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woelen
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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.
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Bezaleel
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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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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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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 
The new organic salts
Zirconium salt
[Edited on 31-8-2021 by RustyShackleford]
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TheMrbunGee
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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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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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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
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RustyShackleford
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Im back with analysis results from 1H, 13C and FTIR
orange = sample, blue = bruker spectra. a respectable fit i think, good enough to confirm the compound
Zoom-ins
1H performed in DMSO-d6, OH peak probably gone due to water in solvent.
evidence of water in the solvent, the DMSO turned blue at the bottom.
13C. was not soluble enough to provide a good sample solution with chloroform nor DMSO.
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Ormarion
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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]
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SuperOxide
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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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| 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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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]
Слава Україні !
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Boffis
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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 21 times
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kmno4
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I have received the parcel, full of chemical goods
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
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]
Слава Україні !
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Boffis
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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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Ormarion
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And there you go, new video on barbituric and violuric acid synth, if anyone speak french here feel free to add subtitles i don't really have time
from my side
https://www.youtube.com/watch?v=TN8tew9xg6A
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LeLaborantin
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Un grand merci pour ta vidéo que je viens de regarder !
Continue a en faire plein ^^
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kmno4
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Unfortunately - nothing interesting to report.
Start: urea 50g, glycine 5g
Hot air gun heating works perfecly, the rection goes as described in the paper: melting, a lot of gases, the mixture slowly turns yellow, orange and
finally deeply red, at some instant it becomes turbid and heting was stopped. The post-reaction mixture becomes bright yellow brown and is semi-solid
even below 100 C.
After cooling, urea, biuret etc... was washed out with water, keeping pH ~ 3. Finally, about 9g of bright brown, not crystalline, powder was obtained.
It surely a mixture, expected amount of UA is no more than 5 g. Unfortunaly, further attempts to purify is somehow gave nothig. I ended up with ~5 g
of the same looking powder. It is soluble in KOH solution, giving deeply yellow, practically red solution. When acid is added, a lot of semi-jelly
yellowish-grown precipitade is formed.
It does not look as UA, pity.... Besides, if cyanuric acid is present, it would be hard to separate out.
I am going to try to "do something" with it, but I doubt if UA is formed in this reaction at all.
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kmno4
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Final test, to prove (or not) this bull*t and lose no more time for it.
Oxidation to alloxan by KClO3/HCl, according to reference no.3 given here :
http://www.orgsyn.org/demo.aspx?prep=cv3p0037
About 5 g of prepared powder was taken to reaction. Effects are going to be reported very soon
.....................
Effects: no alloxan is formed. So, good bye UA from glycine and urea - without regret
[Edited on 22-5-2022 by kmno4]
Слава Україні !
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