Drying Dioxane with Sodium and Potassium
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- čas přidán 4. 05. 2019
- Following on from our Dioxane synthesis from ethylene glycol, we need the dioxane real dry. So I break out some terrifying looking alkali metals. I also smash some glassware, have an explosion and get things wrong a lot.
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"A running joke with myself."
That's why I come here.
This is by far my favorite DIY tar production channel. Keep up the great videos!
More tar every fortnight!!
this Channel will sink big Oil just yet! we can make our own sludge!!
(hahi'mfunny)
"Chemistry is the devil's work, and yellow is the devil's color"
T-Shirt idea.
yes yes, make this a thing
@@m.ibrahim_2501 I'll chuck this into the discord then, making a new account because I dun goofed on the login.
Kinda reminds me of hunter s thompson, just reading it.
See, the benefit of doing chem in a room with a rug is that I never break my glassware when I drop it. The down side is that I'm doing chem in a room with a rug...
Hmmmmmmmmm, an interesting trade off
This should be top comment imo!
@@willynebula6193 , agreed. Maybe an area rug would work too? That way if something happens, it can be quickly removed and disposed of.
@Anonymous Anonymous
Depends on the rug but yes, that's quite likely considering that a rug has a lot of thin fibers all over the place.
Have you considered an AsBeStOs RuG?
You: I'll just distill this impure chemical
Chemistry: Tar very much.
I feel you with those tar struggles mate, my organic research at uni seems to be research on how to make fluorescent goop instead of actual compounds. I had a carbon 13 NMR turn out like a mass spectrometry spectrum. 😐
Yeah those reactions that just want to produce nonsense... pure chemicals in and organic tar-pit out. Feels bad
@@ExtractionsAndIre
It’s been a year since this video but “tar...tar never changes.” And on that subject, my dad and I are both in medicine, and he has a saying about pus, that I propose you steal for chemistry and tar: “Pus can be neither created nor destroyed, only transferred.” You never know when it comes from, but it always keeps coming (that’s what she said).
Sidenote: a wound with pus in it is described as a “purulent wound”. I know that because they got upset when I charted that the patient had a “pussy wound. “
🤷♂️
Something interesting I learned in either my ochem class or from my PI (I cant remember) is that molecular sieves actually get solvents MORE dry than alkali metals.
Here's the paper pubs.acs.org/doi/full/10.1021/jo101589h?src=recsys
But you have to do it kind of right. Don't just yeet a bunch of 2 year old unactivated molsieves in there; that's kind of ehm... pointless really.
Yeah you really have to activate those sieves. In my lab we just microwave them at 20sec intervals until they're super hot. Then cool them in a dryrite chamber and use em right away.
The thermometer that was reading high was probably reading some off the bottom of the beaker so it might not be off by much. The others were definitely jacked if they were reading low. Same concept to keeping a candy thermometer off the bottom of whatever pot or pan you happen to melt sugar in.
Dear Sir from the Southern Hemisphere, I have been watching you with great interest. You are Single-handedly renewing peoples interest in chemistry, I applaud you and wish you the best in your endeavors. I will continue to watch, and learn from you. You’ll make a great teacher, or professor, or industrial magnate of the chemical industry. But, to be sure, never give up your wonder of the world of chemistry, and science in general. I remain, your servant William Ackley, Texas.....
I feel your pain with those molecular sieves. I always activate them before using by heating them to 300 celsius or something like that for a few hours. I dont remember the specifics. It seems like they never work straight out of the bottle. I also always test them before use. Just make a little pile in your hand and drip a little water on the pile. It should get so hot it burns your hand of course dont hold onto them but then you know they are going to work at least.
yeah, the way to go with sieves. also washing them before drying to remove the dust and other crap.
put them in a RB flask, apply vacuum and heat mildly with a heat gun. I always do that in a RB schlenk flask
I was always taught to clean and activate your molecular sieves! Good tip knglaser!
And store them in an airtight tin with a good lid. Moisture is everywhere.
Sitting down to my lunch of rice & beans (yellow from the curry powder btw) and finding a new ~20min E&I vid is the best
yellow food is okay, i'll allow it
Funniest chemistry channel on CZcams!
Keep up the shoddy work :D
You should definitely activate your sieves before using them. I usually reflux in KOH or CaH2 distill over and THEN store over activated mol sieves.
Buy more chinese thermometers.
Enough chinese thermometers with known distribution of error should work as a good thermometer.
@@thegreatestdane8978 Not pattern per se but a distribution for sure.
Oi mate, buy some more of those thermocouple thingies!
Thanos profile picture
I've enjoyed your presentation. What a hoot!
I really love you, Tom ! I feel like you´re one of very few people who have the same kind of life. I´m talking about the 01:50 . It´s so accurate for my life.
13:50 Well sodium rips off the fluorine right? Look on the bright side, you will have a graphite stir bar, that's more inert and temperature resistant! :p
Layer the floor with those foam puzzle pieces that helicopter parents use to make sure their kids never know hardship, cover it with large squares of tarp from Bunnings, staple around the edges of the tarp with some Big Boy Staples.
You’ll find other ways to destroy your glassware but it won’t be from dropping it.
Microwave thy sieves!
5:36 obligatory you call that a knife reference here
i see you've played knifey-spoony before
Great video!
I really hate those alcohol thermometers. They have never been accurate enough for me.
Hard to find now but buy some nice large range/high temp mercury thermometers.
Extractions&Ire cleans dioxane with sodium. Nurdrage cleans sodium with dioxane
Ideally you want some benzophenone there; to form the ketyl to see when you're done drying. The ketyl is faster to form, and more reactive too.
OI
DON'T TALK SHIT ABOUT MY FAVOURITE CONDENSER
For your next drying you could invest in some acetophenone it's a great indicator for drying solvents with sodium.
By the way Graham condensers work great as long as they are vertical and the material that is been condensed is not viscous. The tip of the hat and a smile, Bill from Texas
ALL CHEMISTRY GOES YELLOW IN THE END
SUCH BOLD PESSIMISM
I love your videos
Hey Tom, quick suggestion. Mol sieves tend to work better if you heat them (e.g. with a propane torch).
There is nothing quite like using an old steak knife for advanced chemistry purposes.
Couple of months ago I discovered that my fumehood at work only pulls air on the bottom when I was quenching sodium. It had plenty of time to mix in with the air in the top part of the fumehood before eventually going up in one huge and quick fireball. Nothing broke and nobody was hurt (except my ears a little) but man... not cool. That's what you get for assuming your safety equipment to work as intended... First time in 5 years of daily lab work that quenching sodium was a problem
What do you use to cool your condensor antifreeze? is it just precooled in the freezer before use or cooled during use?
Do your chemistry on the ground, then the glassware can't fall from a height from which it will break, you also might hurt your back setting it up and die from buildup of fume, but at least the glassware is okay.
@7:35 glad you're okay thats crazy
Have you gotten new thermocouples?
“You only live once.” *in molten alcaline metal*
To predry ethers its a good idea to first mix them over some potassium hydroxide for a couple days, than distill it over and dry further with alkalai metals. Makes for a really dry solvents.
i've been wondering what those stir bars are made of
Fuck me, Potassium is fucking scary, glad you're not hurt
Dude. Dry it with an anhydrous salt. MgSO4 is likely the easiest. You clearly have CaCl2. Or anhydrous gypsum Na2SO4 would probably be best, and you could reuse your byproduct from nitric acid synth. Then sieves (oven them first!), then alkali metals (or hydrides, I like CaH2). Then distill.
Drops glass cusses and scares sailers
14:05 made me laugh.
You are so fucking cool mate.
The antifreeze you started with was diluted with water and had additives. You need concentrate antifreeze for use with semi-trucks. It will have fewer additives and no water.
If you have something with lots of water, you can remove (most of) it by distilling it out as some lower boiling azeotrope. Just add a suitable third solvent to distill it off with water. Especially with devices like Dean Stark apparatus that is a very usefull method.
I was sure it cannot be high water azeotrope at first distillation. If it had something like 10% or more water, it would have reacted quite violently with water.
To reduce explosions you may want to invest in some kind of gas. Nitrogen should be pretty cheap and no hydrogen explosions (nor side reactions due to air oxygen) in nitrogen atmosphere. Heavier gasses like Argon are way better but not as affordable.
If you ever want to remove unreacted sodium, you can often add a bit of ethanol (for slow reaction) or methanol (for a bit faster reaction).
Like a proper ‘Stralian an O was added to the waste name on the bottle.
Hey, can you give some technical advice on how to remove peroxides/prevent peroxide formation in dioxane and ether, ethers in general? would be nice to not blow my head off
Store them over strong bases. Preferably group I alkali metals.
I like wearing the pink and the YELLOW gloves.
Who are you and where is Tom?
Yellow chem bad, but yellow *gloves* good (or okay at worst lol, I prefer blue)
5:07 would it be different if it was contained in an amber jar ?
That cheese with oxide shell looks tasty
Did you buy the thermocouples? ... Shit did any one wake up Billy Joel armstrong this year?!
where did u get the K and Na from
Sooo... Did you know molecular sieves are *completely useless* if you don't dry them first?
I mean, maybe they were dried at some point, but if they're stored in that not-so-airtight plastic container with a wide screw-on lid, it won't take long for them to soak up moisture from the air!
That would explain the hydrogen explosion you got.
And the running gag about chemistry that involves those sieves failing and not making it to youtube.
In fact, at 16:16 they may even be putting _more_ water back in your dioxane...
I did actually end up drying dioxane just like you did once, with sieves and potassium! I dried my sieves at 225°C under vacuum (maybe overkill, but hey...), added the dioxane, left it stirring overnight, and transferred it the next day in a flask with a potassium mirror. I barely got any potassium reacting away.
(Sadly, the only thing I ended up using that dioxane for was to check whether my nickel salts (chloride and bromide) were soluble in it. They werent. I suddenly had no use for that carefully dried dioxane anymore...)
Also, speaking of yellow potassium, did I ever tell you about that one time I ended up playing whack-a-mole with flaming beakers? ^^
Where I studied we used dried sieves *after* refluxing w/alkali metals, because sieves are supposed to shift the equilibrium further than metal + water reaction. Might be a bunch of bs tho, I didn't care enough to check
@@fedorg Doesn't make much sense to me. Adsorption with sieves is a matter of equilibrium, reaction with an alkali metal is completely irreversible.
Everyone in my lab does it this way, and we do a *lot* of *really* air and moisture sensitive chemistry (surface organometallic chemistry).
An even better way of drying is to do it over sodium, with a little bit of benzophenone. The benzophenone speeds up the raction, and serves as an indicator by turning purple once all water has been removed. A simple vacuum transfer then gets rid of it.
Oh I didn't mention, I did dry them, when I say 'straight from the bottle' I do mean they were actually dried, but I hadn't like 'un-dusted' them... I didn't make that clear at all.
I usually dry them in my lab microwave. They get very hot very quickly that way, and it seems to work... although I could be dramatically under-doing it. Also, do you know how hygroscopic sieves are? I've always assumed that didn't pull that much water from the air, but the more I think about it I realise that assumption is probably wrong....
Carefully dried dioxane is hygroscopic by itself though isn't it? That's a shame you spent all that time on a thing that probably wouldn't store all that well!
But no, I don't believe I've heard this store, but I am intrigued...
@@fedorg The South African papers that made the claim failed to sparge solvents after sodium treatment. The K-F was picking up dissolved H2. Molten Na is a far more potent drying agent than MS.
@@ExtractionsAndIre You are right. Generally it's best to microwave them until they start to melt (if you have a 1 kW microwave), and not use the melted sieves
.
You really should do this work inside a hood. You are nuts to work with solid sodium and potassium outside a blast shield.
I watch your videos in school and people think im studying 😂
Adds alkali metals a second time before testing his thermometers, that's why I watch E&I.
I am a trusting person. My greatest weakness. The day I trust no-one and nothing, I will be unstoppable
2:40 I can relate
9:09 I love your channel dude. Keep it up 😂😂😂
Protip, microwave the sieves for like 30 seconds then blow nitrogen over them. Repeat this multiple times. If sieves are active, you can tell by holding them in your gloved hand and adding a few drops of water; if they are active you will feel the sieves warm up with the addition of water.
Under 1 hour gang
Under 1 hour gang
Graham ist best for refluxing xD
What's your elevation? That could effect the boiling temperature slightly.
I'm pretty flat honestly... I think the thermocouple is pretty accurate really
Tar are carbons correct?
It's funny you can cut off the bad potassium like it's moldy cheese lol
You should invest into a N2 bottle my dude
I think he has one, he used one in the ammonia video
Post hydrogen explosion: old son you should have enough experience by now to know that Potassium covered in super oxide and added to ethanol is going to produce hydrogen and possibly BANG! Glad to hear you still have both eyes and hands, and what's more no third degree burns. Congratulations on ducking quickly enough to preserve those boyish good looks, A DARWIN AWARD for sure.
did you get more thermocouples?
I am so poor that is simply sand paper and roughen broken glass necks and stick them back together with JB Weld!
Remember to buy more thermocouples
what does it mean for a thermometer to be “cactus”?
Reminder: buy more thermocouples.
Man, this whole synthesis is such a mess... I'm doing it right now and... ohh well
12:45 Sorry for the noob question, but how do you determine how dry it is/isn't based on the temperature?
I'd guess density?
Obligatory year old comment response, but a lot of chemicals that you distill to remove water ot another mixed chemical from form what is known as an azeotrope, which he mentioned in the video. An azeotrope is a mixture of 2 chemicals that boils at a lower temperature than either pure chemicals. Once you boil off all the azeotrope, the mixture no longer contains both chemicals as all of one of them has been carried over in the azeotrope, a lot of times when water is involved the water is the one being completely removed by the azeotrope. As a result, when you see the temperature suddenly jump from where the azeotrope boils at to where the chemical normally boils at, you know that you have gotten rid of all the azeotrope and the water (or whatever else you're using) with it.
@@meme__supreme3373 thanks For the response! I picked chemistry up as a hobby about a year ago, so i def learned about that, prob not long after posting the comment, lol.
But thanks for such a detailed reply.
@@jhyland87 you're welcome
I was thinking about the risk of having a hydrogen explosion right before you said I just had a hydrogen explosion.
you should've warned me in time man
i tried making some LiCl and it went yellow.somehow sodium got in bc now it makes a yellow flame
What happens during a hydrogen explosion?
a reminder to buy more thermocouples... you can never have too many.
So this is basically the driest Dixoane ever? I mean, you dried it after you dried it after you dried it but it was dry all along. Double Dry Dioxane? :P
Omg potassium, my favorite colour fire, purps. Yeah thank you, doc, for keeping the vids coming. And get used to "doc" bc u earned doctorate soon.
What have you become, my sweetest friend?
Everything I make goes yellow in the end
The whole thing with potassium superoxide is that you're not supposed to cut dirty potassium. The mixing of the potassium and its own superoxide can start a fire.
That's why I'm trying to cut the layer off, not so much through it or mash it all up.
I mean I feel like it would take a lot of superoxide for that to happen... I could be wrong and it would be a myth that would take many years to test. But yeah, while the layer is there in this, it's good to just get rid of it so it doesn't keep building up
Am i wrong or you got strike for sulfur tetrachloride video?
Tar is concentrated Yellow.
Worried about superoxides, proceeds to cut it off...
I mean what else can I do, I didn't want to destroy all the potassium!
The thermometer is cactus?
If you mess it up with potassoum, is it pot-messium? Or Shit-as-ium? 😂😂😂
Did you ever get more thermocouples?
i did! took me a long while but I eventually did. someone kept reminding me in the comments haha
5:30 I've heard that you can have an explosion risk by using a metal blade to cut potassium, and that a plastic blade is much safer. Anyway, no more lecturing and on with the questioning: where do you get your Na and K from?
I've never heard that. What I've always heard was that if you cut the potassium and push the superoxide into fresh metal, that will cause it to either catch fire and/or explode. I actually sell potassium and I always use a steel blade to cut it and have never had a spark or flash of fire and the potassium has never even warmed up. Though that could just be my luck. I actually don't know anyone who uses a plastic knife to cut it. That is interesting though. Do you remember where you heard that from? If so, can you post a link? I'm very curious about this.
Don’t trust thermometers within 10 degrees and buy some more thermocouples!
You need merch...
Hey, don't forget to buy more thermocouples
Doesn't freezing molecular sieves destroy their structure?
I... don't know? Maybe. Even if they break up, they still work right, but you talking the internal structure? Unsure
Buy some more thermocouples
BUY MORE THERMOCOUPLES. :P There. I came back months later and did the thing.
Months????? Has it been months???? I still haven't got them
3:33 why the yellow faded after treated with MS?
Yellow is bigger than water molecules
@@GLITCH_-.- Hey Google, how big is yellow?
but unsure why the yellow fades. That's a good pickup, I hadn't actually noticed that
@@ExtractionsAndIre Yellow's thicc. That's why it always hurts to pee.
all you needed was a bubbler...
Lame, I always clean the crust off my alkali metals using my teeth, and you use an old, rusty knife. Damn Aussies... don't know how to get things done...
Rhodanide Remembers me about the video where Cody bit into sodium. But potassium would be really nasty!
@@DrakkarCalethiel that was a wild video wow yeah
Extractions&Ire I would even chicken out on Lithium. But Lithium Chloride's lemony taste is quite good! xD
Molecular sieves is very effective if well chosen AND activated. 2 year old molecular sieves will do nothing.
Yo, do you reckon CaO would work to dry solvents? Using alkali metals feels... Wasteful
It should work.
You would end up with Calcium Hydroxide.
"Bug off"