Apoptosis - 2023-09-23
In this video I synthesize the explosive compound picric acid or trinitrophenol from plain aspirin. PLEASE READ: I do not recommend anyone but trained professionals attempt this process due to several significant hazards associated with the synthesis and storage of this chemical. In this video (especially near the end) I made a few dry jokes downplaying the dangers associated with this chemical. These jokes were excessively dry and upon rewatching my own video I see how they could be easily taken as serious notes on the process. That said, I just want to be clear that this is chemical has the potential to be VERY hazardous. I intentionally made a very small amount, but with compounds that can potentially undergo rapid decomposition, safety is a very fine line. Just a few grams more than I made could be the difference between a loud pop and some broken glass, and something that could cause severe injury. Also keep in mind that metal picrate formation is only really a concern during storage (the small amount I made here using a sodium salt and a metal thermometer was removed in the recrystallization). That said, I don't recommend storing this chemical at all, and I destroyed this sample after I finished filming. Its my opinion that this chemical does not have enough practical uses to balance the risk of keeping it around, but I find this synthesis an excellent educational model. Support My Channel on Patreon! https://www.patreon.com/IntegralChemistry If you do insist on storing this chemical, it MUST be stored with at least 15% of its mass of water. It should also be checked and re-wetted periodically. This would be a bad thing to forget to do so again I'd just skip this on anything beyond the 2-5g scale. BTW this was done on request.. although its been several months so I forget who asked I do this one.. #chemistry #science #hydrogen #gas #elements #fire #chemical #industury #color
It does indeed stain things yellow forever. Fabric dye is actually one of its main industrial uses.
I thought so but I wasn't 100% certain it was still used for that these days^^ it certainly does a good job lol
@@integral_chemistry Yeah, I think it's mainly Asian countries. I think it's not used in the west simply because it requires more paperwork!
@@integral_chemistry
It’s literally permayellow
I couldn't help but wonder, after all those warnings about metal interactions, of course. Could this be able to stain stainless steel?
It was used on silk.
FWIW you can buy almost pure aspirin with no fillers and in powdered form if you look for aspirin intended for animal use (horses in particular). And it's really cheap too. This would bypass the need for the initial dissolution/recrystallization step.
huh.. I should definitely look into that, considering I use aspirin as a starting product fairly often. Thanks for the tip!
@@integral_chemistry The product name is "aniprin P" - the P is key, that's the one which is pure aspirin. There are other versions like F etc which have mixed other stuff in.
I think the whole point was to make it the hard way. Otherwise one can simply nitrate the phenol.
You can also jut get pure salicylic acid cheaply, it's used in cosmetics and as a treatment for painful callus on feet.
Butesin picrate ointment was used for years for burns. As a child my arm was severely scalded and was treated with the ointment. My arm was yellow for many weeks after the dressings were removed. It did heal perfectly, however. In an age of instrumental analysis, it is great to see old school wet chemistry in action.
Thank you! That was honestly why I started the channel, spent so long in school learning chemistry only to find we chemists don't really do much chemistry anymore..
Love to hear a firsthand account confirming that this stuff does actually work well to heal burns btw
This is a chemical I never wanted to work with in my research because of all the hazards. Respect for making it though, very interesting video.
Thank you! And yeah it was definitely a bit scary to make, although I did some testing after the fact and as long as its kept damp it really has a very hard time undergoing any type of decomposition
@@integral_chemistry I've always found the disposal and toxicity side more scary, not being able to work with significant quantities at a time and in my department, we have to report any picric acid use which means me as an undergraduate, is not gonna have a good time justifying my actions (even if I did work in an energetics lab) xD
As a chemistry reagent it comes 20g pure 100% in a small dark glass bottle. It's not wet it's crystallic and you can keep it for many decades.
"Can turn extremely exlosive when in contact with metals"
Uses metal stir rod
I hope you're ok ;)
Yeah no idea why I decided to just start using that to stir 😅 I'm okay though, it actually takes a good while for picrates to form
I thought that man was going to give a demonstration...😅
What made me watch your video was the fact that I had known picric acid since early childhood! My future mother worked during the war as a forced laborer in a German ammunition factory in Altenburg in the Harz. She was forcibly taken there from Poland, along with many of the inhabitants of her town. Picrin was used to fill the bullets in this factory; my mother recalled that the spilled picrin exploded under the influence of the slightest impulse, so her task among others was to constantly mop the floor to remove it. She also told me that people working in this department could be easily recognized by the yellow color of their skin...
btw helpful tip, remember to be careful of where it touches and if anything does you wash thoroughly otherwise it'll make its way to your hands and later on you'll notice a pretty bitter taste and that's how you know you just ingested a microgram of picric acid
As a schoolboy, I used to help the head gardener use picric acid ( he had a huge bottle of it in his storage shed!) to take out tree roots. I never understood the chemistry but it did make some spectacular bangs! Turns out the old boy was an explosives sapper in the war.
i missed my calling in life.
i should have been a chemist or a tool and die maker.
study hard kids.
dont end up with my type of regrets.
great content.
My father is a genius and would have been a heck of a scientist. But his father passed away when he was only 16. He went right to work, giving all his earnings to his mother until he graduated and married. He never got to go to college. He knows a lot and that scares people I think. But he has just been a very hard working man. He came up with several work processes that improved safety and that are still used today, fifty years later.
I've been there. Regretfully, chemistry as a profession is now dead. Go become a dentists, kids.
@@odissey2 no! One of the highest suicide rates at one time! ( dunno about now but back in the eighties/nineties)
Still not late ;)
Be a hobbyist
My mother only started studying to be a doctor in her 40s. Its never too late
Lol, I made some picric acid more than a decade ago and I had my right hand with those bright yellow stains for a month. Hard to explain to people asking because explosives were taboo in those days. If you light it, it will slowly burn very bright yellow and will smell light nitro cotton (nitrocellulose). I like that it crystallizes just like potassium nitrate but yellow instead of white. It won't blow up unless a blasting cap is used, or of course, like you mentioned, it gets mixed with some picratres from metal containers. Oh, by the way, picrates are the ones that give the whistle sound to small firework rockets.
😂 yes now explosives are totally OK and go round the office like: those yellow stains? Not that’s not piss that is TNP
Cool
You are very underrated, this was an awesome video !
Thank you so much! 😁 this one was a fun project but hell to edit down (started with 4 hours of footage)
Best chemistry video I've seen. Especially appreciate "I'll be quiet so you can just watch."
It's fascinating seeing how chemicals that have helped shape history are made.
In the 1970s I had a fly fishing store. We used picric acid to dye feathers yellow for fly tying. I got the picric acid solution from a hospital lab where it was used as a reagent.
I used to work as a histology technician in a hospital. We used a picric acid solution as a counter stain for the Modified Brown and Brenn which is used to stain gram-positive bacteria blue, gram-negative bacteria red, and the background yellow. The bacteria don't pick up the picric acid due to their cell walls having low permeability to it. This is probably more information that anyone other than a histotec cares to know, but though I'd throw it out there.
Nice. I remember making those needles in chemistry class back in the 50's. Good to know science basics are still out there if you hunt for them.
Large crystals aren't necessarily better than small ones. For best purity, you ideally want controlled crystallization with agitation. Also for energetics, you especially don't want large crystals, because they are more shock sensitive than small ones.
Years back we synthesised aspirin in chemistry labs, Dad who spent WW2 heavily involved in the explosive world warned against picric acid & mentioned it's presence on (especially) German shipwrecks from WW1!
Di Nitro Phenol was used as a weight loss supplement a while back but it was made illegal becuase It worked too well lol (gave people hyperthermia by raising their body temperature)... its made the same way as TNP but with a lower nitration temp.
huh.. I didn't know that, but now I'll have to go read about it. Thanks for the info!!
@@integral_chemistry Lookup the video "A Man Swallowed Lab Chemicals To "Lose Weight" And This Happened" by Chubbyemu. DNP was also used in some shell filling compositions, see "From explosives to diet pills: DNP poisoning in Wales".
@@integral_chemistry i mean, as a weight loss chemical it definitely helped people lose weight lol. it just did it in a really, really, REALLY dangerous way.
dinitrophenol is a mitochondrial inductor and uncouples the enzymes responsible for oxidative phosphorylation, causing ATP, glucose, and fatty acids to be recklessly burned by cells which waste a vast amount of energy as heat. the hyperthermia on top of the intense oxidative stress can cause many, many issues and there's no antidote if the overdose is big enough. the only proper care is supportive, similar to the treatment of serotonin syndrome -- IV benzodiazepines to control agitation and any possible seizures, combined with full-body cooling in the form of ice packs and/or refrigerated blankets.
It was made illegal for human consumption because it is a toxin that inhibits oxidative phosphorylation, and it can easily kill a person.
Actually Di nitrophenol don't go away from the body(it is stored in fat tissue). It destroy the "protons" gradient and the mitocondria can't make ATP no more. All the energy of foods gets wasted in to heat. The people get thinner and thinner every day until they die... I'm sure there are some portion of dnp in the mixture of the reaction
When I was a kid in my teens, I'm sixty-four now. I was all into chemistry sets and collecting all the cool chemicals I would read about. My father took me to a laboratory supply warehouse one day. They had water purification columns, glassware, and various laboratory chemicals and reagents. I was like a kid in a candy store. I proceeded to ask whether he had this and that and got to picric acid, and he said they had to quit selling that because someone tried blowing a safe with it.
You were lucky. When I was a kid I had no access to chemicals anymore.
Wow! Must have been like a kid in a candy factory! Lucky you had a father who enriched you're interest in chemistry!
Well I’m 52 and I can remember have access to potassium nitrate, boric acid, oxalic acid, potassium permanganate, 1,1,1 Trichloroethane (Carbon Tet substitute), sulfur, methyl salicylate, methanol amongst others in local pharmacies. That was well into the 1990s but days long gone.
Nowadays, I hear people leave reviews on Amazon about how Benzyl Benzoate made their skin burn like acid. To that I say, I doubt benzyl benzoate is supposed to be placed neat on the skin like that🤦♂️. That is why chemical compounds are hard to obtain.
In the old days (even in the 1980s) an interest in chemistry as a kid was seen as a noble thing. Now you are treated like a pariah.
I have a tube of picric acid burn cream that expired in 1996. I still keep it because I can't get more, at least in Australia. Yellow skin stains are a small price to pay when you're treating a painful burn.
Loved the final ramble on stains
LMAO I'm glad you appreciated it, a few people on here did not
Beautiful crystals.
thanks man, ive tried a couple of other methods of making picric acid but yours is the only one that worked for me
No problem, glad to hear it worked for you! I'll usually always try a few different methods for every project I do and then only put out a video on whatever ended up the most reliably reproducible
Had to dispose of dried picric acid at work that my boss swore was safe as it sat on that shelf for 30 years without hurting someone. Wonderful time
jesus.. Thats a job for a bomb squad (depending on the bottle size). Impressed you actually agreed to do that
@integralchemistry1849 that's what I said. We had a guy show up to start the disposal process. He just submerged it in water. But he never came back and I finished it. But the water turned yellow after a few days so we knew it made it under the cap.
It was probably around 100-200 grams. It looked like a 500g bottle.
It was also stored next to a bunch of oxidizers, hydrocarbons, and heavy metal salts. So much for proper storage of those chemicals.
God dayum. Chemical literacy man, this is why warehouses explode. Management needs to actually step up and manage things every once in a while.
wtf xD@@thecountrychemist2561
I had contract once to inventory the chemical stock of a research lab. Since I didn't know what was there I wore heavy gloves and a face shield. When I came to the 250 gram bottle of picric acid I stopped, informed the lab manager and he called the police who sent over a bomb squad technician who calmly picked it up and took it away.
Very eloquently presented. Very respectable yield.
It looked pretty cool in it's crystalline form, good work 👍👍
Thank you! And I agree, these are my personal favorite crystals I've ever grown
In WWI, picric acid shells were opened and used in field hospitals, to treat burns from picric acid artillery blasts.
This is as good as Nile Red used to be before he created a huge lab only to become a comedian and shorts producer. Your music volume level seems better. It's also not a bad choice. I was critical of your music previously.
Thanks man! And I believe you did, I've been careful not to make the music too overbearing or distracting as it definitely was fairly early in the channel. Thank you so much for the feedback :)
I agree Nilered fell off hard and definitely forgot his parent's garage roots 😢
I really missed the good old days where Nilered publish so frequently and every little synthesis in details, I understand his decision on moving on to huge project but the "filler" short-form videos aren't something I really enjoyed too much.
@@DangerousLab I feel that.. I feel that so many creators who make meaningful/academic content start by just wanting to share something they love and find beautiful/interesting with the world, and then once making content becomes their actual living source of income it always seems to become more pandering/outragous/theatrical and loses sight of what so many viewers loved in the first place. I don't watch much YouTube but the other big example I'm thinking right now is Philosophy Tube. Used to be just person in front of camera explaining dry philosophy which I LOVED and now its a 12-act 45 minute play with named characters, costumes, sets, post-production and its just kinda unwatchable for adults with jobs.
@@integral_chemistry It is probably so tough to keep up with the original once your income depends on it, it takes so much effort to stay on track as content creator who solely aims to provide meaningful and academic content.
Please keep up with your great work and continue to provide inspiring chemistry content!
Shortly after I was married in 1981, my wife finished school with a teachers certificate and a job teaching at a local high school. One of these schools in a not so well to do area. It just so happens I heard or read a news report about Picric Acid being found in school chemistry labs and if found, it should be removed. I guess there had been some explosive accidents with the stuff. I went to help the wife setup her classroom before the start of the school year and her first teaching job. Her classroom had access to the chemistry storage room. I was interested and looking around in there and found a large glass container labeled Picric Acid. I let the wife know what I found and the news I had heard. She let the principle know, who wasn't very concerned, but would check into it. I noticed the next week that the Picric Acid was gone from the storage room.
Did that happen in the Seattle area by any chance? I recall having heard on the news in Seattle of a local high school being evacuated or something when a bottle of picric acid was found in a chemistry lab.
@@browbu1954 My event was in Monroe Louisiana.
Gonna back this up real quick, I hope YT isn't going to take down another Picric acid video!
Great video btw! solidly explained and presented.
Tysm! Does picric acid usually get taken down??
@@integral_chemistry Not sure about it now, it was pretty controversial in the past due to its sensitive nature. I know Nilered took it down himself and Chemplayer has it taken down by YT IIRC. Perhaps it also depends on how the procedure is presented.
@@DangerousLab Yeah I'm thinking presentation is the critical factor. Hope I was mature enough about it to avoid that..
@@integral_chemistry I come across an article on Youtube "How YouTube evaluates Educational, Documentary, Scientific, and Artistic (EDSA) content", it explains the potential exemption for this very type of chemical reaction, I think it might be useful for you.
Nice video as always! You should be able to add the nitrate without the generation of NOx, which will also improve the yield. The nitrate needs to be finely powdered, well dried and added very slowly while maintaining 110 to 120 C.
I like your colourfull mechanisms. I do the same in my notes.
very cool.
Picric acid by itself is very safe regarding physical handling. It will no detonate through impact such as with a hammer, you need a detonator of similar characteristics as you need to detonate TNT. As the vid makes clear, you must be extremely careful with the metal compounds, the most unstable of which is gold picrate, which can detonate by lightly hitting it with a small pebble.
I hear lead picrate is similarly unstable.. but yeah my own tests definitely agree with you. The reason I didn't do a demo of its detonation is because I honestly couldn't even force it to detonate at small scale, and I didn't want to try anything larger than a half gram since I'm not too familiar with the explosive power of this stuff. Definitely nowhere near a fulminate in terms of reactivity
They use to use Potassium Picrate in fireworks for the whistles of unbleaveable decibels. :)
Very interesting. Picric acid is the best way to detect trimethylamine oxide, an osmolyte in many marine species. But you can't get it anymore. My sample came from a colleague who had a fireworks permit and could legally obtain picric acid.
The chance that you have already created iron picrate is quite high, considering that you had the entire time the metal probe of your thermometer in the nitrc acid. This is where the green color came from. This carelessness is very dangerous.
Yeah.. I figured that was the case. That's why I only work at extremely small scale like this because it's not uncommon for me to make little errors like that (although I think in general treating thermometers like stir rods occasionally is absolutely my worst habit 😅)
Also, to be clear this was not a careless oversight. I realized fairly quickly what I was doing and intentionally continued because I thought it would make a good joke. I'm not sure how much experience you have with this chemical but I have worked with it for years and the formation of metal picrates in the reaction mixture is of absolutely no consequence. It is quite literally incapable of detonation while saturated in water, and is completely removed and destroyed by the recrystallization. It is the formation of picrates during storage that is the big concern, and even still completely dry picric acid is only slightly less shock sensitive than most picrates.
Some early chemists added a brass band around the bottom end of their thermometers, so they could be used as stir rods with a reduced risk of breaking.
Of course, picric acid is likely to react with brass anyways.
Green, i'm thinking chrome or nickel as plating to keep it from corroding.
@@r.gilman4261 yeah I'm thinking chromium based on the color of the corrosion on this thing.
I was going to say, all this talk about the hazards of transition metal picrates and then you stir the reaction mixture with a stainless steel thermometer...
Forgive me if I am wrong here, but usually big explosive crystals=very bad idea. also ammonium picrate IIRC shouldn't lead to metal pictrate formation or was tin plating used to avoid the metal picrate formation?
According to literature, ammonium pirate still has a solubility in water at 1.1 g/100ml, compared to picnic acid's 1.3g/100ml. So it probably still disaccociates enough in solution to have the same effect. I'm not a chemist, so I'm just spit balling here
Ammonium picrate was used as "Dunnite", "explosive D", or "Shimose powder" by Japan. I consulted Urbanski for the downsides, but he had no negative remarks about it.
Yeah maybe not the best idea.. but they are relatively safe as long as they're kept dry and not made into a salt with ammonia or metal. And as far as I was able to tell in my reading they never really found a way to contain this stuff inside of metal long term (like more than 6 months or so) without significant picrate formation.. not totally sure though I could be wrong
@@_arthurski1337 IIRC Shimose was picric acid, and the way the Japanese got away from metal picrates forming was by tin plating the interior of the burster cavity. They then graduated to 2,4,6 trinitroanisole in the mid to late 1930s.
The reason the U.S. Navy used Ammonium Picrate was that it did not form the metal picrates and was relativly shock insensitve as explosive d was used as a burster for amor piercing shells.
@@integral_chemistryif you're using a picric acid based explosive, just lacquer the metal surface it might come in contact with. Plastidip would likely work too.
Oh man. Not Yellow chemistry! It's cursed!
Nitrogen dioxide is what gives nuclear detonation clouds their brown smoky color. It forms when air cools from a plasma formed by absorption of gamma and x-rays, and free N and O ions join. It could be smelled, along with ozone, lingering all around Hiroshima and Nagasaki right after the bombings. Ammonium nitrate detonations, like the one’s in Beirut and Tianjin, also form nitrogen dioxide smoke. The pre-dusk Beirut explosion had rich colors in it and was actually kind of pretty in a creepy sort of way. Very unfortunate.
Speaking of the staining power, Estonian traditional dress of the Muhu county is said to have been made from yarn dyed yellow with picric acid, obtained from WW1 naval mines that washed up on shore :D
Reducing agents will usually reduce only one nitro group to amine, resulting in picramate (which AFAIK is just as toxic and almost as explosive as picric acid. A proper disposal is difficult to achieve.
Sulfate ions may increase the ability of picric acid to get wet, so recrystalization may improve the purity and get the right melting point
Recrystalized ones do dry faster and aren’t get wet easily
Huh I'm not sure why I didn't think of that, but that is an excellent point. It did remain a little damper than I expected (which considering I want to keep it wet anyway is fine) but sulfate contamination is probably why
I remember when pa threw out an old can if burn salve because it was starting to picrate on the lid .
Keepon ramblin brother!! Some intresing stuff in that as well!!
I remember a download article of exactly this back in the '80s,
Anarchist Cookbook IIRC
The original use of picric acid was a very nice yellow dye for silk. But I caution anyone who wants to make it, as it makes very unstable salts when in contact with heavier metals. Some are so unstable as to make nitroglycerine look stable
You can see the difference between this Chemist, and the amateur Chemists with all our dirty glassware, eroded monkey bars and rusted hot plates! Oh and don't forget the occasional ( had to change out the condenser because I didn't properly clean it and whatever I made from whenever is now contaminating the new compound)! 😅😅😅 this guy's lab and equipment is like brand new and so squeaky clean! Wow! It's as if this gentleman actually knows what the hell he's doing and I dare say seems to have really thought out his work before he's even started!😅😅😅 refreshing sir! 👍👍👍
Thank you so much! 😁 I do try pretty hard to keep everything looking new and clean (it might surprise you to know that much of my glassware is years old).
Interestingly enough, the reason I try and keep everything so clean is actually a safety thing more than a contamination thing. I got the idea after I read a biography on Marie Curie and how her death led to all these new procedures for keeping lab equipment as clean as possible to reduce visual clutter and make potentially hazardous spills/particulate stand out better (you don't want the uranium nitrate spill blending in with all the other spills lol).
In any case thank you so much again for the kind words, I'm glad it doesn't go unnoticed
@integralchemistry1849 it's no surprise to me that you're glassware is mature! I was so impressed because I thought I was the only one who spends a bit much time cleaning up my glassware. I love how certain show offs will dedicate a whole video on how hard and long they had to clean up after their project, like that's what I really wanted to kill my time watching! As if they want the academy award for best cleanup 🤣! Always a pleasure my friend, I look forward for more of your content!
11:30 you know he forgot when he had to pee😂😂
@NuclearTopSpot - 2023-09-23
Yesterday: Ammonium Nitrate from garden supplies
Today: Picric Acid from Aspirin
Tomorrow: Weapons-Grade plutonium from old glassware and clock dials (how to build a breeder reactor)
@r.gilman4261 - 2023-09-23
I just use old smoke detector ionizing units...but that's just me :)
@EddieTheH - 2023-09-23
@@r.gilman4261 Yeah, the old soviet ones have a reasonable amount of Pu (some had a few mg). There was a guy on YT selling them for a while before the Ukrainian bollocks ruined it.
@davidedwards9157 - 2023-09-24
Yeah, every subscriber is now On A List(tm)...
@robertharper3754 - 2023-09-27
@@davidedwards9157 if you're not on a few lists by now are you really living life?
@thomasbonse - 2023-09-30
Such a nuclear boy scout. 😉