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Author Topic: Oxiation of EDTA to Ethylenediamine (Yes, it's true)  (Read 265 times)

no1uno

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Oxiation of EDTA to Ethylenediamine (Yes, it's true)
« on: July 27, 2010, 04:06:24 AM »
There are a number of papers starting to appear on the oxidation of ETDA (ethylenediaminetetraacetic acid) to ethylenediamine in fucking nice yields (given the availability of the starting compound). For those here who understand why EDA is such a nice chemical (NB Birch/Benkeser Reactions at RT using Li), this might be something of a find...

What we do need is some papers where the Author's use some more OTC oxidants (the ones I just requested using Lead electrodes & electrolytic oxidation should be useful for instance), while hypochlorite doesn't seem to have the effect we'd like, succinimide can be made rather easily with it.
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Sedit

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Re: Oxiation of EDTA to Ethylenediamine (Yes, it's true)
« Reply #1 on: July 27, 2010, 02:31:52 PM »
I looked for something a while ago but any mechanism to EDA threw me for a loop at the time.

You can see the second paper IIRC it was stated that chloramines work as well for the synthesis of EDA meaning a mixture of bleach and NH3 would give the needed oxident. I would lean more towards Bromamine personally so an alkaline mixture of Bromine and NaOH treated with NH3 could prove useful.

Given that one of the products of the reaction when its running the way we wish is CO2 simple test tube oxidations should determine if its having the effect desired and what rate it is progressing at.
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no1uno

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Re: Oxiation of EDTA to Ethylenediamine (Yes, it's true)
« Reply #2 on: July 28, 2010, 02:11:27 AM »
Thanks to Java who provided the two articles attached to this post (Honestly, the contributors deserve more thanks than they get)...

The same oxidation has been done (with the formation of formaldehyde as a by-product) with lead dioxide via electrolysis in both sulfuric acid and in neutral solutions.

I'm busily looking for other routes, but the fact it can be done gives me hope... The electrolysis in a battery acid/battery electrode type route gives me a LOT of hope - any wet cell car battery - which use Lead Dioxide and Sulfuric acid NOW - should be able to be utilized directly (with some modification) to give us an amine which is EXTREMELY USEFUL (read the posts about it at WD and the RT/STP reduction of particular amino alcohols in good yield using battery lithium) and an absolute bitch to try and source and/or make...

"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."

shroomedalice

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Re: Oxiation of EDTA to Ethylenediamine (Yes, it's true)
« Reply #3 on: August 22, 2010, 09:52:53 AM »
simple if NBS can be used so can the spa brominator BCDMH and probably even TCCA as

it is an oxidation reaction.

thanx ill just do the old phenylalanine reaction but use EDTA instead to get EDA another

realy nice find no1

Enkidu

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Re: Oxiation of EDTA to Ethylenediamine (Yes, it's true)
« Reply #4 on: November 05, 2010, 08:37:23 AM »
I wonder whether acetone would be a good diluent for the rxn of EDTA with DBDMH or TCCA?

atara

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Re: Oxiation of EDTA to Ethylenediamine (Yes, it's true)
« Reply #5 on: November 07, 2010, 04:30:59 AM »
Decarboxylation of asparagine + Hoffman rearrangement, maybe?
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