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Author: Subject: Copper(II) Aspirinate Synthesis
bfesser
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[*] posted on 16-2-2008 at 18:19


If you add baking soda, you can precipitate the copper out as the carbonate. But be careful, it will foam a lot. Then you can filter it, rinse it, dry it, and <strong>very carefully and slowly</strong> dissolve it in dil. H<sub>2</sub>SO<sub>4</sub>. Add the sulfuric acid dropwise with lots of swirling. If you can do this carefully enough to dissolve most of the solid, but just leave a little bit of solid remaining, you can filter it out and evaporate the filtered liquid down to copper(II) sulfate again.

As for the sodium acetate, you might as well just dump it. It would probably be more expensive to recover it than to just dump it. You can always make more with vinegar and baking soda.

It's also important to note that copper solutions are considered to be harmful to the environment, and you should avoid pouring such solutions down the drain at all costs. I always precipitate my copper out and throw it away if I end up having any in my filtrates from various syntheses. Sodium acetate, on the other hand, is pretty much harmless.

[Edited on 2/16/08 by bfesser]




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[*] posted on 16-2-2008 at 19:05


I don't have any sulfuric acid (in reality I have but it's a yellow solution from drain cleaner, almost useless) but my main concern would be to get the copper out so I'm thinking that I can precipitate it as the hydroxide and filter it. I believe this way I could also get all my copper out and throw away the rest.
On the other hand, I dissolved some of this solution in 70% isopropanol and much to my surprise a clean green-blue precipitate forms. Although I believe it to be the acetate I'm not very confident of this, however, I think this could also be an alternative way to get my copper out of solution. Any ideas other ideas of what the precipitate may be? The original solution is only copper(II) sulfate and sodium acetate (a bit of excess acetic acid) in which the only green-bluish precipitate would the copper acetate as far as I know.
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[*] posted on 16-2-2008 at 20:21


If you read the revision of my last post, I mentioned that copper(II) sulfate will precipitate out of an aqueous solution of isopropanol, provided the isopropanol is in high enough concentration. Not sure if the same would be true of copper(II) acetate. I suppose you could always dissolve a little of the precip in water, then add a little of a barium salt, if you have the hydroxide or chloride, as a qualitative test for sulfate (forms a white precipitate). Anyone else have any ideas?



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[*] posted on 16-2-2008 at 20:38


I did read it but it's exactly why I considered the green-blue precipitate to be the acetate and not the sulfate: the isopropanol solution remains blue (as I mentioned it's 70%, "significantly" wet to not be considered highly concentrated). I think I'll post some pictures on the precipitate tomorrow so that you may compare and see what I mean.
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[*] posted on 28-3-2008 at 08:38


At the bottom 'Basic Recipe' it says to use KHCO3 (pottasium bicarbonate) could NaCO3 (sodium carbonate) be substituted?



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[*] posted on 28-3-2008 at 11:02


Chelation therapy is looked at as a possible way to prevent Alzheimers desease. Could this mean that aspirin might help prevent Alzheimers?



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[*] posted on 28-3-2008 at 15:25


Sodium carbonate should work equally well. Please post your results. I know I've tried this before, but I can't remember if I had any issue with hydrolysis of the acetylsalicylic acid. I'll retry it when I get a chance.

Both copper and aluminum will form insoluble complexes with acetylsalicylic acid. I do recall seeing somewhere that someone's found a correlation between aluminum concentration and Alzheimers in the brain--I think. Other than that, I have no idea. Can anyone find any research on this subject? I haven't seen any yet.
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[*] posted on 28-4-2008 at 03:06


Hello everyone,

Apologies for digging up an old thread, but there is now a Youtube vid with pictures and method posted on this synthesis and it is on our website.

Youtube link: http://youtube.com/watch?v=PNJfWYKcjKY

Website link: http://www.freewebs.com/ozonelabsinc/syntheses.htm

If there are any questions/comments please get back to us!

Regards,

Ozonelabs




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[*] posted on 9-6-2008 at 12:48


Have you checked the identity/purity of your product? The color seems a bit off, even for a fine precipitate--although it could just be the camera. Also, it shouldn't be difficult to vacuum filter. What grade of filter paper did you use?

To test the identity of your compound, just add a little vinegar to a sample. If it dissolves, it's likely to be copper(II) carbonate. Adding a little HCl to another sample should leave a white precip of ASA and a blue CuCl<sub>2</sub> solution.

[Edited on 6/9/08 by bfesser]
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[*] posted on 1-3-2009 at 16:49


I tried synthesizing some Copper Acetylsalicylate two days ago. There seems to be little need to react the ASA with NaHCO3. I mixed ASA with Copper(II) Carbonate, and added a few drops of water. The slurry began to bubble slowly and over a few minutes changed from pale green to a saturated bluish-aqua color.

Upon drying (by evaporation at room temperature), the residual powder is a deep aqua color. The trace of green may be due to residual CuCO3, or residual insoluble component in the aspirin tablets. I'll look into this later tonight.




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smile.gif posted on 20-6-2013 at 20:13
Cobalt, nickel, and other metal aspirinates


First off, I want to say it feels good to be back on ScienceMadness, being a chem major and the research takes a serious toll on your freetime. But it is good to see you all, especially my old buddy Hexavalent.

Also, I think this belongs in beginnings?? But, it has been a while and maybe rules have changed.

Anyways, down to some inorganic complexes. I have seen a few threads and posts on copper aspirinate, which is good and dandy, but is acetylsalicylic acid a strong enough field ligand to bind any number of transition metals? Say, for example nickel or cobalt? Maybe even iron? Or is copper just the special oddball (Like usual)?

Well anyways, this is largely for discussion, since I'm going to peruse the literature to see what I come up with. I will update you on the progress of this.

Also, for reference, here is the wikipedia link to copper aspirinate to show the dimer structure. Wiki
I also like the synthetic approach the wiki gives to synthesizing the complex.




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[*] posted on 21-6-2013 at 00:17


Interesting. I might give cobalt and nickel a shot with salicylic acid later this weekend. I have nickel sulfate, nickel chloride and cobalt chloride at my lab. Off the top of my head I can't think of any other colorful metal salts that I have lying around. I have no aspirin available. I'll report my findings.

Edit: Cobalt nitrate

[Edited on 21-6-2013 by Lambda-Eyde]




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[*] posted on 21-6-2013 at 05:12


I found a zinc complex that had been studied, so this sounds like a possibilty. However, they have no method for synthesis in this paper.

Anne Spasojević-de Biré, Nouzha Bouhmaida, Aleksandar Kremenović, Georges Morgant, and Nour Eddine Ghermani. Experimental Electron Density and Electrostatic Potential Analysis of Zinc(aspirinate)2(H2O)2 Complex:  A 3d10 Metal Bonding to a Drug Ligand. The Journal of Physical Chemistry. November 22, 2002, pp 12170–12177.

I will do some aspirin extractions tonight and get enough material to study this over the weekend.

[Edited on 21-6-2013 by sargent1015]




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[*] posted on 21-6-2013 at 05:30


This is a pretty neat article too, salicylic acid complexes of copper are possible! Which can be a problem for the amateur chemist that overcooks his acetylsalicylic acid reaction and clams that is the complex he has obtained.

Orally active antioxidative copper(II) aspirinate: synthesis, structure characterization, superoxide scavenging activity, and in vitro and in vivo antioxidative evaluations. Fujimori, T. ; Yamada, S. ; Yasui, H. ; Sakurai, H. ; In, Y. ; Ishida, T.
JBIC Journal of Biological Inorganic Chemistry, 2005, Vol.10(8), pp.831-841


I guess this is no longer a beginnings post :P

[Edited on 21-6-2013 by sargent1015]




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[*] posted on 21-6-2013 at 05:33


Welcome back. I have the feeling that iron won't make a stable complex, cobalt, copper, will and I don't know for nickel. For sure it is not a highly coordinating complexing agent. Iron generally does not complex well.

If one had uranyl acetate, I think it might make a pretty colorful complex.




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[*] posted on 21-6-2013 at 05:37


Hey Plante, thanks for welcoming me back :D

In regards to your iron statement, and of course not to be rude or undermining, I just found an article on its synthesis :P

Synthesis and magnetic properties of the iron(III) aspirinate complex, [Fe 3O(C 9H 7O 4) 6(H 2O) 3](C 9H 7O 4)·H2O. Lynch, S.K. ; Frazder, D.R. ; Carlisle, G.O.
Journal of Molecular Structure, 1982, Vol.82(1), pp.151-153.

Fairly old one at that, not the medicinal activity of copper aspirinate, not surprisingly.

7 moles of "aspirinate" to 1 mole iron with a water molecule complexed.

[Edited on 21-6-2013 by sargent1015]




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[*] posted on 21-6-2013 at 06:29


Very interesting, but the question is it stable?

Hmm, I'll have to check more into this.




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[*] posted on 21-6-2013 at 07:01


yes this amateur chemist did over cooked the aspirin because my copper aspirinate looks like copper carbonate and isnt dark at all. i never gave up on wanting to do it again even though my Salicylic acid was very fluffy and crystally i never knew where i went wrong. i only have coffee warmers and not a regulated heat source like a heated stirer so i have to switch back and forth from heat to stirer.
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[*] posted on 21-6-2013 at 09:18


Quote: Originally posted by sargent1015  
Also, for reference, here is the wikipedia link to copper aspirinate to show the dimer structure. Wiki
I also like the synthetic approach the wiki gives to synthesizing the complex.

I'm glad you like the synthetic approach, I wrote it. :D

I've done a fairly extensive literature search over the years on copper(II) aspirinate and related complexes. Perhaps, if you're interested, I'll dig out my file folder (yes, hard copy!) later and post what I have found. I also have performed experiments with several other cations, and have notes on this. I'll have to look those up, as well. They probably make up a third of my first chemistry laboratory notebook. Sorry, I don't recall precisely which complexes I managed to prepare (cobalt?).

[edit]
From what I remember, I tried copper, zinc, iron, cobalt, and magnesium.

[Edited on 7/8/13 by bfesser]




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[*] posted on 21-6-2013 at 09:33


Quote: Originally posted by bfesser  

I'm glad you like the synthetic approach, I wrote it. :D


Well what do ya know!? Hahaha, thanks for looking all this up. I'd love to see your notes on the subject and hopefully repeat/expand on your studies. Hopefully I get some decent results.

The key procedure I'm seeing cited for these complexes is using a weakly basic buffer (K/Na HCO3) and adding the aspirin and corresponding salt. Seems simple enough, though I only found iron and copper complexes in the literature. These should be wonderfully colored compounds (Minus iron, unless you like brown :P ).




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[*] posted on 21-6-2013 at 09:36


Quote: Originally posted by bfesser  
(I'll take some pictures of what the solution should look like before you decant and at the end of the procedure.)
I just noticed that I promised photos five years ago and never delivered. Sorry about that. Maybe some day...

Regardless, repeat washing until the supernatant is clear.

[Edited on 7/8/13 by bfesser]




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[*] posted on 22-6-2013 at 10:43


Alright, so as far as forum etiquette as I work out some different complexes, should I form a new thread describing the syntheses or just continue here?

Also, I am currently making the iron and copper complexes, in case anyone was curious :P




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[*] posted on 22-6-2013 at 15:56


Personally, I would like to see them all in one 'aspirinate' thread.



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[*] posted on 22-6-2013 at 18:58


Well, for now, just updates on my progress:

Copper aspirinate made (easy)
Iron aspirinate made, but the solid particulate is too fine to collect with coffee filter paper. Going to try to get my hands on good filter paper.

To be done:
Cobalt aspirinate
Salicylic acid complexes
Copper mixed aspirinates and imidazole complexes (different ratios)




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[*] posted on 22-6-2013 at 19:19


i wonder if chromium/cobalt alloy will work as well because i have dental metal alloy that i believe is chromium/cobalt.it dissolved rather quickly in hot hydrochloric and turned light purple when i added sodium carbonate.btw this alloy is hard as shit to work with i mean it melts but it doesnt run and the glob will let the flame go through.the flame goes through the glowing mass like the exterminator's fist going through the mercury man's face. correction:the dissolved alloy was bluegreen and only after i added ammonium hydroxide did it turn indigo.i wanted to know if it made a blue complex as with copper

[Edited on 6-23-2013 by cyanureeves]
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