Extractions&Ire - 2021-07-26
We build a UV reactor to try and blast enough UV to make our desired cage molecule, on our way to making cubane. But does it work? And how much time must we waste?? Subreddit: https://www.reddit.com/r/ExplosionsAndFire/ Join the Discord!! https://discord.gg/VR6Fz9g Twitter: https://twitter.com/Explosions_Fire Patreon: https://www.patreon.com/ExplosionsandFire Music is from the artist Arvid, with each track coming from the album 'Milk'. https://open.spotify.com/artist/6yPGvGC0PJZPdyaxi7xwoT Track names: - O - Interlude - Milk - A References: 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
The vaguely circular scrawl marking where the hole should be, the power tool waving menacingly yet impotently in its direction, the ineffectual hacking to try and actually remove material then the final step of getting your dad to do it because he somehow knows the right wizardry to make the tools do what you want.
I've never felt more seen lmao
My favorite reoccurring character, broken graduated cylinder, makes a cameo!!!
That’s awesome, but I would be afraid to use it, it must be very sharp
Hurts every time
My favorite recurring character is random wildlife.
I think we all have one broken in nearly exactly the same way...
LMFAO
I can't explain how excited I am that Land Down Under Man posted the tiny cube lighty shiney video
Mate he's a convict how often do you expect him to get online.
@CreatureOTNight COTN I don't think it's fair to call him a convict, it's just a PhD after all
This series has given me hope. Hope that one day I'll stumble upon someone who's inexorably caught up in a long, frustrating, befuddling project which repeatedly gives the illusion of having been completely in vain, so I can heartlessly comment...
*Laughs in Cubane.
I totally get you
Chris from clickspring says hi
*laughs in antikythera mechanism
"we're using uv light which is a bit of a safety concern" mate you're in Australia
but it's rainy week
@Extractions&Ire ah fuck right yall got the seasons upside down over there
@Extractions&Ire hey man whats up with the upload times? Early am intentionally or just when the vids done?
@Captain Lex thought I had about 10 minutes of editing left and it ended up taking me 5 hours. But I'm currently in lockdown so time doesn't really matter
@Extractions&Ire ah fun times, thanks for the videos as always!
Tom, usually not overly concerned with safety: yea I put the lamp in a box to shield me from uv
Me, with like 10 high output uvb tubes in my living room for my reptiles: oh... Oh...🙃
Glass blocks UVB really well, I don't think you have much of a safety concern
@SomeIrishKid I forget, but do the reptile lamps put out UVA? I know they output uvb obviously lol but not sure if they put out some uva that would add up with 10 lamps ya know. If they do then you do have stuff to worry about as glass does not block uva
@cwill212 ignore that deleted reply lol I was being dumb. Yeah you're right, that's worth looking into
@cwill212 Yes, they are usually even more UVA than UVB, like 3-4x more UVA.
You assume glass is involved, a fair assumption, but I mostly use mesh. It reduces uv output a fair bit but not nearly the same as glass
Honestly, the bulbs are never directly in my line of sight when I'm not fiddling in their cages, and they are all at least 10ft from where I sit. I think that limits any real risk of harm to an acceptable level(I'm also subscribing to the fast and loose method of health preservation we see tom display at times)
I exclusively use T5 HO arcadia tubes in curved reflectors. They have fairly moderate uva levels vs these garbage cfl units. They have a fairly fast(short?near??) output dropoff in uv which gives me some comfort(valid or not)
Water purifier UV lamps are super cheap and should be easily available. The circuitry for a regular fluorescent tube light will light it up okay. That should be plenty enough UV for your TLC as well as your π-π* transitions. Bromine cleavage might happen too, but may be worth a try. Also, a simple wooden screen is protection enough. The guys in my lab used this crazy water cooled high pressure mercury lamp for photochemistry in a wooden box.
Finally, copper sulfate is a convenient UV transmitting filter. And finally finally, your molecule might be a bit too non-polar for TLC in DCM. Perhaps consider 10% acetone in hexane?
That's UV-A; I think he wants UV-B, which is more of a tanning bed kinda lamp.
@Sebastian Ramadan No, they give UV-C and some other also.
@Sebastian Ramadan Tanning bed bulbs (They use a combination of bulbs to achive this) are almost entirely UVA, like over 90% UVA. Even reptile bulbs are mainly UVA also.
@Sebastian Ramadan emission peak is around 254 nm. It's what you use in TLC visualizers. With a filter it might be possible to block out the higher energy stuff without too much attenuation. Again, it's probably all about fun with jugaad.
@rdizzy1 he needs low UVA or high UVB. Tanning beds, and photography blacklight bulbs. philips suffix /09 and /08 and osram /79. The USA marking will be BL or BLB. You can also take a pyrex flask with a little bit of mercury in it and run ~500w through a tungsten filament inside. He has a vacuum pump to pump it down and adding a little heat he can adjust the pressure. aquarium stores sell little test cards that glow under specific wavelengths.
Two tips for you: No1 more Watts definitely help, No2 oxygen tends to be a pain in the arse in photochemistry so it often helps if you deoxygenate your solution (by bubbling inert gas through it for instance)
Glove box time?
"fast and loose" aka "I can't be arsed with it" lol
The precursor to yellow.
i get what i deserve
@Extractions&Ire To improve efficiency:
- spread out your product as much as possible (a big and level! glass plate)
- relocate the lamp outside on top of the lid > cut the hole in the lid big enough to not waste uv on exposed plastic and glue the reflector on. (Again, reflector completely outside the box)
- cover every last gap and any nonreflective surface with aluminum foil, since at the high reflective intensity even a little gap will waste a lot of light (think of how a laser works for example)
- maybe use less solvent... I don't know how much it absorbs your wavelength...
- maybe consider using a makeshift filter that only lets your wavelength through
I hope this was helpful mate 👌
Let’s play the game - yellow, tar, or yellow tar - place your bets!
@excited box Does it output the right wavelength? UV LEDs generally doesn't.
dOgBoGsY wOoFsAlOt you haven't watched any of his videos before, have you?
Yesss I finally caught a live one. Thanks for taking me back to my glory days as an organic chemist. Those sure were... times.
Healthy times?
@Extractions&Ire Only the freshest thiophosgene cookies in my lunchbox.
"We need to consider safety." drill bit flails around wildly
Another enjoyable cubane episode! I still vote for the nitrogen laser ;)
i could scream at the screen: SCISSORS man, SCISSORS
Got to admit when he said "we're going to use half of the monoketal" I started to sweat.
“I’m gonna need a ballast, and I don’t know what the fuck that even is.”
Story of my life.
Negative differential resistance is weird.
It's when you have a good meal a couple of hours before going out on the piss. A bit of ballast always helps.
A ballast is an inductor placed in series with the lamp which limits the current flow through the discharge tube to the manufacturers specification. Think of it as an AC resistance.
Your TLC is still far too polar, try using a petrol/DCM mixture.
+
I want to like your comment. But it's on 69 likes.
Maybe even a petrol/carbon tet mixture if its still too polar
And maybe a good drizzle of olive oil to finish
yeah I would guess around 10-20% DCM in hexane
Agreed… don’t know if ethanol fuel would work tho
Today on Explosions and Fire: Tom plays fast and loose, reaction mix gets a tan, and rain.
Top Gear theme sounds in the background
and birbs eating grass
@okuu True, should've mentioned the birds
extr+ire* :p
Wow, the production quality has risen. Love all the music filled shots.
the tlc bit was the best part of it. Loving this guy more and more, hes starting to put out some really good stuff.
Apparently my other chemist idol, nilered is just focusing on moving and doing shorts so this is like the best chemistry channel on youtube at the moment. <33
Anyone else really like the music choice in his videos? It has the garage chemistry vibe
I think it might be the glass, it looks like borosilicate glass is only about 20% transmissive in the regions you want. Might be even less with thicker walls.
yes quartz is best. but these bulbs are really low output in the lower UV already so it is no good.
you're reading the plots backward. it's transmittance not absorption. 3mm boro transmits 80% 320nm light. it's fine.
@Moist Apparently boro silicate can transmit up to 80% of 320nm light. However, it is dependant on the thickness and the composition of the glass. If you really want to know it, you have to test it.
DCM alone is often much too polar of an eluant for the type of molecules that you’re working with.
Life is not worth living when DCM doesn't work for something
I love that the "safety consideration" is an opaque plastic box with a hole drilled in it for the lamp. Just made me crack up. This channel is really a hidden gem
I was wondering for a solid two minutes what a "rectal" lamp was.
it's for the "enemahr"
rep-tull rather than rep-tile
@nibblrrr This comment is genius. Pure genius.
It's for shining light where the sun doesn't shine.
I was thinking a 5V computer fan could be mounted to your bin as a cooler so you could ventilate it better. just biff in a thermocouple with and if the temperature stays low/stable you can build some confidence in longer run times (though it’s a pretty safe rig)
Really I’m just commenting to feed the algorithm lol
That's a reasonable thought though!! (All hail the algorithm)
@Extractions&Ire yeah dude just let it run for two months if it works slow it's not like this series is in a hurry
Yeah building on this I made an exhaust for my resin 3D printer enclosure using two 140mm PC fans and a usb set up converter. Just snipped off the barrel jack, wired in a pc fan splitter, and boom both fans run at their rated speeds at 12V via usb. Things like $5 off eBay
An Aussie summer would laugh at you. An Aussie winter would chuckle and say theres snow else where.
Him checking on his reaction after an hour is very similar to checking your amazon packages every day even though amazon tells you when they arrive
Photochemistry: Hope that your 72 hours of UV exposure gives 45%.
I really like the way you filmed this episode, it feels like a real step up.
hey thanks!
It’s been one year, ten episodes, and a lot of chemistry and I still don’t really know what Cubane is or what it does or is used for. Yet I still keep coming back for more
It is exceedingly energy dense and given the right modifications makes for a rather nice superexplosive
@K T allegedly. Who knows if the reported properties of octanitrocubane are even accurate lol. Who has validated it?
Big boom molecule
The bonds are strained. The energy to force them in that position is large.
That means the energy that will be released when those bonds break during combustion is also high. Cubane is used in explosives.
<yelling into screen:> Quartz tube! Quartz tube! Put it in a quartz tube and it'll be done in six hours! Also, have you checked how uv-transparent your solvent is?
Personally I'd use a much smaller box for the lamp. You don't need to illuminate the entire box when all you want is for all the light to get into the tube, s shoebox would do.
But, you can probably engineer (lol) some kind of paraboluc reflector to go behind the testtube and really focus the light (more light = less time, ammiright?)
After spending the last 2 weeks binging everything you have on both channels, I’m SO excited to see new content in my feed! Hope the PhD/thesis is going well!!
Now that's what I call some scuffed photochemistry.
Idk if they are available in Australia but a UV water sterilizer would be fairly easily adapted for this. Different systems are designed differently but most of them are just a quartz tube that runs next to a UVC germicidal bulb. IT should come with both the bulb and ballast so the only modification you would need to do is plug both ends (with suitable plumbing fittings) and then you have a fairly nice UV reactor and with some research, you should be able to find different UV bulbs to swap out giving you different reaction condtions.
I love this series!
Some advice from a fellow chemist:
1. Photochemical reactions need some time. And with some time I mean a long time without any auxiliary substances. Especially with this low power lamp. I think u need way more patience.
2. Try using different solvents to develop the TLC. A standard system in our lab ist ethyl acetate:cyclohexane. It's way cheaper and better for the environment than DCM.
3. The staining solution looks quiet good. But try drying your TLC plate before using the staiining so it can soak in better.
4. I would use something to stir the reaction mixture. It might reduced formation of the byproduct - especially this dilution.
concentration of solute probably didn't matter because this reaction step was about an internal reaction within the monoketal, so diluting it if anything reduced side products
I'm pretty impressed with the progress you did manage to make holding those drilling and cutting tools with only your outstretched foot.
A source of UV that could work is the lights they use to set gel nails. They also come mounted in boxes similar to what you built, sold in drugstores, as part of a kit for doing your own nails. If it's the correct wavelength and power, you could use it unmodified on a cheap analog timer without too much fear of burning your lab down.
Are you doing the difficult bottleneck part fast and loose?
would you expect anything less from me?
@Extractions&Ire you make a good point, I guess that's what I'm here for.
For revelation, maybe you can use your long wave UV to reveal different spots as a "non destructive" revelator, note the spots and then reveal with KMO4 or if you have some elemental iodine on hand you can do the same with that and then reveal with KMNO4. That might help you differentiate between your unstaturated and your saturated ketone.
Procedure for Iodine revelation (https://www.chemistry.mcmaster.ca/adronov/resources/Stains_for_Developing_TLC_Plates.pdf):
A chamber may be assembled as follows: To 100 mL wide mouth jar (with cap) is added a piece of filter paper and few crystals of iodine. Iodine [...] will rapidly become saturated with iodine vapor. Insert your TLC plate and allow it to remain within the chamber until it develops a light brown color over the entire plate. Commonly, if your compound has an affinity for iodine, it will appear as a dark brown spot on a lighter brown background. Carefully remove the TLC plate at this point and gently circle the spots with a dull pencil.
As for the eluting solvant, DCM/Methanol mixture is way too polar for both your subtrate and product. I usually use it to elute polar stuff like hydroxyamides up to a maximum of 5% MeOH/95% DCM. More than 10% MeOH can dissolve the silica if thats whats on your tlc plates. Try mixing some DCM and alkanes/petroleum ethers.
This man is the reason why i still haven't dropped out of grad chemistry (not that i know anything worthwhile) always fun watching you Tom! Need more explosions and fire videos
You should do one on designing a molecule that can change colors when heated. An oil or a crystal or something. That'd be sick af.
I don't know what's funnier, the way you were trying to make a hole in the box or the fact you recorded that disaster lol
You're the budget James May, a man of the people.
Thanks Tom for keeping it real! This is how it goes, the pleasant struggle. Hard to find such entertainingly authentic content. Your channel is a refreshing spring in a lonely desert
Two things come to mind... A different geometry of reaction vessel to maximize the UV exposure while also allowing for stirring (how UV transparent is the solution?) and putting the reaction vessel as close to the lamp as you can without it getting too much heat.
This series has been keeping me alive
There's always carbon arc lamp, but I don't know if the wavelengths would be right. I think I remember you having a power supply that would work, and electrodes out of lantern batteries work great. Pretty easy way to get make your eyes go crispy levels of UV.
Easier to just buy a uv tube on eBay and not piss about with the heat and amperage problems of arcs
@moofy Oh definitely! I was shooting for cheap to free in a time frame of soon to immediately rather than any other concern. The more I think about it the more having a naked ark around all those solvents seems like a bad idea rather than merely a silly one.
Every time I hear TLC. I just think he's given the experiment "Tender Love and Care"
You could try a nail curing light. We use them to cure thermoplastic resin in our 3d prints
16:50 The virgin scientific peer review vs the chad "a few different people commented the same recipe"
Vs the sigma "i'm gonna go fast an loose"
Was anyone else expecting a portal to open up and a time traveler to jump out and stop Tom from plugging in that lamp like right at the last second?
I've got to admit I'm kinda bummed.
I am not a chemist, nor am I a particularly smart man. But all this is extremely interesting and entertaining. Love these channels.
Phriedah - 2021-07-26
This series has such "old youtube" energy and I love it so much
Charles Coulter - 2021-07-28
What I love about this channel and Cody's Lab
John Penguin - 2021-09-07
And his channel may be deleted any day...
Aboveground Garage - 2021-10-14
Just a clandestine chemist in his shed making explosive and flammable compounds
Joshua Kuehn - 2021-11-03
@Aboveground Garage SHHHHHHHH we cant use that E word here. it's really fast, uncontrolled nitrogen gas, or FUN gas, instead.