Making oxalic acid from cane sugar

Here we do a scaled up version of the oxalic acid synthesis that ChemPlayer did. The table sugar (sucrose) is oxidized using nitric acid.
This is a pretty dirty reaction and it is not very efficient. Oxalic acid has various uses, but I want to use it to make oxalyl chloride, which will in turn be used to make TCPO which is used in glow stick.
The followup video to this one would be the azeotropic distillation of oxalic acid to dry it. In order to make oxalyl chloride, we need very dry oxalic acid ( • Making Anhydrous Oxali... )
ChemPlayer video - • Video
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Nile talks about lab safety: • Chemistry is dangerous.

[@100610victor]

I'm a tankerman and I'm very glad I found your videos I work with chemicals in a large amounts (55k barrels) so these videos are awesome

[@stonent]

I would be interested in a Nile Red, or Nile Blue video on how and why certain chemicals put a taste in your mouth when they contact your skin. I remember that happening a lot as a kid with a chemistry set.

[@Tommo.]

tf

[@EddieTheH]

​@chu Harry DMSO

[@kangalow]

@@EddieTheH can I ask about your username?

[@steammachine3061]

The plant arum maculatum (better known as lords and ladies) has a large quantity of oxalic acid in it. And is a very common plant in both the uk and the us. Sorrel contains trace amounts also. As a keen forager i wouldnt mind seeing more tutorials on how to extract compounds from readily avalable and abundant wild plants. It would certainly help keep the costs down as picking wild plants is free lol

[@gamingmarcus]

NO2 looks so beautiful. Too bad it's so toxic.

[@gamingmarcus]

I know, I'm a chemist ;) In the big volume that is produced by this reaction it really does look cool. In smaller quanitites it's not that exciting that's true. But it has something to it when it covers your entire fume hood.

[@jamez6398]

P@r@m3d!© It looks cool but I mean the experiment looks more cool than the actual gas itself :/ But yeah I guess it's pretty cool when your fume hood fills up with it.

[@qazsertyer]

Some months ago this happened where I live images.ara.cat/2015/02/12/societat/toxic-dIgualada-carrer-VICENC-SUGRANYES_1302479892_18874457_766x565.jpg . It's NO2, that's what happens when someone messes up with the pipes and put nitric acid in a formic acid container, it's an interesting view. Luckily noone was seriously injured.

[@gamingmarcus]

MarcCG wow I definitely wouldn't want THAT to happen. That looks really bad.

[@qazsertyer]

P@r@m3d!© As I said no one was seriously injured so don't worry, I just remembered it and thought it was interesting to share! It's more irritating than toxic and the meteorological conditions helped to maintain the cloud up. If you are curious there are some more photos here( although is not in english). www.ara.cat/societat/nuvol-toxic-dIgualada-imatges_5_1302519738.html

[@nikonyrh]

This channel is superb! The content is very professional yet casual, and very easy to approach. I hate to say it is perfect but keep hoovering on that :)

[@jakewaitze5104]

Finally I have located your profile picture @NileRed ! 2:44

[@nemeanlyan7918]

As always love the vids! Can't wait to see the TCPO!

[@Beirdo1]

Any chance you'd show us how to extract oxalic acid from rhubarb leaves?

[@stanalbatross8615]

Take a soxhlett, put in your rhubarb leaves, take water as a solvent and let the extraction run for a couple of hours. Boil of the createt solution, maybe wash it with ether (or a similar polar solvent,). The oxalic acit shouldn't solve very well in organic solvents. If it's to dirty you can rekristallise it out of water. Aceton could work as well

[@yukiyuki7761]

how should i know what the right reagents that should be used in extracting oxalic acid? in the video he uses nitric acid, is it ok if i also use nitric acid for extracting oxalic acid from a fruit?

[@AguaFluorida]

Yuki Yuki - no, that would be a waste of nitric acid.

[@CoolKoon]

@@yukiyuki7761 No, the nitric acid's used for breaking down the precursor molecule (sucrose), NOT as a solvent! Also if you don't know what "organic solvents" are, then you really shouldn't be extracting oxalic acid from anything at all.

[@YouMockMe]

@@stanalbatross8615 Thanks!

[@loganplumlee3840]

could you possibly capture the NO2 and bubble it through distilled water to regain at least some of the nitric acid you used?

[@marc-andreservant201]

This is actually pretty close to the reaction used in industry to manufacture oxalic acid. Instead of using just nitric acid, a mixture of sulfuric and nitric is used. Vanadium pentoxide is usually added as a catalyst. Other (read: cheaper) carbohydrates can be used, like sawdust or molasses. The loss of yield is outweighed by using what is basically waste biomass as the starting material.

[@196Stefan2]

I am amazed that this method for the preparation of oxalic acid works (I well know it does), when you consider how easy oxalic acid is subjected to oxydation. It is a quite strong reducing agent and used as a primary standard for redox-titrations with Permanganate.

[@EMandMORE]

your videos are awesome, keep up the good work

[@nicholi8933]

That was neat, keep up the good work.

[@alexisweng]

What molarity of NaOH would be needed to titrate this precipitate?

[@kjpmi]

Looking forward to the Lithium Peroxide and, of course, methylamine (some day) and a Q&A video!

[@JustinKoenigSilica]

I used it to get rid of mno2 and kmno4 from a dirty old reaction flask. Nice.

[@bludeat7398]

how about oxalic acid from ethylene glycol? is hydrogen peroxide good enought oxidizing agent?

[@kumarkishan5156]

Nilered back in these days... Sounded more like a serious chemist.... And as the time flew... He now sounds more like a mad scientist.. 😂😂

[@creativity5187]

If you used a catalyst such as V2O5, will the reaction be more efficient and cost effective?

[@jamescutting1317]

Could the oxalic acid product be crystallized from the waste leftover from the washing steps to increase yield?

[@daltonsoutherland8836]

Loved seeing the difference in packaging for regular stuff like sugar from Canada to the U.S

[@chemistryofquestionablequa6252]

Especially with stuff like milk. When my wife first visited Canada she was a little confused about milk in bags. Lol

[@hamptoncopeland3616]

Hey Nile. Just a thought. would it of been better to wash the acid with diethyl ether due to its low solubility at 14g/L?

[@malinikhanna5100]

while heating the beaker containing sugar so strongly, Is there any chance of occurence of cracking of the beaker or any other damage to d glassware??

[@TazPessle]

Is the loss with the washings enough to warrant a second crop? ..you could keep it separate if it's deemed significantly less pure.

[@gloriousg]

im just wondering how can you extract oxalic acid from rhubarb leaves if you were to do so?

[@lamamriaissa1165]

what is the product reshlte when using the NaClO and sugare (the reaction starte heating after few minutes)

[@pokegal-ew8dh]

Ooo I'd love to see the "converting Aspirin to Tylenol" video!

[@tranquilise8992]

What are the other ways to synthesize oxalic acid?

[@bobthornton8282]

Would making Cyanuric Chloride be a cheaper route than PCl5 to turn oxalic acid into oxalyl chloride?

[@rbtmdl]

Can you extract it from sheep sorrel, rhubarb, or curly dock?

[@Oskar-zt9dc]

nice clean and white

[@spfjpm]

I'm new at this, but what kind of setup is all of that, and what components do I need to make this, and where do I get it?

[@frankobacic8396]

Nice video, keep up the good work

[@5roundsrapid263]

So sugar comes in plastic containers in Canada? It also seems to be 4 pounds (1.8 kg) per package like in the US.

[@prajwol_poudel]

could you use potassium permanganate as the oxidizing agent to make the oxalic acid?

[@worldrc51]

Commercial Lightsticks were never produced using TCPO (not strong enough). They were always made using CPPO... bis 2,4,5-trichloro-6-carbopentoxyphenyl) oxalate. The starting material for CPPO (trichlorosalicylic acid...TCSA), is rather daunting to make (adding that 3rd chlorine)...It would a great project if you wanted to take those two on sometime. Nice KZbin channel!

[@chromecrescent]

How can you be sure of it's purity? There are lots of other products

[@captinccat7766]

I think it would be neat if you tried to extract it from rhubarb leafs, for the heck of it, I love the videos where you" synthesize" (I think I'm using the right word, I'm a bit tired) but extractions just pose a different interesting twist to obtaining your product (depending on how hard it is to extract

[@zenziah]

when I boil the solution , its get black, any guess what's happening? I repeated thrice still black and gui

[@nivmoshe5536]

Can oxalic acid also reduce chloroauric acid to form gold?

[@organicchemistry6357]

Is there than an apolar solvent? If so let me know why you didn't use that

[@mrchangcooler]

Could you use a cheaper oxidizer like Hydrogen peroxide?

[@Zebre86Cie]

Could it have been washed with a less soluble solvant than water?

[@nicolecasal31]

Can this oxalic acid be used to remove metal corrosion?

[@777swampie]

Why isn't the NO2 re-dissolved in water to recover some of the nitric acid???

[@StefanReich]

Did you filter out the side products at any point?

[@stonegolem2001]

so could i get Oxalic acid from Rhubarb leaves?

[@michaelsemerestockmaier9911]

THANX BRO

[@dots5641]

Could you have captured the NO2 into some water and get some (or most) of the nitric acid back?

[@zommbiec7593]

that's a really good question. it probably would work and probably better in peroxide.

[@NileRed]

In theory it could be converted back, but I dont think the yield would be super worth it.

[@jamie91995]

+Nile Red where can you get cheap glassware, I am tired of science websites that over price their glassware and most eBay, ali express, and Amazon sellers have their stuff over priced or damaged.

[@dots5641]

+The Chemistry Kid a lot of times things like glass equipment are expensive because of the processing of the glass and making it harder to crack when heated. I don't actually know of cheap glass equipment but be careful because cheap may mean that it won't last long or even fail in the middle of an experiment (which isn't ideal)

[@jamie91995]

+Dan Swoboda I meant glassware that is good quality, but a cheaper price as well like used glassware in good condition.

[@computerguy1372]

Hey nile! Do you know how to separate a racimic compound into its D and L isomers using tartaric acid?

[@Quintinohthree]

If the chiral compound is an amine or other base, you can simply react it with, for instance, D-tartaric acid to form a DD-salt and a DL-salt with different properties, most useful being solubility.

[@genericaprints8057]

Hey Nile, do you have any tips and tricks on cleaning fritted disks? Maybe you could do a simple video on how you can clean various gunk out of various glassware, etc. I always feel like i'm needlessly toiling away trying to clean round bottom flasks, just to find residue still in them either way.

[@K0ester]

I understand you comment is 5 years old, but when i have stuck residue in a rbf i put a bunch of ice cream salt and a corresponding solvent for whatever residue is in there, and i swirl snd shake it around. Works pretty good, also a baby bottle cleaner brush works good

[@komitaskomitaskomitas]

He has videos on cleaning glassware on his nileblue channel

[@Madarpok]

Given how messy the reaction is, how do you know your product is pure? TLC or melting point would be nice Also any chance you could use a different oxidation method? Maybe ozone or acid + manganese dioxide could do the trick. Or possibly electrolysis?

[@NileRed]

that is a good point. It isnt going to be SUPER pure, but decent enough. It could have been recrystallized. The reaction is messy, but the main product is oxalic acid. I should have done a melting point considering i bought an apparatus a few weeks ago...

[@wtfwtf7965]

what happens when you drink a little bit of it ?

[@nadiakassimi7042]

Can you synthitis formaldéhyde from oxalic acid

[@clausian-ingenuity]

Would aqua regia work as well?

[@MrCoca1404]

i dont understand how did you separate the oxalic acid from the other oxydation products ?

[@masacatior]

Maybe the differences in solubility

[@honheilee1284]

Can you try to wash the product with diethyl ether or hexane to get rid of the organic impurities? Or try DCM, Chloroform, ethyl acetate or THF? I think most of the organic acids are not pretty soluble in those kind of solvents while the organic impurities are quite soluble. I will probably triturate the crude product with one of those solvent and then recrystallise in methanol/ether or methanol/hexane system. Hopefully will get a very pure product.

[@muneebh243]

where did the side products go?

[@andresocampo3548]

what temperature did you use?

[@StefanGliga48]

I remember NurdRage also made glow stick chemical in one of his videos

[@eier3252]

You could do this in a flask and direct the NO2 gas into distilled water to recycle it back to (albeit dilute) nitric acid.

[@itzmealex5325]

3:15 what If I do this reaction outside. then what?

[@batenkait0s657]

what process would be used to make hydrochloric sulfuric nitric ect. acids using oxalic acid?

[@mnemonic5819]

No

[@evileye17]

I've a query... Whether the crystalline form of acids show acidic nature? Actually I am asking this question because I was taught in school that acids show their acidic nature in water but here it is not made dissolve in water and it exists in crystalline form, so will this oxalic acid show acidic nature?

[@avion3033]

Hey, Nile, im not exactly sure on what it is, but you should try making caffeine again but using coffee crystals. Not sure how that would work, but it might be a better yield, as 1 can of the stuff is like 180 cups of coffee.

[@NileRed]

I have never heard of coffee crystals before

[@avion3033]

Nile Red www.folgerscoffee.com/coffees/classic-roast-instant-coffee :)

[@S-K.]

It's also known as instant coffee, it's crystallized coffee that dissolves in hot water to make coffee without any beans/filtering.

[@avion3033]

***** Exactly! That's what i meant.

[@hamoudi_d]

hey could you have recovered some from the water washings?

[@davidmolnar1072]

Im not sure, but a recrystallization would probably do the trick.

[@magnuswootton6181]

the easy way to affect the negative portion of the ionic bond is via cooking it!!! but it gets fumes everywhere and its totally noxious.

[@jclowe735]

Ok if oxalic acid is soluble in water then why not use ethanol?

[@TheJvlustosa]

Why dont you write the equations for the reactions on the video?

[@Arkie80]

Tonight on Nile Red: Making a sorcerer's potion.

[@philippkollenz6565]

is the no3- ion involved in the reaction or could you also just use an equivalent amount of conc. sulphuric / hydrochloric acid?

[@llizardcz6230]

Nitric acid works as an oxidizing agent so no you can't.

[@Ulim151]

Suphuric acid is a stroner oxidizer than nitric acid

[@Quintinohthree]

+Ulim151 It's not, not at all.

[@Quintinohthree]

+James Oldfield There are no ester bonds, only acetal bonds connecting monosacharides, and going from sugar to vsrbon is not oxidation or reduction.

[@Quintinohthree]

+James Oldfield Sugar and carbon have the same oxidation state, 0, when oxalic acid has an oxidation state of 3. You need an oxidizing agent and only nitric acid will work.

[@TSorovanMHael]

Some research indicates that using a modest amount of Vanadium Penoxide as a catalyst can increase the yield.

[@chernoble6095]

Can this be done with potato peel?

[@Cristi0986]

but to convert white phosfor to red phosfor?

[@TWBIAP]

i can think of much more fun things to do with sugar and nitric acid.

[@billsmathers7787]

How are you going to form the acid chloride of oxalic acid? I can't think of any OTC chlorinator that would work other than phosphorus pentachloride, and that's awful to work with.

[@FamAccNr1]

PCl3 PCl5 or SOCl2 maybe. or phosgen?

[@NileRed]

PCl5 is the answer :(. Preparing that will definitely be fun

[@billsmathers7787]

Maybe you could use oxalyl bromide instead? Preparing that by phosphorus tribromide should be a ton easier than making phosphorus chlorides (chlorine is awful, and white phos is worse), and it should still work for making TCPO. Also, if all you want is phosphorus pentachloride, why do you need to convert the red P to white P? I was under the impression that PCl5 could be made by combination of the elements, but PCl3 in the home setting required white P to reduce the excess pentachloride formed.

[@Stormrunner0002]

Have you tried melting stone yet. oxalic, acetic, citric acids. It is said the combination can disolve stone and metal but is safe to handle with your hand and leather boots. It was originally found in a jungle plant in South America. birds used the leaves to carve holes in the stone cliffs for nesting. it also ate the spurrs off the explorers boots when they were trying to find the plant. At first the couldn't find it but they lost the metal from their boot, so they knew they had at least passed through it and it was not a hoax. I am not sure if it is the same composition but INCO uses a chemical smelting process to extract metals from granite by melting the raw material and solidifiing the seperate components. Almost magic to watch.

[@pirobot668beta]

A type of geopolymer: non-carbon polymers of silicate and almuminate groups, at least if you're using alkali process! Acid process acts on the grain-bounderies of stone, softening it enough to work by hand. Exposure to CO2 from the air hardens the stuff over time. Egyptians grew enormous fields of rushes, relative to the North American cat-tails. They grew rushes, burned them and collected the ashes. Potassium and sodium carbonate mixture, quite basic. Additional work make the hydroxides of the salts; lye and potash. Take your stone, pulverize it a bit, and steep in the caustic lye solution. The silicate and aluminate groups are torn apart by the solution at first, making a putty-like substance that is a mixture of Si and Al monomers. The monomers link up to form polymer groups, typically flat hexagonal structures. The flats stack up to form crystals with 'holes' in them. The center of the hexagonal cores is empty, so it lets some molecules through based on size or electrical charge. A geologist would call this crystal a Zeolite, a scientist would call it a molecular sieve, the workers at Ghiza called it mud and packed it into molds to make the big blocks. This is why the massive stones fit together so well; they were cast in place! Fluids move to fill their surroundings, putty under pressure does the same thing.

[@Spycyzygy]

Would ethylene glycol from antifreeze and oxidizing with potassium permanganate work?

[@Aviator747a]

This would be exothermic and just burn.

[@hlakanipetros6670]

if you dilute the antifreeze and acidic potassium permanganate soln.... u could make it... problem is the separation of Mn ions and oxalic acid

[@Spycyzygy]

looks like it's time to hit the lab :3

[@avrorik369]

You can use a mixture of nitric and sulfuric acids to oxidize ethylene glycol. Important: ONLY use dilute acids (30-38%). If you use concentrated acids, you will make EGDN, which is a powerful touchy explosive, a nitroglycerin analogue.

[@NvrchFotia]

Where did you get your red phosphorus?

[@assbutter7627]

Isn't that the acid that is in monstera fruit?

[@DirectorAntify]

What if you used sucralose (Splenda)?

[@glass4600]

honestly me being the chemist I am (not really)... I think it would be different, he used moderately real sugar while splenda and sucralose are "fake sugar". now I may be wrong but with given facts I may be right... do a little research man

[@Madarpok]

While sucralose has similar structure, it also have a couple chlorine atoms, so you would probably get some gross mixture of chlorinated oxidation products. Also sugar is cheaper, so really no reason to use it.

[@DirectorAntify]

+Madarpok I'm actually curious because of the chlorine atoms in it

[@Madarpok]

No idea what it would do. If you can, do it, then separate all products via column chromatography, and send some samples to NMR as well if you can :)

[@sciencepower608]

Please do a video on that glow stick juice so I can make it.

[@Quintinohthree]

That's what this was for. Preparation for that video.

[@NileRed]

it will get there eventually. Not exactly the easiest and safest procedure though

[@qazsertyer]

Hahaha yeah, someone has to be crazy to try to make azidoazide azide.

[@flurgy22]

+MarcCG azidoazide azide is like sodium azide's unstable uncle that blows up over nothing at all. just thinking about it makes it explode.

[@rakinkazi9780]

nurdrage made a video about it tho

[@Belasrimohamed]

How to make sulfamic acid

[@shreyashah9598]

Could you have done another recrystallization to ensure purity of the oxalic acid crystal?

[@adrianpisiuta6472]

You can recrystallize it as much as you want but keep in mind that you will always lose a little bit of your product

[@shreyashah9598]

@@adrianpisiuta6472 Thank you!

[@adrianpisiuta6472]

@@shreyashah9598 you are welcome

[@akhilthechemist]

whenever i carry out this reaction after the reaction my solution turns black .why ??

[@SuperAngelofglory]

probably you heated a bit too much and some sugar decomposed to carbon and water

[@dascandy]

Or it's insufficiently acidic and you created caramel instead.

[@Ravtank1]

Have you ever considered trying to extract oxalic acid from plant such as parsley, chives, amarnth, purslane or cassava? Parsley being the higher in concentration would be the best possible.

[@breloom8448]

sawdust is really easy source of oxalic acid

[@AureaPersona]

oxalic acid is very useful, it can for example be used to make formic acid and to purify rare earths as many of their oxalate salts are very insoluble and stable.

[@Patrick999102]

One book I have,describes the preparation of oxalic acid from wood chips: those are heated in strong solution of KOH. Cellulose is said to dissolve,forming HCOOK at first,but upon continiued heating,potassium oxalate. further,oxalate is just percipitated as calcium salt,reacted with HCl to give the acid and cooled,to make it crystalise.. So does that basically mean,that potassium formate,upon heating,sort of reacts with itself to make oxalate?( it is said here,that two molecules of formate combine,to give one molecule of oxalate). Asking,because I haven't seen any oxalic acid being sold around,but local hardware store sells 85 % formic acid.. was wondering if I could make it this way.. Another idea was to isolate it from rhurhab leaves,but I guess that's just too inefficient and complicated..

[@FamAccNr1]

the sodium formate is reakting with "itself" to form the sodium oxalic acid. thats what they do in the industry. at around 360°C, not sure if under pressure.

[@zanpekosak2383]

Does the NO2 stain stuff? (labcoats,skin,...)

[@firehoax9230]

BeGamerSl no, not really, its a gas and doesent bleach either

[@zanpekosak2383]

Firehoax Thanks!

[@sacsy2011]

What's the name of your magnet thingy that mix things up?

[@thewuurm]

Magnetic stir bar.

[@FamAccNr1]

or the magnetic stir plate

[@najamsehar9122]

how to prepare derivatives of oxalic acid ?

[@Aichybatoal]

I know you can get simple oxalate salts by reacting oxalic acid with alkali hydroxides. For example, C2H2O4 + 2 KOH -> K2C2O4 + 2 H2O , then you'd have to evaporate the solution to retrieve your potassium oxalate (with small amounts of KOH or oxalic acid impurities, depending on which one was in slight excess). That's all I know, sorry...

[@getmeoutofsanfrancisco9917]

I remember when some people died due to bad Chinese vape juice due to the presence of Ethylene Glycol as opposed to the usual Propylene Glycol which is used as the carrier solvent for nicotine.

[@agazaman]

can u make graphene from sugar

[@firefrog101]

it wouldn't be conventionally possible because saccarides consist of a lot of oxygen and hydrogen. Graphene is a sheet of virtually pure carbon, continuing as a a tessellation of hexagons; having a different motif that sucrose. The first step would be isolating carbon from sugar. and having oxygen makes that a problem since it is electronegative, and then removing the hydrogen some how, so that you have pure carbon.

[@markolazarevic4209]

Can I use other oxidizer, or I must use nitric acid?

[@markolazarevic4209]

Ok thanks.

[@Monothefox]

What happened to the four-carbon compounds?

[@SuperAngelofglory]

I imagine they have higher solubility than oxalic acid and stay in the solution

[@quistan2]

Oxalic acid is tasty. It gives sorrel its sour taste, as well as a number of other edible plants like oxalis.

[@quistan2]

@Oliver Judson It tastes like sour, unless there is something wrong with your taste buds. Its in the same family of acids as vinegar.

[@makeomengreatagain]

Will hydrogen peroxide work?

[@ashercicco9713]

why not make the sucrose

[@zachfernandez1257]

I really appreciate your videos! I didn't get to learn Chemistry in school because my politics didn't agree with the Highschool I attended. I would love to have a conversation with you sometime. keep up your amazing work! you may change the world some day. people are listening to you weather it be for their own introductory labritory studies or someone like me who is interested but never got the opportunity. You are changing lives and people's minds. keep up the good work!

[@yakacm]

I hope I don't sound rude, but you did get the opportunity you just chose not to take it because your 'politics' didn't agree with your school whatever that means. Without elaboration on how the schools political stance interfered with your education, it just sounds like some bullshit excuse for why you didn't do well at school, like it wasn't my fault it was the schools politics man, they let me down. Don't know what country your from but if you are from the US or Europe or some other developed country, we have great educational opportunity that folk from less developed countries would kill for, it's up to us to seize that opportunity with both hands. I did really badly at school and it would be easy for me to say it was the schools fault, they let me down, but it was just because I was a lazy bastard who couldn't be arsed applying myself to my studies simple as that, and like all adults who didn't take the opportunities offered to me I regret it like hell. My school was pretty shitty in a shitty neighbourhood but other kids I went to school with went on to become doctors, senior policeman, lawyers etc, and I am going to bet it's the same with whatever school you went to.

[@Alexanator28]

When you are stating concentrations, why do you use percentage rather than Molarity?

[@NileRed]

For nitric acid? It is just easier because that is what is written on the bottle.

[@Alexanator28]

Oh I see, thanks for your response!