Benzaldehyde from polystyrene (styrene ozonolysis)
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- Опубліковано 22 лип 2024
- Don't mix ozone with organic solvents unless you know what you are doing obviously. Things can go boom boom.
Sauce:
www.sciencemadness.org/talk/vi...
pubs.acs.org/doi/abs/10.1021/j...
www.sciencemadness.org/talk/fi... - Наука та технологія
As for separation of aldehydes from everything else, you can use bisulfide adduct. There is nice protocol on jove (J Vis Exp. 2018; (134): 57639.; doi: 10.3791/57639; PMCID: PMC5933314; PMID: 29658940) and in few of Org Synth synthesis. This can be pretty usefull to extract aldehyde from, as NurdRage called it, Conglomeration of Reactants and Alternative Products (CRAP). Keep going! You have my sub :)
If you add a bit of titanium oxide, calcium oxide, and copper powder, it will cleave the polymer at a lower temperature.
GREAT VIDEO!!!!!!!!!!!!!!!!! I depolymerized some polystyrene ONCE. For a 50 foot radius around my house you could smell the monomer styrene bad. Never make that again. That smell carries big time. I looked in to this experiment BIG TIME about 4 years ago and wanted to do it. But after i researched it i found that making an ozone generator is very time consuming and cost money and the amount of O3 produced would be very small per each unit of time. And to buy one big enough so it did not take forever to do an experiment was to rich for me. Plus i found out dry ice in my area is a long drive to get it and $40 a pop every time i bought some. And that means every time i did an ozonolosis i would need to spend $40. Plus the cost of an oxygen tank. And all the ways you can explode. I was not as brave as the guy in the video. Or really as smart cause i could have done some micro reactions like he is doing.
SAFETY TIPS if you try to scale up.......NOT FOR for micro reactions like in the video. Plus his ozone generator is probably barely making an ozone. (1) The pot should be MINUS 78C when styrene is being put threw ozonolysis and for most alkenes. Although some alkenes can go through ozonolysis as hot as MINUS 30 C. but not for styrene (2) Your set up should be ALL closed up except 2 in tube that goes all the way down threw the liquid in the pot so you can bubble your ozone and O2 in to the styrene. And also have a tube for exiting gases. But do not let the tube dip down into the liquid in the pot. On the out port have at least 2 bubblers/suckback traps. And fill the bubblers with aqueous KI to kill any O3 that makes it of the pot. If both bubblers get BLACK then add another bubbler. (3) Nitrogen and ozonides blow up. And the pot will be make a couple different ozonides. So turn your oxygen tank on that is on the in port and flush out the system of all air. Now if you have some kind of home made ozone generator or one bought at a regular store to kill bugs. Then you will have to get some molecular sieves. The same size sieves they put in oxygen generators for old people. So they can breath. ANYWAYS you would need to run the air/O3 mixture coming out of the ozone generator and send it through the molecular sieves AND THEN That way the sieves filter out the nitrogen and then lead the remaining O3/O2 mixture into the in port of the apparatus and it bubbles into the liquid in the pot.. KEEP IN MIND the oxygen from the oxygen tank should still be flowing into the pot with the O3 bubbling through the liquid also (4) When the pot starts turning a little tint of blue then you are done. That blue tint is O3 building up in the pot cause the reaction is done. KEEP IN MIND UNLESS YOU HAVE A REAL INDUSTRIAL OZONE GENERATOR THE POT MAY NEVER TURN BLUE EVEN IF ALL THE STYRENE REACTED ALREADY CAUSE THEY DO NOT REALLY PRODUCE ANY OZONE. I mean they do but not much
(5) Turn off the ozone generator and let the O2 still go for 15 to 20 minutes so it can flush out any unreacted O3 that is in the pot still. Do not flush the system out with nitrogen cause it will explode (6) When you are done check the pot with KI paper to make sure there is no O3 still in there. Because these ozonides are peroxides and they are the MOST EXPLOSIVE peroxides that exist. SO YOU DO NOT WANT TO DRY TO EVAPORATE EVERYTHING TOTALLY IF THERE ARE STILL PEROXIDES IN THERE OR YOU WILL BLOW UP. So just check with KI paper. If it turns black then there is more O3 in there so destroy that before you try to extract and boil down to total dryness. (7)Now you can do your reductive work up with zinc dust or DMS or NaHCO3 and extract and purify (8) Never use rubber or plastic in your system. Ozone will eat it up. That includes and tubing (9) You should have a blast shield around the pot when doing the ozonolysis. (10) NEVER USE ETHERS FOR THE SOLVENT IN AN OZONOLYSIS REACTION.
Every word of this is really, really good advice. Sincerely. Ozone doesn't play around, especially at scale~!
Ether and ozone? Yikes
"Cherries and puke" :) :) reminds me why I first got into chemistry when I was a kid.
The diffraction in the styrene is beautiful.... I'd like to make some just to look at and say "oooh... pretty!"
Could have get polarizing filter perhaps... Stuff may look pretty.
I've done this before too. You need to titrate your Ozone generator but to be honest just looking at it, we are talking milligrams per hour unfortunately. No offense, I have a Chinese eBay one that titrated out at 5 milligrams using dry air.
You need to vacuum distill it to avoid turning it all into benzoic acid, use a cow-adapter.
Also, you can make the bisulfite adduct out of the reaction soup using sodium or potassium bisulfite and separate off the gooey crystals of benzaldehyde, wash with toluene, filter, and break up the adduct with Dilute HCl or NaOH solution to recover the Benzaldehyde.
SUGGESTIONS........ (1) I know they use MeOH as a solvent in many directions. And i know MeOH is a polar protic solvent. But i have NEVER heard of using acetone or especially water as the solvent. IN MY OPINION you should use a NONpolar APROTIC solvent like DCM or tetrachloromethane or benzene. The less polar the solvent is then the better the solvent. Protons from the water should not be flying around in the pot when you are making ozone and molozinides(organic cyclic ozonides) and carbonyl oxides and ozonide anions. All those things i just mentioned have oxygens which have lone pair electrons and i do not see how having protons all over the place will help with the ozonolysis.
(2) When you bubble in the O3 you are making a couple intermediates but it will stop at the trioxolane (ozonide). So when you get done bubbling in the O3 you have ZERO benzaldehyde at that point. Depending on what you want to make will determine the work up. For benzaldehyde the work up would be reductive. For the reductive work up you could use zinc dust or DMS or thiourea and many more INCLUDING NaHCO3.................Remember you got done and poured a little out of the pot in to water to see if it would float or sink and you thought you had no product. So then you wanted to neutralize the benzoic acid you made from over oxidation. SO YOU ADDED NaHCO3 AND HEATED IT AND THEN ALL OF THE SUDDEN THERE WAS GLOBUALS OF BENZALDEHYDE. Well that is because you finally did the reductive work up to turn the ozonide into the aldehyde by adding the NaHCO3.
Next post i have some suggestions about safety. Not for micro reaction like in the video but if you scale it up a little bit or have a better ozone generator than in the video
Try oxidizing styrene to phenylacetaldehyde with peroxyacetic acid or performic acid. And then distill the phenylacetaldehyde(maybe flush the flask with nitrogen first). I don't know if the phenylacetaldehyde would overoxidize to phenylacetic acid.
Sounds interesting, perhaps in future I may do this. I am still setting up lab and have still limited access to chemicals, hence the pyrolysis step.
No es económica ,pero es importante saberlo ante lo complicado de los suministros ,muchas gracias por tu vídeo .
Please do more ozonolysis reactions, these are very interesting
Thanks, probably won't do one anytime soon. They are interesting, but from this experiment I got impression that they work in similar way to organic electrochemistry - you can get high yields in some cases with certain amounts and after you sell your soul to satan :) but that's org chemistry summarized I would say...
@@IlusysSystems sell your soul to satan?
Hey, really awesome videos! What kind of digital Thermometer is this? I would love to have something like this but just can't find it, thx!
i have two suggestion: 1 use an aquarium porous stone immersed in te solution to increase de surface area between gas and liquid phases. 2 ad Thiourea to the solution , will help to reduce over oxidation and to convert byproduct in to haldehyde.
lots of interesting suggestions, but the truth is, if you are doing this purely for interest, I guess that's fine, BUT, if you are expecting anything over 1ml of pure Benzaldehyde, the ozone method will always disappoint you. The amount of ozone produced, on a molar basis, is pitiful even from decent ozone generators, that and the dilution ratios needed to suppress over oxidation make it not practical, if you want to actually get some decent yield of the aldehyde, a pretty decent and fool proof method is the oxidation of benzyl alcohol by dil. nitric acid with a little nitrite in there, works brilliantly.The benzyl alcohol can be had from food grade preservatives, just distill it out, the nitrite can be made from nitrate, and the nitric is easy to buy
This isn't really helpful, but even though the vapor pressure of benzaldehyde is low, the amount of gas you were running through it for that amount of time was probably enough to evaporate most of it as quickly as you were making it. I've had this problem when chlorinating hydrocarbons where the huge amount of HCl produced is enough to carry away most of the product. For me and for what I was doing, a dry ice gas trap worked. That probably wouldn't work very well for you though without at least a gas drier before the ozone generator or you'll get nothing but water ice.
and also decrease the temperature 0 c°C is good but -20 °C is better
Yay! This needs to be perfected. Amphetamines from Styrofoam 😊 you can be a billionaire if you can make a machine that takes Styrofoam in one end and dumps amphetamine out the other end 😊 that's what I call RECYCLING! 😆
Very beautifull video, pratical chemistry video like yours are very necessary. But i suggest tu use elementar zinc like sacrifical species (at the end you'll have ZnO, benzaldehyde and formaldehyde).
A long story short it is not enough to make ozone react with styrene to obtain benzaldehyde.
If you need more details write me.
I have found another OTC way to benzaldehyde, so I won't be revisiting this anytime soon probably, but will keep your suggestion in mind
Arent you forming the ozonide? That would require reduction in order to get benzaldehyde.
According to paper (should be in description), that is converted to benzaldehyde rather quickly which seemed to be the case.
I did not test for ozonides though, don't have knowledge/equipment for that.
2:13
Add some MEK peroxide to the styrene and see if it polymerizes. 😀
Hello bro! Ozonolysis of benzene. The product is glyoxylic acid. USSR chem book.
Sheesh man, working with styrene, ozone and possibly even TATP, all in one video
test on H2O2 was negative which shouldn't be really, but yeah I left the area when evaporating acetone for first few attempts.
Very drôle; good video.
Smells like...diluted tar. Haha :) nice video, thank you!
Piperine next maybe? 😅
I would love to make some piperonal. Wanted to explore chemplayer's workup, but didn't have oxidizers he used. So I made some in order of milligrams, but man, the smell!!!
It was very interesting but not economical!
Hi, you must be new here :)
@@IlusysSystems Yes, I have been following you for about 3 months.
Good luck and keep going strong 💪
@@h.m6316 Thx for support. Thing with this chemical is, that in most countries, buying it can place you on watchlist, and in some you can't buy it at all, which sucks.
You could produce more benzaldehyde and convert it to Salicylic acid and then into aspirin
@@coolcat_vlogs69 My target is benzil (and benzaldehyde for sake of it). I think NurdRage did aspirin? not sure. He did some some looong pathway pharma stuff.
I am sorry man, but that is a failed experiment. You should look better proper literature and repeat the experiment. The idea is in theory very useful and interesting.