Chemiolis - 2023-03-01
This one is for all the homechemists out there, finally something u can replicate ;) Support my channel with patreon: https://www.patreon.com/chemiolis Support my channel by becoming a member https://www.youtube.com/channel/UCoDmZirW1o9XSKSRM6YJ1rQ/join
Wow that 100% yield on the last reaction was some next level chemistry
Look more closely, he massively exaggerated the yield. It was 50% at maximum.
@@realedna that's what I was going to say. It was two socks but only one got dyed, so wouldn't that only be a 50% yield?
@@keithyinger3326The azo dye is clearly the limiting reactant in this case, so I think 100% is fair XD
@@realedna he used the holed sock %48.74 at max.
The separating of the red substance with the sand in tube was epic to see. I was mesmerised by it.
Column chromatography is very pretty if you have colored compounds
Only the thin (3mm) layer at the top was sand that is used to hold the column fill in place, if it was just sand it would just work as a filter. There are many different materials used for the column fill.
Chromatography is used to purify many specialist chemicals because there are sometimes totally unavoidable side products in synthesis.
Just a friendly advice... Add the stirbar to the flask before placing the flask on top of the magnetic stirrer. The heavier stirbars pose a significant risk of cracking the flask or beaker when being pulled by the sirrer magnet. And in accordance with Murphys law this will happen at step 35 of the 37 step synthesis you have invested your life savings into. Trust me, I speak from experience. 😒
This is exactly my thoughts when I see that stir bar is dropped to the flask. I understand it looks nice on the video but can cause a disaster.
Yeah, it always hurts when people do that
The ending was epic. Some real chemistry YT content there. And this is how you do a 100% yield, folks, take notes.
Thank you once again for your entertaining content and hard work.
Whenever I have a bad day, I just watch the videos from this channel and drink a shot every time he says "short path vacuum distillation". It always works to lighten the mood
An alternative to the metal/acid reduction could be thiourea dioxide (TUDO). TUDO is available cheap from indigo dyer suppliers (it's now used instead of sodium dithionite, which cannot be shipped by air anymore) and it's a pretty potent reduction agent providing for a much cleaner reaction than dissolving metal. Procedure usually uses aqueous ethanol as solvent, nitro aromatic and NaOH are first dissolved, followed by TUDO and heating at 70°C for a few hours. The actual reducing agent is formamidinesulfonic acid, formed in situ from TUDO and NaOH.
18:26 "it become as white as my ass in winter"
dude this is definitely something to put on a shirt, let me buy it !! ahahah
"Creates enough heat to sustain nuclear fusion" 🤣
I am an azobenzene scientist, focusing in photoswitchability in condensed state. We think that tight packing due to pi-pi stacking usually inhibits photoswitching. That's why my research is focusing in how to allow this photoswitch in condensed state. Judging from your azo, it seems to be tightly packed. To confirm photoswitching I usually make solution, irradiate, and (1) do TLC (for quick confirmation) or (2) take UV-Vis spectrum (for formal photochromism report)
That was a 50% yield. The second mole of sock was not reacted.
You're like "see it isn't crazy", well, that doesn't matter because it's damned genius, how you continue to come up with stuff that's original, I've never seen in school and could be done at home is absolutely amazing!
P.S. and another comedian with carcinogenic socks
A nice fast trick to crash out amines as an HCl salt: Dissolve the crude mixture in ether. Take a test tube on the side and fill it half and half with concentrated HCl and ether. Then spray the top ether layer through the bottom HCl with a syringe and let it separate. The ether will take up some of the HCl. Then add the top HCl-in-ether layer to the flask with your crude mixture until the amine stops crashing out. Last step is filtration aaaand done! Keep up the awesome work man ! <3
Really enjoyed you having more fun with the commentary on this video - great work on refining the nitration step also!
The production value behind your videos keeps getting better every new projects you have worked on!
The dry pan delivery makes it even better.
Epic video, acetone dehydration is quite cool.
Easily your best video yet. Hope it does well so it encourages you to make more long-form content! :)
Omg, I admire your patience with this reaction! Awesome!
Yes I think this is a good one to start on! Garden hose pots and pans. Battery acid. Acetone nail polish. Etc
3:30 Tar reaction mixture, yellow distillate. Perfect for Tom from Ex&F to see.
also, terrible yields, dodgy syntheses, and nitrations
I really like that you posted the worse method as well as the working one... so I don't have to wander what would happen if I added H2So4 and HNO3 combined etc.
Great video! I have to agree with Thatchemist's advice to dye something after going to all that trouble synthesizing it..
It was a good contrast to see some "novice fabric dye experiment" shenanigans after all the legit informed chemistry :)
I say that with all due respect - how many tie-dying channels are going to synthesize their own dyes? :D
I like these videos! They remind me of old NileRed (not that there’s anything wrong with new NileRed, but it’s nice to see simpler reactions again). I live vicariously through these videos; I was gonna be a chemist, but I ended up going with a different major. I miss doing chemistry, but maybe some day I’ll come back to doing this!
Alistair Crabb ...Remember what Tom Cruse said ... "Someday is code for Never"... :)-
It mostly reminds me of old NileRed in the way that there is more than one video a year ;)
I've been making azo dyes in my research for my Master's degree for the last year, and I feel this video SO much. Weird tars, shitty yields... It is worth noting that we've found that the more heavily substituted the location for the azo coupling is, the harder it is to get any decent yield. 3% for a dye that has a 2,6- substitution around the aniline is pretty much par for the course. My PI actually joined me in the lab to help figure out an alternative... I'm not actually doing an oxidative coupling,, just traditional azo coupling, but I wouldn't be surprised if similar issues showed up even with the oxidative coupling. You still have to get the NH2s close enough to couple. Steric hindrance SUCKS and it seems like it shouldn't be that bad, but it IS.
when in doubt (metal) couple it out. some of those metal couplings stop at nothing. i'll always be shocked by the amount of bulk organometallic chemists manage to fit onto their tiny transition metal ions.
Whaaaaat. That's cool man. So commercial dye suppliers are only getting a couple percent yield in their processes? A few years ago a big supplier of chemical precursors in China had I guess an explosion or something in a warehouse, and for like two years there was this blue dye that was impossible to find because of it. Finally other people found different synthesisisis and we access again, but it being ridiculously low yield makes sense to me now as to why it took so long!
@@thatguy431 No, most of the commercial dyes aren't nearly this hindered. If you only have one methyl group next to the amine, yield goes up to 50-60% without too much trouble. Remove all substituents adjacent to the amine and yield is easily over 80%. The really hindered dyes aren't actually much use for commercial dyes, anyway, because they don't bind well to fabric.
@@christineg8151 Very nice how internet sometimes show some nice things. I work with azos for 6 years, and I really know the struggle with preparation of various derivatives. I am mainly focused on unsymmetrical diazenes, ones that cannot be made by azo coupling or Mills reaction :)
We do this by sequence of Buchwald-Hartwig coupling of Boc-hydrazines and arylbromides, which are then oxidized. Nicely modular :)
Make the diazonium tetrafluoroborate salt of one aryl component and react it with a lithiated second aryl component. Think that's from a Ben Feringa article iirc. Very nice for asymmetric azoarenes. Warning though, as diazonium tetrafluoroborates are potentially explosive compounds. They're a whole lot more stable than e.g. the chlorides, though, so can in most cases be isolated safely, but proper caution is warranted. Also you need directed metallation, or alternatively lithium-halogen exchange to make the lithiated half. Haven't tried the exact Feringa procedure, but planning to do it soon-ish. And luckily, in my case the diazonium tetrafluoroborate seems fairly stable. At least enough for me to have made and used it without blowing up, lol
Very nice synthesis! And pros for mentioning my beloved carbenes!
Most anilines can be steam distilled which is a great method for separating them from tar. As for their precipitation, most often Et₂O is used as a solvent, one because dry HCl is sold as an ethereal solution, two to lower salt solubility (i suspect some ethyl acetate hydrolysed, air moisture everywhere, and alcohols dissolve amine hydrochlorides very well). As for column, just plug on silica on fritted funnel would be more than enough XD
I agree with tin reduction, I never had luck with it and it is very messy, too much for my taste.
As for oxygen source, better than exhaust from the pump (if it was diaphragm one it is ok, oil ones are horrible for this), washing the bottle with solid NaOH/KOH would help a lot, additional drying as well as CO₂ capture.
What a masterpiece of a video! The jokes really made it too. Very thorough in all the trials and the procedure and improvements. Really good to see the whole process because it can be really disheartening when doing chemistry to see only success online and failure when you try it.
One way you could have improved was during the steam distillation(s) of mesitylene was you could have used a dean stark trap / Clevenger apparatus. Also pretty sure that caking the dye on the sock isn't necessarily the best way to dye, there's probably a way to chemically bond lolz
A good alternative proceedure to prepare dry HCl in-situ for this specific application may be generating it from Acetyl Chloride/MeOH. It forms Methyl Acetate and HCl which would solubilise the compound and then simple distillation would remove excess solvents affording the hydrochloride salt.
You have become my favourite YouTube chemist
Your yields are always great. Very satisfying unlike most other chemtubers 💀
First of all, very nice video and I appreciate the amount of work you put in this video and in the synthesis.
Your videos are very informative and in every video I learn something new.
How do you analyse your intermediates and your products?
The stir fish in the dish of socks though 😄
Now that is some ambitious chem. Props, that's impressive
Speaking of sulphur dioxide, me and a high-school classmate accidentally made some when we were dehydrating (is that the correct term here?) one of those salts that contain water in its solid form. It turned out the little ceramic vessel we put the salt in to heat it contained some sulphur impurities. That gas is not play with, real nasty stuff and it took until the day after before my throat felt ok again.
Also, as you can tell I'm not even close to a chemist, but I really enjoy your content! Feels like I learn something in every vid
really neat to see advanced stuff from simple chemicals.
This is a work of art
That was a lot of work, dude!
God your videos are great. And your dry humour gets me every time.
One of the best chemistry channels doing things that may be ridiculous but are scientific.
I love your videos and ideas. I'm a chemist like you, but maybe younger and without a lab :/ Regardless, these kinds of videos refresh my knowledge and perspective on chemistry.
Go ahead and share your knowledge with the world. I wish you all the best :)
Best nitration reactions that I’ve managed to do were with cold “over 100%” nitric acid.
Over 100% nitric is just nitric acid with extra dinitrogen pentoxide (nitric anhydride) dissolved in it.
I love the way you say Iron!!
I really enjoyed the part where you explain what you could do differently! It shows well the chemist's mindset at work
Looks super easy... I'd like to see Explotions&Fire try this. It's definitly going to be yellow and/or tar all the way :D
Hmm for nitration, we usually mix the nitric and sulfuric acid under cooling(SLOWLY!) before adding to our organic compound (also slowly holding the reaction under 25°C).
Keeping in mind not to let the acid mixture ro get to warm since you gonna experience the the formation of toxic brown nitrousoxide gas.
Exactly. The mixing already creates so much heat that if happening in the reaction flask, would create local hotspots that create heaps of side products. Which is seen in the video 🥹
I mixed the acids normally without cooling (also did this before a toluene nitration) and did not see any gas, but yes it might be good practice to just mix them gradually to avoid any potential issues.
A stable carbene? That's so interesting, you have to make that!
Next vid I will make and use one as a catalyst 😎
Your yields are always great. Very satisfying unlike most other chemtubers . Your yields are always great. Very satisfying unlike most other chemtubers .
Ok, so, these kinds of dyes are supposed to react with cellulose. So like cotton or natural fibers only. If used on polyester or something it will just wash out. Also, in order to ensure bonding happens, it needs to be in a basic environment, so us tie dyers will soak fabric in a soda ash solution before dyeing. It's cool stuff!
Very nice job, sincerely congratulations. I have some considerations to do. Mesitylene synthesis can be seen as the cyclodehydration of three molecule of acetone. Using conc. sulfuric acid as dehydrating agent gives many side reactions because the acid react also as acid in fact. You can try others.
The mess with nitration products can be easily solved with a good chromatography column and hexane, hexane : DCM as eluent. It is ever not so safe warm and distill nitrated compounds. Take care. As last that tar can be even more interesting than title compound.
The amine can be precipitated dissolving in DCM and dropping carefully conc. H2SO4 until no more solid forms. Filter, wash and crystallize.
There should be a direct reduction of nitroaromatic to corresponding diazo compound.
I would love a lab tour!
"It turns as white as my ass in winter". I was not expecting that. 🤣
The baguettes were a nice touch
@puo2123 - 2023-03-01
Really cool chemistry. Had multiple years of organic chemistry and never heard that you could get a C6 ring from decomposing Acetone
@That_Chemist - 2023-03-01
I know right!
@b3dubbs72 - 2023-03-02
Forbidden benzene
@Jokke197 - 2023-03-02
@@That_Chemist My words exactly, before I saw this comment. 😂
@beryllium1932 - 2023-03-02
Happened across it in the Merck Index a while back. Once you know it, you'll never forget it. Another zinger: you can make acetone from vinegar and lime (and hard work)
@ThorirLenvik - 2023-03-02
You haven't been reading old enough textbooks of basic organic chemistry, I guess! I started reading older textbooks (chemistry, biology and electronics etc) as soon as I figured out how to read (basic university curriculum was available in the common libraries in the middle 1970s), and making aromatic rings from aceton or acetylene was atleast described in books from before 1960 ..