Make Ethyl Propionate by Fischer Esterfication and Molecular Sieves with a Soxhlet extractor

[@elnombre91]

Soxhlet extraction is a criminally underrated tool in synthetic chemistry. People need to get in the know.

[@MuzikBike]

Good to see you're still exchanging carbon and oxygen with your environment.

[@NurdRage]

My personal contribution to global warming and climate change

[@MuzikBike]

Well you're still eating almost the same amount of carbon. Which brings up the weird question: every time someone eats something, how many atoms of that food have passed through their body before?

[@Teth47]

I believe the answer is ~every 5 years you'll end up with some of the same atoms in you. It took about 10 years for the air Einstein breathed to disperse throughout the atmosphere, and now about every month you'll breathe some of the same air he did. You're also likely to have eaten some Carbon that was once a part of Hitler.

[@lefr33man]

+Muzik Bike That's not very specific, as you still do that even when you're dead :)

[@0xbaadf00d]

Don't forget hydrogen.

[@empt60]

Glad to see a chemist using something in an innovative way. A lot of very useful equipment is often overlooked because people don't think about it being used for synthetic purposes.

[@lefr33man]

oh cool, I always wanted to make make ethyl propionate by Fischer esterfication and molecular sieves with a Soxhlet extractor !

[@rutwizz]

lefr33man I didn't have a "Reaction" to that comment!

[@MartKencuda]

I was just thinking the other day "Man, it's been a while since I made ethyl propionate by Fischer esterfication and molecular sieves with a Soxhlet extractor."

[@Scalemailmailmail]

If I had a dime for every time someone made ethyl propionate by Fischer esterfication and molecular sieves with a Soxhlet extractor, I would be a millionaire!

[@NeuronalAxon]

Looks like you're in luck!

[@jaredmorein]

Very interesting, and I plan to use this genius idea with the molecular sleeves and Soxhlet in a Fischer esterification I will be doing soon. However, I would like to make one recommendation, I've found in my experiments with ethyl esters that any leftover ethanol tends to drag a LOT of your precious esters into your water layer while doing a water wash. I was losing more than half of my product from this method. A better method would be to either simply just strip off the ethanol first, or use another extraction solvent such as an ether or a ketone that is immiscible with water. Since the ethanol tends to drag your product into the water, the other solvent would help keep more of your ester in the organic layer. The question just becomes whether you care more about time or yield, since any solvent you add to the wash is something you have to distill off later if you want pure product. Thanks for all of your great work, I very much enjoy your videos! Keep them coming!

[@swedneck]

Holy shit someone already added this to the "see also" part on the wikipedia page for ethyl propionate.

[@NurdRage]

Was it you? :)

[@swedneck]

NurdRage Someone called "halfcookie" apparently.

[@old-bitprogaming4857]

NurdRage lol

[@sivalley]

THE UNKNOWN Get out. This is a chemistry channel, not political science or social engineering.

[@XXCoder]

Suggest just report.

[@devjock]

93% yield, well done sir! That is an amazing improvement over the last attempt, and it seems to be less work too. What a great trick!

[@myrusEW]

Dude! I totally understand that title COMPLETELY and I was always wondering how I could do this! Thanks, NurdRage!

[@eriko807]

THE UNKNOWN it was sarcasm dumbass.

[@1Bigredox]

I made a similar chem way way back in grad school from benzyl chloride and sodium cyanide, but I don't remember using an iodide salt catalyst. I followed a procedure from a Russian paper I've long since forgotten the details of. The reaction mixture turned a nasty brown-black color, required vacuum distillation, and smelled up the entire lab building the day I spilled some. This is so much cleaner!!!

[@firstmkb]

I loved the different procedure that doubled the yield, and the (too brief) discussion of additional possibilities. Thanks for posting!

[@geologist_luna]

In my lab I use similar sieves to remove boron from rocks to assist in the determination of the source of fluid mobile elements. I love the use of these as they really make life a lot easier than doing it the old wet method. Great vid.

[@NurdRage]

First video of 2017

[@TKGMoMoSheep]

Finally!!

[@Camilo19832001]

NurdRage bout time!!

[@theshippuuden]

Gr8 vid m8

[@brozach1394]

Greatly worth the wait. This video was Awesome!

[@drvelocci]

NurdRage great vid. Love your videos. I've been a subscriber since before you quit for a bit. Probably 4 years ago

[@unreachablechemistry5105]

A great video! I love that the soxhlet apparatus, which has been designed to perform one job, has so many other uses as well. Very neat trick.

[@drummer265]

I barely understand most of his videos, but damnit do I love watching them.

[@j_sum1]

Clever. I like this approach. Coincidentally, I received my soxhlet in the mail yesterday. Plenty of fun awaits.

[@jopomeister]

I have no idea what any of this means but it's peaceful and weirdly enjoyable to watch. Nicely done!

[@OrbitalRose_01]

that's an impressive improvement over the previous process!

[@TanaNicoleKitty]

This is my favorite channel on KZbin. Glad you're still making videos!

[@spantim]

I had this idea for some time and it's great to see you actually do this. Maybe you could, like you said, use an excess of propionic acid and boil off the ethyl propionate. If you remove all the water from the reaction you can remove the acid with sodium hydroxide and you'll get pure ethyl propionate.

[@zock4419]

You are my favourite KZbinr !

[@markbell9742]

Very nice, a very useful technique. Cheers, Mark

[@aga5897]

Wonderful lateral thinking ! So many people just use the bits of glass how they were intended.

[@jimsmindonline]

Jealous of your awesome collection of glassware! Glad to see the first vid of 2017, keep up the good work!

[@xXTheFrancoXx]

your videos are very inspiring

[@stcrussman]

I understand what "make", "by" and "with" mean, so I should be able to get the basics of this.

[@RoelfvanderMerwe]

stcrussman I feel you bro

[@eriko807]

THE UNKNOWN you are the single-digit IQed moron that is spamming edgy comments on this video. Please leave, nobody wants you here.

[@stcrussman]

You're not a good person.

[@agent475816]

Well ethyl propyonate is a chemical (product). Fischer esterification is a mechanism proposed by Emil Fischer where an alcohol and a carboxylic acid react to form an ester (hence the name Fischer esterification). Molecular sieves are those bead things that absorb water, and soxhlet extractor is the thing he showed.

[@eriko807]

THE UNKNOWN Based off the fact that you are getting triggered over a person's comment, I would say you are the one who needs a life :) Also, just because someone gets likes on their posts doesn't mean they are liking their own comments. But I know that is hard for you to understand considering nobody likes you :)

[@Nerd-px7fn]

Great to see you uploading again!

[@FranktheDachshund]

Awesome work around!

[@bromisovalum8417]

Soxhlets are cool, also great for making plant extractions.

[@brettreiff]

Hello. I an a HUGE fan of your work. I had a quick request. I was attempting to shop around for a more efficient condenser that I had recently found. I am now looking for a more efficient fractionating column as of now. I was wondering if you could do a video about the various types of glass condencers, their efficiency and niche uses as well as the fractionating columns. You were the person who inspired me to start studying in this field. Perhaps you can assist me in my cause right now. Thank you either way. And I will continue to enjoy your videos and drinking in all the knowledge I can. So even if it's touching on the subject just a little I feel it would be helpfull.

[@science_and_anonymous]

I love these types of reactions. I remember first doing this but with making methly salicylate

[@tyopsie]

I like how you showed putting the apparatus together. I have a small idea. maybe you would want to show us how the flow works with a quick Visual w arrows and such. Great vid!

[@billsmathers7787]

Good luck on the Claisen! I've had lo luck getting them to work with sieve dried alkoxide.

[@Bluegeneral05]

Love your videos man! My girlfriend is a Biochemist and I love learning about chemistry and asking her questions. Kinda wish I had gone for a Chem degree now! Keep it up man!

[@confusername6572]

You were correct to plan ahead

[@tylorbray]

Good Video, thumbs up.

[@evilplaguedoctor5158]

That is brilliant! I don't think I would ever have thought of that (but then again, I'm no chemist :p)

[@matsudaindustries2530]

Can you extract iron from blood?

[@cyan_oxy6734]

awesome idea!

[@jakob1410]

Would dry MgSO4 be able to remove enough water to be feasable? Should be quite inert. But maybe the slurry would be very hard to mix...

[@NurdRage]

A difficulty with MgSO4 is that you need to be able to stir it into the mixture. If it sits still while it's absorbing water then to clumps together into a hard rock that stops further absorption. It could also clog the soxhlet. Give it a try if you want, i think the convenience of sieves is more advantageous.

[@jakob1410]

Yes, the method shown is clearly more usefull. When I use it for drying crude products it clumps up. But using even more loosens it up again. So maybe usefull in certain circumstances. These observations are from lab work with nice excess DCM, EtOAc or pentane solvents and the luxury of a chemical supplier. It is funny that esterfication can be such a hassle when done at home. Great stuff

[@krisztianszirtes5414]

On the other hand what about dry copper sulphate? I cad it cake into a flask way less times.

[@photonthelatios7828]

This gave me the idea of refluxing sodium hydroxide and absolute ethanol over 3A sieves in a soxhlet extractor to form sodium ethoxide for preparation of triethyl orthoformate. I haven't tried yet but we'll see if it works.

[@dimaminiailo3723]

it works

[@fmdj]

could that possibly work with a regular fractionating column that you plug near the top with a bag full of molecular sieves?

[@loganrhodes1899]

I wish I could afford a chemistry set man.. I need lab gear, so much to learn... so many experiments to be done.

[@BlueBeamProductions]

i have no idea what you are making or what you use to make it, but it looks cool!

[@experimentalaquimica]

You can use silica gel?

[@ashW110]

NurdRage. I am quite surprised you didn't neutralize the final product in the alkaline solution. In my video, where I synthesize ethyl acetate by Fischer esterification the ester was reasonably acidic, and I had to neutralize it in the solution of sodium carbonate.

[@NurdRage]

after two water washings the acidity is negligible. The acid almost exclusively remains in the water layer.

[@ashW110]

That makes sense. I though since a slight amount of water is soluble in esters, little amount of acid will still remain in the product, even after multiple DH2O washing. I believe, since this ester will be used as a reagent to synthesize the pyrimethamine initially, the alkaline wash is really unnecessary. Great video, using sieves in Soxhlet apparatus is an excellent idea. Never seen it before.

[@NurdRage]

As said before the acid is negligible. But you'll also note that i'm storing over molecular sieves. Acids react with sieves. So that's a crappy, but still functional, acid removal method. Since the amount is negligible i'm not worried about destroying the sieves, they'll still remain 99% functional

[@ashW110]

Of course, I didn't consider the sieves, now I clearly see your point. I am still very curious to know the pH of the ester you stored in sieves. Whether it is still slightly acidic or neutral?

[@dontcare4177]

Do you ever freeze the water out? "Cold box distillation" I do it with my mead.

[@ЖанибекБекхожин]

Amazing!!

[@ShroomLab]

Does adding magnesiumsulfate (dry) work as well?

[@primarkbandit8535]

Hey. Can you isolate and immobilise urease from whatever source and use it to make ammonia.

[@kapilmamtani8676]

Thank you.

[@rutwizz]

I am 16, and you rock NurdRage. Also, what is that periodic buildup and drain in the Soxhlet Tube from 3:50 ?

[@rutwizz]

Spooky Wizard Well Thanks Though!

[@TV-gv1js]

where I can get propionic acid?

[@jddj5064]

Can you do a Video about extracting the potassium nitrate and sulfur from gunpowder? I feel like it is relatively easy obtained and the ingredients can be used to make some more interesting "stuff".

[@d1s1ntegrator56]

how much does molecular sieves absorb water?

[@Ottmar555]

I would advise to keep the ethanol excess, as it will help drive the reaction forward. We are researching the purification of lactic acid via an estherification reaction, and at least in a continuous process it's still desirable to have some ethanol excess and the extra is simply recirculated. You could also use highly acidic ion exchange resin which makes separation easier and can last for years without the need for reactivation.

[@NurdRage]

true. In this particular case going stoichiometric might still work since the ethyl propionate also has a low boiling azeotrope with water and would also recirculate. If we're going with heavier esters then yeah, excess ethanol may still be necessary. I've been looking for a domestically available source of cationic exchange resin (which can be easily converted to acid). So far i'm looking at water softener resin but i'm unsure if it'll survive organic synthesis.

[@Ottmar555]

It's a matter of process simulation, which is a beast on its own. I'm afraid I can't detail much more of the process, but if you find a way to run a continuous distillation, maybe I could run some simulations for you. Currently we are using lab grade resin, but for home projects I'm considering pool resins, which are way cheaper and there are some which are advertised as highly acidic and in theory should resist. I'll report my findings later.

[@SuperKillerkarnickel]

nice video! I wanted to try to make sodium ethoxide without sodium metal just using NaOH + ethanol the same way. I still have no Soxhlet and not enough time.

[@ZZeeNiCey]

well done

[@skvalparn]

Hi i would Love to see a video showing the process companies use to produce proteinpowder!

[@viru52000]

whey protein is simply the protein rich liquid that is left over from making cheese. Curds is the solid that separates out and is compressed into cheese. Unseparated, it's curds and whey, which you may remember from a nursery rhyme.

[@martinofgliwice1486]

What about using benzene/toluene to drive away water as an azeotrope than returning just benzene/toluene via dean-stark trap?

[@dimaminiailo3723]

This works when both alcohol and acid are non-volatile. TsOH is prefferable to use because of the oxididizing properties of sulfuric acid.

[@RoelfvanderMerwe]

Can you repeat the part where you said about the things?

[@EdSchneeebly]

A thought I had early on, after ''what a great idea!'' was ''would magnesium sulfate or calcium chloride be faster?''. In principle they'll work, and I suspect faster, but are there any practical limitations to them that you'll only realise upon doing it?? I've not got a soxhlet, yet, so can't predict. Nice video!

[@NurdRage]

Calcium chloride dissolves slightly in alcohols and esters. it's not much, but what does a soxhlet extractor do best? extract substances of very tiny solubility. You'll end up with the calcium chloride dissolving in the recirculating solvent and massively contaminating in the product in the boiling flask Calcium chloride could begin reacting with your acids and creating other products. This may diminish the rate or quality of your reaction. Magnesium sulfate tends to clump as it gets wet. You'll end up with a rock-hard mass of magnesium sulfate that doesn't absorb any more water (since the solvents can't access the interior). It's not as soluble as calcium chloride but clumping makes its performance less predictable. Molecular sieves are also simply better than both of them at drying. This is important for azeotropes that have very tiny amounts of water. You might end up taking *longer* to use calcium chloride or magnesium sulfate since they're not good at absorbing tiny quantities of water. You can give it a try, i don't think it'll fail outright. But considering how predictable and easy to handle molecular sieves are, i prefer to use the sieves even if they take time.

[@EdSchneeebly]

Thanks for that! you've saved me a future headache! I've never used molecular sieves as a drying agent, but for my dissertation am mounting them, to produce heterogeneous catalysts in the synth organic lab. What field of chem are you learned/lecture in?

[@VenomsDelight]

I'd be interested in a video about the production of Aluminum Oxynitride. Any chance that can happen?

[@engineeringentropy8965]

Very clever

[@rouvenr1414]

Recently I thought about replacing the molecular sieves with silica gel. Might that work?

[@FPengu1n]

Rather curious why you don't just use stociometric sulfuric acid to dehydrate the water as you go, then extract at the end to obtain your product?

[@netspirit79]

If you want to remove ethanol, you can use 4A molecular sieves in the end

[@vojtator]

Would this be viable with dehydrated calcium chloride?

[@NurdRage]

That tends to dissolve a TINY bit in polar organic solvents, like alcohols and esters. While it's very small, what does a soxhlet extractor do best? extract substances of very tiny solubility. You'll end up with the calcium chloride dissolving in the recirculating solvent and massively contaminating in the product. Calcium chloride could begin reacting with your acids and creating other products. This may diminish the rate or quality of your reaction. But even if that weren't the issue, calcium chloride is good at drying, but molecular sieves are simply far better. This is especially important if you have azeotropes that have very tiny amounts of water.

[@kevins6277]

Well, learned my lesson buying cheap shit from Amazon. The soxhlet extractor I bought came from China, which also took 2 months to get. The siphon was cracked and leaked (fixed that), and the top of the siphon was damn near closed. I paid $45 for this POS. Oh, and the joints were slightly crooked, WTF?!?!?! I will be saving my money and buying from alchemylabsupply. Thanks for the videos, and being able to get the 5% discount.

[@gielzorn9725]

Does anybody know if this esterfication would function under vacuum conditions? Can't seem to find any information on vacuum soxhlet extractions. Would it work?

[@dimaminiailo3723]

It will work, but the Soxhlet is usually used under atmospheric pressure only. The stirring is mandatory, remember

[@lukasstib]

Can I use Soxhlet extractor with 3A molecula sieves for methyl and ethyl methanoate? Is low boiling point MM problem?

[@dimaminiailo3723]

It is better to distill away the formate esters themselves. I prepared methyl formate this way. The good column is prefferable to work with, I have about 300 mm long and performed distillation not too fast, keeping an eye on the thermometer.

[@Automaticguns1]

hey nerdrage i maybe the only one who wants to see this but can u try getting some ferrofluid and try filtering the ferrofluid i just want to see if u can filter it and see what it looks like filtered

[@sriver1283]

Why aren't you using a Dean-Stark Trap and Toluol or Xylol to remove the water? It's easier and you should get a better yield with this method! To remove traces of sulphuric acid you should wash your crude product with a NaHC03 solution! Really enjoy watching your channel

[@NurdRage]

How do you separate the azeotrope of ethyl propionate and toluene/xylene?

[@maachimiste]

NurdRage there have also an azeotrope with cyclohexane ? we can find good solvant for dean stark no ? but it's a good alternative of a dean stark when we can't use good video i love your channel ♡

[@Thingsthatgopew22]

Storing it with molecular sives dont hinder reaction with the water inside the molecular sives, or am I wrong? My thesis: The water is still there, unreacted, just temporary locked inside the sives. All IP in direct contact with it will react with it, given enough time.

[@eriko807]

THE UNKNOWN why dont you use your one brain cell and fuck off. You are an unnecessarily salty being, nobody wants to read your comments.

[@danielf.7151]

Just out of curiosity, would your videos be considered a credible source to use in a publication?

[@NurdRage]

I don't think so. The ephemeral nature of youtube videos, the fact that youtube is chock-full of... not very credible videos... and the fact that there is no editor or peer review makes information presented here highly suspect at best. While i appreciate what other people post here, I'd never use it in my publications.

[@brettreiff]

And with ethyl acetate it forms a Tercery azeotrope of 70.3% ethyl acetate, 7.8%h2o and 9.0% ethanol. Perhaps it would form a similar azeotrope?

[@dimaminiailo3723]

Maybe, but the composition of an azeotrope doesn't matter. With such a bad "rectification column" the water will be distilled in any case

[@DisruptivleySekC]

I only know half the words in your titles, but I love the videos nonetheless lmao. Cheers Nerd. ~Marcus

[@PlasmaHH]

Nice trick, why haven't I seen aynthing like that anywhere else? Is there maybe a superior process or did nobody bother?

[@NurdRage]

it actually is used quite a bit: on an industrial scale. The wonderful thing about it is that it's essentially waste free, the molecular sieves can be regenerated in place by simply heating them and pumping dry air through. For laboratory work, most chemists don't bother and go with the more common dean-stark apparatus or they just use highly reactive reagents like acyl chlorides which get the job done in minutes rather than the hours it takes molecular sieves. Being an amateur, i can afford to be patient and go the slow but safe/cheap way.

[@PlasmaHH]

That explains it very well, thanks!

[@kerrycollins9597]

A convenient route to propionic acid involves oxidizing n propyl alcohol with nitric acid.

[@DaniPaunov]

make a video about "touch powder" (nitrogen triiodide)

[@al_kaloid]

Soxhlet*, dear Dr. n-BuLi ;) Okay, okay, I'm going to watch the video now :P

[@NurdRage]

ah gotcha, fixed!

[@al_kaloid]

This is actually a great method for ester syntheses if one is lacking a Dean-Stark apparatus. Never thought of it, perhaps because I'd still need the mol sieves :/ Guess it's about time.. Thanks, anyway! (One could argue that molecular sieves are a comparable investment to a D-S trap, considering the need of the Soxhlet extractor, but fuck it.. they are far more versatile and I really like the idea :D)

[@NurdRage]

What's cool about this method is that it even works for cases where a dean stark trap doesn't work. A dean-stark trap requires the distillate to phase separate. But in the case of ethyl propionate-ethanol-water azeotrope, it doesn't. I actually tried it and the vapors never separated. Molecular sieves don't need phase separation and in fact work better when the solution is homogeneous. They're a bit more hassle than a dean-stark, no arguing there, but they can be applied to a wider range of jobs when coupled with a soxhlet to keep them safe. I do prefer a dean stark, but when it doesn't work, the soxhlet-MS combo usually does.

[@tggd8423]

No trolling, I need to make this exact compound in the lab tomorrow, lmao. Not using molecular sieves and a soxhlet extractor, though :P

[@computercat8694]

Can you distill beer?

[@NovemberBegin]

damn 93% is awesome

[@sjn7220]

A little MgSO4 would get rid of the cloudiness.

[@williamsquires3070]

What. Happened to your stir bar?! It looks all burned up. :(

[@redneckchemist6506]

He was probably using it with sodium or magnesium. Most alkali metals will react with the Teflon coating and darken it.

[@oppotato5440]

Can you do a lab tour

[@rockyrivermushrooms529]

can you make some ETN?

[@cardboardconnoisseur9155]

+Spooky Wizard Seriously.

[@XXCoder]

Just report and move on. Kills trolls faster by not talking to them and report posts.

[@eriko807]

THE UNKNOWN triggered

[@karlramberg]

Cool

[@lpphoenix131]

It's my birthday today!

[@MuzikBike]

Mine was 10 days ago

[@eriko807]

Muzik Bike mine is in 4 months.

[@pilchtastic]

Seeeev!

[@Metazone101]

Is it possible to make anhydrous alcohol with the molecular sieves? Say from 95% to 99.9% Doh! you have a video on it. Never mind...

[@jacobshin4279]

What do you think of bitcoin prices?

[@eddiebernays514]

have you ever made LSD or DMT?

[@svenhoek]

Are you serious? Only an idiot would admit in a public forum that he manufactures(ed) a controlled substance. My god, people are dumb.

[@0xstev3]

yeah. did you miss his video on how to make lsd?

[@Teth47]

He has specifically stated in many of his videos that he does not and will not consider making illegal drugs.

[@ramunesoda73395]

Make thermite with black iron oxide

[@TheMeilinger]

if only one had a dean-stark apparatus ;)

[@NurdRage]

doesn't work when there is no phase separation.

[@TheMeilinger]

NurdRage ah i see. i though you initially wanted to use this before you broke your dean-stark :D

[@scron7525]

Ground breaking stuff.

[@bhu1334]

first for real

[@TheHuntermj]

BHU1 LORD 33rd!

[@ClownWhisper]

Gaylord Ray J might be able to liberate one spectra-physics argon laser with power supply in fiber optics cable I don't know if you do any experiments they require blue coherent light then again this is not for sure I'm checking. I don't know if you have any interest in this it is a very expensive piece I think it retails for $11,000 and it's only been used five or six times

[@kittyrules]

For some reason youtube keeps on unsubscribing me from you and I missed all of your last 6 months or so of stuff. Stupid youtube

[@RapiDEraZeR]

could you make LSD?