fatroucha
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Choline chloride from choline hydroxide?
Can I obtain choline chloride just by reaction choline hydroxide with hydrochloric acid?
(Edited title for clarity)
[Edited on 10-24-2017 by zts16]
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Nicodem
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Thread Moved
23-10-2017 at 09:00 |
aga
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Try it on a small, safe scale and see what happens, although i have no idea how an amateur would test the products to positively identify what the
results would be.
A suggestion would be to find the Hof values of the reactants and products to see if choline chloride formation is thermodynamically favourable,
although sources such as http://webbook.nist.gov have little data about choline chloride/hydroxide.
Wiki says choline hydroxide degrades over time into trimethylamine, so if your batch smells intensely fishy ...
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DraconicAcid
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You should be able to, but I would advise against mixing the concentrated substances. I didn't know choline hydroxide was stable.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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fatroucha
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In our laboratory, we dispose of Choline hydroxide solution 45 wt. % in methanol, I thought just by neutralizing it with the adequate amount of
hydrochloric acid I would obtain choline chloride. However, for some reasons, I couldn't obtain the desired product. I suspect that a side reaction
may have occurred but I'm not sure.
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LearnedAmateur
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Have you tested the product with dilute aqueous silver nitrate? That should show you whether the neutralisation has occurred or not through
precipitation of AgCl. Also, have you considered what side reactions could take place? There doesn't seem to be much that can happen to choline, being
a small molecule, and I doubt a simple ~20C acidic environment will be able to affect the cation or alcohol group much.
In chemistry, sometimes the solution is the problem.
It’s been a while, but I’m not dead! Updated 7/1/2020. Shout out to Aga, we got along well.
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fatroucha
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I suppose the hydrochloric acid has reacted with trimethylamine producing triethylamine hydrochloride, I think choline hydroxide decomposed to
trimethylamine and ethylene.
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aga
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Quote: Originally posted by fatroucha  | | I suppose the hydrochloric acid has reacted with trimethylamine producing triethylamine hydrochloride, I think choline hydroxide decomposed to
trimethylamine and ethylene. |
Well, bubbles would be a clue as those last two are gas at RT.
What was the process you tried ? Doesn't look like anything could just precipitate.
Choline chloride is very soluble/hygroscopic, so evaporation/drying are quite hard, although not so difficult to get dry as say, CaCl2.
Hardest part is drying ChCl without burning it in my limited experience.
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fatroucha
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I have neutralized choline hydroxide with HCl while keeping the solution cool then I have removed the water/methanol. The ending product was a very
viscous liquid with the characteristic smell of amine.
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