I have been working on a bigger project these weeks that is very difficult to get right, I hope to still get to finish it in the way I want to, but it will probably take a while. At the same time I don't want to upload too little so I will take on some shorter and more established syntheses inbetween. For now, enjoy this potassium prison. Also, ideas are welcome 🙂
Salvarsane, the first antisyphilitic medication. I know you've already had experience with arsenic and it is not as horrible as it is expected to be, just as cyanide (don't eat=everything ok)
@@Tyresio12 crown ester 18-6 is way cheaper and is capable of dissolving KMn04 in non polar solvent, cryptand is more of a scientific curiousity subject (for making Na anions or other obscure stuff)
Bro, make a pure negative charged liquid by imprisonment of potassium
ปีที่แล้ว +108
A little trick that I like to use for hydrogenations like this is opening both valves, letting some hydrogen escape until you hear a change in pitch of the whistling. At that point you know its basically pure hydrogen coming through and all other gases have been purged.
I love the detailed mechanisms and diagrams (like the Pd/C one)! A lot of organic chemistry youtubers will show reaction schemes but not really show mechanisms. It really helps make your content more approachable to someone who isn't super well versed in organic synthesis.
Someone in my lab was using sodium azide for a synthesis, and the procedure he was following called for DCM as the solvent. He didn't tell me at the time and put the residual azide and DCM waste into a labelled P-listed waste container. A few months later, I find this container in the back of his hood... that was a fun call to EHS.
Waste disposal methods are always interesting to see. Especially when there are risks with storing it. As always, there is no one "right" way to deal with it and sometimes seeing something I might do is educational. Oh, and thanks for another interesting video!
I have been waiting for another of your videos for a long time it seems, thank you so much for making this one sir! I understand that things takes time and i am looking forward to your other projects no matter how they go really.
I worked in a research lab for 3-4 years designing and handling PEG ethers. I see those Tosyl and Trityl derivatives in my nightmares. We made some azide derivatives too but the carbon to nitrogen ratio was well over 3
this is so awesome, I'm a computational chemist/biologist working on chemosensors and their affinity to their ligands, and am literally working on publishing a paper over a type of Cryptand right now, so seeing this video come out from my favorite chemtuber is so cool.
@@monika.alt197Right? I think it’s pretty cool that the sulfonyl group of TsCl reacted with the alcohol of triethylene glycol in something akin to a nucleophilic acyl substitution reaction. I didn’t know you could do that with sulfonyl groups but it makes sense now.
Realistically, I think these are the best chemistry videos on TH-cam. You sure do like your chromatography columns though, even if this one wasn't used that way.
If you want a good eluent for the diazide product I used 80% Methanol in DCM, sometimes even 90% methanol in DCM. They REALLY don’t separate well, also I was working with hexaethylene diazide, so maybe it would be easier, or maybe harder, I’m not sure. But I agree, it is frustrating. We usually used excess sodium azide to avoid this.
Excellent video, I really liked the part where you showed the Pt as the catalyst. never seen that before. Insightful video. In lab the best yield I had ever gotten was 85%, had I gotten 80% would've make my professor be happy lol
I used to work for chemical company that produced crown ethers. I mostly made 18-crown-6, dibenzo 18-crown-6 and dicylohexano 18-crown-6, made by hydrogenating dibenzo 18-crown-6. I worked on a pilot plant scale most of the time.
An explosion at a kilo lab (a lab used for syntheses of chemicals in kilogram amounts for research) in 2008 was believed to be caused by diazidomethane accumulation in a rotavap.
I know near nothing about chemistry, but those big rings made me think of catenanes, and I always wondered what a catenane polymer would be like. Like a molecular chain.
Hey! Question, though: Did the volume in the balloon decrease after all? I ask, because in more typical hydrogenations it's also hard to track the progress because you can't really tell whether the H2 has been consumed by the reaction or just diffused away through the rubber. But then, if one really wants to be sure, one could just fill a second balloon with H2 and keep it at hand to compare afterwards.
Here is a better way: Starting from your starting reagent of triethylene glycol, do an Albright-Goldman oxidation to the dialdehyde using acetic anhydride and DMSO. Purify by distillation to remove the acetic acid byproduct. Do a reductive amination via a modified Leuckart reaction using ammonium formate and 2 extra equivalences of formic acid. Purify by recrystallization as you do. Only a two pot reaction pathway with very minimal byproducts that are super easy to remove, and most reagents should be inexpensive and readily accessible.
i read a while ago about people making thins on a molecular scale like a "car" obviously that's a loose definition but anyway my question is would this molecule be any use in that field? if you haven't read about it before its very interesting subject and i read about it years ago they probably improved it a lot more its basically the start of nano tech
In my experience with hydrogenation, using a rubber balloon filled with hydrogen is better so you can keep a constant higher pressure of hydrogen on the solution to increase the yield.
Nile red one of the biggest chemistry youtubers: PD/C can make hydrogen explode if there's air present, but i don't have any nitrogen to flush the apparatus This random guy: I just putted in nitrogen before hydrogen, i'm not gonna even say why.
So I have a suggestion for a video, I know it's been done but if you're looking to do some stuff with established syntheses: Synthesis of Chromyl Chloride. It's a beautiful and interesting compound and also Hella spooky to handle so that should be fun! As a bonus, like me Nigel loves the stuff so there's a decent chance he'll drop by to say hi and you guys can compare your executions of synthesis. Alternative: Bromine! Anyways, thanks for the cool video, keep up the good work!
A probably stupid question. Why didn't he react the ditosilate product with amonia to directly have the amine compound? Isn't amonia a sufficiently good nucleofile?
The formed primary amines (product) can react with the tosyl substrate (especially since primary amine is better nucleophile than ammonia) leading to a whole range of oligomeric products of various lengths.
I'm the student studying organic synthesis on polymers. Could you tell me which program to draw chemical structures on your video I'm a big fan of your videos. 😊
Is the imbalance in charge after locking the potassium in jail enough that you can measure? Wondering if you could use this to make a very terrible, but working battery.
Hi, I've just learned about Tholin, a very interesting stuff which can only be found on other celestial bodies like Pluto (the reddish dust on the surface). Now I wonder if this can be synthesized in a lab. en.wikipedia.org/wiki/Tholin
@@ChemiolisI've always thrown them away when they turned black like that and no solvent would wash it off, but i guess that since no solvent would wash it off actually means that it's probably not interfering with the chemistry you're doing
@@levtrot3041 I haven't found it to be an issue, though they do get clean if you use them for something harsh like a nitric acid synth. Mostly it's just conc. sulfuric acid reactions/tar that end up making it black/brown
@@МатвейБакальский-ъ7ф depends where you are. Can’t buy it in the US as a private person without a business need because some dumbass kid unalived himself with it a couple years ago.
@@TjallieBrrr it stinks, hard to remove from your product, makes me infertile, stinks, and was the solvent in a hard reaction during internships. Also it stinks.
The way to mix a gas is to embody it inside a magnetic field. No gas will rest under a liquid in atmosphere very well. H+ in air (forming HNO oxide-group) causing N2 forming underneath is only effective under a slight magnetic field, in the presence of liquid argon (or another stable hydrogen-field reactant). You probably noticed the earth’s magnetic field depending your yield!
I have been working on a bigger project these weeks that is very difficult to get right, I hope to still get to finish it in the way I want to, but it will probably take a while. At the same time I don't want to upload too little so I will take on some shorter and more established syntheses inbetween. For now, enjoy this potassium prison. Also, ideas are welcome 🙂
Bro, you do amazing work. Do as you need brotha.
Salvarsane, the first antisyphilitic medication. I know you've already had experience with arsenic and it is not as horrible as it is expected to be, just as cyanide (don't eat=everything ok)
Could your cryptand solubilize KMnO4 into some non polar solvent, like toluene or DCM? It'd be a nice test/presentation of your product.
@@Tyresio12 crown ester 18-6 is way cheaper and is capable of dissolving KMn04 in non polar solvent, cryptand is more of a scientific curiousity subject (for making Na anions or other obscure stuff)
Bro, make a pure negative charged liquid by imprisonment of potassium
A little trick that I like to use for hydrogenations like this is opening both valves, letting some hydrogen escape until you hear a change in pitch of the whistling. At that point you know its basically pure hydrogen coming through and all other gases have been purged.
is this ready for combustion
chemiolis is such a chad that he doesn't care about his reaction going yellow
I love the detailed mechanisms and diagrams (like the Pd/C one)! A lot of organic chemistry youtubers will show reaction schemes but not really show mechanisms. It really helps make your content more approachable to someone who isn't super well versed in organic synthesis.
Someone in my lab was using sodium azide for a synthesis, and the procedure he was following called for DCM as the solvent. He didn't tell me at the time and put the residual azide and DCM waste into a labelled P-listed waste container. A few months later, I find this container in the back of his hood... that was a fun call to EHS.
Waste disposal methods are always interesting to see. Especially when there are risks with storing it. As always, there is no one "right" way to deal with it and sometimes seeing something I might do is educational.
Oh, and thanks for another interesting video!
I have been waiting for another of your videos for a long time it seems, thank you so much for making this one sir! I understand that things takes time and i am looking forward to your other projects no matter how they go really.
I worked in a research lab for 3-4 years designing and handling PEG ethers. I see those Tosyl and Trityl derivatives in my nightmares. We made some azide derivatives too but the carbon to nitrogen ratio was well over 3
I love that I actually understand the formulas and naming patterns since my organic chemistry class has started and Im genuinely very interested in it
I found this channel when I started org 2 and oh my lord was it helpful to have something fun to actually use what I was learning on
We love supramolecular chemistry
this is so awesome, I'm a computational chemist/biologist working on chemosensors and their affinity to their ligands, and am literally working on publishing a paper over a type of Cryptand right now, so seeing this video come out from my favorite chemtuber is so cool.
"This chemical shouldn't be handled with more than 5g"
"So anyway we made 20 g of the stuff"
I didn’t know about cryptands, interesting to see compounds similar to crown ethers
Also interesting too the reagents like TsCl being used for actual chemistry, I’ve only ever seem them in textbooks (tbf im a student so yeah)
@@monika.alt197Right? I think it’s pretty cool that the sulfonyl group of TsCl reacted with the alcohol of triethylene glycol in something akin to a nucleophilic acyl substitution reaction. I didn’t know you could do that with sulfonyl groups but it makes sense now.
Great video Sam! Dry packing column, my beloved
Looking at THIS synthesis explains why it is so expensive
You have to be not fucking around as a chemist to have teflon stir bars permenantly stained that shade of brown, I think.
I work with cryptand every day in the lab. It's fun to see you synthesizing something I work with
Realistically, I think these are the best chemistry videos on TH-cam.
You sure do like your chromatography columns though, even if this one wasn't used that way.
Wouldnt it be easier to reduce the azide with PPh3 and directly distill off the product?
If you want a good eluent for the diazide product I used 80% Methanol in DCM, sometimes even 90% methanol in DCM. They REALLY don’t separate well, also I was working with hexaethylene diazide, so maybe it would be easier, or maybe harder, I’m not sure. But I agree, it is frustrating. We usually used excess sodium azide to avoid this.
Excellent video, I really liked the part where you showed the Pt as the catalyst. never seen that before. Insightful video. In lab the best yield I had ever gotten was 85%, had I gotten 80% would've make my professor be happy lol
PEG-3 diazide is actually available for purchase. I wonder how they store it to prevent it from exploding?
I used to work for chemical company that produced crown ethers. I mostly made 18-crown-6, dibenzo 18-crown-6 and dicylohexano 18-crown-6, made by hydrogenating dibenzo 18-crown-6. I worked on a pilot plant scale most of the time.
An explosion at a kilo lab (a lab used for syntheses of chemicals in kilogram amounts for research) in 2008 was believed to be caused by diazidomethane accumulation in a rotavap.
Serious question. Why do you use a cotton for filtration instead of filterpaper (or coffepaper)?
It’s just faster
I know near nothing about chemistry, but those big rings made me think of catenanes, and I always wondered what a catenane polymer would be like. Like a molecular chain.
Hey! Question, though: Did the volume in the balloon decrease after all? I ask, because in more typical hydrogenations it's also hard to track the progress because you can't really tell whether the H2 has been consumed by the reaction or just diffused away through the rubber. But then, if one really wants to be sure, one could just fill a second balloon with H2 and keep it at hand to compare afterwards.
Please make a lab tour video 🥺
When you thought you were beginning to understand, thanks for the presentation
Here is a better way: Starting from your starting reagent of triethylene glycol, do an Albright-Goldman oxidation to the dialdehyde using acetic anhydride and DMSO. Purify by distillation to remove the acetic acid byproduct. Do a reductive amination via a modified Leuckart reaction using ammonium formate and 2 extra equivalences of formic acid. Purify by recrystallization as you do. Only a two pot reaction pathway with very minimal byproducts that are super easy to remove, and most reagents should be inexpensive and readily accessible.
"No more than 5g" ... "the yield is 20 g" :D
Ethylenediaminetetraacetic acid (EDTA) synthesis when?
i read a while ago about people making thins on a molecular scale like a "car" obviously that's a loose definition but anyway my question is would this molecule be any use in that field? if you haven't read about it before its very interesting subject and i read about it years ago they probably improved it a lot more its basically the start of nano tech
In my experience with hydrogenation, using a rubber balloon filled with hydrogen is better so you can keep a constant higher pressure of hydrogen on the solution to increase the yield.
Nile red one of the biggest chemistry youtubers: PD/C can make hydrogen explode if there's air present, but i don't have any nitrogen to flush the apparatus
This random guy: I just putted in nitrogen before hydrogen, i'm not gonna even say why.
So I have a suggestion for a video, I know it's been done but if you're looking to do some stuff with established syntheses: Synthesis of Chromyl Chloride. It's a beautiful and interesting compound and also Hella spooky to handle so that should be fun! As a bonus, like me Nigel loves the stuff so there's a decent chance he'll drop by to say hi and you guys can compare your executions of synthesis. Alternative: Bromine! Anyways, thanks for the cool video, keep up the good work!
Too easy
You should have demonstrated how cryptand can solubilize potassium salts in hexanes (ie potassium permanganate). Would've been a cool demo!!
A probably stupid question. Why didn't he react the ditosilate product with amonia to directly have the amine compound? Isn't amonia a sufficiently good nucleofile?
Maybe using ammonia there's the risk of getting a cyclic product? While with azides it can't happen... I suppose, not sure 😅
The formed primary amines (product) can react with the tosyl substrate (especially since primary amine is better nucleophile than ammonia) leading to a whole range of oligomeric products of various lengths.
I'm the student studying organic synthesis on polymers. Could you tell me which program to draw chemical structures on your video
I'm a big fan of your videos. 😊
What made you choose Pd/C over a Staudinger reaction?
Is the imbalance in charge after locking the potassium in jail enough that you can measure? Wondering if you could use this to make a very terrible, but working battery.
Hi, I've just learned about Tholin, a very interesting stuff which can only be found on other celestial bodies like Pluto (the reddish dust on the surface). Now I wonder if this can be synthesized in a lab. en.wikipedia.org/wiki/Tholin
Amazing job well done how are you
What paper did you use
Short.
Path.
Vacuum.
Distillation.
Its what I always look forward to.
If you can pour it down the drain, does that mean you can throw it on your garden ?
If you don't already, you should keep your used Pd/C and similar catalysts to do a recovery video in the future
Lock him up 🗣️💯🔥🔥🔥
Your favorite chemist < Jean-Marie Lehn
WHY IS THE STIR BAR BLACK??!!
Absorbed tar from all the reactions 😻
@@ChemiolisI've always thrown them away when they turned black like that and no solvent would wash it off, but i guess that since no solvent would wash it off actually means that it's probably not interfering with the chemistry you're doing
@@levtrot3041 I haven't found it to be an issue, though they do get clean if you use them for something harsh like a nitric acid synth. Mostly it's just conc. sulfuric acid reactions/tar that end up making it black/brown
Tosyl chloride... the smell is just really off to me. Its like something familiar but wrong
Wow, white tosyl chloride! Mine is always pink lmao
forbidden crab
Pretty amazing
thanks
"Sodide (illegal)"
Yeah, about right
When are you making azidoazide azide? 😁
Alkali metal anion when
The largesse of using that much sodium nitrite just to dispose of waste hurts me.
It's cheap
@@МатвейБакальский-ъ7ф depends where you are. Can’t buy it in the US as a private person without a business need because some dumbass kid unalived himself with it a couple years ago.
all this to make a half hazard joke aboutotassium being Na-ughty
I hate DMF with a burning passion
Why?
@@TjallieBrrr it stinks, hard to remove from your product, makes me infertile, stinks, and was the solvent in a hard reaction during internships. Also it stinks.
@@0pvo0 damn thats a chemical worth avoiding, did it make you infirtile during an internship!?
That sounds super horrible
@@TjallieBrrr so far I know it didn't, but did I mention the smell?
Careful now , or Nile Red will make some .
Cryptand looks like hmtd (slightly more stable hmtd) and picture with cation of potassium hints at a sequel...
The way to mix a gas is to embody it inside a magnetic field. No gas will rest under a liquid in atmosphere very well. H+ in air (forming HNO oxide-group) causing N2 forming underneath is only effective under a slight magnetic field, in the presence of liquid argon (or another stable hydrogen-field reactant). You probably noticed the earth’s magnetic field depending your yield!
I love you
Thanks from hungary
Lmao lock the the K.
firsr
'promosm' ✅