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Making Benzaldehyde From Cinnamon Oil
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- Опубликовано: 19 авг 2016
- Today we are carrying out a super inefficient synthesis of benzaldehyde. This is a cool example of the Retro-Aldol reaction. This really is not a great way to get benzaldehyde though, and it is mostly just for educational purposes.
Chemplayer Video: • Video
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Nile talks about lab safety: • Chemistry is dangerous.
nigel: has an entire labfull of fancy chem equipment
also nigel: doesnt have a fucking *spoon*
"Oh yeah, I didn't have a spoon lying around anywhere, but I totally have broken plungers for days."
I wanted thank you, your videos have really helped me in my practical exams.
No problem!
U mean meth makin
@@NileRed op
I've always found it interesting that you can make minor modifications to aromatic, fragrant compounds and completely change their aroma such as is done here.....even more interesting is the way that isomerism and particularly chirality can make huge changes as with chiral isomers of carvone which can either smell like spearmint or caraway depending on their L or D form.
My favorite example of the huge changes that come about due to isomerism is the racemates levomethorphan and dextromethorphan. Levomethorphan is a potent opiod, several times more potent than morphine. Dextromethorphan, though? No opiod activity, it’s actually the active ingredient in the over-the-counter cough syrup Robitussin. I think it’s quite incredible, honestly. The left-handed isomer could kill you with a couple dozen milligrams, and the right-handed one is sold every day for maybe 20 bucks per gram. Chemistry can be wild.
My favorite is mono-nitrotoluene to toluidine. It goes from a pleasant leather polish scent to horse manure or burning rubber. Lol
I recommend a survivalist series, an apocalypse simulation where you get useful chemicals from common goods we can find while scavenging houses.
TEACH US HOW TO DEFEND AGAINST THE ZOMBIES!
Hey, thats pretty good!
Best idea so far
+Yentrilax you clearly don't like anything fun
wait did you just told him to kill himself? wow just wow
Dolan Duck It's the internet, buddy, get over it
That 5 liter beaker made me laugh at the size of it when you picked it up. Didn't look that big in other shots and I wasn't thinking it would be that big
-What a tedious synthesis! :D Extractions are my favorite workup procedure, though.
Well done as always! And I admire how you explicitly covered the mechanism.
This is very not tedious as far as organic synthesis goes. It's just mix, leave for 8 hours, then purify.
ooh, that smooth 60fps footage. Patreon money well spent?
Injecting steam from an independent source would be best.Acetaldehyde will boil away and benzaldehyde is far more steam volatile than cinnamaldehyde.You also could reflux for 5-6 hours and keep the condenser water at 30Celsius(not the usual ice cold water) as acetaldehyde boils around 20C and will exit out of the condenser top! LeChatlier idea is by removing acetaldehyde you drive the reverse aldol reaction to make more benzaldehyde!
You said your beaker was 5 liters, but the sheer scale of that only became clear to me at 8:30. That is one massive beaker!
I wish I only did chemistry with giant glassware. Then I'd look like a tiny man doing normal sized chemistry.
I don't know if you intend to be as humorous as you are but you have me cracking up through most of your videos. You have that kind of dry kind of witty humor that probably goes unnoticed by some people.
I'm curious, what is the blue bottle experiment?
And I would love to see a Q&A video, caffeine total synth, trimethylamine, and cyclohexanone oxime. So, I put my vote in for those next.
Could you have used DCM to remove the fine suspension of oil from the distillate, somewhat like you did in another video?
Me coming to relax for a bit while studying for the MCAT just to see the retro-aldol reaction again
You could make benzaldehyde by toluene oxidation, or chlorination/hydrolysis. it gives the useful benzyl alcohol as a side product and some trichlorbenzene, which can be used for dehydration of compounds or be turned into benzoic acid to use as benzene precursor.
Essentially turning toluene into 3 useful, less common chems in the lab
thanks he has a video of that too but it's private fucking sod payed to be a Patreon for private videos. what a rip off
Yes, I know the manganese method, but I wonder if ozone would work 😁
Really looking forward to the Caffeine synthesis. Alkaloids are awesome.
This gave me flashbacks to a chemistry class some 30 years ago. We were tasked with producing benzoic acid, and were divided into 6 lab groups. I don't recall what chemical was the starting point, but I do remember that the reaction involved boiling a solution, and that the chemical transitioned through benzaldehyde on its way to benzoic acid. So we were in a fairly small chemistry lab with six flasks of boiling benzaldehyde (almond essence), and well, let's just say the air got a little... dense. I don't think any of us craved marzipan for a while after that 😀
+NileRed Cool video! In the first step of the mechanism why does the hydroxide ion do a conjugate addition instead of attack the carbonyl directly? I though hard nucleophiles such as hydroxide prefer 1,2 over 1,4 additions.
Nile, you should do a lab/setup tour, that would be really neat
The Simple Distillation set up is perfect
I think using a Dean-Stark trap for steam distillation is a better idea than distilling four liters of water. Why didn't you use distilled water from the receiver to replenish the level in the flask?
NileRed you should link videos to other experiments that involve the reagents that are used in this video and so-on. :)
Hello Nile Red , nice video.
Do you think you'd be able to make Formaldehyde, or is that too dangerous to try?
what's the advantage of using ammoniumpersulfate over PCC for the oxidation?
reflux is just distillation without boiling something away?
so, in essence, just the phase change from liquid-gas back to liquid produces the Benzaldehyde?
Any thoughts on how one might recover the acetaldehyde, as well?
It's been a long time since I watched an old NileRed video.
"I didn't use organic solvents to be environmentally friendly." from the man who makes his FAVORITE CARCINOGEN.
What if you dripped the oil to the boiling water instead at a rate that eventually matches your distillate rate?
you should of steam distilled some cinnamon bark previously and so hopefully you would have had some higher quality oil to work with and hence get a better yield of benzaldehyde :)
Would Potassium carbonate work better since it is a stronger base?
Is the resulting benzaldehyde good grade? How can I make pure food grade benzaldehyde for cooking?
Since the reaction depends on the presence of hydroxide (OH-) ions, wouldn't it be better to use NaOH instead of Na2CO3 ?
NaCO3 generates small concentrations of OH. Using something like NaOH would probably drive the reaction to the left. Sorta like allylic bromination. A little bromine leads to radical addition, a lot leads to bromination of the double bond
I have one question because I have been clueless. I recently tried recrystallizing some KNO3 I bought online to try and grow some beautiful nitrate crystals, and after some time of boiling there was some left undissolved. I believe this was not KNO3 and had a much darker color like wet sand. I had originally tried dissolving it in smaller batches in a beaker, but it would start making this loud noise and shaking. I think it may be what is called "Bumping", but I've never heard anyone explain what it is except that boiling chips are used to prevent it. If you could I would really appreciate you opinion on the matter and just wanted to say keep up the amazing videos!
Bumping is caused by pockets of solution being superheated (above the boiling point) because there aren't enough bubble nucleation sites where the pocket is. Eventually a bubble will form and it will grow huge very quickly because of the high vapor pressure of the fluid being greater than atmospheric pressure pressing down on the solution. The bubble grows so quickly that it makes a mini explosion that often throws liquid out of the container. Boiling chips provide a surface with lots of irregularities so bubbles form all the time and they can grow before the solution gets superheated. That way they grow slowly, extract heat during the phase change from liquid to gas, and then rise to the surface gently and release the gas and the heat along with it.
Ashton Callender some potassium nitrate scores contain small amounts of sand as an I purity. I have performed that exact same expirement growing kno3 crystals. except I used stump remover and recrystalize it 1st, filtered it hot and let the crystals fall out. I did that with the whole batch. I then dried it out and stored it to use as needed to grow crystals and poor man's aqua reiga, etc. but that happens. I beleave it can be mined or made. depending on the score it may have slight contaminants.
Isn't acetaldehyde the chemical made in the liver from alcohol that causes the feeling of a hangover?
I have a Question.
The common houshold ethanol where I live is denatured with methyl ethyl ketone. It's virtually impossible to remove it via distillation. Could you force the MEK to undergo an aldol reaction to change the boiling point and then distill off the pure ethanol?
Do you know what the percentage is? It might be possible to polymerize it with a very small amount of base. I am not sure though.
I could have sworn you had a video synthesizing safrole
i don't think he did. i think he had another video about synthesising benzaldehyde using chromyl chloride though
What did the cinnamon oil smell like? Did it smell like cinnamon candy, or was it closer to cloves? Cinnamon leaf oil is actually mostly eugenol, and so if what you had was leaf oil, it would have had a strong clove aroma.
To me it just smelled like cinnamon candy
So... Would yo have a higher yield of benzaldehyde from the oil of the leaf or bark of cinnamon oil? You kinda confused me at the end there. From what I got from it was that if you used the cinnamon oil from the leaf that has %10 you would get a better yield. Please correct me if I'm wrong.
Hello everybody I would like to know if it is possible to synthesize (Bu4N+•HSO3−) from TBAB.
very nice
Teaching people how to make a P2P precursor from spices. This is why old youtube was awesome ! Fuck censorship
What exactly is p2p😅
@@xij3505 phenyl-2-propanone
Hey, Nile Red, sorry for the unrelated question on the video, but did you remove your mercury fulminate video? P.S.the videos look a lot better in 60 FPS.
I think RUclips removed it.
How much does all this distillation equipment cost? I have a lot of glassware, a butane burner, crucible, etc, but I'm thinking about buying a distillation setup. The only chemicals I really have is some semi-pure sodium acetate I made a few years ago, sodium bisulfate, acetone, and a few other things. I'm thinking about getting into more complex reactions since I understand safety, how to handle acids and very alkaline materials, and I know a bit about chemistry (although I am mainly a computer science person).
nurdrage has a link in his recent videos to a glassware supplier that has pricing info and there's also a discount code in the description
hope that'll give you an idea about pricing, then there's always eBay but then you have to be careful to get the real deal
Thanks! I'm thinking about inorganic chemistry as a minor. I just love to explore chemical reactions. I'm majoring in Computer science though. Maybe I could make some cool apps to help with chemistry.
There are some apps that are quite good but others that just suck so do try them out and see if you can improve! A NMR and IR identification app would be awesome
I have lots of cheap made in China glassware bought on ebay, it works fine for me, have broken only one flask until now.
Vevor has a really good deal on a 32 piece glassware set for 104$
I just figured out that I have a cinnamaldehyde allergy, and I was wondering - does the cooking of it break it down and make it so different that I wouldn't be allergic? Like... the cinnamaldehyde content in tomatoes. When I eat raw tomatoes, my face flushes burning red. Cooked tomatoes, much less of a reaction. Is this my imagination? Or true?
What happened to your plunger?
wouldnt it be easier to centerfuge it?
Can you please make Formaldehyde?
That’s just a dehyde with a fancy hat and monocle
Dehydration of ethanol to ethene, followed by oxidative cleavage of the double bond to 2 equivalents of formaldehyde
Or just buy it from Walmart, it's called Campa-Chem. Not very pure, but it seems to work for a lot of home chemistry stuff.
@@jhyland87 exactly, taste just as good to me.
@@BAgodmode lmaoooo
what is this used for ???
where are you getting your distilled water? are you distil it your self?
I just buy it from the grocery store
I miss these longer videos he use to make.
I think his videos are longest nowadays actually. Latest video was something like 47 minutes
You know this video is like 5 years old right
I think that the Distinct change in smell from the beginning to the end is (expecting some scientific explanation) Pretty cool. (Oh, ok... Thought he was gonna geek out or something for a little bit :)
Do a lab tour
Just a curious question: how does the stirring pill works exactly?
There is a spinning magnet in the plate below!
NileRed thanks. Awesome video as always, keep them coming.
***** thanks man
like a mexican jumping bean
why not using pure cinnamaldehyde u recovered at the end directly with water and sodium carbonate
What are these products used for?
making meth unironically
what is the name of the degree that you currently have (or the one that you are working on) because i watch every single one of your videos because this stuff just fascinates me and i would love to work with chemistry in the future and get a degree with it. Are alot of your videos and reactions based on organic chemistry or is all of this just like general chemistry. I would really appreciate if you could reply/pm me.
I dont know nile's qualifications. But im in the 3rd year of my bachleor course of chemistry. we dont do everything Nile does( because he is a pro and awesome) but if you do Masters in Chemistry and go into research you will for sure work on your own
I have a BSc in Biochemistry and about 7 months of research as a chemistry grad student. Most of the what I do is organic chemistry, but there is some inorganic and general chemistry sprinkled in.
+NileRed
can you come up with a process to extract myristicin from nutmeg as a subscriber if yours i would highly appreciate it
Isn't Acetaldehyde the hangover chemical?
cgarzs
Yes.
What kind of grease do you use for your joints Nile ?
I'll tell you what's amazing and what I use. Dow's High Vacuum Grease. It's silicone grease. It REALLY holds up well under high vacuum because of its low volatility. It keeps its normal viscosity at very low and very high temps -40 C up to over 200 C. It's pretty chemical resistant as well obviously so you don't have to worry about it being attacked or dripping into your flask and messing with a reaction.
I can tell you that I never have a problem with losing vacuum even over a course of a very long distillation or reaction. I also use it to seal up my vacuum desiccator and it will hold a vacuum steady for longer than I've ever tested.
r.ebay.com/Fr3a0b
kjpmi Thanks kjpmi really helpt me out.
+kjpmi you sound like an info Comercial
aajjeee I like it, so sue me...
it works so much better than vaseline or anything else I've used.
Philip Mastny you're welcome. It's not super cheap like vaseline but a tube last for a long time and it really works so much better.
this guy will be the next Breaking bad show
A couple of connected suggestions I (and suspect many others) would like to see:
_1)_ Nicotine from raw Nicotiana leaves (if possible).
_2)_ Nicotine from cured tobacco.
Please :-)
Preferably methods possible without complex, high end lab equipment.
I just want to imagine what it must've been like buying a 5-liter beaker.
You hope and pray that it doesn't come in broken. Then you wonder why you bought it when you may only use it a handful of times.
Separating benzaldehyde, cinnamaldehyde and acetaldehyde is so challenging because they all are liquid
awsome
RUclips poll recommend me this video 😅
would a fractionating column reduced the amount of oily water you collected during distillation?
Actually, it should, thing is, you cant connect it because of the thermometer in the distillation apparatus
+Nitro why couldn't the column be placed between the RBflask and the sideways adapter?
Dalitas D
Because you have to stick the thermometer somwhere, but you can always use 2 or more necked RBFlasks
+Nitro wait what, the thermometer can be at the top of the column right or are we thinking about different set ups
Dalitas D
We probably are
How do you get the perfect black background?
It's not always perfect, but it has to do with lighting! It would be a lot better if I got a darker and better backdrop
Let’s see if this one will get me to bed
If Gene Takovic was in breaking bad:
It's called a centrifuge, on the fist go around.
no links down below...
almond oil is benzylaldehyde???? i had bottle of it and it didn't smell like almond so i got rid of it -.-
Most smells are pretty horrid in large quantities; Skatole, for example, smells sweet like flowers until you smell large quantities, then it smells like literal shit.
+Hillebrand1 oh you got me there...i forgott that...thx
i'll messure the PH if i find some again
Can you link to the ChemPlayer video? Also rip in peaces ChemPlayer :(
I am gonna miss them. Their concept was ingenious.
Oh yeah, I forgot. Ill do that
RIP chemplayer :((((((((
When will you be releasing your video on making Benzaldehyde from Bitter almond oil?
I would be willing to think that is the easiest method and I just can't wait any longer for the video to be released! :P
but... does it smell good?
It looks like chinsee soup flavouring oil :D
Cinnamaldehyde is such a nice chemical :D
Fun fact: after drinking ethanol gets decomposed into acetaldehyde which is the chemical that causes hangover
I'm here waiting for the Nitrous Oxide video.....
can you start from cinnamon bark and extract the oil from it?
Yes, you could do a steam distillation to get the cinnamaldehyde out of the cinnamon, but that takes an awful lot of time and the yield is relatively small. It smells great though.
You have to be a big big manufacturer to be able to extract significant amounts of essential oil. In home lab type of enviroment you probably need 5-10 kg's of bark.
Undead Gaddafi I love how you ended it with the "good smell" comment although you just illustrated how long and cumbersome is the process. you are a cup-half-full type :)
Batuhan Bulguroğlu I didn't realize how much bark would be required to do it. Just wow.
Ibrahim Ali Haha yeah, I did it myself once, the whole process was annoying, but all the glassware smelled like cinnamon for weeks.
Can you make a chemical for me to not feel depressed
What happened to 1-Octan-3-ol?
he is probably too afraid to have a mosquito swarm in his lab. hahahahhaha
Batuhan Bulguroğlu But it's for the sake of science ):
It will be posted next
OOOOOOOH THE LORD HATH SPOKEN
Have you thought about synthesising humans? I hear they're a mosquito attractant also
I went from the skatole video to this. RUclips is trying to.....cleanse the palette, I guess. 🤷♀️
Next video will be: making chocolate from a stone
new camera again ? 60p doent run well on my laptop :(
There probably is an issue about your laptops playback capabilities. All the settings works just fine on my. Be sure to have adobe flash's final version on your pc.
Flash? RUclips has been using HTML5 video for ages now (unless you have an ancient browser, in which case it still serves Flash)
My bad. Brain is on auto-pilot. Ok, gotta admit that was humiliating. :D
Please revisit this video. ^_^
So.. we can turn polystyrene to cinnamaldehyde then to benzaldehyde? 😂
Man, Nile, take care of your equipment! That broken beaker at 9:10 made me cringe so hard!
+Yentrilax 👌🏻
It still works, so why throw it out? I fixed it with a blowtorch and it has been working well! I do have other 1L beakers though that aren't broken
NileRed The problem is that its broken, not that youre, using it. Besides that, fixed it with a blowtorch? What kind of sorcery is that? Did you just smooth the edges with the blowtorch?
*****
I watched the chloroform video when it came out, which means, a long time ago. I didnt remember the "hole". Ill give it another watch.
Make a chemical rap
Yo bro I heard you like carbon bonds... So I carboned you're carbon with, you guessed it you have more carbon lol
How can one extract the Myristicin Myristin and Elmicin from nutmegs or nutmeg oil. The 3 main alkaloids found in nutmeg. you shoud do a video on that. it may require carefull partial distillation with a 3 way flask at varying temperatures
I am going to have to get you a lab spoon, a chemist not having a lab spoon is akin to a mechanic not having a slot screw driver. 🤣
yaay more chemistry :D
How much did that cinnamon oil cost you?
I got it super cheap. Maybe $15 USD?
Mmmmm......
I would guess that your yield is low. I would think that you're losing product to a competing SN1 reaction where benzaldehyde reacts with any of the other things in the single pot (water and cinnamaldehyde main but nearly everything in that flask can react...).
If you increase the temperature above the boiling point of benzaldehyde in the main reaction vessel you could remove it before it had a chance to react with other things. Maybe add a fractional distillation rig to allow the benzaldehyde to "hide" from the other products/reactants.
Finally, you should chill your product before trying to separate it. You can actually purify the benzaldehyde out from the cinnamaldehyde and water based solely on their freezing points, but it is slower. Still simply chilling the solution would reduce some other things that were obviously a problem. I think you were getting that cloudy color because your were getting hemiacetal formation.
Again why the distilled water and Na2C03??? Can one use lye? Or MGS04? Lr KOH???? U add water woth drying agent to remove water? With sep funnel? Is this correct
I think Na2CO3 was used because the reaction must stay between ~Ph 11 - 13 for maximizing the desired product. Na2CO3 is a weaker base and has some additional pluses: low solubility in water would prevent over concentration and thus going above Ph14. Also for one pot steam distillations having a salt saturated water source for the steam helps for many reasons. BUT, i wouldn't be surprised if the low yield was also caused by the choice of base. Maybe just a pinch of a hydroxide would have made all of the difference?
I'm thinking of doing a retroaldol on this and then re-condensing it to get a phenyl allyl with an interestingly positioned keton 😂
The facility were only going to suspend you for shaking it too vigorously???
That's pretty cool of them, really.. I mean, i (briefly) attended, (Odessa Tx.) Permian High School (Friday night lights) gotta say, super snooty teachers; Zero tolerance anything really but ESPECIALLY when it came to shaking it, regardless of vigor used.
Expulsion without exception...
Ask me how I know. 🤭
I am allergic to this chemical!
what are stir bars usually made of?
never mind I remembered about Google haha
Usually Steel coated with Teflon.
holy 720p60fps club, batman.