Perfect, now I can take off my nail polish easily!

This was a major process in Alchemy. They would dry distill metal acetates (Pb, Sb, Sn, Ag, and Cu acetates for example) to obtain various distillates, one of which was acetone. Your production of a yellowish oil and then white smok was described in old alchemical texts. According to those same texts if you had continued the distillation at even higher temp a red vapor will come over. The white smoke can also be condensed into liquid at cold temps. I haven't replicated these experiments myself. I have just read about it so I offer it up as an interesting bit of chemistry history.

Broken glassware breaks my heart :(

SOooo... some notes: The heating mantle probably wasn't solely responsible for the destruction of your glass flask. Calcium carbonate can decompose into CaO and Ca(OH)2. Both are strong bases, and under the correct conditions that will work to drop the temperature at which the glass will dissolve into a liquid. Second, you were probably getting a carbamide product by reacting the acetate with atmospheric nitrogen. it'd be a slow reaction under stp, but, as already noted, you're not operating at stp. Amides have odd smells and yellow colors. spermidine ftw.

I think that one of your major byproduct might be the aldol condensed acetone, mesityl oxide. It is described as a flammable pale yellow oil with a strong smell of "cat urine, peppermint- or honey-like" with a Bp arround 130 degree C.

I had the exact same thing happen with a roundbottom and heating mantle! I was using it on a higher power setting, but the flask fused to the mantle and cracked the glass. In my case, I was doing a steam distillation on powdered cinnamon (as in your cinnamaldehyde video), but the cinnamon was all pooled at the bottom. If I were to speculate, the cause is having a solid versus a liquid at the bottom of your flask. Heating mantles are typically meant for boiling liquids, and as the liquid vaporizes, it carries heat (energy) from the heating mantle with it through the apparatus. This, in turn, carries energy away from and cools the glass. If, however, the mantle is in contact with a solid, this latent heat of vaporization can't serve to cool the glassware, so the flask reaches a much higher temperature, high enough where it can melt. Furthermore, the temperature differential between the top and bottom of the glass becomes so great that the flask cracks around the middle (both of our flasks cracked in exactly the same way, right along the equator). This probably also explains the smell. The temperature becomes so great in the salt that it, and any trace impurities, will actually begin to burn. Not only that, but the heating mantle itself probably had components that were breaking down and burning. I had the same thick white smoke coming over in my cinna-still. I didn't test the flammability like you did, but it smelled strongly of a campfire or burning leaves, and left a thick red-brown oil in my receiving flask and in the joints of the distillation apparatus. I was using water, but the oil might be acetone soluble, making for the off color solvent you got. For ANYONE attempting to use a method like this, I strongly recommend either using a different, more even method of heating (like an oil bath), or adding a liquid to the boiling flask in which the salt is not soluble and stirring vigorously. This may impede the reaction rate somewhat, and yield a less pure product from boiling liquid, but you can always redistill. The solvent will keep the boiling flask at a constant temperature as it vaporizes, and the stirring will make sure the solid can't pool at the bottom and crack the glassware. Better a slower reaction than broken equipment. But there may be an even better way.

"And I guess this kinda made it easier to get inside" LOL

When making dangerous flamable liquids and gases from things we eat, I always think back to when most people thought chemistry was sorcery, you can't really blame them haha Imagine going back in time and saying you can make flamable liquids from egg shells and apples.🤣

if there were any sugars in the calcium acetate from the tums that could explain the smell, color and the black ash.

I really enjoy watching you do your work. I have been a wannabe a chemist for 60 years and I am envious at your skills and knowlege.

These 'Ketonic decarboxylation' reactions run just fine in steel over a flame. Glassware is beautiful and precious (and not cheap), so...be kind to your glass. :) Nice write-up, however, and your content is VERY enjoyable. Bravo!

You are truly a role model of mine. I'm taking an AP chemistry class this year and it is amazing understanding everything you are doing! Thanks.

poor heating mantle

i think the yellow stuff could be from the distructive distillation of some sugar left over from the tums.

Thanks for your hard work. I really like your videos!

Dude great vid. Everything you've shown lines directly up with many Alchemy Books I've read, mainly study Frater Albertus, the Book Das Acetone as well. Thank you very much for this as it confirms so much about Alchemy in one video. Please respond and we can talk further. BTW, may want to look up a guy named Rubaphilos online and get his PDF books on his website. It will answer alot of questions than I can at the moment.

Deep condolences for your glasses & heating mantle... ~big thanks for sharing this kind of knowledge :D ~

I think the yellow / orange stuff and the weird smell (partly) came from self-condensation of acetone. Acetone, when heated in the presence of an acid or base (calcium acetate is basic), can undergo aldol condensation to form initially diacetone alcohol, then mesityl oxide, which has a weird odor reminiscent of peppermint, honey, and cat urine. (I've smelled it before from intentionally dropping KOH pellets in a waste acetone bottle and waiting for a week or two) Then further condensation can occur yielding phorone, isophorone, and other smelly products. Finally enough units of acetone molecules are condensed making long enough conjugated alkene systems to exhibit yellow or darker colors.

That's why you should always leave a tiny gap between the heating mantle and the flask, you can always add insulation over the flask (like aluminum foil) if you need better heat transfer... Also if any liquid or whatever ends up leaking from your setup, it doesn't glue the mantle into the bottle so easily :)

Shame about the flask but at least now you own a new observation dish! Thanks for leaving this part in the video, I feel that learning how things can go wrong is at least as important as learning how they can go right.

Sorry to see you lose a flask and heating mantle over this, but thanks for the video! I had previously made some calcium acetate that I'm hoping to make sterno and acetone with, so I was happy to see you make exactly those videos. Did you ever find out what the flamable smoke and the yellow liquid were? Also, and perhaps most importantly, what can you do to prevent any future flasks from melting into a mantle? Thanks again for the video!

a small tip: when you're trying to isolate your aparatus with aluminium foil to have it stay hot, you should put the more reflective side of the foil TOWARDS your aparatus. the heat will reflect better. for cooling it's the other way around. hope that helps! nice video as alyways!

i,needed one thank you for the future

I think a polymerisation of the produced aceton appeared to form the yellow oil.

Yes .. In Alchemy the white fume is called the white King and the red fume the Red Queen .. Some of the elements can be joined in certain ways to create Philosophical elements .. Living waters and Earths in Ripleys Realm .. It is also the way to the philosophical Stone .. But there are many others too ..

Will you ever do, or have you done, a video on the cumene process? I think it would be an interesting one to see.

The brown/yellow is what we call in alchemy the sulfur(essential oil) of calcium which is the most bioavailable form of calcium

Can you highlight the Cumene process sometime?

thanks for sharing, very interesting stuff. sorry about your sick gear

Cool, I had been waiting for this particular synthesis for a while.

How about isolating some stuff from dry disstilation of wood? I did it once in my school and the heating mantle got red hot and the flask started to melt but it survived. The heating mantle surprisingly was still ok.

I would love for you to make a videos making 99.99% samples of each of the elements of the periodic table from either chemicals or scrap.

Hey nile, sorry about the the mantle. About the yellow funky oil, my guess is that because calcium salts were not particularly pure (tums) they may have had traces of nitrogen/sulphur compounds (tartrazine is listed in the inactive ingredients, which contains both as well as some aromatics) which as you know, smell, they probably reacted at the high temperatures of the dry heat and decomposed (low boiling fraction) or polymerized/reacted with some of the acetone (flamable fumes were likely a higher molecular oil that got "steam distilled" carried by the acetone vapor). If you ever decide to try it again id love to see what changes if you use recrystalized calcium acetate and maybe using a high boiling "solvent" and boiling a suspension of the salt in like mineral oil instead of direct dry heat.

You asked in the video what is the yellow stuff. It is polymer of acetone, ketonic resin. This starts to form already at 250°C by my experience. I had silica aerogel as catalyst but calcium makes even better one.

Perhaps the flammable smoke contained ketene from pyrolysis of the acetone. Looks like your mantle got hot enough. I hope you had good ventilation!

Rip heating mantle. Never really been into chemistry however after finding codyslab and your channel, I do find it quite interesting :P

This is so cool and useful, acetone is very hard to get where I live so this helps alot. Do you think you could do a video on purifying Calcium Carbonate from Limestone rocks? I think this would make a very interesting video, and you can pretty much find Limestone everywhere. Thanks.

At 1:34 did you reverse the footage, on the left side of the flask the drop is goes up and down a few times??

Making pre-heated copper glow red as it catalyzes acetone is a cool experiment.

Interesting. I needed a way to obtain non-denatured acetone for LSA extraction from Morning glory seeds. Everything around here has denatonium benzoate added to it.

You should do a video on making acetone by electrolysis of citric acid.

7:32 there's always a silver lining

The yellow collored liquid may be isophorone. Because the reaction mixture is basic and good for aldol condensation reactions.

I am sure some self condensation occurred to the formed acetone due to the basic conditions. A very dry calcium acetate should reduce it.

Do you have NMR? It would be interesting to see the structure of all organic molecules you made.

4:42 poor Mr. Barr

What temperature did you distill at? I tried doing this over an open wood fire but I had no luck - perhaps it was too hot

+Nile Red Can you do a synthesis of potassium nitrosodisulfonate?

That stream would be a nice picture

Nile can you do a video that explain more about cumene reaction or even synthesis yourself acetone with cumene proceses?

Could the yellowing be from the sugars in the tums

The white smoke was probably a mixture of H2O, CO2, CO (because the residue in the flask contained carbon and it might have reacted)

Could the yellowy/dark residue be leftover decomposed sucrose from the tums?

I wonder if running it through a separatory funnel between distillations would have helped

Pour water,acetone mixture on top of copper solution. Somehow they become immiscible. I used acetone, vinegar and water to dissolve matchheads.

is the fractional destilation important or can i do a normal destilation

My gut says the color and smell are from aldol polymerization driven by the high temperatures--the color reminds me of the funky orange old base baths turn after a while and that's also caused by aldol polymerization.

Do you have a video on the making of acet-aldehyde?

Oh good, I was running low on Brakleen! Thanks

RIP heating mantle... You were too beautiful for this world...

Awesome video, I use this as I have a lot of eggs (long story) and acetone prices are outrageous in Australia... so I can just make some acetone from eggshells. Just a little nitpick - you use the aluminium foil as an 'insulator' when it's actually a good conductor of heat. Still though everyone understands the wording so no need to change anything!

I wonder what should you have done differently to preserve your flask and mantle?

doesn't insulating a column in such a low b.p. distillation completely negate the fractionating column?

Do you think you can use other metal acetates instead?

The yellow color is from conjugated ketones, things like 2,4-pentanedione or higher homologs. distill it down and take an NMR. The stinky stuff is probably formic acid or formates. Think about using 50:50 benzoic acid and acetic acid.

Can you show us how to make isopropyl alcohol from acetone?

I bought NaOH from my local supermarket, but as expected it was not very pure. I wanted to purify it, but I didn't know how. If somebody has any idea, I will be very happy to hear it.

how do you clean out all of those glass things out so clean?

what if you disolve nitrocellulose in acetone and light it? what if you mix that with homemade napalm?

damn bro! Glass ware and equipment is so expensive

Maybe you got some other simple ketons because of remaining phosor compounds and other stuff from the pills you used. They also contain adipic acid which might have caused the burning in the flask.

Yellow color from the principe sulfur of calcium, it's acetone of calcium. You ll get a red color with acetate of lead, same with iron and Cu, Sb. Your calcium was just start to be open. Sir Weidenfield worked on it a long time ago.

Lab Safety Tip from a highschool student: But a bunsen burner at the output the white smoke comes out of. It'll just burn off.

whats the white smoke

Question: where did you get all of your equipment? Your videos really want me to try out some experiments, but I hit a dead end trying to find all the stuff you have.

Thanks!

would you try t oget the cumene process done? or is it impossible at lab scale?

I propose to you that the weird smell is "mesityl oxide" - aka 4-methylpent-3-en-2-one - which smells like honey and is formed from base-catalyzed dimerization of acetone via the aldol condensation. It may also contain some phorone, the trimer, which smells like geraniums or isophorone, the cyclic trimer, which smells like peppermint.

Was anything spilled on the mantle? It may have partially short-circuited, and gotten extra hot in places.

Wow, you were heating the shit out of that boiling flask, weren't you. Nice job.

would you plz let me know what is the yield percentage by this process would be.thanks

@nile red calcium acetate can form polymers if too much heat is supplied

color is because of carbon, on your video of preparing CaCO3 from Tums , you left some carbon, you mentioned that the stove is incapable of burning away carbon

ALSO bases help promote the reaction. I am guessing by helping to scrub out the CO2 created to prevent reverse reactions and ending up where you starting out. SO i would try adding some NaOH or CaO...........JUST A GUESS THOUGH

Why not filter the distilled acetone several times like you did with the Calcium acetate when it was still liquid? Would that help filter out impurities from the resulting acetone?

is it possible that the flammable gas is carbon monoxide? there was alot of organic material in the tums that turned to black powder i know that when you heat wood in a closed vessel like that it produces carbon monoxide

Could the flammable smoke kind of thing actually be acetone vapor that didn't condense?

Why don't you use a Bunsen burner or spirit lamb

Would a similar thermal decomposition of calcium formate give formaldehyde gas? Asking, because formalin is hard to come by locally, yet formic acid is easily available in hardware store.

It did not destroy it, it simply mad it more interesting!

If the smell is similar to cat urine, I would say your synthesis produced a little bit of thioacetone. I've played with the stuff, and the odor threshold is extremely low. The small amount of sulfur from the dyes in the TUMS or egg shells would probably be enough to odorize your product without being visibly noticeable in your calcium acetate. But that's just a shot in the dark. Good video, though. It's nice to see some of the old fashioned syntheses for compounds we take for granted.

How does 'insulating with aluminium'work ? Doesn't this just let through any infrared: read it is probably completely useles, or do I miss something ?

Carnuba wax or pill buffer like dextrose or similar “sugar “ is causing the weird color & smell.

Maybe the yellow came from coulouring, flavouring or the different sugars used in the tums.

Why not try insulating the bottom of the flask with some aluminum foil that way if it did melt the glass it didn't totally destroy the heating mantle?

So you recover calcium carbonate at the end, it's basically a catalyst for the reaction 2 acetate -> acetone + CO2 ?

Nice video, id wait for it :))

I think this caco3 caused your glass to melt it is used to make glass more workable.

Can I use a hot plate with an oil bath for this experiment?

I think the yellow is due to sugars that might be present in the vinegar. I always get a paste when i try to crystalize acetates instead of hard crystals.