Extractions&Ire - 2022-12-18
I'm a simple man trying to drive a simple photochemical ring closure reaction. What could be more simple? Twitter: https://twitter.com/Explosions_Fire Subreddit: https://www.reddit.com/r/ExplosionsAndFire/ Join the Discord!! https://discord.gg/VR6Fz9g Patreon: https://www.patreon.com/ExplosionsandFire Music: from the Aphex Twin soundcloud dump. Track name: Pretend Analog Extmix 2b References for the whole cubane synthesis: 1997 Lab scale paper: https://www.researchgate.net/publication/244572672_Dimethyl_Cubane-14-dicarboxylate_A_Practical_Laboratory_Scale_Synthesis 2013 Pilot Scale: https://pubs.acs.org/doi/abs/10.1021/op400181g "Cubane Derivatives for Propellant Applications" 1989 https://apps.dtic.mil/sti/pdfs/ADA210368.pdf
"sick of this contamination shit" he says as he does organic chem in his garage
crack shack*
with a post apocalyptic looking mobile fridge
Never seen him run a flash chromatography. I understand that it's not very practical nor economical to do while funding the solvents yourself nor remotely safe without a proper fume hood, but you can't expect your product to not be a mess of different compounds after several steps. And it compounds, because without being certain of decent purity after each step you have no way to do the stoichiometry accurately either.
don't forget that nilered once cooked a spider with his boiling mercury
@@takeawaykitty. No no, he's made it very clear there's no drugs. It's a rat shed that also occasionally has snakes.
Wake up babe new cubane video
I haven't been this excited for a YouTube video in a minute.
Yes wake up from your 7 month coma
LITERALLY
@@stutterpunk9573 punk love!
forsen1 I C BAJS
NileRed: Rents an entire island to boil acetone
Ex&F: Spends years attempting to synthesise an incredibly complex molecule using hot glue and a tin can
The lowest effort
@@mamupelu565low effort? I would say this is high effort to do it in the most complicated way possible
So I'm a PhD student that has had the misfortune of having to work with compounds with the same functionalities as your product. Trying to analyse them with TLC is a real pain. There is nothing to oxidise, so KMnO4 does nothing. They don't absorb UV-light. Iodine only sometimes work. I saw some other comments suggesting some more exotic stains, which I haven't tried, bit I think there is one more accesible one that you should try first: vanillin. Vanillin is an aldehyde, that, if activated by a strong acid, is a very strong electrophile that reacts with essentially anything nucleophillic. The products are often coloured, so they are very easy to see on TLC. Ketones can under acidic conditions tautomerise to form nucleophillic enols, and I've had some success with it for this type of compounds. It also smells very nice.
To make the stain, just dissolve vanillin in 1% H2SO4 in ethanol. You will need to heat the plate quite a bit to see anything, but if it works, it should be pretty obvious that it did.
Good video as always, BTW, I think you are pretty close to figuring this out now.
Comments so he sees this more bigger
And anisealdehyde
Things are gonna taste yellow
my question is why not spectrum machine? he is still a phd, right?
Yea Vannilin is a good one to try. Neat bonus: it smells really nice!
We need to get a "Have you seen this molecule?" message on the back of every milk carton
And then a shirt of such a milk carton image for merch
@@ripvanwando I'd buy that.
That was exactly what I was thinking too 😆
@@ripvanwando seriously, that is so merch
@@kumoyuki i'd wear that
The project has been going for over 2 years already? Damn life moves fast.
Yeah man too fast
@@ExtractionsAndIre Life moves fast, chemistry doesn't. I live my life a 0.25 mol at a time.
No wonder it feels like this series has been dragging on for so long, these last few steps have put grey hairs on my chin.
I'm glad to see the vids back. I have the playlist saved and every so often I saw it on the list and thought, "hope the cubane guy is doing OK"
2020 didn't happen so we kinda lost a year
I feel like having a good pair of tweezers might improve this man's life significantly.
Yeah they'd make it much easier to catch that funnel web spider hiding in the walls
I was thinking that a pair of kitchen tongs would make it easier to put the cuvette in the photoreactor.
Or even just tongs
@@ryanc473 silicone ones might be useful, if you can get small ones, for friction
The guy has hemostats from an old family vet practice. He just doesn’t use them.
The contamination is probably just the spider pooping in your DCM as revenge.
Albeit a small thing I think what happens at 6:59 is a good descriptor of why we adore your channel. "i have this cuvette full of a solvent that can apparently dissolve my table. let's test if the lid leaks by trying above said table". Just the right amount of carelesness that paints you as a real human who isn't forced by some higher up lab person to do stuff as the protocol says. Thanks for your work, E&F!
im just here for the spiders mate
and I had the metal lid RIGHT THERE but no I had to test it over the paint - why did i do that
@@ExtractionsAndIre it's funny because it literally is paint stripper
@@Mister_Brown It's also delightfully carcinogenic, and absolutely stellar for smoothing and solvent welding PLA.
@@AlexanderTzalumen It’s still funny to me that I can buy cans of the stuff down at Bunnings lol. Useful as hell though but Christ distilling it S U C K S
Speaking as an electronics engineering tech, I have a weird amount of pride watching someone learn and build a simple circuit. This definitely made up for last episode, lmao.
haha yes redemption !!
@@ExtractionsAndIre I mean that resistor spider made me weep, but at least it didn't make cry out like yeeting a whole amp through an LED did
@@ExtractionsAndIre use a quartz vessel, glass absorbs UV
@@fss1704 He is.
@@Tunkkis i saw that later, forgot to delete the comment.
Ep 13 He is in my walls.... Ep14 turns out she was in my walls... now they are everywhere
Ep15 - Trying to kill the things in my walls with white phosphorus
@@RussellTeapot Ep16 - I’m going to The Hague! (not for a conference)
Ep 15 Drums in the deep - they are coming.
hey, lab assistants!
Lucky he a found a box of deadly, questionable pesticides....
Came for the chemistry, stayed for the curated Aphex Twin soundcloud dump playlist
this
@@adfaklsdjf he always does that for this side channel, its great
i love the victoria bitter in the background while synthesizing an explosive chemical. thats my aesthetic right there
Bikie chic
The real question being what's actually in that bottle.....
I started watching this because of organic chem in 1st semester, I am now about to start writing my bachelor's. How time flies
I started watching this channel at the beginning of my bachelor too, hoping that I would some day understand all the chemistry he's doing. I'm now in the process of writing my master's and I still have no fucking clue what's going on in this man's lab
yeah and im just starting my bachelors in chem and i've been following this for a few years now. Every now and then I get excited because I understood one thing or remembered a term :D
I love the "found footage from a meth lab" energy of this series
Using hot glue on heat sinks is probably one of the biggest DIY power moves, kudos. Also the new lab coat looks nice
it's an indicating adhesive, if it gets too hot it will melt the glue
@@Mister_Brown Thermal fuse, exactly!
I love the juxtaposition of buying expensive quartz containers for your food-can-and-hot-glue-and-archeological-relic-fridge photoreactor.
> hmmm how can I keep this cold?
> pulls out WW2 era fridge that is clearly home to 1000 redbacks
It’s certainly a solution
I feel like we're somehow watching the first channel able to rebroadcast after The Incident, streaming back in time from 2054.
So that’s what happened in the few days that turned into months in there.
the cataclysm has destroyed the concept of time during portal storms
DO NOT TALK ABOUT THE EVENT. They don't like it when you talk about the event!
@@sir_vixRemain indoors!
Hello, good evening and remain indoors! https://www.youtube.com/watch?v=wnd1jKcfBRE
Yeah bro, UV chem in the fridge. What a day to be alive
Hi I’m a Bachelor’s student in chemistry and over the summer I worked on some photochemistry stuff and last year got into a lab doing some cubane-like synthesis. As commented before, resulting to TLC is sometimes very difficult with these syntheses and if you can, I’d honestly recommend seeing if you could have your friend with access to the NMR do some characterization. Also! Please wrap your reagents and products in aluminum foil if they’re photoreactive. Most photochemical reactions are reversible and if you expose them to a continuous spectrum like white light, you’re just asking to undo your progress. Hope this helps.
Mate, if he hasn't wrapped in foil after two years. He ain't gonna wrap them. He's a PHD too.
he did mention in the video that he stores them in a place that doesn't receive light.
@@TheBoshy he's not a chemistry PHD tho, he did his in physics. He's a good chemist, but no where near PHD level.
Pretty sure NMR is out of question if he wants to keep this “out of my garage” theme going, hence why he’s sticking to TLC, unless he pulls out a rusty NMR machine from the university kerb. That said, would GC-MS be feasible? Pretty sure there are companies you can submit samples to for analysis (and to keep with the theme)?
@@ghindegaming2222 I have a feeling these molecules are too heavy for GC, but maybe normal phase LC could work. That's more expensive and specialized though.
Love when the fridge looks like it still uses banned refrigerant lol
That compound is a ketone, so it should give a spot with Brady's Reagent. Also' if your solvent is giving a spot then you should distil it. Maybe the manufacturer has added a stabilizer such as hydroquinone.
Ok great I’ll check it out!
And the solvent is fine by itself, but not after it has spent any time in the cuvette with the lid on
@@ExtractionsAndIre maybe try washing the cubette with some other solvents instead because they could potentially dissolve it better than the dcm.
Also try putting the stopper in some normal glassware and filling it with dcm before running the tlc on that dcm to determine if it really is the stopper.
I like this idea- probably the most low tech and solution to elegant solution to the visualization problem
@@Stalutes64 Perhaps it's not the stopper, but residue that's leached out of the teflon tape. If that's the case, removing the residue might be a possibility.
@@HammyJamPants in fairness if the stain isn’t working maybe the quartz glassware isn’t actually necessary and it just wasn’t being detected when using borosilicate ?
Watched the whole thing and loved it
speed run
24 minute video in less than a minute, time traveler confirmed
@@thom534 Time traveler or early access Patreon?
@@sammiller6631 way to make me expose myself as not being a patron
Not pHd level anything, but just a heads up on using the ir thermometer: the laser is deceptive because they actually read in a cone shape (the angle of which will be on the label), and in addition aluminium is relatively reflective. So when you're measuring the heatsink temperature with the gun, you're likely actually measuring the heatsink and maybe the a 50c coin area around it on the Milo tin (and that temperature will also be skewed to the temperature of the tabletop by reflection).
Yeah I feel that. But it mostly is there to try and prevent me from grabbing things to see if they are super hot or are room temp
@@ExtractionsAndIre didn't look like it lmao
@@crackedemerald4930 Tbf, he did write "try".
Yeah, this.. I'm saddened by the major caveats that come with these "laser" thermometers :( you can compensate for the cone/spread by moving it closer, but the emissivity issue foils me. Would marking it with a sharpie help? Piece of masking tape?
@@adfaklsdjf black electrical tape works pretty well
Netflix needs to upload this series at some point on their site.
There is an unmistakable correlation between the end of the academic year, and an increase in E&F videos...
I have so much confidence that I will bet someone money that Tom successfully synthesizes cubane before 2056. Any takers?
I think by 2043 it will be available in his nearest hardware store :)
Though it will soon get banned for being the nearest precursor to a very potent euphoric designer drugs family of cubane-propan-amines ;)
Its another Cubane episode, hype time boys!
1:55 "It wasnt very hard, I just didnt think about it properly"
Thats kind of what this channel is all about isnt it
From my mom, who is ABD in analytic photo-electro-chemistry, after watching:
"The quartz cuvette and buying cheap low quality materials... This is my phd omfg lol I can relate sooooo much!!!
Also, a uv-vis absorption detector had to be fairly cheap nowadays... HAS to be better than running endless TLC plates and trying to dye them???"
I crave the cubes! I'm so happy this series is continuing. Also that game cube into will never not have me in stitches.
Möthër, Ï crävë C Ü B Ë
As someone who’s made cubane, I find that recrystallizing the intermediate right before the UV cycloaddition is incredibly helpful. You can use UVA lamps for it (I think the key wavelength region for this reaction is 300-350 nm). I run this step in methanol with a slight amount of HCl (1 mL for 300 mL MeOH). You should start with a colorless solution and end up with a yellow solution that concentrates to an orange sludge if it works. Just need to blast it with photons. Tsanaktsidis has a great prep from 1997 in the Australian Journal of Chemistry
Gotta love the old Engel that looks like it's been at the bottom of the ocean for 30 years that still works perfectly
You couldn’t be more different from NileRed, yet you’re equally as fun to watch 😂
You couldn’t be more different from NileRed, E&I actually posts videos occasionally.
No. He's way better than NileRed
Nigel is a craftsman, Tom is an artist,
Old NileRed vids were a lot like this chemstry wise, he just went to normie chem after chem channels started being shut down by youtube (Rip ChemPlayer)
@@Kwazzaaap is Nurdrage still around?
Your soldering iron looks like it could burst into flames any second
Don't worry, the crust acts as a fire retardant
Looks pretty normal actually. Actually, soldering looks pretty good, at least at a glance. Clean(ish) tinned iron, good solder coverage, using what's needed not globby. Not bad for a filthy chemist!
Did you try Cerium Molybdate (Hanessian's Stain)? Works really well on things KMno4/ I2 wont spot. Heres a recipe: To 235 mL of distilled water was added 12 g of ammonium molybdate, 0.5
g of ceric ammonium molybdate, and 15 mL of concentrated sulfuric acid.
Holy shit, I hadn't been following the synth for a couple episodes, so I was catching up last night. Wake up to the first upload in 7 months and it's the next episode. Something, something, energy manifesting Aussie organic chemistry man slowly progressing towards very tiny cubes.
This is probably not the comment you're looking for, but as a multi-disciplinary nerd I can say that you have the best reality TV show ever. I am so hooked with all these cliff-hangers! :)
If you ever feel the need to upload to the other channel to blow off some steam (as it were), I'll be there for that too )
Light the Cubane cigars boys, the chemical kangeroo is back!
When I saw the latch on the fridge, my immediate thought was "must be to keep kangaroos out". Not sure how I feel about myself right now.
Watching you shake your fist in frustration not at the experiment itself but the failing methods of determining if the experiment is even working is either validating or relatable or both haha
9:18 slaps top of fridge You can fit so many Cubanes in this baby!
Suggestion: invite (Kidnap) Nilered and have him be your lab assistant. That way, if the synthesis continues to bedevil you, you can blame incompetent lab help for dodgy results.
I was literally just re-watching threw the cubane series last night. I love watching your videos keep up then great work.
I know everyone else is talking about the chemistry and the electronics-- but the music in the montage sequence absolutely slaps
the most anticipated sub par engineering video of the decade
This legit just made my day. Thank you, you chad genius.
god bless new cubane episode
@ExtractionsAndIre - 2022-12-18
Ok important question though: what are we calling the thing that lives in my walls?
@yavuzcelik3987 - 2022-12-18
Severe lack of medication
@Chlorate299 - 2022-12-18
A tasty snack.
@nissemartinsson - 2022-12-18
Johnathan
@robinderoos1166 - 2022-12-18
Quentin Tarrantino
@oliviamanifold129 - 2022-12-18
Martin