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Author: Subject: Picric Acid and the Mystery of the Red Goo
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Picric Acid and the Mystery of the Red Goo

Today I attempted to prepare picric acid. I used non-purified aspirin tablets. Each contained 0.325g of acetylsalicylic acid. Each also contained 0.025g of starch and dicalcium phosphate.

I warmed 125mL of 94% H2SO4 in a beaker to 60C, and added 88 aspirin tablets. I then began to add about 2g of NaNO3 per minute, stirring rapidly the entire time. I added a total of 51g of NaNO3. A few minutes after the addition of the final scoop of NaNO3, I let the contents of the beaker to cool down to 40C. There was a reddish foam in the beaker. I dumped the contents of the beaker into 300mL of cold water. Some picric acid precipitated, but when the red foam was stirred, it formed a glob of red goo. This "goo" was not water soluble, and had no attraction for glass. When removed and placed in a separate beaker, and then squeezing out the air bubbles, it slowly became a foam again! I'm wondering what the hell that stuff is. Any ideas?

(edited to add) It's not just a small amount of red "goo"; there's probably around 10g. It boils before igniting; it burns gently, and not easily. It leaves a lot of carbon when burned.

I weep at the sight of flaming acetic anhydride.
plasma
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Maybe the binder got polymerized and burns becuse the starch got nitrated ? (Or maybe not)

BTW, Why didn't you purify the tablets before making the picric acid
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Well, a total of 2.2g of binder - the binder being composed of starch and dicalcium phosphate - shouldn't have such a catastrophic effect on the reaction.

By the way, I'm hearing that others have also gotten the red "goo" from using a method similar to mine (mine was based off of Mr Cool's method). I hear also that some have gotten the red "goo" from using too much potassium/sodium nitrate.

I weep at the sight of flaming acetic anhydride.
plasma
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Maybe you will have more luck with the synthesis at Powerlabs
http://www.powerlabs.org/chemlabs/picric.htm
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I also got the Red Goo!!! i have gotten it with Mr. Cool's method and the method in KIPE1. i think they may be the same if not realy similar methods. also, the TNP that i did get was realy dark red brownish in both cases. i think ill chuck it.

in fact, the method that i had the best luck with so far was mega's, i used 10 asprin 70ml H2SO4 and 9g KNO3. i got a kinda good yield. i htink i also did this with 50ml of H2SO4, i cant remeber witch got the best yield though. one was about 4-5g the other was like 1g. i will use his mrthod next.

edit: oh yeah, when i did Mr Cool's procedure i pureified the asprin and i still got this crap.

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i am halfway through megas method, i adjusted it a bit so it uses 500ml H2SO4 instead of 700. but im just doing a 10 asprin test batch so im using 50ml.

i used 9g NaNO3

it looks REALY good. after i nitrated it it lookes yellow/red as opose to black which is GOOD. i am letting it cool. i will precipitate in a couple minutes and let you know how it goes.

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BrAiNFeVeR
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I'm really interested in this HE too, so I'll join the experiments. for now I'll follow madog's suggested method, but if you want a second opinion on an other method, I might just try that one too :-)
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sorry

im sorry but i negleted to tell u how it whent. it whent SHIT!!

i got a tiny bit of crap!

i think ALEN's method may be good...

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BrAiNFeVeR
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Well, it certainly did not went "shit" with me !!

I used:
- 5 grams of ASA (10 purified 500 mg aspirine tablets)
- 70 ml H2SO4
- 10 grams of KNO3

The reason I used 10 grams of KNO3 is because mega's method stated I should use 90 grams of NaNO3 OR KNO3 (thus making no diffirence between them) while NaNO3 has a considerable higher amount of the nitrate group per weight then KNO3.
I couldn't be bothered to calculate the correct amount of KNO3, so I rounded it of to 10 grams.

I'll post yields when product is dried, but I can say it looks good

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Nils
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TNP?

the red stuff is proboubly DNP(Dinitrophenol or even Mononitrophenol).

By the way, my TNP was yellow, but yesterday i've tried it again(for making DDNP, with succes! Very good primair) and it was Yellow! But after boiling it in water it becomed Yellow(let the water evaporize as it is very soluble in it)

anyway, it tooked a few times until my TNP worked. Just try again, and try again.....

By the way, i'm mr.evil from teh E&W forum(NO i'm not banned)

BrAiNFeVeR
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I finally got around to purifying and drying my TNP.

Since the filter paper that it was drying on was starting to decompose, I lost a cosiderable amount of TNP I think.

What I heve left now is a bit more then 3 grams, wich is no great yield at all.

But I will try again, and optimise yields as much as I can this time !!
Also, on this occasion, I didn't see any of the mistery red goo.

So I'll try the use exact same method

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I think that the Red Shit is actually picric acid anhydride. That would explain all of its properties - it's being insoluble in water, its tendency to slowly form picric acid when in contact with water, its waxy/gooey nature, everything...

I weep at the sight of flaming acetic anhydride.
kingspaz
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have you tried detonating the goo? if it detonates then atleast you know its a nitrated compound.
Nils
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No i didn't tried to detonate it, but it won't even burn! Next time when i'm making TNP i will use Phenol(as i have 300grams of it 8)

btw, don't get any phenol compounds on your hands, it will be yellow for days. Not to speak about the TNP toxicity.

-Nils
kingspaz
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nils, TNP is toxic but its not THAT toxic. i thought the most of the toxicity is casued by the phenol group. i also remember reading the LD50 was 2g but i could be wrong about that.
kingspaz
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dammit, why can't i edit my posts?
also if it doesn't burn then its not a nitrated compound.
Polverone
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I'm not sure why people can't edit their posts. Even moderators can't. If I want to edit something I have to change the database entries by hand. My conclusion is that "something is screwed up" but I don't want to switch or reinstall software because we've done that too much already. Sorry, I know it's a pain.
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today i did brainfevers method useing 10grams of unpureified asprin powder(i dont think its worth pureifying) 20grams of NaNO3(what was lyeing around) 140ml 935 H2SO4. i also heated the ASA/H2SO4 to disolve it easier and after it was mostly disolved i took it off. then i waited a little while to let it convert to phenol and cool a bit. then i added the NaNO3 in 4 parts. the whole process and cleanup took around 37 minutes, not bad

it worked GREAT! the TNP looks SUPER pure and the yeild is good! i will wigh it when dry.

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PHILOU Zrealone
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I already answered the red picric acid question elsewere in this forum!

By the way you may end with mononitrophenol and dinitrophenol too if the nitratation is not efficient enough (enough HNO3/H2SO4 at a strong enough conc).
DNP is explosive too and also makes explosives primary heavy metal salts; they are just less powerful than TNP and TNP salts!

I can tell because I have pure paranitrophenol (4nitrophenol) and (2,4 dinitrophenol) and TNP (2,4,6) that they all looks the same!
Cristalline yellow, colourising everything in yellow!

PH Z
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I just carried out a pretty poorly executed experiment, but it may prove to have interesting results. I dumped 26g of acetylsalicylic acid into 50mL of mixed acid (it had absorbed a little moisture from the air). I stirred it, and kept the temperature below 30C for two hours. Intensely violet crystals were on the sides of the beaker. I then dumped in 200mL of ice water. A huge amount of a purplish-brown precipitate formed. I'm wondering if that is something like a nitrosalicylic acid - the acetate group on acetylsalicylic acid should have no trouble being removed (addition evidence for that case: I smelled a substantial quantity of acetic acid).

I weep at the sight of flaming acetic anhydride.
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I cooled down the sludge to 6C, and filtered it. Here's a photo.

I weep at the sight of flaming acetic anhydride.
BLAST_X
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2,4,6-tnp

Here some attributes to picric acid.

- good density, ~ 1,8 g/ml
- high vod, ~ 7400 m/s
- high yield with all different synthesis-methods

- small volume of gas, ~ 345 ml/g
- chemicals to synthesizing picric acid
are expensive (phenol, benzene)
- tnp are toxic (can be resorbed by skin)
- high dissolubility in H2O
- somewhat sensitive to friction, heat and shock

I think,
picric acid is a better smoker-powder when not purify correctly or produced
by H2SO4/KNO3-method.

all you need is C - H - O - N
BLAST_X
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In a pollutes condition its a better flash propellant. Produced by H2SO4/KNO3-method, the product have a very bad quality than produced by Phenol.
On the open air, 2,4,6-tnp burns only with high temperature when it lighted.
It can be detonated when strongly heated at high density or under pressure
without the presence of O2.
With a vod of ~ 7400 m/s, 2,4,6-tnp can be used as a second primary explosive in a detonater to set off insensitive high secondary explosives or in a blasting cap ignited by a primary explosive.
2,4,6-tnp have a high reactivity with many other chemicals. Therefore, its sometimes dangerous when 2,4,6-tnp form picrates by reacting with metals ...
It can be used to synthesize other less dangerous explosives.
(ammonium picrate)
2,4,6-tnp are used in labs too,
to synthesize many substances or other benzene-compounds.

all you need is C - H - O - N
BLAST_X
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I mean smoke-powder.
With 2,4,6-tnp in this cleanliness, you can
create more smoke than other more.
I suppose, picric acid can be easy synthesized with salicylic acid by a 3-step reaction in one, by adding SA to a mixture of H2SO4/HNO3 and heating for a few hours.
I need looking for, to say the correct synthesis-way !

all you need is C - H - O - N
Loony
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