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Making EDDA

This discussion is about synthesizing ethylenediamine diacetate (EDDA) from acetic acid and ethylenediamine. One user asks if DCM can replace ether as a solvent, to which others respond that isopropanol or precipitating with ethyl acetate may work better as EDDA would be soluble in DCM. Another user provides the melting point of EDDA as 117-118°C according to a source, though they obtained a higher melting point. EDDA is noted to be stable if stored properly and drying under vacuum is recommended.

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42 views

Making EDDA

This discussion is about synthesizing ethylenediamine diacetate (EDDA) from acetic acid and ethylenediamine. One user asks if DCM can replace ether as a solvent, to which others respond that isopropanol or precipitating with ethyl acetate may work better as EDDA would be soluble in DCM. Another user provides the melting point of EDDA as 117-118°C according to a source, though they obtained a higher melting point. EDDA is noted to be stable if stored properly and drying under vacuum is recommended.

Uploaded by

M. Shehryar Khan
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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https://www.sciencemadness.org/talk/viewthread.php?

tid=15440

Author: Subject: EDDA


xwinorb posted on 4-2-2011 at 15:36
Hazard to Others
EDDA

I have one recipe for making EDDA from acetic acid and ethylenediamine, using
ether as a solvent.
Posts: 100
Registered: 9-8- I have one question, would that be OK to replace ether with DCM ?
2005
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Mood: No Mood

bbartlog posted on 4-2-2011 at 16:48


International
Hazard

A recipe, you say? Why not try these forums: http://www.talkfood.com/forum/


More seriously, how is anyone supposed to answer your question without you
providing a little information about the synthesis? 'EDDA' isn't even a commonly used
acronym as far as I know.
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smuv posted on 4-2-2011 at 17:12


National Hazard

You could try doing it in dry isopropanol, after stirring for a while, you could
precipitate the the EDDA by adding Ethyl acetate or 2-butanone and chilling the
solution. DCM is not great beecause I think EDDA would be pretty soluble in it
Posts: 842 (although you could do the same thing as here, run it in DCM and precipitate the stuff
Registered: 2-5- by adding a solvent EDDA is insoluble in).
2007
Member Is Offline The synth might work OK in neat ethyl acetate too. Play with it on a small scale and
go from there.
Mood: Jingoistic

mewrox99 posted on 5-2-2011 at 03:40


Hazard to Others

What is EDDA?

Ethylenediaminediacetic acid?
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https://www.sciencemadness.org/talk/viewthread.php?tid=15440

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xwinorb posted on 5-2-2011 at 09:39
Hazard to Others

I mean ethylenediamine diacetate, I think it is also know as ethylenediammonium


diacetate.

Posts: 100 CAS : Ethylenediamine 107-15-3


Registered: 9-8- CAS : Ethylenediamine diacetate 38734-69-9
2005
Member Is Offline Also, does someone knows what the melting point of the diacetate is ?

Mood: No Mood It is easy to find info and MSDS on the ethylenediamine, not so much on the
diacetate salt. Any reasons for that ?

I hope the diacetate salt is stable. Any special precautions ? Also, can it be dried in a
hot plate at low heat ?

I am asking this because the ethylene diamine MSDS caused me some concerns.

Thanks to the suggestions, I think I will try a low scale experiment soon.

[Edited on 5-2-2011 by xwinorb]

turd posted on 6-2-2011 at 00:52


National Hazard

I've used various solvents and never had problems. I believe DCM would work.
Recrystallize from a small amount of e.g. methanol to get good purity.

Posts: 800 Quote: Originally posted by xwinorb


Registered: 5-3-
2006 Also, does someone knows what the melting point of the diacetate is ?
Member Is Offline

Mood: No Mood
According to Bannard & Casselman (Can. J. Chem. 41, 92-107 (1963)) it's 117-
118°C, but I'm quite sure that on good samples I got higher mps (IIRC 120°C).

Quote:

It is easy to find info and MSDS on the ethylenediamine, not so much on the
diacetate salt. Any reasons for that ?

Ethylenediamine is produced on megaton scales but nobody cares about the


diacetate?

Quote:

I hope the diacetate salt is stable. Any special precautions ? Also, can it be
dried in a hot plate at low heat ?
https://www.sciencemadness.org/talk/viewthread.php?tid=15440

It's stable if stored in an air tight container. Drying under vacuum very much
recommended. There's a phase transition at ~75°C.

Sciencemadness Discussion
Board » Fundamentals » Beginnin » Beginnings
gs » EDDA

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