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1,4-Dioxane (and tar) from Ethylene Glycol

  Рет қаралды 52,773

Extractions&Ire

Extractions&Ire

Күн бұрын

I need Dioxane for an upcoming project (no, its not a sodium synthesis) so I use some of the blue Ethylene glycol lying around to make it. I only swear a few times and don't do that much distillation (both of these things are lies)
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Twitter: / explosions_fire
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Music: From Aphex Twin soundcloud dump: Luke Vibert-Spiral Staircase(AFX remix)

Пікірлер: 154
@name2589
@name2589 4 жыл бұрын
Mate, this video was a Godsend, I was looking everywhere for how to make tar, thanks a bunch.
@pseudomonad
@pseudomonad 5 жыл бұрын
Sweary chemistry videos are the best chemistry videos.
@alllove1754
@alllove1754 5 жыл бұрын
Concur
@AA-gl1dr
@AA-gl1dr 4 жыл бұрын
Who can do chemistry without swearing?
@pgkb216
@pgkb216 3 жыл бұрын
@@AA-gl1dr nobody i work in a lab every half hour someone is screaming fuck 🤣
@rogerdotlee
@rogerdotlee 5 жыл бұрын
"When am I gonna get good?" Anyone that can make Azidoazide Azide on the first go without blowing themselves into the next time zone is good.
@graealex
@graealex 2 жыл бұрын
A Z I D O A Z I D E A Z I D E
@abhinavsaini3512
@abhinavsaini3512 Жыл бұрын
lol
@SodiumInteresting
@SodiumInteresting Жыл бұрын
Thats a joke name
@peterolsen9131
@peterolsen9131 3 ай бұрын
C2N14 !!! tom made it, in a shed, WITH A BOX OF SCRAPS, FROM BUNNINGS!!! [ironman reference...]
@dalitas
@dalitas 5 жыл бұрын
"tar"- the best argument against organic chemistry, thanks for showing us the perils of organic chemistry.
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
yeah agreed. You don't get copper or cobalt tar, it is just bloody carbon up to its usual nonsense!
@dalitas
@dalitas 5 жыл бұрын
@@ExtractionsAndIre i guess you could get carbides but those are easier to deal with still... and your glassware wouldve melted before that
@elephystry
@elephystry 5 жыл бұрын
Maybe @Extractions&Ire can harvest the tar and use it for heatproofing.
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
@@elephystry yeah exactly... I actually meant to make the tar.... yeah.. i wanted it.. sure
@elephystry
@elephystry 5 жыл бұрын
@Extractions&Ire oh no I never meant to say that you wanted to make it, but you might as well make the best of it
@LAppelDuVideo
@LAppelDuVideo 5 жыл бұрын
Tar (and 1,4-dioxane) from Ethylene Glycol ;)
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
oof this hurts
@LAppelDuVideo
@LAppelDuVideo 5 жыл бұрын
@@ExtractionsAndIre Only making a bit of fun, I really enjoy your chemistry videos. Very few chemistry channels also detail the discovery process. :)
@ironmonkey1512
@ironmonkey1512 4 жыл бұрын
PEG
@filipealarza9079
@filipealarza9079 Жыл бұрын
@@LAppelDuVideo The tar distilling over in slow-mo just made me cry of laughter.
@garbleduser
@garbleduser 4 жыл бұрын
We need a glassware cleaning episode.
@SomnolentFudge
@SomnolentFudge 5 жыл бұрын
If it makes you feel better I did this about a month ago on a 1 liter scale and it not only boiled over but blew the stopper out from my distillation head and splattered tar over the ceiling. Also you're luck to be in a warm climate I actually had to heat the water in my condenser for the final distillation to keep the dioxane from freezing, it was about -5c in my lab space.
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
tar on the ceiling! wow that's annoying. And yeah, while I complain about evaporation, having a room temp of 30 degrees C does have some advantages
@calumknott450
@calumknott450 5 жыл бұрын
One of my favourite things is the comparison of Nile red and nurd rage which stay professional with explosions and fire and the “well shit” method
@In_the_shed
@In_the_shed 5 жыл бұрын
Truly my favourite chemist. You make me proud to be an Aussie. I found that when I made dioxane for NR’s sodium synth I just used yellow product and ended up with clear and dry dioxane after two rounds of distillation for two seperate batches of sodium. No extra work and a fair yield of sodium. Keep up the good work, always love the videos.
@sciencoking
@sciencoking 5 жыл бұрын
It always sounds so simple until I see you do it and remember that my luck tends to be the same as yours. Pray for me, I need acetic anhydride and diethyl ether.
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
Thoughts and prayers mate. God help me if I ever need either of them, they seem like synths that I would majorly stuff up
@franglish9265
@franglish9265 5 жыл бұрын
Why do you need AA and ether?
@sciencoking
@sciencoking 5 жыл бұрын
@@franglish9265 oh just ..for chemistry..
@ethansAMAZINGworld
@ethansAMAZINGworld 5 жыл бұрын
you can distill ether from starter fluid if you arent up for the synthesis
@AguaFluorida
@AguaFluorida 5 жыл бұрын
@@sciencoking For simplicity, go 50/50 and make ethyl acetate :D
@NikitkaDreamer
@NikitkaDreamer 5 жыл бұрын
The maxmofoe of chemistry.
@pgkb216
@pgkb216 3 жыл бұрын
Nah hes basically every home chemist ever
@TomsLab
@TomsLab 5 жыл бұрын
2:44 is why I watch Extractions&Ire :)
@roquri
@roquri 5 жыл бұрын
Distill the Becks, maybe you will wind up with a drinkable product!
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
the box is the best bit
@Stoneman06660
@Stoneman06660 4 жыл бұрын
This is a great video. Educational, entertaining, humours, educational and quite beautiful at times. Bravo sir!
@SetTheCurve
@SetTheCurve 5 жыл бұрын
Next time can we see a tar synthesis? Let's explore the wonders if tar.
@todanceonbrokenglass
@todanceonbrokenglass 4 жыл бұрын
Fun Fact: Ethylene Glycol was used as a additive to wine in Europe for a while until it was banned for health risks.
@michaelf7093
@michaelf7093 5 жыл бұрын
So glad to see a rubber hose cushion on your ringstand for your sep funnel. Sets my teeth on edge every time I see a sep funnel on bare iron... I'm just waiting for one to break. One YTer even had a large sep funnel full of Br2 and H2SO4 he just slammed onto an iron ringstand. That could become a problem from which there's no recovery.
@00bean00
@00bean00 2 жыл бұрын
What would happen there?
@Alexander_Sannikov
@Alexander_Sannikov 2 жыл бұрын
this is the only channel where I can satisfy all my tar and aussie wordsmithing needs.
@wilbertbirdner1303
@wilbertbirdner1303 5 жыл бұрын
at 12 minutes i was going to say, at least it's not yellow, then you said it yourself
@doyale2
@doyale2 5 жыл бұрын
great video m9!
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
thanks mten
@Alexander_Sannikov
@Alexander_Sannikov 2 жыл бұрын
gotta love the slow motion replay of the time lapse, quality content right there
@kieranodea771
@kieranodea771 5 жыл бұрын
I would try a sand bath instead of a water one. I've used regular play sand to heat large round bottom flasks. Works great just takes more time to heat up.
@Kirillissimus
@Kirillissimus 5 жыл бұрын
There is a round type of sand sold in pet shops for hamsters or parrots or something like that. The little ones like to bathe in the stuff so people buy it. It is like river sand but has finer grain. This kind of sand is especially good because it is softer to compress and it does not scratch your glassware. It is even called ”bathing sand“ to show that it is supposed to be good for sand baths.
@Christian-os3kk
@Christian-os3kk 4 жыл бұрын
Love that you put aphex twin in the vid
@cphVlwYa
@cphVlwYa 5 жыл бұрын
Ah Dioxane, the chemical which caused me to write the "no orgo in the house" rule ... At least until I finish building my fume hood.
@j_sum1
@j_sum1 5 жыл бұрын
So. Very. Familiar. (Except for the rain. We don't get that round here.) It is like you made a movie of my lab notes. The yield is crap. But the colours from the decomposing dye at the beginning are really pretty. Good luck cleaning the flasks.
@ntal5859
@ntal5859 Жыл бұрын
I am sure his neighbour think he cooks ICE on the weekends with all the smells.
@Matoro342
@Matoro342 Жыл бұрын
You are my favorite tar synthesis channel.
@java9090
@java9090 5 жыл бұрын
You would've gotten a high yield if you had used a VB box instead of a Becks box.
@GodlikeIridium
@GodlikeIridium 4 жыл бұрын
I suggest you get one of those pieces of glassware made to stop boiling over. They are very simple and let vapor pass, while liquids boiling over get stopped and flow back down.
@Tom-lm2tc
@Tom-lm2tc 2 жыл бұрын
Honestly the quitting which you're ahead bit fucking killed me, considering my own lab woes 😔
@Penguin24766
@Penguin24766 Жыл бұрын
The "sorry dad" xD I feel ya
@vaderdudenator1
@vaderdudenator1 2 жыл бұрын
That massive string of f bombs spoke to me on a spiritual level
@Enjoymentboy
@Enjoymentboy 5 жыл бұрын
Ah. the good old "box of beer on its side" trick. A staple of the true chemist. And I don't know why you were so upset when the tar boiled over and contaminated your product. It's not like it was yellow.
@SodiumInteresting
@SodiumInteresting Жыл бұрын
I want that green condenser 💚
@ScienceWithJames
@ScienceWithJames 5 жыл бұрын
No need for a lab jack when you have a box, a brick, and a really small table.
@thepoliticalschizophrenics3555
@thepoliticalschizophrenics3555 2 жыл бұрын
it shat itself
@tehPwnzor7306
@tehPwnzor7306 4 жыл бұрын
that AFX track in the timelapses is very well-chosen
@DukeOfEarle88
@DukeOfEarle88 4 жыл бұрын
@9:14; beautiful yellow color. 🙂👍
@franglish9265
@franglish9265 5 жыл бұрын
I wonder if the tar is caused by acrolein polymerization. Also, yellow isn't bad if your product is a nitrated arene. I hear essence of piranha vitreol should clean up the tar.
@Kycilak
@Kycilak 5 жыл бұрын
Is there anything in organic chemistry that would resist piranha?
@cezarcatalin1406
@cezarcatalin1406 4 жыл бұрын
Lukáš J. Superfluorinated polymers. That shit can only be decomposed by strong bases.
@theemissary1313
@theemissary1313 3 жыл бұрын
I don't like to watch you fail, but it's funny how much i relate to a person struggling to articulate just how much they fucked up. "It's nearly midnight, gotta be up early and my whole set up is covered in... fucking... cancerous......... shit..... >:( " XD
@Rhodanide
@Rhodanide 5 жыл бұрын
Having fun with the slow motion I see
@MsMotron
@MsMotron 5 жыл бұрын
love your videos!
@fbiopenup6698
@fbiopenup6698 5 жыл бұрын
Epic vid mate
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
thanks mate!!
@JustAnotherAlchemist
@JustAnotherAlchemist 2 жыл бұрын
Dot 3 brake fluid contains large amounts of diethylene glycol (DEG), which is better for this kind of thing that just ethylene glycol (MEG).
@Slowly_Going_Mad
@Slowly_Going_Mad 4 жыл бұрын
I like what he did with this video.
@goatswag2744
@goatswag2744 5 жыл бұрын
aphex twin very strong
@GodlikeIridium
@GodlikeIridium 4 жыл бұрын
I like your lab boy replacement xD
@burntorangeak
@burntorangeak 4 жыл бұрын
And that kids; Is how vape juice is made.
@GodlikeIridium
@GodlikeIridium 4 жыл бұрын
Lol xD
@M.J.C.W.
@M.J.C.W. 4 жыл бұрын
I would like to see how you clean glassware
@ettanasf
@ettanasf 4 жыл бұрын
It’s beautifully clear...AND COLORLESS!
@avlsage
@avlsage 4 жыл бұрын
Lmao "looks like the expensive stuff, which I'm using. but sorry dad...doesn't matter..."
@crashmatrix
@crashmatrix 3 жыл бұрын
Aaaand the black sludge cometh.
@rogerprodactorstevez6740
@rogerprodactorstevez6740 5 жыл бұрын
aphex twiiiiiiiiiiiiiin
@jonholmes3013
@jonholmes3013 5 жыл бұрын
Fucking great man
@arved-6939
@arved-6939 5 жыл бұрын
Glad to see you re at least drinking German beer
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
hey, just because i've got the box doesn't mean i'm drinking it
@AguaFluorida
@AguaFluorida 5 жыл бұрын
@@ExtractionsAndIre Störtebeker is much nicer, but I doubt you'll get that in Oz. [The gritty (or should that be, tarry?) realism of your videos makes them all the more compelling. It always makes me happy when you post a new one. Keep it up with the style!]
@markiusgalfordii9248
@markiusgalfordii9248 3 жыл бұрын
It's your show still going I love it keep up the good work you Aussie son of a b h
@johnblacksuperchemist2556
@johnblacksuperchemist2556 3 жыл бұрын
extractionsandfire...........I am trying this experiment to see how much acetaldehyde i can make. I know not much but i am curious how much. Going to add a lot more sulfuric acid to raise the boiling point of the pot. Trying to get the pot to boil HOTTER at 170 to 180C to get an elimination making acetaldehyde instead of an SN between 2 ethylene glycols making dioxane. I figure that is what you would do if you want to make ethene instead of diethyl ether. So maybe it will raise the yield of the acetaldehyde. Guess i will find out tomorrow
@ulyssecaniparoli5331
@ulyssecaniparoli5331 4 жыл бұрын
to heat round bottom flask just sand is very efficient
@YanestraAgain
@YanestraAgain 3 жыл бұрын
Cool. That's how Chemistry is!
@AllChemystery
@AllChemystery 5 жыл бұрын
It’s unnecessary but why didn’t you distill the Coolant fist? It takes a while to do but I think it’s worth the extra effort plus you can dry it for easier dehydration. I feel your pain with the screwup! Dioxane is seriously unpleasant to deal with. It gets sickly very fast. The Acetaldehye isn’t particularly pure either. I tried to keep mine but it polymerised quickly into black goo...
@jhyland87
@jhyland87 5 жыл бұрын
People don't like watching you fail... Or at least I sure don't. It's watching you go through the learning process (in its entirety) that we like to watch, and maybe learning from your mistake so we don't repeat them. SoOoOooo.. Thanks for takin us along for the ride, mate! :-) P.S. plus, ive always thought you learn more from failures and being wrong than you do when everything goes to plan...
@terawattyear
@terawattyear 5 жыл бұрын
We don’t watch your vids to see you hurt yourself. For that we watch Electroboom. You gonna make sodium a la Nurdrage with that Dioxane?
@tatemcaluney7269
@tatemcaluney7269 5 жыл бұрын
1:06... Hmm green condenser... tribute to saint patrick’s Day. Clever girl.
@pyromen321
@pyromen321 5 жыл бұрын
Did you get a new camera? Those were some cool close-up slowmo shots!
@matty8944
@matty8944 5 жыл бұрын
Just wondering; Why do you put (what I assume is) detergent into the cooling water?
@AA-gl1dr
@AA-gl1dr 4 жыл бұрын
Matty Probably to drop the freeze point?¿
@edgeeffect
@edgeeffect 4 жыл бұрын
Excellent camerawork and swearing in this one.... I've got to look up what dioxane is used for.... I hear the name and all that comes to mind is "Bopal".
@xxxftcxxx
@xxxftcxxx 3 жыл бұрын
I love that you are not a snowflake chemist, you don't give fuck about cursing and I LOVE that about you because you really make yourself relatable and a normal person who acts like you or I.
@Frostlander
@Frostlander 5 жыл бұрын
I wonder if they stick crap in the ethylene glycol to mess with chem like this.
@damienrose3176
@damienrose3176 5 жыл бұрын
shouldn't a vacuum adapter have stopped the tar build up?
@hunterlankford2402
@hunterlankford2402 4 жыл бұрын
How does one clean this tar
@piranha031091
@piranha031091 5 жыл бұрын
0:18 : So... are you going to make sodium by the NurdRage process? ^^
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
nope, something completely different actually! I wont spoil the surprise though
@piranha031091
@piranha031091 5 жыл бұрын
​@@ExtractionsAndIre OK. I'll leave dimethylmagnesium as my final guess, we'll see how far off I was! ^^
@Felixkeeg
@Felixkeeg 5 жыл бұрын
@@piranha031091 Was thinking dimethylmagnesium too, would be fucking cool, but as far as I know, without Schlenk technique, it's quite impossible
@piranha031091
@piranha031091 5 жыл бұрын
@@Felixkeeg Eh, you can easily buy pure argon as shield gas for MIG/TIG welding. And there are ghetto ways to get around not having a schlenk line by using septums and needles to keep everything flushed.
@user-eb3nm8cr7i
@user-eb3nm8cr7i 5 жыл бұрын
Awesome! How did you clean the tar in the flask and everything, it looks like pain to scrub in there and also like a huge waste of organic solvent if that is used...
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
'how did you clean' implies that I've done it. I have not. all the dirty glassware is still in a bucket. I decided to edit the video first instead haha
@okay8632
@okay8632 3 жыл бұрын
H2SO4/HCL + H2O2 is great for eating that stuff off the glassware
@okay8632
@okay8632 3 жыл бұрын
Also warm not hot naoh solution
@hihowareyou7810
@hihowareyou7810 3 жыл бұрын
"you can see,there's more in the pot...then there is what we got.!*BARS!*....*BARS!*"
@taylorwhitt3974
@taylorwhitt3974 4 жыл бұрын
shit ton? Is that a metric or imperial measurement?
@harrisonfnord5871
@harrisonfnord5871 4 жыл бұрын
German beer!
@CED99
@CED99 4 жыл бұрын
Using Dioxane in place of THF?
@simonsepic
@simonsepic 5 жыл бұрын
Love your channel but just wanted to say there is at least one scenario where yellow is good haha. THC oil haha
@alfredogonzalez2857
@alfredogonzalez2857 4 жыл бұрын
¿Diethylene glicol would work too? I only find ethylene glicol with that.
@Dorastern81
@Dorastern81 5 жыл бұрын
Out of all good german beers it is BECKS? :D
@peterirvin7121
@peterirvin7121 5 жыл бұрын
Dollar for dollar, it's way cheaper to get drunk on cheap beer than expensive beer lol
@swabianscience
@swabianscience 5 жыл бұрын
Wouldn't this reaction also cause minor amounts of crown ethers to form? You might want to check the residue
@jamesg1367
@jamesg1367 5 жыл бұрын
By way of assaulting you with my 20-20 hindsight... might it have been helpful to distill the glycol as a first step? Maybe get free of whatever dye and shit was in there and so reduce the byproduct count?
@cognitivedissonancer
@cognitivedissonancer 5 жыл бұрын
Ethylene glycol's bp is pretty much at 200C. It'd be hard to control the temperature (maybe an oil bath, but it will get smoky). Reduced pressure distillation will get you there, but at that point, it's easier to clean up the dioxane. IIRC, Vogel has a procedure on that.
@In_the_shed
@In_the_shed 5 жыл бұрын
I distilled my ethylene glycol before the dioxane synth, it only took HOURS of my life but now iv got plenty of clean ethylene glycol
@FlapJacks7
@FlapJacks7 2 жыл бұрын
Like how do u dispose all these failed attempts and byproducts??
@PepekBezlepek
@PepekBezlepek 4 жыл бұрын
people who don't swirl the sep funnel like that aren't real chemists tbh
@okay8632
@okay8632 3 жыл бұрын
how much acetaldehyde do you predict you separated out of it?
@FlapJacks7
@FlapJacks7 2 жыл бұрын
Fire?
@jameswallace9906
@jameswallace9906 4 жыл бұрын
Why don’t you use ice bath
@006bloody
@006bloody 4 жыл бұрын
I'm like 666.....weird
@lucaswang3908
@lucaswang3908 5 жыл бұрын
Is there a reason for dyeing the condenser water green?
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
No not really, just thought it might look cool :P
@matty8944
@matty8944 5 жыл бұрын
Also is conc. sulphuric acid meant to be yellow?
@ExtractionsAndIre
@ExtractionsAndIre 5 жыл бұрын
It's not yellow, at least this stuff isnt! It only went that weird yellow after being added to the ethylene glycol, it was doing funny things to the dye and making it go yellow and green and stuff
@matty8944
@matty8944 5 жыл бұрын
@@ExtractionsAndIre Oh sorry I didn't mean to confuse you. You reminded be about my sulphuric acid when you called yellow a shit chemistry colour. Cause my conc. sulphuric acid has a yellow tinge and I'm not sure whether it's suppose to be that way. Would you mind giving your input?
@luisillo3511
@luisillo3511 5 жыл бұрын
Can that tar be considered a polymer?
@SocialDownclimber
@SocialDownclimber 4 жыл бұрын
I would consider it a macromolecule because the molecular weight is probably above a few thousand daltons. I wouldn't consider it a polymer though because it consists of a disordered, crosslinked set of random dehydrated side-products instead of an ordered combination of a small number of monomer units. When you look at the molecular structure of a polymer you should easily be able to identify the monomers used and which bonds were formed to link them. When you look at tar you just get a headache.
@Terrik240
@Terrik240 4 жыл бұрын
Why is it always more fuckin tar
@alexredacted2123
@alexredacted2123 4 жыл бұрын
WHY ARE YOU DISTILLING RIGHT TO LEFT REEEEEEEEEEEEEEEEEEEEEEEE
@burntorangeak
@burntorangeak 4 жыл бұрын
Do not put this in your Vape, It tastes like an open and burnt a**hole.
@TheKingOfChemist
@TheKingOfChemist 4 жыл бұрын
Brother boring.
@alllove1754
@alllove1754 5 жыл бұрын
I like the fact you dont play smart, but carry on and get the job done, calling commercial mixtures colloquial terms so we peons with ADD keep watching and learn. In highschool if your channel had existed id have kept up with it. Thank you.
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