Make Formic Acid

In this video we make formic acid from oxalic acid and glycerol.
First we combine 100g of glycerol with 100g of oxalic acid in an Erlenmeyer. A distillation apparatus is assembled around the flask and the mixture is gently heated to 105-120 Celsius. I personally didn't have a thermometer so i simply raised the temperature of the hot plate by about one degree per minute until i saw refluxing in the flask. The flask was then covered in aluminum foil to retain heat and encourage distillation and decomposition. First the distillation slowed (after about 1 hour) and the bubbling eventually slowed (after about 3 hours). The mixture was then cooled an additional 100g of oxalic acid was added. The mixture was then heated again and distilled. This cycle of waiting for the bubbling to subside and then adding more oxalic acid was repeated for 2 additional times for a total of 4 additions (including the initial oxalic acid addition). After the bubbling subsided again 50mL of water was added and the mixture distilled one last time.
Fractional distillation was performed to obtain formic azeotrope at 106-108 degrees Celsius. Total yield was 122g. Assuming the concentration is 77% then the formic acid yield was 94g or about 64% of theoretical.
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[@NurdRage]

Dammit Gary.

[@Uocjat]

Poor Gary :( another victim in the name of science

[@sirflimflam]

Can I have his 20 bucks? I won't jump in and disturb your work.

[@HoverFreddy]

Well,,look at the bright size: With his 20 bucks you can still get some glassware or chemicals xD

[@unpronouncable2442]

that was actually interesting. why would Gary wonder into that vessel? Was it because it was warm? or because it smelled something tasty?

[@adityavarma193]

I mean, chemplayer has killed many ants in the name of science!

[@ytrewq6789]

RIP Gary, you will not be missed at all

[@Biospark88]

Why does formic acid neutralize all other acids? It's the ant-acid. ...I'll show myself out.

[@damonjackson5857]

Biospark88 lol

[@HorkSupreme]

Nice

[@zanpekosak2383]

#punmaster

[@MattExzy]

This comment was ANTagonising.

[@marciaosullivan3200]

I had to re read it as I that wrong

[@squeethesane]

dammit Gary, YOU HAD ONE JOB.

[@UnitSe7en]

Gary's all like "Hey, hold my beer and watch this!"

[@American-Motors-Corporation]

but but but I'm over a minute and a half in and he hasn't crushed our expectations!! lol

[@zoolapin]

RIP the formic acid addict gary

[@jozefnovak7750]

Formic acid? Super! Thank you very much!

[@ryanhester2146]

You're a cool dude. Chemistry is cool, and your videos are well made. Can't believe I haven't subscribed yet, so that's taken care of. Take care.

[@o_-_o]

Glycerol Garry was a good guy actually. R.I.P. GG at Bug's Afterlife!

[@astralchemistry8732]

Interesting approach!

[@goldrecovery]

great video. thanks

[@redytatu2332]

Você é o cara 👏

[@suckinDiesel44]

Good job.

[@sudeepmestry4186]

Thanks for information

[@mauriceupton1474]

Great 👍 channel.

[@cannagorilla]

Hey! There you are. I been looking for Gary for ever. lol

[@EddieMendy]

Gary is my hero :') He didn't sell his soul

[@micah8755]

Dear Dr./Mr. NurdRage, would you consider putting a slide or two at the end of the video showing electron pushing when you do reactions like this? For educational purposes.

[@benearhart1224]

@NurdRage When I did this, I forgot what the temperatures were and I couldn't be bothered looking them back up. So, I just went very careful on the heating. It turns out that if you are very careful on the heating, your glycerine does not darken. Pop a stir bar in there and it looks like any old clear solution

[@LiveForKush]

RIP Gary. Gone but never forgotten.

[@Tgernos]

i'm thinking of suporting you, just subscibed a few weeks ago and i'm just fascinated by your work ( sorry for my english )

[@sletharanamathine]

BTW this Gary bug part was fun you make learning more interesting

[@anjummahmood324]

Thanks

[@t1world767]

Very Nice👍👍👍👍

[@stephenjacks8196]

Saw the same I think on OrgSynth site, glycerol and oxallic acid (plus something, acid?) anyway glyc forms a double ester with oxalic which loses 2 CO2 at once and product is primarily allyl alcohol.

[@martinofgliwice1486]

Is it possible to obtain formic acid while making levulinic acid from saccharose and sulfuric acid?

[@twocvbloke]

Gary: Proof that evolution is about the survival of the smartest... :P

[@kingoffallout3526]

is so cool

[@gmc9753]

Anyone else notice that formic acid = "HOOCH"?

[@BothHands1]

gmc9753 😂 Brilliant

[@benjaminmargulies1853]

added to gin (a type of hooch) to make anty gin

[@PhiloSage]

The bug's name is Bob! Which is why he was confused and took a dip when you called him Gary.

[@himanshu2232]

Sir what should take precautions in reaction between Formic acid and H202 ??

[@ThisMoose]

There's a much easier way to do this. Step 1: Put a whole bunch of ants in a juicer. That's it.

[@MuzikBike]

2. Deal with PETA.

[@festerallday]

Yes fireants suck. So would this stuff feel like getting stung by a 50 pound ant?

[@ReallyWemja]

only if you inject it

[@MystycCheez]

If PETA shows up, that confirms they care more about ants than any other animal

[@ReallyWemja]

+jakob its not only in the ants themselves, it is also secreted into the anthill to keep it clean. They used to dig up the whole anthill and distill the soil & ants. but indeed you would not get a lot of acid from an anthill, its likely that it was a very low purity.

[@sletharanamathine]

I am Here to learn

[@mauriceupton1474]

Can formic acid be dissolved in glycerin Like oxalic acid can be or will it react to form some thing else. Using it to kill varroa mites in bee hives.

[@nickoolay]

Nice video

[@NurdRage]

why thank you!

[@ariel_haymarket]

RIP Gary, 2017-2017

[@user-is9tg1vb5m]

are you the additions oxalic acid 100gr as 25 gr and 25 gr ...? or the summation 400gr .thank-you.

[@alexschmidig4332]

love those bugs

[@Archiekunst]

I saw the bug right at 2:09 . Can anyone suggest what made it jump in like that? One of the chemicals must have acted as a chemoattractant. Does the ester smell fruity?

[@pietrotettamanti7239]

Archishman Ghosh maybe it eats ants. Such smell of formic acid probably meant a party to him.

[@shrimpfry880]

something that videos never mention is that concentrated formic acid smells horrible. i handled it just like in the big book (with gloves) but once i opened the cap i felt a strong, sour pain in my nose and sinuses.

[@FamAccNr1]

oh god i thought this gonna be an april fools prank and you would crush ants... thank god

[@jonnathanschillinger9021]

What stops the glycerol backbone from being tri-esterified? Why won't oxalic acid or formic acid in the reaction mixture continue making esters on the other two hydroxyl groups? Is it purely steric hindrances?

[@jakob1410]

I'm sure it will form esters on all hydroxyl groups. When the concentration of glycerol is very high formic acid is more likely to "find" non substituted and mono esterfied glycerols than di esterfied ones. So a statistics/concentrations thing. Sterics are likely not a problem, as many fatty acids have a similar structure with bigger substituents. This will still lead to the same results/product after hydrolysis, theoretically needing less catalyst but due to decomposition the reaction was run with excess.

[@pietrotettamanti7239]

Stoichiometry

[@Carl-nf9bf]

RIP Garry. you will be remembered.

[@adityavarma193]

distilling ants?? maybe chemplayer can use some of his ants for this purpose!

[@swinfi2]

rip chemplayer('s channel).

[@RelianceIndustriesLtd]

I think the bug was somehow attracted to the smell of the chemicals

[@vshanmughamvshanmugham599]

Good@

[@2001pulsar]

Can I use just sodium formate to reduce palladium from HCl and HNO3 solution, or can i use the sodium formate to make formic acid? Thanks

[@2001pulsar]

Also, is vegetable glycerine from the vape shop ok to use?

[@ThePeterDislikeShow]

Can you make formic acid with carbon monoxide and water?

[@kelvinn7395]

2:04 The random mutant fly was returned

[@JehuMcSpooran]

I've read somewhere that electrolysis of glycerol produces formic acid as a byproduct. Would it be better to go down that route and not waste oxalic acid?

[@camurgo]

Oxalic acid isn't that expensive either. I read a paper on making the reaction you mention, it seems more difficult to achieve without high quality equipment.

[@chrisluckas7521]

R.I.P Gary.

[@garycard1456]

I prefer the Soxhlet extraction method, in which I fill the thimble of the extractor with ants. Do you think water would be the most effective extraction solvent in this instance?

[@petevenuti7355]

I've heard ant brain has 100x more cells for the same volume, and 1000x more connections... (So 100,000x more bits of info?) I have also heard of a lawyer that had untreated childhood encephalitis and after getting a PET scan as an adult, only 1cm³ of their cerebrum was alive!! Does that make ants somewhat equivalent to lawyers? All the more reason to boil them in a extractor..

[@Harufloof]

gary is my idol

[@TG-M-gu3lk]

Is it theoretically possible to decompose the oxalic acid into the CO2 and formic acid?

[@michaelsambor5286]

"it will mostly sublime and decompose"

[@Alex-ee5pl]

So what's the advantage of doing it this way as opposed to just oxidizing the hell out of methanol and distilling?

[@NurdRage]

This one actually works

[@santiagomuller852]

Could be possible to see a Biodiesel make and purify Guide?

[@elephystry]

Bug Hunter just decompose triglycerides with (m)ethanol and then you'll have (m)ethyl esters (biodiesel) and glycerol.

[@santiagomuller852]

Thanks, I know how it works, but I think a guide at chemistry and amateur level could be awesome to see. Almost every of the experiments here require some pricy equipment and knowledge and are far away of the amateur chemist, maybe this could help in that matter :D

[@Spycyzygy]

Bug Hunter check out Nile Red's channel He removed glycerine from vegetable oil Also ChemPlayer made biodiesel from the same process and even tested its flash point cofirming it's potential use as fuel

[@Masterpg2007]

I was studying this 1 hour ago.

[@grafotec]

could you make allyl alchool video ?

[@tempstation810]

I know what I'm doing today!

[@kemjoel9522]

Can you do this with ethylene glycol instead of glycerine

[@NurdRage]

in theory it should work. I haven't tried it myself but i don't immediately see a problem.

[@MoleculedMan]

RIP Gary

[@adamparkes6609]

Please make some quality 4-MMC England needs some

[@garrettlines6628]

Great tutorial. But why did you pour the distant back in at timestamp 4:51?

[@negavite_major]

The distillate was contaminated by a bug which is why NurdRage had to pour it out. The bug would have likely affected the distillate's purity

[@garrettlines6628]

But it wasn't the stuff he wanted the keep.

[@jtbmetaldesigns]

The comments are as entertaining as the chemistry here

[@illustriouschin]

RIP Gary.

[@nunyabisnass1141]

Rip Gary. November 2016 - March 2017.

[@comando1911]

Formic acid. Now I can simulate an ant bite!

[@danielf.7151]

Question: what does the QR-code in the credits do?

[@duffman7674]

Looks like it's an address for bitcoin donations.

[@JasuTheSnipe]

the code reads 1NurdRAge7PNR4ULrbrpcYvc9RC4LDp9ps and it's to donate via bitcoin

[@wmonger]

Daniel F. Takes you to a Bitcoin address

[@danielf.7151]

Thanks.

[@gumball1000000]

Liking for Gary

[@priyanktechz1829]

Ikw a Better way - distillation of ants 😋

[@JGHFunRun]

To avenge you against bugs I will acquire my formic acid from the OG source: distillation of ants

[@tempstation810]

Shit, I'm getting so much refluxing that the water from the initial oxalic acid is being driven off incredibly slowly. I'm worried that the mixture is decomposing since I can't get the water to distill over without raising the heat. My flask neck/still head is too long and no matter how much I insulate it I can't keep the water from condensing in the column before reaching the condenser. I have a weird glass distillation setup I got years ago from United Nuclear. I may have to scrap ths completely and try again when I can get a proper glass distillation set with a shorter path for the vapors. I have only collected a small amount of liquid however the temp in the still head hasn't risen above 95C and it had been stuck at around 53C and 88C for a while at a few points in the distillation. Not looking good, I don't want to potentially form anymore toxic decomposition products.

[@camurgo]

So, did you get around doing it properly?

[@AhmedAhmed-fh2ce]

Your number bro

[@werdna3194]

the part about gary made me laugh so much¡

[@garycazzell4547]

You named him what, now?

[@rustyshackleford1964]

CAN YOU MAKE A VIDEO ON ELECTRO PLATING? IT'S A CHEAP EXPERIMENT AND PEOPLE COULD REALLY BENEFIT FROM IT

[@cr0ss0ut]

he already made an amazing video on making your own cheap Platinum electrodes!

[@abhigyananand2435]

Sir I want to know how can I convert 45% formic acid to 85% formic acid

[@AhmedAhmed-fh2ce]

Your number please send me your number and help u.

[@stephenjacks8196]

"Oxalic acid is just carbonic acid with carbon monoxide." Org Synth has a synthesis of allyl alcohol by distilling glycerol plus oxalic acid via oxalic 1,2 glycerol ester.

[@mduvigneaud]

Just to be completely stupid: is this what Ender used to defeat the buggers? :)

[@ethanthompson431]

wow im early

[@seanconfer7903]

Freaking Gary!

[@Daniel92mo]

How To Make 0.1M HCOOH using 0.1M H2SO4?

[@therealquade]

a video about formic acid, with a bug. Who knew?

[@eier3252]

make formic acid using ants, and a bug as catalyst

[@emilalmberg1096]

Formic Acid common name in Swedish is Ant-Acid...

[@ZloiPiroman]

Bug Gary))))))

[@didaloca]

Add some to a tattooist's ink, lol.

[@apburner1]

Wouldn't formaldehyde with a basic catalyst reaction make more sense if you want formic acid?

[@blackwingmaster141]

This is OTC/amateur procedure. Formaldehyde is not so easy to obtain

[@lheofacker]

I added water to the acid and my house exploded (along with a little bit of the neighbor's), what do i do now???

[@kahlzun]

Call Statefarm?

[@thatpersonyouknow3747]

because they seen it all

[@Shepard_AU]

Blame it on Gary

[@GodlikeIridium]

roflmao the bug xD

[@procactus9109]

Suck it, Gary. Suck it, Gary. Suck it, Gary.

[@Brianramos993]

Rip Gary l

[@robertheal5137]

Can you distill ants ?

[@sletharanamathine]

can I make a hydrochloride acid out of oxalic acid

[@tilobidaLP]

no, it doesnt have any chlorine in it

[@sletharanamathine]

I don't know like adding it in an other mitral you know ps ( I have no much chemical vocabulary )-sorry if you didn't understand-

[@sletharanamathine]

Tilobida thx BTW I need a professional in this ( NurdRage)

[@DagasNeedle]

Slendaguy no, you cannot make a stronger acid from a weaker one, and Formic Acid is a weaker acid than Hydrochloric Acid

[@sletharanamathine]

DagasNeedle oooh ok guess I should ask my chemist porf

[@science_and_anonymous]

how much you wana bet he plays a big chemplayer on us and makes carbon monoxide from the dehydration of formic acid via sulfuric acid

[@fizixx]

😄 Gary

[@abhigyananand2435]

Can you upload on this video

[@DevinHeaps]

Is it true that chemists originally used ants to make formic acid? If so, how did they do it?

[@blackwingmaster141]

Litteraly, put ants in flask and distill them. Cruel, but that's how acid got it's name

[@suckinDiesel44]

Fucked a ton of ants in a distillation flask and distilled them, no joke.

[@Eric_Pham]

Nikola Jambrović cruel but they out number us a billion to one I think their fine

[@polyjohn3425]

I wouldn't call it cruel, ants are literally incapable of sensing "pain" as we understand it. They don't even have real brains, just ganglia.

[@chemiosmoticphosphorylatio3198]

ask chemplayer why they have ants everywhere in their lab :)

[@sudeepmestry4186]

There is also simpler way by mixing C12H11022+HNO3

[@NurdRage]

good luck trying to get reproducible yield from that. It's not simpler at all.

[@ironmonkey1512]

Probably easier to do something with bleach and windshield wiper fluid