Extractions&Ire - 2020-08-24
Following on from the Dean stark nonsense last video, we clean up our product and attempt to work out how to do a vacuum distillation. What could possibly go wrong?? 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 is Polygon Window - clissold 101[dat28 otari] 48k
The vacuum distillation using a complete glassware setup but a vacuum cleaner might be the most hobo looking chemistry I've seen on youtube and I love you for that.
Bro you should see the stirrer I made out of a single 2x4, nine wood screws, and a stripped down drill press. Also, JBSC's nigreux funnel
@ezequiel cruz rosa Imagine the meme: Rice cookers are the "bad opinion" side of the meme, deep fryers are the "good opinion"
@ezequiel cruz rosa did you ever eat the rice from that cooker after that or nah
@word Before using it as a heat source, yes. but after that it was strickly for chem.
@word Thats like having a best friend turn GF and now you want to go back to being friends again after you seen how crazy she can fuck.
Once kitchen-wear becomes lab tools it stays lab tools. Like I didnt know you could do that rice cooker, thats really cool, youll stay here forever I dont even like rice anymore.
Ah, gotta love tar chemistry
Ah you are still alive !
I'm still waiting for some conc h2o2 projects
My first reaction for my phd was an imidazole (ylide) copper catalyst and it was brown goo.. thought I fucked up the reaction so I started over.. it turned out the the goo was my product. That was a fun couple of days trying to figure out how I fucked up.
No mate, ... "gotta RESPECT the chemistry" 🤣
Still better than yellow chemistry
I vote for mmHg to be replaced by “mercuries”
I hope these depecrated imperial units die out soon
Mercurydoos?
*mmmercuries
Tetrahedral GD thicccc mmmmmmercuries
@Justin Koenig mmHg is metric (though not SI). The US customary version is inHg, inches of mercury.
I'm gonna start using the phrase "mercuries" to reference mmHg when i start my pchem series next year. Dunno how often I'll see that measurement in biochem this year.
I already used your "yellow chemistry is shit " concepts in ochem. My professor now really likes your videos.
if you continue having issues with stir bars bumping around, i recommend cross-shaped ones. my school's lab uses them and they're really nice.
+
x
there are some things in life, like dating that girl you have a crush on, or getting high yields, that are just not meant to be
:(
This has been a good series. This is the best chemistry class I've ever taken (it's the only one since high school).
This is also the best chemistry class I've ever taken (it's the only one since my premature birth).
"PTSD hydrate"
Hahahaha
Sodium PTSD, tetrahydrate
PTSD-inium azide
this video is gonna give me PTSD hydrate I swear^^ but from pTsA to PTSD it'S nota far leap^^
First 3 mins of this video without sound looks like someone getting really, really into making quality coffee.
And the remaining 9 look like he “had a vision of the perfect cup” and took a dive off the deep end lol
“First, you need to wash your coffee...”
Funny fact i was studying the same reaction last semester and the entire class got the same thing and at the end we all had this caramel due to the teachers bad instructions so i really felt this one haha
Haha ok yeah you do feel better stuffing up when the whole class does it too
@Extractions&Ire for sure even more when its not our fault, our guidelines were wrong and they didnt predict that we would get more of one isomere than the other so when we tried the 2nd reaction we ended up with the same caramel that u have there .
Reactions like this one (specifically aldol condensations) giving this result are the reason I'm not an organic chemist. I was hoping you'd have better luck than I ever did!
Aldol condensation is a keyword here. Tom setup perfect aldol condensation conditions and beautiful conditions to turn the ethylene glycol into dioxane and by limiting the EG he all but guaranteed it would polymerize/dimerize
The reason you get such a bad emulsion is because of the ethylene glycol. It is very soluble in both water and toluene. It is literally used in formulations as an emulsifying agent. In order to break the emulsion you really need to dilute the ethylene glycol. You could try adding 5-10x the amount of water, or toluene, or both, and I think this would aid in your separation immensely. Also, if you don't do this, the ethylene glycol will help in dissolving your product into the water layer and your % yield will suffer!!
Only problem here is the ketalization reaction is reversible and produces water as a product, so excess water in the reaction vessel at any time will drive the reverse reaction by Lechatlier’s principle destroying the product molecule
@Nathan Friede Which is why he distilled it off in the first place
Resume: Separatory Funnel savant
:D
Try to use PTSA instead of sulfuric acid. I have done those reactions quite often and observed that sulfuric acid tends to form tar, especially when it was heated for too long. Don't reflux for 30h that's way too much. About 2-3h will do the trick.
Some ketal formings even needed temperatures below 0°C, because the formed ketal in the reaction mixture decomposed quite rapidly at RT.
If it's possible, try to check your reaction progress with TLC. I recommend using an vanillin/sulfuric acid mixture in isopropanol to make the spots visible.
Anyway, keep up the great work! Greetings from Germany :)
1:15 "wow i really need to learn some chemistry"
me: haha chemicals go boom
also chuck a flyback diode on the motor so you dont fuck up your PS.
"which can't tell is laziness.. or efficiency" good line
Not gonna lie i was expecting it to all go this way, but i'm happy you're not discorauged and gonna try again.
Can't wait for more EXPLOSION
This series is like a crowd-sourced synthesis paper. Gives some credence to the 'Wisdom of the Crowd' after all
Yeah, I think you should make and isolate tosylic acid first and then use that.
After watching these videos I now bring up Cubane in regular conversation and send my friends a picture of it’s structural formula, I actually think it’s funny. Thanks for breaking me even more
I don’t know a thing about chemistry but I get excited for your videos 👌🏻
same
Love this channel. Showing mistakes, admitting defeat and stating over. Inspiring!
Really looking forward to following this project (hopefully) to completion! Love these videos (even though a good amount of it goes over my head, I only started organic chemistry this semester =/)
Connections break, random stuff suddenly appears to fail for reasons unknown, some input materials a complete unknown. Yup, typical day in the home lab.
Good luck, hope it goes well the next time. And for me red is just concentrated yellow
Dang I think my bet was around 12%. I had faith! Oh well, time to clean up and reset, been there many a times.
I'm late to this video, but I've learned from heated magnetic beds on 3D printers that temperatures above 80C has the potential demagnetize non-neodymium magnets. This could explain the sudden lack of function for your stir bars.
As a physical chemist, every time you post a video, I am so I happy I do synthesis like 5 times a year.
2017 E&I really went literal with the “vacuum distillation”
If you want a perfect power supply for most purposes, get a junk bin ATX supply and short the appropriate pin for 12V at like 15A minimum capability. It will also likely have 5v and 3.3v as well.
Outdoors Tom: "Thanks, Editing Tom."
Light Mode Tom: "you're welcome :)"
You likely held the stir bars above their Curie point in what amounts to an alternating field so when they cooled down they were demagnetized.
The old vacuum gauges in 80's gasoline cars, econometers, is a pretty cheap version but works quite well for these sorts of vacuum levels.
Ex&F: uses obscure AFX tunes instead of stock music
me: :) good
(if any other youtubers are reading this, you also get bonus algorithm points if you use pre-1996 Boards of Canada in your vid. fun fact)
It works because they're from the soundcloud dump, so aren't released by a label (or even officially by Aphex Twin) so there's no copyright claims. If you use a track of Aphex Twin off of say, Syro, the video gets taken down within hours
Hello fellow trans person :)
Also yes the music is a chill bop lol
You can make a DIY stirbar puller from PTFE tube, PTFE rod and a neodymium magnet (cylinder/rod shape). These come in all sizes and diameters, so you can fit the piece of PTFE rod in the tube, as well as the magnet, making a chemically resistant puller. I use one made like that.
Similarly, you can even make PTFE stirrer from the magnet sealed with PTFE rod pieces and a tube.
Aldol reaction is how I used to purify ethanol from a commercial "bio ethanol fuel" mixture, which is ethanol denatured with dye, bitrex and 2% 2-butanone. Add a few spoonfuls of NaOH and an excess of CaO (to bind any water present), and you push the self-aldol of 2-butanone to completion. Pure ethanol is distilled from this mixture (2-butanone has the same bp as EtOH so after complete aldol self-condensation into high boiling crap, the CaO absorbing water and pushing it to completion).
Ah, separating pitch black/brown emulsions. NOW THAT brings me back to the lab.
Bummer about the tar, but I do enjoy watching you struggle through it! After all, when trying something new things rarely go right the first time around- that would be boring!
Best way to learn is from mistakes, preferably other’s, but nothing wrong with them being your own
It rembers me my first synthesis, a knoevenagel condensation. After the washings it looked like beetroot juice.
Holy... Filling that Seperatory Funnel that much made me feel uncomfortable, but I guess I never use it just to phase seperate, I always extract or neutralize or something like that
Gotta love the Dick Smith soldering station. Sold those for years at Dickys, got one for myself when they were getting sold (when woolies sold them). Best soldering station I've had for $50 (though rrp was $120)
Yeah it still works great, even though it's seen some shit over the years for sure!
You managed to beat every single prediction. I'm in awe
LoFi Australian chemistry to study/chill to. Thanks again Tom!
You will definitely pull this one off in the future. The biggest No-No for ketals/acetals is you can be acidic or have water present but NEVER both at the same time. This goes especially for the workup, acid needs to be quenched as anhydrous as possible if you want to extract, which is why using only 0.05 eq. of pTSA is so convenient: you add NaHCO3 at the end and are golden.
Beauty ! That's great looking Tar.
Moves nice and slow, lovely rich colour - looks like the Good stuff.
Not stuck solid to the glass either, which is deffo a bonus !
I love funny poorly executed science man videos, like the others this does not disappoint, even though it lacks yellow.
Nice job on the polygon window!
The stir bar got too hot / demagnetized you can use a screwdriver magnetizer to fix that.
This is straight up the sketchiest chemistry setup I have seen. But who am I to say, I still get tar and I've used professional lab setups.
Extractions&Ire - 2020-08-25
Should I get a different pump for the vacuum distillation? Or just manage with the one I use here hmm
arthur feliciano - 2020-09-07
put the pumps on series
GRBTutorials - 2020-09-12
Maybe you could a water pump and a Venturi adapter? Water pumps are cheaper than vacuum pumps and not as sensitive.
Helge Berneaud - 2020-09-12
how about re-doing the synthesis with pTSA? in my experience, reactions with H2SO4 always go black, I feel like pTSA might give you a cleaner product after all :D also, generally I would add all the reagents and then the catalyst last
chris murphy - 2020-09-15
@Daniel Coleman wish I could give this comment two thumbs up...
bromiso valum - 2021-07-09
@Extractions&Ire Instead of an aspirator you could also use a fridge compressor. Pulls about the same vacuum although the flow rate is low, so it takes a little longer to achieve the max vacuum. In my experience you can use them for 12+ hour vacuum distillations, just put a fan on it so it gets cooled that way. The advantage over an expensive real vacuum pump is that they can be got from dumpster diving, and you can put corrosive fumes through it without worrying too much since they are cheap.