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Extraction with Acetone

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benzyme

benzyme

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I'm gonna set the record straight, because there seems to be a misunderstanding about acetone: it can be used as an extraction solvent.

on the DMT sub, people seem to think acetone mixes with basic water, and will not separate....

WRONG.

I explain:

Acetone only has one proton acceptor, and no donors. It can only participate in H-bond interactions, as a proton acceptor. A basic phase is hydroxanion-rich, and cation-poor (lacks protons), and those hydroxyanions disrupt interactions between acetone and water molecules.

the logp of dmt is 2.3. Naphtha is around 4. Acetone is 0.3. DCM is 1.6, Toluene is 2.3, Ethyl Acetate is 0.7, Acetone is -0.1. Based on this data, DMT is most soluble in toluene and dcm. It's actually soluble in acetone, and ethyl acetate (another polar solvent). Synthesis procedures actually describe extraction/chromatography elution with EtOAc.

I've extracted with all solvents mentioned. I selected acetone, because like naphtha it lends itself well to freeze precipitation, unlike toluene and dcm.
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Good news for anyone wanting to do a straight to enhanced leaf tek. So, the acetone floats on top of the basic like other NPS, say like Naphtha?
 
benzyme said:
I'm gonna set the record straight, because there seems to be a misunderstanding about acetone: it can be used as an extraction solvent.

on the DMT sub, people seem to think acetone mixes with basic water, and will not separate....

WRONG.

I explain:

Acetone only has one proton acceptor, and no donors. It can only participate in H-bond interactions, as a proton acceptor. A basic phase is hydroxanion-rich, and cation-poor (lacks protons), and those hydroxyanions disrupt interactions between acetone and water molecules.

the logp of dmt is 2.3. Naphtha is around 4. Acetone is 0.3. DCM is 1.6, Toluene is 2.3, Ethyl Acetate is 0.7, Acetone is -0.1. Based on this data, DMT is most soluble in toluene and dcm. It's actually soluble in acetone, and ethyl acetate (another polar solvent). Synthesis procedures actually describe extraction/chromatography elution with EtOAc.

I've extracted with all solvents mentioned. I selected acetone, because like naphtha it lends itself well to freeze precipitation, unlike toluene and dcm.
Click to expand...
Click to expand...


Can you point out some data that shows how quickly the solubility of water in acetone drops off as you increase the molarity of sodium hydroxide?
And are you not concerned about the self condensation product of acetone contaminating things?
 
I'm not a data cruncher, I do the work.
After extraction, I do the same as I would with DCM...pour the acetone in anhydrous MgSO4. What I can provide is LCMS data, there are no adducts.

what I illustrate is that you can doubt, naysay, theorize why it wouldn't work...but won't know until you run the experiment.
 

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I tried to use Acetone once with a dry tek using Ca(OH)2 as base. The muddy substance turns to more mushy and the whole thing became rather unable to pull the solvent. I suppose Calciumhydroxide isn't so good pairing with Acetone or there is something amiss I didn't notice.
 
Does this mean that water will separate from acetone after addition of base?
Similarly like IPA from water when salt is added?
 
Catching up on my holiday backlog:
the logp of dmt is 2.3. Naphtha is around 4. Acetone is 0.3. DCM is 1.6, Toluene is 2.3, Ethyl Acetate is 0.7, Acetone is -0.1. Based on this data, DMT is most soluble in toluene and dcm.
Click to expand...
There are two values listed for acetone. They're not that different but still, which is the 'correct' value? Presumably the latter, as wikipedia lists it as being -0.16. MEK has logP = 0.37 so that may explain the first value given.


Thanks for the useful note on miscibility variation with pH. I've noted phase separation also occurs with aqueous IPA over sodium carbonate.
 
My question to is how will this play out in an extraction with bark/leaves effectively? If one were to dry a sodium carbonate paste with bark/leaves and immerse in acetone then surely the acetone would become saturated with plant oils and limit the amount of dmt solubility? (is naphtha not less selective for oils than acetone?). Is it also seems problematic because of acetones lower solubility for DMT than water? (and from memory naphtha perhaps?).
 
fathomlessness said:
My question to is how will this play out in an extraction with bark/leaves effectively? If one were to dry a sodium carbonate paste with bark/leaves and immerse in acetone then surely the acetone would become saturated with plant oils and limit the amount of dmt solubility? (is naphtha not less selective for oils than acetone?). Is it also seems problematic because of acetones lower solubility for DMT than water? (and from memory naphtha perhaps?).
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I think the point was that acetone just can be used as an extraction solvent, not that it is a good extraction solvent for ACRB/MHRB mother liquors.

I am not sure how well acetone picks up plant oils, but usually recrystallization will get rid of most of the oils.

If the extract is too contaminated, then mini-A/B is the way to go.
 
Acetone is the best! (Btw if you are curious about etymology, the word is derived from the mystical experience from the alkaloids it pulls, in which your ass is at one with the universe. Hence it is called "ass-at-one" [unfortunately often mispronounced these days as ass-uh-tone].)

To avoid pulling out the worthless plant junk, first you need to use some NPS on your basified bark. Then you're ready for the acetone.

If you leave the acetone in the bark for a while and keep it warm, at a high pH, you'll pull a lot more than just DMT+NMT. With Acacia you'll pull a red liquid I call metta. With mimosa you'll pull various tryptamines and some goo that feels like an opiate when vaped.
 
moyshekapoyre said:
...To avoid pulling out the worthless plant junk, first you need to use some NPS on your basified bark...
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Do you mean defatting like a NPS on an acidified bark? I'm just wondering if this was an editorial error or not.
 
Jees said:
moyshekapoyre said:
...To avoid pulling out the worthless plant junk, first you need to use some NPS on your basified bark...
Click to expand...
Do you mean defatting like a NPS on an acidified bark? I'm just wondering if this was an editorial error or not.
Click to expand...

How about an acetone wash of the dry powdered bark? Assuming the natural DMT salts are not soluble in acetone that could clean things up for the basified pulls (but may not be effective if the cell lysing is important for acetone - could be:twisted: worth a try).

- Warm acetone soak/wash
- STB
- Acetone pull
- Reduce/Freeze for FB or Salt with FASA

It looks like basified acetone pulls may work for mescaline by the way (salting out of acetone is done by sulfuric). Experiments there are in progress.
 
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