Ok ive been messing around with eugenol lately and was wondering if anyone could shed some light. Eugenol was distilled from coarsely ground cloves. A small scale microwave isomerisation was carried out, which appeared to have worked. Eugenol in alcoholic NaOH with a tiny amount of NaCl to enhance the conductivity of the solution was placed in the microwave and irradiated in short bursts. With an alcoholic FeCl3 solution, eugenol gave a deep blue color and the 'isoeugenol' from the microwave gave a green color.
EtOH was evaporated and a slightly waxy red-orange salt was left, assumed to be the sodium salt of isoeugenol. Following the various literature on the subject, an electrolytic cell was prepared. The anodic beaker contained the salt, the cathodic beaker contained an aqueous solution of NaOH which was connected via a salt bridge. The electrodes were Zn metal and the power supply was 12V @ 1A. After the cell had been running for a few hours the orange-red color had lightened up a bit and was looking paley yellow. The Zn was taken from a 6V lantern battery and still would have had a wee bit o MnO2 left on it. After a few hours, i had this bright idea to add a tiny amount of MnO2, which definitely caused more bubbles (oxygen?) being evolved. (The MnO2 was in place of the lead peroxide stated in literature). After the cell was turned off, the solution was filtered. Upon acidifying a small amount, the solution turned milky white. Had a real weird smell too, similar to when i did a small scale test to oxidize Isoe with KMnO4. Nothing even remotely vanillin smelling. 

So now,
A) the isomerization failed horribly, is there anyway to test the extent of isomerization?
B) was the cell left on for too long(over-oxidation)? (something definitely reacted as there was no oil recovery after)
C) How essential is the PbO2(perhaps the MnO2 over oxidised or reacted differently?), would it be worth creating an electrode from MnO2?

Any ideas? (attached is the patent)

The patent says that platinum electrodes were used 

There is lots of PbO2 in a car/motorcycle lead acid battery. It is probably in a usable form already if you wanted to use it as an electrode.

Platinum is what is known as a nonconsumable electrode, and many times cannot be replaced by less noble materials without affecting the outcome of the reaction 

PbO2 is specifically used for a few reasons, one of which is the hydrogen overpotential, another is catalytic effect. Often the researchers simply try things until they work, when it comes to electrochem

Lead can't always be substituted in these cases. But PbO2 is easy enough to make, and you can coat a lead electrode with PbO2 fairly easily.

Good to be here, Sedit I realized I wasn't pollinating enough flowers.

You have a very good point. What I was actually suggesting was:

Try it with lead first. If it doesn't work, try it with PbO2.



Platinum can be gotten, though yes it is fairly pricey, however you can get it in foil, at which point you can cover a glass plate with it, and with some engineering connect it to your voltage source. One simple way is to get a  small piece of platinum wire which is flash fused to the foil, then the other end is led upwards through a glass tube which you have sealed off with heat on the bottom, so you can use copper wire for most of that path.

So we are trying to get to Vanillin from Eugenol? Isomerization is a pain yes, however doing it in PEG with the classic method apparently does wonders. Let me see...

ah yes here we go:

Isomerization of Eugenol to Isoeugenol
Place 50.0g of potassium hydroxide, 200 ml of (diethylene glycol), and 47.0 g of eugenol in a 500-ml round bottom flask. Assemble a reflux apparatus with a thermometer inserted into the reflux condenser and projected below the surface of the mixture. Heat the mixture with occasional swirling until the boiling point is attained (150°C). When the solution starts to bubble slightly (about 138°C), it must be watched carefully so that the mixture will not bump. Once the mixture has stabilized at the boiling point (150°C), allow the solution to reflux for 1.5 hr. When the boiling action is stabilized sufficiently, the thermometer may he removed.

Dilute the cooled reaction mixture with 450 ml of water and acidify it with concd hydrochloric acid (about 61 ml required) to a pH of 2 to 3. Extract the isoeugenol from the mixture with three 75-ml portions of petroleum ether (bp 30-60°C), add 25 ml of diethyl ether to the combined extracts to make the mixture homogeneous, and dry the combined extracts with 2.5 g of anhydrous magnesium sulfate. Remove the solvent on a steam bath to obtain 35.3 g (75.1% yield) of dark brown isoeugenol. The mixture should be stored in a refrigerator to prevent polymerization. It is of suitable purity for conversion to vanillin and enough is prepared for four students. There is no evidence of any eugenol in the nmr spectrum.

PEG can be used as a substitute for DEG. Dont use straight Glycol.. it works but is a real pain. The ether is recommended to increase yields.. I am thinking you might be able to use another non polar, but dont quote me on that.