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Author Topic: EDTA decomposition  (Read 53 times)

Sedit

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EDTA decomposition
« on: September 27, 2009, 10:07:05 PM »
Various papers detailing decomposition reactions of EDTA. My main goal in the end is to find one that ends in EDA but the closest I have come yet it a paper that details the decomposition in an acidic enviroment that proceeds through EDA favoring the second reaction path that ends in for formation of formic acid from EDTA in the presences of TiO2 and light.

The reaction of it with dilute aq ammonia looks like it could work to produce EDA from EDTA but the problem comes from the need for an autoclave which I do not want to work with. I think it could work at lower temperatures though with a much longer reaction time but that has yet to be seen.

At first I was thinking that a simple decarboxylation would yeild the desired product but my head was just in the gutter and didn't think that I would be left with the tetramethyl equivalent of EDA which is unacceptable.
« Last Edit: September 27, 2009, 11:36:21 PM by Sedit »
There once were some bees and you took all there stuff!
You pissed off the wasp now enough is enough!!!

2bfrank

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Re: EDTA decomposition
« Reply #1 on: September 27, 2009, 11:37:58 PM »
Ha, been looking at this too..the only article Ive found for free, and other than what you have presented, is attached.

The ammonia reaction,that you attached Sedit,I think takes pressure, which I'd prefer not to deal with, but it just may have to be..The attached uses 1,2-phenylenediamine (a weak base) and itself brought about a biologically active reagant.(benzo derivitive) I wasn't interested in that product, just their schematic for the decomposition. Their analytical measurements were more in line with the benzo intermediates, and due to this, I was not going to post. Yet their schematic for the decomposition states the temperature of 260C or greater to finally result in the loss of both carboxylic acid groups.. So I am beginning to learn a little bit about microwave tech, and just wondered how hot does super heated solutions get when hit with those wavelengths..Perhaps finding the solubiliy factos of the NaEDTA, and see if their is something that it can dissolve in, and be able to be heated to that mark.. I really haven;t put the time into this inquiry, and  :)'d when I noticed that you, and I dare say many others, have been thinking a little of this.. THe diamine, if or when its sorted, would be dam useful, so I will include the article, just in case it does help in someway....

The attached article is as follows..

Based on the reaction products of ethylenediaminetetraacetic acid (EDTA) with 1,2-
phenylenediamine (o-PDA), a novel thermal decomposition pathway of EDTA is proposed. The
strong acidic medium and the presence of o-PDA facilitate the decomposition of EDTA as
evidenced by the relatively lower reaction temperature. In addition to the steps described in
literatures, rearrangement process is involved in the decomposition reaction. The rearranged
intermediates condense with o-PDA, forming an unexpected biologically active compound 2,2,4-
trimethyl-3H-5-hydro-1,5-benzodiazepine, thus provides the possibility to explore an alternative
decomposition mechanism for this widely used chelator.

Perhaps one gets the diamine, and perhaps some R and R to boot... ;D

I also haven't read the papers you attached, so hopefully I hven't double up..Time etc, bzy busy
« Last Edit: September 27, 2009, 11:44:34 PM by 2bfrank »
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