Making Trimethylamine - The Stench of Rotting Fish
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- Опубликовано: 26 сен 2024
- Hey guys, last one of 2016...technically made public in 2017 though. I hope you guys enjoy. If you have any suggestions on how I could use it, let me know - www.strawpoll.m...
In this video, I'l be making triethylamine, which smells like rotting fish.
OrgSyn prep: www.orgsyn.org/...
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Nile talks about lab safety: • Chemistry is dangerous.
Audio work: Kyle Gamble (kylegambleaudio@gmail.com) 
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Oh those were simple times, when Nigel had some sense of smell left
Nigel: _Sniff_ “Honestly, it’s not that bad.” _Sniff_
All of Montreal: _Passes out_
Been their done that and apparently covid-19 makes the smellers not smell so no one can smell what the crazy labrat next door is making anyways.....
"i like to make stinky things"
nile please dont bring your fetishes into the videos
He already has by making a sweetner from his urine
The actual fetish part probably involves feeding the sweetener made from piss to unsuspecting people
@@DronZizzle underrated comment lmao
@@DronZizzle 69 like kes, go na make it 70
@@lordpinochetuttp3819 on.
you could mix the solids before placing the in the flask. trimethylamine can be synthesized by Clarke eschweiler reaction from ammonium chloride, formaldehyde and formic acid.
+zodd0001 true! Also I always forget to mix things beforehand...
@@NileRed you seem to have learned to in the last 5 years 👍
@@NileRed I remember about 2 years ago I was doing this reaction in a PTFE coated glass beaker and for some reason the beaker said bye and exploded 🤦♂ anyways RIP beaker. And later made a new batch and turned it into trimesium or trimethylsulfoxonium.
JESSE the metlymine must flow
Ayy that's my name
methylamine?
I thought exactly the same lol
Its going bad, we have to cook it all NOW!!!
Yea science
people in the future know nilered as "the stinky compound guy"
That tile is an honor
Can you please make a video on how to synthesise thioacetone?
@@NileRed not wrong
Nilered - “The Stinky Compound Guy”
Joe Barnard - “The Carbonated Milk Guy”
ExtractionsandIre - “The “ *YELLOW CHEMISTRY BAD* “ Guy”
Whatever next?
@@NileRed hey Nigel, would you ever go into the chemistry of nicotine type chemicals and their use and manufacture? I have been reading on my own time and I see a lot of possibilities for good uses
"I made a ghetto dessicator"
Spoken like a true Chemist. XD
THATS RACCCISSSS
@@dphorgan no, u.
A 55 GALLON drum with molsiv desiccant in it is all you need, just place the body, er item in the proper size container and pour desiccant till it's covered or if it's liquid a cloth bag or other porous material will do.
"I like to make stinky things"
-Nile Red 2017
“I like to make stinky things”
Now that was fishy.
Hey NileRed! I enjoy your videos, and they are always a high point in my day. You inspire me to follow my dream to be a chemist when I am older. I don't understand a lot of the stuff in your videos, but they're still fun to watch. Thanks for making great videos.
+Link McLaughlin :)
17:10 That's a very pretty crystallization.
Next video: Extract stress from my life.
And now, after recrystallisation, we have pure crystals of stress. In order to test it, we’re going to pay a visit to our enemi... ahem... test subjects, and put a few drops of a concentrated solution in their food and drinks, and see how they stress out.
There's actually no practical reason to extract stress because a near-pure source can be found in the tears of every 2nd year Medical student.
Chemical extractions usually destroy the parent material.
Add 4 grams of tetrahydrocannabinol
@@xXponyinthestarsXx yep lol
I had to pass a small chemical plant each day on my way to/from work a few years back. They used to make trimethylamine there and the stench was absolutely unbearable during summer, so much my nose would hurt. In fact, on some hot summer days, I can still smell it from a mile away when they open the vats.
make Nile Red
i come from the future and i have good news for you
So the next step in this reaction is adding my DNA to a cloning machine. After this the next step in my reaction is creating a evil army of 100s of me's
Video idea - chemical sources. The easiest or cheapest ways to get things, various OTC sources of re-labeled chemicals (sulphuric acid from drain cleaner), chemicals that you can only really buy sold as the chemical itself (nitric acid), etc.
And you can also talk about the easiest/cheapest ways of synthesizing common reagents that you can't normally buy. Although you can read about where to get many things online, the information is often out of date or region-specific. That is the case for potassium nitrate - it's now very hard to get in any quantity in the US unless you are a business and can order in bulk, although there is the notable exception of stump remover. Same for ammonium nitrate - Cold packs are a source, but most of them have a mixture of ammonium nitrate and some other things. This kind of knowledge is mostly gained from experience and could save people a lot of money spent buying technical grade chemicals when they could get a much cheaper OTC product.
travis dunn it depends a lot on the country, here in spain I have never seen H2SO4 drain cleaner, it is always a solution of NaOH, and cold packs, havent been able to get any nitrates out of them, always NH4Cl
In ebay you can buy 1 pound of KNO3 for 10$, however it costs me arround 15 or more because of shipping
Yes, that's true. Europe is generally worse than the US in availability and price.
Where I live, I can't buy methanol, even producing it is illegal, but I can buy red P no questions asked.
Kwaki wow that makes no sense at all... where is that?
Serbia, all because people put methanol into alcohol because you need less of it to make it strong and it's cheaper so they outlawed the thing, you need a permit to acquire it. 43 people died.
Trimethylamine is one of the constituents of the Amorphophallus titanum smell. That’s why many people say it smells like rotting fish when it blooms.
Hehe, phallus
We use tripropylamine at work to generate ECL signal in ELISA testing. It also smells like fish.
NileRed is back to making stinky chemicals, what a great start to a new year!
U Wot M8
Weedus That’s methamphetamine.
Buck Dog no it isn’t. We’re still waiting on that one as of yet
No one was hurt, but a strong smell of fish hung in the air.
thioacetone should be next =)
How about no no no no
@Regret is my middle name ya. It's was in Germany. People needed medical help from 3/4 mile away...... LOOLOLL
@Regret is my middle name That's from Esso in 1967 "Recently we found ourselves with an odour problem beyond our worst expectations. During early experiments, a stopper jumped from a bottle of residues, and, although replaced at once, resulted in an immediate complaint of nausea and sickness from colleagues working in a building two hundred yards [180 m] away. Two of our chemists who had done no more than investigate the cracking of minute amounts of trithioacetone found themselves the object of hostile stares in a restaurant and suffered the humiliation of having a waitress spray the area around them with a deodorant. The odours defied the expected effects of dilution since workers in the laboratory did not find the odours intolerable ... and genuinely denied responsibility since they were working in closed systems. To convince them otherwise, they were dispersed with other observers around the laboratory, at distances up to a quarter of a mile [0.40 km], and one drop of either acetone gem-dithiol or the mother liquors from crude trithioacetone crystallisations were placed on a watch glass in a fume cupboard. The odour was detected downwind in seconds"
So the equivalent of pulling a fire alarm or screaming bomb in a public theater in chemical form. Yeah....
nah...
It's just a prank bro
For the gas absorption, you might want to put a second bubbler in the chain - put it the opposite way around, _before_ the bubbler that's the "usual" way around. This improves absorption and helps prevent suck back.
So, to clarify: connect the two dip tubes together and connect the gas output from the distillation apparatus to the top of one of the bubblers.
You could also place a U-tube filled with solid sodium hydroxide before the absorption bubblers with this arrangement to prevent HCl from diffusing back through the apparatus.
Hope this helps, have fun and take care!
Those Keck clips (clamping the glassware together) are often made of polyoxymethylene, basically paraformaldehyde with a higher molecular weight.
I like to make stinky things too. In fact I'm making a big one right now on the porcelain throne
Travis Heck I like to make stinky things too. In fact, Im growikg a very big one. My son.
Travis Heck Porcelain throne . Great expression
hahaha lol
Splashing Hershey squirts down the ole ceramic water slide
@@hunnitmanjuuve2404 💀
"Ghetto Desiccator", That's my rapper name lol
Hi, I work in the chemical coatings industry and we use this for ophthalmic coatings, including products which Oakley purchase. We mix these with cyanoacrylates and organosilanes.
Nile: "I like making stinky stuff."
Also Nile quoting someone: "Since it's your favorite pastime making stinky stuff. - I don't know why people think that."
I store my TMA-HCl at -20*C under dry argon which stops it turning into slush or smelling. I made mine using [14C]-formaldehyde as I needed mine carbon-14 labelled so radiolysis products form hence keeping it cold (note I do this for a living, hence why labelled!). Bowls of acid left out will soak up the smell if you are struggling.
"But still, 7 grams in a minute is quite a lot."
Wow, maybe I should use this to dehumidify my room!
"After doing this prep, my workplace stank for something like three weeks."
OK, never mind.
that stinks
Niceth like
" Bacterial vaginosis" LOL. In the civil war, the soldiers used to go to visit the prostitution houses, they followed their noses to the locations.
If you think that's hygroscopic try to synthesize some ionic liquids. They turn into puddles of water in seconds of exposure to humid air. Love your work man :)
did someone say methylamine? my inner walter white woke up
I read about fish and what the chemical is when they start to stink, so I wondered if there was a NileRed video of it. I was not disappointed :D
Thanks so much for keeping the knowledge alive. Chemistry is life.
And, quite literally, life is chemistry.
HAPPY NEW YEAR! the first thing nilered did this year: MaKe TrIMetHyLaMinE
Nile red: I like making stinky things also nile red I don't know where you guys got the idea that I like to make stinky things.
i don't know why, but "ghetto dessicator" is probably one of the funniest phrases in the english language
Try adding your solid using a waxed weighing paper by rolling it into a funnel works much better!
10:47 OKAY, now you got my attention
I'd love to see a chemical or reaction that smells moldy or musty or dusty. Something that smells like a wet basement full of mold❤
S K I'm gonna vomit from reading those last few words.
Phosgene smells like musty hay
@@JoelRG727 dunno theres two kind of moldy smells. An humid basement where you have really good memories, like the slight smell thats brings those memories out. And then straight up disgusting rot
@@adorabasilwinterpock6035 don't forget its a chemical weapon aswell
Make some Trichloroanisole. It's responsible for "corked" wine and in higher concentrations is described as smelling like a wet basement or moldy newspapers. And its odor threshold is in the parts per *trillion* range.
The suckback can also be prevented by using a second bubbler between the system and the bubbler.
You can also use Phosphorus pentoxide (P2O5) as a drying agent in desiccator. It is very efficient and easier to handle than sulfuric acid.
You can make DMT from trimethylamine
With bromine and a derarative of indole-3-carbinol (if you have I3C, dehydroxylize it first)
@@killthesource4740 You can literally found instructions and papers on how to synthesise literally any drug if you search enough
15:20 forbidden cheese cake
trimethylamine free base is an amazing organic solvent friendly relatively strong base for some complicated and delicate syntheses. I don't know the market price of it outside of academia but it's worth holding on to it or freebasing it in a video without the use of water. just a thought.
ruclips.net/video/m9lzToGWsn0/видео.html
for some reason it really bothers me that hydrochloric acid is so often called and sold as muriatic acid, pisses me off
whatarewedoing Why does it piss you off? It's not wrong.
whatarewedoing its called "strong water" in spain, that does sound stupid, muriatic acid is the historical name, so I dont know why it bothers you.
Well in Lithuanian it's called "Salt acid" which doesn't make much sense either
Daumantas Gaidelionis That does make some sense. Table salt is NaCl, when neutralycing HCl with NaOH you get NaCl, and you can get HCl from salt.
Muriatic means basically "relatrd to salt", "related to brine" or something along those lines, so muriatic acid and salt acid are pretty similar ways of calling it after all.
We have to thank this to the ye olde chemists, aka al-chemists
Actually now when you explained it in detail it does make more sense, but still, using it as table salt wouldn't be the best idea
Thanks for doing these vids Nile, very informative - question for you as somebody that nose: out of trimethylamine, cadaverine, and putrescine which is the most obnoxious smell? also is there a cheat to produce the trimethylamine using just heat like with the other two? not to concerned about the quality of the yield - just so long as it stinks :-)
Yeah wtf
?
NileRed yea wtf bro...
NileRed wtf
NileRed bruh.....wtf??
wtf...
The worst thing in the world is when the stir bar disengages and starts flying wildly around the flask
In my organic chemistry class in college our final project was to identify an unlabeled chemical given to us using methods we had learned throughout the semester. We had three labs to identify your compound, but I think I got the easiest chemical to identify. With just a waft test I knew I had Trimethylamime and was done in the first lab period 👌🏼.
Can trimethylamine dissolve alkali metals like ammonia can?
Eyyyooo another dank video! Would you ever think about doing some videos on glassware? I guess you probably don't want to encourage people that don't know what they are doing toooo much.
Great work, you could use it to make some phase-transfer catalyst such as benzyltrimethylammonium chloride, although easier would be to prepare benzyltriethylammonium chloride from benzylchloride and TEA (triethylamine) considering TEA isn't gas and then utilize it in some phase-transfer catalyzed reactions :-). I think it would be very interesting chemistry to play with.
Or choline hydroxide as Tomás Allende suggested.
You could try to mix things efficiently by using a Ziploc bag just like you did in the preparation of benzene ( Where you mixed sodium benzoate and sodium hydroxide).
Formaldehyde has a very pleasant smell i remember it was in my school Chemistry lab and bottle was leaking hahaha
The DIY desiccator probably would've worked better with a large open top internal vessel.
like making stinky stuff. I guess only true friends remain when your hobby is this:)
0:51 Me on the toilet: I like to make stinky things.... 🤣
Perhaps you could use the trimethyamine in a kornblum oxidation reaction, usually triethylamine is used however i have seen examples where trimethylamine was substituted. Not sure what compound you could do the kornblum oxidation on but it is a cool reaction and would adds some more versatility to your arsenal.
Any ideas of what makes the stink when you mix coffee with sodium carbonate? I use this mixture in film developing and it smells like rotten garbage.
so many prank ideas
When I first started watching nile red/nile blue, I thought he had a very dead and depressing voice. Now that I’ve been a fan for years, I wouldn’t have it any other way! Keep up the great work!
You should try some sodium thiosulfate chemistry. You could dissolve gold or even show how it's used to treat cyanide poisoning.
Love the idea
Does this help plants grow because of the nitrogen? I've heard that if you put a rotting fish under crops it'll help it grow
Z if the plant could metabolise it, probably yeah
The smell is a side product not the actual source. The nitrogen cycle is a little less complex and pretty straightforward when in comes to plants. A dead fish lends other nutrients the plant can utilize like sulfur, phosphates, calcium, iron etc as well as being exponentially cheaper to use. :)
Brian Reddeman Huh, thanks! Really interesting stuff
It's what plants crave
But nile you can prepare it easily by reacting the ammonia with methanol in the presence of a catalyst
"i like to make stinky things"
* pauses video and scrolls down to comments
yup.
“I just want to make it because I like to make stinky things”
_-Nile 2016_
If trimethylamine picked up 7 grams of water from humidity in about a minute it sounds like it would make an excellent drying agent, perhaps in your vacuum desiccator for stubborn chemicals🤷♂️ I dunno if it fumes a lot or how much it sublimes so it may not be good for this purpose as it may react with your product also it sounds like it is extremely odorous so it may not be worth the headache....but you asked for some suggestions and this came to my mind almost instantaneously
Random thought, if it grabs water that strongly yet it can be used with vacuum to keep drying - if water is contained would it eventually completely dry room air?
That might be far more efficient than most of air dryers out there, depending on how much power vacuum use. :P
Formic acid can actually act as a reductant for the imine intermediate, since it can donate it's two hydrogens and decompose into CO2, so that's where all the CO2 comes from
"I just like making stinky things" a true organic chemist
Legit have no idea what you’re on about half the time, live watching your vids tho
Trimethylamine can also be isolated (along with its lower homologs) from herring brine...
20:30 Drying the substance this way isn't very effective, since there is no good exchance of the air, which is saturated with water vapours, due to the narrow neck of the flask.
A round crystalizing dish provides better air exchance.
Potential use: reacted with benzyl chloride to make Me3BnNCl, which is an excellent phase transfer catalyst which may be of use in other syntheses.
6:20 "in the presence of hot water, the formic acid degrades to CO2 gas" - this is factually incorrect. Please rectify thus: "in the presence of the imine, formate acts as a reducing agent, donating a hydride anion and releasing CO2"
This can also be corrected in the reaction schematic shown on screen from 5:59 to 6:37.
Also it seems likely that the iminium cation is initially reduced by the anion of methanediol (i.e. hydrate of formaldehyde) donating hydride.
Also, at 7:50: "on top of this, excess water also breaks down formic acid that's formed."
This doesn't make any sense to me! How does water break down formic acid?? AFAIK, dilute formic acid is pretty stable.
Don´t worry man,,fortunately procedures in this sites are not correct, thanks God, congratulations! I see that you are a chemist or advanced student, welcome at a coleague. Many times are present some kind of Breaking Bad boys here.
I am not surprised of why he almost gets a process 2% efficient in almost half of the videos.
Imagine telling someone that they smell like trimethylamine, what a burn.
whats in a powdered pocket warmer, and can u use that powder for something cool? if so thats awsome, keep up the good work
Yes Nile, Start a new year with a stink!
19 hours ago? The video was posted 2 minutes ago :o
NOTIFICATION SQUAD
WHO UP
+MegaKiloBite Something seems....fishy.....
We've got ourselves a time traveler.
Bacterial vaginosis, yup, definitely needed that image/smell in my mind, and cursed knowledge.
Congratulations on 100k subs!
Your definitely a budding chemical research guy....Great videos.
You're
7ml water pulled from the air in a minute is pretty impressive.
Phosphorous pentoxide or nitric anhydride are good drying agents as well
It's my birthday today. And this video came out ! Awesome
Happy birthday!
Nurasake thanks :)
Did the timelapse function make a series of stills? If so, they're only a bit more labour intensive, but better quality than most precompiled video timelapses. I have a workflow for those . . .
It was really good, where I can read article of this?
"Ferb, I know what we're gonna do today"
Now we know how all the legend of aquaman really began
The stench of methamphetamine is often associated with bromine and barium
Mircea Crafter BReaking BAd!
Could you make a video on how to extract eugenol from cloves, cinnamon, nutmeg, or other eugenol-containing herb?
Oh I did this one for my first organic chemistry lab
Nile "I like to make stinky things" Red.
The music at 12:37 was driving me crazy.
Good work Nigel
another great episode. I find this apparatus awesome to look at! The apparatus is becoming as awesomevas the chemistry your conduct. Bravo
Thanks!
“I like to make stinky things” is my sisters motto
THANK YOU! I was actually thinking of making this, now I have help =D
when are u continuing the series of asprin
Elie George he might have gave up cause he wouldnt have enough to make it :/ that or hes taking the time to make more idk...
Try making thioacetone
15:21 the forbidden latte
Where is the video on the synthesis of methylamine? I can't find it
No. It's not. Because trimethylamine has boiling point at 3-7 celcius. He made Trimethylamine.HCl.
Lets see the production process of Ethylenediamine and show how it can form complex's with metals, just one of its many uses.