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Extraction with Acetone Options
 
benzyme
#1 Posted : 12/21/2019 4:22:10 AM

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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:

Quote:
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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Tony6Strings
#2 Posted : 12/21/2019 5:06:01 AM

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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?
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leratiomyces
#3 Posted : 12/21/2019 7:00:55 AM
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benzyme wrote:
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:

Quote:
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.



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?
 
benzyme
#4 Posted : 12/21/2019 4:06:56 PM

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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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benzyme
#5 Posted : 12/21/2019 4:10:14 PM

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https://ibb.co/Qn6SCGQ

top layer acetone with the free base amine, bottom layer aqueous phase, pH 12.62.
salt was added to further resolve the interface between the biphase.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
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Jees
#6 Posted : 12/21/2019 4:26:30 PM

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Interesting.

Will the caustic not dry the acetone as a welcome effect? If not why?
 
benzyme
#7 Posted : 12/21/2019 4:28:04 PM

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that's a great question, and I honestly don't know.
But I have noticed micelles migrate out of the acetone layer. they are no doubt aqueous.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
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benzyme
#8 Posted : 1/1/2020 8:07:57 PM

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another experiment, with base and acetone.
benzyme attached the following image(s):
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Attachment-1.png (137kb) downloaded 150 time(s).
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
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Jees
#9 Posted : 1/2/2020 10:51:15 PM

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Unseen porn Rolling eyes
 
benzyme
#10 Posted : 1/3/2020 3:51:13 AM

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"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
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sbios
#11 Posted : 1/4/2020 11:17:44 AM

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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.
 
benzyme
#12 Posted : 1/4/2020 3:21:05 PM

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Calcium Hydroxide doesn't dissociate well in water. I'd take the pH to 13-14, to avoid any aqueous interaction with acetone.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
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doubledog
#13 Posted : 1/4/2020 9:36:08 PM

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Does this mean that water will separate from acetone after addition of base?
Similarly like IPA from water when salt is added?
 
benzyme
#14 Posted : 1/4/2020 11:36:35 PM

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yep
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
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downwardsfromzero
#15 Posted : 1/11/2020 7:53:45 PM

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Catching up on my holiday backlog:
Quote:
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.
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.
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fathomlessness
#16 Posted : 1/12/2020 12:12:36 AM

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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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