[SparkleBird]

Hello everyone,

I'm new to this forum. I have question: does anyone know the reaction mechanism of cyclohexanol conversion to adipic acid with hydrogen peroxide?

I have been looking for the answer for a very long while. I will appreciate your answers. Thanks already.

[SparkleBird]

Hello everyone,

I'm new to this forum. Lecturers at university do not exactly know the reaction mechanism of adipic acid with hydrogen peroxide. You have got to start with cyclohexanol and this should convert to adipic acid with hydrogen peroxide. We are looking forward seeing your answers.

[Babcock_Hall]

Welcome to the forum.  What is your application for this process, and what have you found out so far?

[SparkleBird]

Thanks for your reply.

My coworkers and I have already made adipic acid but we are not sure what the reaction mechanism is exactly like.
We have used tungsten too in lab. We have made adipic acid by using cyclohexanol and hydrogen peroxide. This is the green synthesis.
We also know that cyclohexanol becomes oxepanone during the reaction and oxepanone becomes adipic acid. The unknown reaction is the first step. How exactly does cyclohexanol convert to oxepanone?

[SparkleBird]

Thanks everyone for helping us solving the problem. Most of you literally deserve a massive PhD too, congratulations!!!

[Babcock_Hall]

I am not certain of the mechanism, but it is possible to write one stable intermediate between cyclohexanol and oxepanone.  Why not see if that gets you anywhere?

[orgopete]

Re mechanism.

Hydrogen peroxide can exchange peroxide linkages. If so, then cyclohexanol can form the peralcohol. This can decompose to cyclohexanone by loss of water. Most oxidations progress via a loss of HX from a R2CHOX to give R2C=O. Addition of hydrogen peroxide to cyclohexanone can give the lactone via a Baeyer-Villiger reaction.

To get adipic acid, open the lactone and repeat oxidation of alcohol, aldehyde to acid, and ta da.