O2 wacker problems!

[Snakebyte]

Okay...I dreamt of an O2 wacker and after 2 days of shaking and stirring there was only about 5 psi of O2 uptake! I followed Krz's O2 wacker perfectly with only a few changes.  Instead of stirring I used a professional paint shaker for 1 gallon cans.  My vessel was a 1 gallon pesticide sprayer.  This thing shakes like crazy!  This vessel holds a perfect seal too.  When i tested it, it held 40 psi for 24 hours with absolutly no measurable loss.  I used O2 from a welders tank...purging 3 three times at the start.  I used PdCl (powdery brown)from chem supply.  I used DMF as the solvent and used the same amount of water as the synth says. I used Hellmans v1.0 synth for my CuCl2 and I'm wondering if that was the problem.  My end CuCl2 looked like little green rocks like the size of fishtank gravel.  It looked and felt perfectly dry but was a rich green color.  I thought that if it was green it should be wet and slimey from water absorbtion and that when dry it should be brown.  When left out my CuCl2 to open air it didn't change color or texture.  It was still hard dry green rocks. Does that CuCl2 synth work?  Anyway, I suspected that my CuCl2 was the problem because everything else was done exactly like the synth says.  So after a day of shaking and hardly any O2 uptake I made up some CuCl2 from Osmium's synth by mixing copper sulphate solution with calcium chloride solution.  I then added that to my reaction contents and shook for another 2 hours.  Still no uptake.  So then I removed all the water under vac because Osmium(or someone) says water just slows the reaction down.  Then shook more...still nothing.  Tried stirring..still none.  What the hell is going on here??  Should I have removed the old (supposedly) CuCl2 from reaction before adding the new stuff?  The color has changed darker so far and it does smell sweeter so maybe the reaction is pushing forward slightly but only about 5 psi worth. Pls someone help!

[Snakebyte]

BTW, i dreamt that my safrol was purified by feezing 3X.

[Osmium]

For the DMF O2 Wacker you need CuCl, not CuCl2!

The O2 Wacker with an alcohol solvent uses CuCl2, and in this reaction too much water is detrimental. This reaction also needs to be heated, you won't get much of a reaction at ambient temperature.

[Snakebyte]

Krz's write-up on Rhodium's page with DMF as solvent uses CuCl2.  Grouch is the one that uses CuCl and his yeilds are less.  Niether one of the write-ups mention the use of any external heat. I'm not second guessing your judgment Os but how did u come to this conclusion?

[Snakebyte]

Well, needless to say there was nearly no ketone.  What is the best way to go about salvaging my palladium? And I did UTFSE, there wasn't much.

[ephemeral]

if one were to theoreticaly use the formula and technique exactly as descrtibed by Krz post at Rhodium, she might get no results at all, as snakebite.  After extensive use of TFSE, it seems the details of that post were removed by the author.
   Other posts indicate shaking heavily may help o2 absorbtion, while CuCl rahter than the dihydrate of Cucl2 is the answer.  Then there is the DMSO suggestion.
 I cannot seem to find a complete post of any success with the o2 wacker, sans PBQ, except for the shake it and leave it under the bed for 18 hours listing.
    If heating will drive yields towrds P1P,is there any way to salvage snakebites unreacted mix?  Will shaking while at 35-40 psi create the uptake after that same rxn mix has seen no activity but remained under o2 press for 48 hours? 
 It would be a damn shame to waste so much of so many critical reactants without trying a save.  Any follow us advice would no doubt be greatfully appreciated by all at such a sticking point.

[chilly_willy]

Benzoquinone

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/benzoquinone.html):

[tryin]

Here is a thread where some bees talk about successful dreams of the O2 wacker. Pupilage has a really good write-up. In reply to:

"I cannot seem to find a complete post of any success with the o2 wacker, sans PBQ, except for the shake it and leave it under the bed for 18 hours listing."

Post 382474 (missing)

(majic22: "questions about KRV/SRV METHANOL 02 WACKER method", Newbee Forum)

[Bond_DoubleBond]

benzo wackers are more pdcl2 efficient, don't require shaking, and get just as good yields.

you can make kilos of benzo in a couple hours of you scale up the following procedure or run several concurrently or both.

Post 473279

(Bond_DoubleBond: "Big Breakthrough for Benzo Bees", Methods Discourse)

[Snakebyte]

Ok, I finally dreamt of this O2 wacker again and used CuCl this time instead like Os suggested and NO water.  Same equipment and procedure.  Still no oxygen uptake!  The only thing I can think of is that my palladium is photography grade.  Does anyone know if that would be the problem?  I've tried DMSO and DMF and this is what happens.  Should I just distill of the DMF and do an alcoholic wacker?  I've spent alot of time and money on this apparatus so I'd like to get to the bottom of it but I've almost had it.  If I were to salvage my palladium for a p-benzo wacker should I just wash out the CuCl with water and then filter out the palladium?

[Bond_DoubleBond]

get yourself some formic acid and some hydrogen peroxide.  performics are much easier.  and if you do an hcl rearrangement, your yields can be as much as 75-80% if you distill at a small scale.  plus dcm is easier to aquire than dmf or dmso, you can get usp grade sodium bicarbonate at your local grocery store, and koh can be had dirt cheap with some internet scouring.

make the switch.  swim did, and he'll never go back.

[Snakebyte]

I've always wanted to do a performic but I can't seem to find the formic acid.  I have access to any solvent and most other chems but not formic acid.  If I was to continue my wacker as a benzo wacker would it be ok to leave that cucl in there or would I have to wash it out along with the palladium?  What would be the best way to do that?

[Tdurden969]

A peracetic is (arguably) just as good as a performic..

Surely if you have access to most any solvant you can get your hands on concentrated acetic acid of some kind.

I'm sorry, I don't have an answer to your question.