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The oxidation of primary alcohols to carboxylic acids can be carried out using a variety of reagents, but O 2 /air and nitric acid dominate as the oxidants on a commercial scale. Large scale oxidations of this type are used for the conversion of cyclohexanol alone or as a mixture with cyclohexanone to adipic acid. Similarly cyclododecanol is ...
Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: [11]. C 6 H 12 + O 2 → (CH 2) 5 CO + H 2 O. This process forms cyclohexanol as a by-product, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid.
Adipic acid or hexanedioic acid is the organic compound with the formula (CH 2) 4 (COOH) 2. From an industrial perspective, it is the most important dicarboxylic acid : about 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon .
Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene. [6] Cyclohexylbenzene is a precursor to both phenol and cyclohexanone. [7] Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam. [8] The oxidative cleavage of cyclohexene gives adipic acid.
This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C 6 H 11 O 2 H. Alternatively, cyclohexanol can be produced by the hydrogenation of phenol: C 6 H 5 OH + 3 H 2 → C 6 H 11 OH
This reaction has been used to convert cyclohexanone to the methyl ester of cyclopropanecarboxylic acid. A generalized mechanism of the Favorskii rearrangement to give a ring contracted product. Note that anion formation has been omitted.
The simplest case refers to the formation of a strictly linear polymer by the reaction (usually by condensation) of two monomers in equimolar quantities. An example is the synthesis of nylon-6,6 whose formula is [−NH−(CH 2) 6 −NH−CO−(CH 2) 4 −CO−] n from one mole of hexamethylenediamine, H 2 N(CH 2) 6 NH 2, and one mole of adipic acid, HOOC−(CH 2) 4 −COOH.
The process, which is catalyzed by platinum supported by aluminium oxide, is exemplified in the conversion methylcyclohexane (a naphthene) into toluene (an aromatic). [2] Dehydrocyclization converts paraffins (acyclic hydrocarbons) into aromatics. [3] A related aromatization process includes dehydroisomerization of methylcyclopentane to benzene: