anthraquinone subst. for benzoquinone?

[pyroflatus]

A question from the ignorant: Can anthraquinone be substituted for the p-benzoquinone specified in Wacker oxidations of (propenyl/allyl)benzenes.

Benzoquinone is unavailable, but a plentiful supply of anthraquinone is at hand. Since palladium salts are lying about, one is tempted to wonder whether anthraquinone is a useable replacement for benzoquinone in Wacker oxidation.

[Rhodium]

It's possible. Please try that out with an equimolar amount so that we can find out.

[pyroflatus]

Something new and untried, and even potentially useful?! Good Lord, I always wanted to find something like that to give back to the Hive.
I'll set about purifying it this week and try a small Wacker oxidation.

[pyroflatus]

The anthraquinone is 80%, in a widely available garden product, though this lot is at least ten years old, but has been sealed the entire time.
Solubilty of anthroquinone is <100mg/100mL in water at 23°C

I haven't been able to find solubility data for anthraquinone in other solvents, so I'm still searching for the right solvent.

The anthraquinone is mixed with anticaking agent(s) insoluble in ethanol or dichloromethane, which is easily filtered out with vacuum.

Results so far:
solubility 1.3g per 100g dichloromethane @ 25°C

Tried to dissolve and then recrystallize from ethanol, which was weird; some nice beige crystals crashed out during filtering, and a short stay in the fridge had about a gram of crystals collected from 50g of ethanol, but reducing the volume to about half by evaporation failed to produce any more crystals.

Adding water to the ethanolic solution caused some crystallization, but it was so rapid that crystals formed are so small they slip right through filter paper.

I've scoured the net for information on anthraquinone, but can't seem to find any solubility data.  If anyone has any info regarding solubility in any solvent I'd be interested.

I'll keep working till I've got the requisite 30g of nice beige crystals required for a 1/10 scale of 

this

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/wacker.benzo-meoh.html).

[lugh]

CRC states that anthroquinone crystallizes as yellow rhomboid needles from a mixture of alcohol and benzene; it's solubility increases markely in hot benzene    Merck Index states the solubility in g/100 g: alcohol .05 at 18°C, .44 at 25°C, 2.25 at reflux; ether at 25°C .11; chloroform at 20°C .61, at 40°C 1.00, at 60°C 1.60; benzene at 20°C .26, 40°C .50, 60°C 1.00, 80°C 1.80; and toluene at 25°C .30    Anthroquinone can also be purified by fractional crystallization from strong sulfuric acid or by vacuum sublimation, it can cause skin irritation and sensitzation  

[pyroflatus]

Thanks Lugh, you've just saved me a lot of time experimenting.    
I think I'll try vacuum sublimation next, since it doesn't seem to be very soluble in much at all. The trusty nomograph tells me it should evaporate at ~160°C at ~400mmHg, so i'll probably end up choking up a condenser with it. Should be fun.
update: vacuum sublimation works very well. :-) Half a day was spent extracting ~4g using ethanol, but 25g was yielded in two hours using sublimation, even without proper equipment. Thanks Lugh. As soon as I have 30g I'll start an attempted oxidation.

[pyroflatus]

An oxidation was attempted at 1/10 of the scale of the Methyl Man Wacker oxidation, substituting anthraquinone for p-benzoquinone.
18.1g of isosafrole was the starting material, and after attempted oxidation and workup, 15.8g of isosafrole was recovered, with no yield of MDP-2-P.
Anthraquinone is not a useable substitute.
Ah well, it was worth a try.