Author Topic: Trimethylamine - Easy synthesis from Choline?  (Read 122 times)

Vesp

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Trimethylamine - Easy synthesis from Choline?
« on: September 16, 2010, 06:23:25 PM »
Choline comes in various forms from various places for health reasons, etc.

If you look at its structure http://en.wikipedia.org/wiki/Choline

Quote
Choline hydroxide is one of the class of phase transfer catalysts which are used to carry the hydroxide  ion into organic systems, and because of this it is considered a strong base. It is the least costly phase transfer catalyst, and is used as a cheap method of stripping photoresists in circuit boards. Choline hydroxide is not completely stable and it slowly breaks down into trimethylamine.[citation needed]

I am thinking the addition of a strong base to the hydroxide will release trimethylamine - I did just that in a test tube, but only got a very slight smell of something fishy, and it looks as though also a gas of generated that could be ignited - however, I used a lighter to test this and possibly it could have been the butane giving a false positive of a flammable gas.

Anyone have any input on this? Not to sure if trimethylamine is of any use, but it has some properties that might make it useful.

Thought I would at least mention this...
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jon

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #1 on: September 16, 2010, 07:03:41 PM »
i know any betaine will pyrollitically distill into trimethylamine

Vesp

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #2 on: September 16, 2010, 07:13:25 PM »
http://en.wikipedia.org/wiki/Trimethylglycine
Nice! It is essentially the same, however the instead of being an alcohol, it is an acid.
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jon

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #3 on: September 16, 2010, 08:43:35 PM »
i thought it was pretty nifty too for the triethylamine impaired

Vesp

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #4 on: September 17, 2010, 12:42:11 AM »
What is the increased usefulness in triethylamine vs trimethylamine? Just boiling point?
What is its primary use?
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poisoninthestain

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #5 on: September 17, 2010, 08:38:23 AM »
Organic Syntheses, Coll. Vol. 1, p.531 (1941); Vol. 1, p.79 (1921).

ammonium chloride + paraformaldehyde, mix, 2-3 neck flask ideal, reflux until CO2 evolution ceases, charge addition funnel with NaOH, and drip base into rxn flask while setting up a water trap to absorb the trimethylamine in con. HCl.

Vesp

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #6 on: September 18, 2010, 03:39:11 AM »
I assume metaldehyde would produce the triethylamine variant?
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no1uno

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #7 on: September 21, 2010, 03:03:54 AM »
The betaine route looks nicer, there's even a paper on it amongst the refs.
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atara

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #8 on: September 26, 2010, 07:08:56 PM »
What you're doing to choline is basically a hofmann elimination. The resulting ethenol tautomerizes to acetaldehyde, generating two useful things from choline. So, the catalyst you're looking for is silver oxide.
« Last Edit: September 26, 2010, 07:12:29 PM by atara »

Vesp

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #9 on: September 26, 2010, 09:17:49 PM »
Awesome! Would a similar oxide work as well, such as copper oxide?

 this shows some info on acetaldehyde being produced -- Electrochemical decomposition of choline chloride based
ionic liquid analogues


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atara

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Re: Trimethylamine - Easy synthesis from Choline?
« Reply #10 on: September 26, 2010, 11:45:23 PM »
Awesome! Would a similar oxide work as well, such as copper oxide?

No idea. Silver chemistry is weird and awesome (see also Hunsdiecker reaction and adrenochrome). Silver (I) is a much stronger oxidising agent than copper (I), though, so you're probably going to want the real deal.

The good news is that silver nitrate is cheap, and it reacts with aqueous NaOH to form AgO.

EDIT: One obvious use for trimethylamine: its N-oxide reacts with acetic anhydride in a Polonovski reaction to form dimethylacetamide and formaldehyde. Dimethylacetamide is pretty awesome, I'd say, and choline is as OTC as table salt.
« Last Edit: September 27, 2010, 04:50:07 AM by atara »