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Author: Subject: Picric acid: different instructions
grndpndr
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Theoretically If it did take 10x approx 1/4gram to reach full detonation that would = approx 2.5grams.IIRC approx 2.8 gr fills 1ml3 @ its highest density/vod. that doesnt amount to much volume in a .25 ID cap
given PB picrates density.Ballpark IIRC thats about a 1 3/4 in long cap with 1 gram PA also pressed to its optimum density.

Forgive my stubborness but I think that how edison maDE his breakthroughs.Im not claiming to be an edison simply possesing a stubborn streak.No offense!
hiperion42
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Attachment discusses the mix of picric acid with litharge for use as a initiator capable of detonating the nitrated phenol.

.....ejuu....................................................................Ffg..............................g.............
Blasty
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 Quote: Originally posted by hiperion42 Attachment discusses the mix of picric acid with litharge for use as a initiator capable of detonating the nitrated phenol.

Is there a continuation to that interesting paper? It seems the author was planning more tests of the improvised detonator, and whether or not it could be used with ammonium nitrate and oxidizer-fuel explosives.
quicksilver
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One of the difficulty in commercial study papers of this type (Remington Arms Corp submitted for Gov't review) is that occasionally they are offshoots of accidents or studies of "concept methods". Picric acid had been subject to periodic tragedies via the (accidental) emergence of picric - metal salts in storage conditions. However when submitted, expressions such as "squib" are often used to describe items that have a direct bearing on the utility and efficiency of the technique. The reader then does not fully know what was the composition of the initiator.

Truly high quality Picric acid would initiate with the basically same circumstances as many other benzene-ring nitrated materials. In fact TNP is one of the more sensitive of that group and equivalent of the "standard #6" fuse cap: compressed mercury fulminate would substantially fill the need. Because we don't know what is meant by "squib" when used to describe the initiation of the possible lead picrate; we might even have a minor explosive charge in train. These unknowns put us at a disadvantage for evaluation.

The WiZard is In
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 Quote: Originally posted by Blasty Is there a continuation to that interesting paper? It seems the author was planning more tests of the improvised detonator, and whether or not it could be used with ammonium nitrate and oxidizer-fuel explosives.

I did a Vulcan Mind Meld with la Net, and yes, however, only the July report can be DL'd gratis. The others
can be had from the NTIS. [$] 1. Title: DEVELOPMENT OF EXPLOSIVES AND INITIATORS FOR SPECIAL OPERATIONS Personal Author: Johnson, Theodore B Corporate Author: REMINGTON ARMS CO INC BRIDGEPORT CT Source Code: 301600 Page Count: 8 page(s) AD Number: AD0410390 Report Date: 01 MAY 1963 Distribution Code: 01 - APPROVED FOR PUBLIC RELEASE Report Classification: U - Unclassified Collection: Technical Reports Title: DEVELOPMENT OF EXPLOSIVES AND INITIATORS FOR SPECIAL OPERATIONS. Personal Author: Johnson,Theodore B Corporate Author: REMINGTON ARMS CO INC BRIDGEPORT CONN Source Code: 301600 Page Count: 1 page(s) AD Number: AD0416303 Report Date: 10 JUL 1963 Distribution Code: 01 - APPROVED FOR PUBLIC RELEASE Report Classification: U - Unclassified Collection: Technical Reports Title: DEVELOPMENT OF EXPLOSIVES AND INITIATORS FOR SPECIAL WARFARE OPERATION... Personal Author: Johnson,Theodore B Corporate Author: REMINGTON ARMS CO INC BRIDGEPORT CONN Source Code: 301600 Page Count: 3 page(s) AD Number: AD0425772 Report Date: 01 SEP 1963 Distribution Code: 01 - APPROVED FOR PUBLIC RELEASE Report Classification: U - Unclassified Collection: Technical Reports Title: DEVELOPMENT OF EXPLOSIVES AND INITIATORS FOR SPECIAL OPERATIONS Personal Author: Johnson, Theodore B Corporate Author: REMINGTON ARMS CO INC BRIDGEPORT CT Source Code: 301600 Page Count: 6 page(s) AD Number: AD0425771 Report Date: 31 AUG 1963 Distribution Code: 01 - APPROVED FOR PUBLIC RELEASE Report Classification: U - Unclassified Collection: Technical Reports Title: DEVELOPMENT OF EXPLOSIVES AND INITIATORS FOR SPECIAL WARFARE OPERATION... Personal Author: Kenney,J F Johnson,Theodore B Corporate Author: REMINGTON ARMS CO INC BRIDGEPORT CONN Source Code: 301600 Page Count: 3 page(s) AD Number: AD0425773 Report Date: 01 OCT 1963 Distribution Code: 01 - APPROVED FOR PUBLIC RELEASE Report Classification: U - Unclassified Collection: Technical Reports Title: DEVELOPMENT OF EXPLOSIVES AND INITIATORS FOR SPECIAL OPERATIONS. Personal Author: Johnson,Theodore B Corporate Author: REMINGTON ARMS CO INC BRIDGEPORT CONN Source Code: 301600 Page Count: 2 page(s) AD Number: AD0416302 Report Date: 01 JUN 1963 Distribution Code: 01 - APPROVED FOR PUBLIC RELEASE Report Classification: U - Unclassified Collection: Technical Reports --------- Dr. Dupre [1889] made the interesting observation that a mixture of two parts by weight litharge (oxide of lead) with one part picric acid detonates violently when heated. I will heat one grain of this mixture on this piece of tin-plate, and this quantity will be sufficient to give a very sharp explosion. http://tinyurl.com/3sc5fb8 The WiZard is In International Hazard Posts: 1617 Registered: 3-4-2010 Member Is Offline Quote: Originally posted by Blasty  Quote: Originally posted by hiperion42 Attachment discusses the mix of picric acid with litharge for use as a initiator capable of detonating the nitrated phenol. Is there a continuation to that interesting paper? It seems the author was planning more tests of the improvised detonator, and whether or not it could be used with ammonium nitrate and oxidizer-fuel explosives. Well ... the small arms cartridge case detonator made it into the Low Albedo Book(s), however, use litharge and PA in it did not. Blasty Hazard to Others Posts: 108 Registered: 25-7-2008 Member Is Offline  Quote: Originally posted by The WiZard is In Well ... the small arms cartridge case detonator made it into the Low Albedo Book(s), however, use litharge and PA in it did not. It seems the author of those reports was working along these lines, noticed at least as far back as the 1890s: "A very crude admixture of metallic oxides or nitrates, notably litharge, lime, and the nitrates of lead, and strontium, with picric acid, will, on the application of heat, detonate, and such detonation will extend to contiguous masses of the unmixed acid. The heat first induces the formation of picrates, and its continued application causes their detonation." http://books.google.com/books?id=_4lBAAAAIAAJ&pg=PR38&dq=lit... It would be interesting to read what explosives he managed to successfully detonate with these litharge-picric acid mixtures + pure picric acid booster. [Edited on 13-4-2011 by Blasty] quicksilver Super Moderator Posts: 1820 Registered: 7-9-2005 Location: Inches from the keyboard.... Member Is Offline Mood: ~-=SWINGS=-~ Some elements of this issue rest in the level of efficiency of the stated primary. A great many things can eventually develop a detonation wave (or energy transmission in general) strong enough to transmit energy from primary to secondary. The contingency is amount (weight/volume) of the primary in question. Use enough of many materials and you could develop a train of enough energy to initiate the secondary; the question is how much is enough? Additionally, is this the best or appropriate example of method(s)? What's more if we examine a simplistic technique to synthesize a salt it may not necessarily be the most effective example of that salt. A very good example is lead picrate. Carefully synthesized basic lead picrate is decidedly more efficient than poorly or haphazardly made normal lead pirate, etc. Blasty Hazard to Others Posts: 108 Registered: 25-7-2008 Member Is Offline  Quote: Originally posted by quicksilver Some elements of this issue rest in the level of efficiency of the stated primary. A great many things can eventually develop a detonation wave (or energy transmission in general) strong enough to transmit energy from primary to secondary. The contingency is amount (weight/volume) of the primary in question. Use enough of many materials and you could develop a train of enough energy to initiate the secondary; the question is how much is enough? Additionally, is this the best or appropriate example of method(s)? What's more if we examine a simplistic technique to synthesize a salt it may not necessarily be the most effective example of that salt. A very good example is lead picrate. Carefully synthesized basic lead picrate is decidedly more efficient than poorly or haphazardly made normal lead pirate, etc. There's several things to consider as to why the author of those reports is choosing these methods. He seems to have been interested in improvising detonators + explosive charges from relatively common & available materials and without requiring too complicated processes or apparati (a kind of "MacGyver" thing.) Also, it seems from the descriptions of these picric acid + litharge/lime/nitrate mixtures that they only mention their explosion with heat, apparently not with friction or impact, or at least not easily enough to make a pertinent note of it. Since the picrates do not seem to form until heat is applied to such mixtures, this might have to do with their more relative safety over using the actual picrates already prepared. quicksilver Super Moderator Posts: 1820 Registered: 7-9-2005 Location: Inches from the keyboard.... Member Is Offline Mood: ~-=SWINGS=-~ Good point. An interesting experiment would be an "exposure level" experiment. Wherein the tri-nitrated (or lower for that matter) material is simply exposed to a metallic salt in various conditions and from that, determined what (if any) resultant picate would be synthesized. Indeed, we could go beyond a focused synthesis & test whether (not to lead this discussion astray but expound upon a theme) time, heat, solvency, mother liqueur, pressure / density, etc...contribute to a synthesis? Improvisational techniques may benefit from "accidental" synthesis analysis in things of this nature. Such experiments could answer what level of heat, solvency, pressure, density are required to bring about a resultant primary (in this case). It could lead further to a look at other benzene-ring nitrated materials in their capacity to serve in the same context in the synthesis of a primary. Is picric acid the most efficient candidate for such a thing, etc? Hades_Foundation Harmless Posts: 23 Registered: 18-2-2011 Member Is Offline  Quote: Originally posted by hiperion42 Attachment discusses the mix of picric acid with litharge for use as a initiator capable of detonating the nitrated phenol. Forgive my ignorance, but isn't this just research for TM31-210 Improvised Munitions (section 1 No 20)? http://cryptome.org/tm-31-210-pdf.zip sorry if I'm stating the obvious. [Edited on 15-4-2011 by Hades_Foundation] 497 International Hazard Posts: 778 Registered: 6-10-2007 Member Is Offline Mood: HSbF6 Well this picric acid synth is different all right. So I thought this looked like the appropriate thread. According to the this paper, boiling various p-substituted phenols is pretty dilute HNO3, sometimes with vanadium oxide as a catalyst will yield picric acid. This is new to me. The best option if you can get it looks to be p-hydroxybenzoic acid. They boiled it in excess "4N or 8N" HNO3 for 1-3 hours and got around 70% yields of picric acid. The main byproduct is oxalic acid which they remove from the solution by addition of Ca(NO3)2. p-OH-benzoic acid can be made in >90% yields by thermal rearrangement of the dipotassium salt of salicylic acid at around 220*C for a 2-3 hours. Or you could just buy "methyl paraben" and hydrolyze to p-OH-benzoic acid (in situ possibly?), its pretty cheap and available in quantity. Alternatively you can go with an even easier to get substrate, tyrosine. To oxidize the side chain to the benzoic acid intermediate you have to add some vanadium pentoxide catalyst though. But it is like$40/lb and tyrosine is under \$20/pound.. They boiled it in 8N(~40%) HNO3 for an hour and then raised the concentration to about 9.5N and boiled for a further 2 hours to get a 45% yield of picric acid.

They tried it on phenylalanine and got p-nitrobenzoic acid in 40% yield. Maybe useful for other purposes?

Also worth noting that they got 95% yield of picric acid from dinitrohydroxybenzoic acid by boiling in 10 times its weight of plain old 8N HNO3.

It doesn't look like any of these reactions were optimized much. I'm pretty sure you could improve the yields substantially. I would also be very interested to see what happened to salicylic acid or aspirin in these conditions..

One thing I like about this route is that the acid is very reusable and you can avoid mixtures with H2SO4 if desired. Just cool the solution after the reaction, separate the precipitated crystals of PA, precipitate oxalic acid as its calcium salt, and you're good to start again. Once the water formed dilutes it too much, you can just boil it out, maybe even continuously during the reaction. If reused extensively it seems good yields based on HNO3 could be obtained. If using tyrosine NH4NO3 will eventually build up in the acid solution.

I would assume that a solution made by filtering the precipitated sulfate salt from a mixture of dilute H2SO4 + XNO3 and boiling it down to the correct concentration would provide an effective alternative to distilled HNO3.

I'm not trying to say that this is a superior method to Rosco's aspirin sulfonation/nitration procedure, at least until someone tests it But it's at least another alternative which may be advantageous in certain situations for a number of reasons, such as no need for H2SO4, easier reaction conditions (avoids foaming, stirring, exotherms, gradual additions of reagents) and no waste mixed acids. Another possible advantage is its lack of ability to detonate since no solid PA is present until cooling, and the liquid phase should always have far too much water to be detonable. Maybe it is more amenable to scale up than a traditional mixed acid nitration?

I've never seen anything similar to it for PA synthesis, though I haven't read this whole thread. What do you think?

P.S. On a less related note, I'm curious what you guys think are the best or most interesting energetic derivatives of PA? Sadly I don't have any means available to chlorinate it to picryl chloride, so derivatives based on that aren't an option.
Wow, never knew TATB was this easy! React PA with urea to get 88% yield picramide, the aminate that with hydroxylamine + NaOEt in DMSO for a 50-74% yield of TATB! Cool! Too bad I'm not drilling oil wells...

[Edited on 1-7-2011 by 497]
quicksilver
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I found this quote interesting:
"Morner (1915) (2) has obtained p-nitrobenzoic acid, picric acid, and
oxalic acid as well as the several other substances by oxidising protein
with nitric acid, and he pointed out that the parent substance of nitrobenzoic
acid was phenylalanine and those of picric acid were tyrosine and
phenylalanine which arose from the protein during the treatment with
nitric acid."

Remembering many of those very old protein-acid synthesis for picric acid ( such as horn, wool, etc), the concept of tyrosine makes sense. What's more the refluxing was only taking place for 2 hours (re: small yields).

What's interesting about the paper from a historical perspective is that it was published in 1941 (war years).
497
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Based on this old book and other references boiling of salicin in nitric acid eventually yields picric acid. I assume it would be formed by oxidation to (nitro)salicylic acid then decarboxylation and further nitration. One book even said picric acid of "remarkable purity" was obtained by boiling salicin in nitric acid.

This would seem to indicate that simply boiling acetyl salicylic acid in HNO3 of similar concentrations to the above japanese paper would give at least moderate and possibly good yields of PA under the right conditions. It may be worthwhile to hydrolyze ASA into SA before nitration if it turns out that the acetic acid from ASA increases the solubility of PA in HNO3 solutions appreciably.

Jimbo Jones
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I think SA is also OTC and may be found dirty cheap (compared to ASA) in the local pharmacy store.

Interesting found 497.
Rosco Bodine
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Hey even Rosco said his tried and true good old country organic synthesis was not necessarily optimized and could probably be improved, but is a good starting point if you don't have another method that works better ....red goo complications loom large as a potentially big one Actually aspirin is hard to beat for a precursor in terms of price and availability, but sure there are a dozen different potentially useful precursors and several of them are better than phenol in economy and convenience. I think it is probably possible to make picric acid using a slow dripped addition of the nitrating material as a concentrated aqueous
solution or possibly a low temperature melt from a heated funnel, consisting of one or several nitrates in a mix with either water or nitric acid. I'm just not sure what is the mix of conditions and concentrations peculiar to such anticipated schemes which will produce optimum results. The variables are there to make the final nitration a bit finicky about temperatures and times and concentrations and they are interactively interdependant on what curve the reaction follows so any process is likely to require some process modeling and fine tuning of reaction parameters to get the best result. Certainly scaleup will be favored by the nature of which process is worked out with that end in mind. Many of the nitrations reported are scale dedicated and work fine until you start changing the scale up or down. Then you get differing thermodynamics and reaction rates which leads to a lot of process algebra to work things out for the differing batch size. Actually that is generally true for more things than just nitrations. So anybody having a go at scale changes should be prepared for surprises which may be small or not so small.
The WiZard is In
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 Quote: Originally posted by Jimbo Jones I think SA is also OTC and may be found dirty cheap (compared to ASA) in the local pharmacy store.

Another Kitchen Tested receipt from one of my Uncle's
Low Albedo Books

At no extra charge - One Hundred Years of Asprin
from The Lancet.

Attachment: Chem asprin.pdf (70kB)

djh
----
Turn you yellow dye into
a brown dye.

Very sensitive to impact and friction —
violently explosive potassium purpurate
is prepared using KCN and PA.
Bot0nist
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Nice recipe Wiz. Who is the 'Official Use Only" for?

BTW, I love how you wield language. "low albedo" I quote you often in the real world.

[Edited on 5-7-2011 by Bot0nist]

U.T.F.S.E. and learn the joys of autodidacticism!

Don't judge each day only by the harvest you reap, but also by the seeds you sow.
The WiZard is In
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 Quote: Originally posted by Bot0nist Nice recipe Wiz. Who is the 'Official Use Only" for? BTW, I love how you wield language. "low albedo" I quote you often in the real world. [Edited on 5-7-2011 by Bot0nist]

Official Use Only

Is the lowest level of US Gov classifications followed by;

Confidential
Secret
Top Secret

Gov. Telephone book are often Official use only.

In years gone by - The CIA would have paid you a pile
of money for a Kremlin one!

djh
----
Where everything is secret -
Nothing is secret.

Anon.

caterpillar
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I love this acid, and made it many times. This nice compaud can be readely prepared without HNO3- one may use KNO3 (or NaNO3) instead. Phenol 250 gr plus sulphuric acid 800 gr (I took acid for accumulators, it was probably 92-94%). Put phenol into acid an keep one our at 100 Celsius by means of simple water bath. Put 1600 gr of sulphuric acid into a flask and add 1000 gr of KNO3. Cool this mixture down to 20 Celsius and slowly add cooled phenol, diluted in H2SO4. This mixture must not be hot. This process took some ours for me (I couldn't cool this mixture, because I used simple glass bottle). When all phenol has been added, wait for one night. At the next day slowly increase temperature up to 100 and keep at this temperature for one our. Finally put reaction mixture into large volume (10 liters) of cold water with crushed ice. Picric acid will precipitate. Wash with mall amount of cool water. Use gloves!!! My parents knew, when I made such experiments because yellow color cannot be removed from hands for one week. It would be better to convert picric acid to ammonium salt. It is less sensitive and do not corrode metals.

Women are more perilous sometimes, than any hi explosive.
Bot0nist
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Mood: Streching my cotyledons.

I also think TNP is a very interesting compound. Such beautiful crystals, and all the brisance one could need. Here in the bowels of the forum it has been discussed to death, and a search of TNP, picric acid, picrates, etc will yield so much good information that you'll be reading for days. In one of my past searches I uncovered a wonderful write up done by our very own Rosco Bodine. This write up has been scaled down a bit and ran multiply times, always with a beautiful product free of red and brown oxidized trash and superior yields when working from recrystallized acetylsalicylic acid.

picric acid from ASA , NaNO3 and 92% H2SO4

U.T.F.S.E. and learn the joys of autodidacticism!

Don't judge each day only by the harvest you reap, but also by the seeds you sow.
quicksilver
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DNP and TNP can visually construct similar crystallization architecture. The simplest method to determine if the product is TRI-nitrated is impact. 50mg in a small foil enclosure when struck, steel against steel will explode with violence (-=goggles=- foil flies, etc). The majority of nitrated products contain a percentage of lower nitration. When this lower nitrated percentage is substantial (especially w/ TNP) there will be no impact detonation. Benzene-ring nitration (especially those which utilize sulfonization) have few sensitive products that can be tested in this way. but fortunately TNP does respond to impact. Blurring the distinction is the use of DNP to form picrates (which it will). Impact test should always be kept at a very small level (50mg) as some products have a superior brisance (NC) and can possibly chip one of the steel surfaces. (USBoM 1914 "Commercial Impact Testing")

caterpillar
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As I know, even during WWII shells of large calibers was been loaded with TNP (with small addiction of nitrophenole, probably to decrease melting point). In Germany it was called "sprengstoffe 88". kalium salt of TNP is the remarkable compound too. Small piece of ti, been ignited, flyes like a rocket leaving behind black smoke. But if same compound is ignited in restricted volume it explodes without primer and leaves no smoke. I read once about a rocket propellant: 45% of ammonium picrate, 45% of NaNO3 and 10% of come organic binder, but I never tested it.

Women are more perilous sometimes, than any hi explosive.
chem77
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I don't know if threads ever die here, but seeing as this one spans 9 years, I assume they don't.

I've successfully made picric acid in the past, but today, my synthesis didn't work at all. I used the ASA + H2SO4 + KNO3 method, and I realized something was horrible wrong when I poured the acid mixture into the ice bath. This was always my favorite step because the dark red solution would burst into a brilliant yellow solution when it hit the cold water, but this time, the color never changed. I just poured the black/brown solution into the water and nothing happened.

I figured that maybe this discoloration would go away when I recrystallized the picric acid, but as I added the thick brown sludge to my boiling water, the water simply turned black. I decided that I wouldn't be able to salvage the picric acid because I was pretty sure I had more of this black/brown sludge than I had picric acid, though, I do know picric acid was produced because when I poured the stuff down the drain, as I diluted it, the water partially turned the classic yellow of picric acid.

Now, I'm tying to figure out what this stuff is. I tried burning it and it didn't burn, but it expanded like those pyrotechnic carbon snakes. There was only one step that seemed strange when I was making the picric acid, and that was when I mixed the ASA and the H2SO4. Rather than letting the alcohol evaporate off, I usually just boil down the mixture until the temperature rises to > 100C, that way I know all the alcohol is gone. But this time, since I didn't want to deal with the solidified block of ASA, I added in 1/3 of my H2SO4 (due to measuring device size) to the ASA while it was still hot (potentially > 100C).

After I added this bit of H2SO4, the mixture let off a bunch of gas and turned rather black. I figured it was just CO2 and I thought, "Screw de-esterfication, the H2SO4 simply ripped the acid group off the aspirin." But, is it possible the the acid actually destroyed the ASA? I'm not exactly sure what might have happened, but could it be something similar to the H2SO4 + sugar snake?

I have a feeling this step is where it all went wrong, but could the acid actually have turned the ASA to carbon (or similar)?
Kalium
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Have you ruled out the possibility that some sort of soluble additive was added to the aspirin? I don't think that the acid decomposed the ASA but I'm no expert. Personally I'd rather buy pure SA (used for homemade cosmetics), knowing that there shouldn't be any complications.

Oh, and the threads never die. People here get really worked up if you start a new one with a topic that already exists.
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 Sciencemadness Discussion Board » Special topics » Energetic Materials » Picric acid: different instructions Select A Forum Fundamentals   » Chemistry in General   » Organic Chemistry   » Reagents and Apparatus Acquisition   » Beginnings   » Miscellaneous Special topics   » Technochemistry   » Energetic Materials   » Biochemistry   » Radiochemistry   » Computational Models and Techniques   » Prepublication   » References Non-chemistry   » Forum Matters   » Legal and Societal Issues   » Whimsy   » Detritus   » The Moderators' Lounge