Make Ethyl Propionate by Fischer Esterification

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In this video we synthesis ethyl propionate by fischer esterification of ethanol with propionic acid.
This video sponsored by:
Only HR
Scott Malcheski
osama alharby
David Smith
advisable
Michael Zappe
Emil Mikulic
Dino Capiaghi
Meshal Al-Enazi
James Nicoll
Lord Martin Hill
Matthew Brunette
Collin Wright
Simon Bitdiddle
Cullen Purkis
Samuel Pelzer
Carl Potter
Roger
Max Loutzenheiser
Mathieu Robillard
Phillip Hutchings

[@NurdRage]

So i had to skip ahead a bit and show making ethyl propionate before showing how to make propionic acid. This is because making propionic acid has proven to be incredibly tedious with having to distill liters worth of liquids. Hopefully i should get the propionic acid video ready in a week or two. Ethyl Propionate will be used in an upcoming video on making pyrimethamine/daraprim.

[@brainandforce]

Can you recommend some nice smelling esters to try?

[@Khan-bi6nu]

+NurdRage You still addicted to Fallout?

[@TheChemistryShack]

+NurdRage I love the smell of esters in the morning

[@awesome5678910]

It seems as though you used an excess of ethanol but perhaps you could have used more maybe something like 100ml or so and re flux over some molecular sieves to completely favor the forward reaction, do you think this would work to improve the yield, cause I think Fischer esterifications usually produce a 60-70% yield?

[@Ottmar555]

+Daily Insanity I refer you to my response to Nolansykinsley.

[@Rippertear]

the one sentence I understood: "Finally we made something that doesn't smell bad!"

[@Sinaeb]

+Rippertear - Gaming Videos AKA SDL Benjii TGPASOTSISAPROA(THR)STTLOYTYVM he said : Finaly something that doesn't smell death.

[@Rippertear]

Rem I know, I simplified it slightly enunciate my stupidity.

[@BloodSprite-tan]

+Rem he said "finally we make something that doesn't smell like death."

[@geodude404]

Am I the only one that loves seeing his videos but don't know half or most of what he's talking about.

[@erickuhn2812]

I never have a clue what he talks about but I have been following him since 1000subs, they're just so interesting to follow

[@animethighsexpert276]

same

[@johnlepeska6477]

he could be making words up for all I know. love the videos tho

[@TheRedWon]

+Space_____ _____BAR At first I had no idea, but after taking a couple years of chemistry in college I now understand the majority of the videos (need some more lab experience to understand everything). It's a really rewarding feeling.

[@ppunkk]

+Space_____ _____BAR I did chemistry experiments, mostly inorganic when I was a kid, even had simple home lab, but now I can hardly remember that stuff. Also I'm not an English speaker and doesn't know most of terminology he uses. Something clears a bit when I look up some terms or names in dictionary. And even if I know I never going to do any of those experiments I still watch every video Nurd Rage and Nile Red do. Much like /r/ArtisanVideos on reddit - you just watch that 30-minute hammer forging video or something like that and can't stop.

[@josh987430]

I was going through my old subscriptions and wanted to watch some of your old videos, I was pleasantly surprised to see your back, time to catch up.

[@kylerpadilla]

One of my favorite KZbin channels, keep the awesome videos coming!

[@Rgmekanic]

Thanks a bunch for another vid NR. Any chance we could get another long detailed one like the full process for making luminol? I wouldn't even call myself an amateur chemist, but I love the in depth videos that go through all the changes that are happening. Fascinating stuff.

[@Ausdb]

I really enjoy watching your videos, but this video seems a little rushed. It'll be great if you can spend more time explaining stuff and have a few more pauses. Your chemistry is getting more complex so it'll be great if you can edit it somehow so we can keep track with where you are. An example is how SciShow puts a list of topics/steps/ideas on the side and explains what they talked about at the end. This is very helpful and you shouldn't just copy this, but some type of mapping so we can keep track. :-) Love your work!

[@NurdRage]

+Dean Leggo Thats an interesting idea! I'll see what i can do. :)

[@XXCoder]

+NurdRage Maybe a tree view of videos that lead to final result.

[@CookingWithCows]

One time, in school,more than 12 years ago,we made an ester, out of butane acid from butter, it smelled like pineapple :3 that was awesome

[@Arsonist42]

Incredibly great source of information.

[@Roshkin]

Thanks NurdRage! Always enjoyable

[@ShadowDragon8685]

Are the videos showing off the lab glassware and equipment stuff still in the pipeline, or did they get shelved? I was really looking forward to that glassware expose.

[@alejandrog2825]

Is this method somewhere on paper. I can really use it for a school project?

[@garycard1456]

Video suggestion (electrochemistry): construct a Voltaic pile capable of a large voltage output. All you need are alternating zinc/aluminium and copper plates and an electrolyte (sodium chloride works well enough, but perhaps there are even better ones?) soaked into absorbent material. This is not a feasible 'DIY' alternative to a commercial dry cell battery: the purpose is- as always- to explore the science.

[@ToTouchAnEmu]

I have a question. I have noticed that in several of your recent videos you mention how inaccurate your thermometer is. what is stopping you from picking up one that is more accurate?

[@crock5838]

+NurdRage could you maybe in the future make a video tutorial on how to make Fulminated Mercury Thanks lots

[@kanerhodes8714]

can ferrous sulphate be decomposed with heat to create sulphur dioxide and sulphur trioxide and then be consensed and further processed into sulphuric acid? I read this somewhere and was hoping you could confirm or debunk this. I found ferrous sulphate to be very very cheap and easy to get meaning the sulphuric acid would be easy to make for my experiment but I'd rather not go through the entire process with my amateur equipment only to be dissapointed. if you could get back to me on this I'd appreciate it.

[@itar10n]

Would it be possible to get a better yield by refluxing over molecular sieves like those you used to dry the ethanol?

[@kwinvdv]

Do you yield some ethyl-acetate just by mixing some denatured alcohol and (cleaning) vinegar at room temperature? Because I tried this once and did notice a sweet smell. Or is the main difference that you get a lower yield just by mixing diluted compounds?

[@redneckchemist6506]

+Kwin van der Veen If you heat it up, it will produce some ethyl acetate. Simply mixing them might produce just enough that you can smell it.

[@al_kaloid]

I was wondering why you didn't use an azeotropic distillation with an entrainer like DCM to increase the yield of your product. Had no Dean-Stark apparatus available at that time? :o

[@NurdRage]

+xxdevmodexx wanted to do it this way first.

[@ARVash]

very cool, I wish there was a bit on what it's used for but I'm clearly not the intended audience.

[@nolansykinsley3734]

Would you get a better yield by somehow removing the water produced during the reaction to keep the reaction water free?

[@ThePharphis]

+Nolansykinsley ah, is that why the yield is so bad? I guess you might be able to use a drying agent that won't react with acid

[@nolansykinsley3734]

ThePharphis I have no clue really, I am not even an amateur chemist. It is just a thought I had.

[@Ottmar555]

+Nolansykinsley Esterification reactions are a classic example of equilibrium limited reactions. 40% is a reasonable yield for such a reaction in laboratory conditions. The reason the yield is so low, is because there is an equilibrium between reactant and products (sorry if I seem condescending, but you said you're not an amateur chemist, so I'll explain it a little), as such, there is a constant which relates the quantities of all the substances at chemical equilibrium. In these reactions, the constant is between one and a hundred. In order to make the reaction go further, a removal of the products is desirable, shifting the equilibrium and getting a response in accordance to LeChâtelier's principle. Coincidentally, I'm currently workin on this kind of reactions (the production of ethyl lactate). If better yields are desired, I'd recommend the following set up: First, substitute the sulfuric acid with an acidic ion exchange resin, this will make the post reaction separation easier, and the catalyst can be used repeatedly with only an occasional reactivation. Second, while this is easier with industrial equipment and is more related to chemical engineering than chemistry, a better sistem for these reactions is a reactive distillation one. It is easier done in a continuous process than in a batch one, like this, but the basics should be the same. However, there is a need for some considerations, and you need to make some calculations to determine the correct equipment layout. In this case, you'd need a reactive distillation column (or the lab equivalent) and two separate distillation units with reflux between them. tl;dr. Yes, it's possible to improve the yield, but some reaction and separation engineering is needed. It's a current area of research.

[@zakuratech2673]

+Ottmar555 Given the cheapness of start material and the expense and impracticality of acidic exchange resins, forcing the reaction to completion with additional cheap reagents seems to make more sense. I personally don't do many esterications - but I am curious to know where the diminishing return in these sorts of synthesis lie. In particular, how many equivalents of alcohol would be needed to force the reaction forward; and whether drying agents in solution to take up water would be applicable. I know that under heated conditions sieves function poorly, but I'd be curious to know if it would be possible to soak the rxn mixture over sieves or other drying agent then heat things back up after retrieving them, etc. What are your thoughts?

[@NurdRage]

+ZakuraTech Molecular sieves are actually somewhat delicate. They get eaten by acids and turn into a gooey mud that also releases aluminum and sodium salts of the acid. So not only would they loose their water absorbing ability, they'd also badly contaminate the reaction. Molecular sieves are best used for low-salt, non-corrosive, neutral conditions. Chemical extremes like acidity, alkalinity, or high reactivity tend to damage them. As for getting the water out, it maybe possible using an acidic dessicant like silica gel. But then you'd have a mixture of gel with the ester, not a fun thing to separate. Probably the better approach would be to re-engineer the procedure and use propionic anhydride instead of propionic acid. That would produce much more yield. Problem is making that is way beyond the scope of amateur science.

[@opaldragon75]

any other plans to do other flavoring agents?

[@WheelScreech]

Instructions unclear i ended up with a bomb

[@ThatOneHumanMale]

Could Ethyl Propionate be used exclusively for a flavoring substance? If yes, how bad/good of an idea would it be to consume large-ish quantities of it?

[@ficolas2]

Kiwis and strawberried have a little bit of it. However "Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury" (NFPA 740, 2 in the blue, health category) However I dont know the amount that can be dangerous

[@ThatOneHumanMale]

Hmm, thanks m8

[@chuck52u]

Surely one could use Propanoyl Chloride and Ethanol and combine them directly for a higher yield?

[@NurdRage]

+chuck52u Any suggestions for how to make propanoyl chloride using amateur/home chemistry?

[@chuck52u]

+NurdRage Did not think about that when I posted the above comment. Thionyl Chloride could be used, but that is probably beyond the reach of the amateur/home chemist, and any propanoyl chloride made might hydrolyse too quickly with water vapour in the air to get a worthwhile amount.

[@Glace077]

so what does this do?

[@EJM505]

Why does the mixture turn cloudy when the water is added at 1:15?

[@platinumskies7968]

Can you drink ethal formate and can you make a vid on it

[@alex92569]

I think you have some product lost in the water emulsion. Yield could be better if you broke that emulsion by adding salt to the water layer, or extracted it with some solvent, like ether or chloroform, and then distilled it off.

[@tombobbin2595]

Low yield may be from the condensor. Those short straight walled things are absolute shit. You may want to try hanging a copper wire through it, or investing in something closer to a Dimroth.

[@evanstephenson]

So, when are you going to make fluoro-antimonic acid?

[@macey75]

Am I the only one that thinks "I wonder if that would kill me if I drank it" about EVERY liquid he makes??? lol

[@EntraOfficial]

What does the "reflexing" do to the specific chemicals in the reaction

[@dnebdal]

"Refluxing" - it basically means you boil it but cool down the vapors and let them drip back in. It lets you boil stuff for a long time without losing much or any reagents/water. (Thinking about it, it's very much the same reason you put a lid on a crockpot.)

[@EntraOfficial]

+Daniel Nebdal hey thanks for responding, I'm about to go into chemistry next year so I just want to learn a bit more about these things

[@empt60]

Do you ever check the conversion via TLC or any other analytical method, or is it by trial and error?

[@em68855]

you can. check by ir and gcms

[@empt60]

@@em68855 Well of course you can, but they are kinda pointless to mention for this kind of backyard chemistry.

[@tm80notgoodwithnames58]

I am wondering how duralumin is made

[@EvocativeKitsune]

Propionic acid? I thought it would be called propanoic acid. And ethyl propanoate. Maybe it's a regional thing.

[@limmuquan4796]

apparently it's just another name for it, they mean the same thing

[@longbowlongbow]

What is Ethyl Propionate used for?

[@garethdean6382]

+jason teh In this case making a cheap medication used to treat AIDS patients. Some guy bought the rights to it and jacked the price up like, literally a thousand percent.

[@resadindipa2369]

nurdrage ,show us how to make aluminum sulfate.

[@allowambeBOWWAMB]

What would dissolve the magnetic stir bars? :)

[@jadghalayini1446]

+Mr. Reinterpret Cast The good ones are Teflon coated, and that is pretty tough stuff, very unreactive, corrosion resistant, heat and shock resistant, etc. Molten sodium/potassium and/or hydroxides should do it

[@allowambeBOWWAMB]

***** Thanks for the reply :)

[@aqmi]

Thank uuu

[@TheAmmoniacal]

Ethyl propanoate*

[@NurdRage]

+TheAmmoniacal type propionate into google. apparently it's also a very common term for the same substance.

[@TheAmmoniacal]

Seems like propionate/propionic acid is the IUPAC name, didn't actually know that! Same for butyrate/butyric acid, that trivial and unsystematic trend stops at pentanoate and up.

[@ImVeryBrad]

I got that nerd rage!

[@nunyabisnass1141]

But can you make it smell like death?

[@freeNode5]

I'm guessing it's pretty safe to assume this isn't the same propionate I put up my nose XD

[@yourmamaisphat]

I wish these videos has a brief, "what you might use this for..." part. So not sure why this is good to know. Maybe that's the point though...

[@zoanloid1]

would you be able to make a video with British accent? :D

[@BACCHUS777]

Sure beats store bought!

[@mynameismatt2010]

How's Fallout coming?

[@Billy8ob]

why not include mechanisms

[@lasagnahog7695]

The info in the channel is decent but I would love for some videos without the voice filter. It's quite distracting and I don't see what it adds.

[@NurdRage]

+Eric Loesch You can always turn on the subtitles and turn off the sound. The subtitles are professionally done so they accurately match the audio.

[@Kachel94]

You should really shout yourself a new thermometer! haha

[@kylem.4000]

man 8k away from 600k youtube is full of a bunch of nerds :P

[@officially-ROB]

How do you make cocaine ?

[@ToTouchAnEmu]

Give up on all hopes and dreams

[@mikewright4610]

+1

[@Michaelcallumquinn]

Mash up coca leaves Filter out the white paste Dry out white paste Sell to local drug cartel Buy rice to feed family

[@garethdean6382]

+Rob hartles Send him fifty dollars in unmarked bills.

[@fabiom.8952]

+Rob hartles You call a phone number a friend gave you then meet a shady guy in a parking lot.

[@krustacean699]

Teach us how to make benzoylmethylecgonine. LOL JK!!!

[@gamingmaster8057]

5th like!!!

[@amyasseektruth8246]

Who thought of Breaking Bad?

[@Neceros]

All of your titles make me think "WTF is that? Who knows let's watch". I think sometimes it would be good to know what this stuff is used for, or good for before watching just so I'm on board. I'm no scientist.

[@MrLittlelawyer]

+Neceros He is going to use it to make daraprim I believe. The drug for AIDS patients that was jacked up in a price a while back (the 700$ a pill drug that really costs 20$ a pill or somethin). Nurdrage is making it to show how easy it is to make, and thus why the cost is so outrageous. Its sort of like a protest.

[@devonlewis2505]

First comment nice vid today

[@StephanHarz]

+devon lewis fuck...you beat me...I was going to do the same

[@TheSheepNews]

hi

[@Peewee0413]

make dichloroacetate

[@KaylaRenaeOriginal]

2 to like

[@chimkinNuggz]

do u bathe your victims in this?

[@garethdean6382]

+RuggedALAN I can't see why you would, it's not exactly corrosive, just odorous.

[@XxdjforrestxX]

Why do you use a vocal emulator? Are you scared of society?

[@BillyKnoll]

Getting real tired of these shottasoco ads...

[@Toastmaster_5000]

+Billy Knoll sucks for you - I never heard of it until now

[@BillyKnoll]

Peter Schmidt ad block?

[@corbonzo1]

+Billy Knoll i sure hope not

[@BillyKnoll]

+Corbonzo yeah nurdrage deserves every penny from this. although I don't think he needs it too much as he already seems like a pretty successful guy.

[@corbonzo1]

Billy Knoll well he had to use patreon to continue his vids the way he is, so its not all that well off. adsense has put a huge cut into youtubers revenue. its sad, i disabled it for youtubes domain, i think all youtube content deserves it. and theyre such short ads, its not even a problem

[@GlowingEagle]

That is not aproprionate! Badam tchsss

[@brandonnintendo5439]

Why the fuck would anyone need to make this?

[@g_h_c_dp6010]

hi