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.
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.
Nathan Hopkins I know I’m ‘necroposting’ here however I suggest a sandbath rather than a heating mantle. At least the flask is less likely to crack at its equator because heat outside the flask is more even. Also if as you suggest the flask softens due to the pyrolysis products reacting with the glass a sudden failure is more of a disappointment rather than a catastrophe in a sand bath. It looks like the acetate must be very pure to liquify rather than char in the flask. Old texts specify an optimal temperature of 380oC for distilling calcium acetate, well above the softening point for borosilicate lab glass.
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.
Orbital Overlap I would agree. Simply adding base to wet acetone creates a yellow color. In fact some preps of mesityl oxide simply involve grinding acetone and KOH in a mortar and pestle.
+Nile Red get an infrared thermometer, I got mine on Amazon for $10.00 it works great and you can measure temperature of things except for glass, liquids, and plastics from a distance.
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 heard stories about a guy who spilled a flask of spermidine once. I was told the whole lab smelled like a brothel for several days. Apparently, the few people who visited it in that time period stared really weirdly at the chemists!
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!
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.🤣
Ok that makes sense. I dissolved chalkboard chalk once, it mostly dissolved, but there was a gray white precipitate left over, that was probably the calcium sulphate.
hmm. I didn't know blackboard chalk is mostly calcium sulfate... That would explain why when I tried to make calcium acetate from vinegar and a big chunk of blackboard chalk and let it react for a long time, I got about half a gram of yellowish unpure calcium acetate... Would have never thought that blackboard chalk would normally contain so little calcium carbonate. Learning new things everyday, huh...
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.
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.
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!
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 :)
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.
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.
@@Sup3rman1c Here in Colombia this substance is controlled, because illegal substances such as drugs are produced with it, that's why here it is very difficult to get acetone.
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.
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 ..
I like piranha solution. If you have pretty well cleaned it and just have a little organic residue left, you end up with nice clean glassware. If you did a poor job and have lots of organic matter, you end up with DANGER DANGER DANGER and fun.
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!
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.
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.
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.
What's really cool about this is that I have chickens and pears that I'm fermenting for vinegar, so I can do this over and over and have unlimited free (aside from electricity) acetone!
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.
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.
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.
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.
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
The flammable gas produced is probably methane. You are basically doing a soda lime decarboxylation making methane (63%) and at the SAME TIME a ketonic decarboxylation making acetone as a side product (37%) and that is why the yield is so low. It is a side product. When you make benzene from benzoic acid doing a soda lime decarboxylation you are ALSO making benzophenone (a ketone) doing a ketonic decarboxylation. But benzophenone boils at like 300 C so you never realize you made it. But it is the high boiling stuff left in the pot after distilling it. THIS IS ALL JUST A GUESS BUT IT SOUNDS LOGICAL
That's nice. You could start by showing as alternatives to some of the methods used in your videos or what we can collect from stuff we have at home. Thanks in advance.
+Nile Red probably with either cheaper glass ware or no standard instruments... Ghetto rig chemistry basically? I mean I personally don't care I have no intentions of doing any experiments.
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Pour water,acetone mixture on top of copper solution. Somehow they become immiscible. I used acetone, vinegar and water to dissolve matchheads.
Acerone vapor isn't that thick, I have distilled acetone several times and a half decent water cooled liebig alongside eith ice cooled receiving flask will condense pretty much everything.
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.
You shouldn't insulate the column for things with a low boiling point like acetone: it lowers its ability at separating the compounds that go through it. Instead, to get good purification and get as close as possible to the pure chemical or azeotrope, you should increase the heating until the vapor front just barely reaches the condenser. (The rule of thumb is that the more heat your column radiates per amount of chemical distilled, the better the separation. It's purely a question of entropy: separating chemicals in the gas phase has a negative entropy, so you must compensate by radiating heat outside and bring balance to the -Force- erhm... Gibbs energy.) Also, it would be really cool if you recycled the black deposit at the bottom of your flask with some acetic acid, to make more calcium acetate and put it through an other cycle of acetone production. You'd have an actual chemical "cycle" with the calcium! Quite a change from the usual "straightforward" reactions...
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.
While it is true that calcium carbonate decompose into calcium oxide, the temperature that the decomposition occurs at is 840°C, whereas the decomposition from calcium acetate to calcium carbonate and acetone occurs at only 160°C. So the compound would have had been heated to a much higher temperature than it was likely at. It is likely organic compounds that caused the impurities in the mixture.
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.
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?
Yeah man, damn corrupt goverments. Don't they know dimethlyltryptamine cures cancer??? THEYRE JUST PAID SHILLS FOR THE MEDICAL COMPANIES MAAN BELIEVE ME. DAAMmn NOt TAKIMNG my PSUchossis mediCAtione beacus FUCK dem mEMDs companies !!! TAKE psycheDELICS and you GETT cureEDs Lik ME!!!
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!
How come nobody thinks of the formation of ketene!? The rxn should be a form of pyrolysis, so it is logical to think that the formed acetone will pyrolise to ethenone, an even more lethal compound than phosgene. Any advice is welcomed.
Regarding the melting of your 1000 ml flask, did you buy it from China? I didn't see the word "Pyrex" on flask, which leads me to suspect that it wasn't Pyrex. "Solder glass", which is used to join pieces of glass having higher melting points, can melt below 500 C.
Well if that's the same calcium acetate that you made from egg shells, maybe the yellow smelly stuff is Sulfur/Sulfur dioxide that came from the eggs? i remember hearing that it is responsible for the smell of boiled eggs being peeled off.
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.
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.
Well, I think the point is, you lost your setup fro nothing.. Low, and bad aceton, and the flask, and the heater is gone. But, the video is actually great!!!!
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.
Hi do you have access to any of these texts?
Totaly agree with you. Ora & labora
The first law of alchemy is “To obtain something of equal or greater value must be lost”
you can read STARKEY, RIPLEY,BECKER, WEIDENFELD
@@wyatthouston8583 First law in alchemy should be total silence
Perfect, now I can take off my nail polish easily!
"Easily"
@@justinturner2861 what's that mean?
You can buy 100% acetone for basically nothing. Many nail polish removers are pure acetone.
@@omniferousswan593 you've clearly never removed nail polish
@@alexhobbs1208 I have many times.. What does that have to do with what I said? My nail polish remover is 100% acetone.
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.
Nathan Hopkins I know I’m ‘necroposting’ here however I suggest a sandbath rather than a heating mantle. At least the flask is less likely to crack at its equator because heat outside the flask is more even. Also if as you suggest the flask softens due to the pyrolysis products reacting with the glass a sudden failure is more of a disappointment rather than a catastrophe in a sand bath. It looks like the acetate must be very pure to liquify rather than char in the flask. Old texts specify an optimal temperature of 380oC for distilling calcium acetate, well above the softening point for borosilicate lab glass.
As a non-chemist my inclination would be to do the heating in a metal container. Is there any reason this should be done in glass?
@@siggyincr7447 yes
@@siggyincr7447 glass is non porous and doesn’t react with strong chemical compounds as some metals do.
@Nathan Hopkins you should have added a stir bar to the cinnamon flask and then heat it.
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.
*CAT URINE*
best band name
Orbital Overlap I would agree. Simply adding base to wet acetone creates a yellow color. In fact some preps of mesityl oxide simply involve grinding acetone and KOH in a mortar and pestle.
Those are 3 smells I try to keep together in the lab... Makes for really interesting "take your kids to work day" 🤣
Broken glassware breaks my heart :(
It was a sad sad day...i got a new mantle and 2 new flasks though :p
Nile Red Every cloud has a silver lining :)
+Nile Red get an infrared thermometer, I got mine on Amazon for $10.00 it works great and you can measure temperature of things except for glass, liquids, and plastics from a distance.
+meganie8 You act like he cares about your opinion...
if you cant measure glass/liquid temperature it doesnt much helpful :\
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 heard stories about a guy who spilled a flask of spermidine once. I was told the whole lab smelled like a brothel for several days.
Apparently, the few people who visited it in that time period stared really weirdly at the chemists!
Spermidine in the air with the giant empty jugs of anal lube used in previous videos...
thanks for the input!: )
What was the white smoke doe?
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!
I believe he makes a point of using glassware wherever possible so that the reaction is visible. A lot of people come here for the pretty colors :)
@@ryjelsum True that. Imagine watching these when everything is hidden in the containers.
"And I guess this kinda made it easier to get inside" LOL
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.
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.🤣
Isn’t that what they did back then?
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.
What did you end up getting into? Chemistry?
i think the yellow stuff could be from the distructive distillation of some sugar left over from the tums.
Yeah chalk is usually mixed with a little clay to hold it together.
Ok that makes sense. I dissolved chalkboard chalk once, it mostly dissolved, but there was a gray white precipitate left over, that was probably the calcium sulphate.
hmm. I didn't know blackboard chalk is mostly calcium sulfate... That would explain why when I tried to make calcium acetate from vinegar and a big chunk of blackboard chalk and let it react for a long time, I got about half a gram of yellowish unpure calcium acetate... Would have never thought that blackboard chalk would normally contain so little calcium carbonate. Learning new things everyday, huh...
poor heating mantle
At least that kind is cheap
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.
Calcium oxide is also basic
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.
Thanks!
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!
Does it actually have that big of an effect? I always kind of assume it wouldn't make a huge difference
well, the science would support it and i made good experience with it, so try it! :)
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 :)
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.
Deep condolences for your glasses & heating mantle...
~big thanks for sharing this kind of knowledge :D ~
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.
Acetone hard to get? You live in africa or what?
@@Sup3rman1c Here in Colombia this substance is controlled, because illegal substances such as drugs are produced with it, that's why here it is very difficult to get acetone.
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.
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?
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 ..
*this* is why i came searching for this
I think a polymerisation of the produced aceton appeared to form the yellow oil.
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.
how do you clean out all of those glass things out so clean?
And if that^ does not work strong acids and ultimately piranha solution.
I like piranha solution. If you have pretty well cleaned it and just have a little organic residue left, you end up with nice clean glassware. If you did a poor job and have lots of organic matter, you end up with DANGER DANGER DANGER and fun.
Thanks for your hard work. I really like your videos!
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!
Perhaps the flammable smoke contained ketene from pyrolysis of the acetone. Looks like your mantle got hot enough. I hope you had good ventilation!
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.
Do you have NMR? It would be interesting to see the structure of all organic molecules you made.
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.
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.
Nice pfp OP.
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?
Will you ever do, or have you done, a video on the cumene process? I think it would be an interesting one to see.
What's really cool about this is that I have chickens and pears that I'm fermenting for vinegar, so I can do this over and over and have unlimited free (aside from electricity) acetone!
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.
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.
The white smoke was probably a mixture of H2O, CO2, CO (because the residue in the flask contained carbon and it might have reacted)
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.
Austris Mazurs
That is a brilliant question. I’m sure it would work.
The yellow collored liquid may be isophorone. Because the reaction mixture is basic and good for aldol condensation reactions.
Could the yellowing be from the sugars in the tums
doesn't insulating a column in such a low b.p. distillation completely negate the fractionating column?
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.
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
i,needed one thank you for the future
Was anything spilled on the mantle? It may have partially short-circuited, and gotten extra hot in places.
The flammable gas produced is probably methane. You are basically doing a soda lime decarboxylation making methane (63%) and at the SAME TIME a ketonic decarboxylation making acetone as a side product (37%) and that is why the yield is so low. It is a side product. When you make benzene from benzoic acid doing a soda lime decarboxylation you are ALSO making benzophenone (a ketone) doing a ketonic decarboxylation. But benzophenone boils at like 300 C so you never realize you made it. But it is the high boiling stuff left in the pot after distilling it. THIS IS ALL JUST A GUESS BUT IT SOUNDS LOGICAL
Can you show us how to make isopropyl alcohol from acetone?
Hey Nile, I've got a suggestion. Could you make a series on how to start with experiments at home? With simpler tools and equipment?
Yes pls
Yes pls
I have been planning to do this, but i dont really know where to start.
That's nice. You could start by showing as alternatives to some of the methods used in your videos or what we can collect from stuff we have at home. Thanks in advance.
+Nile Red probably with either cheaper glass ware or no standard instruments... Ghetto rig chemistry basically? I mean I personally don't care I have no intentions of doing any experiments.
Pour water,acetone mixture on top of copper solution. Somehow they become immiscible.
I used acetone, vinegar and water to dissolve matchheads.
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??
its probably a footage that is on repeat for him to talk
Could the flammable smoke kind of thing actually be acetone vapor that didn't condense?
Acerone vapor isn't that thick, I have distilled acetone several times and a half decent water cooled liebig alongside eith ice cooled receiving flask will condense pretty much everything.
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.
So you recover calcium carbonate at the end, it's basically a catalyst for the reaction 2 acetate -> acetone + CO2 ?
You should do a video on making acetone by electrolysis of citric acid.
7:32 there's always a silver lining
Making pre-heated copper glow red as it catalyzes acetone is a cool experiment.
I am sure some self condensation occurred to the formed acetone due to the basic conditions. A very dry calcium acetate should reduce it.
You shouldn't insulate the column for things with a low boiling point like acetone: it lowers its ability at separating the compounds that go through it.
Instead, to get good purification and get as close as possible to the pure chemical or azeotrope, you should increase the heating until the vapor front just barely reaches the condenser.
(The rule of thumb is that the more heat your column radiates per amount of chemical distilled, the better the separation. It's purely a question of entropy: separating chemicals in the gas phase has a negative entropy, so you must compensate by radiating heat outside and bring balance to the -Force- erhm... Gibbs energy.)
Also, it would be really cool if you recycled the black deposit at the bottom of your flask with some acetic acid, to make more calcium acetate and put it through an other cycle of acetone production. You'd have an actual chemical "cycle" with the calcium! Quite a change from the usual "straightforward" reactions...
That is true. I should have actually mentioned that about cycling the CaCO3 back to making calcium acetate!
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.
Rip heating mantle. Never really been into chemistry however after finding codyslab and your channel, I do find it quite interesting :P
at 3:57 you said that the white powder is Calcium carbonate but shouldn't the majority of it be Calcium oxide there instead? @NileRed
While it is true that calcium carbonate decompose into calcium oxide, the temperature that the decomposition occurs at is 840°C, whereas the decomposition from calcium acetate to calcium carbonate and acetone occurs at only 160°C. So the compound would have had been heated to a much higher temperature than it was likely at. It is likely organic compounds that caused the impurities in the mixture.
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 think you can use other metal acetates instead?
4:42 poor Mr. Barr
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?
I wonder if running it through a separatory funnel between distillations would have helped
NILE RED! HELLO MY FRIEND
hello!
Nile Red What do you think the yellow color & the strange smell were from?
Erstmal Disliken Unfortunately, I do not :(
0:49
''Very simpely to start off, all of the calcium acetate is added to a 1L round-bottom flask''
*spills almost all of the calcium acetate*
hey man, pouring stuff can be difficult!
NileRed do you know if Mg Acetate would work in a similar way to make Acetone ??
Wow, you were heating the shit out of that boiling flask, weren't you. Nice job.
Yo Nile, you should extract Dimethyltryptamine from bark or a plant that has a high yield of it.
I am going to stay away from drug related things for now! (well illegal drugs)
That's just what corrupt goverments say. It really is a awesome molocule. There's lots you can do with it (besides comsuming of course). Science man!
Yeah man, damn corrupt goverments. Don't they know dimethlyltryptamine cures cancer??? THEYRE JUST PAID SHILLS FOR THE MEDICAL COMPANIES MAAN BELIEVE ME.
DAAMmn NOt TAKIMNG my PSUchossis mediCAtione beacus FUCK dem mEMDs companies !!! TAKE psycheDELICS and you GETT cureEDs Lik ME!!!
Cool, I had been waiting for this particular synthesis for a while.
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 think it is probably for the heat radiation and not for the contact heat transport.
what if you disolve nitrocellulose in acetone and light it? what if you mix that with homemade napalm?
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.
How come nobody thinks of the formation of ketene!? The rxn should be a form of pyrolysis, so it is logical to think that the formed acetone will pyrolise to ethenone, an even more lethal compound than phosgene. Any advice is welcomed.
thanks for sharing, very interesting stuff. sorry about your sick gear
RIP heating mantle... You were too beautiful for this world...
I Made this Process very often , but my flasks were never melted.
how much degree have you used at destillation?
+Nile Red Can you do a synthesis of potassium nitrosodisulfonate?
Acetone burns with a blue flame instead of a yellow flame. This indicates that there might be some impurities.
Carnuba wax or pill buffer like dextrose or similar “sugar “ is causing the weird color & smell.
Regarding the melting of your 1000 ml flask, did you buy it from China?
I didn't see the word "Pyrex" on flask, which leads me to suspect that it wasn't Pyrex.
"Solder glass", which is used to join pieces of glass having higher melting points, can melt below 500 C.
Well if that's the same calcium acetate that you made from egg shells, maybe the yellow smelly stuff is Sulfur/Sulfur dioxide that came from the eggs? i remember hearing that it is responsible for the smell of boiled eggs being peeled off.
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.
So as long as you have some calcium acetate (or calcium carbonate) you can indefinitely turn acetic acid into acetone?
Theoretically
This stuff is fascinating!
calcium hydroxide should work to react with vinegar for the acetate right?
yes, acid base reaction: OH- and H+ form Water and what's left is Calcium and Acetate
damn bro! Glass ware and equipment is so expensive
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 ?
Why don't you use a Bunsen burner or spirit lamb
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.
safta leonard acetates are hard to crystallize into large crystals. Best way I found to clean them up is to wash it in acetone.
I think this caco3 caused your glass to melt it is used to make glass more workable.
@NileRed
Will the acetone produced here remove grafitti paint ?
I wonder what should you have done differently to preserve your flask and mantle?
Well, I think the point is, you lost your setup fro nothing.. Low, and bad aceton, and the flask, and the heater is gone. But, the video is actually great!!!!
Nice video, id wait for it :))