Making Trinitromethane/Nitroform (Part 1)
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- เผยแพร่เมื่อ 19 มิ.ย. 2016
- In this video I make what I believe is trinitromethane in possibly the worst yields known to man. I hope to improve this result in future. The extraction method seems kind of bad. The usual method involves distillation but I was worried about that causing an explosion. To simulate this in a more safe manner, I instead extract with DCM and then throw my flask onto the concrete.
Production: www.google.com.au/patents/US41...
Extraction: patents.justia.com/patent/4147731
The beginning reminds me of a time I was trying to learn how to cure a specific type of resin (phenolic) for rocket applications and found a nasa paper detailing their process. I stopped reading after they described how they first used some kind of electron emission something or other (not quite a scanning electron microscope but I knew it was out of my league) to inspect the SUV sized mold for a composite rocket nozzle before applying the phenolic and carbon fiber and pressing it with a few thousand psi of pressure at high temperatures.
I'd bet that the pressure and heat curing could be done st home on a really small scale. Especially if you have a rocketry club or friends to all chip in on it.
Well yeah but would the scale achievable at home be useful for amateur rocketry tho? Like Diamond anvils fit on a normal desk and the pressures are often generated by hand turned mechanisms, those generate the highest pressures we've achieved but only generate it on a nanoscopic area.
Nitrogen dioxide can be destroyed in a flame. My company used to do reactions that released copious amounts of nitrogen oxides. We found that a convenient way to get rid of it was to ignite a small natural gas flame and run the fumes into the center of the flame.
Does the burning of the gas not produce various other nitrous oxides? Or is that only the case with longer chain hydrocarbons that would be present in something like diesel? (I’m no chemist btw just intrigued)
@@shabbagadoosh The equilibrium concentration in a flame is small. In other words, there is a natural rate of formation in the flame that competes with a very large rate of decomposition. So you end up with only a tiny amount of NOx. I hope that makes sense…
@@atari7001 ahh very good explanation thank you
@@atari7001 Also, isn't that a question of temperature ? An open flame burning goes in lower temperature than the inside of the cylinder from a turbocharged Diesel engine.
@@VOID_WARRANTY yes, that’s true. Rate of formation in a colder flame is much smaller in comparison to rate of decomposition.
I love the smell of nitrogen dioxide in the morning.
@Squiggummer Figgammus My neighbors house was struck by lightning one time and the smell in the house after that was quite overwhelming. Had a hint of ozone as well..
Come to Delhi in that case, we have loads of the stuff
@Squiggummer Figgammus Kinda cool or should I say "striking" that one of the most important reagents for making explosives is created in nature by lightning!
I prefer dinitrogen oxide in the morning.
@Squiggummer Figgammus Excuse me, w h a t
If you don't want to go through the hassle of getting some cork stands for your rb flasks you can always use a roll of tape to put them on, that's what I do.
NOOOOOO
It's always a sad day when glassware breaks :(
Yeah... almost every day is a sad day...
neils bohr was a menace to glassware...
If glassware isn't breaking, it ain't a real lab.
Hahah at 15:10 your voice doubles up and it sounds like the three headed knight in Monty Python
ah it was in phase when I went it export, goddamn you Movie Maker. It does sound ridiculous doesn't it!
I thought he did it for the meme lmao
horse race announcer voice - hope there'll be no runaway reaction :D
@@ExtractionsAndIre Sounded like you had an extra audio track playing. Didn't last long so I'm sure it didn't hurt your subscription base. ha. RIP flasky.
When I first watched this I didn't know it but since then when I've done long refluxes (or any reactions) that produce huge amounts of NO2 or HCl or any kind of gas and I have high vapor pressure components in the reaction, even if their boiling point is nowhere near the reaction temperature, you can basically just lose everything to reaction vapor being carried away by waste gas. It feels like in this video maybe pretty much all the isopropanol got carried out by the NO2.
Now I use an ethylene glycol/water mix in a closed loop in my condenser with a CPU cooler radiator that I can submerge in ice water or methanol/dry ice. You have to insulate the condenser though or you get tons of condensation or ice forming on it. Maybe AU is dry enough most of the time that that isn't a problem.
i once had an idea of passing liquid butane through a condenser
or liquid ammonia
or cold ethanol
or pressurized gaseous refrigerant
@@VerbenaIDK I think you'd need custom glassware for that or just not glass at all, at least for everything but the ethanol.
Liquid ammonia and butane are kind of sketchy for sealed ampules. I imagine they would probably explode a condenser jacket.
There are a few places that make double-walled condensers (i.e. a condensing coil inside and a jacket on the outside) that might help with insulation from frost buildup but they're all $400 or more.
@@htomerif it would work if it's kept really cold and you are distilling somrthing that boils under room temp, maybe
if it was butane just whatever it'a gonna explode and shrapnel all around vut atleast it inst toxic like ammonia
@@VerbenaIDK Yeah, kind of. If you've ever had to do a reflux for several days though, you might start questioning how much you trust your cooling apparatus to keep the refrigerant cold enough not to explode.
People do do the dry ice/ethanol thing though and you don't have to worry about that exploding. I don't see why you couldn't just use a condenser loop from an air conditioner and put it in your ethanol tank for a more permanent source of cooling.
@@htomerif i actually never did long refluxes or anything really
just kinda brain fart there, i am the person that auddenly thinks "ok, imagine an oxy acetylene torch, but instead of acetylene, it's ammonia"
i dont have mobey to soend on glassware, shit is really expensive here and can get really expensive quickly
some day tho, i can dream
edit: also forgot to add, while the ethanol could kind of work, it would not be a great idea, i though of that becausr ethanol is very volatile and would boil fast and cool down, hell, even a half full ethanol bottle gets kinda cold at room temp, but then id not worry too much about the condenser itself exploding, but more the hose popping off and there was some ignitikn source near
I think you made a mistake in the nitroform formula on your blackboard. Those are meant to be NO2 groups, not NO3!
Good luck for your exams!
And we will never forget the sacrifice of that brave two-neck flask... :-(
Goddammit, I know they are NO2 groups why did I write them wrong! Ok this is a recurring problem now. I wrote the nitro groups as amines in the DDNP video, and referred to the NO3 groups in the nitrogylcerin video as NO2. I swear I know what i'm talking about, I just write it and say it wrong and don't pick it up until too late
See this is why I do badly at exams, I make mistakes even on the stuff I have been studying for ages and know really well
@@ExtractionsAndIre
It’s a shame exams don’t have questions like “make this strongbow can go away”
@@WineScrounger or the strongbow itself...
I spilled a Cadaverine/Putrescene mixture on my favourite sweater.
On the bus ride home it smelled like I stole clothes from a corpse.
The worst part was knowing that this particular mix was sourced from actual human corpses.
[I do Chemistry, not Goopy]
First I thought to myself man I am glad he is not my neighbor but then thought shit I like explosives .
Adds reagent to concentrated acid instead of the other way round
"Can't really see the nitrogen dioxide, but you can certainly smell it"
"So, we've got an acid spill, *and* a mercury spill, but that was my favourite flask"
Fuckin ozzies
Why don't we do nitrations by adding the acid mix dropwise instead of adding the other subject to the whole darned acid bath?
@@coopergates9680 We do, normally. As a general rule you don't add stuff to concentrated acids because reactions tend to be exothermic, and you really don't want boiling concentrated acid! For nitrations specifically, there's often more than one place a nitro group can add, so you want to control the reaction as closely as possible so you don't over nitrate. Although, if there's only one possible place then I suppose that doesn't matter.
Edit: and he's making trinitro methane, so he wants maximum nitration
@@RaunienTheFirst Well, he doesn't want to nitrate it further to tetranitromethane (though depending on reaction conditions the fourth nitration may be much less likely).
How sensitive/unstable is methylammonium nitroformate?
@@coopergates9680 not the faintest idea.
Yay, you actually did it! Shame the yield was absolutely horrendous, but I agree that the main problems are likely in the extraction steps. Although I'm not sure if the test of acidity meant anything, as there may have been a fair bit of acid dissolved in the product (nitric acid dissolves in DCM). The color is a giveaway for nitroform though.
Also, a quick note on the chemistry: nitroform has nitro groups, not nitrate esters. Also, the reaction proceeds very similarly to the haloform reaction: isopropanol gets oxidized to acetone, and via the keto enol tautomerism one of the alpha methyls gets three nitros from nitrate ions. This C(NO2)3- is a good leaving group (evidenced by its extreme acidity), and so ambient water hydrolyses the bond between the C(NO2)3- and the rest of the molecule, forming acetic acid and nitroform.
A quick literature search revealed some alternative preps, however. The reaction of acetylene gas with nitric acid also produces nitroform, but I can't find a reasonably recent reference on this. A more promising alternative is to start from chloroacetic acid, react this with urea to form chloroacetamide, add sodium cyanide and form cyanoacetamide, and react this with anhydrous nitric and sulfuric acids to form trinitroacetonitrile (Inorg. Chem., 2013, 52 (12), pp 7249-7260 --they use CCl4 but DCM should substitute, and they use 20% oleum but I think standard 98% conc sulfuric should work OK as well. No way around anhydrous nitric acid though.) The trinitroacetonitrile will hydrolyse in neutral aqueous solution to the ammonium salt of trinitromethane. This is really what you want anyways, since while bulk nitroform can be a little touchy, the salts are much easier to handle, and can be obtained from the ammonium salts by metathesis (driven by the release of ammonia gas)
Hey, thanks for the comment!
It's very possible some nitric acid dissolved in the DCM, however the whole point of that extraction method was the no nitric acid is extracted. This is advantages as you can then fluorinate the mix directly without some dangerous byproducts (see patents.justia.com/patent/4147731 Example II). That being said, whether the patent is accurate or I conducted it well enough is not certain.
Ah, such a stupid error for me to make. If I drew out the NO3 groups I would've noticed I wrote it wrong straight away. And from there I just propagated the error.
The mechanism sounds very solid. The patent also notes some oxalic acid byproduct, which is just further oxidation of the acetic acid.
Acetylene with nitric acid is another prep I might try in future, but if I recall correctly, it often needs a mercury catalyst to get decent yields, which lowers the appeal of the method quite a lot.
As far as the other method, that has +Chemplayer written all over it!
@@ExtractionsAndIre OG Chemplayer comment - It brings a tear to my eye.
Every experiment where the glassware doesn't explode is a success!
Ohhhhh yellow chemistry
AAAAARRRGGGH! NOT YELLOW, ANYTHING BUT YELLOW CHEMISTRY.
You missed a good rest in pieces joke for the flask memorial bit you did there...
I was half expecting three Powerpuff Girls to come out of that flask
You said that the light yellow was a good sign, but I thought you hated anything in your reaction that was yellow. (Though perhaps this video came before that).
Sometimes yellow is a necessary evil
RIP two neck flask.
This channel has lost its bright shining star.
That's how u know he's burning the midnight oil at school. He's either got it by now or working on it, his Chem doctorate, as of 2018-19 fiscal year. Gotta give the last of the hardcore chemists on here a break for even making it without getting cut by the tube.
To not dive too deep into biochem, The reason that tetranitromethane is more toxic than trinitromethane (which is more toxic in turn than nitromethane) is because the nitro groups really really mess with critical compounds and processes ranging from protein synthesis to promoting methemoglobin and thereby methemoglobinemia. Nitro groups are a nigtmare in biological systems. The more of them there are on a given compound the less compatible that compound is with, you know, living. Aromatic nitro compounds are used for that very reason in many chemotherapy drugs.
Just stumbled upon this page accidentally and I’m hooked 😂
Hydrazinium nitroformate would be an interesting substance to make... and build a rocket with it.
"light yellow is a good sign"
🤔🤔🤔
Looking at your chalkboard formula, I would have expected that you'd have started with methanol, rather than isopropyl alcohol, which has 2 methyl groups attached to the center carbon bearing the hydroxy group. What happened to the other 2 methyl groups? Does it say they were converted to CO2 or something?
Could you just use acetone or ethanol as well as in the normal haloform reaction?
nice attempt ! I think the procedure can be upgraded. To obtain a good yield of nitroform i suggest to make it from 99% isopropanol and an anhydrous nitric acid that can be obtained by extraction with DCM from a sulphuric - nitric acid solution. If you are interested i can tell you more about this procedure. ( this one does not use DCM for the final extraction).
I know to what dose mean break your own glassware xD break the heart see a 50€ round bottom flask crushing.
I really suggest to improve your safety equipment. Thats why i will donate.
Perhaps you could use chloroform to further extract any remaining product in the acids. Maybe the molecular similarity of the two molecules would allow for further separation.
Mate, I love your channel! Just an observation, though: it seems like you always start your complicated chemical extraction right as you're running out of daylight. What's up with that?
I mean, maybe it's just luck, but the few videos I've clicked on ALL have you doing involved chemistry by flashlight...
One day I'll be a more successful person and get out of bed earlier. One dayyyy
Isn't all mad scientists stuff done after school but before the parents get home from work? 😂
Probably this is a stupid question, but can't you just start with acetone? I think that the mechanism involves an oxidation before the nitration.
I was thinking the same. And it also avoid any possible nervous thoughts about isopropyl nitrate formation.
For some rfna was “really fucking nice acid” in my head rather than red fuming nitric haha
To be fair, it's both...
bit late to this video but what kind of gas filter did you use to your mask?
Would you like to make some Guanidinium trinitromethanide?
Is it true your not supposed to wear gloves with super strong nitric acid cause it sets them on fire?
Weird thought: Would bubbling the NO2 through water be worthwhile, both to control the emissions and reclaim some dilute nitric acid?
I recall seeing in your storage in plastic video that you had a bunch of (possibly plastic contaminated) nitromethane in an old wine bottle. I'm no chemist, but would it not have been easier, cheaper on the acid, and maybe safer to start from there instead of the isopropanol?
Hahaha this is one reaction I don't think I will try at home or in the lab.
hmm..haven't seen that reaction before...but you really should have a go at tetra nitro methane...I vaguely remember something about it being used for nitration's to make nice things...an old guy called Shulgin used to have some sitting around in his shack/lab ...probably diluted, don't know what with tho, but, hell that would be fun !
Tetranitromethane is highly energetic but it is super duper toxic. Like, chemical weapons grade. So it's just too toxic to handle :(
Did you use acetylene gas in that experiment?? 🤔
Good luck bro
I have only run one nitration in my lab (nitration of bipyridine N-oxide), but that fuming is very typical every time I run the reaction and my grad student said it's typical so 🤷♂️
17:46..no..I seriously doubt you have got any amount left in your solvent...I would say that it was your reaction conditions that are the culprit, you really needed to nuke it after the initial safety phase, doing it with a smaller batch would be a good idea too. To get a better idea of the reaction conditions needed for a better yield, you'd need to read up on what electron withdrawing effect those nitro groups would have on the carbon, and the speed of the reactions, whether it's going to be rate controlled or equilibrium controlled. I know it's not the nitric acid itself that is the nitrating agent, it's the nitronium ion, and it's that thing's rate of formation, rate of substitution and it's equillibrium that will determine the conditions..no doubt the geezers who wrote the method took samples during their cook up at intervals and checked it for trinitromethane and free RFNA and water etc etc...hmm maybe a little conc sulfuric could bind up the water from addition just like in a normal nitration, just spit ballin..havent read the patent or looked up anything...
I do hope to try this again some day. Looking at the mechanism, I think we had the opposite problem. One of the steps requires water... so even though it needs fuming nitric acid initially, there's an intermediate that needs water. So maybe just adding a few drops near the end will help it out? Hmm
Love your channel man👍 but I was wondering, what makes tetranitromethane so much more dangerous than trinitromethane? Thanks in advance for any replies, they’re much appreciated.
Hey man, glad you like the channel!
Biology is weird, very slight changes to molecules can really change their toxicity. If I had to guess without doing any research at all.... usually having a hydrogen attached to a molecule gives it a way of being broken down, like chloroform or trinitromethane. Suddenly, if you have no hydrogen there at all, the chemistry of the compound is dramatically changed, and your body can't process it nicely, like carbon tetrachloride of tetranitromethane. But unsure, toxicity of things is a fascinating field that I don't understand
Extractions&Ire Thanks for the reply! But that seems reasonable. When I’m not so busy, I will try to do a more in depth search about it and maybe try and find some sort of mechanism,since toxicity is something I find pretty interesting. Keep up the good work though :)
@@ExtractionsAndIre Maybe interesting sidenote:
From what I read, at least the american model airplane rules EXPLICITLY outrule the use of tetranitromethane (and hydrazine) in the fuel. Record applications do check the fuel for tetranitromethane content.
People actually were crazy enough to use this stuff, and from some reports (which are surely at least a little "embellished") you had to mix it in the chilled fuel shortly before use, because the mixture "decomposes" when it gets to warm for too long ..
But you apparently did get 50-70% power boost out of a few percents of it added. But is it worth 50-70% less fingers or worse?
Maybe acetone could be an oxidation byproduct of isopropanol and it would dissolve part of your product in the aqueous layer
Why didn't use acetone ?
People and their hobbies are so interesting to me
have you ever made picric acid?
Do dinitroanisole (maybe myrol for something more practical). I'd also like to see a sulfur trioxide vid. For the fume hood build a fume hood box thing and then use a bathroom ventilation fan to get rid of the fumes. Trinitromethane isn't acidic on it's own but maybe it formed a ton of the acidic anion. No idea of the solubility of the trinitromethane or like how to extract it more betterer.
Never heard of dinitroanisole but it looks cool, the anisole core seems a bit hard to get a hold of or make though.
I mean the outside world is alright for most things. The fan is only going to pump it outside anyway
Dinitroanisole is an explosive that the U.S. military might possibly be considering looking at. No idea why tho. It's not any more stable than something like RDX and the power and oxygen balance is DREADFUL.
13:33
Did you mean Rest in "Pieces"
500ml 24/29 2-necked flat bottom flask?
Why don't you trap the NO2 with a chilled cascading gas scrubber?
At 15:10 the audio sounds echoed for some reason.
It's really too bad so much of your RFN that goes into the reaction seems to just toss its shit in the air instead of sticking it on the IPA like it was supposed to. Is there any way to prevent that and reduce the amount of RFN needed?
You could attach a gas outlet to the condenser and run it into concentrated peroxide to turn the gas back to nitric acid. Not sure it would be worth it though.
Maybe add phosphorus pentoxide during the reaction?
Fuming liquids are the coolest things ever!
I can see where you might esterify the -OH on the C2 carbon, but the C1 and C3 terminal carbons are C-C bonded to #2. Can you please explain to me how RFNA is going to be able to add three NO2 groups onto any of the three carbons in the IPA molecule without just oxidizing the crap out of the whole thing? I know that 100% nitric acid will add NO2 groups across acetylene's triple bonds, but those bonds are already under considerable strain and are vulnerable to attack. I just don't see IPA surviving the reaction conditions.
If I'm missing something and this reaction does work, you might be able to improve your yield by using pernitric acid (AKA peroxynitric acid), HNO4, (HO-NO-OOH). Pernitric acid is nitric acid on steroids. It is easily formed in situ by treating HNO3 with 30%-35% hydrogen peroxide. HO-OH has the added benefit of oxidizing the red NO2 fumes back to HNO3, greatly reducing noxious NO2 emissions while extending useful life of the acid.
(2 NO2 + HO-OH --> 2 HNO3)
Starting with acetone instead of IPA might also improve the yield since the alcohol group on C2 is almost certainly oxidized to the ketone after it is esterified, which reduces an equivalent amount of HNO3 to NO2 and water. Starting with acetone eliminates that oxidation step and prevents contamination of the reaction mixture by water, but it adds another variable. The presence of the carbonyl group (C=O) on C2 of acetone will activate C1 and C3 to nucleophilic attack. It's likely that these carbons will undergo various degrees of nitration, adding to the yield of nitromethanes.
Or the whole thing might just make one big beautiful bang.
Frank Roberts I'm guessing acetone is hard to get in Australia, given the meth drama there.
I'm guessing that the mechanism is analogous to the oxidation of methyl ketones by hypochlorite. IPA gets oxidated to acetone, enol forms, double bond gets nitrated and reforms the ketone. The added electron withdrawing group speeds up the formation of the enol, and the mechanism reiterates itself another 2 times. In the end, the trinitrated methyl ketone is attacked on the carbonyl by a water molecule and C(NO2)3- leaves (I'm guessing that it's a good leaving group due to being able to stabilize that charge very well).
If this mechanism is correct then we should observe acetic acid (possibly partially nitrated) in the reaction mix, and the reaction should also work with acetone, or an alcohol like 2-butanol.
Antibumping granules?
It's always stirring, but some more granules might have been a good idea yes
Nice one! Rip flask, you will be missed 😞
Nice toilet paper with the flowers on it and all
Condensation line? It's a vapor front Tom!
Today a young man on acid realized that all matter is merely energy condensed into a slow vibration there is no such thing as death we are of one consciousness that is viewing itself subjectively here's Tom with the weather
Excuse my naivety, but don't you usually need some conc. H2SO4 in combination with the HNO3 to form the nitronium ion typically needed to nitrate something? Why are you able to nitrate the IPA without it?
I mean I see you _do_ use some H2SO4 (detailed @ 0:43), but that's not for the actual nitration step.
I can't quite remember, but I think it works By a different mechanism than the nitronium ion. We're not trying to form nitrate esters but using the HNO3 as an oxidizing agent... I think?
Concentrated HNO3 is able to form nitronium ions by itself, that's why nitration reactions on nucleophilic substrates can (and must) be performed without the aid of sulfuric acid. In particular here the nitronium ion doesn't have to break an aromatic structure (my guess is that it's attacked by a double bond from an enol), maybe that's why we don't need high concentrations of NO2+ at any given moment in the reaction mix for the mechanism to proceed.
Maybe adding sulfuric acid to the reaction mix would make a runaway reaction? I don't know if the low yield is due to an inefficient nitration of IPA, or complete oxidation reactions taking place. If the latter is true, then sulfuric acid would definitely not help.
@@pietrotettamanti7239 just saw your reply, very detailed and cleared it up. thanks!
I used to add IPA to nitric acid to make cleaning NMR tubes a bit more spicy:
th-cam.com/video/ga5rRkW-7uM/w-d-xo.html
That's the runaway reaction you're talking about. It's just a pipette of IPA.
To be honest , that nitration ratio of IPA isn't all that surprising, many other organics that are nitrated have similar ratio's, simply because the water formed catalyzes or rather prevents the forward reaction in the first place. So I guess using 100 percent HNO3 will help with yield. And, as with most of these nitration's, the waste nitric is reprocessed and recycled, some times even just reused without purification. Tetra nitromethane can also be made, but that's an ENTIRELY different animal....lol
I would suggest, to start the niration slowly, as you did, by cooling everything down, but then drive it to completion, by heating the reaktion mixture up, especially after adding the sulfuric acid. Because you have to nitrat 3 times, you have to use some harsh measures, don't you? And you increase the nitrating capability, when adding sulfuric acid, by binding water, but also by forming NO2+-Ions. But when you keep everything cool 'till the end, you aren't really using that, are you?
While yes, maybe heat might help the nitration, it also allows the other reaction to happen: oxidation. Cooling isn't about helping the nitration, it's about stopping you oxidizing the material and getting a runaway nitration. You can't add NO2 groups if everything has turned into CO2!
Sure, i got that. Does it actually oxidies to CO2 that easily, though? I mean the recipe you follow suggested put the Isoprop in 60°C right? And i dont mean to do that, but to slowly rise the temperature after adding the sulfuric acid, until something happens ;D
Or do you think most of your loss already is due to oxidation? Is your yield actually as bad as i think or is that just a misunderstanding on my part?
And thanks for answering at all :)
Wrong formula, not "NO3", it is "NO2"
For future reference, you are better off working without gloves next to an open source of water when dealing with nitric acid. It can set gloves on fire in the time it takes to get them off at the elevated temperatures you were dealing with. If you've never seen nitrile gloves go up in flames, it is worth doing as a demo once.
That's a fair point, but the gloves you see me wear in the video are not nitrile but rubber. They probably still has a reaction with concentrated nitric, but I wear them when working with conc. sulfuric or combinations of sulfuric and nitric because the burns are bad. Nitric burns to the skin aren't painful but look very bad, but sulfuric would hurt (I actually don't know for sure, that's a win for the gloves!)
Sulfuric acid burns sting like a thousand bees heard you talking shit about their mum. But, it takes a bit for it to actually get through the skin. If you just leave the tap running while working with them, you have ~10 seconds to get your hands under it without any issues. Nitric burns look ugly because it reacts with the keratin in the outer skin layers. It is when either acid gets to the layers beneath that you feel anything.
Heavy rubber gloves are fine for either acid. I presumed you weren't using nitrile as most of them are blue or purple.
@@xenomancer1 No tap present that I can see, but a small bucket of bicarbonate solution for a fast dunk might be invaluable some day.
Tom, I have an idea to maybe reduce bumping. The big, sudden appearance of bubbles at the bottom of the flask create the problem, right? What if you put a heating mantle element on the TOP of the flask (like a knit cap), maybe extending down to the surface of the liquid? I think the liquid would sizzle at the top, but have no reason to bump from the bottom. It might help foaming too, but that's just of a guess.
Is there really a high chance of blowing yourself up with making this stuff, in say a 50 gram quantity?
nitrogendioxide is useful in itself... worth capturing somehow?
Actually yes, its worth bubbling it trough your diluted nitric acid to increase concentration, you have to do it in ice bath to increase absorbtion rate.
Dont want to be a nanny, but i once heard you should not store your solvents in the fridge, because thats a common cause of fire in the lab. Better store them somewhere cold and well ventilated.
Depends on the type of fridge. They make explosion proof fridges for that reason.
Why not invest in a bump trap.....also there is a much simpler synthesis method utilizing acetylene reduction of nitric acid containing mercuric nitrate. This give you nitroform. The byproducts are CO2 and nitrogen oxide which then can be converted into nitric acid with an absorption tower....
Please make Part 2!
Good news! I did make part 2! th-cam.com/video/sfaWHlF1uR4/w-d-xo.html
Cheers mate
Speaking of sad moments with glassware, recently I was making nitric acid and on the cleanup (always the fucking cleanup) I was poking at the cake that formed in the heating flask to break it up with water inside (wasn't even poking hard mind you) and the base just fuckin cracked and fell to the ground, had a long life and I think heat stress just got to it
pentanitrotoluene next?
Way better than the boring compound that is trinitrotoluene.
You ever going to make yourself a vent hood so you can do it in the shed?
Possibly one day, but for now, outside is ok. There's plenty of sunny days in a year down here
Nice bong man
Acetone react with liquid Dinitrogen tetroxide in ice bath should be easier.
RIP flask
Shit, Tom, you have something worse than a nitric acid spill and a mercury spill. You have a mercury nitrate spill. Here's hoping you used extreme caution while cleaning up that very soluble compound.
Why not in future reactions like this add an addition funnel on top to the condenser with an intermediate piece of glassware with a vacuum adapter and put a balloon on there?
Anytime I see the word nitromethane I'm there can you put this stuff in an engine
Tetra(!)nitromethane was once (1950s) used as an additive in model airplane engines, mostly for records. In those times, the fuel wasn't prescribed yet, and some guys started to use this stuff.
I read forum posts by people who witnessed it during that time, and that stuff set asphalt on fire if you spilled it, and you had to add it to your fuel just before takeoff, else you were at risk that your fuel tank may blow up. If you spilled onto your hand, that was a hospital visit .. if you were lucky.
The engine life time dropped to basically minutes, too. If it didn't literally blow up even before that.
But to be competitive, you had to use it. Because it was THAT dangerous, it is (at least in US AMA rules, in EU you aren't allowed to own, acquire or make it since it is listed as an explosive) explicitely forbidden to use until today.
@@VintageTechFan yes I know I grew up on a drag strip and I played with the model engines and they still use it. 🙄
@@danisyx5804 Nitromethane, yes.
TETRAnitromethane, not so much.
@@VintageTechFan I thought this was trinitromethane. And wouldn't all of these be nitromethanes?
@@danisyx5804 Technically, yes. But "Nitromethane" on its own means the (Mono-)nitromethane with one nitro group. This is still commonly used (even if the EU limited it to 16% per weight recently). Never heard of the Di- or Trinitromethane used in/as fuel.
RIP 500 mL 29/32 flask 😢
Wtf it was a 24/29 2 necked flask? Well then do not RIP^^
29/32 ftw. I hate it when i'm watching for 29/32 glassware and connectors and only find those bizzare useless pieces of glass^^
24/40 ftw
Ever looked into tetranitromethane? It is usually made by nitration of acetic anhydride with fuming nitric acid. As a reagent in organic chemistry it has very interesting properties, but it is so sensitive it is a real danger to use and store. The glassware must be sparkling clean, any hint of organic contaminant can set the stuff off. EDIT: 3:40 just heard you have considered it, yes it is indeed far too toxic and dangerous
Poor flasks, that's so sad man.... :'-(
Boom
Extractions&Ire make hydrazinium nitroformate (hydrazine nitroform; HNF)????
Yeah that would be cool! I should revisit this nitroform synthesis one day
@@ExtractionsAndIre спасибо супер
F for the broken flask : (
Nitro = NO2; Nitrate= NO3; Don't confuse them.
👍
@Whoop.!!
Acetylene and nitric acid also makes TNM...
If this method doesn't work, i'll try that method, but I think you need a mercury catalyst? There's some catch if I remember. That and I don't like using my CaC2 unless I really have to
do you have a welder in the shed? you could make some CaC2 via electrolysis
Hi,
be carefull, nitro group is NO2, a nitrate group is ONO2
please could you detail the mechanism of the reaction, you should have production of carbone dioxyde
try this: pubs.rsc.org/is/content/articlelanding/1947/jr/jr9470001234#!divAbstract
@@alvarezfrederic4997
Why carbon dioxide?
nitroform can be produced by the reaction of acetylene with anhydrous nitric acid.
It requires mercury(II) to catalyse the reaction, which is not very friendly
Extractions&Ire without risk experiments will become boring
@@ExtractionsAndIre I read that reply as you said "huge cloud of nitric acid" in the video. Lmao! You've dealt with worse shit than mercury (II) compounds, why not try it?
Man, I bet that apparatus would hit like a dream!
Zen Jon that’s the real reason he got it.
I have the same toilet paper!
I would RATHER have the C(NO2)4 personally...
0:50 oh no no no ... i don't hno chemistry
I don't know if that was said on the video, but care about poisonous properties of nitroform.
He said about nitroform being "poisonous, but okay" and the tetranitromethane being "chemical warfare levels of hazard".
Try to make tetranitromethane! It was used as an additive to Diesel fuel to improve the CETAN-number. Its quite harmless when pure but quite explosive when mixed with hydrogencarbons. Very explosive with Toluol.
Synthesize Trinitrotoluene(TNT)
And call it something like nitration of BTX fraction extract so it won't get removed lol.
It's waaay too simple.
RDX or octanitrocubane, please!
@@californium-2526 HMX
@@brandysigmon9066 Good!
I am not brave enough for chemistry..... that's probably why I decided to study physics, I guess
can CHCl3+nitrite make nitroform?
I don’t think that the Nitrate can replace the chlorine
Trinitrotoluene when
I'll hopefully be buying some toluene soon! I have the container and I made a sweet label for it, it looks very health and safety abiding.
Extractions&Ire this is gonna be sweet if there was only a guy that could replace that toluene with a cyclic amine :^)
Fryyyydge ;D