Making acrolein

In this video, we make some acrolein by catalytically decomposing glycerol.
This video had to be made outside, so the lighting is not the greatest.
Tautomerization mechanism: images-mediawiki-sites.thefull...
Glycerol video: • How to make Glycerine ...
Anhydrous magnesium sulfate: • Preparing a Drying Age...
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Nile talks about lab safety: • Chemistry is dangerous.

[@adhillA97]

"I really don't ever want to work with it again," coming from the guy who makes Chromyl Chloride for fun, must be no joke.

[@Lieutenant_Dude]

It was a wwi chemical weapon

[@thatSkyKosmoTactical]

That says a lot

[@DarmaniLink]

And apparently people who smoke are constantly exposed to this shit and expose others to this shit

[@drasiella]

Toxic and carcinogenic is fun, but stinky isnt

[@batznocharge]

@@DarmaniLink your welcome

[@Thyagohills]

Guys, when it says: "altered gene expression" and "mutation", read: cancer and tumours, not x-men abilities, though. lol

[@greenlawnfarm5827]

You cant drink everything that looks like soda i hope you know.

[@Slowly_Going_Mad]

It taste like burning.

[@yungchill69]

Speak for yourself, I for one am expecting my wolverine claws any day now.

[@bundlesofjoe]

That still doesn't explain where my fourth testicle came from.

[@emmajaubert6249]

@@bundlesofjoe four? pleb i have 5

[@mr.niceguy8247]

So is this like cancer sauce?

[@Cajuu]

lol exactly

[@papisuckmypoosay69]

cancer sauce is benzene or chromyl chloride

[@user-io3xp7qx4p]

More like a cancer demi gloss.

[@asmolbean9300]

@@papisuckmypoosay69 to quote our lord and saviour *remember benzene it's back!* - explosions and fire

[@karlbergen6826]

Acrelien is extremely irritating! When things burn they only make traces of it.

[@hamaltheya3919]

Oh cool, a new episode of Edible Chem !

[@jowanharvey1874]

The forbidden edible chem

[@laurenceharper2037]

Yummy

[@annacochran4418]

I could go for some good ol' acrolein right about now. Maybe with a side of chromyl chloride.

[@jlewwis1995]

@@annacochran4418 mix em together and drink from some uranium glass :)

[@emmajaubert6249]

everything is edible at least once

[@albertkjolby405]

This is honestly my favourite channel on youtube, so satisfying to watch the whole process

[@NileRed]

Thanks, I appreciate the comment!

[@stans3257]

Agreed

[@paulsonaksones]

@@NileRed w

[@masterandshadow3944]

@@NileRed heyy, are you French/in France? Because 2:08 Glycérine is french I'm french

[@1brytol]

@@masterandshadow3944 He is from Quebec, Canada

[@gilbs8247]

Acroline is really nasty stuff. I used to do research on renewable diesel made from various vegetable oils. Even with a fume hood, one whiff and your head is spinning.

[@starlitstreet]

ever figure out which vegetable oil was the best for engines or was the project abandoned?

[@justinbarton9662]

Also wondering did y'all ever publish?

[@akuakkk1908]

@@starlitstreet if i remember correctly, every vegetable oil produce the same biodiesel (with different proportion) and it's more of which one is efficient conversion (biomass to biodiesel conversion rate as well as which one require less material/energy to do).

[@akuakkk1908]

@balddicknosedasscanoe i don't know, i am just a student and one of the topic i need to review just focused on conversion rate and finding parameter that matter and how it affect it. While surfing through, either i forgot that it have been mentioned or it rarely ever be mentioned is how the proportion (or rather different vegetable oil) affect the actual quality of the biodiesel when it's used on the car. (My guess is that, just like many other production. You just compensate the pure biodiesel created by mixing it up with other chemical or treated in order to reach desired value. So... No idea for the home-made one. Or it's separated topic that are scrutinized independently of each other which i highly doubt).

[@akuakkk1908]

@balddicknosedasscanoe um, just a little question just to make sure we're on the same page. When you said biodiesel, do you just mean vegetable oil or an alkyl esters which is biomass (including vegetable oil) that already went into conversion into biodiesel. I am really sorry for this as i have a feeling that we're not actually talking on the same page....

[@notgood38]

Acrolein is brutal even with a fume hood. You've got balls. I've also had polymerization destroy reagent bottles.

[@NileRed]

Yeah, it definitely was not nice. Also, polymerization is so unfortunate.

[@justinvzu01]

NileRed: It's extremely dangerous, and should be handled with care Smokers: We're all dying anyways, so let me just~

[@Ghuirm]

might as well not cook your food anymore as well

[@nebulousisgod]

The doses are what’s bad. We all know cigarettes are worse than cooking your food. Inhaling smoke is worse. There’s still only traces left behind from both reactions. You can’t judge anyone honestly whose addicted unless you’ve personally experienced it.

[@elijahaitaok8624]

@@nebulousisgod I’ve never done meth before and I can safely assume those addicted to it will be incredibly unpredictable and undesirable

[@internetbodhi1009]

@@elijahaitaok8624 uh huh. You can also just ignore the circumstances that brought them to it, but whatever.

[@sullivancurran8432]

@@elijahaitaok8624 funny enough buddy, I’ve found a lot of junkies that are better people than a lot of straight edge mfers, they would give someone the shirt off their back, don’t automatically assume they are undesirable and unpredictable, the unpredictableness comes from psychosis which is really no fun, as long as they sleep then it’s a functional substance, even with how addictive it is, you also have to think about the bioavailability of the different Routes of Administration, which offers the most intense rush, orally it’s not too far off from adderall just more potent, but iv’d, intranasal and boofing are what really fucks it up and causes the euphoria to take complete control, if you think everyone of them is so down bad and so under control that they are willing to stab you for a shard, then your wrong man

[@Kloashut]

This was my fist experiment for practical organic chemistry. Needless to say that we were very happy that we had decent fume hoods.

[@Rhodanide]

9:33 Nile, Patrick needs his lab jack back.

[@NileRed]

What if I am Patrick?? (I am not though)

[@Rhodanide]

NileRed Did you take Spongebob's lab jack, too?

[@wilbertbirdner1303]

i just figured the jack was named patrick

[@sleepful1917]

i knew i wasn't the only one who noticed that lol

[@asmolbean9300]

@@NileRed who is Patrick tho... one of life's deep questions

[@YpsilonTM]

Really nice to see this. I work at a an acrylic acid plant. And its indeed the first step of our reaction.

[@thingyjim]

Every time I’m stressed or sad I watch this video... I don’t know why, I just do! Thanks Nile!

[@hristonaydenov6130]

I understood about 5% of this video, but it's still fascinating to me how complex chemistry actually is.

[@maxdanny5111]

Hey man I just wanted to say I don't know much about chemistry but I have watched almost all of your videos and I have enjoyed all of them so keep up the good work

[@kastynm.9004]

18 seconds in & he makes me regret picking this as my cigarette break video

[@Crimson_zack01]

In my entire school life we were never taken to chemistry lab for practicals . But becz of your channel I got satisfied. So thanks alot

[@petrp9840]

I'm glad you made this video. I have done acrolein twice. In my first synthesis I used a dropping funnel just like you and I found it completly unnecessary as well. I did't use the second flask with sodium chloride and i just took the receiving flask and used a vigreux columnfor second distillation. I also used potassium bisulfate instead of magnesium sulfate. In my first time my yield was just 17%, so next time I used twice more potassium bisulfate and that incrised my yield to 31%. I stored my acrolein in freezer but a week latter I also had just polymers.

[@petrp9840]

yeah and i believe that the best way how to clean the boiling flask is just pouring solution of sodium hydroxide in it and let if react for day or two, than the flask was completly clean. :)

[@ainurmusician64]

2:12 Dang, he held back on releasing his epsom bath salt video for 5 years

[@ainurmusician64]

@@Blblblbl7312 Is joke

[@balisticren6155]

@@ainurmusician64 bullshit

[@WineScrounger]

Mmmmmm b a t h s a l t s

[@jamesweldrick9761]

Loving the upload frequency recently! Another great video :)

[@marija6113]

I think ive rewatched every one of your videos like 100 times. i dont know why, but they are so relaxing 😂 and te perfect way to procrastinate writing my thesis

[@burkhartsimon1332]

I really enjoy all of your videos, its great so see the practical side of chemistry. Have you ever considered doing videos explaining key concepts in organic chemistry? You seem to know so much about it, I think you could gain a much larger following with a video series on concepts of organic chem.

[@rossy9715]

That would be amazing!

[@laurenkirby97]

Explanations on cleaning chemistry equipment are always welcome, you should make a series on that topic.

[@ShmoozeEvolution]

Lots and lots of potassium hydroxide, water, and ethanol lol.

[@matissdrava6827]

Chemestry videos in 60fps look so amazing! Thank you nile!

[@ARSZLB]

uh...but it’s not 60fps...?

[@quintonporter270]

@@ARSZLB it is

[@zuthalsoraniz6764]

One reaction that I think you could demonstrate would be the transesterification of vegetable oil with ethanol or methanol. You could then e.g. also demonstrate the difference in viscosity between the oil and the products.

[@dogoven.]

You know this dude has to have the gnarliest bong you’ve ever seen.

[@JohnFKennedy420]

Hell yea

[@jesseleavitt2818]

Thank you for providing the mechanisms! +NileRed

[@wiretamer5710]

Thanks so much for the cleaning section... so important!

[@Keegan414]

another great video! keep up the good work mate

[@MrSmokinbuddah]

I'm super glad I watched this, at first I was like 'meh acrolein' but this actually helped me identify the terrible, terrible smelling stuff I produced when I left a flask on the heating mantle to distill and forgot until the next morning. Also, I think I'll be making up some piranha solution now, and maybe I can actually use the flask again!

[@jeremymozlin]

It makes me wonder if this is what I produced when I left caramel cooking on the stove for something like 5 minutes too long while I completely zoned out in something else. I came back into the room and it was filled with this incredible, acrid stench, while my caramel saucepan had turned into an evil-looking black boiling cauldron. I was supposed to have let it cook for perhaps 15-30 seconds, so five minutes was an eternity.

[@livingtorment7638]

@@jeremymozlin just burnt caramel lol but idk if it could be acrolein

[@monarchatto6095]

@@jeremymozlin if you’re caramel was glycerol then maybe?

[@sleepingtiger44]

Who else watches because it's interesting and not because they are doing it themselves?

[@mudkip9531]

we all do

[@OmegaMegalodon]

yea, we are all smart. lol

[@elderzeroremorse8582]

Bakedpotato2468 I today just watch for fun.he has some super funny moments

[@kingsalomo5638]

not me XD

[@darrenburns123]

Yup.... I've no fucking idea what any of it means 🤣🤣🤣

[@JackSilver1410]

This reminds me of doing inventory for a small pharmacy office. I got pulled to count the chemotherapy medication in its own separate area. I read one label, saw "cytotoxic material. Handle with care," paused what I was doing, and proceeded to go and triple glove.

[@sammathis]

I don't know jack about chemistry or science in general, but man your videos are awesome. They really hold my attention.

[@nolansykinsley3734]

Who is Patrick? I saw the name on the lab jack.

[@sushmaverma3562]

The jack's name is Patrick

[@mrjaz666]

Yes, this is Patrick?

[@cortlanwallingford8385]

Look at that perfect 60k, congrats, great work

[@NileRed]

Thanks!

[@theonlybuzz1969]

I wish that chemistry was this interesting at school, I might have even learned from it. Gratz for showing us something interesting, even though I have no clue what to do with the end result.

[@thunderhead6133]

congrats on 60k subs!

[@MichaelFJ1969]

Thank you for making these videos, so I don't have to try this myself !

[@SuperAngelofglory]

Some old literature sources claim that if you use KHSO4 instead of MgSO4, the reaction takes place at room temperature

[@florianbeck4283]

From my lab experience, a mixture of crushed ice and scouring powder is a very good and completely safe way to get rid of all sorts of solid remains in reaction flasks. Just put both of them in there, close up the holes and give it a good shake.

[@kermichemgp]

you are brillant, i like all your amazing videos , keep adding new experimentations

[@ahuizinga1999]

Great video! shame you lost your product :/ could that have been avoided by adding more hydroquinone? also, looking forward to your bug attractant video, I'm sure you'll do a great job with that :)

[@jacobamati6406]

Hey! You forgot the links in the description at 2:15. Your videos are awesome by the way. I'm going to be starting my senior year as a chemistry major and it's always exciting to see you come out with a new video! If you don't mind me asking, are you a graduate student or do you just enjoy chemistry as a hobby?

[@NileRed]

I did 6 months are a grad student but left for some personal reasons. Right now I guess it is technically just a hobby. Good call on the links

[@yalldone4]

Its 5:30 in the morning, i havent slept yet. I dont know what any of this is, but its awesome.

[@zodd0001]

Great video ! Do you think cement or anhydrous plaster will catalyzed this reaction too ? I suggest make cyclohexylamine from cyclohexanone, ammonium formate via Leuckart - Wallach reductive amination.

[@karlbergen6826]

I'm surprised you made something as potent as acrolien. That's wicked stiff. I wonder though if it would keep as a bisulfite complex.

[@Jacksonmason112.-_]

This guy defo got a A+++ in highschool for chemistry and a pH.d in it in college or uni

[@someonesomewhere3254]

Chemistry is crazy interesting but at the same time very scary. I learn about this stuff theoretically but seeing it actually take place is surreal

[@robsonhahn]

Really interesting reaction. just a suggestion. All time we work with HNO3 and produce NO2/N2O4, is a waste of Nitric Acid, since is possible to condensate and mix nitrogen oxide with water and make more Nitric Acid, reducing losses. Would be interesting a video showing NO2/N2O4 recovery and liquefying it, like you did with NH3. Also, you can explore and show the hypergolic reaction with Aniline or furfuryl alcohol. :)

[@nephdrummond3168]

Seems like I've learned my lesson. Cover opponents monsters in aluminum foil to break fusion decks.

[@mickles1975]

You didn't provide links in the description :(

[@fwaelik]

I love watching these because it gives me the satisfaction of knowing that this is really cool, but I will never know what any of this actually means

[@JustAPersonWhoComments]

Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propylene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine.

[@enesilvian4640]

Make a video about synthesizing thioacetone :)

[@mickstephenson]

Next make Sarin.

[@ShroomLab]

I did this in a different context and used a lot of naoh drain cleaner and boiling to get the coaled residue out of the flask

[@BewareOfNerd]

No idea how this wound up in my recommended videos, but this is pretty neat!

[@JuLian-cq2qv]

Do some beautiful Diazonium chemistry. Maybe a fluorescent dye. BTW, hydroquinone might not be the best choice to stabilise acrolein as it is a quite a bit nucleophilic. I think you might have gotten an anionic polymerisation.

[@ThePaintballgun]

Look at the lab jack on the second distillation (9:36), it has the name "Patrick" written on it. Nile Red = Patrick??????

[@CC-bp2hn]

No, he mentioned before that the name NileRed comes from the first letter of his name, "N"

[@sofieknive7382]

Npatrick???

[@atlas8827]

Hm....HMMMMMM HMMMMMMMMMMMM

[@royalcommoner3873]

He looks like a Nathan to me honestly

[@Flapjackbatter]

No, no. Looks like Niels.

[@Ghostanon404]

Your style has developed a ton!! Caught this one after already watching all current things. Keep it up!

[@MrMcsec59]

hey nile red I was wondering can you synthesis pyruvic acid and acetol using peroxyacetone as the oxidant

[@ontariolacus]

Are you sure that protons are involved, not magnesium cation acting as a Lewis acid and creating some funky chelate as an intermediate?

[@killbillgoodfellas]

Bisulfate is an alternative so, it's the proton.

[@EvelcyclopS]

Would be amazing if you could synthesise some pigments like pthalocyanine blue, quinacridone magenta or some of the cadmium colours

[@ventus0517]

Ha, I just had a project in process simulations to make an aspen model to turn polypropylene into acrylic acid with acrolein as an intermediate and got recommended this video

[@Bubu567]

In fast food restaurants, sometimes oil gets around the fryer vat and gets overheated by the elements. It turns to rubber, smells acrid, and burns the eyes.

[@youngeshmoney]

No one: Nile Red: yeah imma make a carcinogen today

[@goldencharm8882]

Years old video, but figured it would be worth a shot. Would it be possible to react acrolein with DNA from something like strawberries?

[@yeet-dg7cg]

yes, why wouldnt it be? DNA is DNA

[@Turk3YbAstEr]

I remember one time thinking about switching up a synthetic route to avoid doing a huge scale iodolactonization to one that involved acrolein instead, then I saw the LD50 of this stuff. We stuck with the annoying iodolactonization.

[@therookie123able]

Can anyone explain what the dark brown blobs are at the bottom of the flask at 7:14? I came across a similar side-product when making trans-cinnamic acid from benzaldehyde and acetic anhydride using the Fisher-esterification reaction.

[@Mazaroth]

"It's just a horrible thing to work with" Just like my ex wife, burns my eyes and smells like tobacco, irritates my nasal and respiratory tract.

[@rafael53461]

HAHAHAHAHAH

[@ahuizinga1999]

funniest thing I've seen all day 😂😂

[@SixTough]

haha

[@sandokannoname5738]

She still smokes?

[@fyka2902]

All too true, but you really should have reconsidered writing your own vows.

[@CookingWithCows]

Does this get created when you vape? They use a mix of propylene glycol and glycerol to create the vapor, but when the coil in the vape pen for example gets too hot, it can burn the fluid. Does the creation of acrolein happen without the catalyst?

[@jakeevans7075]

Yeah it can happened but you wouldn't vape at those temperatures as it would be horrible.

[@elnombre91]

It definitely doesn't get formed unless you are constantly taking dry hits at high wattage. Newer vapes are much safer than the original tech that came out years ago.

[@mintleafidk477]

According to studies now, there is?

[@ECM398]

im really exited for the caffeine synthesis video, any date for release planned or anything youre willing to say?

[@stephanieparker1250]

I love the explanations of how the molecules are changing. The hydrogen is kicked off, swings back around, grabs an Uber, drops off his dry cleaning and joins up with the hydroxide for an after-party.

[@AwesomePower1234]

Could you do a video where you separate aspartame into phenylalanine and methanol?

[@NileRed]

I think i looked into it and it wasnt super easy to do. Maybe I could make aspartame though.

[@AwesomePower1234]

Aspartame is pretty hard to make from the research i have done. It involves culturing these 2 bacteria species, collecting their waste, and then fermenting them together. Nasty stuff.

[@chemicalmaster3267]

+NileRed By the way, how would you describe the smell of acrolein?

[@larrytischler8769]

Acrid, and very sharp and terribly irritating to the eyes and mucous membranes.

[@edwinsantos3615]

Use some bear spray as deodorant with a sprinkle of rotten eggs

[@Brandon78B]

Nile, I would love to see a video of you making or using Nickel Oxide. (NiO)

[@Justinofalltrades1]

would you have any idea how hard it would be to make Disodium octaborate tetrahydrate? it is used to treat powderpost beetle infestation in wood and is expensive! id like to try to make it. either way thanks!

[@dead0404]

Wheres the link in the description of the tautomerisation mechanism ?

[@NileRed]

Oh I forgot

[@dead0404]

All good man :)

[@starkravenz7008]

what kind of respirators do You normally use for some of your experiments

[@edwardvassell4371]

did you ever try bleach and salt to clean the glassware? works nicely on burnt cookware.

[@NileRed]

Really? Ive never tried that. I guess it is a mild oxidizer.

[@BothHands1]

The salt works as an abrasive, so you don't really need to fully oxidize the material, just loosen it up enough to be removed by the coarse swirling salt.

[@summit-development]

Acrolein: Used in cigarettes AND tear gas Soldier who smokes: Joke’s on you, I’m into that

[@botowner8623]

He got da tolerance 😎

[@Skankhunt-42]

Acolein is also use for Methonin production

[@OmarAPacha]

make a video on menthol

[@bramdegroote7336]

this makes me want to quit smoking

[@LCARS43278]

@13:36 I had to laugh at that spider photobombing your shot!

[@thermosinthesis]

Nice video, Patrick

[@nivmoshe5536]

Hey nile you said the acrolein is found in cigarettes, well is it the reason why everytime you put your cigarette off with cup of water its turn strongly yellow?

[@NileRed]

It could be, but I dont think so. I think the amount present is super small and mostly present only in the smoke. I dont think it would be enough to really see. I could be wrong though

[@ktyzmr]

it's probably nicotine. when it burns it becomes amber.

[@sjoerdnijnatten3411]

do a lab tour PLZ i wanna see your laboratory

[@Toxiq1337]

+Chemistry Lab "lab" 😄 i am like 80% sure that he is not doing most of his experimets in a lab... more like a garage. its more a difference in safety messures than the possibility of doing the experiment itself

[@xPROxSNIPExMW2xPOWER]

If you see closely at the middle flask and the other flask you can see his face lol

[@NileRed]

I had troubles hiding in this one

[@DMCrews1976]

Interesting video but of course anything to do with chemistry is interesting to me. I was wondering if you could make a video on how to make Creatine Monohydrate. I can't find any videos on how its made i have found some web pages that gives a description in words but i want to see it happen step by step on video.

[@2450logan]

You always make my chem class look shitty, but you can only work your way up I guess !! Keep up the good videos

[@butterflygroundhog]

Pesky acrolein, always polymerizing when you don't look at it!

[@darrenburns123]

I watch all your videos... And you know what... I've no idea what the hell is happening in any of them.. 🤣🤣🤣

[@mfkkerrr5364]

well, there's two types of subscribers for nile. one that is really cult and into chemistry and/or working in chemistry field and the other which is clueless ppl who just stumbled upon "fun video with stuff exploding" Xd

[@martinmilner2019]

Love your videos.

[@christopherjose922]

Is it possible to do the double dehydratation of the glycerol using concentrated sulfuric acid?

[@FSM1138]

acrolean 💜💜💜💜

[@benjamin19971306]

what is the reason for the aluminum foil? Love your videos by the way :) want to go into organic synthesis and these really pique my interest

[@robertcrowley6773]

UnKnOwNzzz acrolein is light sensitive. If you don’t protect it from light it will rapidly polymerize

[@torakunoichi]

Don’t really understand ANYTHING in this video but it was cool to watch and learn a little bit about it

[@flaplaya]

1-Octane-3-ol from acrolein? Wow didn't know the low boiling point from acrolein... Love seeing all the expensive ground glassware along with reactions and talk. Good synthesis, you are very smart. What would happen if acrolein was reacted with a dienophile? Diels-Alder cyclization obvious to an unknown product?

[@androidtechgeek]

Last time I was this early, this joke was funny.

[@redsento9094]

Lean💜?

[@milospavlovic4599]

Aren't you supposed to keep the acrolein at +4C in a fridge to prevent polymerization? Anyways, I've seen some fairly old acrolein (like older than 20 years or more) in the fridge that still hasn't polymerized. Naturally, it has to be freshly distilled each time it is used, in a similar way like you did. I am not sure though what does it contain as stabilizer

[@elnombre91]

Looking on various chemical suppliers, acrolein is generally stored with ~0.2% hydroquinone and ~0.3% water as stabilisers, so maybe you should have added a few drops of water to it.