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The dehydration of cyclohexanol to give cyclohexene

The mixture of cyclohexanol and cyclohexanone is known as "mixed oil" or KA (ketone/alcohol).
An alternative route to cyclohexanol is via the hydrogenation of phenol using a nickel catalyst at ca 400 K and 5 atm:

Substituted Cyclohexanes – Equatorial vs Axial — …

A more recent route to cyclohexanol is the Asahi process from benzene via its hydrogenation to cyclohexene and subsequent hydration to alcohol. This is more energy efficient than the other processes.

PerfectOGems - Week 5- Distillation of Cyclohexene

Cyclohexane is oxidized by passing air through the liquid under pressure in the presence of a catalyst (often a cobalt salt) to yield two products:

To make polyamide 6, pure cyclohexanone is required. When the mixed oil is heated under pressure with copper(ll) and chromium(lll) oxides, the cyclohexanol, which is a secondary alcohol, is dehydrogenated to the corresponding ketone, cyclohexanone:

Week 5- Preparation and Distillation of Cyclohexene ..

Both polyamides are manufactured from via cyclohexane. Hydrogen is passed through liquid benzene in the presence of a nickel catalyst under pressure:

Cyclohexanone is then converted into caprolactam via the oxime (produced by the reaction of the ketone with hydroxylamine - in the form of the salt, hydroxylamine hydrogensulfate):

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Cyclohexene reacts with bromine in the same way …

Again, the bromine is polarised by the approaching pi bond in the cyclohexene. Don't forget to write the words "induced dipole" next to the bromine molecule.

Whereas cyclohexanol is a liquid, ..

This page gives you the facts and a simple, uncluttered mechanism for the electrophilic addition reactions between bromine (and the other halogens) and alkenes like ethene and cyclohexene. If you want the mechanisms explained to you in detail, there is a link at the bottom of the page.

The oxidation of cyclohexanol by nitric acid

One of the monomers, hexanedioic acid is also produced from KA mixed oil (cyclohexanol and cyclohexanone). The mixed oil is oxidized in the liquid phase using moderately concentrated (60%) nitric acid and a copper(II) nitrate and ammonium vanadate(V) catalyst, at 330 K to form hexanedioic acid:

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