Making Anhydrous Oxalic Acid (using a Dean-Stark Apparatus)

[@PaschalisTsi]

Great vid, as always. Toluene is insoluble in brine so throw some table salt in your cloudy toluene and will become VERY clear again.

[@First6Blood]

Im never gonna try this out but god damn this is relaxing to watch

[@dreamyrhodes]

Oxalic acid can be written as "HOOCCOOH" which looks a little bit like someone sneezing

[@priitmolder6475]

"Is that a train?"

[@beetle6746]

I imagine a science teacher writing that on the board when they asked “Now what is another name of Oxalic acid” and someone just sneezes

[@JGHFunRun]

My attempts to pronounce sounded like an old guy coughing

[@AsymptoteInverse]

The Dean-Stark apparatus is a beautifully elegant device.

[@baberoo3898]

Nile said “a little bit ghetto” for a chemical stirring; spoken like a true scientist!

[@vruatsa]

Wow, can you make one about Methyl Iodide and maybe its safety concerns and recommendations? Great job explaining everything so clear!

[@ChevisPreston]

I just binge watched about 3/4 of your videos. You're doing a hell of a job; I'd be doing more at home synthesis if glassware wasn't so expensive. The chemicals are easier to get, as most things you can extract from common items, or buy it on amazon, for not too much, but, as I lack the proper glassware, I'm stuck doing everything at the lab. Anyways, enjoying your videos. If you want a challenge, try to synthesize nicotine without purchasing methylaminopyridine. Might give your leftover bromine a use contingent upon where you start, and would be a decent challenge. Plus, it'd make a cool trophy jar.

[@NileRed]

+Chevis Preston hey! I looked it up before and i think making nicotine might be a little too hard to do at home

[@ChevisPreston]

+Nile Red it is definitely a challenge. A few biochemists I work with decided they wanted to do a synthesis of it in the lab, and, starting from ground up, some of the reactions produced a pure and quantitative yield, while others made terribly diminished returns, even under lab-grade equipment and tools. Overall it was a lot of fun, and we produced about 82% yield from the base material theoretical, and measured it as about 99.2% pure... Definitely not the 99.9% that you are able to extract directly from tobacco. As some of the alkali drugs are very soluble in any variety of solvents, our last wash took place with water, as nicotine is miscible around 50° with water, while other contaminants got caught in the water. We then chilled it in an ice bath and waited for the clear, oily nicotine to separate from the contaminated water. Definitely a lot of fun, though it was a challenge. Could you do it? No doubt. But it would be a multi step process spanning a few videos.

[@NileRed]

+Chevis Preston Do you know what pathway you followed? The one i see online uses n-BuLi which I do not have and cannot buy. I could make it, but it is pretty dangerous to work with at home

[@AddisonPhilips]

Very Useful, thank you. Could this same idea be used to dry Zinc Chloride? And, you might want to mention to use dry DCM. You know how DCM tends to get a little wet. It would be a shame to put water back in, after working so hard to take it out :-)

[@NileRed]

+AddisonPhilips That is a very good point about the DCM! It didn't even occur to me... I think it is possible to dry zinc chloride like this but i am not 100% sure.

[@Ormodius3751]

if you don't have a dean stark apparatus, you can mix the oxalic and the toluene, and boil it. The toluene and water will boil off, leaving you with water free oxalic acid.

[@MrRishik123]

AHHH I get it. Azeotropes are like alloys of metals but for liquids.

[@zommbiec7593]

exactly

[@MrRishik123]

+zombie apocalypse it's such a satisfying feeling when you finally understand something that bugs you for a week.

[@neovictorius]

+Mr Rishi The Cookie Yeah, but the thing is that an azeottrope is also like a point where you can't get a cleaner product. Like say you distill ethanol a few times and you hit maybe 95 %. Now if you try to distill it again you will still only get 95 %. That's because ethanol and water has an azeotrope at 95 % ethanol - you simply cannot get a cleaner product by ordinary means. In order to break an azeotrope you have to find cunning ways to do so (in the abovementioned example you would use chemical drying with magnesium sulfate or use molecular sieves or something along those lines).

[@MrRishik123]

+neovictorius dony worry bro. I know that. I've been reading up about it a ton and only after his video it all just clicked into place.

[@TheSands1984]

+Mr Rishi The Cookie No, actually, azeotropes are to liquids as eutectics are to metals, sort of. A eutectic is an alloy of metals that melts at a constant temperature.

[@larrylentini5688]

This channel is just chemistry ASMR

[@flaplaya]

Just a couple days ago, the video to some of my dreams was uploaded... Excellent visual and audial description of how this tool works... Studied diagrams and have spent a few hours reading on this apparatus and it never connected.. So the undesired vapor gets trapped in the azeotropic solvent and then condenses back down into the evaporating flask and the desired vapors proceed? Been wondering for years about how that thing works and it's peaked my curiosity lately (coincidentally). It's obviously masters degree level stuff so I think a few more runs are warranted to get us inexperienced up to snuff on the workings. Great video and I'm purely an academic deciding if I want to go full time Chem... Love it love it love it. That's not a job, that's a piece of artwork right there... Absolute Ethanol would be an easy simple legal target and I'm sure it's already done.. Trying to think of other things... 30% H2O2 maybe from 3%... Idk

[@NileRed]

+fla playa The classic way to make absolute ethanol is by azeotropic distillation using benzene or toluene! I wouldnt think it would be useful to make 30% h2o2 though

[@flaplaya]

Ah, so my organic chem skills by instinct are halfway intact at the very least:) Didn't know benzene could be used as an azeotrope..Your skills are pretty amazing and thanks for the correspondence, I'll try to not comment too often. Yeah I suppose H20 and H202 are extremely similar and have nothing to do with separation via this configuration... Thanks. Inspires me to get into classes soon :)

[@NileRed]

fla playa I am glad you enjoy the videos! Yeah h2o and h2o2 are quite different indeed :)

[@flaplaya]

Nile Red Hmm. I thought both H202 and H20 were polar with very similar melting points... Boiling points are way off though.. 302F is way out of bounds so yes I suppose they are very different but still share many properties... Any other differences? A prominent KZbinr made a comment about freeze separation and it doesn't work.. Won't name names but that guy doesn't deserve quite as much attention as he gets.. Too many less than apt people just gobble up crap videos with great editing. I noticed this channel being extremely concise and precise. It and has gotten my nod.

[@drakosmajor]

YOOOO It would be cool to see a return to this but making the oxalic acid from Oxalis (triangularis or another variety) false shamrock! I'm going some and learned their toxic to pets because of the oxalic acid, but also edible for people in relatively small amounts.

[@Dingomush]

At the end, couldn’t you dry the wet powder in a vacuum chamber? Or would the DCM ruin the seals and pump?

[@science_and_anonymous]

or, you can nitrate the toluene and make TNT. Also you used the word "ghetto" in chemistry lol

[@lolnjeoglondajmejejplejlis3365]

He already said he doesnt plan to show explosives on the channel

[@MadScientist267]

Used "nifty" too... 🤷‍♂️🧐

[@damionshort823]

Bro I was waiting for someone to mention this. It literally put me into a laughing fit.

[@giansieger8687]

maybe he could dry his nitric acid using this procedure?🤔

[@billsmathers7787]

How are you planning on making oxalyl chloride? From sulfur chlorides made by bubbling chlorine through sulfur?

[@gamingwarrior2522]

You're a legend

[@bananaman4477]

If you need everything dry, then apply some Flex-tape!

[@Billcipher_fan5]

Im convinced this guy could have or already has created the philosophers Stone

[@RobMakowski]

Would you have any interest in doing a explanation video of how marine aquarium test kits work? The test kits I have are you NH3/NH3, NO2, NO2, alkalinity, calcium, and magnesium. I'm interested in getting a better understanding of the process that produces the color change in the water sample.

[@JayMark2049]

+Rob Makowski Don't you mean ''NH3/NH4, NO2 and NO3''? These are standard water tests. The processes that produce color change are chemical reactions between reactants found on the test kit and the chemical species you are wishing to analyse in the water. The reactions themselves vary depending on the test you are doing and the analytical method. In the case of an indicator such as bromocresol green for instance, the color change is due to changes on the molecular structure on the indicator. In acidic form, it is protonated and has a yellow color. In alkaline conditions, it is deprotonated and has a blue form. In the case of hardness (calcium, magnesium), indicators like eriochrome black react in the presence of calcium/magnesium ions to form a reddish complex. Then, titration is made with EDTA to form an even more stable complex with Ca/Mg and thus, ''depriving'' the indicator from it's complexed ions making it turn blue when no more Ca/Mg is bound to it (equivalence point). These are examples. I don't know what methods are used in your test kit. But it should give you a general idea.

[@PCSoftware]

I love how in half of your vids you say "Honestly, I dont know why this is happening", most often when you see a discoloration. It would be very informative to know what contamination cause those. (This is what NurdRage does better)

[@NileRed]

+Stikmann The biggest issue is that most people dont know. A lot of times it is just a contamination which is characteristic of the way that the chemical is made industrially. Despite a lot of research, you are often unable to find a real reason though. The oxalic acid returned back to pretty much white after cooling down, so i assumed it was because it melted a little. I want to be clear in the video though, that i dont know the reason for sure

[@Bouzsi]

Broooo, yo heating mantle is *THICC*

[@ivantimofeev2233]

oxalic acid is dirty cheap where I live, 8 dollars the kilo, and it is surprisingly pure, goddammit, even the hidroxides are twice as expensive per kilo

[@BalticLab]

Could you use chloroform or other solvents for this?

[@5naxalotl]

neato. i learned that immiscible liquids can form an azeotrope. great apparatus

[@blzt3206]

Oxalix Acid X OFF-WHITE Collab

[@alessandrostagno8070]

Always the best!

[@refluxcatalyst7190]

Graham condenser is a weird choice for this. Why didn't you use an Allin or a Liebig condenser?

[@bharrison4]

Never been on his video this early. (great vid.)

[@bobbyc2768]

cool....it would have been cool to make calcium oxalate which is what kidney/bladder stones are made of

[@rajeshshahi1000]

I am eagerly waiting for the Cu(OH)2 and N2O video.

[@gurt3823]

Can you make a video on how to make tellurium, I need some for my collection and want to try to synthesize it. Thanks!

[@GRBtutorials]

To do that, you need a tellurium compound, then you can manipulate it to make tellurium. You can’t make tellurium without tellurium atoms (unless you happen to have a particle accelerator at home and a few atoms are all you need).

[@caleschley]

Would it also be possible to distill the product desired by performing it in low pressure environment?

[@stefanstark7881]

Couldnt you just use the DCM directly for drying. I mean it forms azeotropes with water too

[@mattbalcerzak]

Round bottom flask had me hallucinating lol i thought i saw two piles of powder inside when the stir bar started, nope just the reflection of the hot plate haha

[@anees5156]

Can you make video on preparation of oxalyl chloride?

[@rangeispow]

Can you make a video about the Ammonium Dichromate volcano reaction? It is really awesome. Maybe you could also use the Chromium III that is produced to make a comparison video of sugar + potassium nitrate vs. chromium III + potassium nitrate, as chromium is a strong oxidizer. Maybe it will burn faster? :D

[@newgrounds90]

+Sam C lol that sam pepper pic

[@EpzilonZ]

when are you going to upload caffeine from energy drink video? you said that you plan to do it

[@KowboyUSA]

You don't have a decent vacuum pump, BUT. you do have a Dean-Stark Apparatus and that's a pretty impressive piece of labware. (Would someone capable please step up and get this man a vacuum pump!)

[@douro20]

If I had the money I'd buy the 3-stage Edwards pump not too far from me and send it his way.

[@KowboyUSA]

douro20 Sounds like you and I are in the same broke boat. One of these hopefully a charitable and capable fan will come along ;-)

[@omsingharjit]

Where is that video ?

[@RedDogForge]

DCM same chemical used to extract caffeine in your other experment ya?

[@Berghiker]

Can you show how to make ANILINE DYE? (PURPLE MAUVE) color.

[@TheSkytherMod]

Shit, I heard "Hey guys" and instantly thought is was going to be "Hey guys, this Austin"

[@texasdeeslinglead2401]

dude I thought you had speech impediment, then I realized it wasn't tolulene, ( BAD spelling , my finger has a typing impediment).😁

[@shrijkumar8704]

while extracting caffeine from tea can we use anything except For chloro methane?

[@chemplay1799]

Nice stuff here :) Did you study chemistry or are you just very curious about all this ? ^^

[@NileRed]

+Chemplay 17 I did study chemistry but the curiosity grew on its own :)

[@chemplay1799]

+Nile Red may I ask what you do now with your degree or rather what part of chemistry you work with ^^

[@douro20]

Did you buy that on Aliexpress? It seems to be a good place to find good cheap lab glassware.

[@theginginator1488]

Can you do a video on making oxalic acid?

[@NileRed]

+TheGinginator14 Sure, I plan to eventually

[@timroberts9254]

+Nile Red would you be able to do a video of how to extract pure ethanol from E85 fuel?

[@kevincolwell2115]

Would it be accurate to describe an azeotrope as a liquid counterpart to a eutectic?

[@zanpekosak2383]

Sure

[@SebastianoZanda]

Yes if you only compare it with the negative azeotrope

[@TheAxecutioner]

Watching this just to see the Dean-Stark in action xD

[@jakobliggett3018]

Where'd you get all your glassware from?

[@pvc988]

You are making 3CPO? Sounds good.

[@JennyEverywhere]

+pvc988 Is it bad that I read that as C-3PO at first glance? Oh, noes! Nile Red is ANAKIN SKYWALKER!

[@pvc988]

+Gwen Patton NOOOOO!!! NOOO!!!

[@JennyEverywhere]

That's not true! That's impossible!

[@stevenswenson7041]

+Gwen Patton Isn't that Luke's line to Darth?

[@spaceyboi6651]

I remember using this apparatus in my lab class to estimate how much water is in sausages :p

[@spaceyboi6651]

+Alice Bonnet Oh I dont remember... but it was ok with the norms

[@spaceyboi6651]

+Alice Bonnet Companies add water as a filler so if theres too much of it the sausage is spongy and low quality

[@rajeshshahi1000]

It has been so long you haven't done the element series please do it.

[@NileRed]

+rajesh shahi rajesh shahi I really should! Good call

[@rajeshshahi1000]

+Nile Red hey what is your favourite element.

[@romainetomatoes2416]

+rajesh shahi rajesh shahi I would guess carbon, since he does a lot of organic chemistry on his channel, and it isn't organic unless you have carbon... Organic chemistry is much more interesting than inorganic, because it has so much more to offer.

[@rajeshshahi1000]

+hyvää-elämää-98 I guess he likes it because it is the king of the elements.

[@benzenering2183]

Yeah. You'd think, that inorganic chemistry would be more interesting than organic, because organic chemistry basically is about ~10 elements and inorganic has all the elements, but getting further into organic chemistry, it is really fascinating, and I'd say that it's just closer to us - humans and overall nature. But it's just preferences, I guess.

[@charliemallindine8164]

For edited videos I would like to see eosin, for future vids I would like to see uracil and nonivamide

[@SciDOCMBC]

did you ever made oxalyl chloride?

[@dodoipav]

Is it possible to dry aluminium chloride Hexahydrate with this method?

[@rakhivishwakarma3110]

Hey, I tried the dehydration of Oxalic acid using toluene by vacuum distillation. But no use. Technically, it should have worked. But I don't understand why it didn't! Can you help with the reason?

[@dimaminiailo3723]

To drain oxalic acid dihydrate by distilling water azeotrope and toluene, you must decompose the dihydrate into water and oxalic acid, which is most effective at higher temperatures. Vacuum in this case does not give any advantages and only harms: toluene flies into the pump, the necessary azeotrope may not even be formed, oxalic acid does not give water.

[@highlyconcentratedbleach5249]

Can you purify oxalic acid from rhubarb?

[@marcingoawski9305]

Yes, but you need green rhubarb leaves not delicious red stalks. And you would need like 1kg of leaves to get 5g of oxalic acid.

[@KevFlaAVCHD]

I like your videos and I hate to criticize BUT.....that isn't a Dean Stark apparatus. It's a Barrett apparatus. The only difference is the stopcock at the bottom allowing you to drain off the collected fluid. The Barrett is much nicer and easier to use, in my opinion anyway.

[@DaveDVideoMaker]

Aka ethanedioic acid.

[@joulesjams20]

WHAT?? you said Dichloromethane not just DCM!!

[@spaceman7019]

I thought it said drinking

[@mrwinemaker]

I have a Dean-Stark without a drip valve. Any reason why?

[@afreenshaikh8406]

😍😍😍

[@martincarrera8217]

is there any way I can recycle calcium chloride or make it

[@jamie91995]

How dangerous is oxalic acid?

[@scippap]

You dehydrated oxalic acid to then add hydrous DCM? Kind of defeats the purpose...

[@BackYardScience2000]

Why do you think that? Honestly curious.

[@TheIdeanator]

Do a Piranha one and dissolve a diamond.

[@meganie8]

You don't use a Graham condenser for a reflux!

[@NileRed]

+meganie8 You are technically right! I shouldnt have because they can get clogged. You can use them, you just need to be careful. I will add an annotation in the video. The reason I used it is because it was my only clean condenser at the time :p

[@meganie8]

+Nile Red Not only because it can get clogged, it also has a very small surface area so the cooling capacity is very low. For a reflux you need a high cooling capacity. A Graham condenser is only used to cool the condensate down after a destillation. Btw: Do you have problems to buy lab ware in Canada? No one here in Germany would use Chinese lab ware, not even at home. :D

[@NileRed]

meganie8 We use chinese stuff mostly because it is A LOT cheaper

[@NileRed]

***** Thanks! So far for me though, all of my chinese glassware has been good. Ive heated some up to 350-400C and had no problems or used them with acetone/dry ice

[@ColinRies]

I'm from Luxembourg and so far I only used Chinese glassware because it is much cheaper than German stuff. I did break an allihn condenser, a round-bottom and a vigreux coloumn due to stuck joints, but I don't think that quality equipment would have made a difference. Besides, breaking a 20€ allihn condenser doesn't ruin your day as much as breaking a 80-100€ one, especially when you're still a student and don't want to spend just about all your money on glassware. Those three Chinese things I broke combined are cheaper than a single one of them on Amazon.de .... The most expensive piece I own is a 30cm dimroth cooler that I got for about 25€ on ebay. It feels really good though and it has held up til now, so I don't see why I would want to "waste" 80+€ on one from DURAN or whatever.

[@nivmoshe5536]

how do you know its DIhydrate oxalic acid and not MONOhydrate just for example...

[@ghunther0111]

I don't believe there is a mono hydrate, when water binds with it, it binds with 2 water molecules

[@nivmoshe5536]

why? is there a way to know the hydration level ?

[@ghunther0111]

+Niv Moshe (Dindibo4) I believe it's just an accepted fact for most molecules

[@planetsoccer99]

Just dry it and weigh it before and after, then do some stoichiometry. That's a high school chemistry lab.

[@Cristi0986]

I did nt find oxalic chloride vid....

[@caidencoleman9503]

I read it as Dean-stark asparagus lol

[@a1b2c3z44]

Is it possible to split the C=C bond in indigo? please

[@teunkruijer]

i don't know what you mean with indigo? but you can break c=c bonds easily with halogens like fluor and chlorine. Or you could use an anhydrate compound to initiate a chain reaction. This method is used to make plastics.

[@a1b2c3z44]

well if you google ˇindigo structure" you will see that it is made of two almost-tryptamine-like mollecules, connected via C=C. The molecule has nitrogen in a 5-ring in it and a -OH or a =O group attached to a ring, so i need a reagent that wont ruin anything else than that + wont ruin the organic solvent. sorry for bad english

[@teunkruijer]

Yeah sorry man, the c=c seems quite hard to reach and i can't think of anything that n wouldn't react with the rest of the molecule first. Maybe if you use iodide and heat it up a bit? Good luck on it anyways.

[@mtalhakhalid1679]

What does DCM smell like

[@TheTdw2000]

Sweet, like chloroform

[@boltblast3262]

I feel like this channel is becoming Nurdrage.

[@ATLTraveler]

Lol you dont have a heating mantle but you have all these strange apparatuses...

[@marcingoawski9305]

Make diphosgene!

[@googleeatsdicks]

+Marcin Goławski Or maybe not.

[@marcingoawski9305]

+Anticonny It's easy. just chlorinate methyl formate. it can be used to make oxalyl chloride,

[@googleeatsdicks]

Marcin Goławski I did not say that it's not easy. It is still highly toxic and it can easily release even more toxic phosgene gas.

[@marcingoawski9305]

+Anticonny True. But would be so cool to see it anyway.

[@googleeatsdicks]

Marcin Goławski Indeed.

[@theamateurscientist]

is methyl salycate toxic

[@Quintinohthree]

Yes, quite so. Not too toxic to handle but the vapors are toxic enough that you shouldn't smell them.

[@theamateurscientist]

+Quintinohthree ok thanks because it is in surgical spirit

[@ShadowsLetsPlays37]

+the amateur scientist It is not "Toxic" but you still shouldn't eat it and avoid breathing in aerosols/vapors but that is the general drill with any chemical.

[@theamateurscientist]

+ShadowsLetsPlays37 correct visit my channel if you have time

[@tmfan3888]

is the pink colour due to Mn2+?

[@ColinRies]

where would that have come from?

[@tmfan3888]

Colin Ries just random guess

[@ColinRies]

TM Fan you could also have said that it was from pink fluffy unicorn dust lol

[@KingofJ95]

I get it. It's a ghetto setup because it looks like something out of a meth lab.

[@goyabee3200]

It's a trap!

[@josefumi]

:D

[@yanikkunitsin1466]

You havent used oxalic acid. Nothanks to patreons

[@googleeatsdicks]

Can oxalic acid be dehydrated in a vacuum desiccator?

[@rakhivishwakarma3110]

I think it should work. But, I tried this with vacuum distillation. But no use.