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Author: Subject: Picric Acid and the Mystery of the Red Goo
Polverone
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[*] posted on 28-10-2002 at 17:22


Loudest explosion per gram is quite a variable concept. Per gram of unconfined material? Per gram in thick cardboard tubing? Actual highest output of acoustic energy, or perceived loudest? After all, high explosives make a high "crack" that often seems less loud than the lower "boom" of pyrotechnic materials.

In other words, I doubt there are any hard and fast numbers for this sort of thing. You might as well ask which pyrotechnic formula is the most beautiful per gram.

Oh, and just FYI, if you're interested in discussing activities likely to bring concerned neighbors and/or agents of the law to your home, sciencemadness.org isn't the place to do it. This isn't Fingerless McPhee's Mad Bomber Knowledge Emporium.
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[*] posted on 30-10-2002 at 06:07


Apologies if I am trangressing forum rules. I am new. No bad intentions or desire to upset neighbours. It was an experiment carried out at school and was surprisingly loud in adjacent classrooms. The material was unconfined on a shallow metal dish.
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Polverone
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[*] posted on 30-10-2002 at 09:13


No harm done. I just got the unfortunate first impression that you might not have very much regard for safety and responsibility. If this was a classroom demonstration, no problem.
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cool.gif posted on 5-3-2003 at 03:36


Picric acid can be made from any aromatic compound! If you are a good organochemist, have good synthesis pathway skills and common sense!

Benzen is expensive and phenol too!

Use vanilin from artificial flavoured suggar!
(HO)C6H4(-CH=O); no mather where the aldehyd group is in mixed acid it will oxydises and leave as CO2 upon heating!

Use toluen or xylen from synthetic lounge!
Mix with diluted KMnO4 to oxydise lateral alkylic chains; then add HCl and collect the unsoluble benzenic acids and diacids with ether or alcohol;dry the acids after evaporation of solvant; then add to 70% HNO3 and boil under reflux to get mononitrocompound and CO2 evolution; you should have nitrobenzene! Reduce with Fe/HCl or Sn/HCl or (NH4)2S to get aniline, diazotate it with NaNO2 (one without isolation from the previous batch and boil under reflux in ethanol...to get phenol!

Use paradichlorobenzen (used in pipirooms to give it a fresh smell or as antimoth)
Cl-C6H4-Cl + HNO3 -reflux and boil-> 1,4 dichloro 2 nitrobenzene!
Isolate and make it boil under reflux in saturated NaOH solution to get 4chloro2nitrophenol and 2nitropararesorcinol!
The 2nitropararesorcino might be obtained immediately by fusing the dichloronitrocompound in solid NaOH!

This later compound is interesting since:
HO-C6H3(NO2)-OH -HNO3/H2SO4->
O=C(C(NO2)=C(NO2))2C=O
and
HO-C6(NO2)4-OH
Both powerfull sensitive HE (over the TNP)!




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sad.gif posted on 5-3-2003 at 03:41


PbO2 is a form of Pb(4+)!
PbO2 + 4HO-C6H2(NO2)3 --> Pb(O-C6H2(NO2)3)4 + 2H2O

No doubt the salt exploded while heated!
The picrates must be done under no heating conditions by methathesis!
Na, K or NH4 picrates saturated solutions are allowed to react with concentrated nitrate salt of the desired compound!

Pb(NO3)2 + Na/K/NH4 picrate --> Pb(II) picrate precipitate + Na/K/NH4 nitrate!
Wash with clear water!
Never recristallise...you would get bigger cristalls if you are not experienced...thus stress in growing cristalls might induce detonation!




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[*] posted on 7-4-2003 at 13:00


About the red goo, I found something interesting.

NO2 groups seem to color a substance red when they are connected through an oxygen atom instead of the usual nitrogen atom.




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smile.gif posted on 10-4-2003 at 05:10


QUote:
"posted on 9-9-2002 at 23:31
I already answered the red picric acid question elsewere in this forum!"

Answer is nitronic acid rearangement!

CH3-C(OH)=C(CH3)-NO2 <--> CH3-CO-CH(CH3)-NO2
CH3-CO-CH(CH3)-NO2 <-OH(-)-> CH3-CO-C(CH3)=N(O)-OH
Thus beta nitro enols undergo enol-ceton equilibrium to provide a alfa hydrogenated nitro derivative in tiny % that gives the yellow colour; the later upon the action of a base undergo the nitronic rearangement
cf NM:
CH3-NO2 + NaOH --> CH2-NO2(-) + Na(+) --> CH2=N(O)-ONa
The later compound is deep orange to deep red-brown!

:cool:




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[*] posted on 7-8-2003 at 05:24


i found this method of making picric acid : 2 grams ASA , 10 ml H2SO4 and 4 grams of KNO3 . is this method OK ???? i didn't made large amounts. i did just how it said in the procedure . it was ok , but i don't know about the yield ... i did some search on the net and found that the theoretical yield should be 80% . my TNP is still in ice water . today i'm going't to let it outside to dry out . i was meaning to put TNP in a small plastic bag so that it doesn't form picrates and than in a film carnister and then a electric detonator ... maybe this could be the safest detonation , what about the storage . i searched and i found that the safest method is to disolve it in water and so to store . is this all ok ? thanks ! :cool:
here is a picture of TNP in ice water after the procedure ::

Image85.bmp - 297kB
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[*] posted on 8-8-2003 at 04:34


I think I read somewhere that the incorrect making of TNP results in the formation of polynitrophenol compounds, with no specific composition, which then forms the alleged red goo.... try it, it burns!
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[*] posted on 21-1-2004 at 06:02
Picric acid (TNP) & AN


Instead of making a new topic, it would probably be best to post here in this old topic. I was wondering, given TNPs high VOD and good brisance could it be a good choice for something to be mixed with powdered/dried AN in charges weighing under 1 pound and with a ratio of about 2:1 AN:TNP. I guess my question is is there any chance that TNP could react to the AN in a bad way? NG and almost all other nitrates behave fine and are used frequently with AN as a sensitizer but I never hear much about TNP/AN.
PTN used to be used as a commercial booster for many years and commercial boosters are up to 1lb in weight so I would imagin it to be safe.

[Edited on 21-1-2004 by IgnorantlyIntelligent]

[Edited on 21-1-2004 by IgnorantlyIntelligent]




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[*] posted on 21-1-2004 at 12:12


If I were going to try making picric acid from asprin, I'd first isolate pure salicylic acid (dil. NaOH, filtration, alkaline hydrolysis, reacidification, filtration, recrystallization). Then perform a nitration of pure salicylic acid following a tested recipe. There a variety of binders that might be in the tablet, and nitration of the mixture will make it much harder to get a pure product in decent yield. (The red glop people are getting probably has at least half-a-dozen different reaction products in it.)
Pure picric acid is a nice yellow crystalline material that's not a great explosive in itself. Picrate salts are easily prepared since picric acid is a pretty strong acid.
Pure products require pure starting materials.
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[*] posted on 21-1-2004 at 12:27


Most people do purify their aspirin tablets to isolate crystalline material first. Hot acetone works great, though it's hard to finish the filtration before crystallization takes over if you're trying to gravity filter. When I nitrated acetylsalicylic acid isolated in this fashion, using sulfuric acid and potassium nitrate, I was able to recover beautiful canary-yellow crystals that stained everything they touched, formed salts with alkali carbonates with evolution of CO2, and otherwise behaved as I would expect picric acid to. I never saw any "red goo." However, I didn't have a pure reference sample of TNP to compare with, and it's quite possible that I had lower-nitrated phenols in there also. It would interesting to repeat this experiment and run TLC on the product.

Madscientist was of course just begging for trouble by not bothering to purify his starting materials at all.
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[*] posted on 21-1-2004 at 12:57


Quote:
Originally posted by Polverone
Most people do purify their aspirin tablets to isolate crystalline material first. Hot acetone works great, though it's hard to finish the filtration before crystallization takes over if you're trying to gravity filter. When I nitrated acetylsalicylic acid isolated in this fashion, using sulfuric acid and potassium nitrate, I was able to recover beautiful canary-yellow crystals that stained everything they touched, formed salts with alkali carbonates with evolution of CO2, and otherwise behaved as I would expect picric acid to. I never saw any "red goo." However, I didn't have a pure reference sample of TNP to compare with, and it's quite possible that I had lower-nitrated phenols in there also. It would interesting to repeat this experiment and run TLC on the product.

That all sounds spot-on! Why can't more people be like you?:cool:
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[*] posted on 21-1-2004 at 14:33


Picric and AN mixed would probably for some Ammonium Picrate. This would ad to the mixture's sensitivity, but most likely not enough to make it extremely dangerously sensitive or anything. It might even come in handy if you theoretically decide to test the mix out.

I also don't know how strong of a base(or if it even is one at all) AN is. IMO some Ammonium Picrate would form regardless.
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[*] posted on 22-1-2004 at 11:06


Reaction time/heating

I am not familiar with all the syntheses people refer to in all their detail, but it seems to me that people do not heat for very long periods, if any at all, inyour procedures for TNP, if i remeber correctly in 'advanced practical organic chemistry' for example the procudure call for the phenol (/phenol derivative) to be heated with the sulphuric acid to fully form phenol sulphonic acid before introduction of the nitrate (be it HNO3, XNO3 etc). The synthesis i'm refering too also calling for the reaction to be held at around 100C for 1 1/2 hours for the reaction to complete fully. Possibly you are all aware of this and know of a reason why it is unecessary, but as many of you refer to disapointing yeilds, this may be a contributing factor.

I have not carried out this synthesis for a while and do not remember and specifics of results, but i may attempt it soon and will be sure to post information here that could be useful.

pete
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[*] posted on 22-1-2004 at 12:46


Have some of you tried to make Picric Acid from different chemicals (instead of ASA/SSA) such as silk ?
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[*] posted on 22-1-2004 at 12:57


Rofl :)
Silk is protein. The only amino acids that have somethng that resembles a phenol group is phenylalanine and tyrosine. So the yield is definitely not going to be high, only 2 out of 20 amino acids. First destruction of peptide bonds with HCl at high temp for several hours, then, possibly destructive sulphonication. Maybe you have some luck there... maybe ;)
A better one is indigo, a dye that you can get freely. I think with NaOH (I once did it a long time ago) you get sodiumphenolate...




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[*] posted on 24-1-2004 at 02:07


"other early experimenters obtained picric acid by nitrating various substances such as silk, natural resin, etc ..." They also talk about wool or horn and indigo.

That's written in J. Akhavan's chemistry of explosives.

So I was wondering if somebody tried it
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[*] posted on 25-1-2004 at 02:58
A brief OT about EBW dets


I have recently gotten some promising results with my explosive bridge wire detonator and after reading a lot of accident reports I want to study high explosives without the danger of organic peroxide detonators. Most people I see use Manitol Hexanitrate or PETN in their EBW caps, unfortunately these synthetic sugars are hard to get, Asprin or Oil of Wintergreen seem like a better bet.

My question is that could I use straight TNP or one of it's alkali metal derivatives in an EBW cap, I have not found much on the impact energy in Joules needed to innitiate them so any info you would have would be a great help.




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[*] posted on 25-1-2004 at 14:03


potassium picrate
http://www.powerlabs.org/chemlabs/potassium_picrate.htm

I believe that it is more sensitive than picric acid, however it doesent seem to be easily detonated.

[Edited on 25-1-2004 by rogue chemist]
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[*] posted on 30-1-2004 at 14:00


<blockquote>quote:<hr>Picric and AN mixed would probably for some Ammonium Picrate. This would ad to the mixture's sensitivity, but most likely not enough to make it extremely dangerously sensitive or anything<hr></blockquote>
no nitric is a hell lot more acidic than picric acid. plus the specific character of ammonium picrate is its high <b>in</b>sensitivity




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[*] posted on 28-3-2004 at 18:54


I was under the impression that ammonium picrate was an insensitive energetic compound. Thats what it says in megalomania's chemlab. Also NH4NO3 does not have a lower ph level than picric acid, I have found that NH4NO3 when you add NH4NO3 to a ph tester it hardly changes the color. Not to say that I would want to store NH4NO3 in a metal container for long periods of time.
EDIT: oh duh kaboom said it was insensitive.
[Edited on 29-3-2004 by tom haggen]

[Edited on 29-3-2004 by tom haggen]




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[*] posted on 18-4-2004 at 05:12


If your trying to make picric acid, I think a good way would be to start with p-cresol or beta-nitrostyrene. Use hydroxylamine to put on some NH2 groups and oxidize it with caro's acid. If that doesnt work, soak it in nitric acid. It's not picric acid, but it might be worth trying...

PS: The oxygen that links the two major rings in sucrose can be oxidized to peroxide. Once youve done that, Thake advantage of all the hydroxyl groups. Pump it up with nitric acid!!!
Its really worth it!:D




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[*] posted on 21-7-2005 at 22:46


Quote:
Originally posted by halogen
PS: The oxygen that links the two major rings in sucrose can be oxidized to peroxide. Once youve done that, Thake advantage of all the hydroxyl groups. Pump it up with nitric acid!!!
Its really worth it!:D

Can anyone confirm this? Have you tried it? How would you go about this oxidation without burning up the sucrose?




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[*] posted on 9-5-2008 at 11:01


I was wondering if it is possible to make picric acid via sulfuric acid and ammonium nitrate instead of potassium nitrate. I remember reading about it on roguesci a while back but the forums are currently undergoing maintenance and i can't seem to find any information elsewhere.

thanks for the time!




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