Extractions&Ire - 2020-08-09
We crack out the Dean Stark trap to react ethylene glycol with cyclopentanone, in the next step in our hunt for cubane! Links::: Subreddit: https://www.reddit.com/r/ExplosionsAndFire/ Twitter: https://twitter.com/Explosions_Fire Patreon: https://www.patreon.com/ExplosionsandFire Join the Discord!! https://discord.gg/VR6Fz9g Paper we are following: https://www.researchgate.net/publication/244572672_Dimethyl_Cubane-14-dicarboxylate_A_Practical_Laboratory_Scale_Synthesis Music is as usual from the Aphex Twin soundcloud dump, track names are: - 15 Autumn Travels - 18 1974 94 [8 concentration mix] - 19 Ssnb
“I never know if I’m overthinking, underthinking, or thinking just the right amount”
That sounds familiar.
thats deep
"thinking"
I need to have that tattooed on my body. lol
I think it's possible to think just the right amount. Or perhaps not thinking the right amount, Is thinking the right amount and it's the people making us think more that should think less, and concurrently, ergo vis a vis, it is ourselves also that should think less, about thinking more, therefore avoiding the inherent anomaly.
10% product yield,
550% tar yield.
It completely broke me, when you put in the “going yellow” speedrun overlay. In tears
@Extractions&Ire Only way you're gonna beat this record is to actually start with a yellow chemical haha
@Extractions&Ire Not gonna lie, on the first part of the project I was left thinking "this shit can't go yellow there's just nothing in it that looks like it could turn yellow" and here we are now. Btw I'll take the bet and go for a 5% yield, cause goddamn that doesn't look the product you'd want to see after the whole reaction.
Look at the stars, look how they shine for you
@Extractions&Ire i called it
yellow% WR
Absolutely dry and pure yield: 15%.
Crude yield obtained by weighing the product after 'good-enough' purification, before moving on to the next step: 25%.
You know me too well!
@ClickThisToSubscribe ; Hehe, it kind of reads like a YouTube video title, but you forgot the Holy Grail: We report the facile synthesis of a novel compound in a One-Pot, stereoselective procedure", according to green-chemistry principles with an atom economy above 0.99. XD
It amuses me that he pronounced "toluene" like 10 different ways
haha that way i'm guaranteed to at least get it right once
81%
Naive? No. In chem class, we frequently got over 100%.
Of something completely unrelated to the product that is xD
Chambers had it wrong. "The King in Yellow" wasn't a play that sent you mad if you tried to read it.
It was a chemistry paper.
13%
98% yield...
For the tar
And 1,5% yield for the actual targeted product and 0,5% yellow colorants for good measure XD
Dudes face went from "average university student" to "burgeoning Viking" a suprise to be sure, but a welcome one.
Mate, that's just the done thing these days...
He's pretty!
I love when he just yolo’s and tries to do multiple steps at once.
When will I learn....
🎵We're refluxing some yellow toluene, some yellow toluene, now some black toluene 🎶
(To the tune of "yellow submarine")
in the toooown
north of melbourne
lives a maaan
of chemistryyy
and he lives
always so keen
to do a reflux
with toluene!
hey!
We're refluxing some yellow toluene
some yellow toluene
now some black toluene!
So we sailed beneath the sea
Thinking about the sixties
Hoping no yellow will be seen
Or we'll have to go back to Bunnings to get more toluene!
My experience with this reaction is that it has never worked with just sulphuric acid. And do believe me I have tried.
Best would be p-TSA with cyclohexane, Toluene works fine too. H2SO4 is usually detrimental to the yield..
Sorry Mate
Push this comment up.
So pre-made p-TSA it is. Tom, you should know that these "one pot shots" never work out well. Speaking from experience here.
Danielle Spargo "felt like taking a short cut" seems a bit harsh for a young PhD student with a cute and smart girlfriend. "Had better things to do" would be my description! Besides, how interesting would the lab be with textbook reagents? I'll answer my own question - "textbook interesting!"
Kevin Bauer
i didn't necessarily mean "shot cut" in a bad way. sometimes you take a shortcut home from work and get there sooner, but sometimes too many other people had the same idea and it ends up taking you longer to get home than it otherwise would have. if shortcuts work, obviously one should take them. and other times it's a gamble, it could take you less time, or it could take you more time, but you roll the dice. i definitely wasn't trying to imply laziness or anything like that
@Kevin Bauer that's what it is though, taking a short cut. Stop getting so triggered by that.
14% - if I win just buy yourself a lemon with the money, the best and most yellow of citrus.
@Extractions&Ire eat the entire lemon
Screw that. Eat an onion
@Joel Newstead a yellow one
@Extractions&Ire Are you the man who's gonna burn his house down? With the lemon?
I guess 14.1%, and if I wasn't lazy I'd log in on my other account and guess 13.9%, just to minimize the probability of moofy winning. If either of my accounts win, put it toward 20 liters of toluene.
One thought would be to prefill the Dean with toluene to keep the reaction conditions constant while reflux otherwise 30 mL of solvent is removed and doesn’t return. Ninja turtles rule!
Taking a shot with 19% yield, just to undercut the 20% guesses.
I think you need more time for the reaction plus removing solvent is important
I'm worried you're gonna hurt your neck filming intros like that all the time
Any% Yellow Speedrun cracked me up. Thanks Tom. Thom.
I'll say 8% yield so I can be pleasantly surprised when it's much more
i've been really depressed and i've lost interest in all the things i used to love but your videos make me remember why i was so passionate about chemistry and physics. thanks, brother.
"we're just going to do it all in the one bloody pot and hope the sulfuric acid doesn't murder our reagents" is one of the best lines I think I've ever heard spoken
Tom, you're a great guy who really knows what he is doing. You try to act dumb but we all know better. You have the seeds of greatness in you.
My organic chemistry professor is absolutely obsessed with this type of reaction, 5%
"I don't wanna get murdered by the sulfuric acid, but we'll have to see."
SULPHURIC ACID MURDERED ME AND MY WHOLE FAMILY
Really happy with some of the camera work in this video, Tom! Nice work!
Thanks! With 8 hours of reflux, to does give me time to set up some shots haha
So I have done one or two vacuum distillations, the biggest thing to watch out for that I’ve seen so far is you need to bleed in the vacuum slowly initially. This is in case some low boiling thing or dissolved gas exists that wants to come off around room temperature at that pressure. It could start violently boiling and fly over the still head and get in the condenser/receiver.
That and violent bumping. Use good boiling stones, chips of coffee mug work well. And grease every joint well and look for them to go transparent to get a good seal. Leaks in the system are hard to find and a major source of headaches.
Also be careful disassembling the glass later. It’s being drawn together tightly and likes to get stuck, especially because during heating the glass expands and you have to let it cool to take it apart, in the meantime it’s shrinking and contracting. Anyway good luck I hope this helps. Great video as always!
Leaks are easy to find, just squirt a little DCM over the greased joints one at a time - if there's a leak you'll have a huge drop in vacuum as the DCM vaporises and fills the system. It also has the added benefit of pulling the vacuum grease into the leaking joint and in most cases will seal the joint!
Also it sounds like you would benefit from using a splash head.
>chips of coffee mug
Are your dishes ok mate
Crude wet yield: 26%
Bone dry triple recrystallized yield: 8%
loving the new montage style of distillation, its like from an animals movie or sth
Thank you for stopping with that "di-ether" stuff... my orgo prof would go furious every time someone called an acetal a di-ether ...
Me, a computer science bachelor: Haha funny nice Australian Boi talk magic science words
@Evi1M4chine ok buddy
I was absolutely not interested in high-school chemistry but videos like this made me a chemistry buff and now I basically have a career doing chemistry
Meth with lead? Nice.
Also, Cubane? Cubane of my existence.
@Scrotie Mcboogerballs note: if you buy toluene and sulphuric acid as used in this video... Watch how quickly your house gets raided 😂
@Jayden Harrod 🤣🤣🤣💯💯
@Jayden Harrod you can get both in impure forms from the hardware store in most countries
@AgrippaCS not Australia.
The way you explain this stuff is so much less obtuse than any other channel, any other textbook, or any other professor I've encountered. Thank you.
Taking into account that he let the cyclopentanone reflux under aldol condensation conditions, without adding the ethyleneglycol and the color of the reactionflask; I'd guess around 12%.
Yeah he definitely polymerized his starting material. You hate to see it.
I was thinking this felt weirdly similar to my lab where we made aldol condensation products
I like your funny words, magic man.
One advice about usage of Dean-Stark: fill the collecting tube with toluene as well. The water molecule would drop down to the tube, and the drop of toluene would be pushed back to the reaction. It makes following the reaction much easier! The yield would be 33%
This is the first i hear of protective reactions
Look at me learning stuff
Guy That I've heard the phrase, but never seen it clearly explained.
@Kevin Bauer ikr, it's not even a complicated concept, it just needs someone to drop all the big wig terms and explain it in a layman's attitude
will you also make some cubane cigars?
ok fine I'll leave
Sigh
He would look very urbane smoking those Cubanes!
gotta vape them cubes
fidel castro is already dead, so you won't get funding from the CIA anymore
E&I: TOL-LA-WEEN
Hermione: Stop! Stop! Stop! You're going to take someone's eye out! Besides, you're saying it wrong. It's TO-LYOO-EEN, not TOL-LA-WEEN
Daniel Willems wtf why is every chem nerd up at 1 eastern
@StableEntropy Well I am from east coast Aus though, you referring east coast USA? Was around 4pm (AEST) my last comments. I think I&E has a reasonable following from Aus given he is a fellow Aussie.
Daniel Willems you are correct. Yes I was referring to the U.S. I would like to come to Australia if anyone wants to vouch for me lol.
Toll-you-eeen
TaLl-YoU-LeAn
Have you considered investing in a separation column? In spite of the time (and solvent) consuming nature of doing a silica column, I find no better way to purify organic reaction mixtures.
I love your videos. I did a lot of total synthetic chem in grad school, and never imagined someone could make it so entertaining. Great work, as always!
just from seeing the reaction i would have assumed you need a massive excess of glycol to avoid having your ketone react with itself in its enol form
Just found your channel, you are hilarious! Love the content
The speed run to any % yellow was hilarious
16% yield is my guess. We gotta get another yellow any% speedrun going soon, gotta protect your WR
I'm so excited to see the final product. I'd been wanting u to synthesize cubane for a while
Learned about Deen-stark nonsense from a Nurdrage video a bit ago and I'm now seeing it everywhere. It's a neat, clever bit of glass
Dean-stark haha!
This video is absolutely hilarious, I fucking love your channel!
Very cool to see others struggling with this reaction. We did the exact same thing in the organics lab in university, except with Benzaldehyde instead of Cyclopentanone (and we obviously didn't aim for some cubane). I remember that it took ages and we basically only had solvent left in the end. My guess for your yield is optimistic though: 30%
An incredibly optimistic 40% from me.
Sometimes you just need affirmation that something isn't a complete waste of time.
Loving the videos! Keep up the great work!
You could use a pressure equalized addition funnel with a condenser instead of a dean-stark trap. Fill up the addition funnel with some solvent if you're worried about the reaction flask going dry.
2 AM Productions - 2020-08-09
Actual yield: 8%
Tom's "eh that's dry enough" yield: 18%
Extractions&Ire - 2020-08-10
i feel seen
2 AM Productions - 2020-08-10
@Extractions&Ire Wet >>>>>>>> yellow any day though
nibblrrr - 2021-05-19
@2 AM Productions that's what he said ( ͡° ͜ʖ ͡°)