in their own separate sketcher Draw one structure per sketcher.Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: C 6H 12 + O 2 → (CH 2) 5CO + H 2O Electron flow is indicated with curved arrows. Add additional sketchers using the drop-down menu in the bottom rig comer Separate multiple products using the+ sign from the drop-down menu Show transcribed image text and les à nment/takeCovalentActivity.do?locator-assignment-tak e&takeAssignmentSessionlocators assignment-take Draw the products of the reaction shown. Include all valence lone pairs in your answer Include counter-ions, eg., Na", I, in your submission, but draw them in their own separate sketcher Draw one structure per sketcher. And les à nment/takeCovalentActivity.do?locator-assignment-tak e&takeAssignmentSessionlocators assignment-take Draw the products of the reaction shown.
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