How to extract Cinnamaldehyde from Cinnamon

[@dumi08]

5 years later still the best content around here! Keep going!

[@Klaus-Schwab_Dictator]

8 year now

[@SetTheCurve]

Until you watch the recent childish garbage

[@axe4770]

Now he owned a huge ass storage building filled to the brim with high tech lab equipments. During that time he still working in his dad’s garage, now look at him the difference is night and day.

[@axe4770]

@@SetTheCurve doing things professionally on a platform that is for entertainment isn’t gonna get you nowhere. Because of that childish stuffs now he owned a personal lab bigger than than your house.

[@NexusDNA]

Hey Nile! I made this extraction today; from 28g of cinnamon sticks the yield was half a ml of the aldehyde. It smells nice! It is a bit cloudy but I believe it is water suspension from the separation process (as I don't have a desiccant at hand).

[@NileRed]

Yeah ,it is very likely water that is present. Also, good job! I find it smells like very strong cinnamon gum :)

[@CharlesSnyder]

I bet your shop smelled pretty good for a while.

[@NileRed]

It sure did!

[@PaulaBean]

+Charles Snyder It smells like Xmas! ;-)

[@wumbology3109]

It's smells like smell.

[@sunnybowos266]

It smells like it smells like smell

[@MoMo-if3nh]

is it still smell good? 😂

[@hoggif]

You've really had the same style back in the garage. Your current lab is so much better but the content seems to have been there all the time. Well done. Keep it up!

[@NileRed]

I am not sure why, but it didn't separate out. I also did limonene which quickly separated out. I guess I could have left it out for a while and waited for it to separate.

[@juzeralirangwala3539]

You have posted video on separation of Limonene from orange peels ?

[@NileRed]

I will. It is the same process but the oil separates immediately and can just be pipettes off. Ill edit it and upload it eventually

[@juzeralirangwala3539]

Okay, will surely check it out whenever it is available

[@NileRed]

Those are two very different techniques with very different purposes!

[@NileRed]

christopher vester I think it is, but I didnt check.

[@anthonyvance8628]

Oh my, man you are a revolution in the youtube chem. Nice job. I love your videos and methods. Don't give up! :)

[@oceanjunkie5968]

His channel really is the best chemistry channel around. He doesn't pander, his commentary is A+ and not annoying, great filming, great explaining, he lists reactants, quantities, and chemical equations. His experiments also look very neat and not half-assed in someone's back yard like some more popular chemistry channels. One of the most admirable things is that he doesn't only do flashy, explosive, or crazy experiments, he has a lot of variety.

[@NileRed]

Ocean Junkie Thanks!

[@oceanjunkie5968]

Nile Red Your welcome!

[@honestly108]

Government: "What do you need this lab equipment for?" "Extracting Cinnamaldehyde from Cinnamon" DEA:" Sounds like meth to me" "Wat" FBI: "Sounds like explosives to me"

[@CoolKoon]

+The Soviet Nikita Fortunately you don't have to ask any government agency when you buy lab equipment.

[@maxpenrose9480]

The Democratic People's Republic of Nikita hey this is merica budy

[@CoolKoon]

+max penrose Just wait until the new 'murican regime bans the purchase of lab equipment for some BS reason....

[@markmccormack7206]

think of the children

[@argenteus8314]

+CoolKoon Some states actually do ban that.

[@PaulaBean]

Nice video, I especially like the videos which are on the border of chemistry and cooking/food science. Maybe you could also do a peppermint oil extraction from peppermint plants? And vanillin from vanilla pods? And rose oil from roses (like they do in the perfume industry)?

[@NileRed]

+Paula Bean I do like extractions from natural things. The only issue with it is that it is generally not super clean. Meaning i cant really do chemistry with the product i get. Real vanilla extract has like 1000 chemicals in it, or something crazy.

[@richardnineteenfortyone7542]

You have 100% chemicals in YOU. Starting with dihydrogen monoxide. Remove too much of it it, and you will become very ill. But you can be cured by massive doses of homeopathic remedy.

[@mortemsteam]

richard nineteenfortyone what

[@Gizmo_-]

@mortem [steam] that dude is out there😂 thinking he can cure corona with essential oils😂

[@industrialadhesive6357]

Yes vanillin for "flavoring" he should also make safrole for "rootbeer"

[@geom4924]

0:07 “Damn that’s one awesome bong”

[@alil7896]

bong jokes are pretty common in orgo labs in my experience, people work with "awesome bong" devices there every day. I've known someone who had such a great connection to the glassblower at their university that the glassblower made them custom bongs in their free time.

[@qdog5921]

I thought you were doing this all at home?.How the hell did you have access to an NMR machine?

[@declanmercer2587]

He has said in the past that one of his friends have access to an NMR machine

[@cynthiabrogan9215]

Q Dog he pulled it out of his ass.

[@ScottyDumas]

My uni has an NMR machine. It's pretty cool!

[@joeallen9897]

He clearly distilled one from the Sri around him...

[@kristindonegan2021]

I've been watching for a few years, and tomorrow I am separating essential oils from spices in my college organic chemistry lab via steam distillation. Happy that I can finally put the knowledge I've gained from your videos into use! :D

[@ambhaiji]

the cinnamon saga goes wayyyyy back, damn.

[@JNT250]

Great video, this is really going to help for my chemistry research project! Thanks!

[@dr.mahbubdvmmba4212]

Its sooooo wholesome that the guy i watch for curiosity, fun topics nowadays is helping me withs exams now....

[@batman1169]

Not sure how I got here looking for instant pot recipes but fuck is this interesting!

[@nimabarandoust3751]

This is a great video. I'm not a chemist but interested in making essential oils. I watched your video many times and learned so many things. Thank's for sharing it.

[@Ghorda9]

you get essential oils from milking a snake.

[@pablopicasso6699]

You are a breath of (cinnamon) fresh air if the world of chemistry. Great work as usual ;-)

[@OJeyjunior]

Hey, first congrats for the channel :D, you often talk about the efficiency when you're making extractions, and I don't remember you ever using the Steam Distillation before... and I didn't find anything about it's efficiency, so I have to ask, how much (%) of it's essential oils you'd say was "lost" in this process (pretend nothing was lost for lack of surface area)

[@satchelfrost6531]

You should use this to make phenylpropargyl aldehyde (aka 3-phenyl-2-propynal). Why you ask? Because it's $250 per 5 grams and I thought it would be interesting to make something so expensive from cheap materials.

[@kkirschkk]

but he would most likely spend more money making it than it is worth

[@Swanke]

did you not read satchel's post? from CHEAP MATERIALS

[@JM-lh8rl]

Roarke Tollar But the materials used to extract it and the processes that are involved with doing so could increase the cost of the extraction

[@theophania6163]

Nice! My lab group used cinnamaldehyde in Orgo lab to synthesize imine compounds!

[@sagarkumbhar6348]

Hi

[@sagarkumbhar6348]

U know info about iodine value ,sap value of cinnamon oil

[@RaExpIn]

I had to do this distillation a few years ago, but I powdered the cinnamon and bubbled steam through the solution instead of heating the solution directly. The yield is always quite low. Nice Video :)

[@monmon1741]

Honestly this man can whip up whatever essential oils he pleases and it’s kinda not fair. When are you gunna sell them?

[@centrifugedestroyer2579]

We made cinnamaldehyde the aldol condensation way at university. The only trouble was that I nearly dropped the flask and spilled quite a lot of it all over myself. (Luckly I didnt need it anymore at this stage) Although my labcoat did its job, I smelled like cinnamon for the whole day. I know there are worse things, but it kind of sucks when eating something savoury. Best part of it was when a little kid on the train yelled: "Mommy, why does that woman smell so tasty?"

[@ibish9513]

Username checks out, I guess.

[@centrifugedestroyer2579]

@@ibish9513 Oh lol, I had completely forgotten about that comment. This brings back some fun memories

[@anderssorenson9998]

All I can think about is making a potentially lethal Atomic Fireball.

[@MrGreystone444]

it would be great if you make a tour showing your hole laboratory equipment and where you bought it :)

[@LokiScarletWasHere]

This may be an old video that Google had recommended I watch, but dammit, this video alone is worth a sub.

[@kacperslab2778]

Yeah Man you’re an artist

[@FuriousJean]

Impressive! Very good work!

[@petarugrina9627]

I like your videos. Keep on posting and dont give up. Btw, where you buy all equipment (glass stuff and chemicals)???

[@NileRed]

The chemicals are either made or purchased from ebay or other internet sources. The glassware is also from Ebay or other online sources.

[@sya_7489]

Damm this guy is pretty good, i bet he can turn Styrofoam into cinnamon flavorings

[@davidbush3759]

It took me years of watching you, but now I look at DCM and I know its dichloro methane c:

[@nirmalsuki]

Fun fact - more than 90% of the cinnamon produced in the world comes from one country. (My country, Sri Lanka)

[@ChamodDissanayake-ei3ok]

Very nice video. Is there anyone who knows how to do this in industrial scale?

[@hakemate]

Great videos Nile!! Quick question, how do you have access to an 1H-RMN ? Did you have to pay for the spectrum? If so, how expensive it is for each sample? Thanks!! I'll be arround.

[@NileRed]

+Alejandro Sánchez I was working in the lab, so when I took my own NMRs, I just threw an extra one in. I don't have access anymore unfortunately.

[@Kloashut]

@@NileRed Defenitely not comparable but using TLC may give you a clue about its purity as it's cheap and versatile.. Unfortunately it's only a qualitative analysis, even when using colouring sprays/baths

[@anthonyg1111]

Please correct me if I'm wrong. So @3:28, the bottom layer is DCM (which is polar, right?). Does that layer have a little bit of cinnamaldehyde in it?-> (and this is drained out each time?) The top layer is AQUEOUS; (white with the cinnamaldehyde OIL)?

[@ingevdf]

How do you know which extraction method to use? Water destillation vs Soxhlet, etc. Great video!

[@OF01975]

If the compounds are polar water can be used, non polar requires a different solvent

[@arjuna_1987]

if i add NaHSO3 to the water/oil emylsion (your distillat) will it help me to extract only aldehyde ?

[@sanchezzz69420]

you always have such amazing set up.

[@ashleycowen5104]

"When all of the DCM had been removed, the yellow oil which remained was transferred to a dram vial". How on earth did you get that little bit of oil out the bottom of the flask? Did you just hold the flask upside down for a really long time till the drops crept into the vial? Seems there would be lots of wasted oil on the inside of the flask! I'm considering using this method of recovering the DCM using a 1000ml round bottom flask, but I'm also thinking there may be a more efficient way to collect the oil once the DCM has been distilled. Any thoughts? Great video, btw! Very informative!

[@patricknagle4462]

You could use a pipette. Or just use your receiving flask for the next phase of synthesis once the dcm is removed and the flask maintains a constant weight.

[@scatteredvideos1]

When you get the cinnamaldehyde in solution, could you ad anhydrous magnesium sulfate to dry the solution and then vacuum filter the magnesium sulfate off? Just wondering if it would work

[@Renuclous]

Where do you perform those extractions and experiments, given that you have access to an NMR? Do you work/study at a university?

[@en2oh]

one of my undergrad Organic Labs was to make nicotine dipicrate. A really gross steam distillation of a big can of tobacco.. brings back found if not stinking memories :)

[@MSteamCSM]

Very good video! But why not just to wait for layer separation after the first distillation?

[@ThomasMacPac]

Hello. I am currently working on extracting cinnamaldehyde in a project and instead of using DCM or Ether I will be using ethyl acetate. Will it still work? Instead of 25.5g cinnamon I will use around 100g to compensate for maybe less separation from the water phase. I have also been wondering why exactly you use saturated sodiumchloride and calciumchloride what is it for?

[@Schatten2712]

+Thomas Jacobsen I'm going to try it tomorrow with ethyl acetate as well, I will post my results. Also I do believe that sodium chloride was used to drive water out of the DCM and the calcium chloride was the drying agent

[@GiGaHarrySfotter]

First of all, I really like your videos, pls continue to upload. But I am also pedantic, maybe dichloromethane is a good choise as extracting solvend, but very poor If you intend to use the extracted cinnamon oil in food. As you can see in 1H, at 5.3ppm , you have your solvent, and it's not a small molar quantity. Nobody should eat that, unless just to smell or taste a fracion of a drop. Since you like extraction, why you don't show up the menthol extraction and cristallization? I'm looking foward to watch more of your videos! Ciao!

[@Kloashut]

a more thourough drying will solve the problem however you are right here when using it as a foodgrade quality.

[@jonathoncliffbailey]

I love how Canadians say been.

[@mhcbon4606]

@NileREd ever thought about showing how to extract artemisinine ? Might be of interest for a bunch of people. hope you ll take a look.

[@andreasadi591]

dear NileRed. for sample of bark above 1kg-5kg, what is the best extraction method? thank you very much

[@MrAbbyandlilly]

cool work guy. can this method be used to extract oils from plants leaves etc, that do not ordinarily yield their oils on steam distillation?

[@Skatenlove24]

Awesome stuff 👍

[@compaqchemlab]

Aren't ground cinnamon to use better ?

[@mgord9518]

Is there a reason you needed to dissolve the product out of the water in DCM instead of just distilling off the water? Are the boiling temps just too similar?

[@piratewhoisquiet]

/watch?v=7g4e3dhtgjI

[@bulbinking]

For some reason artificial cinnimon flavoring has an after odor similar to saliva. Same thing with guava fruits. Do you know why this is?

[@zivatronicslab835]

Can you post a video on how to make cinnamaldehyde via an aldol condensation of benzaldehyde and acetaldehyde?

[@donzmilky5961]

Its weird watching the old videos again and hearing the 3rd person monologue.

[@oceanjunkie5968]

When you make substances with yields of just a few milliliters, is loss from the oil wetting the inside of the flask when transferring into the dram vial a concern?

[@NileRed]

yes, to do the transfer properly. you need to transfer as much as you can with a pipette or syringe and then wash the flask a few times using an appropriate solvent and pipette that out. Combine everything and then evaporate.

[@Niekomojo]

I wonder if this has been used for carcass preservation like formaldehyde.

[@danielaustin7643]

what other solvents can you use, could it be ethyl acetate?

[@NileRed]

+daniel austin Yeah i think that would work!

[@airinsalehuddin8037]

Why shouldn't there be foaming inside the bottom flask in distillation? 1:40

[@stichexsperament6263]

I know this is 3yrs later, but you don’t want the foam to foam over into the attachments.

[@RS-bi1pc]

I feel like this would be a good project to revisit nowadays.

[@nilnileer]

He did

[@sprg42]

Great video! I will try this, thanks!

[@gamerx112]

you can use the same method to extract Eugenol from Cloves. DCM can be used.

[@bigfootlive89]

I did this my organic chem class in ~2010

[@gamerx112]

@@bigfootlive89 yeah I learned it just recently in mine.

[@kentadran]

Would be cinnamon used in cooking works too?

[@chrischappell2072]

That glass ware would some pretty awesome bongs 😂😂💯

[@OF01975]

Lol thats what goes through my mind in organic chem labratory all them 10 litre flasks would be fire bongs

[@Kloashut]

Overkill, ruined quite some parties ;-)

[@BrickfallOfficial]

you should do a yellow powder experiment and investigate the reaction between oxidizing agents and poly-sulfides.

[@BrickfallOfficial]

coconut7joemanji Do not use chlorates.

[@natertater4024]

Nicotine from tobacco or the gum/vape juice.

[@SirGamestop]

This dude really got a proton nmr machine at his crib.

[@Stella-bu5bq]

if i want to increase the number of cinnamon to be use, does the volume of water and volume of dcm should be increased to?

[@saintofchelseathomascarlyl5713]

nilered why didnt you use the soxhlet extractor to extract the cinnenaldehyde?

[@1337sh337]

Do you know where i can buy flasks, beakers and other equipment? I live i Europe, and i have had no luck finding it

[@scatteredvideos1]

Ebay my man, I got most of my equipment there.

[@fakiirification]

I have to caution everyone looking for this stuff for a home lab, research local laws first. There is a war against science raging in some parts of the world, that lables home labs as drug labs without evidence of intent to create drugs, and could destroy your life. freedom is an illusion fed to us by the complicit media. Stay informed.

[@texannationalist5887]

if you're in europe there's a good chance the government won't let you

[@jakeevans7075]

yep my friends mum got arrested for buying an essential oil extracting set here in SA. As "It could be used to make drugs" blah blah blah.

[@JanJeronimus]

Don't know where you live in Europe. I know some places in the Netherlands where you can buy it. You can also order it from china e.g. on Aliexpress.

[@12andres24]

Why does proton A appear as a doublet? shouldn't it be a singlet as there are no adjacent hydrogens?

[@siberianstuntman3344]

I find even wwit ground cinnamon it doesn't bubble up that bad as long as you keep the oil bath at like 125c

[@ovalwingnut]

Wow! I'm not sure what I just watched but I am sure..... I'm IMPRESSED :) Thank you for the video

[@DaBoel]

Hello NileRed, I have a question, hoping you'll see this. For what purpose did you use the dcm in your vid? I don't know if this has already been answered. Is it to purify the extract? To break up the emulsion? I want to make lavender Oil and I fancy the dcm method, but some ppl tell me that it is unneccesary :/ Love your Channel, keep on the good work :)

[@harinachiappansubramanian9206]

I believe DCM is just to extract the cinnamaldehyde from the water layer so that it is highly soluble in it. Then to remove DCM u can also use a rotovap other than distillation which NileRed used

[@eriktorres2000]

can you dry it with NaSO4? instead of saturated sodium chloride solution??

[@simonjacobs8300]

Cool! Gut this is nog steam destillation right?

[@NileRed]

+Simon Jacobs It is and it isn't. True steam distillation involves shooting steam through the solution. This is just making the steam "in situ" which probably isn't as efficient, but still works well. We are still distilling off our product in the steam, but it isn't the true and classic technique.

[@zerowidth]

What kind of HNMR machine are you using? Can you talk about it in one of your videos?

[@LanzFamily]

If you used Ether instead of DCM could you use it as a flavouring?

[@thebiomajor5750]

I'm looking for the pin/clamp thing you've got around your glass valve on the sep funnel. Where did you get that, and what is it called, please? Love your videos btw. : )

[@MrAwawe]

is this edible chem?

[@samuelbonne4047]

hey, what's the frequency of the NMR you are using? Is this a benchtop NMR?

[@eggyolk5]

Why will powdered cinnamon possibly form more foam? How does the foam form?

[@Ozzah]

Could you just let the water evaporate to leave the cinnamaldehyde behind? or would that evaporate too?

[@maay434]

Hi, what lab materials and equipment did you use from start to finish?I need to do this experiment at home. My collage will send me what I need. Thanks

[@tubesurfer23]

Wow that was a lot of work and glass to have to clean up later. Is that the same way people make hot pepper essences and create ever more dangerous "new worlds hottest hot sauce's"? And thanks for the vid, I still need to decide between physics or chemistry and I'm thinking more about chemistry lately since watching your videos :)

[@NileRed]

I actually made a video about extracting the essence of hot peppers. The distillation doesn't work for that because the major spiciness component (capsaicin at least) is a crystal and not an oil.

[@centrifugedestroyer2579]

tubesurfer23 "A lot of glass to clean up" I really like that you're interested in chemistry but its pretty obvious that you havent been in a lab already. I'm only a student (at university) but I had to clean five or six times as much glassware as you saw in the video on a day most of the times I've been in a (chemistry) lab. But dont let that discourage you, most of the time during extractions, destillations etc. you will have enough time to kill to clean everything.

[@no.one.two.]

Jutta Beckmann I'm a chemistry student as well and in my lab we did this exact experiment and it was a real PAIN to get all of the cinnamon leftovers out of the 3-necked-flask, the only thing worse was cleaning this after a (failed) destillation of PET :/

[@RandomExperiments]

I have done this experiment at the university. It was quite fun, even though grinding it took a lot of time... And my yield was about the same.

[@gmc9753]

+Random Experiments Use a small coffee/spice grinder.

[@oceanjunkie5968]

When are you planning on posting your next video? I check every day and find nothing :(

[@NileRed]

I am going to try to get something out in the next week. I am pretty busy with school at the moment.

[@durgathirdeye2929]

hello namaste dear NileRed...can i applied this method to all rosemary , lemon grass ginger and lemon using sodium chloride ,calcium chloride and dcm ether...please guide me posting in youtube if possible...

[@scottmichaelharris]

That’s cassia not cinnamon, however cassia is higher in cinemaldehyde than real cinnamon. Related tree bark.

[@TheRussianCow]

Is it possible to use acetone (or another organic solvent) instead of DCM?

[@espresso3242]

Could we extract Cinnamaldehyde by dissolving crushed cinnamon sticks in Isoproyl alcohol?

[@beccasneyd1251]

Hi just wondering how long the heating process took?

[@durgathirdeye2929]

hello namaste when i used 1 kg cinnamon how much water need to add and how much oil i yield approximately please suggest me...

[@elephystry]

The ingredient list suggests to me that you need 12 mL of dichloromethane and 8 mL of water for each gram of cinnamon. I do not know the yield.

[@durgathirdeye2929]

thank you very much grateful to you

[@achalawickramasurendra7850]

What is the temperature inside the vessel while boiling

[@Nexstra]

Would this work with ethyl acetate in place of the DCM?

[@predjee]

Hi Nile! Thanks! Do you know any good lecture on short path distillation for a n00b?

[@sagarkumbhar6348]

What is iodine value of cinnamon oil.

[@ericb6028]

hi. where did you obtain you distillation apparatus from? thanks in advanced

[@straightleft2225]

I know this was 9 years ago, but does anyone know if washing with brine instead of DCM would work too? I mean in principle it should work, right?

[@3er24t4g1]

For heating a sand bath works well!

[@Kloashut]

Takes a while to heat up and there is a huge temp gradient from top to bottom