Making 1,3-Dioxolane
Вставка
- Опубліковано 27 вер 2024
- In this video I am making the solvent 1,3-dioxolane because there was no video on UA-cam about it yet! In general you should add a tiny bit of BHT or HQ as stabilizer against peroxide formation if stored.
Support my channel with patreon: / chemiolis
Awesome including the cost to make it yourself per litre, please do more of this! Makes it more worthwhile to “copy” your synthesis lol
Ah yes, the protection group solvent.
Genius
Incredible! In the end it is just an acetalysation of your prior produced ketone. With a yield of 85% while also having to synthesise the ketone first you are a total legend to me! We had to acetalyse Benzaldehyd with p-TSA and the literature yield was supposed to be 90%. Considering that, your yield is actually insane.
A yeeting mantle
I heard that too
It will be if my synthesis fails
@@Chemiolis thus, it shall be
Always love a good cheap solvent!
The molecule looks like a frog
Froxolane
Ribbit,RibRibRibbit-Froxolane.
The Dimethylamylamine (DMAA, Geranamine) molecule looks like an arm muscle!
I guess it's cool. 😕
You should look at the Sesamol molecule! It's cool! 😎👍
Maybe. 😕
Grab some beers! 😕👍🍺🍺
I want to make beer colored Crystal Speed (EA, Ethylamphetamine), beet colored Crystal Ecstasy (MDEA, 3,4-MethyleneDioxyEthylAmphetamine), and beer colored Crystal Modafinil (Crystal Mod, Modafinil).
Awesome. The dialogue never lags. Great methods and great explanations. Subscribed!
This looks like it would be a great substitute for 1,4 dioxane where you want a bit more polarity but while still being aprotic. You could probably electrolyze alkali metals, alkali earth metals and rare earth's from the salts.
Chemical industry is so massive and has been around for so long that if it actually was beneficial, they would already be using it. Dioxane has the advantage of not being sensitive to acid
not true at all. solvents in process chemistry come and go all the time. remember propylene carbonate, methyl thf etc.? @@christiannorf1680
I really thought you guys were the same person for a moment
@@christiannorf1680 All ethers are more or less sensitive to acid.
Should we stop using ethyl acetate as a solvent because it is both sensitive to bases and acids? No.
Not all solvents work for all reactions, so you use the appropriate solvent.
I would be more interested in its boiling point and the difficulty of removal more than its sensitivity to acid.
If it boils more than 100 °C, then I would not be that impressed.
This is smooth, simple, and clearly explained. good work.
You draw both substitution reactions as an SN2, but they will proceed through an SN1 as the adjacent oxygen can stabilize the carbocation by forming an oxonium ion. Otherwise great video as always!
You're right, they are SN1, I just condense mechanisms as much as possible and never draw SN1 unless it is key to the reaction. In reality it is rarely relevant if a reaction is SN1 or SN2 outside of University.
YOU are underappreciated.
we use this in our electrochemistry lab as a solvent for liquid electrolytes for batteries! Specifically, a 50:50 mix of 1-3 DOL : DME
Wow I thought it would work well as an aprotic lectrolyte, I see that you are really using it as such❤
If only imid salts were less of a pain in the butt
@@christiannorf1680 ain't that the truth haha
@@miiracle7141 Yeah from all what I've seen, including our own work, I'm team LiPF6. And I don't think that will change any time soon
@@christiannorf1680 certainly, it's what we use most. anyone using something else is specifically trying to develop a new electrolyte. most ppl use LiPF6 since they're more interested in the electrode materials
Merry Christmas man!
Never used this once during a 7year career in the lab. Always went directly for THF or dioxane as noted in the video
Same. I only know it as a co-solvent in some modern Li-ion battery electrolytes
Yeah - as people want solvents to be stable, not reactive acetals! THF is reactive enough, let alone this fake solvent.
It is interesting that formaldehyde hydrate readily forms acetal with the ethylene glycol, but not with catechol - I guess it's because of the electronic effects of the aromatic ring...
best synthesist on youtube.
my first thought i had when I saw the structure was that someone decapitated nanokid
it sounds like a pretty decent idea for an article
It is the head of a nanokid
@@MandrakeFernflower rip nanokid
I am re-watching Full Metal Alchemist: Brotherhood, somehow Chemiolis, ThoiSoi, and NileRed uploaded... is it a coincidence? or is December Chemistry month?
Now finish the rest of the MDMA
Lol
simpler procedure than expected! cool
Well, it's less stable towards acid (re- releasing formaldehyde) and likely similarly teratogenic as 1,4-Dioxane. No real reason to use this stuff when 2-MeTHF has a similar boiling point, is way less toxic, and is reasonably stable towards acid. Plus 2-MeTHF is water miscible at elevated temperature, but not so much at RT
The heat-sensitivity of 2-MeTHF’s water miscibility is neat, I can see that being handy for some situations!
Useful, thanks for sharing. NurdRage made the dimethyl version of this when trying to make dimethyldioxane. That was really sensitive to acids, which is something I would expect from this too. Have you tested whether it survives acids?
I believe generally acids hydrolyze these acetals into the carbonyl compound which would release formaldehyde and ethylene glycol in this case. It should still be acid sensitive as the only difference in NurdRage's video is just the use of acetone instead of formaldehyde (I presume).
That's also something I always wonder when coming across 1,3-DOL. If I recall correctly acetals are even more sensitive than ketals. Perhaps that's the reason it has not been widely adopted
@@christiannorf1680 That and the lower boiling point.
I know that formaldehyde forms an adduct with sodium bisulfite, but does it react with SO2 in this conditions? Can SO2 therefore act as a catalyst in the reaction?
Can dibromomethane or DCM be used instead of paraformaldehyde? Then, requirement of acid is not required, base can neutralize the HBr (or HCl) which is kicked out
they're not very reactive and rather expensive compared to paraformaldehyde
the eblicatoral oxain of the endromic simplicall sinquelled its saleen sangularity into the grebalescent galbonic aclatate of a single ensogratic!
I mean, would be fine in basic conditions, but acidic conditions seem sketch. Will have to check back when I finish the video to see if this is covered.
7:40 "I set it up for destillation" dude are you outsourcing your videos?!
The whole "I set it up for ✨️short-path (vacuum)✨️destillation"-thing is your signature pharse ;[ you can't just not say it
Can you tell something about dioxolane hazards ? It is high explosive or does it form explosive peroxides as diethyl ether ? What about the smell ?
Never heard of this,i dont understand why this is better than dioxane
Should be more polar due to the geometry. I. e. better at dissolving polar stuff
I wonder it it can be a Girgnard Solvent. That would be a great alternative to THF/Et2O
Likely not. It's so close to dioxane, which gives you the schlenk equilibrium product which precipitates out. I have never read of dioxane being used to form the grignard before its addition, and is always added afterwards to get the dialkylmagnesium compound.
@@morningstarsci Interesting, thanks for the response. Do you think it has to do with the O-lp into the C-O sigma* donation inhibiting coordination?
It's worth trying. If you want a fancy and easy made Grignard solvent, read about methylal. Methanol, paraformaldehyde, calcium chloride, and a little bit of HCl produce azeotrope of methylal and methanol in high yield. The smell of it resembles chloroform but is... lighter I would say?
I presume it's also peroxide-forming like THF but probably not to the same extent as diethyl ether, right?
Yes, should add some BHT if stored for a long time
Interesting compound. The ingredients may only cost a few Euros, but what about the labor costs?
You seem to love short path destillations
I love it until I have a rotovap
electroboom: full-bridge rectifier
chemiolis: short-path distillation
You should do 1,4-dioxolane it's the same but better
Don't let IUPAC tell you what to do!
Please can you make video on making Hedione molecule thank you 🙏 ❤❤❤❤❤
Finally, a video with few simple steps, not multiple staged synthesis. Other videos are also great but after some point, I just loose it ;)
But I wonder what else can we use it for other than as a solvent? Like can it be modified to be used as linking agent similar to glutaraldehyde?
Anyways, I think I should look for some chemicals like this and glutaraldehyde to make more aminated chitosan since I mainly work with it hahaha. I use glutaraldehyde and then apply ammonium solution and it works to some extent but it is very reactive and I am not sure if both aldehyde groups react and get consumed by amine groups of chitosan 🤔
Make new RC drugs replacment (for research p only)
Is 1,3-Dioxolane ether?
Since organic chemistry is witchcraft for me: this whole theoretical reaction mechanism stuff... is that some a Single Person does during a phd? Is that too much? Stuff Masters students can do as like research worker? How does that work?
mechanism drawing is both easy and hard. once you understand how the molecules interact, you can write the mechanism and vice versa, but it may become complicated AF. I strongly recommend the Clayden book, it's remarkably easy to read yet covers most of the topics you stumble across while learning organic chemistry
@@dimaminiailo3723 but don't you have to prove that these intermediate products really exists for your mechanism to get recognized by other organic chemists as a legit Mechanism of what happens?
A lot of it is just smart guessing since the mechanisms frequently aren't known for sure. In principle, you always have to have something that wants to lose electrons and something else that wants to accept additional electrons. Then you just draw arrows that show how the electrons - usually as pairs - move around.
@@hammerth1421 Yes, but that guessing is better than not having one. Several mechanisms can lead to either the same or different product, which often turns up to be a side one. While the curved arrow may not predict all things happen, it's still a reliable punching bag for one's mind
Hard to generalize. It can be. Depends on what the group is working on. If the reaction is important (e. g. for chemical industry) figuring out the mechanism can help prevent side-products from appearing. If it's a fancy new reaction, then understanding the mechanism is mostly "for the science".
One example from my previous group was that in a reaction instead of the expected outcome, the molecule rearranged and formed a three-membered ring (which was hard to figure out in the first place). So we sat down and began drawing possible mechanisms that would lead to the product we observed. That process is based on what we know from the hundreds of thousands of different reactions reported in the literature. Basically why we learn organic chemistry: To be able to figure out how reactions work and be able to design them to make the stuff we need.
Then again, depending of the level of interest, one could dig deeper and for example try to catch intermediate products from the mechanism or use starting materials that should prevent the product from forming etc.
Why did you use a cotton insulation rather then the standard aluminum foil?
Would trioxane work in place of paraformaldehyde? it would technically need slightly more water, but the trace amounts should still be enough right?
it should work as well, although I'd rather use paraformaldehyde
Makes great smells?
Man what is the name of that mantle thing you use, I have a hot plate but need a mantle adaptor thing like that
It's called DrySyn from Asynt, there are similar ones like Heat-On from Heidolph
Could i recreate with my aq formaldehyde with some tweaking or should i just order some paraformaldehyde?
paraformaldehyde can be made from formalin. neat formalin is aqueous and water isn't going to make the yield higher, so it should be substituted with paraformaldehyde
Can you do research on Dicyanine A, 98%? can you make 99%?
using SO2, have you no respect for your neighbours 😂. I totally would have used regular old sulfuric acid, no difference in reactivity and you can still get rid of the SO4 by precipitation later on. PS. you can use a base bath or acid bath for cleaning your glassware overnight.
Could you make Francium, and drop it in water before it becomes inert? You may need to run or hide behind something when it touches the water, it could do anything from sizzling lightly, to blowing up catastrophically. Thanks
Is 1,4-dioxane polar or non polar
yes
Taste test?
"Kurger Bing"
sleeper build
Yeah but how tasty is it?
great
so jealous you can get 10l of sulfuric acid for just 40 bucks
europe moment
In Russia
I bought it like 2 years ago so it’s more expensive now :-)
@@Chemiolis the ability to buy it at all is worth gold. I don't know why they make it so hard for us around here. If someone really wants it, they will get it, just with more work.
If you are in the US virgin sulfuric acid can be bought as drain cleaner.
@@y33t23 Aren't most commercially available battery acids just nearly pure sulfuric acid?
Like this comment
Great video thanks for sharing
finally giving that bad boy dioxolane some highly deserved appreciation!
Water, the universal solvent
Nice recovery from the overflow. It looks like it almost could have been a gag. Way to go man. You’re the best UA-cam chem and probably really fun to hang with at parties. Really, thank you for this wonderful content!
I would like you to dub the video in Portuguese, so I can share your videos with my Brazilian friends
This is good stuff. The fact that it distills below 100 celsius makes purification easy. If i wasn't already subscribed this would have earned that sub.
We use a ton of NMP at my job as a cleaning agent and photoresist stripper. The problem with using dioxolane as a substitute is its BP is way too low.
Awesome, I'll take 25 gallons, wheee! But please don't get a whiff of free formaldehyde! I toxic as hell....hey, what's it smell like, and is 8t stable to LAH and other reducing agents?
Should be perfectly stable against reduction like other ethers. Acids (acetal) and oxidants (ether) may however be problematic