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experiment:lye and acetone dry tek

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DiMiTriX

DiMiTriX

Rising Star
ok swim is sperimeting this tek with about 20g of bark:he put the powdered bark in a jar with some lye..helf teaspoon and some ml of water,than he washed this mix about three times with acetone.the acetone solution is greenish blueish solution. now he puts some of this solution into about 2 parts of a lye solution and it turned brown orangish colour and there's some yellow stuff floating on top of the solution,he will filter it and report the results.it seems very dirty stuff and will becoe a goo for sure but maybe after recryst it will give nice stuff,as far as acetone isn't a selectivre solvent of theese alkaloids it will give a jungle spice maybe? don't know at the moment the stuff floating on top of solution is brick orange colour :roll:

time to precipitate this stuff from beginning of the tek is about10 min..we will see
 
Acetone will turn brownish orange with just the presence of NaOH.
I'm not sure why this happens, but think there is some reaction between the two that may not be desirable.
 
Eden said:
Acetone will turn brownish orange with just the presence of NaOH.
I'm not sure why this happens, but think there is some reaction between the two that may not be desirable.
Click to expand...
Really??

SWIM never had something similar anytime he had to mix acetone with NaOH.

Maybe it's something to do with the impurities within your or SWIY's acetone and/or NaOH?
 
Could there be an aldol condensation taking place, coupled with further Michael addition?

Well at least that can happen if you try to dry Acetone with molecular sieves which are slightly basic. I do not know if such a reaction could occur at the sheer presence of a base.

Here is some information: Anhydrous Solvents Part 3: Acetone and Molecular Sieves - Bad idea!

Better get that confirmed with someone more knowledgable than me, im just a badger good at digging out information.
 
For whatever reason, I added (clean evap) acetone to (food grade) lye beads in a capped test tube several months ago.
After 3 days (granted, a longer time frame than that mentioned) the acetone took on an orangish tint and lye beads turned brown and started to degrade.

I had no idea what this meant....only that I would never mix the two.

Hopefully its not my acetone or NaOH. :?
 
yeah swim red something about acetone that could become an enolate with lye or strong bases..he concentree the solution at almost a goo and than dropped in lye solution aaand...from coffee cloudy colour it becomes orange and trasparent (!??) after ours nothing at the bottom :cry:
so experiment is failed
 
NaOH can tautomerize acetone or so I thought. Isn't this the mechanism of some base induced aldol addition reactions between acetone and aldehydes?


I'd be concerned about water:acetone miscability and solubility of NaOH in the mixture proposed.
 
Sodium carbonate is pretty weak, and the necessity of drying with use of acetone tends to complicate extractions since it's always possible that the reaction didn't go anywhere near completion prior to drying. Using lye may improve the process to this effect, but the drying process will result in highly concentrated lye solution and just sounds like a bad idea to me.

In any case lime is a strong base and quite effective when used in such a manner, and though SWIM's never bothered with drying lime/MHRB dough (limteks typically use NPS, such as limonene, which doesn't necessitate drying, thus distinguished from dryteks), he imagines it'd work fine given adequate time to soak and react prior to drying.
 
Acetone + lye = aldol condensation -> diacetone alcohol -> mesityl oxide -> acetone trimer -> dimedone, plus further (coloured) polymers. Just to confirm. So don't mix NaOH with acetone for an extraction.

Quote:
the drying process will result in highly concentrated lye solution and just sounds like a bad idea to me.

Evaporating down to concentrated lye solution is tricky and requires far too high a temperature (you would vaporise and/or decompose your spice). The alternative of air drying would, anyhow, form (some) sodium carbonate and sodium bicarbonate by absorption of CO2 from the air.
 
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