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Author: Subject: Copper(II) Aspirinate Synthesis
HeYBrO
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[*] posted on 7-2-2014 at 15:32


Quote: Originally posted by sargent1015  


I should have clarified, while it is cool and dandy to make copper benzoate, I do not need a huge surplus of it. So I made the benzoic acid, isolated it, and used only the amount I wanted for the copper benzoate synthesis.



I see, very nice. Did you use hardware store toluene? I want to do this but I don't really want thiophene containing wastes associated with the purification, as i don't know how to destroy it/ dispose of it. Any ideas?




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sargent1015
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[*] posted on 7-2-2014 at 19:22


Actually, yes! It was hardware store toluene, I even took a 400 MHz NMR after the synthesis and it was remarkably pure.



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smile.gif posted on 24-2-2014 at 22:19


Also, toluene can be cleaned up with a couple sulfuric acid washes (Enter Vogel reference here). Did you try the synthesis yet?



Well, I also have some pictures since everyone loves that.

First, this is the aspirinate/imidazole complex (Maybe?). It is very waxy and a deep, dark blue.

100_1252.JPG - 160kB

Second, a little copper benzoate!

100_1254.JPG - 198kB




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[*] posted on 17-11-2014 at 22:39


In this thread: http://www.sciencemadness.org/talk/viewthread.php?tid=26316 a paper is given on the synthesis of aspirinates of copper, nickel, cobalt, and zinc (Journal of Enzyme Inhibition and Medicinal Chemistry, 2002, Vol 17 (2), p 87-91). It's another lousy paper, riddled with errors.

First of all, it gives exactly one synthesis, that of a cobalt aspirinate, and declares that the other compounds were made by the same procedure, only with different molar ratios of the reactants. Insufficient experimental data!

Second, the formulation for the compounds are given as ML2, MCl2L2, and M2L4 (where L = aspirinate or acetylsalicylate). Since these are divalent metals, the formulation with two chlorides and two aspirinate anions is clearly wrong (that would require a tetravalent metal).

Thirdly, how on earth is one supposed to get one of these three complexes through "different molar ratios of the reactants", when there are two aspirinate anions for each metal in every single proposed formulation?




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[*] posted on 22-3-2015 at 07:18


Well hi there guys! I have not been working on anything for this forum in quite some time since I moved across the country and started grad school in organic chemistry. Not only did I not have the space to haul all of my equipment, but my time outside of lab anyways is quite limited, so I will live vicariously through you guys!

Has anyone done asprinate work in awhile? Maybe I can revitalize this thread and get someone to pick up where I left off :P

Anyways, hope everyone is doing well :)




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[*] posted on 22-3-2015 at 12:47


I have around 10g of ASA in my lab ready to extract when I find time so I would be interested in trying acetylsalicylate metal complexes; after I finish my current project, Nd extraction with organic ligands.

I do have to say my preferred method of ASA separation is a bit different; after dissolving the tablets in an appropriate volume of warm ethanol, filter and add the same quantity of distilled water (the ASA crystals precipitate which is really pretty), let the crystals settle. Decant into a filter, wash with cool water and then leave to dry (don't evaporate with heat, this ends with thermal decomposition).

A benefit to this is that the ethanol can then be distilled and used again and all named binders (in my source at least) are insoluble in ethanol, the efficiency is also very high due to the insolubility in low concentration ethanol.
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[*] posted on 22-4-2015 at 10:52


Quote: Originally posted by bfesser  
I replicated the experiment shortly after that post, substituting 0.9 mm pencil lead, and got very poor results. I did get some product, but the crystals are much smaller than claimed by the original authors—I didn't bother to recover them.
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[*] posted on 22-4-2015 at 11:10


Please use drinking water to improve your results and you can optionally replace the pencil lead by a copper wire as cathode. Interrupt the power supply when a black powder (CuO) begins to appear but let the chemical reaction finish, this means the blue powder (Cu(OH)2) disappears.
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[*] posted on 22-2-2017 at 00:49


So I followed the steps for the synth of copper acetylsalicylate. I didn't get an immediate formation of precipitate, just a formation of a greenish blue solution. I checked an hour later and crystals were forming on the sides and the base. The crystals are insoluble in water, have and greenish bluish hue and And slightly remind me of tiny acetate crystals. Have I done it right?
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[*] posted on 10-9-2017 at 00:39
Copper (II) acetylsalicylate precipitation


I did a precipitation with copper II sulfate and sodium acetylsalicylate and the product did not precipitate immediately. instead it crystallized on the walls of the container over some time. Was this precipitation? I do not understand what happened.
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[*] posted on 10-9-2017 at 11:38


Try posting your entire procedure, sources, pictures, and how your prepared the reagents in your reactions. Your post is not detailed enough. IF you can read it in 30 seconds its most likely not worth posting.



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10-9-2017 at 14:33
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[*] posted on 28-9-2017 at 11:53


So did anyone manage to get an aspirinate other than that of copper? We've got cobalt(III) and iron(III) mentioned in the thread, but were these followed up to be sure that they were actually the desired compounds?



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[*] posted on 29-9-2017 at 17:00


I just tested a solution of aspirin, dissolved in acetic acid and adjusted to a pH of 7, with cobalt chloride and manganese chloride- no precipitate was observed.



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[*] posted on 24-3-2018 at 02:02


after crystalising, the copper aspirinate deposited on the walls of the flask, as it can be seen from nice smooth shards. however, we got these goldish needle-like crystals that don't really fit any description.

the synthesis was done with copper sulfate and pure ASA

an EDS analysis was done and it shows the blue aspirinate and the needle-like golden crystals to have a somewhat similar composition (the gold needles contain less copper and more organic)

AK_Leica2018_0054.jpg - 5.9MB
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[*] posted on 13-9-2020 at 18:53


I also had a go at copper aspirinate, and then did some test tube checks with the metal salts I had available to see if anything else obviously reacts with sodium aspirinate. The copper first:
- First step to make the sodium aspirinate in solution:

Na2CO3 + 2C9H8O4 = 2C9H7O4Na + CO2 + H2O

- 4.7g NaHCO3 (baking soda from the local department store) was dissolved in 50ml warm water, obtaining a clear solution.
- Add 10g aspirin powder (lab reagent quality, bottles says "Aspirin") in stages to the stirred solution. Bubbles followed each addition, wait for bubbling to subside before adding more. All 10g dissolved, plus an 11th gram, but the 12th gram did not all dissolved. Filter the solution to remove the unreacted aspirin.
- 6g CuSO4.5H2O in 20ml water, heat a bit to fully dissolve. Slowly pour the CuSO4 solution into the sodium aspirinate solution to get the double displacement:

4C9H7O4Na + 2CuSO4*5H2O = C36H28O16Cu2 + 2Na2SO4 + 10H2O

- Stir for some 20 minutes, dark blue solution. Photo below.
1 color after double displacement.jpg - 746kB
- Vacuum filter and wash once with excess of cool water in the funnel. Photo below of the wet remainder. The filtrate had a very pale magenta color.
2 wet remainder.jpg - 490kB
- Dry remainder on steam bath till weight reduction slowed to near nothing. Dry dark blue powder, 10g recovered. Photo below.
3 dry copper aspiorinate.jpg - 471kB


I then made another solution of sodium aspirinate by using the same procedure as above. I dissolved various metal salts that I have in the shed one by one in a bit of water in a test tube and added a bit of the sodium aspirinate to see if there was an obvious ppt. Observations:
- MnSO4 - no obvious reaction.
- (CH3COO)2Co - no obvious reaction.
- Cr(NO3)3 - no obvious reaction.
- Ce(NH4)4(SO4)4 - dark olive color ppt.
- (CH3COO)3Er - nothing.
- FeSO4 - solution turns dark brown color.
- Fe2(SO4)3 - solution turn very dark purple color with brown ppt.
- Ni(NO3)2 - no obvious reaction.
- TiCl3 - brown ppt, difficult to remove from test tube.
- SnCl2 - light yellow ppt, but when I retried on a larger scale I got a white very sticky mess.







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