Cubane Ep 5 - Dioxane and Bromine
Vložit
- čas přidán 22. 11. 2020
- In preparation of the bromination step, we make some more bromine and 1,4-dioxane, and achieve yields so high that might actually be negative numbers. Subreddit: / explosionsandfire
Join the Discord!! / discord
Twitter: / explosions_fire
Patreon: / explosionsandfire
Music is as usual from the Aphex Twin soundcloud dump, track names are:
- 13HighHatsTuneTamclapOrig
- Sams Car
References: 1997 Lab scale paper: www.researchgate.net/publicat...
2013 Pilot Scale: pubs.acs.org/doi/abs/10.1021/... - Věda a technologie
*slaps blackboard* This bad boy can fit so many reactions on it.
so many terrible drawings
*slaps beaker* ......fuck
So many shitty hexagons…..
@@spiderdude2099 *pentagons drawn believing they were hexagons and hexagons drawn believing they were pentagons
"And over here we have some concentrated sulfuric acid"
*pans to half broken cylinder*
Glad I'm not the only one that noticed
I genuinely do not know how you've done it but you've been pumping up the content quality while simultaneously upping your shitpost game, highly impressive.
Neglecting my day job
@@ExtractionsAndIre mood
@@ExtractionsAndIre That's the fucking spirit.
@@vaderdudenator1 @Extractions&Ire mood
Tom: does chemistry.
Chemistry:"And I took that personally"
:D
The only chemistry channel on youtube where we take a tangent to focus on latex and sweaty men
Nile red never even breaks a sweat, he's too cool and collected. I own the market share for sweaty chemists
@@ExtractionsAndIre Con theo: Nile red is not real. Have you ever seen him show human traits?
@@whatevernamegoeshere3644 are you sure that E&F isnt NileRed? have you ever seen them together in the same room?
@@whatevernamegoeshere3644 the mark zucc of chem
@@ExtractionsAndIre he’s also Canadian
I love how efficient your home lab is! You have so many unique multi purpose tools, like a graduated cylinder that doubles as a murder weapon from Clue.
“Let’s dry this dioxane by adding a huge amount of water” XD
It's actually works like that if you adding not just water but saturated solution of salt so it can pull water trying kinda to dilute itself
@@nik.akhmetov it only works if the thing you’re trying to dry isn’t massively soluble in water...
@@nik.akhmetov I’m also not just taking the piss- the only way you avoid this kind of head-slapper is the remembered mortification of having done it yourself.
@@Grak70 yeah ofc
The good ole chemistry chuckle
imagine having him as ya science teacher , would be sick mate
ya everyone would fail but it would be rad
W S he would have the kids make something that goes yellow if you did it wrong and start bitching about how yellow is evil
Would it though?
Actually my Math teacher looks like him
There would be no survivors...
Filter paper struggle and the glove sweats. This is my kinda content
You waving to camera in the reflection was 200% "Dad filming home movies"
hell yeah, that's the sort of vibe I want
That intro is just... *chef's kiss*
my name chef
I was really hoping for some chocolate ice cream chemistry, but then he said its just KOH 😢
significantly less delicious
I donno.. It has an E number.. (E525) so it /could/ be delicious...
@@ElectraFlarefire nah potassium tastes like ass
@@spookywizard4980 yup thats why only health food nazis buy it, along with the unfortunate suffers of heart disease
@@alockworkorange7296 while I'm apprehensive about supporting their cause, I am grateful for health nuts. Because of them I can get concentrated peroxide 😂
The GameCubane was my favorite console.
Same lol
I love the octanitro-GameCubane - but it will explode here and there.
"That I acquired somewhere," was the shadiest thing he could have said.
Then he followed with "I don't really remember,"
Greetings from the Isle of Man. I haven't been involved with chemistry since high school 35 years ago. Been watching your very entertaining content for years now though and find it fascinating. Keep up the good work.
Thanks mate!! Appreciate it
Is it me or has Tom been replaced by a better more successful, talented and smarter alien ?
bro I got negative yields here
@@ExtractionsAndIre Aah it's good to know nothing has changed over the years !😆😆😆
@@ExtractionsAndIre Just take the compliment.
@@ExtractionsAndIre it’s dry though!
That game cube intro got me, I was like wtf did I click on the wrong video. 😂
If you want to make absolutely sure you remove all traces of acids from your bromine, even HBr, you can add a small amount of anhydrous disodium sulfate or trisodium phosphate to it, before the distillation. That way, you'll make sodium bisulfate and/or disodium phosphate, which are entirely non-volatile, and absolutely cannot be carried over in your distillation.
It's a little trick I used when I had to remove HCl from TiCl4 and VOCl3. ^^
5:34 "Wouldn't be an Extractions & Ire video unless we committed at least 3 atrocities..."
*Goes to get the white phosphorus and cyanide*
Also 10/10 opening
Last time I was this early the pentane hadn't even pissed off from your stale petrol yet!
Imagine old Bill shows up and you have to explain "No officer. It's not a meth lab. I'm making explosives".
I have no idea why I feel this in my bones but your last distillation is wrong, I feel it is against nature to distill from right to left.
The original simmetry breaking? 😅
the measuring cylinder with the H2SO4 🤪 ...
This is advanced backyard chemistry.
They look like that so often, that I beginning to suspect someone sell them like that.
It's a rare wapon with extra acid burn demage $^》
Me and my roommate's cat watched this video with equal interest.
Either you were very not interrested or you better start becoming your roommates cats favorite human
@@Blutwind I have already succeeded at this don't worry. I am the only human he allows to lift him.
Cody Carpenter awwwwwwwe
@@bhutwheyttherismor86 I know I'm a little late to the party. But was your roommates cat allow your roommate to pick them up, or just you? Because if the cat was only okay with you holding them, then I wouldn't necessarily call it your roommate's cat anymore.
What's up? The quality of this video is higher than any previous video.
Went into quarantine for 3 days lol
@@ExtractionsAndIre rip sa, ur mates in wa are thinking of ya
Best thumbnail i've ever seen in my lifetime, I think i probably reached the peak of my lifetime where I see the perfect and unbeatable thumbnail, really, thanks Tom
The thumbnail quality is through the roof.
Dude I'm not a chemist, I have a small amount of knowledge and a fair amount of your stuff does kinda go over my head lol. however I love your videos my guy I cant get enough
You’ll be a chemist just keep watching :)
You're not alone, mate
Haha I do the exact same thing. I don't know what's going on but I like the way he does it
That into made me laugh way more than it should have
Love your glassware. If it ain't broke... Er, well...
it only broke when it becomes unusable.... right?
Checking in from the west coast of Canada.
I did high school chemistry in the 70's (no, not that kind, well maybe a bit)
I really liked it but I chose a different path to follow with my career.
Now 45 years later, here I am watching some guy on CZcams.
I honestly have no idea what you are talking about most of the time, well more like all of the time, but I still enjoy it.
Hehe, intro's Great!
10:10The way you picked up the plastic cup after you poured the Sulphuric Acid made it seem like you were about to drink it.
Mmmmmm, bone hurting juice.
The real bone hurty juice would be Hydrofluoric acid.
@@jaxblonk5127 isn't that more spontaneous self combustion hurty fluid?
@@samn6498 I mean, it's a damn angry juice all around- if you get that shit dripped on you then it will leach the calcium from your blood and your bones and make your heart stop as a result.
sam neale HF doesn’t combust
Fav person uploads : day improves
starting my road to a PhD after graduation next semester and I've just found your channel and I absolutely love the specific form of chemistry humor that plagues my internal monologue while trying to fumble my way through papers and synthetic schemes. Please keep the content coming and wishing you the best of luck on your thesis/dissertation if you haven't started on it yet.
This guy feels like the MaxMoeFoe of chemistry
I've listened to too much Aphex my dude, every time a song comes on, I forget that you use his music and I'm like: "I swear I've heard this before...."
yeah i kept thinking the music was someone who was trying to recreate aphex style techno but no it is literally just him
Thanks for yet another amazing video! Your struggles make these videos so much more human, and I absolutely love it. Keep making great content :)
I truly love the humor in these sick videos man, really brightens my day.
Tom : bloody vapors everywhere
His subtitles : buddy vapors everywhere
👨💻👍
Yay, another video of my favorite channel : Distillations & water
Youre the best man! Bought a few of your shirts, and you inspire me! I’m a process safety engineer and you encourage me to learn the chemistry of what I work with :)
2:11 distill it anyway might get some free E&F content out of it.
That's the worst kind of E&F content, the ones I don't plan for
At least you're starting when the sun is still up. Round here it's like, "Hey, it's 8:30 pm, what little thing can I pull off in the next hour?" (No, not like that you dirty buggers!)
Next thing you know it's 11 and we're just getting underway...
Christ up where I’m at it’s like “8:30 PM? The suns been down for 4 hours!”
Love watching your videos! Can't wait to see more!
That GameCube intro brings back Ty the Tasmanian Tiger memories.
Yo that game series fucking _slapped_
Also, it's available on Steam now
This man really out here showing us step by step how to detonate our garden sheds.
Bulla is the word for Bun in the swedishdialect I speak. No worries, your welcome!
I am loving this series man.
Glad to hear it! I'm enjoying it too!
HOYDATOIN MATE!
So excited for this project! Even if we never get to see any cubane at the end, the reactions are really ineresting!
the intro is top tier, good job!
Love your videos, keep up the great content!
Thank you tom, very cool!
I love your videos man, they're the perfect blend of funny & interesting. You should do plant extractions, maybe with an ultrasound cleaner?
Love the intro xD
great job mate
That intro tho... what a throwback and a good laugh as well
I bet it turns yellow.
Odds are about $1.01 with that bet these days
@@ExtractionsAndIre decimal odds? Disgusting.
I know next to nothing about chemistry but your videos have got me interested
Haven't started vid already laughing at the intro, god this is great
Nice thumbnail and great intro Mate !
I don't know who added subtitles but thank you from the bottom of my heart
I love you and this show you're like the science teacher I never had. No bromo 😂😂
Another wonderful video thank you sir!
thank you!!
You off the wall crazy ass. Keep up the good work.
10/10 opening in this video
The "we fucked it" had my drunk self cry laughing
You may need to add an atrocity counter 😂 great work though as usual mate!
Watching that bromine neutralization was so fucking satisfying!
about half the reason i watch this channel is so i can expect afx music while watching sped up chemistry
I fucking knew it was Aphex Twin!! was listening and listening and decided damn and checked the description.
i love these EXTRACTIONS&IRE
I love watching your vids
Hearings Tom say “Oz” gave me flashbacks for Borderlands the pre-sequel and their fucking Oz Kits
Got an ad before this that showed a christmas ornament that looked exactly like the flask on the thumbnail. *confused*
11/10 thumbnail and intro
Just stumbled across an australian product called the penguin dry ice maker. It is basically a bag you hook up to a Co2 cylinder to make dry ice on demand. Depending on the closest place to you where you can refill co2 cylinders (usually a drinks supplier will fill them up for beer carbonation etc. around here it is about 20$ per 10kg of co2) this might be a way for you to get easier acess to efficient low-temperature cooling in the future. If you do get a co2-tank, get yourself one with a dip-tube and save yourself a lot of trouble. If you ever need gas phase co2 you can simply refill a sodastream cartridge (can be had for very cheap) and hook up a pressure reducer to that. The necessary equipment for that can be had at kegland in Australia
I am way out of my depth and have no idea what is going on, but I am still entertained!
The amount of jank and nervous laughter in these videos is wonderful, hah
This gives me, a final year chem undergrad, hope that I too can successfully combine my passions for chemistry, tangents, being clumsy and memes.
When the stem was tilted and the camera was looking down into all I could think was "egg cam"
Love your channel and can't wait to see nice fat cubane structure being made! Sorry to hear about your azeotrope blunder. I made dry dioxane several years ago learned about its miscibility with water hard way. Potassium hydroxide works really well. After multiple treatments with solid KOH it is already reasonably dry and peroxide free. You can go for Na when it stops forming dirty alkaline aqueous layer at the bottom. It takes around 24 h of reflux over sodium to remove the last traces of water. Hope it helps and you will be able to recover all the solvent in this jar.
I like this intro, I watched it like 4 or 5 times
Dude i dismissed chemistry in school after 10th grade and have no fucking idea what you do. Still i watch almost every video of you, just because I love the level of passion and this lazy genius attitude you bring in.
Your skill of beeing entertaining is far from turning people in a yellow state.
So yeah, thanks for entertaining me, spending my time with stuff I dont understand. Geat work.
Quick tip about putting label tape on containers: If you fold over a small piece of the tape to form a little tab, removing the tape becomes a much easier process later.
Love your videos 👍
Nice job on the music and audio levels
Is it good?
I think so, I started watching it but then I got distracted like I do and remembered I had to do laundry so I went to eat my cold dinner but as I walked away I thought the video switched to commercials,I liked the music so I went back to see.
However I noted it wasn't music from a commercial because I saw the shot of the flasks halfway with the music playing, sounded great and then it jumped back to you talking and I noted there was good clarity and roughly a similar level, or at least one with a proper scaling towards the previous audio clip, and also the levels were decent in comparison to the previous and following video.
Haven't seen the last part because I remembered the laundry again so I cleared the floor to vacuum. I will watch it later though since I'm following this better than my activities but the part I did hear had a nice tune I hadn't heard before and nice audio scaling as well.
Also like your video's, not much of a commenter but I've seen a lot of them.
You and nilered are actually the way I study chemistry during breakfast
I live for the shots of Tom waving to himself in the reflection of his glassware.
I LOVE the intro!
I know nothing to do with chemistry, but these videos are still very interesting and entertaining.
I've been following every video, but also, what were we doing again?
I know there was a reasonable amount of shitposts in this, but the number of catastrophes is surprisingly small, excellent work bad science man!
amazing intro 10/10 good it wasnt yellow
It was nice to see another colour than just yellow or black this time around :)
"I bought some TLC plates so I can monitor the reaction progress"
Please tell me you have staining solution and not just thought of using a UV lamp
Also, the ice cream might be dairy, but with that labeling, there's no way it's cow milk. "I swear it's dairy man, like for real" lmao
Yeah when they write dairy so many times on the box you get suspicious for sure haha
But yes, staining of TLC plates, will have to have some serious undergrad flashbacks to make sure I can do it okay. Thinking permanagate will work alright?? Or do I need like an easily oxidisable group in the substrate to make it work, and what are other alternatives?
@@ExtractionsAndIre what kind of TLC plates, in the first place? We most commonly used SiO2/Al2O3 (with fluorescein each) and sometimes cellulose; I remember iodine staining and other more specific solutions
@@ExtractionsAndIre KMnO4 should do the trick, solid I2 as well. The other stain I could think of is 2,4-DNP which is particularly good for ketones and aldehydes, but I'm not sure it would be available to the home chemist.
@@ExtractionsAndIre www.epfl.ch/labs/lcso/wp-content/uploads/2018/06/TLC_Stains.pdf
I love the intro. I love it so fucking much.
Broken graduated cylinder is my favorite side-character.
honestly! people keep asking me to get rid of it, but I think it's a staple of this channel now
@@ExtractionsAndIre it's a great Easter egg and if anyone gets out of line, it'll cut a bitch.
If you ever find yourself making dioxane in the future, follow the NurdRage procedure except use a Vigreux column before the condenser; don't fill your reaction flask more than 1/3 full; and use a lab jack to hold your mantle. The Vigreux and 1/3 full rule gives you more headspace to catch tar foaming over, which you can cut off by dropping the mantle with the lab jack. Play with the stirring, too slow or too fast and the tar foams up like crazy but there's a nice sweet spot where you can push the reaction pretty far before tar foaming becomes uncontrollable. Using a 1000 ml flask I can make 135 ml of dry dioxane per run which isn't too bad.
with the reaction, how do you control where the bromine attaches onto the molecule? and dose it matter?
I'm assuming the reaction proceeds through a radical mechanism (unless the dioxane does anything fucky with it - a quick google search hasn't told me much about the reactivity of the dioxane-bromine complex, so there's probably no major change to the mechanism). This sort of radical substitution will tend to primarily proceed through whichever intermediate is the most stable. Generally, radicals are more stable in highly substituted positions due to an overlap of the radical electron orbital with neighboring σ* antibonding Orbitals (this is formally called hyperconjugation). Therefore, a radical will be more stable when it's right next to the fully substituted carbon rather than on the opposite side of the ring, hence radical bromination will prefer substituting this position.
Depending on how high the energy difference between the two transition states is, the reaction is either going to proceed cleanly (if there's a high transition state energy difference) or it's going to be a mess and require really tight temperature control / a selective catalyst (maybe dioxane does that, idk). I'd be more worried about not being able to selectively get 3 bromines on, because if the product is contaminated with significant amounts of mono-, di- or tetrasubstituted bromoacetal it's going to be a nightmare to isolate the product from that mixture (if not impossible without good chromatographic methods). Just using the impure stuff would fuck with subsequent reactions, as the following Diels-Alder step and the final closing reaction need bromine in the right position.
TWO products from etylene glycol acid reaction: dioxane and acetaldehyde which polymerizes on acid contact ergo your TAR. The acetaldehyde also forms an acetal with glycol which is isomeric with dioxane (same boiling point?). Acetaldehyde boils ~20C.
The game cube intro startled me