Making Ether

In this video I demonstrate how to make diethyl ether, which was an anesthetic drug that revolutionized medicine, and is today mostly used as a solvent.
I did this process last year, but its such an important chemical I felt it deserved a redo.
Always make sure to take proper precautions before attempting anything seen in this video. The chemicals used are extremely corrosive, and ether itself is extremely flammable.
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#chemistry #science #hydrogen #gas #elements #fire #chemical #industury #color #green #light

[@hattree]

I've often freaked people out by saying, "Whenever I smell ether, I think of my Grandpa." Why do I say this? He was missing an eye, and would tape a gauze patch over the missing eye. At the time, medical tape was extremely sticky and would leave behind residue. He would by cans of Humco Ether and there was always one sitting next to the sink. He would use it to remove the sticky tape residue from his skin. Most people wrongly assume he was an ether huffer, but he was just a drunk.

[@integral_chemistry]

Well I'll give it to him, ether does remove adhesive residue like nothing else.. I wish I could get ether so easily. Also that last line got a chuckle out of me

[@samuelfellows6923]

I assume he didn’t want the stereotypical appearance of a pirate with the black band and eye-patch, the patch was skin coloured to disguise it,

[@hattree]

@@samuelfellows6923 He didn't like the black elastic band patches. He said they were itchy.

[@jwm6314]

Got me. Belly laughed.

[@Psychx_]

I had an accident with Diethyl Ether once, which lead to a liberation of a big amount of vapours and me inhaling them. The effects made me see the infinity of space, time and the multiverse. It was equally impressive as it was disturbing - turns out the stuff can mimic a psychotic episode (this is documented btw). I noticed deja-vu/thought loops, followed by acoustic hallucinations which resembled a mixture of white noise and intense echoing, and finally also visual hallucinations with repetive motives. During that time I lived through my life and died dozens of times and I've seen the cosmos doing the same. The whole experience was accompanied by a lingering anxiety, and at times panic, that there is no free will and things are destined to repeat over and over again in exactly the same way without one being able to change anything. Thankfully, the effects ended rather quickly when all the ether had evaporated and was carried out of the room through ventillation. I was left with a slight feeling of confusion, nausea and a some restlessness - kinda like drinking too much coffee, but without the high heart rate. I didn't sleep well that night. The next day, my breath still had a distinct ether taste and smell, which could be noticed by others - kinda like I fell into a paint can. It took nearly 24 hours since the accidental exposure for the stuff to completely leave my body. This was due to diethyl ether having a boiling point around body temperature and being highly lipophilic - it'll accumulate in fatty tissues and most of it is removed through the lungs. A small amount is also metabolized to ethanol and ultimately acetic acid in the liver. This is also what makes many other ethers toxic - "Methyl-Ethyl Ether" will get metabolized to Methanol ("Dimethyl Ether" is fine, since it's too small for enzymatic crackdown), "Diisopropyl Ether" will ultimately form Isopropanol, then Acetone in metabolism and so on (and linger in the body for even longer!). All in all, I cannot recommend such an experience and I advise all of you to take your workplace safety seriously, esp. in DIY settings!

[@violaanderson175]

Sounds like an experienced psychonaut trip report...

[@integral_chemistry]

First off, that sounds like an absolutely horrific experience, and I'm sorry you had to go through it.. although as a chemist and a history-lover it is fascinating to hear about the effects firsthand. I think at this point I've made ether in this way 7 times now, but the very first time I underestimated how extremely volatile the stuff is and I also caught a dense (albeit breif) inhalation of the fumes. Before I had a more proper lab with strong ventilation and a very high end respirator, my strategy used to be to just stop breathing, cut power to heating, and leave the room the instant I caught a whiff of anything I didn't intend to smell. That said, I certainly did not end up getting exposed to nearly the amount you are describing, but I did indeed inhale enough to get a few very distinct side-effects. In my little experience this resulted immediately in what you described as acoustic hallucinations, all the various buzzing and humming sounds that are constant in my workspace became much more intense and unpleasant with a depth that was very surreal/dreamlike. Light also had a different quality to it for at least the next half-hour, as if you turned down the exposure and turned up the saturation of everything. There was a lingering intense anxiety throughout the experience, and I also couldn't shake the ether smell for several hours. Overall it was unpleasant and an experience I've effectively taken steps to not repeat. As you said, some degree of the intoxication is caused directly by the breakdown to ethanol. Weirdly enough this action inhibits alcohol dehydrogenase which slows the metabolism of ethanol. However the primary route of ether intoxication is that it is a potent NMDA antagonist (along with many other anesthetics). This quality is shared by N2O, ketamine and phencyclidine, which would certainly explain your experience. In any case yes I 100% agree that everyone should take safety seriously, especially with gaseous compounds that could render you unconscious as the last thing you would ever want to be in a laboratory is unconscious.. This is why to this day the scariest chemical to me is carbon monoxide. Completely odorless and insidious.

[@petevenuti7355]

The kind of thing you wake up from and scream "I can see God"

[@jeffreyyoung4104]

Been there, done that, a few times, back in the 70s... I don't want to repeat it ever again, due to the waning I got the last time through the trip.

[@julioperez-delgadojr2976]

Thanks for telling us about that, it is very weird that you would happen to get all that insight from an accident like that.. A lot of people who seek knowledge of that sort will easily spend a lifetime and still miss out on a lot of the puzzle pieces.. Have you studied particle physics and waves, or are you an engineer by any chance? What I mean is, were you ever thinking about those topics Or did all this stuff just came out of nowhere during that accident? I'm no genius, and I still have plenty to learn about.. but I've spent a lot of my life learning about how things work and your explanation there was pretty much my conclusion to the whole universe so I find it very bizarre that you just got all that stuff in your head from nowhere.

[@quint3ssent1a]

I remember reading about how in England during so called "gin craze" people distilled gin with addition of sulphuric acid, which made end product a mix of ether/ethanol. Damn, that's some bone-chilling stuff.

[@integral_chemistry]

Jesus 😅 yeah I have heard they still DRINK this stuff in parts of Eastern Europe which is nuts to me

[@isaacmcginn7923]

The music you use is perfect for such a chill chemistry video 1:30

[@dustinkraich6981]

"There is nothing more helpless and depraved than a man in the depths of an ether binge. And I knew we would get into the rotten stuff pretty soon, probably at the next gas station."

[@integral_chemistry]

Love Hunter S Thompson! Honestly considered including that quote in the video but I wasn't sure it matched my typical tone lol

[@p1ngu236]

cozy diethyl either 😍🥰

[@flyingshards595]

Nice! The details and description are appreciated!

[@integral_chemistry]

No problem at all! I worried I might have gone too off-topic but I'm glad you don't think so

[@johnslugger]

*In the 1800's Ether Drinking was very popular in Ireland.*

[@garrymcgaw4745]

Very interesting mate thank you.

[@integral_chemistry]

No problem!

[@experimental_chemistry]

Yes, once again paradoxical: in this country, diethyl ether is not available on every corner, but you can easily order it in small quantities (100 ml) from German chemical retailers or from Dutch online pharmacies, sometimes by submitting an end-use declaration. For larger quantities, shipping is quite expensive as it has to be sent as dangerous goods via a freight forwarder. Well, making it yourself is largely forbidden here: as already mentioned several times, private possession of concentrated sulfuric acid is a moderately serious crime in this country, punishable with up to 3 years in prison. Yes, the crazy EU... Alternatively, anhydrous zinc chloride can also be used, but unfortunately I was unable to achieve any significant yield with it. I use methyl tert-butyl ether instead of diethyl ether anyway because it is less flammable, hardly forms peroxides and can also be stored unrefrigerated. Diethyl ether, on the other hand, must be stored in explosion-protected refrigerators. I don't even have a normal refrigerator in my hobby laboratory... Even if the stored diethyl ether is stabilized, it should be checked for peroxides with acidified potassium iodide starch solution before each distillation. Otherwise the risk is simply too high. At the same time, production with concentrated sulfuric acid always generates traces of diethyl sulfate, an insidious poison and strong carcinogen. That's why I've been avoiding using this method for decades, even when concentrated sulfuric acid was still permitted.

[@integral_chemistry]

I'll never get over the absurdity of EU chemical laws.. even here it is a bit obnoxious, for months I've been sitting on a video showing three methods of methylamine synthesis that I haven't released or even begun to edit as I'm still working on getting a solid response through official channels on whether or not that would be allowed to demonstrate. In any case I have looked into tert-butyl ether for the reasons you stated, but weirdly enough I have not been able to find any way to buy butanol, pentanol, cyclohexanol, or benzyl alcohol.. Guess I'll keep looking. I was aware of the potential formation of diethyl sulfate, and it is my best explanation of the darkening of the reaction mixture as the reaction proceeds. It is very scary stuff that I try and avoid at all costs (as well as pretty much all methylating and ethylating agents), but I feel that it has such a high boiling point it would likely remain mostly in the reaction mixture no? Reguardless definitely something to keep in mind.

[@experimental_chemistry]

@@integral_chemistry Basically, the alcohols you mentioned can be bought here completely legally and without any suspicion. Unfortunately, there are not many chemical dealers left in Germany who still sell and ship to private individuals. The bureaucratic effort and liability risks are usually simply too high. The nearest chemical dealer with counter sales is over 500 km away from me. In my early days, a good 35 years ago, you could get almost everything in the nearest larger pharmacy in the next town. Even methylamine is not subject to any restrictions. Only what falls directly under the Narcotics Act or is a direct precursor substance is not legally available. Most auxiliary substances have such a high quantity limit that the normal hobby chemist can never exceed this limit in his life. Of course, you should always avoid certain combinations when ordering to avoid false suspicion. The authorities here are really only paranoid about xplosive precursors. Just a few grams of potassium nitrate and light metal powder, which in themselves can also be legally possessed, are - especially if ordered in combination - a direct invitation to a house search. For this we can thank those who let masses of people with criminal potential into the country... Then you have to differentiate: YT has no problem at all with many of the things that get you in jail in this country. Other things that are completely legal here will sooner or later lead to a strike or at least demonetization on YT. Unfortunately, the hurdles for this are not high at all. And unfortunately, those who programmed the testing algorithm or do manual sampling don't have a clue about chemistry. Accordingly, the result is often quite arbitrary. I would also guess that methylamine has a high potential for demonetization. Shortly before my last videos I thought about showing the synthesis of anthranilic acid, but decided against it for the reasons mentioned. I don't want those who just want to see how dr*gs are cooked or xplosives made as my viewers. I expressly distance myself from this. I even don't like the fact that the production of potassium nitrate is my most successful video. Pyrokids are just not my target group...

[@experimental_chemistry]

@@integral_chemistry Thankfully, diethyl sulfate is actually not very volatile, but even in small quantities (e.g. via aerosols, which are always formed during distillation) it is still so dangerous that the risk should not be underestimated. Diethyl sulfate should therefore only be used in closed systems. However, contact can no longer be completely ruled out when disassembling and cleaning the devices.

[@user255]

@@integral_chemistry Just wash the ether with Na2CO3 water solution, then dry and distill.

[@MoxxoM]

A few years ago I could easily get a liter of Diethylether from my local pharmacies in Germany. Went there a few months ago and none of them would even consider it nor did they have any. For the sulphuric acid: I had to get rid of more than one liter back then.. Of cause without monetary compensation for my loss. I think the EU laws are insane and every year it gets harder to perform this hobby. It's really a shame. And it's not like it's impossible to make all those things they banned anyway if you are motivated enough and don't care about the laws, because you want to do really bad things. So what's the point here anyway?

[@jozefnovak7750]

Super! Thank you very much!

[@MJTVideos]

Always be careful distilling ether since explosive H2O2 is always a concern. If you want to store ether I strongly recommend adding a bit of BHT as soon as possible

[@integral_chemistry]

100% agree. I threw a little in at the end, so far never had any problems. I am concerned about making other similar compounds that much more readily form unstable peroxides. Specifically Dioxane and isopropyl ether.. You wouldn't happen to know if BHT works equally well for those would you?

[@iknownothing-m8c]

Is hydrogen peroxide explosive? Since when?

[@integral_chemistry]

@@iknownothing-m8c Its not hydrogen peroxide (although 100% hydrogen peroxide might as well be explosive). I think he made a typo but specifically ether condenses to form diethyl ether hydroperoxide which is an extremely sensitive contact explosive. Typically not much forms but if even a little does it'll ignite the ether... which would be a problem.. You know how meth labs explode? Thats why

[@stefangadshijew1682]

@@integral_chemistry Are you sure? I thought it was PH3, which ignites on contact with air. I don't really see where you need to use Ether in the synthesis of Meth, but using P and generating PH3 as a side product seems to be quite common.

[@knivesnico8775]

nice video! nice! nice dude!

[@MoxxoM]

Great video, keep it up.

[@ZoonCrypticon]

A very interesting and informative video, thank you ! Could you please note, why you chose diethyl ether as a solvent to synthesize, and not for example the cheaper dimethyl ether, or the molecule methyl ethyl ether, which later could be fluorinated to the well known and used inhalational anesthetic desflurane. Thank you!

[@integral_chemistry]

I guess the simplest reason is just that both methyl ether and methyl Ethyl ether are both gaseous at room temp, which is very limiting with my setup. Also, methyl ether by this synthesis will co-produce the sulfuric acid ester which is crazy toxic

[@waynoswaynos]

Man, great production value and concise lesson, thank you. But I was wondering, at the beginning you start with ethanol in the flask and add acid slowly and say you used an ice bath to keep the temperature under 135˚. Why not just begin with the acid in the flask, and slowly add the ethanol instead? I imagine the temperature could be controlled this way without any need for ice. Is there are reason not to do this?

[@integral_chemistry]

Thank you so much! And good question actually. So the thing with that is that the acid is the reactive chemical here, and the ethanol is simply acted on by the acid (I'm oversimplifying obviously). The point is that adding a small amount of acid to a lot of ethanol results in the large amount of ethanol heating up a little bit, but adding a small amount of ethanol to a lot of acid will cause the ethanol to instantly vaporize, potentially explosively. I have a video called manganese heptoxide 2 or something like that where I show an extreme example of what it looks like to add a small amount of organic solvent to a powerful acid. Rule of thumb: always add acid, never add anything to acid.

[@waynoswaynos]

@@integral_chemistry Awesome. Thank you. Makes good sense.

[@dalitas]

Awesome video But for the mechanism the electron pair of the unprotonated alcohol would attack the carbon and then kick off h2o

[@integral_chemistry]

True^^ I think that's drawn correctly in the first little mechanism I found online, but the one I tried to make myself became a bit of a mess.. I think I'm just going to hand draw them in the future lol

[@exhaustus7437]

The worst part about fractional distillation is that you are running RX's like, 20 times. just to get a liter. Profit for Profit most of the time its a drag. I have an organic distillate and gas wash capture tincture that brings in like $5,000 a liter. I wish I had more time.

[@integral_chemistry]

I agree 1000%. I have like 10 projects I want to do and the only thing holding me up is that a fractional distillation is like an entire day commitment and I don't have that kind of time.

[@NiC.kChenNC]

This is awesome

[@integral_chemistry]

Thank you 😁

[@FullModernAlchemist]

Wait you can’t get starter fluid? That’s how I get a lot of my ether. It’s stable in those cans. I just distill off the ether right before using it so it doesn’t form peroxides in storage. (Don’t have any BHT on hand)

[@integral_chemistry]

The only brand I've been able to find is a 35% ether blend which seems more hassle than its worth.. I live in massachusetts and based on your videos I've seen you're on the east coast as well (Just a guess). Feel like they probably sell similar brands where I am, do you happen to know any brands that are a bit closer to 100% lol?

[@mumgusbug9121]

How do I get a hold of ether

[@AaronSchwarz42]

Starting Fluid automotive store

[@gkiferonhs]

If ether boils around 95°F and ethanol is around 170°F how do you keep things around until the 275°F needed for the reaction?

[@integral_chemistry]

Well a good deal of ethanol does end up boiling away which is why the final yield wasn't great (and never is). But I think the reason it doesn't boil away sooner is probably just a function of the fact that it is in solution with sulfuric acid, which massively increases its boiling point especially when the proportion of sulfuric acid is so huge like this. Same thing happens when you need to remove water from a sulfuric acid-water mixture. Water boils at 100C but you need to heat it to nearly 300C to remove the majority of water from sulfuric acid.

[@stefangadshijew1682]

@@integral_chemistry In a very old textbook, I found the mechanism explained to actually proceed via the formation of the monoethylated sulfate and not over an oxonium ion, which would explain the stability and nonvolatility of the first step. The second step, they kind of glossed over, but suggested the formation of SO2 as a byproduct. They suggest that to explain why crude technical Diethylether produced via this process has a characteristic smell of burnt sulfur. It was called "Sulfuric ether" or "Schwefeläther" in the past because of this. But to be honest, it could just be that when using technical grade sulfuric acid and distilling at those temperatures, you also distill some volatile dissolved SO2.

[@MrTk6969]

Would purging the storage container with N2 or Ar mitigate the risk of the peroxide formation

[@integral_chemistry]

Maybe.. Although I don't think so as I believe the mechanism of peroxide formation happens between the ether molecules themselves.

[@stefangadshijew1682]

It depends. It could make the BHT stabilization less effective. If you don't stabilize with BHT, Argon or N2 would definitely be a good idea, but probably not sufficient. Some O2 will still find its way in. The unstabilized THF I use at work definitely came blanketed with Argon, but is expected to degrade quite fast with each opening of the bottle. I know for a fact from experience that stabilization of Acrylic- and Methacrylic derivatives with BHT only works when you _do not_ blanket them with Argon. If I vacuum distill products with those motives, I always bubble a slow stream of dry air through them, otherwise I get a polymeric mess. I am not 100 % certain that this also applies to Ethers and Peroxides. The difference is that Acrylic and Methacrylic derivatives react in a chain reaction that only need (in theory) one molecule of O2 to start, while Hydroperoxide formation of Ethers requires stochiometric amounts of O2. But my guess is that BHT is still much more effective then Ar or N2.

[@littlehills739]

so Ether would be good non toxic way to remove Capsaicin from chilies ?

[@integral_chemistry]

I mean ether is still somewhat toxic but yeah it's an excellent solvent! Been meaning to do a capsaicin extraction for a while, might give ether a try

[@RohanLoomis]

How would the reaction be affected with trace amounts of methanol? Would it be fine to distill alcohol fuel for the ethanol, and then perform the reaction? Its a perfect time because my area is at like 10C right now.

[@integral_chemistry]

Nah trace methanol wouldn't make a huge difference. Worst case scenario is you make small amounts of methyl-ethyl ether which has an extremely low boiling point and doesn't really make it into the final product

[@Correct_Opinion]

quick meme 3:06 the nucleophilic attacks the carbon adjacent to the protonated hydroxyl

[@integral_chemistry]

Yeah... Not happy with how my mechanisms turned out. I was trying to use this new software but I've yet to find a software to design these mechanisms that is at all user-friendly. I think I'll just go back to drawing them by hand and just try to make them look somewhat presentable

[@nabilNafa2001]

Wow 😂wow😅 wow 😁Hypnosis and chemicals are things that baffle scientists in terms of manufacture and experience.

[@frederiquecouture3924]

Merci beaucoup pour votre vidéo.

[@jamessshep6106]

Can the ether be stored under argon to prevent the peroxide formation?

[@davidfritz7688]

My grandpa had a bull he needed to knock out to put a ring in it's nose. He was stubborn and proud and didn't want to wait for a vet to come knock it out. He said to himself "they knock them out with ether. Starter fluid is full of ether" So he sprayed that bulls nose full of it and put the ring in while it was loopy Amazing he didn't kill that poor animal

[@integral_chemistry]

LMAO that is hilarious but also terrible 😅

[@kpunkt98]

I usually dont wanna be that guy but it really grinds my gears due to my studentsa all doing the same: Try to really pay attention to your electron arrows, especially the start- and endpoints. where you show protonated ethanol being attacked nucleophilicly by the 2nd ethanol, the arrwo should point to the carbon, not the protonated alcohol oxygen. otherwise gerat video :D

[@kpunkt98]

also: I'm not really familiar with end consumer glassware prices - how much more expensive is a droppig funnel with teflon plug instead of a glass one?

[@kpunkt98]

if I'm not completely mistaken, BHT's job is to interrupt the radical chain for peroxide formation, not to destroy existing peroxides. The chain starts with singlet oxygen stealing a hydrogen atom, then the chain starts with the radical reacting with the much more abundant triplet oxygen, forming peroxides and stealing another hydrogen atom.

[@integral_chemistry]

Lol thank you, but yeah I agree with you it is an important distinction. I keep trying to use this free software I found to model these reactions, but I HATE using it to the point making any arrows at all is a headache. I might just start hand-drawing my mechanisms so they're more accurate and try to make them semi-presentable for the video 😅

[@Woodyperckerhead-ni3ti]

Second grade fell outta tree broke my left arm Walked to mom an she about died because it looked like a boomerang And the time I was under The ether to set my arm I was dreaming wildly My dad was finishing up his accident in the deep mine with missing school had time to gosquirrel hunting with my dad 1965

[@rezaalijanianzadeh4202]

Diethyl ether is pure?

[@integral_chemistry]

It can be if you purify it. If you're asking whether its a pure substance, then yes it is, its not a mixture of different chemicals.

[@TestECull]

I need to get the glassware for this and permanently set it up. I do a lot of RC stuff and one form of model engine burns a fuel mixture comprised of equal parts ether, castor oil, and kerosene. Model Diesels. Ether is a BITCH to get a hold of for making this fuel and readily mixed brews are even harder to find. If anyone is curious to see one of these engines run, just look up PAW Diesel on KZbin and you'll see. They offer various sizes, with and without throttles, are of exquisite quality, and still get produced commercially.

[@integral_chemistry]

Its weirdly difficult to get ahold of. No idea why but I'm assuming its just hazards in shipping maybe? I just checked out the PAW 55 and they do look super cool. Might have to get me one and add it to my ever growing list of hobbies lol

[@hellothere3163]

Good huff

[@integral_chemistry]

lol

[@Woodyperckerhead-ni3ti]

Mixed in locker room ❤

[@sungazer454]

Cosby sauce!

[@vegbetle]

3:02 insanely cursed mechanism, you should probably double check those before you post them.

[@integral_chemistry]

LMAO yeah I think I'm just going to hand draw them from now on. I was trying to use this freeware to design the mechanism because all the good software for this kind of thing is more expensive than I'm willing to spend. This software made bond lines comically large compared to functional groups, and it was extremely hard to get arrows to actually point to what I wanted. There was also no tool I could find to make arrows that could show the movement of electrons.. So yeah I think its just back to pen and paper and do my best to make it look pretty lol

[@theJOYSofANALpenetration]

​@integral_chemistry my friend has chemsuite on her site available for free, it could help a lot

[@aryanprivilege9651]

Why did you clamp all rb necks? Always told unnecessary and dangerous . Didn’t see opening? Not that you’d do a closed system!