How to make Banana, Mushroom, Orange, and Pear Flavoring (Acetate Esters)
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- Опубликовано: 4 июн 2014
- Organic esters tend to be smelly molecules. Some of them are pleasant smelling, while others are quite pungent and unpleasant.
In this video, we will be using acetic anhydride to acetylate 1-pentanol to make banana flavoring.
The same reaction can be carried out on several other alcohols, however, to make other scents, such as mushroom, orange, or pear.
8 years ago: remember, this was made in a lab, so you should not eat it, or even try it.
Couple years ago: I'm making grape flavor from vinyl gloves. It tastes ok, but if I have enough, it will keep all birds away and possiblykill them. Next week I'm going to make water out of diamonds and drink the most expensive water ever
Today: I am renting an island to make the smelliest chemical known, notorious for making an entire town vomit and getting even more noxious as the chemical is diluted and dispersed. Good thing the nearest houses are 200 yards away, down wind. Tune In next week when I drink paint thinner I have converted into cherry soda
That's an evolution
😅😅
Mushroom flavored candy
gafeht lmao Mario and Luigi would love them. xD
EWW!
_mMmMmMmMmMmMmM_ !
Thanks I hate it
Imagine if it were a naturally sweet-tasting mushroom.
Something about watching these reactions is very relaxing.
what a lad, keeping it simple and explaining the chemistry behind it mah boi
Congrats Nigel, this video is being used by my Ochem 3 professor as a demo video!
When you said you would keep it basic, you lied
its acidic.
Lol
He used a _round_ bottom flask so why being so _flat_?
Austin _game You're sense of humor is vitriolic.
I remember doing this in chemistry, thank you so much for your video man!
All it really did demonstrate to me though, is how much I've seem to have forgotten of my chemistry knowlege...
Love your content! Finally taking organic chemistry and we're using this for a lab!
I performed this exact experiment in my lab. When adding water to the solution to neutralize acetic anhydride, the solution in my round bottom flask boiled out (pretty much exploded out). I was able to save some of it to get the final product. Furthermore, maybe warn the students to use a dropwise neutralization of the acetic anhydride. Really pungent banana though! That was fun.
Thank you sir. This was very helpful!
From a chemistry teacher in training
Nice!
Just what I needed for my 3,6-dibenzoylmorphine reaction...
It do really reminds me of my time in the Lab.
I liked the colors, helped me understand what is going on
my name is ester
Waiting for a video of you in a round flask with sulfuric acid and stir bar.
Mrs. Fischer gets esterified....
Schulhof in german means School ground
what do you smell like?
Ester bond
I tried my hand at home distilling ages ago; often there would be a strong banana smell to the distillate, but only a few milliliters came over before it cleared up.
All manner of stuff before and after the ethanol and even some furans for afters. Mmmm, wet cardboard smell!
Keep yer cuts clean, boys!
I want some question
in the video if use 2-penthanol is banana flavor, benzyl alcohol is peach flavor and etc.
But in the video, using 1-penthanol then final product is banana flavor.
Can I use either 2-penthanol or 1-penthanol for make banana flavor?
Did this for octyl acetate. Doing this with longer alcohols will mean you will lose less of your product in the washing steps but will require a higher temperature to distill at the end. For my reaction, I used 30mL of 1-octanol. After the reaction and washing steps, I dried the crude organic layer over MgSO4 for 15 minutes and filtered, then used an impromptu short path air condenser (made using the 75 degree and 105 degree joints with a short glass tube connecting them), then distilled the mixture under vacuum to yield 25.18g of crystal clear octyl acetate, 77.0% yield.
But what does it smell like?
There is an orangey-citrus smell, but it is very synthetic in character, like many of the esters mentioned in this video
Can you write the protocole below because I don't find it anywhere on the web. It's for a homework
Nononanol -- doo dooooo dadoodoo
Great vid! Is there an easy way of getting some of the alcohols?
You made me crave flavored mentos...
So you made mentos. :)
Is there a specific name for the thermometer adapter your using? I have been trying to find it forever, hate those cheap screw on ones.
Cool
@nilered Hi Nile, your videos really revigorished my passion for chemistry, after forgetting about it years ago. I'd like to know, where did you buy the heating mantle used in the video at 6:00 ? I'd greatly appreciate~ Thanks
Sofiane
Would glacial acetic acid work instead of acetic anhydride here? The anhydride should be made in situ no? Or another mechanism should intervene but in the same way as ethyl acetate can be made from ethanol, glacial acetic and H2SO4. Just my guess.
I don't need any more banana flavoring. Trust me.
Lmao
Wtf man lol
I don't trust you
Nice
Maybe a Fischer reaction between BnOH & GAA could suffice? I made EtOAc once.
could you make a video of dioctyl maleate synthesis
Yeah, let me just go grab the acetic anhydride that I got from the walmart.
:/
I made isoamyl acetate today, smells like candy banana :)
do any changing the brach of the pentanol in this reaction replayme brother
I did a similar, much simpler experiment today in class. I added the Sodium Carbonate to my mixture too early! Literally, all the liquid just spilled out of the test tube :( Lol
I'm re watching this video and I was thinking won't there be water in the end because the acetic acid can make more ester with the alcohol
So... How do you go about making this edible?
Benzyl acetate is a major component of jasmine. Some say it has a floral odour.
could you use methanol for this reaction or larger alcohols or mabe even phenol? i am just wondering.
Yes absolutely. In fact, you can use cooking oil and methanol as the reactants to make biodiesel.
any idea what the fake rootbeer compound in 'rootbeer barrel' type candies might be?
It's actually a mixture of flavors. Get a swig of rootbeer and breathe out through your nose, you'll smell wintergreen. Shake the bottle and pour it into a glass, let it sit overnight and it'll have a weak, flat, very sweet slight cherry flavor. The original flavoring was from sassafras tree roots. It was banned after a cancer causing chemical was found in the root extract, only after they injected a rat with the certain chemical in high does a bunch of times. I still drink tea made from the roots, our property has alot of sassafras saplings.
Thank you for the video. I have no experience in Chemistry but i'm interested to make flavor for beverages. Is this process same goes as to make them? And also, is there a book which you can recommend me on how to make flavor to use for food and beverages?
I don't recommend you drink/eat anything you make
Why did you list 2-pentanol as giving a banana smelling product in the table at 1:00 but said you were using 1-pentanol? Was that a typo? Or was there a specific reason you went with 1-pentanol instead of 2-pentanol?
I believe both isomers will give banana-smelling esters, he just used the 1-isomer in this prep.
i did this at school but with ethanol and butanoic acid to make pineapple
Edible chem? Or smellable chem?
cant i use acetic acid insted of acetic anidryde?
Can ANY smell/taste be replicated artificially through the science of chemistry??
yes probably
Will it work with dil. H2SO4 as well?
TL:DR video shown makes the scent of apples, not bananas. Neither 1 or 2 pentanol would yield the isoamyl acetate for bananas.
Probably been covered but I can't see any mention of it in any of the recent comments so here it is. What is made here is known as amyl acetate which has a scent of more like apples. In order to make the true scent of bananas what you need is isoamyl acetate made from isoamyl alcohol which is a completely different substance. Then I have no clue as to where he got the 2-pentanol from because that would make sec-amyl acetate which I couldn't find any literature on its odor but that could be an interesting experiment. Though from what I can tell the other alcohol to acetate scents are accurate.
@NileRed
"Certain species of honeybee release a pheromone, isoamyl acetate, when the ovipositor is pulled from the abdomen after stinging a victim. This pheromone attracts other bees to the victim and thus incites multiple stings."
Would you be willing to test the effectiveness of laboratory-created isoamyl acetate and whether or not it agitates bees in some way?
I am wondering if a time I got randomly stung by bees had to do with banana flavored candy that contained isoamyl acetate falsely triggering this sting response.
The carbonyl gets the H+ from h2so4 then the -OH from the pentanol attacks the -OH cation formed to stabilize it, and so o
n..
We just made banana oil in organic chem lab in uni...
what is a good source of benzyl alcohol? i really would like to know.
i also want to know the best source of acetic anhydride is
Where do you get all these chemicals? Acedic anhydride is hard to get cause it's used to make heroin from morphine.
Can you do all these esterifications with glacial acetic acid and the alcohol, and then just distill off the ester?
The issue is that acetic acid is bit a very good acetylating agent. You might be able to do that, but I imagine the yield would be extremely low
Nile Red Is it just that the equilibrium with acetic anhydride is further shifted towards the products?
Yes because acetic anhydride is destroyed when it acetylates and there isn't really a reverse reaction to go back.
Upon further reading, you might be able to get yields of a typical Fischer esterification (50-70% all depending on the equilibirum). If you do it with molecular sieves present, you can pull the water and maybe get even higher.
Nile Red And I could also probably increase yields if I distilled off the ester product.
Nile Red Actually that probably won't work--aren't the boiling points of esters and their corresponding alcohols usually very similar?
So then, how do they make it if not in the lab?
What smells does it give if you use ethanol or methanol ?
Christopher Mag Something like the vaporub ointment, I did it once using ethanol
Menthyl acetate? I thought isopropyl alcohol was used for that.
Ethyl acetate smells like (and in fact is) plastic model cement.
Who was talking about Ethyl acetate?
Ethyl acetate is the acetate ester of ethanol.
I was thinking he made a mushroom lol
Why use H2SO4 as the catalyst? Why not Carbonic Acid? or any other acidic catalyst? I'm an IB student and was thinking of comparing the % yeild, the rate of reaction or any other quantitative independent variable based on different catalysts for my HL Chemisty IA. Esterification reactions just happen to be one of the coolest potential reactions for me to compare with a catalyst.
Rose-Colored Glasses Sulfuric acid was easier to get than carbonic acid
H2SO4 is an extremely strong acid,It'll give the H+ needed for the reaction to proceed.,Carbonic acid (barely any is formed when dissolving CO2 in water,lots of CO2 remains as is,plus Carbonic acid is such a weak acid) or other weak acids barely ionise in solution,while H2SO4 fully ionises into H+ and SO4-,(Also,in regular esterifications where an carboxylic acid and alcohol are refluxed with a small amount of H2SO4,The Dehydrating properties of Sulfuric acid are used to remove the water and prevent the formed ester from reacting with the water and forming the starting products)
Are you making mezcal?
You should consider redoing this video, but with all the listed precursors. :3
How do you make acetic anhydride from glacial acetic acid? Can you just dehydrate it with sulfuric acid?
You can't make it that way. You need to make ketene from acetic acid first, which is can't really do yourself. You will need to go via a different method. If you do some research you can find a viable one, but it is a little roundabout and uses chemicals that aren't too easily obtainable. I don't remember the synthesis off the top of my head though.
Ok thx, I might just try to buy a small quantity.
It is hard because it is a controlled substance due to it's use in drug synthesis. However, you can probably order some!
Here is a synthesis: www.erowid.org/archive/rhodium/chemistry/anhydrides.html
It requires PCl3 though, which can also he hard to get.
TheChemistryShack What about using P2O5?
Nile Red Wouldn't such method produce Acetyl Chloride?
Can you use glacial acetic acid instead of acetic anhydride.
skagsux Yes
Are parts of that video sped up or is the experimenter just manic? ;-)
the video is very much sped up. I don't think anybody can work that quickly, much less can layers in a separatory funnel separate that fast.
he's a magical manic chemist that speeds up his videos =D
He's just built different
I recently acquired some n-hexanol, and I must say that in very small concentrations it has a very "mushroom-ish" smell to my nose (not in a good way).
It should smell similar to freshly cut grass. It is very interesting how the smell can change so much by a simple esterification.
Well, it sort of has that "grass"-smell in heavier concentrations, but when the smell is barely noticeable, to me it`s a bad smell.
Yeah, most of those chemicals smell quite unpleasant in general.
i wan to make butanone form n-butanal can you tell me how to do it?
I am not sure if you can. If you could, it would definitely be a difficult process
Just mix ethanoic acid with ethanol in the presence of conc. Surfuric acid and you have your ester
ah sure, let me just FUCKING BOOT UP MY TRUSTY NMR MACHINE THAT I HAVE LYING AROUND AT HOME
*Instrument
you shake a separatory funnel like my grandma
"You should not eat it" bro what happened.
Use a NMR for that compound is really excessive and expensive. An IR for functional group is more than enough
+benzedrex it costs like 2 dollars for an NMR
+Nile Red If you have a lab with a NMR you will pay just for deuterate solvent and a little bit of electricity otherwise the cost is about hundreds dollars.
Anyway buddy I love your videos
benzedrex oh yeah, it was when I was a lab tech. I would run a lot of samples and just throw and extra one in here and there.
+Nile Red NMR is a very good specialization for a lab tech. Actually I am improving my experience on ICP-MS. Buddy trouble shooting is so painful!!!
I am a little bit tired to work with instruments.
+Nile Red heh, very sneaky.
I know as benzyl acetate smells jasmine
Can I use separatory funnel instead of dropping funnel?
***** yeah but remember that it has no pressure compensation!
Chem1456 Thanks:)
*****
you're welcome
If you used acetic acid instead of acetic anhydride, wouldn't you create the pentyl acetate and water instead of acetic acid?
yea,i believe it has to be refluxed for the esterification to occur
Hello¡ amazing video. I am required to do a scientific report on this video and required some additional information to completed. Is there a way one can contact the video creator?
can u made it risinine from castor beans?
Ricin? That's illegal.
please consider doing an experiment synthesizing methyl salycilate from pepto bismol with minimum waste.
+Edward Vassell I could, it's jsut that getting it from aspirin is so much more cost effective
i thought you would multi task and make something out of the bismuth by product, by the way, didya ever try making calcium dichromate or calcium permanganate?
Edward Vassell I have actually never tried to make either of those. I do want to make ammonium/potassium dichromate at some point though
that sounds cool. i heard that the calcium and strontium salts of permanganic acid are very elegant. cant wait to see the double dichromate video.
Juicy Fruit gum?
What would isopropanol, methanol and ethanol create?
+TheTechnic Lord Off the top of my head I don't know, but you can look them up and see.
i think they produce isopropyl acetate, which has a fuity smell, but i don't know what fruit it is, methyl acetate, which smells like certain glues and nail polish removers, and ethyl acetate, which smells like pear drops
Syrian rue extract crystal how to make recipe video?
Mushroom smell?
wait did you use 1-pentanol or 2-pentanol because it says 2-pentanolt 0:48
Why isn’t this in edible chem?
Gotta activate the electrophile in that mechanism discussion, brah
Mushrooms smell?
They do, but it doesnt smell too good. It smells like an internet furry covered in cheeto dust and who hasn't showered in a month. Basically like every furry out there.
Austin _game ???
Kolynk Idk. Im retarded.
Austin _game k lol
Krisztián Szirtes u wot m8? fite me 1v1 dust on csgo m8 autosnipers only
Why not just take acetic acid and alcohol?
Reading a RedBull can got me here.
Or better known as ethanoate esters.
are all artificial flavourings as safe as natural flavourings for human consumption?
Since artificial flavourings are made chemically,It's a bit more dangerous if they are not pure,Remaining start products or catalyst can be dangerous.
WHY didn`t you just use glacial acetic acid instead of that precious acetic anhydride ?
I wanted to use a different method than a basic fischer esterification, which is an equilibrium reaction. Also, I already made Wintergreen using Fischer Esterification.
for the distillation at 6:00 you're using a special teflon Quickfit for the thermometer, can you tell me where i can buy it?
I think you used the outdated naming system
Everything would be fine, but acetic acid anhydride is a substance that is almost impossible to find. Such reactions should be preceded by a video about how to find or make acetic acid anhydride.
Why not just make it from salicylic acid? It's much eaiser and there's a salicylate ester for every scent or flavor. Natural scents and flavors are litterally due to salicylates present in fruits and herbs.
Can i use this for vaping?
Man my friend got lung cancer after only 1 month of vaping quit before it's too late
You can do anything....once
"this was made in a lab so you definitely shouldn't try it"...... I mean..... I bet it's safe.
It belongs in a museum!
Is it actually with those flavours, or is it only with those aromas, and it actually tastes horrible?
its both but is so concentrated it would probably destroy your taste buds temporarily (they grow back)
this is what they put in candy
NEVER EAT ANYTHING MADE IN A LAB. No.1 rule of chemistry.
Mmmm, mushroom candy. My favorite.
+Austin _game is it not ok to eat it if you made it in brand new equipment
I'm assuming these are not food safe, either.
If you can find a source of food grade materials, then they would be. But with lab grade, no.
Thank you!
By the way, do you know where, if anywhere, I could purchase food-grade acetic anhydride? I've looked around, but I was wondering if you had any special sites?
I am unable to help you, sorry! I don't even know where I could get any grade of acetic anhydride. It is pretty controlled as far as I know due to its use in drug synthesis.
OH! Did not know THAT! Never mind then!
It sounds like fun at first but you can open up all the windows in your house and that shit will linger for days
What’s the point of making it if you can’t even try it :(
Acetic acid sounds like acidic acid.
Shaken not stirred
One can work at a school lab, or one can live in Canada...
Or in finland like me.
robinhooodvsyou Or in China like me.
Davy Zeng Or America like me.
HClO3 Chem Every kitchen is a laboratory. You have hot plates, glassware, measuring devices as scales and scoops, Acquiring more specific or enclosed systems have been made and modified by bootleggers the world over. Don't be your own enemy here, use your head. What can be envisioned can be created.
+James Jefferson I totally agree. When I was in college the last semester, I tried to make calcium citrate from an antacid tablet and lime juice. It works surprisingly well.
I’ve done worse (thousands of times worse) than eating the stuff made in the lab.
Alexis Harper lab-made lube?
Such as?
@@caseyschannel He died from eating his lab-made stuff