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Author: Subject: Violuric acid salts (fantastic colors and variety)
woelen
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[*] posted on 4-8-2021 at 11:22


A picture of the dried powder in a watch glass. The material has a beautiful bright color, it really looks like it is in the picture with a deeply saturated color.



na_violurate_dry_powder.jpg - 828kB




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Bezaleel
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[*] posted on 30-8-2021 at 05:56


Woelen, did you ever get round to making any violurate salts?
Since you violuric acid is strongly pink, whereas the acid I received from Rusty is creme coloured, I'm all the more curious about your results.
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woelen
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[*] posted on 31-8-2021 at 02:54


I did not make the free acid, but the sodium salt. I made the free acid only in solution. Such solutions are colorless.
Finding time for making other salts is hard for me now. I am building a large garden house in our garden and that takes nearly all spare time at the moment. Before winter arrives it must be complete, including all streetwork around it.




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RustyShackleford
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[*] posted on 31-8-2021 at 08:33


Hello everyone! Im back with another few violurates to add to this growing collection.
Thanks to Ormarion for making and sending me pictures of dimethylaniline, 2,2 bipyridine violurates and the zirconium salt. Ormarion has produced their own violuric acid from diethylmalonate, and is working on a video about the process, although it will be in french, i think video documentation will be great for those looking to attempt the reactions.

And thanks to h0lx for making and sending pictures of 2-amino-4,6-dimethylpyrimidine and 3,5-dimethyl pyrazole salts.

Myself i havent had time to do more than triisopropanolamine since ive been busy with exams. But i do have some exciting news, thanks to an extremely generous offer 13C, 1HNMR and FTIR analysis will be done on the violuric acid i have produced aswell as possibly some high end microscope pictures of a few of the salts. Its possible that even COSY and HSQC scans will be performed. I will update with results when i get them :D

The new organic salts
noname01.png - 2.9MB
Zirconium salt
Zr.jpg - 2.3MB

[Edited on 31-8-2021 by RustyShackleford]
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TheMrbunGee
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[*] posted on 31-8-2021 at 09:35


Nice work!

I performed violuric acid preparation from alloxan hydrate and hydroxylamine HCl yesterday, but it appears that my alloxan sample is quite degraded, and reaction did not yield any acid crystals, but the yellow solution turns pink-ish when sodium hydroxide is added.

I will try to purify alloxan hydrate and try again in upcoming days.




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Ormarion
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[*] posted on 4-9-2021 at 10:36


Just a little correction, this isn't dimethylaniline violurate wich is blue, it is piperidine :) but thanks for sharing my pictures
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h0lx
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[*] posted on 31-10-2021 at 09:55


All the violurates I made sans the aminoguanidine which I fogot to add to the pic, that I managed to make with the 3g OP sent me. Will continue the exploratioin of those compounds soon

from left:

ortho toluidine
triethylamine
methylamine
guanidine
3,5-dimethylpyrazole
2-amino-4,6-dimethylpyrimidine
pyridine
triethanolamine
ethanolamine
ammonia
ethylenediamine

IMG_7115.jpg - 1.1MB
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RustyShackleford
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[*] posted on 19-11-2021 at 11:18


Im back with analysis results from 1H, 13C and FTIR :D

orange = sample, blue = bruker spectra. a respectable fit i think, good enough to confirm the compound
FTIR_comparison.jpg - 194kB

Zoom-ins
FTIR_high_comparison.jpg - 180kB
FTIR_low_comparison.jpg - 288kB

1H performed in DMSO-d6, OH peak probably gone due to water in solvent.
1H.png - 1000kB
evidence of water in the solvent, the DMSO turned blue at the bottom.
IMG_0059.jpg - 1.5MB

13C. was not soluble enough to provide a good sample solution with chloroform nor DMSO.
13C.png - 1.3MB
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Ormarion
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[*] posted on 1-5-2022 at 06:51


Last violurate made

Pink one is B rhodamine
Blue is tributylamine
Red/brown is haematoporphyrin (powder form look deep green)

I am currently making a video on barbituric and violuric acis synth

Screenshot_20220430-190430_Gallery.jpg - 314kB 20220430_181323.jpg - 3.6MB 20220430_184545.jpg - 3.6MB



[Edited on 1-5-2022 by Ormarion]
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SuperOxide
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[*] posted on 1-5-2022 at 09:33


Quote: Originally posted by Ormarion  
Last violurate made

Pink one is B rhodamine
Blue is tributylamine
Red/brown is haematoporphyrin (powder form look deep green)

I am currently making a video on barbituric and violuric acis synth


Those are great! I plan on making some of the same products eventually. They look too amazing to not try.
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Bezaleel
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[*] posted on 9-5-2022 at 01:01


Quote: Originally posted by Ormarion  
Last violurate made

Pink one is B rhodamine
Blue is tributylamine
Red/brown is haematoporphyrin (powder form look deep green)

I am currently making a video on barbituric and violuric acis synth
[Edited on 1-5-2022 by Ormarion]
I'm looking forward to seeing that video
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kmno4
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[*] posted on 12-5-2022 at 14:55


Quote: Originally posted by Boffis  

Guano -> uric acid -> alloxan -> alloxan-5-oxime (violuric acid)

Hm....
There is very old reference (see "Uric acid" at Wikipedia), describing uric acid formation from glycine and urea*.
If it really works, then it makes preparation of VA very cheap, even if total yield of this multistep synthesis is low. I have ordered some larger amount of glycine to test this UA preparation, just for fun.
But maybe someone here already tried this ?
* it is hard to imagine exact machanism of this high temperature reaction, but it seems that it has something to do with Strecker degradation.

ps. playing with guano is not my cup of tea

[Edited on 13-5-2022 by kmno4]




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Boffis
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[*] posted on 13-5-2022 at 03:42


Woow its a while since I posted that.

Like you say if you can make uric like the paper describes it would be excellent even if not very efficient. The original paper doesn't state the yield.

The di-potassium and di-sodium salts are fairly soluble in a small excess of the same caustic alkali and then the free acid ppt'd with dilute HCl or sulphuric acid. The mono-sodium salt can be ppt'd by sodium bicarbonate. So it may be possible to avoid the precipitation with silver and the H2S treatment. The solubility of free uric acid is very low unless certain organic bases are present. Dont overheat the solution or heat for long periods, this decomposes the uric acid.

For those that don't have access to the paper or can't read German I have attached a quick translation.

@kmno4; What's wrong with the Peruvian bird guano? The stuff sold as an organic fertilizer is sterilized and the uric acid concentration is >20%.

Attachment: Preparation of Uric acid Monatshefte Horboczawski 1882 English.docx (14kB)
This file has been downloaded 10 times
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kmno4
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[*] posted on 16-5-2022 at 03:13



I have received the parcel, full of chemical goods :D
I do not trust mentioned paper very much, it looks more like patent, but not scientific publication. I could not find any more paper with confirmation of the procedure by Horbaczewski.
It is the simplest one, among the others, much more complicated methods of UA preparations - and no-one exploits it ....
But I have now 250 g of glycine to waste, we will see:P
I am going to use hot air gun, instead of ancient metal bath.

ps_1. this extremelly low solubility of UA, compound with very polar molecules, still surprises me, hah.

ps_2. preparation of barbituric acid from malonic acid, urea and Ac2O in AcOH is in my reach at once but I want to try UA method, just for (scientific) fun.

[Edited on 16-5-2022 by kmno4]




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Boffis
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[*] posted on 16-5-2022 at 05:33


Hi kmno4, The paper is very old and is very much on a par for the period I would say, having looked at many old papers from this period. I am quite sure the results will be reproducible, the problem is that it may not be uric that is produced, he also doesn't give a yield either! I suspect that isocyanuric acid is also produced along with diketopiperazines and, in order to produce uric acid, a lot of ammonia would need to be expelled so guanidine is another possible byproduct. The isocyanuric acid may be difficult to remove from the uric acid. I would try it myself but I am currently away from home.

The low solubility of uric acid is almost certainly due to the many potential hydrogen bonding sites on the molecule.

Please let us know how you get on.
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