This one is for all the homechemists out there, finally something u can replicate ;) Support my channel with patreon: / chemiolis Support my channel by becoming a member / @chemiolis
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)
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 ..
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
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.
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.
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.
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!
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 !
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!
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
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
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.
Your yields are always great. Very satisfying unlike most other chemtubers . Your yields are always great. Very satisfying unlike most other chemtubers .
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.
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
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 :)
Btw if you really want strong bleaching that actually works, try powdered pool chlorine diluted in a bucket of hot water, then dip the clothes in it for a few minutes, then rinse thoroughly to get rid of the excess chlorine, otherwise it will start to attack the fabric and it will make it break apart very easily.
Concentrated sulphuric and nitric acid are not "home chemistry" in most of Europe. They're on the list of explosive precursors and you can't buy them unless you're a professional. There are even no common products containing them... BTW, the same problem with hydrogen peroxide, max. 12% :/
Not all bleach is "slimy". It's available in that form to reduce splashing, so you don't end up with white spots all over the clothes you were wearing when you added it to the washing machine.
I'm not super sure how good I would feel about trying to distill over the di and trinitro mesitylenes. I could be wrong but something tells me that those two extra methyl groups aren't going to make a big difference between trinitromesitylene and its cousin, trinitrotoluene. -edit Wow. That is an insane amount of work. Kind of an "uh-oh" moment when you have a yield that has to be separated by column chromatography.
I'm not sure why Bechamp reduction fell out of favour. I used it on a number of arylamine substrates during my PhD and it almost always gave 95%+ yields. Because the yields were always so high, there were very low levels side products. I was normally able to simply extract, filter and then recrystalise my products to obtain high purity samples (again with yields upwards of 95% isolated). Before going the Bechamp route, I tried the more common hydrogenation over Pd/C but it consistently gave more impurities and lower yields. There were a few times where I had low yields but it was always because I produced too much fine iron(III) oxides that seemed to love forming an emulsion, trapping product, blocking filtration and becoming a nightmare to extract. Once I got the hang of it though, it became very reliable.
I love how it's just like serious chemistry, then out of nowhere "it becomes as white as my ass in winter" xD love it. If teachers were allowed to talk like that, maybe there'd be more nerds 🤔
Pretty cool video! And dude, you seem to absolutely love your short path condenser xD Is this just because you don't have a rotavap, or is there something else?^^ And I like the difference from Tom to you: Tom: "Yellow chem bad" You crazy dutch chemist: "Just go directly to black tar and extract your pure product! Problem solved!" 😂👌 Edit: Oh and congratulations on your absolutely perfect yield of 100 %! From one off white sock to one orangy sock. Amazing. Amazing. Wow^^
An alternative approach could potentially combine step 2 (Bechamp process) and step 3 (oxidative coupling) by coupling both in a reduction process going via an azoxy-intermediate (coupling of nitro- with amine-compounds).
You can find various methods in the following book chapter or by googling for "nitro amine azoxy coupling": "2.7 Reduction of Nitro Compounds to Amines, Azo Compounds, Hydroxylamines, and Oximes, and Reduction of N-Oxides to Amines" DOI: 10.1055/sos-SD-227-00139 (p.340ff) (from "de Vries, J. G.: 2018 Science of Synthesis, 2017/6: Catalytic Reduction in Organic Synthesis 2")
e.g. this one: "Preparation of symmetric and asymmetric aromatic azo compounds from aromatic amines or nitro compounds using supported gold catalysts" DOI: 10.1038/nprot.2009.242
You could cool the sulfuric acid and nitric acid mixture before addition below room temp. That would probably suffice to keep the temps of the reaction mixture low.
Could potentially get the temp lower during the acid addition by adding a condenser between the addition funnel and reaction flask and run chilled coolant through it. This way, the drops that actually reach the reaction are ice cold, or colder! (In theory, you could run it lower than 0c, since the acids are not even close to freezing at this temp.) Also, how many kiloliters of ethyl acetate do I need to do this exactly?
As an operator of a public water system, bleach is my life. Everyone's indoor plumbing would become contaminated with bacteria and they'd all get sick. I'm actually heading out the door now to buy another 55 gallons.
i dont really think that vaccum short path distilation is home chemist friendly tho... xD Good synth tho, keep it up. Never knew you could make aromatics from acetone.
If I oxidize mesetylene to it's respective tricarboxylic acid and then react it with a strong base under heat, will it form benzene? Then that would mean I can make benzene from acetone!
I think u can get some azodye by just mixing aceton and ammoniaque, after a moth or so u get some red liquid that smels afule and has a strange yello phase. Idk i made it 2 mothes a go and now its just siting on my desk, witch is stubid becaus u can still smell ammoniaque and if it is some kind of azody its canceres to
Couldn't you just let the Amine react with nitrous acid and HCl to form the diazonium Salt and let this Salt react with Mesitylene? Could be a little bit easier
There was no lit on that for this one. It is said that this type of reaction would require an EDG on the second aromatic so for example the mesitylene phenol or a second aniline. The diazonium attacks on the para position of the mesitylene-EDG but this is already substituted with a methyl. Either way we would not get the azomesitylene like this if the second mesitylene also requires an EDG (and then question is if the reaction proceeds at all, same for bare mesitylene). Second issue is that sodium nitrite is restricted coz people use it to end themselves
"Copper-Catalyzed Aerobic Oxidation of Anilines to Diazenes" (compacter description as used in book chapter below) DOI: 10.1002/anie.201001651 You can find this and alternative methods in this book chapter: "11 Oxidation of Amines and N-Hetarenes" (from the book: "Muniz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis") DOI: 10.1055/sos-SD-225-00339
Cool video. I have absolutely no idea why I'm watching chemistry videos though 🤷🏻♀️. EDIT: oh, apparently it's even at least the 2ne time I'm watching this 🤷🏻♀️ 🤷🏻♀️ .
This video differs from previous videos. This video is fast and has a lot of content..... It would have been better to divide this video into four parts.... so that the commentary would be slow, understandable, and not boring..... Greetings to you
@@lithiumferrate6960 It was also already described in 2010 here: DOI: 10.1002/anie.201001651 You can find this and alternative methods in this book chapter: "11 Oxidation of Amines and N-Hetarenes" DOI: 10.1055/sos-SD-225-00339 (from "Muniz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis")
@@Chemiolis An alternative approach could potentially combine step 2 (Bechamp process) and step 3 (oxidative coupling) by coupling both in a reduction process going via an azoxy-intermediate (coupling of nitro- with amine-compounds). You can find various methods in the following book chapter or by googling for "nitro amine azoxy coupling": "2.7 Reduction of Nitro Compounds to Amines, Azo Compounds, Hydroxylamines, and Oximes, and Reduction of N-Oxides to Amines" DOI: 10.1055/sos-SD-227-00139 (p.340ff) (from "de Vries, J. G.: 2018 Science of Synthesis, 2017/6: Catalytic Reduction in Organic Synthesis 2") e.g. this one: "Preparation of symmetric and asymmetric aromatic azo compounds from aromatic amines or nitro compounds using supported gold catalysts" DOI: 10.1038/nprot.2009.242
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. 😒
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)
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.
I like how at the end you have never used bleach, yet you have all these chemicals, and even better you had to ask your mom for bleach when you have all these dangerous chemicals. The bleach you used isn't that good, especially for chemistry, I always try and go for the stuff without any impurities like surfactants, colors, and smells.
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.
![Making [1.1.1]Propellane](http://i.ytimg.com/vi/iTlRvQuIyqE/mqdefault.jpg)
Really cool chemistry. Had multiple years of organic chemistry and never heard that you could get a C6 ring from decomposing Acetone
I know right!
Forbidden benzene
@@That_Chemist My words exactly, before I saw this comment. 😂
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)
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 ..
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
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.
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.
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
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 !
3:30 Tar reaction mixture, yellow distillate. Perfect for Tom from Ex&F to see.
also, terrible yields, dodgy syntheses, and nitrations
Really enjoyed you having more fun with the commentary on this video - great work on refining the nitration step also!
"Creates enough heat to sustain nuclear fusion" 🤣
Omg, I admire your patience with this reaction! Awesome!
Epic video, acetone dehydration is quite cool.
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
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
Your yields are always great. Very satisfying unlike most other chemtubers 💀
The stir fish in the dish of socks though 😄
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.
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
Your yields are always great. Very satisfying unlike most other chemtubers . Your yields are always great. Very satisfying unlike most other chemtubers .
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.
God your videos are great. And your dry humour gets me every time.
I love the way you say Iron!!
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
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 :)
Btw if you really want strong bleaching that actually works, try powdered pool chlorine diluted in a bucket of hot water, then dip the clothes in it for a few minutes, then rinse thoroughly to get rid of the excess chlorine, otherwise it will start to attack the fabric and it will make it break apart very easily.
Concentrated sulphuric and nitric acid are not "home chemistry" in most of Europe. They're on the list of explosive precursors and you can't buy them unless you're a professional.
There are even no common products containing them... BTW, the same problem with hydrogen peroxide, max. 12% :/
Where there is a will there is a way. You can still distill sulfuric acid and make nitric
@@Chemiolis That's the home chemistry spirit! 😄
"It turns as white as my ass in winter". I was not expecting that. 🤣
Cant be 100% sock-yield if you burned it right?
its 100% BRSM
100% yield calculated from burned sock ;)
I would love to see you make sodium metal using nurd rage's synthesis!! I haven't sent anyone else do it yet besides him
I have a video on that already, see Sodium metal from Sodium hydroxide
when my old socks start looking like that they're carcinogenic too, but it's all natural baby (:
Not all bleach is "slimy". It's available in that form to reduce splashing, so you don't end up with white spots all over the clothes you were wearing when you added it to the washing machine.
I'm not super sure how good I would feel about trying to distill over the di and trinitro mesitylenes.
I could be wrong but something tells me that those two extra methyl groups aren't going to make a big difference between trinitromesitylene and its cousin, trinitrotoluene.
-edit
Wow. That is an insane amount of work. Kind of an "uh-oh" moment when you have a yield that has to be separated by column chromatography.
I'm not sure why Bechamp reduction fell out of favour. I used it on a number of arylamine substrates during my PhD and it almost always gave 95%+ yields. Because the yields were always so high, there were very low levels side products. I was normally able to simply extract, filter and then recrystalise my products to obtain high purity samples (again with yields upwards of 95% isolated).
Before going the Bechamp route, I tried the more common hydrogenation over Pd/C but it consistently gave more impurities and lower yields.
There were a few times where I had low yields but it was always because I produced too much fine iron(III) oxides that seemed to love forming an emulsion, trapping product, blocking filtration and becoming a nightmare to extract. Once I got the hang of it though, it became very reliable.
You should do TEMPO from acetone too! The first step involves treating acetone with gaseous ammonia iirc.
I love how it's just like serious chemistry, then out of nowhere "it becomes as white as my ass in winter" xD love it. If teachers were allowed to talk like that, maybe there'd be more nerds 🤔
Dude you're going to be huge some day!
he's gotta take life one sock at a time
@@That_Chemist I guess there's not really any other option now that the other sock is carcinogenic..
Pretty cool video! And dude, you seem to absolutely love your short path condenser xD Is this just because you don't have a rotavap, or is there something else?^^
And I like the difference from Tom to you:
Tom: "Yellow chem bad"
You crazy dutch chemist: "Just go directly to black tar and extract your pure product! Problem solved!" 😂👌
Edit: Oh and congratulations on your absolutely perfect yield of 100 %! From one off white sock to one orangy sock. Amazing. Amazing. Wow^^
Are you using nitrile gloves while hand-dipping a sock into a solution of a carcinogenic azodye in DCM? In any case, love the channel!
*cries in living in a very controlled place where you can’t find anything* 😢
An alternative approach could potentially combine step 2 (Bechamp process) and step 3 (oxidative coupling) by coupling both in a reduction process going via an azoxy-intermediate (coupling of nitro- with amine-compounds).
You can find various methods in the following book chapter or by googling for "nitro amine azoxy coupling":
"2.7 Reduction of Nitro Compounds to Amines, Azo Compounds, Hydroxylamines, and Oximes, and Reduction of N-Oxides to Amines"
DOI: 10.1055/sos-SD-227-00139 (p.340ff)
(from
"de Vries, J. G.: 2018 Science of Synthesis, 2017/6: Catalytic Reduction in Organic Synthesis 2")
e.g. this one:
"Preparation of symmetric and asymmetric aromatic azo compounds from aromatic amines or nitro compounds using supported gold catalysts"
DOI: 10.1038/nprot.2009.242
10:44 I'd put the acid in the flask and cool it to 5 °C and add (preferrably) prechilled Mesitylene to the flask via dropping funnel
the outro had no business being that funny
You could cool the sulfuric acid and nitric acid mixture before addition below room temp. That would probably suffice to keep the temps of the reaction mixture low.
Could potentially get the temp lower during the acid addition by adding a condenser between the addition funnel and reaction flask and run chilled coolant through it. This way, the drops that actually reach the reaction are ice cold, or colder! (In theory, you could run it lower than 0c, since the acids are not even close to freezing at this temp.)
Also, how many kiloliters of ethyl acetate do I need to do this exactly?
I love the way you say mesitylene
Its usually better to create the nitration acid first cool it and add the edukt via a dropping funnel
Dang everyone bling bringin with short paths and rotovapes
Correction! Only a 50% yield ! Unless you are a monopalegic . One sock is as useless as a one legged man in a butt kicking contest! Pun intended 😂
Any guess on what the unknown yellow compound could be?
The ghost of extractions and ires past, present, and future?
@@neb_setabed hahahahahahahaha
trash
How did you manage to get 50% peroxide as a home chemist? I can barely get 15% without needing a specific permit.
18:25 that caught me off guard
Have you just made also socks peroxide? Anyway nice, keep doing
As an operator of a public water system, bleach is my life. Everyone's indoor plumbing would become contaminated with bacteria and they'd all get sick. I'm actually heading out the door now to buy another 55 gallons.
It's possible to use calcium metal instead of sodium?
Does anybody have the whole procedure because I need it for school. They wont just accept this procedure for a source.
This guy never used bleach. How does he clean the toilet? With a stir bar? a short pass distilation tube? a fractionation column?
You could maybe chlorinate the mesitylene and then react it with ammonia to form mesitylamine
0:33 I think you meant to write Ru for Ruthenium for the Grubbs catalyst
i dont really think that vaccum short path distilation is home chemist friendly tho... xD Good synth tho, keep it up. Never knew you could make aromatics from acetone.
If I oxidize mesetylene to it's respective tricarboxylic acid and then react it with a strong base under heat, will it form benzene? Then that would mean I can make benzene from acetone!
A very beautiful carcinogenic sock. Made with 100% anhydrous humor.
wow you improve montage congrat
Can I use lithium metal?
I think u can get some azodye by just mixing aceton and ammoniaque, after a moth or so u get some red liquid that smels afule and has a strange yello phase. Idk i made it 2 mothes a go and now its just siting on my desk, witch is stubid becaus u can still smell ammoniaque and if it is some kind of azody its canceres to
I thought this was a Nile Green video about a c*m sock.
amazing to see a chemist trying to bleach a piece of clothing
After bleaching, peroxidizing and heatgunning them, these socks must be pretty clean and sterile. Your mom should be proud.
Couldn't you just let the Amine react with nitrous acid and HCl to form the diazonium Salt and let this Salt react with Mesitylene? Could be a little bit easier
There was no lit on that for this one. It is said that this type of reaction would require an EDG on the second aromatic so for example the mesitylene phenol or a second aniline. The diazonium attacks on the para position of the mesitylene-EDG but this is already substituted with a methyl. Either way we would not get the azomesitylene like this if the second mesitylene also requires an EDG (and then question is if the reaction proceeds at all, same for bare mesitylene). Second issue is that sodium nitrite is restricted coz people use it to end themselves
I should probably wash my white socks with bleach if those are grey socks...
I also lose my tan during winter.
What's the name of the copper bromide catalyst reaction?
"Copper-Catalyzed Aerobic Oxidation of Anilines to Diazenes" (compacter description as used in book chapter below)
DOI: 10.1002/anie.201001651
You can find this and alternative methods in this book chapter:
"11 Oxidation of Amines and N-Hetarenes"
(from the book: "Muniz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis")
DOI: 10.1055/sos-SD-225-00339
@@realedna Thank you.
The iron gets oxidised, not reduced 😉
shit
Happens to the best of us
Hi, can you reply? I use chemdraw js
Cool video. I have absolutely no idea why I'm watching chemistry videos though 🤷🏻♀️.
EDIT: oh, apparently it's even at least the 2ne time I'm watching this 🤷🏻♀️ 🤷🏻♀️ .
Could you do a steroid synthesis? Maybe drostonlone enanthate
Sadly, making chloroform from vinegar and salt is the biggest thing I can possibly make since I only have vinegar, water and salt from the see😢
You’re content is getting so juicy!
This video differs from previous videos. This video is fast and has a lot of content..... It would have been better to divide this video into four parts.... so that the commentary would be slow, understandable, and not boring..... Greetings to you
'crystals'
Can someone link me the CuBr catalyzed reaction. Seems interesting.
doi.org/10.1039/C4RA00749B
@@Chemiolis Thank you so much.
@@lithiumferrate6960
It was also already described in 2010 here:
DOI: 10.1002/anie.201001651
You can find this and alternative methods in this book chapter:
"11 Oxidation of Amines and N-Hetarenes"
DOI: 10.1055/sos-SD-225-00339
(from "Muniz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis")
@@Chemiolis
An alternative approach could potentially combine step 2 (Bechamp process) and step 3 (oxidative coupling) by coupling both in a reduction process going via an azoxy-intermediate (coupling of nitro- with amine-compounds).
You can find various methods in the following book chapter or by googling for "nitro amine azoxy coupling":
"2.7 Reduction of Nitro Compounds to Amines, Azo Compounds, Hydroxylamines, and Oximes, and Reduction of N-Oxides to Amines"
DOI: 10.1055/sos-SD-227-00139 (p.340ff)
(from
"de Vries, J. G.: 2018 Science of Synthesis, 2017/6: Catalytic Reduction in Organic Synthesis 2")
e.g. this one:
"Preparation of symmetric and asymmetric aromatic azo compounds from aromatic amines or nitro compounds using supported gold catalysts"
DOI: 10.1038/nprot.2009.242
Making ESO e super
0:14 No amateur chemist in the EU is allowed to buy, have or use conc. sulfuric or nitric acid...
The Netherlands are in the EU, too, aren't they?
"all footage was recorded in international waters" ;)
Easy
⌬
BOOM
EARLY
please just make videos about synthesis of nootropics at home
I hear meth is a nice nootropic, and easy to make!
first.
Thanks for sharing awesome video
Sulfuric acid >15% - forbidden in the do-gooder EU.
Nitric acid >3% - forbidden in the do-gooder EU.
I hate my continent -.-
Chemiolis has a European accent, where is he based?
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.
"creates enough heat to sustain nuclear fusion" 😂
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
I may or may not have done this when running a titration that required powered stirring.
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)
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.
Easily your best video yet. Hope it does well so it encourages you to make more long-form content! :)
I like how at the end you have never used bleach, yet you have all these chemicals, and even better you had to ask your mom for bleach when you have all these dangerous chemicals.
The bleach you used isn't that good, especially for chemistry, I always try and go for the stuff without any impurities like surfactants, colors, and smells.
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.