[Violekath]

How do you remove toluene from cyclohexane chemically? I know that cyclohexane is fairly nonreactive but I can't find a way for toluene to react to create a separable product.

[Aeon]

You can try to formylate your toluene by performing a Vilsmeier-Haack reaction and then separate the formylated toluene from cyclohexane using a silica filled flash column with a very apolar eluant?

Tell me if it worked.

EDIT: You could also convert your aldehyde to an acid, and then extract with hot water multiple times, using small (30mL or so) volumes. Try it!!

[Honclbrif]

How would you separate liquids with different boilings points?

[fledarmus]

How would you separate liquids with different boilings points?

Wouldn't that be a physical separation rather than a chemical one?

[Honclbrif]

Good point, fledarmus. I didn't read the OP as close as I should have. With that in mind, I'd go with reactivity of the methyl group on the toluene.

[Aeon]

From the chemistry I know, to use the methyl group, you'd need to brominate it, which would be a mess considering the mix is composed of toluene and cyclohexane.

I still think you'd be better off formylating toluene and then oxidate it, then separating the components in a flash column. Any other suggestions?

[discodermolide]

From the chemistry I know, to use the methyl group, you'd need to brominate it, which would be a mess considering the mix is composed of toluene and cyclohexane.

I still think you'd be better off formylating toluene and then oxidate it, then separating the components in a flash column. Any other suggestions?

Why not use acidic permanganate to give the acid then neutralize and extract with NaOH. Sodium benzoate in water cyclohexane above!

[Aeon]

discodermolide:

EDIT: You could also convert your aldehyde to an acid, and then extract with hot water multiple times, using small (30mL or so) volumes. Try it!!

The product would not be benzoic acid, but (o,m,p)-toluic acids, which are not very soluble in water, according to a couple of sources. I totally agree that it would be the most sensible way to extract it!

It would be nice to hear from the asker, see if any of the options work

[discodermolide]

discodermolide:

EDIT: You could also convert your aldehyde to an acid, and then extract with hot water multiple times, using small (30mL or so) volumes. Try it!!

The product would not be benzoic acid, but (o,m,p)-toluic acids, which are not very soluble in water, according to a couple of sources. I totally agree that it would be the most sensible way to extract it!

It would be nice to hear from the asker, see if any of the options work

The oxidation  of toluene using H2SO4/permanganate produces benzoic acid see  http://en.wikipedia.org/wiki/Toluene.

And yes, I agree the poster should reply!

[Aeon]

I stand corrected.