extracting eugenol from water

[Elite Engineer]

I distilled some cloves for clove oil extraction. Whats the best method for obtaining the oil?

 

-"dry out" the solution with salt

 

- freeze the solution (not sure how this would work b/c eugenol is more dense than water)

 

~EE

[Acme]

Centrifuge?

[Elite Engineer]

Centrifuge?

dont have one

[Acme]

dont have one

Make one?

 

[i would definitely have a shield, unlike this do-it-yourselfer. Duck & cover!!]

Edited August 12, 2015 by Acme

[hypervalent_iodine]

What do you have in the way of organic solvents and glassware?

[Elite Engineer]

What do you have in the way of organic solvents and glassware?

a couple of Erlenmeyer flasks, ranging from 25-250 mL, a few transfer pipettes, beakers 25-300 mL, and a separatory funnel. I just used up the last of my hexane I was hoping I didn't have to use any solvents for this :/

 

-Any help would be greatly appreciated!

Make one?

 

[i would definitely have a shield, unlike this do-it-yourselfer. Duck & cover!!]

is that an alternator? (lol) I made one from an old air conditioner, but I dropped it one day and the shaft bent and wouldn't spin anymore. I'm not sure if centrifuging liquids would really help tho

[John Cuthber]

The fuel used for cigarette lighters is a fairly good solvent for this sort of thing.

A centrifuge isn't going to work unless there's enough eugenol that it's present as drops, rather than solution.

Salting it out might work..

[Sensei]

Whats the best method for obtaining the oil?

 

"The best" means "the fastest", or "the less needing effort/cheap".. ?

 

Eugenol, according to net, is not soluble in water. And has higher density than water.

So it should with time gather on bottom of flask.

I would try simply to leave it for days/weeks alone to see what happens.

Gravity will do the rest.

Edited August 12, 2015 by Sensei

[hypervalent_iodine]

 

"The best" means "the fastest", or "the less needing effort/cheap".. ?

 

Eugenol, according to net, is not soluble in water. And has higher density than water.

So it should with time gather on bottom of flask.

I would try simply to leave it for days/weeks alone to see what happens.

Gravity will do the rest.

Unless there is a significant quantity of it and even assuming it does collect at the bottom of the flask, this won't help that much. You can easily get suitable organic solvent for liquid-liquid extraction as John has mentioned. Better to do it that way.

[DrP]

What is it's bp? wiki says 254C... can you evaporate off the water using some heat to quicken it? If you have a rota vap and a vacuum pump (which I assume you don't) you could stick it on that for a bit.

 

Otherwise could you put the bottom of one of those flasks in an oil bath at high temperature to drive off the water... 110C?

Edited August 12, 2015 by DrP

[Elite Engineer]

 

 

Otherwise could you put the bottom of one of those flasks in an oil bath at high temperature to drive off the water... 110C?

 

So now I have to ask another question.

 

-Is evaporating water off the best low budget technique to extract the oil?

 

-And John, I have no access to butane except for in a pressurized spray can to fill up zippo lighters.

[DrP]

Probably, that or use a separating funnel after the gravity method mentioned above by a couple of people.

[John Cuthber]

 

So now I have to ask another question.

 

-Is evaporating water off the best low budget technique to extract the oil?

 

-And John, I have no access to butane except for in a pressurized spray can to fill up zippo lighters.

I didn't mean butane, I meant the petrol type stuff.

What is it's bp? wiki says 254C... can you evaporate off the water using some heat to quicken it? If you have a rota vap and a vacuum pump (which I assume you don't) you could stick it on that for a bit.

 

Otherwise could you put the bottom of one of those flasks in an oil bath at high temperature to drive off the water... 110C?

It's not clear from the OP but My guess is that Elite Engineer steam distilled the stuff in the first place.

If that's the case, then guess what will happen if you try to boil off the water.

Edited August 12, 2015 by John Cuthber

[Acme]

So now I have to ask another question.

 

-Is evaporating water off the best low budget technique to extract the oil?

 

-And John, I have no access to butane except for in a pressurized spray can to fill up zippo lighters.

Found an article describing the process: Steam Distillation: The isolation of eugenol from cloves

 

They use dichloromethane as a solvent. According to Wiki some paint strippers use dichloromethane, so maybe you can find it at a paint store.

Dichloromethane @Wiki

...

Uses

DCM's volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for many chemical processes.[10]

It is widely used as a paint stripper and a degreaser. ...

...

is that an alternator? (lol) I made one from an old air conditioner, but I dropped it one day and the shaft bent and wouldn't spin anymore. I'm not sure if centrifuging liquids would really help tho

I think it's just a motor, but it's definitely over-kill. Given all said so far it's still not clear to me if you could use a centrifuge or not. ??

[Elite Engineer]

 

 

I think it's just a motor, but it's definitely over-kill. Given all said so far it's still not clear to me if you could use a centrifuge or not. ??

No centrifuge, its just a liquid-liquid extraction

[DrP]

QUOTE: JOHN CUTHBER - "...it is not clear from the OP...."

 

I think you are right John - it is unclear... but I would think that reduced pressure distillation/evaporation of the water could be controlled so that the product doesn't go over with the steam if you get the pressure/temp right. One has a BP of 254C and the other one is, er, around about 100C off the top of my head iirc. I don't think EE has a way of reducing the pressure though. Mind you, as an 'Elite' Engineer he should be able to work out a way. ;-)

[John Cuthber]

QUOTE: JOHN CUTHBER - "...it is not clear from the OP...."

 

I think you are right John - it is unclear... but I would think that reduced pressure distillation/evaporation of the water could be controlled so that the product doesn't go over with the steam if you get the pressure/temp right. One has a BP of 254C and the other one is, er, around about 100C off the top of my head iirc. I don't think EE has a way of reducing the pressure though. Mind you, as an 'Elite' Engineer he should be able to work out a way. ;-)

Whether or not that works will depend on the slopes of the vapour pressure/ temperature curves for eugenol and water.

Good luck finding them.

Did you somehow think the vacuum only reduced the boiling point of the water and left that of the eugenol the same?

My guess is that teh vacuum distillation would work.

It would be possible to separate them with a decent fractionating column.

 

Freezing out the water should work and it's low-tech. The oil should gather at the bottom of the flask.

There's the issue of freezing water in glass flasks to worry about. Transfer the liquid to a suitable plastic bottle first

Solvent extraction into a volatile solvent then re distillation would probably be the best bet.

With a bit of care you could strip non-phenolic materials out during the extraction too.

[DrP]

 

Did you somehow think the vacuum only reduced the boiling point of the water and left that of the eugenol the same?

 

 

No of course not, but I thought you could maybe be more subtle with the heating. More delicate to heat it gently and have it come over slowly and controlled rather than bumping across with half the product. Too low a pressure and it will bump anyway though I suppose.

 

Good idea with the freezing though. That might work.

Edited August 13, 2015 by DrP

[John Cuthber]

The process of steam distillation is nothing to do with bumping.

[Elite Engineer]

So I tried freezing it and so far:

 

-The oils on the surface appeared to freeze with the water.

 

-The oil under the water was IMPOSSIBLE to extract as it was much more viscous and hard to reach. So right now, I'm thinking about ordering more hexane. Unless

 

any of you seasoned chemists know few tricks.

[GM11]

We extract with chloroform, it just drops out in a sep funnel if you use steam for extraction then salt the water. Eugenol is pretty dense when we use chloroform we find it sits under the chloroform layer and any water that was in the cloves sits above the chloroform.

I am wondering if you have actually managed to extract to the oil? Try the salted water the layers should be well defined, this is something we do 5-6 a week at work, but not all cloves give a good yeild