Concentrating vinegar (acetetic acid)

[Grower]

Can one concentrate vinegar (acetetic acid) so one gets glacial acetetic acid (max concentration, without water)?
Does for example a distillation (standard or vacuum) work to achieve this?
Max concentration in ordinary stores are 24% vinegar where i live.

Is it possible to distill all kind of acids in this way to get a more clean acid?

Grower

 

[benzyme]

24% vinegar? what's the other 56%?

vinegar is dilute acetic acid, generally 5-9% acetic acid.
it is a volatile acid, so reducing it down probably won't concentrate it much, if at all.
acetic acid forms an azeotrope with water.

for all practical purposes, there's no real need for glacial acetic acid in extraction.


acids have water (they're not acids without it). more water doesn't make them "dirty", it just makes them dilute.

 

[Auxin]

Acetic acid does not form an azeotrope with water.
As per the 60th edition of the CRC any mixture of the two is zeotropic, ie. they can be separated by distillation. Get thee a vigreux or water jacketed column and boil away! (I like vigreux distillation columns because they just look psychedelic)
The boiling point of glacial acetic acid is 117.9° C or 17° @ 10 mmHg

for all practical purposes, there's no real need for glacial acetic acid in extraction.

Since when are psychonautic dreamers constrained by the orthodoxy of the current archetype of practicality?
For instance, anhydrous glacial acetic acid is soluble in anhydrous toluene, but few alkaloid acetates are... I could see a practical application.

 

[Grower]

Well, the bottle says 24% acetic acid.
I was interested if there was a way of making it less diluted as in stronger %.
There is many reactions and uses of acetic acid and many call for a higher % than ordinary vinegar.

I don't really understand the "24% vinegar? what's the other 56%?"
Maybe you meant 76%?
I guess its water.

With for example sulfuric acid, one can boil of water making it less diluted (stronger %), but you mean it cant be done with acetic acid?
Has it about the same boiling point as water or is it because it forms an azeotope with water that this don't work?
And drying it with some water absorbing chemical don't work either?
There must be a way of getting it more concentrated.
How about vacuum distillation?

 

[benzyme]

molecular sieves.

sulfuric acid isn't volatile, but it still forms an azeotrope. you can get it as high as
96% by drying it.

acetic acid and hydrochloric acid aren't like that. distilling (vacuum or simple) them won't get you up to those percentages (especially HCl, 37% is about as conc. as you can get).

why would you need glacial acetic acid?

 

[Grower]

I have no specific reaction or use planned but i have found out it is used a lot.
The properties of anhydrous acetic acid and water diluted acetic acid is very different.

So one cant concentrate it by trying to remove some of the water.
Are many other acids who also is volatile like these 2?

Can one convert a volatile acid to something else by a reversible reaction, separate from the water and reverse the reaction to get a higher concentration?
Just a thought.
It could always be good to know if concentrating volatile acids is possible or if the only way is to get a higher concentration from the start.

 

[benzyme]

The properties of anhydrous acetic acid and water diluted acetic acid is very different.

I know.

So one cant concentrate it by trying to remove some of the water.

I didn't say that. Molecular seives are used all the time to concentrate solutions.

Can one convert a volatile acid to something else by a reversible reaction, separate from the water and reverse the reaction to get a higher concentration?

NaHSO4 + NaC2H3O2 <--> Na2SO4 + C2H4O2
distill.

you need at least some water for an acid to behave like an acid, that is, proton dissociation.


if you know of any evidence or realized advantages for using GAA in an alkaloid extraction, please mention them. I can't think of any.

an ideal process calls for total cell lysis (this can be done mechanically, or thermolytically), dilute acid added to pH 5.2 for DMT to be fully protonated (9% acetic acid has a pH of 2.4).

 

[dooby]

an ideal process calls for total cell lysis (this can be done mechanically, or thermolytically), dilute acid added to pH 5.2 for DMT to be fully protonated (9% acetic acid has a pH of 2.4).

1. "Mechanically": would it help to make something that could hold dry bark and that could be put in a benchvise in order to "squeeze" the hell out of that bark?

2. If pH 5.2 is sufficient for DMT to be fully protonated, why do all teks advise pH 3-4? Is this to aid cell lysis? I read somewhere why pH shouldn't be lower than 3, but why not 5.2 rather than 3 or 4?

3. If sufficient cell lysis would be reached before or at the beginning at the basic stage of an extraction, wouldn't one expect all pulls to be equally saturated? As it appears that later pulls are less saturated and as some people allow their later pulls to sit for hours or even days, are those people waiting for the base to complete cell lysis?
Is there a reason why acid soaks and freeze/thaw strategy can't be done until 100% cell lysis is achieved, thus allowing for much faster, and more saturated, pulls?

I would like to understand why successive pulls tend to become less saturated, this has either to do with not all spice being "free" to migrate into the NPS at the time of pulling (due to incomplete cell lysis?) or with the fact that the basic solution itself becomes increasingly less saturated (in which case I would think "rolling" the later pulls more times than initial pulls might help to increase saturation of later pulls?)

And on a less serious sidenote, could cell lysis be achieved with electric shocks? (without destroying the spice)

 

[benzyme]

an ideal process calls for total cell lysis (this can be done mechanically, or thermolytically), dilute acid added to pH 5.2 for DMT to be fully protonated (9% acetic acid has a pH of 2.4).

1. "Mechanically": would it help to make something that could hold dry bark and that could be put in a benchvise in order to "squeeze" the hell out of that bark?

2. If pH 5.2 is sufficient for DMT to be fully protonated, why do all teks advise pH 3-4? Is this to aid cell lysis? I read somewhere why pH shouldn't be lower than 3, but why not 5.2 rather than 3 or 4?

3. If sufficient cell lysis would be reached before or at the beginning at the basic stage of an extraction, wouldn't one expect all pulls to be equally saturated? As it appears that later pulls are less saturated and as some people allow their later pulls to sit for hours or even days, are those people waiting for the base to complete cell lysis?
Is there a reason why acid soaks and freeze/thaw strategy can't be done until 100% cell lysis is achieved, thus allowing for much faster, and more saturated, pulls?

I would like to understand why successive pulls tend to become less saturated, this has either to do with not all spice being "free" to migrate into the NPS at the time of pulling (due to incomplete cell lysis?) or with the fact that the basic solution itself becomes increasingly less saturated (in which case I would think "rolling" the later pulls more times than initial pulls might help to increase saturation of later pulls?)

And on a less serious sidenote, could cell lysis be achieved with electric shocks? (without destroying the spice)

good questions.

1. this is called cold press extraction, and would work well with the grasses.
A pressure cooker is a good alternative, particularly when the material has been soaking in a dilute acid. Add the dilute acidic mixture with the raw material to some lightly capped jars (about 2/3 filled), and PC for about 40 mins, repeat if necessary.

2. The teks are rough estimations, and empirical by nature. the authors experiment using these pH's. The number I cite is calculated from ACD Labs/ChemAxon's Chem Sketch, you can also find the pKa values here.
I picked 5.2, because approx. 99.98% of the DMT will be salted.

3. People use excess acid or base to hydrolyze rigid plant cell walls, as the alkaloids
are contained in the cytoplasm (as opposed to trichomes in cannabis, where the actives are outside the cell walls). With mechanical means, you can save the extra acid/base, and let brute force thermodynamics work for you. Just don't burn the plant material, this will cause actives to decompose or boil off.


Successive pulls become less saturated, because of what the previous answer suggest: once you've lysed the cells walls, and the alkaloids are in solution, subsequent pulls will yield less. Most of the alks are pulled by the second pull.

electric shocks...there's an interesting approach, worth experimenting with. I know in biochemistry, electroporation is used to temporarily disrupt cell walls to introduce plasmids (DNA), so I'd imagine it could work if done extensively.

 

[benzyme]

btw..

my favorite sites for any sort of chem are

Chemicalize - Instant Cheminformatics Solutions

Calculate properties, search chemical data, and draw molecules online.

chemicalize.org

Wolfram|Alpha: Making the world’s knowledge computable

Wolfram|Alpha brings expert-level knowledge and capabilities to the broadest possible range of people—spanning all professions and education levels.

wolframalpha.com

they take out a lot of the guesswork, and calculations are conveniently done for you.
you can plan extractions using these sites.

ChemSpider | Search and share chemistry is another good one, it lists calculations from ACD Labs (chemicalize.org)

 

[dooby]

Thank you benz for your posts...

 

[benzyme]

always welcome.

 

[Grower]

Yes, thanks for all great info.

Grower