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Apr 17 2016 10:42am
(read the last couple of sentences for the question)
Dunno how many here thats any good with (organic) chemistry, but I am gonna try because why not :)

Currently got a school project, where we want to optimize (in terms of saving money, time etc) a disulfiram (Antabus) synthesis.

We got an "original" recipe, where the main reaction is:

(in words, you mix (C2H5)2NH and NaOH together, when the temperature gets low enough you add the CS2 slowly. when the CS2 have been added, you wait 10-15 min. and then start adding the oxidizing agent, the "standard" one is K3Fe(CN)6, slowly.)

Currently we are trying different kind of oxidizing agents.
The "standard" oxidizing agent for this reaction, is K3Fe(CN)6.

With the standard oxidizing agent, disulfiram (antabus) is a white solid (hint of green-ish) and when smelted, a green-ish liquid.

At the moment we have tried these oxidizing agents:
H2O2 (no product, tho the Mother liquor had the "right" green-ish color)

KMnO4 (maybe product, but got solid MnO2 (black stuff) mixed with the product. the Mother liquor were black/ dark brown-ish), and not sure how/if we can extract antabus from the MnO2

FeCl3 (maybe product. However, the solid extracted from the mother liquor were black. The mother liquor were also black)

I think my teacher gave a hint about the oxidizing agent, because he asked why/if there were a reason for why the (oxidizing agent) iron has to be complex bound (not sure if you can translate that directly lol :D ). And honestly I have no idea atm. lol


So, the question is if you guys know any oxidizing agents, that you think will work for this synthesis.
And if anyone can help with how the reaction might have been with H2O2 and FeCl3, as oxidizing agents (and why they didnt work)
(and why the iron is/ have to be complex bound for the "standard" reaction)

(might got more questions, if there is someone that even can help me with the above ones ^^ Will ofc. don8 if your answer is satisfying :) )

This post was edited by dfgdsa on Apr 17 2016 10:46am
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Apr 20 2016 09:32pm
Quote (dfgdsa @ Apr 17 2016 11:42am)
(read the last couple of sentences for the question)
Dunno how many here thats any good with (organic) chemistry, but I am gonna try because why not :)

Currently got a school project, where we want to optimize (in terms of saving money, time etc) a disulfiram (Antabus) synthesis.

We got an "original" recipe, where the main reaction is:
http://i.imgur.com/cCjcO9E.png
(in words, you mix (C2H5)2NH and NaOH together, when the temperature gets low enough you add the CS2 slowly. when the CS2 have been added, you wait 10-15 min. and then start adding the oxidizing agent, the "standard" one is K3Fe(CN)6, slowly.)

Currently we are trying different kind of oxidizing agents.
The "standard" oxidizing agent for this reaction, is K3Fe(CN)6.

With the standard oxidizing agent, disulfiram (antabus) is a white solid (hint of green-ish) and when smelted, a green-ish liquid.

At the moment we have tried these oxidizing agents:
H2O2 (no product, tho the Mother liquor had the "right" green-ish color)

KMnO4 (maybe product, but got solid MnO2 (black stuff) mixed with the product. the Mother liquor were black/ dark brown-ish), and not sure how/if we can extract antabus from the MnO2

FeCl3 (maybe product. However, the solid extracted from the mother liquor were black. The mother liquor were also black)

I think my teacher gave a hint about the oxidizing agent, because he asked why/if there were a reason for why the (oxidizing agent) iron has to be complex bound (not sure if you can translate that directly lol :D ). And honestly I have no idea atm. lol


So, the question is if you guys know any oxidizing agents, that you think will work for this synthesis.
And if anyone can help with how the reaction might have been with H2O2 and FeCl3, as oxidizing agents (and why they didnt work)
(and why the iron is/ have to be complex bound for the "standard" reaction)

(might got more questions, if there is someone that even can help me with the above ones ^^ Will ofc. don8 if your answer is satisfying :) )


I haven't done any chemical synthesis problems and/or inorganic chemistry (coordination complexes) in too long... My guess would be to form a coordination complex with ligands at least greater than or equal to in strength as OH - ie K3Fe(OH)6

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Apr 21 2016 11:03am
How does your work-up looks like?
How do you determine the conversion?
Do you use the same protocol for every oxidizing agent?
MnO2 should be pretty easy to remove.
H2O2 should be definitely working as oxidizing agent.

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