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InvisibleEntropymancer
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Looking for feedback - chemistry of DMT extraction explained - too complicated?
    #9178948 - 11/03/08 06:05 PM (15 years, 4 months ago)

I'm in the process of revamping my DMT Extraction Overview (mostly to add in discussion of newer extraction techniques) and figured I'd add a section at the beginning to give a quick chemistry lesson on the principles behind the extraction.

I've simplified things, since my goal is for someone who doesn't have any chemistry knowledge to be able to read it and make sense of it (hence my posting this in the pub).

If any of you care to read it, I'd appreciate some feedback. Does it make sense? Are parts of it confusing or poorly worded? Does it just read like gobbledeegook to the nonchemist?

Here it is:








Background Explanations: How DMT Extractions work

All DMT extraction teks are based on the relative solubilities of the DMT in it's protonated and unprotonated form. What does that mean exactly?

Lets start out with a crash-course some basic chemical principles. If you're familiar with acid/base equilibria and polar vs nonpolar solvents, feel free to skip ahead. All important terms are in bold so you can glance back and check the definition if you forget what  it means.





Acids and Bases

A proton is a positively hydrogen ion, H+. The transfer of protons is the entire basis of acid/base chemistry. An acid is a molecule that can donate a proton. A base is a molecule that can acquire a proton.

Every acid has a conjugate base; for example, when acetic acid (CH3COOH) gives up the proton on its -COOH group (incidentally, this is called a "carboxylic acid"), its conjugate base is the acetate anion (CH3COO-). Thus acetic acid and acetate are called a "conjugate pair". Likewise, every base has a conjugate acid; for example, when ammonia (NH3) aquires a proton, its conjugate acid is an ammonium cation (NH4+). (Ammonia and ammonium are another conjugate pair).

Just a bit of terminology: An when a molecule carries a charge, we call it an ion. If it's positively charged, we call it a cation; if it's negatively charged, we call it an anion.





pH and pKa

The relative concentrations of each member of a conjugate pair in solution is determined by the pH. The lower the pH, the more protons there are in solution, and bases are eager to grab them up. The higher the pH, the less protons there are in solution, and the more eager the conjugate acids are to be rid of them. Low pH solutions are referred to as acidic, while high pH solutions are referred to as alkaline, or basic.

The pH where the concentrations of a base and its conjugate acid are equal is called the "pKa" of that conjugate pair. Above the pKa, more of the molecule exists in its base form; below the pKa, more of the molecule exists as its conjugate acid.

DMT is a neutral (uncharged) base, sometimes called a "freebase" because the uncharged ("free") base can be obtained as a solid. The pKa of DMT is 8.68. Above pH 8.68, it exists primarily in its neutral (uncharged) freebase form. Below pH 8.68, it exists primarily in its positively charged acid form.







Salts

Often the protonated form of DMT will associate with a "counterion". When ions associate to form an complex with a net charge of 0, we call this a salt . Since DMT bears a positive charge, it must associate with a negatively charged ion in order to form a neutral salt. For example, if we acidify a solution of DMT using acetic acid, then the DMT will predominantly assume its charged (protonated) conjugate acid form, and will tend to associate with acetate ion (CH3COO-), the conjugate base of the acetic acid we used to acidify the solution.  We would call the resulting salt DMT acetate. 

So what does all this have to do with extracting DMT? Don't worry, we only need to talk about one more piece of the puzzle to start making sense of it.





Solvents

A solvent is a liquid in which other molecules can be dissolved. In the case of extractions, we're interested in dissolving DMT.  For our purposes, there are two types of solvents: polar solvents, and nonpolar solvents. In polar solvents (like water and ethanol), polar compounds like salts and ions tend to be highly soluble (that is, they dissolve easily), while less polar compounds like hydrocarbons and neutral organic molecules (like DMT freebase) tend to be relatively insoluble (that is, they tend not to dissolve). In nonpolar solvents (like naphtha and dichloromethane) polar compounds tend to be insoluble, while less polar compounds tend to be more soluble. When polar and nonpolar solvents are mixed together, they typically stay seperated as two seperate layers, or "phases". Oil and water is the classic example of this phenomenon.

This is a simplified explanation, but it'll serve well enough to explain the basic principles of the process.





Now let's bring it all back home with respect to extracting DMT: 

In acidic water, DMT exists predominantly in its protonated form, either as a cation or a salt. Since the protonated form of DMT is relatively polar, DMT is quite soluble in acidic water. In alkaline water, DMT exists predominantly in its freebase form.  While the freebase is not particularly soluble in water, it's not so insoluble that it falls out of solution or forms a seperate layer.  But if we were to mix an alkaline solution of DMT with a nonpolar solvent, since the DMT freebase is much more soluble in the nonpolar solvent, much of it will migrate from the polar solvent to the nonpolar solvent.

This is the basis of almost every DMT extraction.

Edited by Entropymancer (11/03/08 06:06 PM)

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InvisibleWoodsCall
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: Entropymancer]
    #9179012 - 11/03/08 06:17 PM (15 years, 4 months ago)

It makes perfect sense, but I'm currently in the second class of my chem sequence (actually learning about conjugates etc right now). 

With the amount of people that fail the regular chem sequence, it seems this might be hard to understand for the 'nonchemist.'


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InvisibleEntropymancer
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: WoodsCall]
    #9179122 - 11/03/08 06:40 PM (15 years, 4 months ago)

Thanks for the feedback. I'm not too worried about it being simple enough that everyone can understand it immediately. The key takehome points are all that really matter for extractors (in acidic solution, DMT prefers to be dissolved in water, in basic solution it prefers to migrate to a nonpolar solvent if given the choice).

I just want it to be simple enough that if someone is curious about the reasons why, they should be able to figure it out from my explanation.

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InvisibleWoodsCall
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: Entropymancer]
    #9179188 - 11/03/08 06:51 PM (15 years, 4 months ago)

I think it's fine then :thumbup:


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Offlinerupertbeaner
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: Entropymancer]
    #9179192 - 11/03/08 06:53 PM (15 years, 4 months ago)

This is making more sense to me...

I saw pictures of DMT extraction and it had a lot of decanting involved because there was separation in layers of the liquids. In that respect, The oil and water example made sense.

I had to re-read the pka and what I got from it was that the pka is the separation of the liquid solvents that there is a acidic layer above and a base layer below?

I'm still trying to get a hold on DMT extraction, the water and oil example is what I took with me.

chem. education: highschool chemistry class + breaking bad season 1

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InvisibleEntropymancer
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: rupertbeaner]
    #9179237 - 11/03/08 07:04 PM (15 years, 4 months ago)

Quote:

rupertbeaner said:
I had to re-read the pka and what I got from it was that the pka is the separation of the liquid solvents that there is a acidic layer above and a base layer below?




No, there aren't seperate acid and base layers. If you add an acid to the water, it's acidic and it's pH drops below 7 (pure water has a pH of 7), and if you add a base it rises above 7. It doesn't form seperate layers though.

The seperate layers come from combining polar and nonpolar solvents (water is polar, oil is nonpolar). The most typical solvents in a DMT extraction are water and naphtha, which seperate because water is polar and naphtha is nonpolar. If the water has a high pH, then the DMT be in its uncharged form, and will tend to migrate into the nonpolar layer.

The pKa of a molecule is the pH at which there's an equal amount of it in its acid and base forms. So in a pH 8.68 solution, half the DMT is protonated, and the other half is uncharged. Above the pKa, there's more uncharged DMT, while below the pKa there's more charged (protonated) DMT.

I'll see if I can figure out a way to make that part more clear in the explanation.

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InvisibleantiPock
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: Entropymancer]
    #9179284 - 11/03/08 07:15 PM (15 years, 4 months ago)

seems pretty concise considering what you cover. Reads well to me and certainly not too complicated. It also conveys a couple of general concepts like the definition of acid and base quite nicely. I would think anyone interested in extraction would appreciate this level of detail as it provides a greater understanding of the "why" behind the steps in various teks.

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Offlinerupertbeaner
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: Entropymancer]
    #9179339 - 11/03/08 07:23 PM (15 years, 4 months ago)

so to summarize:
water(which is polar) with a high ph (>7 = base)
combined with naptha (non-polar) = dmt will goto the non-polar layer because of the ph of the water?

a pH of 8.68 (or more?) will give you the unchanged freebase form of DMT in the naptha?

polar and non-polar = separation of layers.

I'm trying to get a hang on this, but I feel some terms are over my head because I do not have anything to reference them to. I really do appreciate you taking the time to break down the process in layman terms, but this is something I am going to have to spend some time with in order to grasp the whole concept.

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InvisibleEntropymancer
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: rupertbeaner]
    #9179401 - 11/03/08 07:33 PM (15 years, 4 months ago)

Quote:

rupertbeaner said:
so to summarize:
water(which is polar) with a high ph (>7 = base)
combined with naptha (non-polar) = dmt will goto the non-polar layer because of the ph of the water?




Yep. At high pH, since the pH is substantially higher than DMT's pKa, that means the DMT will be predominantly in its uncharged freebase form. The freebase is more soluble in nonpolar solvents than water, so it goes into the nonpolar layer.

Quote:

a pH of 8.68 (or more?) will give you the unchanged freebase form of DMT in the naptha?




A pH of 8.68 gives a 1:1 ratio of uncharged to charged DMT. A pH of 9.68 gives a 10:1 ratio of uncharged to charged; pH 10.68 gives a 100:1 ratio and so on.

Quote:

polar and non-polar = separation of layers.



Yep.

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Invisibletruekimbo2
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: Entropymancer]
    #9179432 - 11/03/08 07:40 PM (15 years, 4 months ago)

if the point is to teach people the science behind a/b then its fine.

i don't know, if you're just trying to give people a general idea i'd say its pretty bad.  i doubt the average person would want to read that.  not using science terms would be a big help.


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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: truekimbo2]
    #9179454 - 11/03/08 07:46 PM (15 years, 4 months ago)

don't dumb it down. There are plenty of other sources for the non-scientifically inclined, not that this should require beyond a HS chem 1 anyway, and less if one was at least somewhat scientifically literate or even wanted to be.

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Invisibletruekimbo2
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: truekimbo2]
    #9179478 - 11/03/08 07:51 PM (15 years, 4 months ago)

Quote:

i don't know, if you're just trying to give people a general idea i'd say its pretty bad.  i doubt the average person would want to read that.  not using science terms would be a big help.




Quote:

if you're just trying to give people a general idea i'd say its pretty bad.  i doubt the average person would want to read that.




Quote:

  i doubt the average person would want to read that.




Quote:

the average person




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InvisibleantiPock
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: truekimbo2]
    #9179585 - 11/03/08 08:09 PM (15 years, 4 months ago)

I'm sorry Truekimbo I mean no offense. I guess I just like the idea that something folks are interested in - DMT extraction, can also serve as a learning tool for broader concepts of science. I try not to assume that the average person is uninterested or incapable of thinking about these things, though I'm sure some are.

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InvisibleEntropymancer
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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: antiPock]
    #9179757 - 11/03/08 08:40 PM (15 years, 4 months ago)

Yeah antiPock, that's my line of thinking.  Sure, you can do a DMT extraction without understanding any of the science behind it, but it also serves as a perfect opportunity to learn some practical chemistry.

I don't intend to dumb it down any more than it is. I'm simplifying things by skipping over the details of liquid-liquid extraction and the partition factor, and the fact that there are equilibria between dissolved and precipitated neutral species. That's all a level of detail beyond what's needed to understand the process.

But I think that if the average person is actually interested, they're entirely capable of understanding the basic chemistry behind acid/base extractions.

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Re: Looking for feedback - chemistry of DMT extraction explained - too complicated? [Re: Entropymancer]
    #9179820 - 11/03/08 08:49 PM (15 years, 4 months ago)

Looking great. I can't wait til you're done with it.


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