> chemistry > esters > make-ethyl-propionate-by-fischer-esterification-nurdrage

Make Ethyl Propionate by Fischer Esterification

NurdRage - 2015-12-01

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In this video we synthesis ethyl propionate by fischer esterification of ethanol with propionic acid. 

This video sponsored by:
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Rippertear - 2015-12-01

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

SinBae - 2015-12-01

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

Rippertear - 2015-12-01

I know, I simplified it slightly enunciate my stupidity.

BlackMoth27 - 2015-12-02

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

GeoDude 40 - 2015-12-01

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

GeoDude 40 - 2015-12-03

+Eric Kuhn hahaha I have honors to😃

GeoDude 40 - 2015-12-03

+John Lepeska yea I understand, I want to work in the science field after college so I try to watch as many experiments on YouTube and I have a mini lab in my garage just to do fun stuff.

MrLittlelawyer - 2015-12-23

+Space___ _____BAR Then you are definitely on the right track. I'm in college now studying to be a chemical engineer, and one thing I've learned that is certain, the classroom may teach you a good deal, but it can never substitute for your own learning. You have to experiment and read on your own to really succeed.

GeoDude 40 - 2016-09-14

@john black Yea, but i haven't used it for a month now I need to get back on it. My AP Physics homework taking all my free time after school, probably going to start doing labs when my brother comes to visit.

Nothing\ - 2019-05-05

Just keep watching stuff and it'll make snse eventually. Look up what you don't get.

Dean Leggo - 2015-12-02

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 - 2015-12-02

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

XXCoder - 2015-12-06

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

Kyle padilla - 2015-12-03

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

Rumpkisser96 - 2015-12-01

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.

Glace077 - 2015-12-01

so what does this do?

Alejandro G - 2020-05-25

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

Connor C - 2015-12-01

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

Kachel94 - 2015-12-01

You should really shout yourself a new thermometer! haha

ToTouchAnEmu - 2015-12-01

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?

crock - 2015-12-01

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

Evan Stephenson - 2015-12-01

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

Noob - 2015-12-01

Incredibly great source of information.

Zoan - 2015-12-01

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

ShadowDragon8685 - 2015-12-02

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.

Roshkin - 2015-12-01

Thanks NurdRage! Always enjoyable

nunya bisnass - 2018-12-01

But can you make it smell like death?

tom bobbin - 2018-10-08

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.

Gary Card - 2015-12-09

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.

nope - 2015-12-10

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 - 2015-12-10

+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.

PNS SHOGUN - 2015-12-01

Sure beats store bought!

Mr. Reinterpret Cast - 2015-12-15

What would dissolve the magnetic stir bars? :)

Jad Ghalayini - 2015-12-21

+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

Mr. Reinterpret Cast - 2015-12-21

@TheTechnic Lord Thanks for the reply :) 

yourmamaisphat - 2015-12-01

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...

TM80 NotGoodWithNames - 2015-12-01

I am wondering how duralumin is made

Platinum Skies - 2015-12-01

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

Gaming Master - 2015-12-01

5th like!!!

mynameismatt2010 - 2015-12-01

How's Fallout coming?

DeVon Lewis - 2015-12-01

First comment nice vid today

Stephan Harz - 2015-12-01

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

Krustacean - 2015-12-01

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

Rgmekanic - 2015-12-03

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.

AMYAS Seek Truth - 2015-12-01

Who thought of Breaking Bad?

Forrest Culviner - 2015-12-04

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

Alan Ball - 2016-01-13

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

Kyle M. - 2015-12-01

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

ImVeryBrad - 2015-12-01

I got that nerd rage!

Cooking With Cows - 2015-12-01

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

Gregg Macey - 2015-12-02

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

Alex Petrov - 2015-12-04

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.

Neceros - 2015-12-01

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 - 2015-12-23

+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.

Moris Mihovilovic - 2016-02-23

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

Entra - 2016-02-19

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

Daniel Nebdal - 2016-06-14

"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.)

Entra - 2016-06-14

+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

NolanSyKinsley - 2015-12-01

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

O̧͎͂t̪ͨt͖̎m̗ͥ͝a͔̞ͦ̚r̂ - 2015-12-01

+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.

ZakuraTech - 2015-12-01

+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 - 2015-12-01

+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.

O̧͎͂t̪ͨt͖̎m̗ͥ͝a͔̞ͦ̚r̂ - 2015-12-01

+ZakuraTech There is a reason why this is the way it's done in the industry. Yes, it may be a relatively high initial cost, but if you look in the right places, you can get some great deals. Let's say you want to poduce in the same scale as in this video. You won't need more than 5-10 grams of resin. It won't cost a lot and if taken care of, you won't need to think about it in a long time (a professor has used some in esterification reactions for like 3 years without the need for reactivation). It's also not impractical. Just put it in a steel wire mesh and you can leave it there. It's actually more practical. Perform your reaction, take the products, dry the resin a little, repeat. It takes no more than 10 minutes.
We've found that 3-1 ethanol excess is an efficient mixture (even best if you can recirculate after separation) and 5%wt resin. In a reactive distillation set up, you can get 99% pure products, compared to the typical 40-60%. It depends on the specifics of the reaction, though.

Yaldabaoth - 2015-12-07

+Nolansykinsley What the others tried to say before going off to rant, is "Yes. Removing the water is the best way." You should use a Dean-Stark-Apparatus (if possible) or even a Soxhlet extractor charged with a desiccant like Na2SO4 or MgSO4 would do.

Royyan Ahmed - 2020-02-14

Thank uuu

Opal Dragon - 2015-12-01

any other plans to do other flavoring agents?

Estevan Martinez - 2015-12-02

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

freeNode5 - 2015-12-01

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

Peewee0413 - 2015-12-09

make dichloroacetate

Jason Teh - 2015-12-01

What is Ethyl Propionate used for?

Gareth Dean - 2015-12-01

+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.

SSJG GOKU - 2015-12-01

What is Ethyl Propionate used for?

Gareth Dean - 2015-12-01

+SSJG GOKU Making an AIDS medication that has recently been made very, very expensive.

SuperNova - 2015-12-01

% discount.