Making Cinnamic Acid
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- Опубликовано: 10 сен 2024
- Today we make some Trans-cinnamic acid from benzaldehyde and malonic acid. The reaction is called the Verley-Doebner modification of the Knoevenagel Condensation.
The classic Knoevenagel Condensation is similar to the Aldol Condensation
Prep that I followed: www.chemistry.m...
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Nile talks about lab safety: • Chemistry is dangerous.
Nile's coming through with another top hit "Generic Timelapse Song 1" and it's honestly one of my favs
lmfao yeah same
Definitely a banger!
The Bob Ross of chemistry.
Aaaaaaand we'll just put a happy little moiety right there.
Wayne Moore
I love you XD
The only issue is a "happy accident" goes boom
@@elephystry who is Wayne Moore?
@@DereliqueMahBAWLS I’m sure I would remember after three years.
Me: Talk dirty to me babe
Nile: _Decarboxilation_
carboxylation.
Hydrogenation
Distilled water.
Esterification
I don't know why but this made me laugh so hard that my mom screamed from the other room are you okay
Beautiful timelapse! Sometimes I forget that this really looks like pure magic, some crystals look like universes floating around :)
Crystallizations are always mesmerizing for me. Especially the ones that grow nice and long crystals
@@NileRed you like it nice and long eh 👀
@@ParadoxDetected bruh
@@NileRed Hey Nile, would you ever think of remaking this video? Cinnamate can be devirved from cinnamon oil apparently, and I think that would be a co twist - turning cinnamon into cinnamic acid or something like that
after watching a whole bunch of NileGreen this is very refreshing and nice to watch and follow. I like this classic chemistry vids from Nileboi
Nile, I just wanted to say thanks. I got into your videos a long while ago, and, because of them, I was influenced into choosing biochemistry over a typical bio-premed track. After working with organic chemistry and all that jazz, I've got to say, I love chemistry so much. I would have never known without you bud.
0:22 "were gonna be using the very dope modification of the nova bagle condensation"
Nile! I love when you explain all the reactions!
thanks! :)
10:28
NileRed: uses thermometer to stir mixture
Every chemistry teacher: You weren’t supposed to do that.
We ALL do it
Those who can, do. Those who cannot, teach.
@@GrassPossum Those who cannot teach... teach gym.
Verley-Doebner modification of the Knoevenagel Condensation sounds like something they'd make up to sound scientific on Doctor Who or Star Trek.
The last time I decarboxylated it was in the oven at 230° F for 45 minutes... umm... nevermind.
#reportedtothepolice
NileRed #snitch
Share some with me!
@@elephystry wait a minute! you changed your name!
caspar valentine I did!
Those crystals are really beautiful Nile. Nice "generic time lapse music." :)
Your videos just keep getting better and better. I was impressed by the presentation of the reaction's mechanism (4:48). Very professionally done.
Started watching NileRed years ago but I just passed my organic chemistry lab and exam at uni last week and the knoevenagel condensation was one of my faves to learn actually :D
The fact that there's both a trans- and cis- version of the acid makes for some great pun potential!!
Facts lol
tempted to use this video to come out someday
“i relate a lot to the chemical he makes in this” *attaches video link*
After you've made styrene, maybe you could make one about how to convert it back to benzene or other useful things? It would be a great way to recycle all of the styrofoam packaging from the glassware!
Wayne Moore
Extractions&Ire did a few lovely videos on converting soda bottles to benzene.
Did he made the styrene yet? Really want to see
Knoevenagel Condensator sounds like a magic device from Witcher.
He pronouced it completly wrong. Its spelled Knöwenagal (The letter ö doesnt exist in English)
Doctor Who: It DINGS when there's STUFF!
@@zillertalernazihass en.wikipedia.org/wiki/Emil_Knoevenagel
I could swear this was something present in cinnamon 😂🤣
cinnamaldehyde is
This synthesis is elegant because it avoids the passage through the ester!
You're videos never fail to entertain me and help me keep my mind off of anything and everything that could possibly be going wrong. Thank you and keep up the great work!
3:20 I giggled when you said Dr. Seuss reaction. 😂😂 I also get a tingle down my spine when you recrystallize stuff. I feel like it’s snowing. 😍
Smh e-girl
You giggled? Are you 12...
chemistry... asmr?
I already watch these videos to fall asleep and the pleasant music at 9:37 really amplifies my sleepiness 🥱😴
you could make a time lapse album and get it published. i suggest giving the songs real names 😀
Are you telling me that Generic timelapse song #1 isn't a good and real name? :(
idk about the branded beekers but depending on the price id be down for a labcoat
Same also spatula or tongs would also be cool
I got some of the beakers. They're pretty nice.
I am an organic chemistry student at the University of Oregon and I recently performed this reaction in lab. In our procedure we placed malonic acid, piperdine, benzaldehyde and ethanol in a reaction tube and heated in a microwave. Afterwards we acidified with HCl and vacuum filtered the product. I thought your procedure was extremely interesting and one I had not considered before. I was curious if there is anything interesting I might be able to make with my remaining cinnamic acid?
Esterification?
How did university work out?
Yay! A new NileRed video.
Professor proton is not real its sheldons hero
I would deadass buy a Nile red lab coat and wear it every single lab I have throughout my undergrad and graduate schooling, as well as if I secure a job teaching college level chemistry!!!
GREAT VIDEO. Can't wait till i am this far in the lab
You are amazingly good at explaining
Thanks!
ill take a beaker with your name on it, i would def become a top tier supporter. your the best out here brother
Thanks! :)
This one is really nice! Love to see those mechanisms! 😁
Whoose heart also stopped for a moment when he dropped the stirr bar right into the flask?
now can you vanillic acid. then make both vanillans and cinnamons alcohols?
The quality of your videos is outstanding. A video about cleaning and waste disposal would be interesting. Is the waste department asking questions and are you acting as a private individual?
I actually have a bunch of waste sitting around. It all needs to be disposed of eventually. I might have to pay a company
Hi nile, what about the synthesis of trans-3-Methyl-2-hexenoic acid (TMHA) the main contributor to armpit odor?
Ill look into it. Might be a little tough to make (depending on what the starting materials are)
I guess You could use pentanone and ethyl chloroacetate in Wittig reaction.
NileRed
Yeah Nile, it really seems like your thing. Get it done. ;)
@@ATFieldZenkaii
Why complicate your life with ethyl chloroacetate and a wittig reaction when you can just use practically the same reaction as this video?
Malonic acid+pentanone and you're done.
@@pietrotettamanti7239 I don't think that pentanone is electrophillic enough to react with malonic acid. This modification of Knoevenagel reaction works only with aldehydes, which are far more reactive than ketones. Classic Knoevenagel reaction might work, but it will probably lead into mixture of trans and cis isomers. In this case, Wittig reaction is slightly more selective. If you don't want to use quite nasty ethyl chloroacetate, then corresponding ylide is commercially available.
That's an interesting way of using beta-alanine
I am willing to see the Nylon video
Thank god we'll get at least one more video this month =P
One last will be posted tomorrow, but i made it in sept
I think it would be cool if you put together some branded chemistry starter kits
That would be the ideal in the future
NileRed Nile my dude if you put together a starter kit and did a bunch of videos of stuff you can do with it, I'm fucking for h*cking sure buying that. If I had kids I'd be buying them each a set, too.
could you try making PLA plastic (Polylactic acid)? That would fit in nicely with your polymer experiments!
I dont know why i enjoy listening to the nerd so much, but i have watched probably all of his videos more than once.
Very professionally done
this is a cinnamic masterpiece
I did it 2 months ago
Using the aldolic condesation
The lab coats should absolutely be make with the dye, Nile Red
10:08 Okay, that's an award winning song name.
man i miss these longer videos
All I've retained from your teachings is how to get anesthetic from anal lube, sodium hydroxide makes water hot, and how to make soap.
Could you do a video about experimenting with liquid oxygen?
joost00719 he already did
The discolouring in the Pyridine could be from additives to prevent its usage in drug production of PCP. Oxidising the Pyridine to Piperidine with Raney-Nickel.
I think the Beaker and Lab Coat ideas are really good ^ - ^
Can i use muriatic acid from cleaning agents instead of pure hydrochloric acid?
Did you ever get around to making that styrene?
thank you nile red for finding my origins.
Shouldn't you be wearing a labcoat while doing reactions?
I should be!
This dude is on a list
Your mom's contact list
I'd love to buy some lab equipment from you. I love your videos!
What can you do with this acid? How are the visuals and how long is the trip?
JOKE.
I'm actually curious what its uses are
Stefan Reich
Good one.
Ahaha its funny because drugs
@@chaz2985 YEAH
We actually had a lab in Orgo I where we brominated trans-cinnamic acid, interesting to see an unrelated video on it
I found a variant using ethanol instead of pyridin. Do you think that could work while using more Alinin?
Did you make that generic time lapse song, or just use it from somewhere? I really like it and would love to listen to more
YeSSSS Nile red beaker, I want one
Is cinnamaldehyde not a possible/more accessible precursor to cinnamic acid? Your cinnamaldehyde clock video was fun to watch, but it killed me to see so much cinnamaldehyde wasted. It took me almost ten hours to synthesize ~15mL.
Knoevenagel is pronounced "ka-noo-fin-aa-ghel", with a hard 'gh' (it's a Dutch name)
The stir bar is crazy
Can you make phenolic acid with the addition of benzoic acid?
You should try synthesizing some fancy organic dye. maybe coloring your labcoat with it or something?
Could you get aluminum from antiperspirants/deodorants?
Sounds like much more of a Cody'sLab's thing but yes please!
Probably way to little aluminium to get from those, though it might be possible it you get a lot of them, and find a relatively high yield (>80%) way of extraction.
HI @NileRed. May I ask if there's any reason you'd not use a heating mantle? All descriptions of the Knoevenagel I've come across describe use of a hotplate, or shallow oil bath. Is there a reason for this? I prefer a mantle for heating but find the reaction is slower than descriptions, although raising temperature has improved it. I wondered if the greater heat transfer from a mantle, to the distillation product, in my case toluene/water, (which doesn't make sense to me) is a problem. Doesn't make sense. The heat is intended to push the reaction, but can it be too much? Can it take too long? Is there any degradation of the product or reaction if greater time is taken to complete? ie; 24 hours instead of 5?
GREAT VIDEO.........(I can not believe it only took pyridine to make the enolate. .I need to make some of that malonic acid and ester and some ethyl acetoacetate
YES PLEASE!!!!, labcoats and beakers(maybe even more glassware)!!!!
I read the title as: "Cinematic Acid" and just thought "Damn okay this weekend gonna be good."
Can't use parkin reaction?
i loved it!
How did you get the malonic acid? I live in the in the US and there is a restriction unless you are a company through Fischer, sigma and spectrum to name a few.
Hi, I'm currently doing this, does it matter what kind of oil you use for the bath? I know it obviously isnt that important but imagine different oils get to different temperatures. What kind of oil do you use? Looks just like vegetable oil, or peanut.
What do you do for work? Surely you can get about any chem job you want with this channel as a reference!
where do you get the benzylaldehyde from
do you create these recipes or do you get them from somewhere? if so, where?
I scaled a procedure that I found online. I linked the prep that I followed in the description
I think that doing the Perkin reaction will be better.
Did you do H-NMR to see whether it's pure? You should filter the hot solution by doing a hot filtration then reduce the volume of the solution a bit when you are doing recrystallisation.
Can you make a video about how molar mass works? I know it's simple but it's something I could never quite get.
i suspect you have water in there; explaining the lower melting point. maybe keep it in a desiccator with p2o5 and a slight vacuum for a week or so; pretty sure you will get a higher melting sample (or don't if dryness isn't super important ;-) )
Do you think you can make ethylene oxide? Would be so cool if you succeeded.
Can we get a "white precipitate" counter?
Hey NileRed I would like to get into some home chemistry as a hobby but I don't know what starters supplies I should get. Could you tell me what starter supplies I should get?
you're so good at recording and doing your experiment. I bet you got A's in your chem high school because I failed chem
I actually got a 65% in my first semester in high school chemistry. In both physics and chem...
Hey man, I have a question:
Have any of these videos yielded you a paper or something like this? Or do you keep it informal?
What about Perkin's Condensation Nile?
why'd you take down the IR camera video?
How do you prevent cis-cinnamic acid from forming?
You take away its cis privilege and make it attend organic chemistry sensitivity training. LOL
@NileRed, should I do this to then concentrate trans-Cinnamyl Alchohol, or should I try another way? thanks!
I did this today in lab but i used piperidine instead of beta-alanine.
Do dimethyl mercury
Do you think that glycine would also do as a catalyst instead of the alanine?
Acid... Trippy, man.
Hi how I can manufacture the chemicals for sold purpose
Do you say you are Nile Red on your resume?
U Wot M8
"I have a very popular chemistry program on the web"
@@J.G.H. It depends on the job. Some forms of work having large internet following can be seen as problematic
I recently studied that when you have many conjugated double bonds in a molecule than it usually absorbs light and it's coulored (like a compound in cumin makes curry yellow). Then why is cinnamic acid white? it has 5 double bonds
yes you're right, there are 5 conjugated double bonds, but that isn't enough. carotene, which is coloured due to the presence of conjugated double bonds, has 11 of them
Just a minor thing, Knoevenagel is phonetically pronounced, according to my text speak is: nuvn ah gill.
I'm german and I can't even describe to you how it's meant to be pronounced.