The synthesis of ethyl formate

[@ShroomLab]

you are working very professional! I have never done such a "clean" synthesis.

[@lehandron0]

Thank you! Didn't you consider using concentrated formic acid and absolute ethanol?

[@ingensvidcz5390]

If I lack a destilation apparatus, can I only do the synthesis under a reflux and then isolate the product by neutralizing the mix and pouring it into a big ammount of ice cold water? (and then harvesting the ester which should be only slightly soluble in water and thus should form a separate layer)

[@neillcoetzer9133]

That might remove the remaining formic acid and sulphuric acid, but you'll run into 2 problems. First off it will be quite contaminated with ethanol even if it works. Secondly it isn't a clear cut line for solubility. Ethyl formate has about 88g/L solubility in water (and water will have corresponding solubility in Ethyl formate) then because of that equilibrium you'll probably end up sucking some of your formic acid and maybe even some H2SO4 into the Ethyl formate with the water and due to the wet acidic conditions is liable to break down your product fairly quickly. You'll also lose quite some yield due to it Another problem can be that the alcohol that remains will affect the polarity of water in such a way that it could actually solubilize the Ethyl formate, or at least make it a huge pain to sep off, of course this could be decreased by adding more water. But then more yield losses. Another option might be salting it out and that might be the best solution. But distilling is highly recommended However that shouldn't stop you from trying, could give interesting results and would be cool to see

[@ingensvidcz5390]

Yeah, i actually did it. It is quite sloppy indeed, it actually does form a separate layer, but it smells like formic even after prolonget storage over sodium carbonate. The destilation is surely necessary to get a product of a reasonable purity, but still, there is the rum aroma of ethyl formate, even after a year of storage, so probably the H2SO4 got all neutralized. Burning the product results in a bit of an oily residue but the burning is clean, not much smoke and fairly different from burning EtOH. Surely something is there, works as a proof of concept. And thanks for the detailed response, much appreciated.

[@neillcoetzer9133]

@@ingensvidcz5390 ahhh awesome to hear you did it. And nice noting of results as well, good details and basic tests. Always a pleasure to help where I can

[@michaelf7093]

I would have used a larger reaction flask, as you overfilled it at one point. Had there been bumping, your product could have been contaminated. Flask volume should be more than double the sum total of all recatants. I also note you mentioning lacking a second thermometer and stopper. Are you using personal gear, or do you have access to workplace and/or institutional equipment? Being able to read index of refraction would indicate the latter. Otherwise, very good technique!

[@RaExpIn]

Yes, the flask was filled up way too much, but I didn't have a larger one and due to the low density, boiling boint and the sirring bumping was luckily not an issue. This is personal gear and I'm doing all this at my home lab. I was very lucky to get the refractometer as a gift. I would have never been able to buy even a used one. Thanks! :)

[@AcidSnuff]

Nice video! But never add H2SO4 to formic acid as this is used for carbon monoxide generators in the lab. Very dangerous! Formic acid is a strong enough acid to catalyse the esterfication on its own, I can confirm that :) Keep on doing videos and stay safe!

[@dimaminiailo3723]

@@Paonporteur But the speed of esterification does. Oxalic and formic acid can be transfered to an ester without an extraneous catalyst because of their high acidity. The best dehydrating agent for the simplest esters of formic acid is calcium chloride which is much cheaper than sulfuric acid and gives the higher yield.

[@abandonship3]

Does the addition of EtOH increase the temperature of the reaction vessel? Is drop-wise addition necessary?

[@RaExpIn]

The equilibrium of the reaction can be moved further to the right, by having the formic acid in large excess. Due to the boiling point of the ester at 54°C and the acid at a bit above 100°C, it's easy to distill off the first one. That's why the EtOH is added drop-wise. An idea could be to add both at once and distill off the ester, but this would lead to a poor yield and require more acid. More sulfuric acid could also highly increase the decomposition of formic acid to form carbon monoxide.

[@johnblacksuperchemist2556]

@@RaExpIn ,,,,,,,,,,that is why i am always afraid to work with formic acid or formates. I do not know all the ways it could turn in to CO

[@johnblacksuperchemist2556]

@@Paonporteur ....Cool. Thanks for the tip

[@WeebRemover4500]

@@Paonporteur whats the brand name for iodine pentoxide in walmart?

[@chemicalmaster3267]

+Random Experiments Int. - Experiments and syntheses What does ethyl formate smell like?

[@RaExpIn]

It has a strong solvent like smell with some kind of fruity aroma in the background. It doesn't smell like ethanol, but also not like formic acid. That might be the beast way to describe it.

[@justfeesh]

If I used the anhydrous ethanol, do the measurement change much?

[@RaExpIn]

No, because this would only be a few percent difference.

[@medzeek8152]

Hello! Can i have some references on where did you get the instructions for this ? Thank you;

[@RaExpIn]

Unfortunately I found the procedure on a german page for amateur chemists. It's the second method. www.lambdasyn.org/synfiles/ameisensaeureethylester.htm

[@chemicalmaster3267]

+Random Experiments Int. - Experiments and syntheses I have a nice idea for some videos you can make: Could do some videos on extracting (and purifying if necessary) some carboxylic acids from fruits and vegetables. For example, citric acid from lemon juice.

[@RaExpIn]

Nile Red has made a video about citric acid, back then when I was planning to do the same. So I though I'd give it some time, before I'll do it myself. I also had the idea to extract some oxalic acid or malic acid.

[@chemicalmaster3267]

+Random Experiments Int. - Experiments and syntheses That works fine. But doesn´t apple juice have both malic acid and malonic acid?

[@RaExpIn]

Yes, it has, but I thought there might for sure be a possibility to separate both. It has surely been done over 100 years ago.

[@RaExpIn]

I have never heard of that before, but I will have a look.

[@chemicalmaster3267]

Well, do you have any idea on how to separate malic acid from malonic acid? Also what properties these carboxylic acids have? I only know little about them.

[@alishinawi2280]

Professional synthesis please make methyl formate i guess its very similar to this synthWell done 🤗🤗

[@RaExpIn]

You can simply use 92 mL of methanol instead of the ethanol. It's important to cool the receiving flask with ice and add ice to the cooling water of the condenser, because methyl formate has a boiling point of only 32°C. In this case the wasing solutions also have to be cooled down to around 4°C. The rest is the same.

[@sargon6000]

Check out my channel, I recently made a video on its synthesis.

[@garycard1456]

Suggestion: the lab preparation of dopamine

[@RaExpIn]

It's used as a pharmaceutic compound, which is why it would unfortunately be illegal to do.

[@justinkyledavidson]

Daddy can you do a amino acid decarboxylation with spearmint oil as catalyst?!

[@matthewlayt5194]

*second.

[@nicoenriquelimongecolomer63]

Yay!!!!

[@serg7074]

I think you should explain more about how this chemical could be used. In any way cool video, thanks ^-^

[@နေ့သစ်-ဋ၃ဆ]

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[@RaExpIn]

On the info page of this channel you can find my mail adress. :)

[@နေ့သစ်-ဋ၃ဆ]

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[@နေ့သစ်-ဋ၃ဆ]

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