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Re-Carboxylating BHO


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#1 HarvardHempHarvest

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Posted 11 December 2016 - 05:55 PM

A random idea came to mind while smoking a bowl and watching a peregrine falcon eating a chickadee in my yard. After time and temperature has turned my shatter into a sticky mess of oil, can the BHO be carboxylated back to THC-A, CBD-A, etc?

My plan is to store the decarbed oil with dry-ice in a pressurized chamber, in the hope that the CO2 will re-attach to the cannabinoids in the same way fruit and soda becomes carbonated. Successfully carboxylated shatter should be immediately discernable from some plain old fizzy carbonated oil.

Anyone with enough chemistry knowledge for some constructive criticism or want throw a dollar on an outcome, your input is welcome.
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#2 Damar

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Posted 11 December 2016 - 08:22 PM

So I'm not a chemistry expert, but I would venture to say you are missing some sort of positive electron stabilization mechanism (positive metal ion?) while the molecule rearranges allowing for the grab of the CO2 from the surroundings. Furthermore, what is done to keep the positive charge in the right place while the reaction takes place? Just shatter + CO2 in a pressurized chamber doesn't seem like it's generating the necessary energy for the reaction to take place.

THC Acid decarboxylation already takes a certain amount of energy to occur (usually heat, in our smoking/edible making case), with certain catalysts lowering that energy (seems like some research has been down with formic acid?)... I dunno, I was always under the impression that joining molecules together takes more energy than breaking them apart, so without some sort of enzyme grabbing the individual molecules and bringing them into the right positioning I would be surprised if a simple pressurization with an excess of CO2 would accomplish this carboxylation reaction.

#3 HarvardHempHarvest

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Posted 11 December 2016 - 10:26 PM

Yeah, that makes sense. I haven't yet looked into the process for carboxylating anything, but it does seem overly simple to assume that just dissolving CO2 into the dabs would miraculously reverse the decarboxylation reaction.

I figure worst case scenario it'll just be a waste of time and effort though, there's not much monetary risk involved.
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#4 Damar

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Posted 12 December 2016 - 02:48 AM

View PostDamar, on 11 December 2016 - 08:22 PM, said:

I dunno, I was always under the impression that joining molecules together takes more energy than breaking them apart

I need to correct myself here - both situations are possible (how I forgot this boggles my mind... oh yeah, we are a stoner forum ;) )

Exothermic reactions, the products of the reactants have a lower bond energy, and energy is given off, usually in the form of heat (think instant handwarmer packs)

Endothermic reactions, the products of the reactants have a higher bond energy, and need energy/take heat to complete (think instant cold packs)

Either way, I have a feeling that in this case, there is a higher activation energy hump that needs to be met, regardless of the final bond energy of the carboxylated molecule. And this is just my feeling. Organic chemistry has the tendency to not care about your feelings, or what your theory might be on how the reaction mechanism takes place. There is one way it's happening, based on local electro-negativities, whether you like it or not. I love chemistry, it's just really fucking hard when you have to cram a year's worth into a 12-week summer session (and do a lab which takes up most of your free time, leaving not enough time for study nor practice).

/rant HEY! but that was in 2011 :D a little self-inflicted torture.

#5 gardenartus

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Posted 12 December 2016 - 04:12 AM

If you can't find an answer by asking that, maybe reverse and search for, where does the acid go to, drop offs and not retainable? I don't believe this is possible, but I am going to search now just to see what does occur with the a or acid when we decarb, Good food for thought, yea gotta go to the kitchen with it lol

Considering how long it takes, and/or high heat, to actually drop the acid, I would think it would be a permanent state. Does any kind of a fusion occur when it drops and it is being heated, and some how sealing the end? Would it be more possible if this were a naturally occurring decarb instead of heat induced? Just a few things you might search out.
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#6 MostlyMe

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Posted 12 December 2016 - 01:09 PM

I am an organic chemist, and I can tell you there's no way in hell you can recarboxylate the way you propose. Only in the presence of a catalyst can you do that, and even then you would probably get by-products in which the CO2 has reattached itself in the wrong place. (In case you are interested, typically a Lewis acid like AlCl3 is used for carboxylation, which forms a complex with CO2 that subsequently reacts with the aromatic ring by electrophilic substition).

The reason DEcarboxylation takes a bit of heat, is that the reaction has a high activation energy. In itself, the reaction is energetically favorable. Reactions that release a gas typically are.
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#7 gardenartus

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Posted 13 December 2016 - 06:24 AM

Cool! A chemist. :) You should let me pick your brain on how to make a nose spray with cannabis oil in it MostlyMe. :)
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#8 Damar

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Posted 13 December 2016 - 06:41 AM

View Postgardenartus, on 13 December 2016 - 06:24 AM, said:

Cool! A chemist. :) You should let me pick your brain on how to make a nose spray with cannabis oil in it MostlyMe. :)

When I read that my first thought was about the process of removing part of the brain through the nose the way the ancient Egyptians did it prior to embalming a body. :P

Wikipedia tells me this is called excerebration - hopefully the nasal spray does not do that... well, maybe only figuratively. ;)

#9 gardenartus

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Posted 13 December 2016 - 07:23 AM

Hehehe funny, Hey dude, just let me pick your nose would ya lol
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#10 Misterdirt

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Posted 13 December 2016 - 07:38 AM

Like my grandma always said:

You can pick your friends.
You can pick your nose.
But you can't pick your friend's nose.

I don't know if that applies here or not. No one knew what that crazy old woman was talking about.
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#11 MostlyMe

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Posted 13 December 2016 - 12:47 PM

View Postgardenartus, on 13 December 2016 - 06:24 AM, said:

Cool! A chemist. :) You should let me pick your brain on how to make a nose spray with cannabis oil in it MostlyMe. :)

Happy to have my brain picked, but I wouldn't spray any other solvent than water in my nose, so there's the problem right there. The only thing that I can think of is making some sort of very finely dispersed emulsion. That should be possible, but you'd need a surfactant that both forms THC-containing microdrops ánd is safe to ingest. Many surfactants are used in processed foods, so I suppose one of those would be alright. But which one, ratios and using what protocol to create the emulsion is not trivial.
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#12 gardenartus

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Posted 13 December 2016 - 03:25 PM

Yep that is exactly what I figured too, if you could get a finest enough mist it would work, I think I would need special lab equipment for that. I don't know what I could mix with a saline solution that would allow the cannabis oil to dissolve and disperse, it is quite heavy.
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#13 MostlyMe

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Posted 14 December 2016 - 12:07 PM

View Postgardenartus, on 13 December 2016 - 03:25 PM, said:

Yep that is exactly what I figured too, if you could get a finest enough mist it would work, I think I would need special lab equipment for that. I don't know what I could mix with a saline solution that would allow the cannabis oil to dissolve and disperse, it is quite heavy.

You would have to dissolve the oil it in a solvent that mixes with water, ethanol would probably be best/safest. I'd imagine you would have to add the solution dropwise to vigorously stirred, heated water with the surfactant in it. The ethanol would evaporate eventually, after which you can cool and hopefully have your emulsion. It will certainly take a lot of tries to get it right (so many variables), but the nice thing is if it fails, your oil should be floating on top of the water, so is not lost :)
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#14 gardenartus

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Posted 15 December 2016 - 10:18 AM

I tried a few different things, sonic cleaner as well, but the oil is so heavy it forms back into itself. I tried it in a diffuser that creates fine mist, other essential oils dissipate, but not this, it just sank lol. There is a fat, can not think of it, that someone here gave me a link too, that is safe for nasal cavities, it is hard to locate, lab grade and expensive I believe. For it to work though special lab equipment is needed.
The Devil Whispered in my ear "You're Not Strong Enough To Withstand The Storm" Today I Whispered In the Devil's Ear " I AM THE STORM"

Darkness can not hang with the light, The guilt becomes too much, too large a burden to bear, and soon they slink back into the night. Their actions they no longer can ignore, when the lightness shows their true intent. Choose to be the light.

#15 HarvardHempHarvest

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Posted 09 January 2017 - 04:49 PM

I did a little research into the nasal spray subject and came across the claim that clinical trials have proven vegetable oils don't cause the lipid pneumonia that animal fat inhalation causes.
While I haven't seen documentation to support that claim yet, I've found a few nasal spray products already on the market with sesame oil, orange oil, lemon oil, and ethanol. Look up GeloSitin and one of the first results should be a PDF that might interest you.
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#16 MiNdLesS

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Posted 10 January 2017 - 04:31 PM

I was needed to use orange oil after a surgery for my nose. I liked that stuff!

Greetz
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#17 gardenartus

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Posted 11 January 2017 - 10:03 AM

Cool so there are actual safe oils to use that are fairly common, I need to get back to researching.
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#18 Elro

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Posted 14 January 2017 - 07:02 AM

View PostMisterdirt, on 13 December 2016 - 07:38 AM, said:

Like my grandma always said:

You can pick your friends.
You can pick your nose.
But you can't pick your friend's nose.

I don't know if that applies here or not. No one knew what that crazy old woman was talking about.
LOL I believe a little levity from Monty Python is in order here!!!!
https://youtu.be/M0gzQS4w1sc
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