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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: sriram on July 29, 2020, 11:12:34 AM

Title: DECARBOXYLATION OF EDTA TO TMEDA
Post by: sriram on July 29, 2020, 11:12:34 AM

Hey there,
I want to make TMEDA to test  some of its interesting properties,till now i have only found decarboxylation the only way to get TMEDA from tetra-sodium salt of EDTA.Please suggest the feasible way to get TMEDA with high yield by decarboxylation of tetra-sodium salt of EDTA.If not suggest any other way which amateurs can get their hands on.

Title: Re: DECARBOXYLATION OF EDTA TO TMEDA
Post by: rolnor on July 29, 2020, 11:31:55 AM

You can buy this I think, could be problem with the shipping because its a liquid though; http://www.chemnet.com/ChinaSuppliers/14012/TMEDA--414138.html

Title: Re: DECARBOXYLATION OF EDTA TO TMEDA
Post by: sriram on July 29, 2020, 11:42:14 AM

Yes sir it is and it's little expensive too.

Title: Re: DECARBOXYLATION OF EDTA TO TMEDA
Post by: phth on July 29, 2020, 02:04:47 PM

Quote from: sriram on July 29, 2020, 11:42:14 AM

Yes sir it is and it's little expensive too.

500 mL for about $100 is dirt cheap.

Title: Re: DECARBOXYLATION OF EDTA TO TMEDA
Post by: sriram on July 30, 2020, 12:13:21 AM

EDTA is available quite more cheap and in good amount.i would like to get my hands on its.

Title: Re: DECARBOXYLATION OF EDTA TO TMEDA
Post by: Enthalpy on July 30, 2020, 05:05:04 PM

Permethylated ethylamines are normally obtained from the parent ethylamine, in a mass-production. I've forgotten the details, but it resembles: mix with methanol and formaldehyde, stir and heat, done. The permethylated ethylamines are industrial compounds. In drum amounts they should cost like 3usd/kg.

So wouldn't it be easier to find the permethylated thing ready to buy? Or if not available, to methylate in your lab the ethyleneamine?

Title: Re: DECARBOXYLATION OF EDTA TO TMEDA
Post by: kriggy on July 31, 2020, 05:32:47 AM

you are missing formic acid as a hydride source to reduce the intermediate imine.

Anyway, he seems to be home chemist so he might have difficulties accessing the required reagents. Nevertheless, I feel like the decarboxylation is going to be quite difficult step. Its definitelly easier to buy TMEDA

Title: Re: DECARBOXYLATION OF EDTA TO TMEDA
Post by: sriram on July 31, 2020, 07:44:47 AM

what if ethylenediamine undergoes  Eschweiler–Clarke reaction.it might work.

Title: Re: DECARBOXYLATION OF EDTA TO TMEDA
Post by: Enthalpy on July 31, 2020, 03:25:00 PM

Quote from: kriggy on July 31, 2020, 05:32:47 AM

You are missing formic acid as a hydride source to reduce the intermediate imine.

Thanks, I didn't even know the laboratory reaction with formaldehyde and formic acid
https://en.wikipedia.org/wiki/Eschweiler%E2%80%93Clarke_reaction

For the industrial compounds I suggested to buy (which may indeed be difficult for individuals), methanol is apparently preferred, with or without hydrogen
https://en.wikipedia.org/wiki/Amine_alkylation
https://data.epo.org/publication-server/rest/v1.0/publication-dates/19900627/patents/EP0375333NWA2/document.html
Obviously, I have no opinion on the topic. I understand that 30 bar or 300 bar aren't desired in a lab, less so with hydrogen.