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Solubility of oils

Migrated topic.

saphdmt

Rising Star
In general, oil is insoluble in acid, and soluble in bases.

However when doing A/B extractions we do not have an oil layer in our acidic MHRB aqueous solution. But the plant oils sure do make their way from the acidic aq sol to the basic aq sol and then to the naptha.

Why are these oils soluble in both acidic and basic aq solutions?

What exactly are these oils that end up messing up our final product? i.e. what are their names, what is their molecular structure? (Im trying to better understand the chemistry in action here)

Tyvm!
 
My understanding is that a lot of the plant waxes & oils are very soluble in acidic conditions.

Of course, oils are more soluble in NP solvents than in any polar environment (irregardless of acidic or basic conditions) so they like to go there...
 
saphdmt said:
In general, oil is insoluble in acid, and soluble in bases.

I am not sure where you get this notion, but this is wrong.

Oils, generally speaking, are hydrocarbons. They contain mostly CH2. The classic oil is what you are familiar with, Naphtha, which is just a mixture of aliphatic hydrocarbons. These are insoluble in all polar solvents. Acids and Bases, in aqueous as ion's are extremely polar. So they are definitely insoluble.

When you start to get into plant oils, fats and waxes. Your not talking about straight chain hydrocarbons anymore, but they are still primarily CH2 and behave the same way.

Plant oils, fats, are a mixture of fatty acids and esters, meaning long chain CH2's with a polar ester or carboxylic acid at one end. Steric acid for example. As well, these esters can be cleaved into their acids. Carboxylic acids are more soluble in basic solution since they can be ionized. What your left with is a molecule that is polar on one end, and non polar on the other. So it doesn't really dissolve well in either. What you get is a soapy mess.

Here is an experiment for you, take some plant oil, say peanut oil, put it in a jar with some concentrated NaOH, shake it up well, then let it sit for a week.

Thing with rootbark, especially MHRB, it doesn't contain very much fats and oils. That's why the extraction can be done so easily with high purity. It contains a lot of other things, polyphenols, tannins, maybe smaller chain or aromatic carboxylic acids, all these are nicely soluble in basic solution.
 
endlessness said:
What oils are you saying "generally are soluble in bases"?
Google "is oil soluble in acid"; first result.

endlessness said:
Whats the evidence that some oil ends up in your final product?
Fz0lut2.png


endlessness said:
Whats your criteria to call an end product 'messed up'?
Having goo in the final product, not crystalline; wet.

Thanks everyone! Excellent answers!
 
That link is misleading.. its not that bases dissolve oils per se, but rather only some bases will saponify some oils which will make them partly mix with both the non polar (oil) and the polar (watwr) layers. But many bases wont do that and some oils neither (thankfully, otherwise naphtha would mix with lye solution, or vegetable oil extractions wouldnt work with sodium carbonate as a base)

As for the pic you show, there is no reason to assume that is a plant oil or that it is unwanted. It could be pure DMT. Pure DMT has been shown to be polymorphic, and one of the forms is a yellow oil. My own tests corroborate with that, as yellow oily DMT has shown itself with gc/lc-ms to be essentially pure DMT.


 
Perhaps it helps to clear up the nomenclature a bit.

Saphdmt is using the word "oil" in the sense of macroscopic physical appearance. But when talking about chemical properties, "oil" has a couple of different meanings. It could be:

- mineral oil: This is a mixture of hydrocarbons, straight chained, branched, saturated or unsaturated, aliphatic or aromatic. Diesel oil, gasoline and naphtha are refined forms of mineral oil. Mineral oil is very non-polar.

- vegetable (or animal) oil: These are so-called triglycerides, three units of fatty acid esterified with one unit of glycerol. Different vegetable oils may carry different fatty acids, depending on plant source. Animal fats are also triglycerides, eg. a major constituent of butter is the glycerol tri-ester of butyric acid. By action of alkalis, esters may be hydrolized into free glycerol and alkali salts of fatty acids, the latter commonly knows as soaps. Bio-diesel is the result of transesterification of glycerol tri-esters into methyl esters. The higher volatility of mono-esters makes them more useful for combustion. Esters are mostly non-polar, but still somewhat polar, due to the ester group. As the size of the fatty acid and the alcohol increases, the non-polarity increases.

- plant waxes: these are mostly esters of long chain fatty acids and long chain alcohols, but waxes may also contain some long chain alkanes.

And finally on the nexus "oil" may also indicate:

- any non-crystalline goo that is the resulting product of an extraction.

There, you see, it has very little to do with acids and bases, in terms of pH. It does have a lot to do with polarity. The reason why dmt extractions involve acids and bases is that alkaloids such as dmt change polarity under the influence of acids and bases.

There could be a few explanations for your end product having "oily" characteristics:

- plant fats and even waxes are, although mostly non-polar, still a little polar and will dissolve a little in a polar watery extract, especially so if there is a lot of semisoluble plant matter in the solution to help carry them in the polar watery solution. Even the acetic acid can serve as a cosolvent. Perhaps even the dmt is a cosolvent (that's just a guess). If you want to eliminate the presence of non-polars from the watery extract before basifying, extract it while stil acidic with fresh non-polar solvent. This is called a defatting step.

- if your plant material contains other alkaloids that are also extracted and co-precipitate with the dmt, then that can disturb the crystallization of the dmt. Instead of nice shards, you'll get something oily, that only slowly crystallizes, sometimes taking days or weeks. Some plant sources contain a lot of nmt, some plant sources contain a lot of dmt n-oxide.

- Dmt is polymorphic, meaning it can have multiple crystal structures, not all are clear white.

- Your naphtha has impurities. Alsways test evaporate your naphtha before using it in an extraction.
 
Exactly like the guys before me said. But let me be more exact.
Oils are not just fats or the fatty acids also called lipids.
Wikipedia said:
An oil is any neutral, nonpolar chemical substance that is a viscous liquid at ambient temperatures and is both hydrophobic (immiscible with water, literally "water fearing") and lipophilic (miscible with other oils, literally "fat loving"). Oils have a high carbon and hydrogen content and are usually flammable and surface active.

The general definition of oil includes classes of chemical compounds that may be otherwise unrelated in structure, properties, and uses. Oils may be animal, vegetable, or petrochemical in origin, and may be volatile or non-volatile.[1] They are used for food (e.g., olive oil), fuel (e.g., heating oil), medical purposes (e.g., mineral oil), lubrication (e.g. motor oil), and the manufacture of many types of paints, plastics, and other materials. Specially prepared oils are used in some religious ceremonies and rituals as purifying agents.

And also
Organic oils are produced in remarkable diversity by plants, animals, and other organisms through natural metabolic processes. Lipid is the scientific term for the fatty acids, steroids and similar chemicals often found in the oils produced by living things, while oil refers to an overall mixture of chemicals. Organic oils may also contain chemicals other than lipids, including proteins, waxes (class of compounds with oil-like properties that are solid at common temperatures) and alkaloids.

Especially alkaloids often dont get put in solution by Lye. Dmt for example does.
But stuff like essential oils are mostly all unsoluble in water. Limonene or Myrcene are such examples. Even a base cant attack those compounds to salt them and put em into solution.
"Essential Oils"
Just try it and add limonene to your extraction. It will stick to the dmt but evaporate afterwards.
 
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