> chemistry > esters > how-to-make-acetate-esters-with-acetylation-acetic-anydride-nilered

How to make Banana, Mushroom, Orange, and Pear Flavoring (Acetate Esters)

NileRed - 2014-06-05

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.

Austin _game - 2016-07-23

When you said you would keep it basic, you lied

its acidic.

Infinitesimal Philip - 2017-09-02


Mexi Chemia - 2018-02-14

Austin _game now that’s a pun

Werner Hiemer - 2018-08-11

He used a round bottom flask so why being so _flat_?

warefairsoda - 2018-08-20

Austin _game You're sense of humor is vitriolic.

gafeht - 2017-02-16

Mushroom flavored candy

AngryPasta - 2019-04-23

gafeht lmao Mario and Luigi would love them. xD

DoctorWhoRoblox1935 - 2019-10-21


Aiex 314 - 2021-01-05

mMmMmMmMmMmMmM !

coolweirdgreat - 2014-06-07

How does one acquire acetic anhydride without the feds bursting through the front door?

Sofiane B - 2017-03-10

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

kader gumus - 2019-07-15

Get acetic acid and sulfuric acid.
It makes pentyl acetate as well!

Colton Spare - 2020-03-22

coolweirdgreat 😂😂 you could figure out how to get a reaction vessel to 700 degrees celsius with dry acetic acid and pull a vacuum.

Probably be easier to react acetaldehyde with cobalt(ii) acetate at moderate temper (55 °C) with pressure in reaction vessel around 5 bar and, you would get acidic acid and acetic anhydride

Alper Bilgin - 2020-04-22

Heating dry zinc acetate under vacuum gives it.

RiseAsTheDawn - - 2020-10-10

@kader gumus yes but acetic acid is extremely weak and if your reactant concentration is not high enough, the yield wont be great

ophello - 2016-07-20

Nononanol -- doo dooooo dadoodoo

Knott Reel - 2017-06-16

Something about watching these reactions is very relaxing.

Wasp Stomper - 2020-01-22

Yeah, let me just go grab the acetic anhydride that I got from the walmart.

Bxnkroll BobbySands - 2020-06-01


aLmAnZio - 2015-05-15

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...

illya.ruslanovich Shevchenko - 2021-02-13

Aspirin instead of acetic anhydride also works as an acetylating agent. I put a tablet of it under ethanol, and ethyl acetate formed very quickly.

I then used this new reaction for the synthesis of ethyl acetate. The yield is now unknown (I will write later) but it should be high (read the explanation), the most important is that this reaction does not use Ac2O, which is dangerous and a precursor.
Explanation: when the phenoxide anion (the leaving group) is formed, it (a nucleophile) is protonated by COOH, producing stable and non-nucleophilic phenol group.

Colin Martin - 2020-04-27

Congrats Nigel, this video is being used by my Ochem 3 professor as a demo video!

liam bryce - 2017-10-11

what a lad, keeping it simple and explaining the chemistry behind it mah boi

naif chen - 2017-08-12

It do really reminds me of my time in the Lab.

Toby Hoch - 2020-11-28

Maybe a Fischer reaction between BnOH & GAA could suffice? I made EtOAc once.

Felix Pettersson - 2018-01-10

So... How do you go about making this edible?

ShadowOfChemistry - 2015-09-13

You used 1-pentanol, but at 1:10 it says in the bottom right corner that you need 2-pentanol for a banana smell?

Rawest - 2016-05-09

+LargeVirus could also use isopentanol

marialiyubman - 2020-01-08

You made me crave flavored mentos...
So you made mentos. :)

The White Lotus - 2019-12-17

Thank you sir. This was very helpful!
From a chemistry teacher in training <3

Florent Venhari - 2016-07-06

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

A Broquet - 2018-04-28

Benzyl acetate is a major component of jasmine. Some say it has a floral odour.

Jan-Willem Langenbach - 2014-06-05

Great vid! Is there an easy way of getting some of the alcohols?

Franz Goerlich - 2018-06-01

I made isoamyl acetate today, smells like candy banana :)

NecroBanana - 2016-04-19

I don't need any more banana flavoring. Trust me.

Rawest - 2016-05-09


Sofiane B - 2017-03-10

@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

Gabriel K - 2017-06-17

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.

Ali Majid - 2018-04-06

could you make a video of dioctyl maleate synthesis

Apple Dream - 2017-09-30

do any changing the brach of the pentanol in this reaction replayme brother

Greg Gallacci - 2018-10-22

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!

BioDOC - 2020-06-05

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?

steubens7 - 2015-12-21

any idea what the fake rootbeer compound in 'rootbeer barrel' type candies might be?

kd9bwi - 2018-11-29

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.

Nathaniel Sellis - 2017-09-29

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.

Wonderland - 2015-03-31

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?

Keith - 2016-05-26

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?

mpk 666 - 2016-07-01

I don't recommend you drink/eat anything you make

Jarom Schafer - 2016-10-18

could you use methanol for this reaction or larger alcohols or mabe even phenol? i am just wondering.

Alexis Harper - 2018-02-10

I’ve done worse (thousands of times worse) than eating the stuff made in the lab.

Zach Brown - 2018-11-18

Alexis Harper lab-made lube?

casey - 2019-11-03

I know this is an old comment, but I am endlessly curious - please tell us

Awab Qureshi - 2020-02-19

Such as?

Niklas - 2020-09-08

@casey He died from eating his lab-made stuff

Nothing\ - 2017-01-31

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?

christianvn1 - 2017-02-05

I believe both isomers will give banana-smelling esters, he just used the 1-isomer in this prep.

이성현 - 2018-09-30

I know as benzyl acetate smells jasmine

Bruce Mardle - 2015-09-05

Are parts of that video sped up or is the experimenter just manic? ;-)

Matthew Ferrie - 2015-11-24

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.

c3h8O - 2016-09-15

He's magic

EvilPlagueDoctor - 2017-03-12

he's a magical manic chemist that speeds up his videos =D

Vaprin - 2020-09-10

He's just built different

ShadowOfChemistry - 2016-05-09

so where do I get Ac2O now? sees to be nearly imossible in europe because it's used for heroine.

Toxiq1337 - 2016-07-19

Ac2O is not the only option to do this reaction! since you basicly produce the ester of acetic acid you have several ways of getting to the product. for example using just acetic acid and a catch for the produced water is possible. another way would be to use the bromoalcane to get rid of the water as a factor

ozan kızıl - 2020-02-20

can u made it risinine from castor beans?

พงศธร มนุโศภิษฐ์ - 2014-06-15

i wan to make butanone form n-butanal can you tell me how to do it?

NileRed - 2014-06-15

I am not sure if you can. If you could, it would definitely be a difficult process

Aleksander Sobolewski - 2015-04-23

Can I use separatory funnel instead of dropping funnel?

Chem1456 - 2015-04-29

@Aleksander Sobolewski yeah but remember that it has no pressure compensation!

Aleksander Sobolewski - 2015-04-29

@Chem1456​ Thanks:)

Chem1456 - 2015-04-29

@Aleksander Sobolewski
you're welcome

Edward Vassell - 2015-12-14

please consider doing an experiment synthesizing methyl salycilate from pepto bismol with minimum waste.

NileRed - 2015-12-16

+Edward Vassell I could, it's jsut that getting it from aspirin is so much more cost effective

Edward Vassell - 2015-12-18

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?

NileRed - 2015-12-18

@Edward Vassell I have actually never tried to make either of those. I do want to make ammonium/potassium dichromate at some point though

Edward Vassell - 2015-12-19

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.

Ryan Napier - 2018-04-13

Edible chem? Or smellable chem?

Christopher Mag - 2015-04-11

What smells does it give if you use ethanol or methanol ?

Rafael David Castro Luna - 2015-06-16

@Christopher Mag Something like the vaporub ointment, I did it once using ethanol

Richard Smith - 2017-05-04

Menthyl acetate? I thought isopropyl alcohol was used for that.

Karri Koivusalo - 2017-05-15

Ethyl acetate smells like (and in fact is) plastic model cement.

Richard Smith - 2017-05-16

Who was talking about Ethyl acetate?

Karri Koivusalo - 2017-05-16

Ethyl acetate is the acetate ester of ethanol.

Rose-Colored Glasses - 2017-11-27

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.

Quark Samurai - 2018-06-17

Rose-Colored Glasses Sulfuric acid was easier to get than carbonic acid

robinhooodvsyou - 2014-06-11

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).

NileRed - 2014-06-12

It should smell similar to freshly cut grass. It is very interesting how the smell can change so much by a simple esterification.

robinhooodvsyou - 2014-06-12

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.

NileRed - 2014-06-12

Yeah, most of those chemicals smell quite unpleasant in general.

c3h8O - 2016-09-15

+NileRed what might generate a fresh dill smell?

Andrew Villalobos - 2020-08-01

Damn it! I was excited seeing benzyl alcohol as a working alcohol. Then I saw the acetic anhydride. There goes that lol. Maybe glacial acetic acid works too? I know that many reactions won't work with acetic acid instead of acetic anhydride but some can work with an excess of acetic acid.

MR Poopo - 2020-09-11

You read the comments above

Andrew Villalobos - 2020-09-11

@MR Poopo
Fuck off you twat!
Also I didn't see anyone mention that acetic acid works so lick this lmao

MR Poopo - 2020-09-11

Im sorry, does your butt hurt? There is a great video about extracting benzocaine from anal lube on this channel. Go check it out

Andrew Villalobos - 2020-09-11

@MR Poopo I'm sorry was your ego hurt? You made a stupid comment so I did so too. Looks like you don't like the taste of your own medicine. Don't worry there are others out there like you! 😋

MR Poopo - 2020-09-11

@Andrew Villalobos yeah? how did you get there from me burning you twice? Its pretty plain to see you are projecting.

TheChemistryShack - 2015-07-06

Can you do all these esterifications with glacial acetic acid and the alcohol, and then just distill off the ester?

TheChemistryShack - 2015-07-08

@Nile Red Is it just that the equilibrium with acetic anhydride is further shifted towards the products?

NileRed - 2015-07-08

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.

TheChemistryShack - 2015-07-08

@Nile Red And I could also probably increase yields if I distilled off the ester product.

TheChemistryShack - 2015-07-08

@Nile Red Actually that probably won't work--aren't the boiling points of esters and their corresponding alcohols usually very similar?

NileRed - 2015-07-08

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.

Oscar Poll - 2016-09-13

wait did you use 1-pentanol or 2-pentanol because it says 2-pentanolt 0:48

Sikhumbuzo Arthur - 2017-08-21

thank you so much

Ester Schulhof - 2016-12-21

my name is ester

Rob Sep - 2017-10-22

Mrs. Fischer gets esterified....

Pik Ass - 2019-01-10

Schulhof in german means School ground

kader gumus - 2019-07-15

@Toy-Yoda And 1-propanol and valeric acid. Makes propyl valerate.

ChannalMath - 2019-10-07

what do you smell like?

Definitely not Yuri bezmenov - 2020-10-26

Ester bond