Cubane Ep 8 - Deprotection Time!
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- čas přidán 6. 02. 2021
- We battle spiders, stream commenters and the crushing pressure of time to deprotect a ketal group with DCM and HCl, closer to our cubane goal. Will TLC plates be our saviour? Subreddit: / explosionsandfire
Join the Discord!! / discord
Twitter: / explosions_fire
Patreon: / explosionsandfire
Music is as usual from the Aphex Twin soundcloud dump, track names are:
- 14 07 B
- 8LinmiriBradleyStryder
- taut
References: 1997 Lab scale paper: www.researchgate.net/publicat...
2013 Pilot Scale: pubs.acs.org/doi/abs/10.1021/...
"Cubane Derivatives for Propellant Applications" 1989
apps.dtic.mil/sti/pdfs/ADA210... - Věda a technologie
Yeah this is the last video before the break. It was meant to be done 2 weeks ago but yes, the chemistry hates to be rushed obviously
Thank you very much for posting it!
Thank you @Extractions&Ire
I've loved the videos on both of your channels, hope you have a blast in your time off. Looking forward to more funky chemistry videos in the future
Good luck with your PhD :)
omg I thought we'd already had the last one! Yay! Best of look on the thesis and defence and internship. Please please please don't stop teaching us about trash chemistry!
Cool, glad you’re still uploading some stuff last second, appreciate it Tom. Have fun on your furthermore physical educational endeavors. 😏👍
"I'm gonna deviate from that slightly" - it's going to go yellow, isn't it.
Don't say cursed shit like that
It wasn't yellow this time!!!! ....just tar
@@ExtractionsAndIre 🎉TAR!🎉
Tar is much preferred to y e l l o w
@@socalacura1338 Good ol'reliable Tar.
6:27 "They are disposable."
So are molecular sieves, but that hasn't stopped you from reusing them.
Haha this is a solid point, I wonder if I can somehow reuse the plates?? Surely not after the KMnO4 stain though
@@ExtractionsAndIre Maybe heat them until the samples decompose? Or some piranha solution?
@@necronomicon1472 i think piranha might work but also you might removed the UV stain tahts on them not like thats a problem if you are gonna use KMnO4, i know some physical chemist who boil some kind of silicaplate in refluxing ammonia preoxide and piranha for several hours. also if you wanna be super budge i would just run the plate in like 10% MeOH DCM if it was unstained and and re use it and ignore the massive line at the top you would build up
@@ExtractionsAndIre Reusing those plates and other supposedly non-reusebale things? Sounds like a good future video adventure after the break to me!
@@necronomicon1472 Sulfuric acid alone makes the silica fall off
Telling a big spider he’s not that big and to “leave mate” has gotta be the most Australian thing ever
It's just a window spider! Sure, they hurt a bit if they bite you, but they almost never do. It's not like it was a fuckin' redback!
Unfortunately while that's a flawless Spider strategy it doesn't work against the Emu's.
@@unherolike Yeah, but short of hitting the stupid things with a roadtrain, very little does.
@@DrBunnyMedicinal Oof, did *somebody* lose a war?
@@heh2393 Depends on who you listen to.
en.wikipedia.org/wiki/Emu_War
It's an internet meme that Australia lost to the Emus, but it's an odd kind of victory for the Emus, where they didn't get massacred by machine guns, only by farmers and professional shooters.
Meanwhile, one of the drivers in the machine-gunning attempt was mildly battered a bit when one of the idiot birds somehow managed to get it's head caught in the steering wheel whilst he was trying to drive it. Emus really aren't nearly as smart as they look.
Or as smart as the average stone, frequently.
I’m a micro/molecular biologist and I saw this channel: was like, “sounds cool”, several binge watching sessions later I’m like “I don’t understand a fucking thing that’s going on but this is fucking amazing!”
Genuinely thinking of doing some home brew microbiology shit in my shed because of this, maybe I’ll make an algae that sets itself on fire
Hell yeah, I don't understand biology but it sounds cool as
Pleaase yes, i would absolutely love it!
@@ExtractionsAndIre I'll let you know how it goes hahaha
Good luck with the PhD!
Keep us updated. Now that I pressed your subscribe button, I have a right to demand that.
@@Kenionatus hahahaha will do!
nice to see you haven't been yoinked away for a year. yet.
Only because I was slow to finish this video aw
I for one am excited to see tom's yanking. Yoinking? Idk.
@@NvrchFotia nice sentiment, but holy fuck could you have chosen any worse wording
@@q3st1on19 yeah that was the point
Be honest with us:
You are taking the brake to have the uni chem lab for a year for yourself, without distractions, to develop the worlds first yellow, tarry high explosive
"I'm going to deviate slightly" -> predict yellow disaster
As a fellow chemistry student, I will miss the chemistry you are doing on youtube. All the best to u!
Thanks mate!
@@ExtractionsAndIre wait how long is the break you're taking from youtube?
as a previously-high-school-level chemistry student, I second this sentiment
@@uxleumas czcams.com/video/dIYuk7XnLvA/video.html
he's still here!
Goodbye tho!!
I'm going back to school tomorrow, should prob get to sleep early
*video comes out* nevermind sleep, gotta find out if it goes yellow
Yes
Recipe for permanganate staining solution : in 300ml of water, add 3g of permanganate, 20g of potassium carbonate, and 5 ml of 5% NaOH. Stir well to dissolve, keep in a brown jar away from heat and the sun
(or the permanganate will break down)
(need to make fresh every 3-5 months or just filter the MnO2 and add more permanganate)
Ok, so there's a base element to it as well, didn't know this, thanks!
Your first try with the TLC plate I thought "That's a lot, but it might be okay?" and then you put MORE on it and I was like o.o
Hey Tom, finally something I can comment on!
Here are a few pointers if u wanna run this TLC again:
ur TLCs look like the spots were too concentrated. I think u could get a much better one by diluting down ur standard and rxn mix samples by 50% or more.
Also, hypodermic needles with the tip cut off using side cutters work really well to make nice, small TLC spots.
Anyway, I’m gonna really miss watching ur videos during your break! Good luck and cheers from the US!
I'm sure this is good advice, but it does my head in seeing it discussed in txt spk. :)
For the TLC plates there's an easy hack to get a nice spotter. Take a plastic pipette and stretch it out until part of it reaches elasticity, then pull until narrow, then snip. Kinda like you're making a glass ampuole except you want it not to close
Right I didn't know you could do that with the plastic ones, thanks!
@@ExtractionsAndIre I've only tried it with the skinny ones but the tip of the fat ones might work too.
Anyone else here that knows nothing about chemistry but still enjoys watch the mad scientist do his work?
5:23 Tom went "Ha. Ha. Ha."
10:58 that's a knob, you drew a knob and balls in profile on the plate
it has to be.
TLC plate so, TLC obviously stands for:
Time, Love and Care,
because you only do it when you actually give a shit about the outcome of your reaction.
- Extractions&Ire (2021)
Goes to my quote list together with NurdRages CRaP XD
Just curious, which NurdRage vid was that?
@@sebastianalmanza4756 Lab Notes: Failing to make Pyrimethamine in 2-steps
czcams.com/video/9RlhPtx38fw/video.html
"The tlc plates are single use"
They're single use if your lab is funded properly. If you let them chill in methanol for a day or two they'll show clean on uv lamp :)
Oh nvm, the permanganate will fuck it
This is a good tip though thanks!
@@nickcoradi5314 Mmyes, I love acetic acid :pp Very good tip, though!!
Been waiting for this. Thanks Tom for all the entertainment. Best of luck with the thesis and job! Will be looking forward to your return
TLC stands for time, love and care XD
Yeah looks like he needs some THICC layer chromatography.
Those long smears on the first TLC plate really bring me back to the good old days ❤
This process is becoming increasingly more mysterious and arcane... I absolutely love it! ❤️❤️❤️
That 3 km long needle gives me the literal worst feeling, take blood from one person and give it to another without ever removing the needle!
I think its probably a biopsy needle? That doesn't make the looking at it hurts any better though
I made the mistake of asking a med student what they’re used for. I really wish I hadn’t learned that :/
@@noisytim What are they usef for?
@@Ethelgiggle needle tasks
For extra extra Needle NOPE, search up Destin's (Smarter Everyday) video titled "Spiders and Priapism".
He talks to a Urologist about how they deal with the condition if it doesn't subside of its own accord...
*#LastUploadBeforeHiatus*
I play the carbon tet drinking game. Been sober for years, thanks for the reason to take a sip of whiskey.
10:13 The giant needle is likely for drawing fluids rather than dispensing them. I had something similar stuck between my hip and femur to check for bone infection.
Hell yeah that’s how I like my cubane reagents: deprotectected.
Also I’m sitting here perfectly happy watching this even though I watched the meta live stream filming of this episode 🤣
It's nice to see you doing tlc, since that is part of my bread and butter everyday! (Was a bit painful to watch though lol)
Yeah I gotta get better at it... But have to start somewhere!
yea that's true! As long as you can get the relevant information it did its job right
I'm commenting so the youtube algorithm helps your channel grow
Damn thanks for the heart. I still remember your old channel that got deleted, hope this one gets even bigger.
SO CLOSE, the needle TLC spotter is the friend of many research chemists. Usually from those long sterican needles you had but I preferred the highest gauge I could get my hands on. Cutting and filing the needle to a even, blunt end was a process that made you a legend if you did it for others. Same with grinding down broken nmr tubes to flat ends.
If you gently heat the pipette while pulling the tip you can stretch it out and make it way thinner. Works for hose too if you have 3/8" and you need 1/4" for example.
You have all these fancy solvents but can't get the label off a marmalade jar. I find acetone works well if water doesn't, or if you're impatient.
I used to work at a media monitoring agency where we recycled 1" Sony U-matic tapes for use as "temporary masters" when compiling advertisement reels.
As a lowly production assistant, part of my job was getting the old labels off the damn things.
For items that you can't soak in warm water, White Spirits (dry cleaning fluid) works a treat and it's less nasty than acetone.
Your videos convinced me that I can do more mundane chemistry at home without killing myself. If you're able to manage in a shed while the sun tries to murder you down in Australia I think I can manage in my backyard. Wish you the best
You know Tom, long experience has taught me the truth of "Let it sit, goes to shit" with synthesis. Just saying for next time you want to stop a reaction and let it hang out for a few days.
Yes, leaving reactions like this is not something I like to do.... hopefully when I'm back again, I'll have more time to do things in a day, rather than rushing off and having to come back a week later!
If you hold a disposable glas pipette above a torch and rapidly stretch the pipette when it is soft, you can make capillary tubes very easily and cheap. They are perfect to spot TLC plates!
Going to miss your chemistry exploits while you're away. Watching this channel makes me feel young again, I've not stepped foot in a chemistry lab for over twenty years! As for your TLC technique, please, get some spotters. You can make them yourself really easily with a thin glass tube and a propane torch, just heat the middle spinning it between your fingers and pull apart. You're permanganate solution should be much stronger too.
That seems like one hell of a difficult gig, particularly in small volumes?
Yeah the concentration seems very high, maybe because you need two phases to react with reach other? Usually don't run reactions at 1g/ml type concentrations
But what other option do you have, really? Not like you can start the whole process with large enough volumes to create several batches large enough for each step of the way. Well into the art of it at this scale. So many variables!!!!
During my Master's project we were forced to invent ways of spotting onto TLC plates because every organisation in England is poor. The best solution we found was to take a glass pipette, heat it with a blowtorch and pull it thin - kind of like making an ampule but you don't seal it of course. Each pipette makes two "spotting tools" if you "cut" the thin bit in half by snapping the glass. Best to make them by the batch cause they tend to break easy.
I think I would have eventually shelled out the $15 myself and gotten a 100 pack of spotting tubes 😊
I’m very sad :( see you in a year, my favorite Aussie chemist!
That last scene with the cans looks like a amazing success! Congratulations!
Little by little, Tom realizes his home lab is becoming a drug lab...
I mean, c'mon... needles... toilet paper... Depot "chemicals"... I hope he locks it every night before some "customers" start appearing
Long time listened, first time caller. Glad to see your channel going as it's going. Good for you for doing the good stuff
Science man is back
//shiftily posts another Cubane synthesis video//
"Gently spin it...and when i say gently spin imean excessive amounts of force"
😂😂😂😂😂
I facken love this guy😂😂😂
i know nothing about chemistry but i love this channel
Man you are one of the best science channels on the internet and most well researched chemistry
These videos always brighten my day! Your content will be missed in our feed but we know it is for the best. Thank you for putting so much into this channel and best of luck in your Ph.D! Your discord community will keep the science alive until you're ready to return
You're one of the best chemistry CZcamsrs out there and one of my favorite CZcamsrs period. Please come back some day!
At the lab I work at we use mason jars for TLC. Honestly that marmalade jar looks perfect to do TLC with.
That giant needle made my skin crawl.
Right!!
Your videos were the only lab experience I had for the first year my uni chem degree, thanks for being a bloody legend
*looks at second plate*
That's a nice product outline there
Man I'll miss this guy.
I wouldn't automatically assume those super long needles are for medical use (on humans anyway.) My lab uses long needles like that all the time for hazardous reagents that come in large bottles like acetyl chloride
Mid 40s where you are, mid -40s over here in canada lol
Learning for my organic chemistry exam just got delayed
Same here. I'm calling this close enough ;)
Ah you'll be fine, who needs to study
Hey Tom, I know I'm really late on this and maybe you've found a solution since then, but I always make really nice spotters for TLC by heating the thick part of a glass Pasteur pipette with a Bunsen burner (or any propane torch really) until it softens, and then quickly removing it from the flame and stretching out to arms' width. You can easily get 5 or 6 good spotters from each pipette once you get the hang of it!
see you space chemboy
Good luck over the break, we'll miss you!!
As an organic chemist I'd say good job on the TLC. Given what limited ressources you had to work with you deserve a gold star for getting any result. If only you hadn't already forgotten about the TLC plates by the end of the synthesis. It could tell you if the white stuff is the same as your starting material.
By the way cutting a syringe needle in half with a scissor is indeed how I do it in the lab. It yields a nice and small exit hole.
PS: That TLC joke was awesome. I'll steal it in the future
I did wonder "that's just a tiny little spider, why is he poking it with a stick?" Then I remembered; it's a tiny AUSTRALIAN spider. Something that size probably has enough venom to melt an elephant.
Yeah, Aussies are a tough bunch...
Gonna miss these videos. Can't wait for season 2! :D
Nice job! For TLC btw I like to use Melting Point Capillary tubes for spotting the plates; nice and tiny dots.
If you have a blow torch or a bunsen and some glass pipettes or glass tubing you can quite easily heat them up and draw them out into capillary TLC spotters.
The poor man's HPLC...I like
For TLC plate spotters you can make and use capillary tubes with a bunsen burner and glass pipette tips as they break very cleanly. It was part of our OChem Lab training.
Love your videos!! Thanks for sharing!
Last thing... You can make great tlc spotters by taking a glass Pasteur pipette heating it until quite soft over a bunsen burner then quickly drawing it out by yanking your hands in opposite directions. You be left with about a meter of very thin glass tube to break up. Takes a little practice to do right, but even a screw up gets you a few spotters.
Doug said he was going to be gone only for a little while......that was 3 years ago (3 days ago it was 3 years ago). Do what you gotta do on your break but honestly, make a video here and there to let some of your followers know you're good. We would appreciate it.
I feel exactly the same way yeah, it's strange not having any updates so I will do so
@@ExtractionsAndIre Even a few minutes having a rant or waffling on about nothing over a pint would be cool. Good luck Thom!! Do big things!!
Protip for anyone who only has Pasteur pipettes and needs to add teeny tiny drops to something like a TLC plate.
Dip the tip of the pipette into your solution but do not aspirate any fluid into the pipette. If you play around with capillary action and general van der Waals forces, you can get a tiny droplet on the end of the pipette tip that is 1/4 the size of the smallest droplet you could normally expel from this type of pipette.
Alternatively, use the classic undergrad method of glass pipettes.
I think your use of TLC plates went well! I used them a few years ago during research. Glass pipette tips work best for plate application. You don't even need to press that hard, the liquids usually absorb themselves onto the plate with little effort.
The Prophecy was true. The return is upon us.
It's hard to leave!!
Tip for TLC spotting:
Take a cheap soda-glass (open ended) glass capillary tube (I don't actually know what they are normally used for in microscopy, but sold by the hundred), heat it in a Bunsen flame, and draw it out when the glass softens. You can then break in the middle and snap off the end to leave the almost perfect TLC-spotting device Well, two of them, actually. It takes a little practice to get it right, but I've used these literally thousands of times in an industrial setting.
Alternatively, you can just buy different sized ones from the you-know-who Chemical Company (I worked for a competitor).
I rolled my eyes when you said a big fuck off spider, then I saw the thing...yup that's a big fuck off spider.
glass capillary tubes + blow torch = two perfect TLC spotters per capillary tube :)
You can easily make your own TLC spotters if you have some disposable glass pipettes and a good torch or Bunsen burner.
Yes! ...which I didn't, but I should get some
Would it be inappropriate to say this video was very boss gangster? No.
This video was very boss gangster!
Usually you can pull on the end of those plastic pipettes and stretch it out thin, if you really don't want to get any capillaries....
Glad to see you're still at it!
Heating at the same time or just putting a lot of force into it?
@@ExtractionsAndIre for glass ones, you soften the middle part of a pasteur pipet using a torch until you feel it get a little gooey, then pull it out. takes some experimentation but you can get a nice reusable TLC spotter provided you rinse the tip with solvent between uses
@@ExtractionsAndIre Just putting some force into it was enough when I did this in a school lab a few years ago. Like Samuel said it's pretty easy from Pasteur pipettes if you have some. Once it's good and soft you just have to pull really quickly.
Miss you already!!! Wish you the best on your break from your loyal fans!!
Thank you!!!
Great video Tom, we will miss you a lot! Didn't see a coment about it, but you could mix DCM and hexane in a 9:1 ratio to lower the polarity of the solvent and maybe get a better separation. Anyways, what you do here is awersome and I hope that you PhD goes really well!
The TLC bit was the funniest thing I have ever seen. The polarity of the product is still very similar to the reactant as you are only deprotecting half of it. I wouldn't expect the Rf to change that much. Spotting those strips though 😂😂😂
If you were the beautiful bastard who proposed “fulminating spider” in the live stream chat, know that I am still laughing at that.
Hell yeah it's TLC time! Love a good TLC. Reminds me of the scuffed kinetics test I did for advanced integrated II
Good luck on your 'break' mate! I look forward to seeing you come back with those bloody hard earned three letters after your name
Good luck with stuff mate. We love you and wish you the best. We will miss you
that intro was truelly top tier!
I'm surprised we're still alive, when I was young, every machine shop had buckets of Carbon tet just sitting around for degreasing parts, dry cleaners had the distinct smell of CCl4 ( that's why it was called dry cleaning fluid) and you could buy it at any paint/hardware store.
We used it as a contact cleaner for electrical contactors, nothing works as well today.
I am definitely going to miss your uploads. Best of luck mate!
Also, the "impurity" that helps the reaction progress forward is the ethylene glycol that is generated. Ethylene glycol works as a (somewhat shit) phase transfer catalyst. I only say this because I learned the hard way. I once had ethylene glycol in my reaction mixture in grad school and during a DCM/aqueous workup, I got an inseparable emulsion. That was a bad day in lab.
Good luck on your endeavors, m8. Look forward to seeing you after the break.
Spray bottles are great for coloring TLC plates, just spray on before using hair drier. If you have more polar substances you may not want to dip them in liquids.
You are really overloading the plates. A blunt small needle could work as a substitute for a capillary tube. You can also make capillary tubes by pulling some glass pipettes if you have any. Pulls so easy with a torch and cuts with a bend.
Man im gonna miss seeing your videos. I have a basic understanding of chemistry and a fair bit goes over my head, but ill be damned if I don't watch the whole thing anyway haha. Best of luck to you man, I know we'll all be eagerly waiting for the next post.
Oldie here. We used to use carbon tetrachloride as stain remover with no thought for dangers. I think it was used in large volumes by the Dry Cleaners too!
Still got all ten fingers and toes. The dark forces you're working for must be pleased with your results.
Enjoy your CZcams vacation. Can't wait to see you back. Smooches
that spider was almost as gross as the drawer it was in :P
It's a goddamn gross draw. Draws are made for cupboards, not to be lying on the ground
I once had an injection in my hip (into the joint) for which they used a 120mm long needle, that's the kind of stuff they need really long needles for
ow
I know I'm late to the game, and someone else might have said this, but you can make ghetto capillary tubes for TLC spotting by heating glass pipettes with a blow torch in one spot, and then pulling the two ends apart. Then you can just break the very tip to make a small opening, and voila! (You can also kinda do the same with plastic pipettes if you're careful, but it doesn't work nearly as well)
Suggested alternative title: Man in His Shed Full of Spiders Attempts Chemistry