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Most methylcyclohexane is extracted from petroleum but it can be also produced by catalytic hydrogenation of toluene: CH 3 C 6 H 5 + 3 H 2 → CH 3 C 6 H 11. The hydrocarbon is a minor component of automobile fuel, with its share in US gasoline varying between 0.3 and 1.7% in early 1990s [10] and 0.1 to 1% in 2011. [11]
Hydration reaction mechanism from 1-methylcyclohexene to 1-methylcyclohexanol. Many alternative routes are available for producing alcohols, including the hydroboration–oxidation reaction , the oxymercuration–reduction reaction , the Mukaiyama hydration , the reduction of ketones and aldehydes and as a biological method fermentation .
[1] [2] [3] It can also be synthesized as a side product of the dehydration of 2-methylcyclohexanol into 1-methylcyclohexene. Structure
Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: [5]. 2 C 6 H 12 + O 2 → 2 C 6 H 11 OH. This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid.
Oxidation of 1-methylcyclohexene catalyzed by cytochrome P450 yields a 2:1 mixture of hydroxylation to epoxidation products. [4] The stereochemistry of hydroformylation has been examined using 1-methylcyclohexene. The main product has the formyl group on the less substituted alkene-carbon, trans with respect to the methyl substituent.
It has been patented for use in air fresheners. [8]U.S. Patent 4915825 describes a froth flotation process for cleaning coal where a mixture of 95% MCHM, 4% water, and 0.1% 4-methylcyclohexanemethanol monoether (such as 4-(methoxymethyl)cyclohexanemethanol) is used as a frothing agent, and finely divided coal particles adhere to air bubbles induced into the agent which rise to the surface.
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