methylamine from glycine

[hellman]

This is an old dog, but i wonder if anybody has something to add,.
In Vogels 3rd, glycine is applpied a strong base, which forms methylamine,.
I have not got the ref. but it hides in the back section of vogels, at decarboxylic reaction,.
I remember posting it 3 years ago, but i believe we only had one tester,.
I do believe this should work,.
Any feedback?

[Sunlight]

It has been comented in the Hive, and it works. I made a test mixing CaO, NaOH and glycine and heating it till 220-290 C, glycine decomposes and methylamine is released (and may be ammonia), the decomposition of glycine is not clean, and it is formed at lot of tar and brown organic gases. I put that gas in a HCl solution and evaporated it to get a brownish tar that was wet even weeks ago, and and adding NaOH soolution released methylamine ( methylamine hydrochloride is very hygroscopic).
If someone wants to try it my tipo is to put a refluxer (may be without running water is enough) to catch the organic gasses, so you can get only the methylamine gas. Then you sould determine if it is plain methylamine or there is ammonia as well, becuase the glycine decomposotion is very dirty. An added porblem is how to keep this high temperature.
I made another test decarboxylating glycine with MDP2P trying to isolate the imine and reduce it with NaBH4, decarboxylation worked fine, but rdxn falied. It means that we could use a high boiling point ketone to the decarboxylation. Cyclohexanone in DMF didn't work, and I guess it was due the low boiling point.
I think we can find something useful, but nothing will be discovered if people doesn't play with it.

[hellman]

That's so good to hear!!!
I never heard any working feedback, from when i initially tried this reaction something like 3 years ago,
Thanx Sunlight,
Dirty reaction, hmmm... I wonder what is causing that tar, I would have to see the reaction equation again before making an accurate statement but,I would say that the best way for now would be to decompose it with Cao,  bubble the gas through your hcl, which does give the tar, but then as you said collect this brownish tar,.
Now this browninsh tar contains what, Well maybee we'll look at it another way, it does contain Meam.hcl.
So could we extract it using solubility data, or could we just continue to the next step, I say just continue, my friends,.
Ok, we then apply this goo(Meam.hcl+crap) to naoh which liberates the Meam gas much more readily than before,(that decarbox reaction probab;y charred the Meam Gas).
This gas we then bubble again through Hcl soln./

And this is how we could do it, a continuous large scale methylamine generator,

Sounds good!!!!!!!!!
Of course you might get a little ammonia chloride, but hey that's esy to get rid of, isn;t it(rhetorical)

hellman

Seems like that could be the go,
A kilo of glycine sure would turn into say 500g of Meam.hcl- I just know it,.


IQ is the rate of logic, as Wisdom increases logic, fear & compromise decrease to reveal objectivity

[Sunlight]

Attach a condensor after the heating flask and before collecting  the gas, the organics will be condensed and you could get clean gas.
I've never heard that it doesn't work, UTFSE.

[hellman]

That sounds much better,.

hellman
IQ is the rate of logic, as Wisdom increases logic, fear & compromise decrease to reveal objectivity