Sciencemadness Discussion Board

Acetylene dicarboxylic acid - treatment for lead poisoning

numos - 28-5-2014 at 22:19

How can I acquire acetylene dicarboxylic acid... would it be better to synthesize myself (how?) or ask my school to buy it from Sigma Aldrich? (not cheap) Or if anyone has some... :)

Here's why I need (badly want) it:

I was browsing Wikipedia and came across lead-poisoning, to which Dimercaptosuccinic acid is a chelating agent and a potential treatment.

I am interested in preparing this substance as a novelty more than an actual treatment. According to this:
http://www.google.com/patents/US4550193

It is a very simple reaction between acetylene dicarboxylic acid and sodium thiosulfate in an acidic setting. Then heat the product (tetrasodium 2,3-bisthiosulfatosuccinate) with methanol and HCl for two hours, then then after cooling the solid is filtered and recrystallized from methanol.

I have everything except the acetylene dicarboxylic acid

Metacelsus - 29-5-2014 at 05:57

You could react fumaric acid with bromine to form 2,3-dibromosuccinic acid, then do an elimination reaction.

PHILOU Zrealone - 31-5-2014 at 07:25

You may aswel brominate or chlorinate tatric acid (HO2C-CHOH-CHOH-CO2H) to get also dibromosuccinic acid or dichlorosuccinic acid and then do conventional dehalogenation in basic media (NaOH/KOH in ethanol) with heating/reflux.

[Edited on 31-5-2014 by PHILOU Zrealone]

numos - 31-5-2014 at 10:19

Could methanol work as well? I don't have any ethanol right now.:(

PHILOU Zrealone - 31-5-2014 at 10:54

Quote: Originally posted by numos  
Could methanol work as well? I don't have any ethanol right now.:(

Maybe but I think it boils a bit too low a temperature...

UnintentionalChaos - 31-5-2014 at 20:01

How about consulting the freely available literature....

http://www.orgsyn.org/Content/pdfs/procedures/cv2p0010.pdf

numos - 31-5-2014 at 20:13

Quote: Originally posted by UnintentionalChaos  
How about consulting the freely available literature....

http://www.orgsyn.org/Content/pdfs/procedures/cv2p0010.pdf


Thank you, and this was the final obstacle. I have ordered Fumaric acid, and will conduct the entire synthesis in a week or so and then do a formal write up here. Thank you all for your help!

Also just a note, directed to everyone: I think the reason many people ask is not because they don't look, but because they want assurance. Chemistry is unforgiving and a small mistake can be lethal, and there are "formal" papers that have dangerous errors in them. Don't get me wrong - there are lazy people here, and I can't say I'm perfect in that aspect either, but still... food for thought!