Author Topic: wacker distillation conundrum  (Read 133 times)

akcom

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wacker distillation conundrum
« on: October 20, 2010, 10:57:04 PM »
A post-wacker reaction solution was distilled under vacuum to yield an almost clear solution with only a hint of yellow.  The density was approximately 0.98g/mL and the compound distilled over at 86C (strength of the vacuum unknown, unfortunately).  The solution smelled slightly of the original safrole.  Any ideas how I can figure out the isosafrole/MDP2P content of this solution?  I'm wondering if what I've got even has MDP2P in it to begin with.  I'm not familiar with the smell of MDP2P so I can't say anything on that end. Comments and suggestions welcome.
« Last Edit: October 20, 2010, 10:59:19 PM by akcom »

RoidRage

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Re: wacker distillation conundrum
« Reply #1 on: October 20, 2010, 11:05:34 PM »
The smell of the ketone is definitly different. Some says it smells like flowers. Density of MDP2P is about 1,2g/ml if I remember correctly, and safrole is 1,096. Considering that your distillate's density is under both, there is definitly something else in the mix,

As for the color, I've noticed that it depends on which solvent you use for extraction. I do not know the exact reasoning behind this. Ketone extracted with DCM is normally much more anti-freeze looking, while ketone extracted with toluene is normally much lighter in color. Only a hint of green. I rechecked this a couple of time, and it always happens. Result is always the same though ;D


NeilPatrickHarris

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Re: wacker distillation conundrum
« Reply #2 on: October 22, 2010, 12:00:51 AM »
swim always uses toluene to extract his ketone.  it is always bright fluorescent yellow and has a lovely floral scent.  here are some densities for you:

safrole: 1.096 g/ml
cis-isosafrole: 1.118 g/ml
trans-isosafrole: 1.206 g/ml
mdp2p: 1.21 g/ml

that density you measured wouldn't explain any typical mixture of safrole/isosafrole/mdp2p as any mixture of those 3 would be at least safrole's density or higher.  to get less than safrole's density it'd seem you'd have to have MeOH in it would be the only explanation, but more likely a better explanation is perhaps the volumetric device you're using isn't very accurate?  another idea is that this unknown oil is another natural oil in the essential oil from whatever plant source the EO is from, what type of oil were you starting from, albidum?  is there a chance that the sassafras oil was a fragrance oil and not an essential oil?  a sodium bisulfite/metabisulfite test might help also.
« Last Edit: October 22, 2010, 12:04:01 AM by NeilPatrickHarris »

Oerlikon

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Re: wacker distillation conundrum
« Reply #3 on: October 25, 2010, 07:29:18 PM »
One hint from another topic,color of MDP-2-P depends on number and
concentration of NaOH washes,light exposure,impurities.
It can range from tansparent-yellowish to most common fluorescent green up to
blue(uncommon but happens if you use MeOH instead of DMF) and red(polymerized crap)

Of all the solvents I used xylene works far best yielding green fluorescent color
that doesn't change over time and smells much less intense than safrole,it has specific smell like
one brand of old bubble-gums. After extracting with toluene it changed from green to yellow,
and DCM extract was far worst and impure.

MDP-2-P dissolves plastic aggressively so if you have even traces of it in your final
product try it that way.

Other than high viscosity,I noticed fluffy crystals like mini feathers in keton that stays in freezer,
if someone knows what that means...!?
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director of sound

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Re: wacker distillation conundrum
« Reply #4 on: October 25, 2010, 07:45:27 PM »
every time swim does anything and gets to his freebase goodies he neutralizes (slightly acidic 6-5ph) with 10% HCl and extracts the left over P2P's and iso's with the appropriate solvent then basify the solution again to extract the goodies which is then dried and gassed. you could try re distilling but place careful control on the temp. creep it up little by little untill some distillate comes over and use a vigreux fractionating column before your condenser. pretty much as soon as you see a drip form on you thermometer stop increasing the temp and collect that distillate fraction, then slowly increase again untill the next fraction comes over and so on untill nothing is left but residue. it helpful to wrap the vigreux in insulation so it stays warm. you dont want stuff to condense in there.

Oerlikon

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Re: wacker distillation conundrum
« Reply #5 on: October 26, 2010, 11:25:50 AM »
No need to redistill, it is waste of time and product.
Extract it with some fast evaporating solvent if you are eager to get pure freebase.
Washing solvent+freebase with low conc. HCl and evaporating wash is the safest
method and you extract all you got.

Like distillation is not enough of complication, why you use vigreux fractionating column!?
BP of amine and ketone are different enough.
Some people use it even to distill even safrole!
I mean if you distill if from the camphor oil than has few fractions sure,it has sense,but if
you distill sassafras oil which has safrole as lowest boiling fraction and some tar that is
plain retarded! It unnecessarily prolongs process and degrades product.
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