i just remembered a post from a couple years ago that might help you:

h**p://www.psychonaut.com/post-35536-194553.html?f=43#p194553

Okay, I know that the Wacker oxidation with 1,4-benzoquinone isn't the most popular reaction in the world due to the fact that most aspiring bees have as much trouble getting 1,4-benzoquinone as they do safrole but Moriarty gives advice to some aspiring bees and they sometimes experiment for him. So here's the latest trial in reducing tar and hopefully keeping yields decent. So I gave these instructions to someone and they performed the following experiment:

1. They Purified a kilogram of brown camphor oil (sassafras oil) by crystallization alone. Don't do this. Without first distilling only ~600 grams was obtained. From past experience it is known that at least 800 grams exist in this oil. Plus it had to be crystallized and melted and recrystallized like 5 times before it was considered pure.

2. Density was checked. I had this fledgling bee buy decent graduated cylinders and test their accuracy with distilled water. The 100 grams of distilled water was just above the 100ml mark so a new mark was placed on the graduated cylinder and the suspected olefin was measured out. 100ml weighted 109.6 grams at 25C. I believe the density is 1.10 at 25C and 1.096 at 20C so there was some confusion but the sample was considered pure.

3. Five (5) grams of palladium chloride was added to a 6-liter flat bottomed flask with 350 grams of 1,4-benzoquinone.

4. 1200ml of methanol and 150ml of DH2O was added and stirring began.

5. Stirring was allowed for 2 hours although I can almost assure you this is not necessary.

6. 600 grams of some olefin that has a specific gravity of 1.096 is weighted out and ~200ml of methanol is added so as if to make ~750 of olefin/methanol solution.

7. This was added in 150ml portions every 12 minutes until gone.

0:00 Hours 150ml of the solution is added, some discoloration noted but no real heat

0:12 Hours another 150ml of the solution is added and a small amount of heat is noticed

0:24 Hours another 150ml of solution is added and it begins to get warm

0:36 Hours another 150ml of solution is added and reflux is obvious. This reaction has achieved at least the 60C boiling point of methanol.

0:48 Hours another 150ml of solution is added and reflux gets hot and heavy almost like an Al/Hg amalgamation with nitromethane

1:00 Hours things are not refluxing anymore but the flask is still hot.

2:00 Hours a noticeable decrease in heat has been observed.

3:00 Hours cooled off almost completely. I asked him to let it stir for the evening with no heat.

Tomorrow I will ask him to extract 3 rimes with 500ml of DCM, Wash and distill. Hopefully the yield is good.

Moriarty

When all the ketone was distilled my experimenter claims he distilled 594.9 of ketone. This from 600 grams of olefin and he claims to have possibly lost some fraction of DCM/ketone in the washes. He probably did. Anyway he said work up involved the following:

1. Flooding the reaction mixture with 1000ml 15% HCl(aq) so as if to shoot for an overall 5% HCl solution when the bi-phasic mixture was interacting.

2. Extracted with DCM 3 times with 500ml each time. The total extract was a little over ~2.1 liters.

3. Washing with 1000ml of 5% NaOH 5 times before it was "clean"

4. Washing it once with saturated NaCl

5. Passing the DCM/ketone throught a funnel fitted with a filter and ~60 grams CaCl2

The total distillate was 594.9 grams of a ketone that had a density of 1.182. This means the estimated purity is ~77%. The rest is isosafrole. The yield to ketone was ~458.1. That's Approximately a yield of 84%. There is still some tar but not much for this sized reaction.

So, even though the tester was not thorough we can probably conclude that external heat is not necessary and that tar is reduced but just ever so slightly with less 1,4-benzoquinone.

nice work Moriarty!
any reason why the 15% HCl instead of 10%?

Shear solvent value. It get's hard to work with 4 and 5 liters of liquid at a time. So I suggested a liter of 15% be added to the 2 plus liters of solution so the whole thing would be around 5% when the bi-phasic layers were interacting (stirring as shaking in a 4-liter sep funnel is near impossible at these volumes). When the HCl(aq) is added the organic and aqueous layers separate immediately. So the strength of the aqueous layer is irrelevant until the layers are shaken or stirred to create interface. At that point I wanted my friend to have something similar to 5% HCl(aq). Anyway, that was his results as he reported them to me. I don't know that my suggestions answered any questions but it was worth a try.

Moriarty

damm...i was reading in deep that article Jon´s makes reference posted on the Hive on the 98,about that wacker using Palladium acetate and H202 on tert butyl alcohol....:200 gr safrol,only 1gr. Palladium acetate!... with near 80% yields and almost no necesary post distillation....with same time reaction(6 hours reflux) and way much more clean work-up...Man..if that works it´s the way to go without doubt t all!Sounds like a dream to go to ketone!

Yeah Neil,i know vacum distill it´s a must.....i don´t have a strong pump,but does the work to distill the goods without too much problem about 190ºC.
   I supossed of course that reducing directly the dirty ketone it will be a waste,because saddly,seems there  is no way the crap don´t go into the final toluene extractions and finish on not alowing crystallization.
    Well,about that palladium acetate with tert-butyl alcohol wacker....i was looking at that solvent few minutes ago at my chemical suplier for curiosity....and ...it´s posible 10 ml/gr. cost near 30$? ...if i´m not mistaken ...if it´is real...and that reaction with 200 gr safrol uses 10000ml.....well....there would be a must found first a substitute to that solvent....

Prep for PdAcO2 is at the end.  Pd sponge, glacial acetic acid, and nitric acid (just enough to oxidize).  Definitely cheaper than buying it.  

Interesting to note:

They (pd carboxylates) are soluble in a number of  organic solvents, but  decompose when warmed with  alcohols, giving palladium  metal ; prolonged boiling in other solvents gives the same result.

If thats true then its quite possible the active catalytic species is actually Pd nanoparticles.  Does anyone have any info on wacker in organic solvents w/ triphenyl phosphine ligands?  I bet you could reduce solvents volumes a ton.

Well,seems that things about benzo wacker must have to wait some days more....i had all my distillng set-up ready to distill safrole,and when it come moment of apply vacuum,i powered  on the vacuum pump(stored on room like 3-4 months unused since i was out of chemistry work) and....was fucking dead!...i inspected it outside,and saw screws hard oxidated....bad things....i opened the pump(with much troubles)...and saw motor totally oxidized and corroed.....When i saw metal things on my lab-romm getting oxidized with time because the use of hcl gas to crystallize,i couldn´t imagine how hard can attact our lab equipment,no matter if you extract to exterior.Minimal losses can produced that od course.The hotplate stirrer was making bad noises too,and since continue working,seems it damaged too... .
   well,i have bought now ,since i have all prepared again,a second hand air conditioning vacuum pump,those that works with oil,for a minimal price(80$),that i know pull near 700mmHgvacuum.Good vacuum ,but read that pumps suffers from solvent vapors and  water that mix with the oil when vacuum distill,and posibly get damaged on few distillation runs,but was the only thing i can plan now,because use of an aspirator it´s not posible because water sink if way far from my room to controll flow...
    Well guys,...have you any experience with this type of oil pumps.i will receive it in 2-3 days.It´s a 2 stage rotary,that have vacuum regulator( i suposse),but not gauge,and anti-suck valve have read on technical specifications.so posible i will have to apply vacuum by "hear" of motor and see how bubbles grow on distillation flask,....really i new adventure .
   I plan put a vacuum trap betwwen vacuum outlet and pump trying to minimize pump´s oil contamination,but don´t know what to expect about that,Posibly first will be distill water to see how hard it pulls,and posible problems with suck-back or too much vacuum to my glassware.
   Well,like allways,any advice about using that kinds of pumps will be great.Thinking on all the process,i think only will have to distill safrole,water,ketone,methanol and mostly toluene,....We will see,,,,

just distill the methanol without a vacumn

any reason why most of the scale up threads on the hived dealt with the performic?

Not emulsions at all Jon.Posibly i explained little wrong....
    After distilling methanol and cold,the mix(ketone+organic crap) polimerized on solid state,not very hard,but polimerized..Added the hcl solution,and becomes on 2 phases:typical red-wine acid water layer and bottom layer,that usualy falls on liquid consistency,but because no methanol on solution think,falled like that consistency of petroleum on water,like volcanic magma,....decided to  add again the methanol distilled,and consistency turned on more liquid and ready to extractand much better when toluene contacted the organic layer.Extracted quickly and without problems 3 times with toluene without emulsions,3 Naoh washes without emulsions too,and this afternoom i´m ready to distill the  about 2 litres toluene and then the ketone.

    I have in mind a way to improve that reaction about work-up....and posibly get wrong again
    I think, after methanol distillation,add toluene with mix still warm without letting polimerize,trying to  disolve it using minimum toluene,....and since i think,the acid solution only make fuction off extract the methanol from the toluene???...it´s posible?,....go directly to the NaoH washes....resulting on like 500-700 ml toluene and not the 2 litres i need normal with big amounts of ketone,2 liters acid solution,...
    Can be posible skip the acid wash ?can let on the toluene something bad to the ketone distillation.I´m only dreaming on new things....

AHHG....my fucking hands are brown... .
   Well,i was experimenting these days with diferent alternatives on the benzoquinone wacker....and ...for my surprise,...i´m a now a DCM guy!.
    First,that benzoquinone wacker on methanol,using 2,5 gr. palladium,175 gr Benzoquinone,...300 gr safrole....that decided to distill methanol to reduce water solution on extractions....that finally extracted with toluene as usual....only yield 150 gr. ketone....so a 50% yield.Not very good f course,posibly decision of boil methanol can be related,...but i have discovered....most of my looses about yield are about that crap that make ketone distillation very hard,almost imposible when are left on the flask 50-75 ml ketone/crap.
    I was a fan of toulene because extractions and washes are really easy.but of course,that crap carried with the toluene makes last 50 ml ketone imposible to boil,no matter i was using a strong vacuum that make boils ketone about 125ºC...there is no problem about vacuum...it´s all related to solution gets so viscous that ketone it´s not able to come over more and end polimerizing on the flask.
   My last procedure i can say it´s a great succes.
   Decided to exchange methanol for dimethylformamide like on the begining.The mix get into solution very fast,not relally as exothermic as methanol....not necasary palladium pre.strirring...i make that batch:
   -2,5 gr palladium.
   -175 gr benzoquinone
   -100 ml water(a little more than recomended)
   -600 ml DMF....all mixed about one hour only.
   -300 ml safrole+100 ml DMF added on 75 ml portions each 12-15 minutes.
   -8 hours reaction.put on freezer overnight and vacuum filtered next morning.
   -flooded with 1,5 litre 10% HCL,stirring like 5 minutes until oil falls from acid solution.
   -COLLECTED STRAIGHT THE BLACK OIL FROM THE BOTTOM
   -EXTRACTED ACID SOLUTION WITH 500 ml DCM ONLY ONCE(I WAS SLOOPY)
   -COMBINED OIL WITH DCM EXTRACTION.
   -WASHED 2 TIMES WITH 500 ML 7´5 % nAOH SOLUTION.
   -WASHED ONCE WITH CLEAN WATER.
   -DRIED OVER BUCHNER FULL OF CALCIUM CHLORIDE.
   -DISTILLED UNDER VACUMM....FEW GRAMS  ISOSAFROLE AND THEN.....275 GR CLEAN  GREEN-YELOW KETONE....VERY VERY EASY BECAUSE THE CLEAN DCM EXTRACTIONS.
    -REDISTILLED FRACTIONAL:250 GR I THINK VERY PURE KETONE.
   
       So,...i was talking shit about DCM here to extract time ago,because the freaking emulsions.But extracting with DCM seems much better than toluene because the so clean extractions you get,....Only you have to do it´s  stir slowly with care the two phases,almost with love ;without shaking....and you will see DCM separating quick and clean perfectly...same with water washes....Important too the quickly evaporation of DCM before ketone distilling inetead toluene,and most important:MINIMAL LOOSES ON KETONE DISTILLATION BECAUSE MECHANICAL PROBLEMS WITH STIRRIRING/TOO MUCH VISCOUS SOLUTION THAT HAPPENS WHEN USED TOLUENE TO EXTRACT.
     And i still thinking yields using DMF instead methanol are always better in my little experience.
   Of course,one have to use solvents that are to more easy and cheap to get,but on my experience,since now,...i will stick with DMF and DCM.
 
  PD:NEXT TIME I WILL RUN THE PALLADIUM ACETATE,TERT-BUTYL ALCOHOL,H202 SYSTEM,....BUT I HAVE AN IMPORTANT QUESTIONS:
     WHAT KIND PALLADIUM ACETATE CLAIMS ARTICLES TO USE:
      -PALLADIUM(2) acetate (like near 70 $ gram)=2 molecule palladium with 1 acetate groups=expensive
      -PALLADIUM ACETATE(2)....same price as palladium chloride.1 molecule palladium with 2 acetate groups=relativly cheap nd more easy to find.
   An answer about that palladium acetate question will be great  both for me and others,,,because i think a review of this system...if it works as said,....must be great
    Seems nomenclature on that it´s little tricky here.suposed

 
   

i don´t understand what the hell matters with you shake...are you joking  me?
   I was allways gratefull about all info i get from  this forum...from you,Methyl,Neil,Jon,Sedit....but don´t have any ethical need to remember you all time how great are your contributions if you think there are so great....much more less if you act like a frustated kid sometimes....a thing that i really hate with passion.
   i`m here to learn....and make others learn if it´s posible from my experiments....not only to get attention from other members.
   But if it´s important to you...
   Finally,i remember you my vesp name is sassa,not sassy.