How cold
can you tell me what “pTSA” beads are?
Sorry for the confusion.
strong acid cation beads with “sulfonic acid” as their functional group.
They just behaved the same like regular pTSA in terms of time, temperature and results. That’s why I said pTSA beads.
yes as primary catalyst
you understand that if you used sulfuric acid or pTSA as catalyst
you could scavange it up with a basic anion exhanger.
The color of your crude shouldn’t effect the color of your finished distillate
In fact these sulfonic polymers are less d8 specific than PTSA (above 90% d8), even a bit less than CSA. They favor less d8 (max 75%) to the profit of iso-d8 (above 15%).
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Lol what
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The color of your reactionary crude should not effect the color of the finished distillate
My guess is the pTSA is silane functionalized to mesoporous silica. MCM-41 and SBA-15 porous glasses can be surface functionalized with just about anything.
This is really the direction I want to go with the industry, but my company has a ways to go before we can get there.
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Do any of the solid state catalysts show preference for d8/d9 yield depending on polymer back bone…?
I would certainly like to find out. I did a lot of solid state surface chemistry work in grad school. Silica is an amazing material.
It is possible that tethering your catalyst to a solid support could change the product preference. It could give more control of the extent of the reaction. But the fact of the matter is, the business end of pTSA is the sulfonic acid -that alone likely drives the reaction to favor 8 over 9. But there could be some sterics and rotational aspects in place that could mean a tethered catalyst results in more preference for 9 than 8. pTSA, if covalently bound to glass, could change the pKa of the acid.
But it would be easy to graft different catalysts (weak acids) to silica and try those too.
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I worked a bit with Controlled Pore Glass as support for oligonucleotide synthesis. That might be a sturdier solid phase than the MCM-41 and SBA-15 porous glasses. I also wonder what kind of loading can be achieved with either of these supports.
The typical strong cation exchange resin is essentially support bound arylsulfonic acids and as far as it being compatible with desired solvent and temperature combination, should work just fine as a cyclization catalyst.
I like the idea of being able to use an anion exchange resin to simplify workup as @moronnabis mentioned, capturing the catalyst used in a regular solution type cyclization. You’d still have maximum flexibility as to what solution synthesis has to offer while possibly completely avoiding an aqueous workup. And in theory, the scavenged catalyst ought to be reclaimable. And if that’s not totally straightforward, at least regeneration of the anion exchange resin should be easy.
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Yes, I am aware of this.
I guess there was a general misunderstanding (also from my side).
Ion exchange resin beads is a topic, that has not been talked about much.
Cation exchange resin beads can be used to isomerize CBD and anion exchange resin beads can be a great tool for work up.
What I was initially talking about, is to mix anion and cation exchange beads, while performing the isomerization itself, because there are rumors that this combo would lead to a much higher D9 amount of +90%.
I was not able to reproduce those numbers and I am not sure how valid this information about people using anion AND cation beads with 90% D9 yield really is. Last year when everything started, people also claimed they get above 90% D9 with pTSA only on a production scale…
I have a theory, what this “mix of beads” could be, but I doubt it is a mix of anion and cation ion exchange beads.
The possibility to completely skip aqueous workup, makes it very interesting and is worth it for me to dive deeper into the topic of ion exchange beads / support bound reagents. I still don’t know enough and I’m only just starting in this topic.
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trying to think about what might be going on with the anionic
“ion exchanger” as an additive…but the end point…if it “WORKS”
with and not without for increased yield of d9…who cares about why.
Can we see the numbers from someone?
Bhogi, Thank you for the explanation…
“This is why I said ion exchange is the future”…
K of K : one might more clearly state that aryl-sulfonic-bonded and crosslinked styrene resins have the potential for catalyzing intramolecular isomerizations of specific cannabinoids.
Moreover, highly unlikely anything to do with “ion exchange”.
In which case you might opine: “ion exhange resins” have a
future as catalysts,
capisce?
You are a longways from cation exchange with a CBD molecule.
It is not all bad…I find your Membrane systems “AAA”…
fine looking …wheels on…plugs and chords all straightened out…
the new pumps…AAA
I am a little confused as to what people are calling “ion exchange” in this application. I don’t believe solid state catalysis and ion exchange are the same thing, though an ion exchange resin could be catalytic for some applications. My understanding could be limited though.
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This goas as you wrote it.
People exploit catalytic properties of polymers which are normally intended for ion exchange.
These polymers can come in the form of resins or small beads. I believe people are rather using beads than resins.
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It just happens that the most common strong cation exchange resins displays arylsulfonic acids and can be used both for ion exchange and as an acidic catalyst, provided the resin is in its H+ form.
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I think it’s the same thing. I think the process of cross-linking historically was considered as providing a resinous material.
For it to be of practical utility, the resin is shaped into beads.
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yeah, bro. give us the sauce…
because I’m pretty sure the only liver damage was related to also taking two very rare drugs, and it was the metabolite of that drug interacting with the CBD to cause the damage.
From Dosage, Efficacy and Safety of Cannabidiol Administration in Adults: A Systematic Review of Human Trials - PMC high doses in these clinical trials seems common. The linked one was 1000mg/day for 6 weeks for Schizophrenia. They monitored liver enzymes and “There were no significant changes in prolactin levels, Simpson-Angus Scale ratings, weight, waist circumference, liver function tests,…”
https://ajp.psychiatryonline.org/doi/full/10.1176/appi.ajp.2017.17030325
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