[billnotgatez]

It was a separate book published by Readers Digest about massage and aromatherapy.
I will try to get the title etc.

[pantone159]

Anyone who wants a copy of the lab manual just send me an e-mail (james_gore1984@hotmail.com)

Thanks, James, that was useful.  This seems like a good extraction experiment.

The procedure is basically to steam distill ground cloves to get clove oil, and dissolve this in dichloromethane (DCM).  Then, this is extracted with NaOH solution.  The eugenol (which has a phenol-like -OH part) loses the proton and then goes into the water layer.  Then, this water layer is acidified, giving the eugenol the proton back and this is extracted with more DCM.  Dry, filter, and evaporate the DCM to  recover eugenol.

I think I could replace the steam distillation (since I don't have the equipment) by extracting the ground cloves in EtOH, then evaporating most of that, dissolving that in DCM, and proceeding from there.  Not as slick, but it should do.

This works well because eugenol has the phenol part that can be acid-base extracted.  (Soluble in water at high pH, insoluble at low pH).  

Another promising extraction might be piperine from white pepper.  (Black pepper has lots of piperine too, it is most of the flavor, but it does have some other things.  White pepper is, I think, more pure piperine.)
http://en.wikipedia.org/wiki/Piperine
This has a nitrogen, so it would also be amenable to acid-base extraction.  (Protonate the N in acid, making it water soluble, but insoluble when deprotonated in base.)

Another fun project might be to isomerize estragole (from tarragon)
http://en.wikipedia.org/wiki/Estragole
to anethole (licorice flavor)
http://en.wikipedia.org/wiki/Anethole
which, I think, can be done by heating with base.  This would change tarragon smell to licorice smell, which might be interesting.

[billnotgatez]

This was the Reader's digest publication I mentioned in a previous post

Hands on Health
Subtitle – Health and healing the natural way

ISBN: 0-7621-01466

[pantone159]

Results from my eugenol extraction experiment:

Instead of steam distillation (I don't have the equipment), I decided to extract the eugenol from cloves by soaking it in 95% EtOH.  I put around 25 g of powdered clove into a flask-shaped beaker, and added c. 70 g of 95% EtOH, and let this digest for a couple of weeks with occasional swirling.  (I was not in any hurry.)  I filtered this off, and added a similar amount of fresh solvent, let it digest again, then filtered, and combined the two filtrates which were green liquids.  I evaporated c. 2/3 of the solvent, and then pretended like this was what I got from steam distillation.

My extraction procedure plan, based on the stuff from James Gore as well as some other sources I could find was:

Extract from the initial stuff, with 25,20,20 mL dichloromethane (DCM).  Combine these extracts, then wash the DCM with 25,25 mL water.  Extract from the DCM with 30,25,25 mL of 5% NaOH.  Wash the NaOH with 15 mL DCM.

Next, acidify the NaOH (with 5% HCl) to pH 1.  This step was a little different in the various procedures I read.  James' proc said to acidify to pH 9, others said pH 1, I aimed for 1.  The mixture turns cloudy as it becomes acidic.

Extract the acidified aq solution with 20,25 mL DCM.  Wash this DCM with 15 mL H2O, then 15 mL of half-saturated NaCl solution.  Take the DCM, add anh MgSO4 to dry, filter, and evaporate the solvent, yielding eugenol.

When I started to actually do this, the first part had a complication.  I added the DCM to my EtOH extract, but I did not get two layers.  So, I added c. 20 g of H2O to force separation to occur.  After that, it mostly proceeded as planned.  I need to improve my drying technique, my final DCM solution wasn't in fact dry from the amount of MgSO4 I used.  Anyways, I did end up with a small amount (c. 0.25 g) of a yellow-brown oil which I assume is eugenol.

I'm not sure what yield I should expect, but I think my results (c. 1 % yield) are very low.  I think the reason is that the initial EtOH extraction didn't take up most of the eugenol.  I don't think I lost that much in the processing.  (After evaporating the waste DCM portions, there did seem to be some eugenol in there, along with a bunch of other goopy junk, but not enough to explain the low yield.)

So, I think I really did want to use steam distillation, after all.   
In any case, I did get some eugenol, so I am happy.

[mir]

At pharmacies around here you can get a mix of essential oils to make your own "glögg", which is  a kind of spiced wine you drink warm at christmas time.

mmmm, gløgg! :-)

I learned in my surviving training to extract water soluble compounds from needles on trees to make some sort of a tea.