> chemistry > divers-organiques > cubane-chemistry > cubane-synthesis > a-slightly-new-cube-plan-cubane-ep-14-extractions-ire

A slightly new cube plan... Cubane Ep 14

Extractions&Ire - 2023-04-20

A short review of what’s going on, and a new plan for a path forward! 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

Youtube channels:

https://www.youtube.com/@UCqf4mbw0P0cmxZKWwV2Zqfw 
https://www.youtube.com/@UCdkzZNMT6AZ1GgazljwxV0Q 
https://www.youtube.com/@UCRi_rn0DUdbzYg8mHPX53kg 

Paper references:
Electron in a cube: Synthesis and characterization of perfluorocubane as an electron acceptor
https://www.science.org/doi/10.1126/science.abq0516

1-Azahomocubane
https://pubs.rsc.org/en/content/articlelanding/2023/sc/d3sc00001j

Benzophenone as a cheap and effective photosensitizer for the photocatalytic synthesis of dimethyl cubane-1,4-dicarboxylate
https://pubs.rsc.org/en/content/articlelanding/2023/ob/d3ob00231d

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

@callump6992 - 2023-04-20

7:51 that's me! Glad you liked the paper and if you have any questions feel free to ask away!

Also making cubane in flow has been done in a very nice paper before: DOI: 10.1055/s-0040-1705964

And also recommend a paper that just came out in Nature! by nobel prize winner David MacMillan 10.1038/s41586-023-06021-8

@grgr105 - 2023-04-20

And as always, we just randomly find the paper authors in the comments of an E&I/E&F video, why does this happen so often?

@Gamerzsociaty - 2023-04-20

​@@grgr105 because he is the crackpot scientist we all wish we could be

@notapplicable7292 - 2023-04-20

Pog

@NickiRusin - 2023-04-20

Absolutely poggers comment, thank you!

@resipsaloquitur13 - 2023-04-20

The cubane struggle is real.

@HeisenbergFam - 2023-04-20

2:38 you know its been long when this man has to rewatch his videos to remember what he did

@graealex - 2023-04-20

It wouldn't be so bad if reagents produced seven videos ago might not already have turned back into tar again.

@MazeFrame - 2023-04-20

Working in IT, reading what you documented (= scribbled on random bits of paper and in eight different documents and files) to get a grasp of the mess you left for your future self, perfectly normal.

@Puss1man - 2023-04-20

Heisenburger we have come across each other many times

@Ewr42 - 2023-04-21

​@@Puss1man I'm 100% sure they're a bot by now

Or they can watch videos on 4x, bc they comment way too fast to have watched the whole video in normal speed or even 2x

Caught that on the latest of John Oliver's last week tonight show video

But it's a cool bot, i like them

@jamesbrown9306 - 2023-05-17

​@@Ewr42 Agreed, I see it literally everywhere 😅

@johndeaux8815 - 2023-04-20

Ah yes, another episode of the cube series. I wonder if he is going to make one of the different cubes from That Chemists video.

@johndeaux8815 - 2023-04-20

I really hope this project works, I can only put so many stickers over the top of my Cubane 2020 bumper sticker

@jeffstaples347 - 2023-04-20

That video is the only reason this one exists and I'm here for it

@HerbaMachina - 2023-04-20

Seems suspiciously like That Chemist came and gave you a boot in the arse to release another cubane episode lol.

@ExtractionsAndIre - 2023-04-20

Haha yeah, it’s fun watching other people do cubane stuff, it was nice of him to mention this channel!

@WetDoggo - 2023-04-20

​​@@ExtractionsAndIre mate you can still beat him with huge quantities, using this:
Get at least one UV light Tube, enough PTFE tubing to cover the whole UV tube.
connect every other passing to aluminum or whatever metal pipes and place them in a waterbath.
cover the whole UV tube situation in aluminum foil and connect the pump.

that's literally all you need 😂
peak efficiency 😏👌

edit: oh and remember to turn on the lamp AND the pump 😂😅

@Diycrazystuff - 2023-04-20

​@@ExtractionsAndIre you should do something with erythritol tetranitrate it's an energetic

@HerbaMachina - 2023-04-20

@@ExtractionsAndIre I've been watching you for years, shortly after finding nerdrage which got me into the YouTube chemistry world. It's funny seeing everyone mention people I've been watching for a long time.

@WetDoggo - 2023-04-20

@@aryanprivilege9651 that is actually a good point... you won't see the majority of the light.
always wear eye protection when handling
invisible light... actually when handling ANY light of high intensity

@kaezaklimber3391 - 2023-04-20

this is like free psychological therapy for chemists whos been struggling with time delayed/low productive synthesis plans. "thank you" isnt enough <3

@LumirayYT - 2023-04-20

The cube race is on mate. Cubane this year ;)

@maxgarcia9829 - 2023-04-20

finish your thesis!

@ExtractionsAndIre - 2023-04-20

maybe

@cinderheart2720 - 2023-04-20

@@ExtractionsAndIre Start your thesis.

@firebry23 - 2023-05-10

​@ExtractionsAndIre no one cares about that piece of paper. What matters is how well you make things go boom or not go boom

@forestninjuh - 2023-06-04

​@@ExtractionsAndIre procrastination and chemistry seem to go hand in hand 😅

@GruenerGandalf - 2023-06-04

About cubane synthesis 😂😂

@mitchellblake1425 - 2023-04-20

i want some guys out there to just have the molecule tatted on his arm with all the different dates crossed out and replaced

@dec4dent - 2023-04-20

Will you accept a leg?

@mitchellblake1425 - 2023-04-20

@Josh Allen  I would but it would not be a good Tattoo so caution is advised 😂

@dec4dent - 2023-04-20

@@mitchellblake1425 I’ve got plenty of bad tattoos so don’t sweat that 😂

@harinarain09 - 2023-04-20

@@dec4dent dude u better show it if u do it

@restorer19 - 2023-04-20

Might have to plan for a full sleeve-chest-sleeve set...

@jospheyoung6150 - 2023-04-20

This series has been around more in my life then my family

@selkieblood4030 - 2023-04-20

I loved the part where he ripped off his labcoat and yelled "ITS CUBIN TIME"

@RealShebang - 2023-04-20

Exciting news!

It's just that I've been following this Cubane series for so long that I've forgotten what cubane is and why we'd want it in the first place. Everyone so often it pops up on my feed and I'm like, "Bloody criminey, Cubane! We're (maybe?) gonna need some of that when the zombies come!"

@thewuurm - 2023-04-21

Me, every time theres a new cubane video: "i dont know what hes doing or why, but the australian redneck chemist is very funny"

@Double_Vision - 2023-04-20

I'm just excited to be hanging out with all my fellow cube heads. Cube on brothers!

@briandavitmusic9421 - 2023-04-20

PRAISE THE cUBE

@Puss1man - 2023-04-20

I loved it when Extractions&Ire went "It's cubing time!!" and cubed all over the video

@sairassiili - 2023-04-20

@@Puss1man damn it, you beat me to the comment by three minutes!

@Double_Vision - 2023-04-20

CUBE! CUBE! CUBE!

@mowang1104 - 2023-04-20

That could mean something very different in a different context.

@YoutubeUser4756 - 2023-04-20

I just pulled an all-nighter doin an assignment and here I am watching this instead of sleeping. Perfect. Thank you very much for the upload!

@ExtractionsAndIre - 2023-04-21

Good luck with the assignment matteeee

@vexphoenix - 2023-04-20

I get unreasonably excited about every new E&I (and E&F) video even though I know next to nothing formally about Chem

@DrBunnyMedicinal - 2023-04-21

It's the suffering we all appreciate. Freely sharing such long-term frustration and suffering is always a great watch. 🤣

@robmorgan1214 - 2023-04-20

FWIW you have to be real careful with peristaltic pumps after a few hours the tubing can start to crack. Also the tube can lose its elasticity and start bulging instead of pumping this can cause additional problems with heating if your tube runs close to your light. This kind of thing will probably be worse in your application due to the uv light. Good luck!

@rdizzy1 - 2023-04-20

I don't think those tiny uv leds produce very much heat.

@robmorgan1214 - 2023-04-21

@@rdizzy1 depends on the volume of the fluid stuck in the tube and the absorption of the tube + sample. dT~k*a*W/cc.

@wildfyr89 - 2023-04-22

I think that is usually because they are getting mauled by the solvent, but perfluorinated ones are pretty resistant to this sort of thing.

@robmorgan1214 - 2023-06-04

@wildfyr89  I was using perfluorinated tubing in a UV environment. The thing was usually no good after 6hrs and would usually start cracking at 8-10 hrs.

@whitegold9453 - 2023-04-20

Finally, quality content back again on YT!

@daniellabunsky653 - 2023-04-20

Superb way to start my day! Cheers from a fellow Chemist/student and fan in California

@daniellabunsky653 - 2023-04-20

Been working with some weird photochemistry recently so I feeeel you pain 😂

@cvspvr - 2023-04-20

6:17 i'm genuinely impressed that you added a shadow to the text. reminds me of sovietwomble's glorious overediting

@ExtractionsAndIre - 2023-04-21

Oh I'm glad you noticed this! I've always wanted to do more shadow on text pop-ups but for whatever reason the editing software hates it... the render gets very slow and sometimes crashes, and the editing preview goes all jank around it so its hard to get the timing right. BUT I just bought 16 GB more RAM for my computer (turns out I had extra RAM slots woo) and now I can render shadows properly!! And that's basically the only improvement, the software still crashes occasionally. So it's a $70 shadow at the moment, but I think it's a worthy investment

@cvspvr - 2023-04-21

@@ExtractionsAndIre man, if shadows are too much for your editing software to handle, you probably need a different editing software rather than more ram. what editing software do you use? the shadow looked really nice though!

@ExtractionsAndIre - 2023-04-21

@@cvspvr I used Movie Studio, which is the cheap version of Sony Vegas. It handles multiple tracks of 4K footage playing at once and pretty much everything, but shadow on text??? It hates it

@cvspvr - 2023-04-21

@@ExtractionsAndIre i've never heard of movie studio but i've heard that sony vegas is pretty good. i've used adobe premiere (get a cracked version) before and it's pretty good. aside from the ram (which is heaps), is your pc... any good?

@nigeljohnson9820 - 2023-04-20

So impressed with the enthusiasm. There is a serious risk of making an original discovery in cubane chemistry in an amateur lab, all be it by a professional chemist. I feel sure Madame Curie would be proud of your efforts.

@Atlas-qu7er - 2023-04-20

im not convinced that scoop is a real science word, I think that's some deep seeded trauma from the ice cream episode

@defenestrated23 - 2023-04-20

"scoopula" (scoop spatula) is by far the best science word.

@Alexm920 - 2023-04-26

There are so many science videos on YouTube where everything just works, meanwhile your videos are the most accurate representation of the research experiences I had in grad school. Looking forward to seeing Cuban in 2023!

@Kithas - 2023-04-28

honestly the 'some aussie in a shed doing insanely advanced chemistry for the sole purpose of blowing things up' is the whole reason i watch.

@Alexander_Sannikov - 2023-04-20

a cubane chemistry video with absolutely no cubane or chemistry involved. love it, keep it up!

@mylesahead3698 - 2023-04-20

I would wear a cubane 2023 shirt if you made one.

@ExtractionsAndIre - 2023-04-20

Should I make the cubane or the shirts first??

@PrebleStreetRecords - 2023-04-20

@@ExtractionsAndIreShirts before dissertation/thesis?

@hunterringland5949 - 2023-04-20

​​​@@ExtractionsAndIrejust make the fucken square mate

@NoSaysJo - 2023-04-21

@@hunterringland5949 lmao

@bugdrvr - 2023-04-24

@@ExtractionsAndIre Just leave the space after 202 blank and we can fill it in after the series is done. Less pressure and more viewer interaction and all that jazz.

@Searage92 - 2023-04-21

I like this channel a lot because it's produced and you get places but things don't always work out and I feel like I can live through the trials and the methods and the successes and failures with you. Because the video series had gone on for so long it was a great idea to do an update on the world of Cubane episode like this.

@chillaxter13 - 2023-04-20

This has been such a ride... And I'm here for it! I vote that once you've created a sufficient amount of a precursor/reagent that you can then buy it for subsequent batches and it still counts.

@mrmax35 - 2023-04-20

Feeling real validated. Good luck Tom!

@doggodoggo3000 - 2023-04-27

I was hoping you would see that lol. Very heart warming.

@hamaljay - 2023-04-20

I'm so glad you're working on these videos rather than your PhD thesis.

@wildfyr89 - 2023-04-20

Tom DO IT UNDER INERT GAS!

Also, acetic acid and cyclohexane are both good solvents for radical bromination (classical for benzylic bromination with NBS), might be compatible with your photochemistry.

DCM obviously an easy one if you have it and they report 97% yield, but just saying as an alternative.

@thegingineer0 - 2023-04-20

Interesting to see FEP tubing mentioned. FEP film is used in the UV resin printers as the surface material since it offers a good blend of UV transmission and non-stick properties. More standard FDM printers use plain Teflon in their tubes.

@martinbridge7967 - 2023-04-20

I was literally going through your old cubane videos and....this appears? crazy

@alandonaly457 - 2023-04-20

I am really rooting for you to make progress on the cubane synthesis from household items. I am getting old and may not live to see you finish it. Good luck to you sir!

@Funkeyman - 2023-04-20

Always loving more cube videos

@covodex516 - 2023-04-20

#Cubane2023
I think the method with Benzophenone as photosensitizer looks very promising, it's definitely worth a try. Looking forward to your next vid!

@yorkshirechemist - 2023-04-20

personally if I were to attempt some photochemistry, the first thing I'd try would be to use one of those UVC germicidal bulbs inside a quartz tube fitted to a ground-glass neck, with the whole assembly inserted into the neck of the flask (you'd need a flask with a very wide neck); it'd eliminate the problem of trying to get the UV light through the glass (the UV is emitted from the inside out), and the glass would also block a lot of the UVC going out

@JohnnyWednesday - 2023-05-22

You may be forced to rely on the contents of the flask to wick heat away from the bulb assembly.

Stir the mix to dissipate the heat and cool the flask. Needs some fortuitous glass!

@yorkshirechemist - 2023-05-25

@@JohnnyWednesday with a neck that wide it'd be a bloody big flask in any case, and since photochemical reactions are run at very dilute concentrations, it'd contain a lot of solvent... but still, it'd do no harm to have an external coolant around the flask

@bigjay875 - 2023-04-20

Tom ol buddy, your a legend! Your projects have become known across the net far and wide👍☺️ keep up the good work buddy and good luck

@williambouthillier8611 - 2023-04-20

photo- AND continuous flow chemistry? Damn Tom you gettin fancy on us! Looking forward seeing some of that

@DrWitoz - 2023-04-20

CUBANE STRIKES AGAIN! Love to watch my favorite Aussie doing stuff in the shed :)

@ElSuperNova23 - 2023-04-20

Acetone also works as a photosensitizer, not as good but operationally simpler purification.

Also LIGMA-ALDRICH fucking slayed me.

@TWEEMASTER2000 - 2023-04-24

Love your videos, I wasn't able to goto school and have been a clandestine chemist, but I know very little compared to folks who've had a solid education. Your videos are inspiring me to go back to school, my best friend who was the educated chemist and taught me most everything I know ( him and youtube + google ) passed away in 2022 and I moved to Canada from America, and still sorting out paperwork for permanent residency with my wife.

Once I get my paperwork set up, my plans are get into a school, I was homeschooled and got a GED due to my family constantly moving and me working instead of going to school because of bad things that I can't really talk about.

You're an inspiration, and there are not many people like you on this planet and all your work is appreciated.

tldr; ty for keeping my passion for chemistry alive

@evanceremony7145 - 2023-04-20

I am sick but the fact that there’s a new cubane video cured me.

@SigEpBlue - 2023-04-20

I think it's great you're willing to taking a step back, figure out where to go from here. One thing I really hope you can do is VERIFY that the LEDs you've bought are actually emitting the wavelength(s) they should, before you go about using them. You say you'd need 390-nm UV, which is actually good, as the majority of mislabeled UV LEDs out there output UV-A (315 - 400 nm), since they're much cheaper than those that output shorter wavelengths.

@PhilmoreJenkins - 2023-04-20

Cubane with my morning oatmeal, lets gooooo

@mrdumbfellow927 - 2023-04-20

You need to give your graphic artist a raise. Video thumbnails are highly detailed and on point!!
You don't want to lose talent like that.

@SvetaFromUkraine - 2023-04-20

Exhausted all the previous cubane episodes not too long ago and was jonesing for another! Thank you Tom!!

@PedroDaGr8 - 2023-04-20

Ligma-Aldrich! Sums up my opinion of them pretty well.

@RhoGamingYT - 2023-04-20

The fact that this video came after the That Chemist Cubans tier list is insane

@bamischijf_2757 - 2023-04-20

I'm not a chemist at all, I do not understand what you are doing. But I live for this series every time a new video is up I gotta watch it right then, right now.

@Vithor.G16 - 2023-04-20

Let's go! Cubane in 2023!
We need this, man!

@owenbilling6612 - 2023-04-20

Wonderful to see you back at the Cubane, good sir!