Chemistry Experiment: Ether Synthesis by Distillation

[SilverCalculatorApp]

cool video, thanks for sharing!

[ytmachx]

@SilverCalculatorApp Thanks for watching!

[kakashi0909]

first of all whats an Ether? you mean like Ether from final fantasy game that restores MP? -_-

[ytmachx]

@kakashi0909 My guess is that the "ether" used in Final Fantasy is....well...a fantasy, and not real. The ether in this video has solvent and anesthetic properties which are quite regularly exploited.

[kakashi0909]

@ytmachx hahahahaha to think someone will really do answer in a nerdy way..... hah.... you nerds are sickening

[ytmachx]

@kakashi0909 Your childish reference to and preoccupation with the "fantasy game" is likewise, pathetic.

[gosdenmum]

Hi, nice vid, what temp did you run the first part of the distillation, I was told it should be about 130c, is that correct?

Thanks

[ytmachx]

@gosdenmum Please read the description.

[staratsx]

very nice setup. why not just distill the ether from starting fluid?

[ytmachx]

@staratsx This is a synthesis video.

[jmneissa]

why did you not use a column during the distillation? Wouldn't your overall all yield have greatly improved?



[ytmachx]

@jmneissa. I believe it is easier to first synthesize and then purify. I don't think that a column used during the synthesis would increase yield. The product would still need to be washed and dried. Using pure reactants and running the bath at the proper temperature would make most of the difference in yield. The bath could also have been used to dehydrate another 250ml or so of EtOH before becoming useless.

[drfatleg]

What kind of adapter is that in middle of the 3 neck flask? The one being held by the clamp in the beginning of the video. It looks like it allowing the drip to go into the alcohol without splashing. Where do you get these?

[ytmachx]

1 year ago; @drfatleg The adapter is a strait drip adapter x 150mm extension below the bottom inner joint. The outer and inner joints both being 24/40. The tube extension i.d. is a bit large though, at approx 10mm.

Please read the comments.

[RatkoUSA]

Beautiful 

[ytmachx]

@RatkoUSA Thanks!

[Chantheman5]

he did the experiment at 5:08 got it

[LemoneyFishmas]

0.22 - 1.00  I need to piss now :P

[douro20]

Doesn't Everclear have some sugar dissolved in it?

[ytmachx]

@douro20 Your point being????

[douro20]

@ytmachx

Well, I wasn't sure if it would affect the reaction.

[ytmachx]

@douro20 I'm not using EverClear straight from the bottle.

[commercialmats]

That is something I have never seen before. Thanks for sharing.

[ytmachx]

@commercialmats Glad you liked it!

[sm3a14]

Oh, sorry, should be sodium hydroxide

[ytmachx]

@sm3a14 The sodium hydroxide removes most of the water. No NaOH, more water in the ether.

[sm3a14]

Thanks =]

But, what if I didn't add sodium carbonate to wash the mixture?  The result is what?

[ytmachx]

@sm3a14 Sodium carbonate???

[sm3a14]

I would like to ask what will happen if i forget to add 1,boiling chips in boiling step,

or 2, sodium bicarbonate in washing step.

[ytmachx]

@sm3a14 If there are no boiling chips you may experience bumping. Sand is used instead of boiling chips because boiling chips are usually dissolved by strong acids.

Sodium Hydroxide is used to wash the raw ether to remove water. The rest of the water is removed with Calcium Chloride in the final distillation.

[ProxySpam]

I would add an anti foaming agent, that shit don't look too good lol I wouldn't sleep well leaving it overnight ^.^

[Ibogaine306]

Why do you put the flask you are just about to heat into the freezer? Honest question.

[ytmachx]

@Ibogaine306 This is because, when the acid is added to the alcohol, there is a strong reaction that produces ether. Freezing the two components first, slows this reaction.

[Ibogaine306]

I'm hungry.

[carjim123]

how many times can be used the same sulfuric acid for ether production and is it possible to clean that acid once is not more usable to use it again ?. how much ethilyc alcohol is needed to produce 1 liter of ether.

Thanks.

[ytmachx]

@carjim123 I think that you could run about 1.5 liters through the bath before it is useless. Doing it this way, it takes about 2.5 liters of EtOH to make 1L of ether.

[carjim123]

what is the use of the residual from diethyl ether destillation? and what is the amount of ingredients to produce one litre of ether?

thanks

[ytmachx]

@carjim123 The residue can neutralized and discarded. Scale up 3x for a liter

[Phacias]

Is it Your kitchen or a lab? I am just curious ^^

[ytmachx]

@Phacias It's the kitchen in an office building.

[cabtrfg]

@spiff873

you can also use 1-2% ethanol as a radical scavenger to prevent peroxide formation. The only problem with this is that it raises the polarity of the solvent, so be mindful when dry ether is needed.

[surplusdriller]

whay the elaborat cooling settup? isent tappwater sufisantly cool?

[ytmachx]

@surplusdriller Ether has a low boiling point, about 35*C. My tap water is about 32*C and room temp about 35*C. I prefer to have the condenser quite a bit colder that the boiling point of the condensate.

[spiff873]

Lacking, BHT, how effective is it to use NaOH as a stabilizer? Any clue how much to use?

[ytmachx]

@spiff873 Lacking BHT, I would put the ether in a dark colored bottle with copper turnings. I don't know about the NaOH for stabilization.

[evsonjunior]

why you are using sand? and what you do to control the production of the ether peroxide?

[ytmachx]

@evsonjunior Sand is for anti-bumping granules,(most other types will dissolve in conc. sulfuric) Ether is stabilized by limiting light ,air, and adding a very small amount of BHT,(butylhydroxytoluene)

[Lorentz5]

man you got a nice setup here

3 neck flask, pressure equalizing dropping funnel, 2 condensors, lab-grade reagents... and it's all so nice and shiny

[ytmachx]

@Lorentz5 Thanks

[Lorentz5]

does the second condenser really make a difference?

[ytmachx]

@Lorentz5 Yeah, it does condense a small amount of ether vapor. If you don't use it there is a strong smell of ether during the distillation.

[hkparker]

Sorry for all the questions :P... I recently bought a drip extention adapter because the one I made for my video won't last. I bought it from expediglass on ebay (great seller!, I checked out their website) and the glass tube doesn't extend to where the solution would be. My question is is it nessicary to go underneith the solution? Because I could melt and add another glass tube to my adapter but I don't want to do that unless nessicary. Thank you!

[hkparker]

What is the safest way to dispose of the left over solution in the reaction vessel?

[ytmachx]

@hkparker Just neutralize the acid and pour it out.

[hkparker]

@ytmachx ok thanks, that's what I'm doing, I just wanted to make sure its safe

[darcyryan99]

that looks pretty complicated haha, id like to try it but i prob cant get half the stuff needed

[mmaaxx1198]

Would it be worth while to do this with an argon atmosphere? I assume a nitrogen atmosphere would work just as well. Just seems like there is too much air in the system for it to be safe... or rather, as safe as i'd like it to be. Had a organic chem lab where we were vac-distilling MeOH with a flame and the girl next to me forgot her boiling stones and almost bumped the setup apart!

[ytmachx]

@mmaaxx1198 I'm sure that argon would work very well. I use nitrogen because it is much cheaper. Vacuum distilling always seems to have a tendency to bump.

[spotlightman1234]

i wish i could get ever clear :/ can you help?

[ytmachx]

@spotlightman1234 I don't sell or provide chemicals.

[spotlightman1234]

@ytmachx no i ment like how to get it

[TribEra]

Would you mind giving an itemized list of glass components that you are using in this set-up?

[ytmachx]

@TribEra Well, let's see.

1 liter 3 neck flask, angled thermometer adapter, drip extension adapter, 500mL pressure equalized addition funnel, distilling adapter with 10/30 thermometer, jacketed cool coil condenser, Friedrich condenser, 1 liter receiver flask. 2 liter separatory funnel, 105* vacuum distilling adapter 500mL receiving flask.

[lexichronicle2]

edit: 1.30am? so i'm not the only one doing this kind of thing at those times....

[ytmachx]

@lexichronicle2

yeah

[lexichronicle2]

I've seen that gear before, my honey bunny! :P I'll be joining in on the discussion shortly I expect... soon as the replacement bits of glass arrive and I'm confident it's going to go to plan.

I hope those clamp stands are real darn heavy. I'd be shitting my pants with all that high up. That's where my last receiver bend met it's demise... :D

Stick some house bricks on the base if they're a bit shaky, that's what I forgot when the bend died

Thanks for the thread and video contribution!

[ytmachx]

@lexichronicle2 Thanks mate.

I make the ring stands from 10mm x 100mm steel plate with 30cm platform,feet made from the same steel,welded on the ends. They are quite heavy.

It's always sad to hear about broken glass :{

[nucleochemist]

Your cooling setup is outrageous! I love it :D

[ytmachx]

@nucleochemist ThankYou!

[Grundalizer]

I wish I had $2,000 worth of glassware so I could do some sick synthesis. Nice setup, and also good job explaining the process, I dislike when people make videos and don't plainly write out WHAT they are doing or WHY

[ytmachx]

@Grundalizer Thanks!

I also agree with you about the lack of descriptions on most videos. :{

[hkparker]

Excellent synthesis, id love to give this a try because ether is extremely hard to get in the united states but it very useful, but need to get an addition funnel. Well done!

[ytmachx]

@hkparker Thanks!

[ytmachx]

@hkparker Thanks!

[ytmachx]

@hkparker It is important to note, that the addition of ethanol is added below the surface of the reaction mixture with a drip extension adapter, because the reaction mixture is far above the boiling point of ethanol. You can find the adapter on ebay.

[hkparker]

@ytmachx Thanks for telling me, so if I were to not use one the ethanol would just distill over without ever reacting with the boiling mixture?

[ytmachx]

@hkparker Exactly!

[hkparker]

@ytmachx Cool, Ill be giving this a try in the next few week. Ill let you know how it goes or if I have any problems. Thanks for the help!

[discaras]

why did you used sand in the reaction mixture ?

[ytmachx]

@discaras The sand is for anti-bumping granules. Most other types can't handle conc. sulfuric.

[discaras]

@ytmachx :o very smart

[xR0WDYx]

is there a specific temperature needed to prevent elimination as opposed to conversion to ether?

[ytmachx]

@xR0WDYx  Yes, the temperature should be kept under 150*C

[torpex808]

What kind of setup are you using to pump your cold water through the condenser. I finally got a real condenser...just need water to cool it, you reckon an aquarium pump will work?

[ytmachx]

I am using a pump for a water fountain. Actually ,I'm using two of them. The one that pumps water through the cooler is about 180 watts. The other just pumps cold water from a pot in the sink, It is 42 watts. I got both of the pumps at OSH.

[antiswattt3]

my chemistry teacher likes to use ether (petroleumether in danish) not sure if its the same as what youre making.. but i guess as its extremely flammable :P he gave me a little tip.. its used on farms, or was.. when it wasnt illegal.. to start tractors with diesel motors in winther.. (:

[ytmachx]

There are many different ethers. Diethyl ether is used in starting fluids. Check the contents on the can. It can be distilled from these solutions. Some of the brands contain 75% diethyl ether.

[antiswattt3]

well ether is used in the production of hash and also robbers and such use it for putting onto gloves and then holding them onto peoples mouths/noses, they faint.. im not sure if the petroleum ether was the one that makes ppl faint.. cuz i sniffed some on cotton.. lol he didnt tell me it was ether before i sniffed alot.. smells good (:

[ytmachx]

Diethyl ether is the least toxic.

[antiswattt3]

hm.. as flammable as the petroleum ? (: i think its the same thats forbidden in denmark..

with oxygen is a really powerful mix for sure :D

[ytmachx]

It's explosively flammable in just air alone.

[antiswattt3]

hm.. i tried to ignite gasoline in a bottle, wanted the gas to evaporate.. but the pull string thingy got wet somehow.. and it failed.. :/

i need electrical ignition.. need a car battery charger :/

i could play around with ether for hours :P might even be possible to make some napalm like substance with it? (:

[ytmachx]

Yes, that's right. The reaction mixture temperature is above the boiling point of ethanol,so delivery below the surface of the reaction mixture,with time to react, is necessary. The EtOH is delivered at roughly the same rate as the ether is produced.

[ytmachx]

The adapter is a strait drip adapter x 150mm extension below the bottom inner joint. The outer and inner joints both being 24/40. The tube extension i.d. is a bit large though, at approx 10mm.

[svenp]

Wow, this is wonderful. Great videos.

Wish I had your glassware...

[ytmachx]

Thanks!

[torpex808]

I'll have to improvise a bit there. So you have to slowly add the ethanol from above? What ratio H2SO4 to Ethanol are you using, and what kind of oil is being used to heat the flask?

[ytmachx]

All the information is in the video description....on the right. The flask is not in an oil bath. The heating is provided by a "mantle". The mantle is an electric heating element in a hemispherical shape housed in the aluminum cylinder. I would suggest just using a water bath to heat the mixture.

[torpex808]

I have some really simple pyrex glassware.....but I don't even have a distillation flask or anything like that. Maybe if I suspended a simple glass tube in ice it would act as a condenser. It would really interest me to learn how ether was made in the 1800's.....I believe they used a different synthesis technique (with anhydrous ethanol).

Well i'll make sure to post a video if my clandestine method works. Thanks

[ytmachx]

The glass tube in ice water would definitely work for the condenser.

[mildronate1]

For destilation need Liebig cooler

[torpex808]

Would it be possible to perform an ether distillation in this fashion without this fancy gear.......would a makeshift condenser, etc. be effective? And would it even be half safe? I'm talking about distilling a small amount of relatively pure ether. Your equipment is top notch man. What do you do?

[ytmachx]

Sulfuric acid is corrosive and ether is a good solvent. I don't know any material that will work to distill pure ether,other than glass. I'm an electrician/ machinist. Chemistry is just a hobby.

[1ukjunglednbraver]

i wish i could get everclear in the uk.....this may be a stupid question but could i use methalyted sprits its 90% Ethyl Alcohol 10% methyl alcohol...and has a little something in it that makes it taste very very bitter so tramps dont drink it as going blind or dyein isnt enuff to stop them..

[ytmachx]

Yeah, I think you could but your product wouldn't be pure. Try distilling the strongest grain alcohol that you can buy.

[1ukjunglednbraver]

i could its quite expensive tho probly be best just to brew it myself...its like 12£ for a 700 ml bottle 40% alcohol..and only 2£ for a liter of that methalyed spirit 90%...or very very cheap if i brew it myself...

[ytmachx]

Wow! That is expensive. I paid $18 for 750mL of 75.5%

[1ukjunglednbraver]

its is but its mostly tax your paying...its illegal to distill it yourself but i think ile take the risk

[ytmachx]

Post your results if you can :}

[ReiWithAnI]

what size is that graham condenser? and did you build that stand yourself?

[ytmachx]

It's not really a Graham condenser. It is a jacketed cool coil. The basic construction is a cool coil inside of a large diameter Liebig. The joints are 24/40 and the jacket is 9 3/4" long. The secondary condenser is called a Friedrich. Yes, you're right, I made the stand.

[ReiWithAnI]

:O youre my hero lol

I recognized the Friedrich but something about that one I thought was a graham was odd to me. must research more lol

and are you willing to make another one of those stands? am willing to pay

[antiswattt2]

nice.. ether is illegal in denmark.. i sniffed some in school haha :P i like the smell.. was on cotton but my chem teacher didnt tell us it was ether before we all smelled it o.O would be nice to just go make some chemistry stuff whenever you wanted to.. :/

[ytmachx]

Illegal? That's too bad! And I thought things were tough over here! I will consider myself fortunate.. Rotting fruit gives off ethene gas and smells just like ether. It's a good smell.

[antiswattt2]

ya it was used to put on gloves and then thugs went into houses.. put the glove infront of ppl's noses that they fainted.. my mom once sniffed into a big bottle of ether when it was illegal.. she says she just fainted right at the place ^^ i think it smelled abit like some sweet acetone.. strange i didnt faint with all of that ether i sniffed xD

[TmSensis]

WoW, where did you get all the equipment? I can't find here in hungary a good place to buy them...

Anyway, good vid, if i'm correct, a "few" degrees higher (ca165C) and elimination of H2O would happen from EtOH and you'd get ethylene (ethene)

[ytmachx]

I got the glassware on ebay, and yes, you are right about the critical temp. This is why I kept it under 150C

[DaniCalifornia44]

Na szia én asszem tudok egy helyet, ahonan lehet rendelni én is nemrég rendeltem egy rakat laborcuccot, igényesen becsomagolva küldik, csak a futár nem törődik a fragile felirattal, így egy mérőhengerem eltörött, ez igaz, de csak a talpa és meg tudtam ragasztani epoxyval. Írj, ha érdekel a dolog, de ne itt kommentbe.

[mewrox99]

I love organic chem.

[bamboo4tameshigiri]

beautiful

[ytmachx]

Thanks! and thanks for the sub :}

[Tommy8627]

nice equipement ! it might sound stupid to you guys... but is there an other use of ether .other then start up diesel engine ???

[ytmachx]

Thanks, and, Yes there is. It is most often used as a solvent for extractions.

[nautic546]

@Tommy8627 yeah its also used for the synthesis of organometallic compounds.

[angryaape]

I've been wanting attempt this for a while now. It's good to see it actually works..

[cobrasniper555]

Very impressive ytmachx! I can only wish I had the same skills you do. Keep up the good work!

[ytmachx]

Thanks again!

[Voldemort1857]

i didn't understand this one. what is the point? did you made already a product somehow or it's just an experiment of reaction?

[ytmachx]

The reaction produced diethyl ether.

[Myfanwy94]

nice, but didn`t you took a bit to much H2SO4?

And a huge amount of organic sulfates are leaving back. Very toxic stuff.

[ytmachx]

I followed instruction to the letter.(exactly) The process was invented more than 250 years ago by someone much smarter than me.

[anfokg]

You must be very happy for this XD

[ytmachx]

Yeah, I was really pleased with the results!

[liquidgrain]

Like me I assume you take much pride in your apparatus! Very productive and original synthesis! 5/5

[ytmachx]

Thanks,liquidgrain! I do actually enjoy collecting glassware quite a bit. Sometimes I get a new piece and then think of a way to use it.

[NOBOX7]

nice set up bro, what will u do with the benzine

[ytmachx]

Thanks! The ether is a great solvent for extractions.

[Hydroxybenzeen]

Ether is not just one compound, ethers are organic compounds with a R-O-R binding, the restgroups can be any functional group like CH3- of Ph- groups. I guess you are making di-ethyl ether here since ethanol is used as a starting product.

Be carefull deu to the formation of organic peroxides!

But verry nice synthesis! 5 stars!

[ytmachx]

Thank you and Yes, you are correct on both. I should have said diethyl ether and those peroxides can be a problem.