Making Adamantane From Jet Fuel
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- Опубліковано 29 лип 2022
- In this video I will be synthesizing jet fuel (JP-10) aka tetrahydrodicyclopentadiene and adamantane. Starting with purifying dicyclopentadiene, followed by a hydrogenation to form tetrahydrodicyclopentadiene. Then, through an acid-catalyzed rearrangement, Adamantane can be formed. Adamantane is a molecule that is a precursor to many different types of medicine.
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For all of your work, you may have gotten 2% yield but you also produced a great video about adamantane chemistry. In my opinion, that's better than 100% yield alone. 🙂
Very neat synthesis! I didn't realise adamantane was that easy to make
Even easier by reacting ammonia and formaldehyde which yields Hexa-methylene-tetramine (Tetra-aza-adamantane), an Adamantane cage with four Nitrogens attached. Remove the four Nitrogens atoms and you got pure Adamantane. ;)
This is actually a very impressive and well-demonstrated showcase on extractions and uses of basic hydrocarbons into much more exotic ones, job well done! 💪🏻
The whole first half of the video had me smiling. I work with dicyclopentadiene and the monomer a LOT in my current PhD research. It's fun seeing other people work with it.
I love how you always synthesis beautifull molecule
This synthetic chemistry chemistry is not only very intelligent, but he is also an excellent instructor! He makes complex concepts interesting and easy to understand! This is coming from someone with dyscalculia, so that is strong proof that he is a phenomenal instructor!
To all the synthetic chemists on UA-cam, PLEASE start using an appropriate-sized flask for your reactions. The total volume should never exceed half the flask. This will help you if you have a runaway reaction, exotherm, etc. The situation at 7:13 is such a safety hazard!
How exactly a bigger flask help with runaway situation?
@@user255 more headspace is more containment. In these reactions and distillations, there is no headspace. Any expansion immediately exits the flask onto the bench and, possibly, the chemist.
@@jacoboleary9076 Um... no. You must always have plan for broken flask anyway. Bigger flask is quite insignificant factor to prevent spillover in runaway situation.
@@user255 Who said anything about a broken flask? And you're welcome to have your own (bad, unsafe, non-SOP, absurd, take your pick) take on lab safety and chemical hygiene, but please kindly keep them to yourself. And make sure you've got proper PPE and secondary containment next time you run a reaction.
@@jacoboleary9076 I said about broken flask. The point was that the flask size does not matter all that much, because it may broke or spillover anyway. Thus you must have plan for spillovers etc anyway. Got it now?
Bigger flask of course helps, but it is far from being critical for safety. More of a convenience issue.
Edit: I would *never* put my safety to depend on flask size. The PPE, secondary containment, etc are for that.
Your videos are just getting better! Thank you for your videos!
This was very cool, sir! Your presentation is much appreciated.
nilered expet he is underated af keep it up i love these videos!
Look at that, you have another great sponsor! Congratulations! You deserve it!!!
The adamantane derivative which most comes to mind is amantadine which is an amine derivative which is used to treat Parkinson's related dyskinesia.
Lol I can see that your video style is inspired by nilered nice! I appreciate you explaining the chemistry with pictures of the compound structure
Aye nilered got it from nerdrage
The mechanism for molecular rearrangement in this reaction is fucking magic
2:00 Pd/C on its own isnt really pyrophoric. Only when hydrogen is still sitting on the surface of the palladium it becomes reactive and can possibly burn if exposed to air. Thats why you often burn the Pd/C cake after filtration to make sure that you dont accidentally burn down your waste container
Hmmmm - when scooping up large quantities of fresh Pd/C I've seen it glow in the absence of H2. On the large scale we always handled Pd/C quickly and kept the bulk container closed. It may not be pyrophoric by definition but it's definitely tricky to handle.
you do what? even after filtering organics off you would think to burn the filter cake? we store it under water its fine. what youre saying is madness to me
@@user-mp4bc9qp2x I don't just think about burning it, I actually always do it as it is a fast and safe way to deactivate it. You can easily collect the Pd residue and throw it away if necessary. Why store potentially harmful waste if you can just dispose it after quenching it in a matter of a few minutes
craziness. do you light a match to burn it or use a lighter?
@@user-mp4bc9qp2x Just roll up a piece of paper, light it on fire and hold it at the filter cake. Often it doesn't burn that well it just glows a bit for a few mins. It really isnt nearly as dangerous as it sounds.
I didn’t go through all the comments to check if this has already been said, but I’ll say it anyway. Typically, to decolorize solutions with activated carbon, the rule of thumb is to use the amount that fits on the tip of a spatula. An entire spoonful like you used definitely adsorbed at least a little, or more likely a significant amount of your product, which decreased your yield
dude I literally couldn't find any videos on JP-10, good video
That Chemist sent me! I will stick around for more!
Take a shot for every cyclopentadiene
Also le funny baseball cap shaped molecule
you deserve a ton more subs!
Amazing video!
Interesting video. Took less steps that I would have guessed.
Fun fact:
Due to the structure of adamantane, it is uncharacteristically hard for essentially a pure unsaturated hydrocarbon. No other isomers even come close. It’s firmness is close to medium hardness plastic
thanks for making "Adam and Dane"
Normally it's synthesized under increased pressure - perhaps that's the reason for the low yield.
Your video are ever interesting and well done. But about this one, more than adamantane I would focus on that tar. If you mix with dehydrogenating catalyst, on open flame you can recover a lot of aromatics as naphthalene, anthracene and so on.
This UA-cam channel is a second stage of Nile red.
You seen nurdrage? He's got good chemistry videos.
@@antifreeze-30degrees49 Yes i have, he is good.
Thanks
03:56 : It almost looks like Chemi is making a homunculus💀
“today, i will be making some adamantane from jet fuel. but first i have to make some jet fuel”
sounds like a nilered quote
I've seen this before, but never done it because hydrogenation is inaccessible for me. Cool synthesis though, I envy all your stuff.
Fascinating synthesis. What is responsible for the change from liquid to solid after hydrogenation?
It changed into a different chemical.
Anhydrous aluminum chloride often fumes due to spontaneous formation of its aquo complexes in moist air. Release of HCl requires heat, and while complexation is exothermic, it is possible to prepare AlCl3 solutions in water and isolate the hexahydrate without converting to alumina and HCl, so long as temperature is controlled
Do you somehow neutralize AlCl3 after the reaction?
I wonder if the synthesis of adamantane like tooltip-molecules for evetntual furure mechanosynthesis of diamond (like e.g. DC10c) follows a similar pathway.
Diamonds are formed when carbon is inside a volcano at super high temperatures and pressure. There are also synthetic diamonds which also use high temperatures and pressure, but they sometimes have more contaminants.
man imagine like smelling this though
youre basically just inhaling absolutely tiny diamonds
This could have easily been an April Fools joke and 97% of the viewers (me included, of course) would not have been able to tell otherwise.
Nilered vibe🙌
Is it common between chemists to participate in a yield-measurement contest?
Can you use Adams’ Catalyst?
Yo, this is the shit! I love this! Now make memantine from it.
EDIT: My very bad, I missed this 2% yield at the end :/ It would be worth putting it written on video anyway.
And what I am curious, what do you plan to use adamantane for? Or you made it just for making it?
Very nice synthesis!
After you said about adamantane subliming, I expected you would finally purify it by sublimation for ultra purity and crystallinity.
Also, you should always give yield in %, not in mass. Saying "yield is x grams" means nothing without calculating it with starting mass and so on. This is the most aggravating thing in some patents and papers. Always put per cent yield or "yield was x grams with is Y %"
Did you miss the end of the video where he says, based on the starting material thats 2% or something?
@@10Mike10 He said that? Then i missed it if so. Produt mass was shown on screen and talked about then maybe this just was more memorable. Definitely I will rewatch then (for better stats for video and to see that I am wrong). Thank you for pointing that i missed it!
Take a shot every time he says dycyclopentadiene.
Cool
I don't know why, but I can just picture some random dude saying: "Well boys, it's time to make crack with some jet fuel."
where did you get the dyclopentadiene?
From a chemical supplier.
Should be easy to make 1-aminoadamantane from this (haven't checked, just an armchair educated guess, nitration & reduction?) ; which is interesting for its antiviral properties (influenza A treatment).
Make bromantane or Phenylpiracetam Ill buy it. Not enough Racetams on the market sadly :( Aniracetam, Oxiracetam, fasiracetam, phenibut sre all so much harder to find, If you make it, Ill buy it
They have racetams on the internet. Racetams and Modafinil and Methiopropamine (MPA). Synthesized by other chemists. Chemists also synthesized pharmaceuticals, but a doctor has to prescribe it to you.
Good first step. Now how do we go about nitrating Amantadine?
Good first step for what?
Nitric acid. Trying to make 1-Aminoadamantane (the anti influenza drug)? Good pharmaceutical drug.
Memantine from adamantane pls!
Can it melt steel beams?
😂
Oof, glad the yield was greater than 0
Apparently JP-10 has usually about 1% of adamantane by itself.
What does adamantane smell like?
I find it to smell minty. Tetrahydro pretty much smells the same.
@@Chemiolis Thank you. I find the smells of organic compounds fascinating and cannot resist taking a sniff when not imprudent!
turns it into metal alloy with silver and mercury.
Hallo dutchies represent, je kan het accent niet verbergen~ dit kanaal is gekoloniseerd
kut
Actually, major component of JP-10 is exo-isomer, not endo-, which is solid with mp >60 degr. C.
Nice video, liked+subscribed.
I concur - I've made the fuel on the industrial scale. The product didn't freeze at room temp. A good jet fuel would not freeze at room temperature. The industrial process does not include the pre-hydrogenation steps.
From NISTIR 6640:The Fuels Branch of AFRL (Wright Patterson Air Force Base) required physical property measurement and modeling on an aviation turbine fuel, JP-10. This fluid is essentially a pure component: exo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane, CAS No. 2825-82-3).
so, why call it "tetrahydrodicyclopentadiene" and not just dicyclopentane?
The name tells you more about the structure, that it is a diels-alder product from two cyclopentadiene molecules of which the double bonds are then hydrogenated. The IUPAC name is more complicated so people just used something easier (dicyclopentadiene was probably already known before the standardization which made it easy for people to know the structure of it if you just put tetrahydro in front).
It adds 4 hydrogen atoms to hydrogenate it. The IUPAC describes the molecular structure. There are more common names too, which scientists agree on.
@@Chemiolis- As you know, simply reacting ammonia and formaldehyde yields Hexamethylene-tetramine (Tetra-aza-adamantane), an Adamantane cage with four Nitrogens attached. Is there a way to remove the Nitrogens atoms by any method to yield pure Adamantane?
Cylopentadine 🤔 know we're talking
Good video but you should practice accurate narration of technical terms. When I was making chemistry videos I had the same problem but I'm taking a break right now
Adamantane look like Hexamine or Hexamethylene Triperoxide Diamine for me.
Why did i read the title as "Making adamantium from jet fuel" ? 😂
Adamantane is a real chemical compound. Adamantium is a fictional element from wolverine, the fictional superhero in X-men movies and comic books.
@@antifreeze-30degrees49 Yes, I am very aware 🙂
I am amused that hydrating the molecule makes it look soggy. Look at that soggy boi, he wet.
Hm, I thought you were going to use hexamine
Surprise!
Tetrahydrodicyclopentadiene? So, dicyclopentane?
Dicyclopentadiene.
For a second I thought how the hell do people make adamantine
I’m disappointed by the lack of Adam Ant puns in the comments
wolverine, there I said it
:)
Damn, Adamantane is a cap,
disiclopentodaimn
Say dicentahydrodyline again, see what happens.
Great vid, btw do you have a discord server ?
I don’t, but you can join That Chemist’s discord, I’m also in there 😉 I’ll ask him to make a text channel specific to me.
Why don’t you make a server ?
@@Chemiolis Make your own :)
@@octanitrocubane I don't know much about discord and I probably can't moderate it properly. Considering we share a lot of audience, it is more efficient to combine the communities. There is now a channel specific to me in the That Chemist discord, so anyone interested can join. discord.gg/thatchemist
@@Chemiolis ok, what’s your discord tag, couldn’t find you on that chemist‘s server
the word "hydrogenation" and a home chemistry channel just doenst go well thogheter with me
Wow! This is beautiful! Impressive chemistry and good lab work. I love your videos. Never knew that THDCP was a rocket fuel component. ⚗🙂👍🏻Nice to learn something new.
It's jet fuel. I think they use Hydrazine for rocket fuel.