Extractions&Ire - 2022-03-20
We set out to improve every aspect of the UV photoreactor, which is proving a pain in our journey to cubane from the hardware store. But will it be enough? 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: all Aphex Twin soundcloud tracks. Sorry once again to people who have sent me cool music, I am too short of time and it sucks. 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
No matter how this video ends, know that we love you.
Thank you for the support , it's needed haha
@Extractions&Ire love and support mate, idk how much you need to hear it bit lately I've just been wondering "how's Tom, I bet he's gonna upload any minute now, I hope he's ok and didnt snort carbon tet"
💗
that we do!
@Extractions&Ire If it makes you feel any better, I'm always super excited when I see a new video posted.
Big beard Tom shaking from excess coffee and struggling to open a jar is textbook PhD student (also, relatable)
Is it weird that I'm attracted to fields that require steady hands (electronics, microbiology) despite my crippling caffeine addiction?
So brave. Many chemists are scared of the enema tests, despite their accuracy and helpfulness. I'm glad that you were not only keen to have an enema, but respected its outcomes.
I knew I wasn't the only one hearing enema, lmao I was like holy shit this guy's committed.
“hydrocarbon liquid” sure does narrow down what it might possibly be!
Be specific Bob!
Could be gasoline
Could be cooking oil
Is it lighter fluid or is it bunker fuel? Finding out is all the fun!
Petroleum distillate lootbox
methyl ethyl ketone. It always seems to be MEK
Have you tested it for gold? There's a non-zero chance you've unlocked the secrets of alchemy.
"We are ignoring the passing of time." Words to live by
10 days man. It seemed like he was on track until he abandoned it for that long. If he just kept going, he probably could of got it. he could at least kind of fold the tin foil better around it for reflection.
100%
"Men talk of killing time, while time quietly kills them." - Dion Boucicault
Don't forget the classic "It could be worse."
here he talks about not going over budget and getting stuff out of the hardware store then he goes out and buys "space age bricks" those must have cost you a fortune.
That’s what credit cards are for
@Rado he payed using a "space age" credit card
Maybe hes got a real good brick plug...
@Ok Ok Fuck I laughed more than any sane person should at that. Then looked at the strange firebrick shortages and rationing and...
He used that color changing credit card to buy them.
I was doing UV-Synthesis at Uni, and for a 250 mg scale used 1 L of solvent. I think this is generally also how UV Reactions are done. You dilute your reactant quite alot to avoid unnessesarry side reactions of the radicals etc. . Also maybe degass the Solvent beforehand somehow, which would remove dissolved oxygen. Loving this series very much!!!
Bubbling nitrogen/argon through the mixture should do the trick
@Broklond Ideally with a solvent this volatile (DCM) you want to do freeze pump thaw, I think.
I was thinking similarly that oxidation is probably adding a lot of emotional stress to this process.
This is good advice. I would recommend ultrasonic degassing specifically to remove dissolved gasses from the DCM, just not certain how that would be best achieved with the "hardware store" restriction. Perhaps purchasing a cheap handheld ultrasonic vibration grinder and running that for ages, or rigging up a speaker to vibrate at 500kHz or so and placing the solvent container on that.
@Syntactyx pretty sure he has a ultrasound cleaner, he just hates the noise it makes
I know the feeling of having tests ruined by a "sterile" plastic syringe. Took us a couple days to figure out the problem.
@HammerTh Honestly there should be a public Name and Shame for these companies so the rest of us can stop wasting money
That is not something you want the label to lie about
unfortunately sterile just means there's no live organisms in it. you can run dirt through an autoclave or a gamma irradiator and it will be sterile.
I'm getting too emotionally invested in this. The last part of the video was difficult to watch.
let me do a tldr of things which would help Form product:
1) dilute heavily (<1g/L)
2) stir
3) purge with argon/nitrogen
4) one-shot the reaction (do not let sit for days on end)
5) consider checking pH of DCM, some acids may be left, add K2CO3 to the bottle to react any leftover acids from Industrial synthesis.
6) stronger lights... More reptile lamp lol
7) quartz reaction vessel
That's all I got!
Paint the desk a faint yellow so all of your products look good!
Oh no
the problem with painting the room the colour of failure is that you're surrounded by failure
@CATASTEROID but everything you make is a relative, good colour
ha! yes!
by comparison?
"But somehow the months went past"
I felt that on a deeper level lol. Wasn't it August 2020 just a week ago?
Wait, wasn't it 2019 just a few months ago?
Yeah my lord what is going on man
I still cannot fucking believe 2020 was 2 years ago
Nah, pretty sure it was "just two weeks".
Ah fuck me what is time?
I'm just a truck driver so my knowledge of anything science related above like a high school level doesn't really exist but even with me not understanding half the stuff you're talking about I still love watching your videos. For what it's worth i'm rooting for you to nail this project
Truck drivers make the world go around we can live without all chemistry but we cant live without truck drivers
@Randal Loshbough that's a nice sentiment but not nearly as true as you think. There's no trucks without chemists and a lot less to deliver without them too. Every worker is an important and valuable member of a society.
@Randal Loshbough chemists invented most of the materials to make those cars. From metallurgy to vulcanized rubber and early plastics.
Hey I'm a dumb truck driver too
Have you considered using a VB (longneck) as TLC solvent?
I own a bearded dragon. Using a linear reptile light might produce more intense UV light.
I had a customer that could tell which route (2 possible roads) the FedEx or UPS truck took to his lab. One was paved and had minimal metal contamination in his polyethylene digestion tubes and the gravel road had tungsten and cobalt in the tubes.
We had to bag his tubes specially and give the courier specific driving directions. He always knew when they had ignored the instructions.
whaa .. I am just curious, but whaaat? How much contaminants get into a regular postal package and inside the factory package of the goods? What is his process, that has such high sensitivity? And how did he find out - I guess he had to find out such small contaminants out of necessity? Sounds like funny story.
@Stoyan Petkov He was using ICP/MS with a quadrupole mass spec detector. He used our digestion tubes because they were the cleanest available.
To check the cleanliness, he do a 21 day soak of the tubes in ~10% HNO3 with a bit of perchloric acid too. He’d regularly find less than 10 ppt - parts per trillion - of a couple of random but consistent metals - possibley boron and a radioactive heavy metals, I can’t remember.
The boxes had 100 tubes. We specially packed 10 x 10 tube bags in our clean room. Then we packed those bags inside a larger sealed bag. The boxes were then sealed with packing tape including all edges.
He’d find 10-ish ppb of copper and 5-ish ppb of another metal - maybe aluminum - only if the delivery driver drove on the gravel road. Asphalt road were always at background.
Crazy but true.
@Dave Belyea I wonder if it was due to dust accumulating on the outside of the packaging so that when each subsequent seal was broken some contaminant got inside the next layer in.
Might have solved his issue to pack in a water or other solvent proof container and then do a thorough washing before opening anything.
It doesn't make sense that gravel dust would be penetrating through all the seals.
@Dave Belyea Reminds of when I read about the watt balance problem.
they discovered that the ultra precise reference calibrate resistor would go out of calibration every time they took up stair to place in the machine.
yes, the paper suggests they did this song and dance on going to calibrator going upstairs finding out the resistor is out of calibration a bunch of times.
and search for the reference, I found none except the Wikipedia entry that has a direct quote as citation: "R. Steiner, No FG-5?, NIST, Nov 30, 2007. "We rotate between about 4 resistance standards, transferring from the calibration lab to my lab every 2–6 weeks. Resistors do not transfer well, and sometimes shift at each transfer by 10 ppb or more.""
also, it is a hall not stairs.
@youkofoxy now I’m going to look that up… 🤦♂️
Great to see you again!
Definitely, rid of oxygen. Photooxidation is one reaction I did in past, and with this setup and UV I am surprised that TLC looked SO GOOD. Argon/nitrogen all the way together with a balloon for positive pressure and well deoxygenated DCM. As for reaction, time to take example from academic chemistry, setup the reaction in the evening and run it overnight (~12-18 hours). If this won't work then it is fault of Reptilian lamps XD
Another problem can be reaction overheating, most of the photochemistry is made at lower temperatures just to push photo over all reaction made by heat. Check with a vial of water and thermometer what is the temperature inside after some time. I remember the need for 0°C over reaction run in my past, don't know what were temp ranges in cubane paper you are using
Still, fingers crossed for you! This would be the most priceless cube, carbon cube!
Helpful, thanks mate!
@Extractions&Ire You are welcome!
For iodine chamber, if you can use smallest possible jar, you can heat it before use for more vapours and better visibility on TLC. I personally mix some iodine with gravity column chromatography silica. It deosits on it and then you can dip plate in this siica and iodine transfers direct from silica to silica. Great for lazy people XD
Maybe good idea would be stain typical for ketones like 2,4-dinitrophenylhydrazine based one? It should work pretty well in your case (if you have it of course :P) or p-anisaldehyde (this one works on crapload of compounds with nice colours on plate).
@ejkozan I wonder if you could replace the para anisaldehyde with pure vanillin ?
I know what you mean. After awhile you just start purging everything and wrapping everything in foil.
Also, never leave anything in solution. I can guarantee you'll see more of the pretty yellow baseline polymers from oxidation if you do :D
I feel like once youve proven that youve synthesized something, You can feel fine about taking the shortcut and buying directly, ie: the dcm.
It's more expensive I'm in the US and miss the hardware store DCM goop
It's like unlocking the tech tree.
Not at all. Messed up purity, requiring high quantity -- factors you will miss if you just buy.
You mean directly buying the tar? 🙂
I agree. For the sake of getting this series done, I'm fine with buying more advanced pre-cursors rather than going through the previous 5 reaction steps again to get more monoketal
Few suggestions:
1) You need to be using MUCH more solvent for photochemical reactions. (Alternatively much less of the compound or better yet, both.)
2) You still may be producing a minute amount of product but it may have similar enough eluting speed to look like one dot. I would recommend using less polar mixture (maybe 5% acetone) and run the TLC plate multiple times (run it -> dry it -> run it again -> dry it etc. maybe 2 or 3 times). Or alternatively you could try a 2D technique though I never had much luck with that.
3) Ditch the sketchy reptile lamps as they produce way too much heat. Sometimes we even cool our solutions for photochemistry so there is a lower probability of deexcitation due to solvent interactions.
4) Flush your reaction vessel with argon, I know you have a cylinder of it laying in the shed.
The first point is a good idea, also because by diluting the compound you enhance the chances to trigger an intramolecular reaction. Less molecules around, less cross-reactivity, less tar.
Didn't he use up all the Argon when he was making anhydrous Peroxide? Or did he get more?
@Scott Was Here watch the last minute of this video
@Scott Was Here if hes already got the cylinder, it costs maybe $40 to refill it.
boosting
I have a rudimentary PhD in Chemical Engineering and I am flabbergasted as to how an enema can be of any use in determining molecular structure in your sample.
Absolutely flummoxed at the moment (and I have a beard)
Oh man, that NOSY COSY HMBC etc stuff is hardcore. Way beyond me
You just havebt tried it yet ;P
@Extractions&Ire Wait a minute, we learned that in the 5th semester of the Bachelor. It was a pain, but really interesting.
It’s all about where it tingles and how hard 😜
This reminds me of when I was using a plastic syringe for filling liquid IR cells and the beaker I used for the DCM would go cloudy and we were convinced there was an impurity in the DCM, until we realised I left the syringe in the beaker so the DCM was just decomposing the plastic XD.
thats what i assume happened with his eppendorf tubes too, like i dont know why he didnt cringe when using dcm with any plastic container not specifically made for dcm use
We love your tar videos, we learn a lot about what is tar, where you can find it, how it's forming,... it's amazing... even under uv light! No, seriously, i can understand your frustration... hopefully the next video you suceed!
At this point he should consider writing a thesis on tar.
Ah yes, the good old tar. I hate it.
I did an experiment in the University a while back and suddenly everything was tar/dark yellow gue. But it seemed like the reaction had worked and after a nightmareish extraction I got an acceptable yield ^^
9:38 "I'm glad I'm not tryna do surgery or careful alignment right now"
Proceeds to use power tools to make airholes in the very next scene 🤣
Use a Vanillin stain, it produces different colours for different materials (mostly), and it smells like cookies!
Found your channel a few months ago and have now binged through all the vids! Absolutely amazing stuff!
My family are glassblowers, we use a bunch of different chemicals and minerals for adjusting the colours/ properties of the glass.
As so we have like 20kgs of Cobalt carbonate and a bunch of other random odds and ends + glassware, all yours if you have a need or want for it as we don't need it anymore.
:)
Theres something about watching someone try to open a jar I just get a overwhelming need to insert myself into things and ask "let me have a shot" in classic strongman fashion
You're just based, dw
You could also just give the wise-ass I'm smarter than you answer in the comments.
Just switch hands. When you use your left hand on the lid, your thumb will "cam on" and lock your grip even tighter the harder you twist, like an old school drum brake. Trying to turn counter-clockwise with your right hand does the opposite and works against the geometry of your thumb. It's why it's so easy to over tighten lids and they always seem to stick on harder than you remember. It's just that your grip is stronger in one direction.
Evi1 M4chine You mean a blunt chisel?
@West Coast Wheelman I'm both handed and I felt like opening jars was a lot easier with my left hand. The leverage of the forearm can be used much easier with the left hand as well.
Use a can/bottle opener to prize up the lid. Breaks the seal and let's it open easily.
You may damage the lid
This project started before i began on my chemistry degree and it's probably gonna finish after it
Don't give up, Tom! I've been watching this whole series and still don't know what the fuck you're even doing, but just know, I BELIEVE IN YOU.
finally another episode of this legendary series
As I think others have pointed out, a cheap OTC source for quartz tubes are UV water sterilizers. They come in open type and closed-end type, like a long test tube.
Yeah I started looking up quarts vials and those are crazy expensive. But saw those tube you were talking about and they are pretty cheap. Though the ones I found at first were just open on both ends. I was thinking it cant be too hard to seal the ends. Then I saw your comment and saw that they do make them with a sealed end. But in my limited search they were like 300mm long. Still that a managable size and with some digging can probably find a shorter one.
@GMC Labs I believe it was your comment I saw back then. Check out US based Mountain Glass, they actually have decent prices for quartz.
Going from trying to figure out where the impurity is coming from, to earning the impurity wasn't from the solvent and was actually from the tubes gave me emotional whiplash.
I don't think ive ever been more excited watching a video than seeing that the bottom dot was getting bigger while the top dot was getting smaller, showing it converting.
Edit: Finishing the video, i've never been more disappointed than seeing that nothing mattered, it was all shit, i got excited for nothing.
But I'm still excited to see you do more. I love this series. And after this one is finished, i still think it'd be crazy cool to see you do more chemistry like this, especially after the fact that you made such a pure compound the first go. You're pushing bounds for the home chemist and I love it.
same, until it was just the impurity from the plastic tube
I've been going through a really rough time lately, and it gives me so much real joy to see a new video from you in my feed
Hope things get better for you. I also hope things get better for Tom though. Endless fighting for no reward is tough...
Just go kidnap NileGreen and make him babysit your lamps, ez.
Good luck tho Tom, really enjoying following this series
Cube Chem, YES ! Since that hamilton morris crossover I've been even more invested. Its awesome chem.
Heartbreaking : ( You'll get it with persistence though. BTW, congratulations on your almost completed PhD!
I did my PhD in Organic Synthesis. I would recommend you use a VERY dilute solution for your reaction vessel. The reaction you are trying to do is intramolecular so you want each molecule to be nearly isolated compared to the other molecules around it. This will promote the intramolecular ring closure and prevent other side reactions/polymerizations that are probably occurring.
Best of luck! Love your videos!
I see Cubane, I click the video. Simple as.
EDIT: You doubling down on the reptile lamp is amazing. Live your truth, king.
Yes, another cubane vid! Well done for continuing to hammer on this Herculian task, regardless of how the video turns out.
Tom, I am very pleased to see this episode. It has been too long. Get that PhD done. We need yellow tar researchers!
the production quality just keeps going up... love it! new cameras showing
HD tar
Absolutely love both this channel and your slightly more explosive channel. Always makes me wish i could do this until I realise I could if I had money and time to waste haha. You do a very good job of making chemistry accessible with a heavy emphasis on do as I say and not as I do 😉 Stay safe out there ❤
Best part of Tom uploading is it means he hasn't blown himself up yet 😂 I was getting worried there mate!
Hey, I'll stick around for however many cubane episodes you want to make. It's very interesting
As a great chemis once said: "the greatest skill you can have as a chemist is the ability to hold a good grudge"! Never give up
hahaha loved that end bit with Cody heating the lid with a blow torch, and you just smashing the jar.
Praise be to home chemistry man. He inspires the masses to pursue true (non yellow) chemistry
it's good to see you again, cube magician
"there's nothing but tar and starting material here" -- words to live by, love your content
Hamilton Morris - 2022-03-21
Never give up
uzbekistan playstaion 4 BIOS crék 100% W0rking - 2022-03-21
The legend himself
That Chemist (old) - 2022-03-21
you two are legends
Aaron Clair - 2022-03-21
wow thanks Drug Dad
Wet Doggo - 2022-03-21
... was about to comment something about legends and stuff, but nevermind... I'll just agree with never give up Splosionsnfire
GermanMythbuster - 2022-03-21
never gonna give you up,
never gonna let you down
He got rick rolled by the synthesis 😂😂