Ok I need some help in understanding the chemistry
Sadly @davidb @mitokid are not around to give a chemist insite
Have a look at this
This is one of the examples in this paper
How the hell is it possible that the A is still present after prolonged heating ???
Are the reagents used decarboxilation stoppers huh ??
Any of the chemist willing to give an explanation as to how this would work on a molecular level ?
" 1,4-Benzoquinone serves as a dehrdrogenation reagent." Also claims to be an oxidizer from the sources I’ve read.
Best guess is it can at least keep the THC a bit more stable.
that’s with my bit of Chem knowledge and looking over materials. (Ain’t much but, there it is, whether it’s a turd or not)
My best guess is it keeps at least a certain amount from
Yep that’s what it looks like
And it would be quiet amazing if it does
Honestly we know some compounds speed up the decarboxilation process but having compounds that slow the decarboxilation down
Would be an interesting find
Hope more folks chime in
I swear I should be in research or something…
Having a serious “wtf am I doing with myself moment over here…”
I’m not an organic chemist, so idk about this. I know pressure doesn’t affect decarb, but does hydrogen bonding or other intramolecular forces?
That’s what escapes me there, what specifically is keeping it?
It dehydrogenated, and oxidized however, which is strange, this is a mental gymnastic I need an adult for.
(Politely raises hand with @Roguelab hoping for adult-ier adults)
My subconscious is screaming at me about basicity and stability of the leaving group but I have slain so much of the orgo brain cells.
I don’t usually see rapid decarb until a solution temp of well over 100C. I’m not sure how people I’ve seen who decarb at 70C are getting it done efficiently.
It’s possible in this patent they are doing something more careful than labs normally do. Something like an oil bath set to 100C which wouldn’t necessarily raise the internal temp to that point for many of the hours.
It’s also a dilute solution which could contribute
“Substantial amount” needs to be quantified.
I’m interpreting that blurb as saying that the vast majority of the result was CBNA, CBN, and THC with a surprising nonzero amount of unreacted THCA.
Real world reaction chemistry works on equilibrium. It’s not really as simple as A+B=C. The conditions of the reaction will drive the equilibrium more toward one side or the other. It reads like there are more reactions occurring than simply the decarboxylation reaction, all of which will compete with each other and potentially make it more difficult to achieve 100% conversation (which already is fairly difficult to achieve without going to the extremes of reaction conditions).
this is where we really miss Mito….the real chemist!
Mamoris may be best bet right now.
If you look closely at the introduction to example 1 of this patent
You will find a few things to consider:
Blockquote As will be appreciated by those skilled in the art who have benefitted from the present disclosure, aprotic solvent systems may comprise small amounts of protic species, the quantities of which may be influenced by the extent to which drying and/or degassing procedures are employed.> Blockquote
this is the subject of the German Ph.D. Thesis I have pointed out…
Which clearly states this problem(protic in aprotic problem)…and furthermore states how difficult it is to describe the “likes” of salicylic acid in aprotic solvents. So the authors here are saying…”we are not going down that road” and you should know this and you are on your own. (For those who don’t follow…it is rather impossible to describe the solution chemistry of THCA in alkane: .are you dealing with solute interaction with heptane in this case…or contaminating protic complexes interacting with Heptane) and both. Here we are discussing dilute solutions.
I want to throw out the idea that the benzoquinone action is on the heterocyclic ring (the dehydrogenation) and probably has nothing to do with stabilizing the R-COOH from decarbing at 100C for prolonged times. That said (a total guess) , if you look up the vapor pressure of Heptane at 100 C it is about 15 psi. Now the reactions described are in 10ml volume scale. These have to be capped and hold pressure for that time period. So I would first
Cap a solution of THCA in Heptane (suitable container) and run the decarb reaction at 100C 15 psi for 24 hr…just to see what happens. If it doesn’t decarb, it is the pressure . If it totally decarbs…it is the addition of the tetrachloro,-1,4 benzoquinone acting as an inhibitor…
This is all assuming the patent examples are reproducible…
The HPLC basically shows very little THCA decarboxylation.
Also keep in mind…getting the water out of the Heptane is difficult…so you can always assume Heptane is something like 5 mM in H20.(10E20 molecules per liter)
Compare with the mole fraction of THCA in the Heptane…fairly dilute here as AlexSiegel points out. I’m saying don’t rule out some funny H20 quinone complex from the equation…as inhibitor. https://patentimages.storage.googleapis.com/8a/c2/a1/c6fef778f1866c/WO2021035342A1.pdf
This is patent image that shows HPLC fig 1 . As you can see the DAD shows
A considerable amount of THCA. Main product CBNA peak is similar to THCA peak left over.
Throwing benzoquinone into a reaction mixture is just way over my head.
24 hours of thc-a !!
Thc-a decarboxilation faster than Cbd-a
And 24 hours is a long time
As for presssure I doubt that it s the key for we have been doing that for a while now with positive decarboxilation results
As for solvent yes might be of influence
I am Gona do some trails on the matter before
Using a catalyst, it still takes several days at such temps, to decarb a CBD/THC crude. Time rapidly goes down to a few hours, or even few minutes, if the temperature is raised.
@Roguelab do they report reaction extents in their patents ?
Exactly metal oxides are decarboxilation catalysts and quiet handy for that matter
@thermite once gave a peek into a thc remediation option with partial decarboxilation crude and molsieves
So my interest is
If there are catalyst to speed the process are there any compounds that slow it down ?
This is how LNG works. I believe it’s the van der whals force.
Yes I am. Well aware of the difference in CBDA vs THCA decarb rates….but in open tubes…it takes just a bit more than 100C
For THCA to go off…but by that time the solvent has evaporated off…and you have a concentrated liquid THCA/THC dissolving the THCA as the reaction proceeds. But it all depends on what exactly this author is starting with……it would be nice to believe he has THCA (H) form……??? Dissolved in Heptane with 5mM H2O??? This is the recurrent “butane works no theory” problem
Of trying to figure out exactly what one is doing.
So doing the experiment is easier than thinking about it…
You would think it would be totally decarbed…
The patent author says: stirred and heated to 100C for 24hr.
So this can not be done with Heptane in an open container???
I am assuming he means in a stirred parr autoclave reactor??
This description is a 10 ml experiment…so it is a little sketchy what he means….any ideas?
I’m guessing it has to do with the complexation of the Hydrogen circled here…
we decarb with our recirculator set to 95c, the solution is usually around 90-92c (thermoprobe in puddle) and it takes 20-24 hours to decarb 2-10kgs.
This picture makes my (slightly) educated guess make soo much more sense.