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Kamikaza
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I did the experiment today, and these were my findings:
First I mixed an equal amount of ureum and citric acid. This was heated without solvent on a hotplate, and it slowly dissolved (probably in the water
of crystallisation). It slowly turned yellow, then orange, then red, then black. This probably only is because of the increase of concetration of
citrazanic acid, as it is quite a powerfull yellow dye. When it was dilluted, it became yellow again. When acid was added, it turned slighty more
yellow. When natrium hydroxide was added a white precipitate was formed. This was quite unexpected as wikipedia stated that citrazinic acid should
precipitate in acid . Then I filtered the solution, and boiled it down. Now I
have some blood red crystals. So it looks like the ureum citric acid syntheses was quite succesfull. I don't have any solid information about the
yields, because my scale is broken, but it doesn't look to bad  .
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Random
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Strange, what could be that white precipitate? Those blood red crystals could be citrazinic acid, though, I am not sure what is that we are making:
Citrazinic acid, citrazinamide or ammonium citrazinate? I will see tomorrow if my solution will make some crystals. By the way, what is the acid you
are using?
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distorto
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Citric acid is good reducing agent for gold nanoparticle preparation.
It's mild, controllable reducing agent which allows the synthesis under room temperature.
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White Yeti
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I'm surprised no one showed up at your door to ask what you were going to use that citric acid for.
Citric acid is used to catalyse the peroxidation of acetone. As you may know, acetone peroxide is a high explosive, used by terrorists to blow things
up. So whatever you do, do not buy any acetone or peroxide because then they will definitely show up at your door.
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ScienceSquirrel
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Quote: Originally posted by White Yeti  | I'm surprised no one showed up at your door to ask what you were going to use that citric acid for.
Citric acid is used to catalyse the peroxidation of acetone. As you may know, acetone peroxide is a high explosive, used by terrorists to blow things
up. So whatever you do, do not buy any acetone or peroxide because then they will definitely show up at your door. |
Citric acid is sold by the kilogram for making bath fizzies. Acetone can be bought by the litre at your local fibreglass shop and 30% hydrogen
peroxide is at your local health shop.
All three compounds have legitimate common large scale uses so banning or controlling them is not very likely or possible and as for tracking
purchases the police would do nothing else if they had to watch them.
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Random
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As for my citrazinic experiment, nothing was accomplished.
The dark brown sticky mass didn't evaporate, it just smelled somewhat bad.
Flourescence wasn't observed, it was hard to dillute it with water, not too soluble.
On the outside it was loking green, but inside the test tube was all dark brown. Not sure if I cooked it too much with the candle. Basically, it's
harder to make it than it sounds. The compound didn't have those properties described by the paper provided here at all. Further reactions just didn't
happen. Something tells me it was just burnt citric acid.
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Random
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2nd experiment
put 2x urea as much as citric acid
heated it for only short time
got gellatinous yellow transparent solid at the bottom
dissolved it in water
separated into 2 test tubes
added vinegar into one and NaHCO3 into another
no precipitate was seen 
i am starting to think that its all bullshit what is written there Did anyone
made any citrazinic acid? I mean precipitated it from solution?
Because I can't seem to precipitate anything at all.
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Nicodem
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| Quote: Originally posted by Random | | i am starting to think that its all bullshit what is written there Did anyone
made any citrazinic acid? |
You think something is bullshit after you made no effort to reproduce it?
There are several authors describing the procedures for preparing citrazinic acid and yet you ask if anyone made any? At least have some respect for
their work, even when for whatever reason you don't want to follow the procedures they developed.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Random
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| Quote: Originally posted by Nicodem | | Quote: Originally posted by Random | | i am starting to think that its all bullshit what is written there Did anyone
made any citrazinic acid? |
You think something is bullshit after you made no effort to reproduce it?
There are several authors describing the procedures for preparing citrazinic acid and yet you ask if anyone made any? At least have some respect for
their work, even when for whatever reason you don't want to follow the procedures they developed. |
Sorry I was just dissapointed in results as I tried this experiment more than once...
I will try it again in more controlled conditions.
By the way, this is the picture of citrazinic acid I found on the internet:
This is the colour I obtained, but as a gellatinous solid. SO either I was pretty close, obtained too small amount of acid to be isolated or
gellatinous solid was just decomposed citric acid along with very small amount of citrazinic acid.
What I can say that last time I heated it for way too long time and I obtained black tar which I thought It was citrazinic acid.
If I manage to make it, I will gladly post the pictures.
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aliced25
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Check this paper out, then look at what you are doing.
| Quote: | In
order to satisfy ourselves as to whether citramic derivatives would condense under similar circumstances, we heated (a) citramide and (b) the mixture
of citramic acids which is left as mother liquor in the preparation of citramide, each with ammonia, of 0.880 at 120-130".
In each case, a good yield of citrazinic acid was obtained ; the absence of citrazinamide, which might have been expected to be produced, is indicated
by the analyses :-
(a.) 0.1146 gram of substance gave 9.6 C.C. N at 759 mm. and 21".
(p.) 0.1611 ,, 79 12.7 ,, 759 ,, 19.5".
Calculated for Pound.
C6H5N04. (a*> (P.)
N .. .. .. .... 9-03 9.5 9.08
Similarly, methyl citrate was found to yield citrazinic acid when heated with ammonia in a sealed tube ; the yield was 33 per cent. of the citric salt
taken. |
LXXXIV.—Anhydro-derivatives of citric and aconitic acids
T. H. Easterfield and W. J. Sell
J. Chem. Soc., Trans., 1892,61, 1003-1012
DOI: 10.1039/CT8926101003
But if methyl citrate heated with ammonia gives citrazinic acid, then the anhydride/acid chlorides are presumably overkill. Try boric acid, ammonia
and the acid (http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v81...).
The paper is attached on an earlier page of this thread. I also read that in MW processing of polymeric gel precursors, they try to keep the ethylene
glycol/citric acid temp below about 170C as the citric acid dehydrates to aconitic acid and precipitates. Could be useful.
[Edited on 28-4-2013 by aliced25]
From a Knight of the Realm: "Animated movies are not just for kids, they're also for adults who do a lot of drugs." Sir Paul McCartney
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Fantasma4500
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well it can be used to make sucrose into glucose (glucose-glucose)
more sirupish
i guess this is good for rocketfuel as you often add abit of sirup to it
i did this by heating about... what.. 50g with 0.1g citric acid and abit of water in a beaker
think the actual ratio is ~450g to 1g citric acid
it will become golden and slurry ish, so apart from that it tastes good there is actual energetic uses of this and probably a few for chemistry
purposes, but probably not many you couldnt use normal sugar for
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aliced25
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According to this article (http://pubs.rsc.org/en/content/articlelanding/1913/an/an9133...), oxidize it to acetonedicarboxylic acid with permanganate. That acid isn't stable
it needs to be esterified, preferably with methanol (it might come in handy someday). Interestingly, that isn't the only reference I've seen to
Acetonedicarboxylic acid being made with permanganate - despite the usual preparation requiring fuming H2SO4 (http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1...) - the simpler, OTC route seems to have been ignored.
Or react it with bromine water to form pentabromoacetone (http://www.jbc.org/content/113/1/235.full.pdf+html?sid=1ea03... or this one http://www.jbc.org/content/156/1/33.full.pdf), I'd suggest by pretty much the same mechanism as it forms pentachloroacetone (as suggested
up-thread):
| Quote: | On Stahre's Reaction for Citric Acid. A. Wohlk. (Zeit. anal. them., 1902, xli., 77-100.)-The sensitive reaction for citric acid discovered by Stahre
(Nordisk Farm. Tidsskrift, 1895, ii., 141) is based upon the fact that on oxidizing citric acid with potassium permanganate and adding bromine a white
precipitate insoluble in ether is obtained. Stahre concluded that in this reaction the citric acid was oxidized to acetone, which was converted by the
bromine into a bromacetone.
In applying the test when less than 5 milligrammes of citric acid are present, the acid is dissolved in 2 C.C. of water, and heated to 30" C. after
the addition of 2 to 4 drops of & permanganate solution. If any slight precipitation of manganese peroxide occur, 1 or 2 drops of a, 4 per cent.
solution of ammonium oxalate and about 1 C.C. of 10 per cent. sulphuric acid are introduced to clear the liquid. On now adding 2 drops of bromine
water a distinct turbidity is produced.
When more than 5 milligrammes of citric acid are present the solution in 2 C.C. of water is treated with 5 drops of the permanganate solution, heated
to 30" to 40" C., cooled, and mixed with 1 C.C. of dilute sulphuric acid. Should any precipitate be formed it can be removed by the addition of a
little ammonium oxalate. Bromine water then added drop by drop gives a precipitate of extremely fine needles of pentabromacetone.
Stahre's reaction is obtained not only with pure solutions of citric acid and its salts, but also in the presence of other organic acids precipitated
by calcium, such as tartaric, oxalic, malic acids, or inorganic acids, such as sulphuric and phosphoric acids. In such cases, however, more
permanganate must be used, and it is best to make the test on a hot solution. Organic acids that react with bromine must obviously be removed.
The author confirms the statements of Henkel, Scheibe, and others as to the presence of citric acid as a normal constituent of milk, He has separated
a compound which he has identified as citric acid by Stahre's reaction and other tests. (The Analyst, 1902, vol.27, pp.196-197: http://lib3.dss.go.th/fulltext/Journal/analyst/Analyst1901-1...) |
Those olden day chemists - inventive bastards really, see what comes of not having consistent lab supplies? Pretty much what we have to deal with
actually. Good to know that the reaction is named, Stahre's Reaction, well there you go
[Edited on 25-5-2013 by aliced25]
From a Knight of the Realm: "Animated movies are not just for kids, they're also for adults who do a lot of drugs." Sir Paul McCartney
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