> chemistry > amines > making-trimethylamine-nilered

Making Trimethylamine - The Stench of Rotting Fish

NileRed - 2017-01-02

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.
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http://www.strawpoll.me/12045765

OrgSyn prep: http://www.orgsyn.org/demo.aspx?prep=CV1P0531

Audio work: Kyle Gamble (kylegambleaudio@gmail.com)

Nile talks about lab safety: https://youtu.be/ftACSEJ6DZA

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ZodaChem - 2017-01-06

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.

NileRed - 2017-01-06

+zodd0001 true! Also I always forget to mix things beforehand...

倒disconnect. - 2017-08-30

"i like to make stinky things"
nile please dont bring your fetishes into the videos

Boredaf - 2021-03-26

@LordPinochetUTTP ono

Boredaf - 2021-03-26

@LordPinochetUTTP o on. Ooo o o o o o o. O

Cheshire Carolynn - 2021-05-02

@Boredaf you alright?

Mr man - 2021-09-21

@Cheshire Carolynn he’s definitely not ok

Einar Pers Øygard - 2021-09-25

"I dind't want to make a precursor to THAT!!!.
I just wanted to make a smelly chemical!"

Link McLaughlin - 2017-01-06

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.

NileRed - 2017-01-06

+Link McLaughlin :)

Sol - 2017-08-29

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.

honorablemention - 2017-05-07

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❤

Adora Basil Winterpock - 2021-05-08

Phosgene smells like musty hay

Magus Perdé - 2021-08-04

@Joel 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

Hidden66 - 2022-01-06

@Adora Basil Winterpock don't forget its a chemical weapon aswell

Biospark88 - 2022-02-28

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.

Pete Venuti - 2022-09-21

What's that "smells like a library" smell? That smell that 100-year-old musty books get... What chemical combination of chemicals makes that?

norlesh - 2017-11-11

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 :-)

Gordon Cracknell - 2017-01-18

JESSE the metlymine must flow

HYVE - 2022-05-05

@Chris P. Bacon the only good TMA is TMA-2

HYVE - 2022-05-05

@Achilles Lade He prolly meant triMETHOXYamphetamine which does exist

Peregrin Took - 2022-08-23

🤓

Video Game Muncher - 2022-10-07

@Justin Hamilton it is

SchMarcEL - 2022-10-12

Mr Whité! i require the methé!

Alex Welch - 2017-02-13

We use tripropylamine at work to generate ECL signal in ELISA testing. It also smells like fish.

Will Story - 2021-05-19

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.

U Wot M8 - 2017-01-02

NileRed is back to making stinky chemicals, what a great start to a new year!

Starbuck 7410 - 2017-01-03

U Wot M8

Mikhail Kalashnikov - 2020-04-08

Weedus That’s methamphetamine.

A Tap Helicopter - 2020-06-14

Buck Dog no it isn’t. We’re still waiting on that one as of yet

Dio - 2019-10-17

Could you isolate the bromelain enzymes in pineapples and use it to break down some meats over time?

Chomzik - 2017-01-02

You can also use Phosphorus pentoxide (P2O5) as a drying agent in desiccator. It is very efficient and easier to handle than sulfuric acid.

Dakota Sleeper - 2017-01-06

whats in a powdered pocket warmer, and can u use that powder for something cool? if so thats awsome, keep up the good work

The Spin Doctor - 2019-06-23

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.

jared garden - 2017-01-03

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.

UniverseCafe - 2017-01-05

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.

Dami Ikeduba - 2017-01-02

"I like to make stinky things"

-Nile Red 2017

XXCoder - 2017-01-03

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

meagain2222 - 2017-01-11

Your definitely a budding chemical research guy....Great videos.

Henry Yang - 2017-01-04

people in the future know nilered as "the stinky compound guy"

Roberta Williamson - 2021-05-06

@A Tap Helicopter What next? liquid ass beat him to it, or maybe Surstromming

Anti-Armadillo Society - 2021-08-09

@NileRed 4 years later, and nobody has mentioned the typo in this reply.

My Real Username - 2021-08-13

@A Tap Helicopter styropyro- the *everything I do would kill you* guy

ok - 2021-09-19

@Anti-Armadillo Society i noticed that too

Me Robo - 2021-10-02

As somebody who was introduced to NileRed in the future (at least as seen from the point in time when your comment was written) I can tell you that you weren't too far off, considering that I was introduced to him as "famous piss-chemist Mr. Red" (or something close to that)

sir9integra9jr - 2017-09-18

"I just like making stinky things" a true organic chemist

Asdrubal Vect - 2017-01-02

No one was hurt, but a strong smell of fish hung in the air.

Karthik Shankar - 2019-05-17

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).

Green Pumpkin - 2017-01-02

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.

Green Pumpkin - 2017-01-02

Or choline hydroxide as Tomás Allende suggested.

MarcCG - 2017-01-02

You could use it for a Hoffmann elimination, in theory it's a way to create terminal double bonds but I've never seen it.

Sonicthehedshot9 - 2017-01-04

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.

Dick Butte - 2021-10-06

https://youtu.be/m9lzToGWsn0

Kenneth Studstill - 2017-01-04

Can trimethylamine dissolve alkali metals like ammonia can?

Spooky Wizard - 2017-01-02

THANK YOU! I was actually thinking of making this, now I have help =D

12thealchemist - 2017-01-03

Potential use: reacted with benzyl chloride to make Me3BnNCl, which is an excellent phase transfer catalyst which may be of use in other syntheses.

AguaFluorida - 2017-01-07

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!

chromatis - 2021-05-15

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 . . .

Ahmad Alhuwaish - 2019-08-04

“I like to make stinky things”

Now that was fishy.

GamersBar - 2017-01-03

Im pretty glad i dont have the smell like fish disease , love the videos though keep em coming!

Jean-Frédéric Rolland - 2017-01-19

Thanks so much for keeping the knowledge alive. Chemistry is life.

Bein' Ian - 2021-08-12

And, quite literally, life is chemistry.

K1naku5ana3R1ka - 2018-08-04

During the reaction, why was the stir bar flying around everywhere instead of spinning in the center? Might have been the bubbles, but it kept doing that even after the bubbles died down.

travis dunn - 2017-01-02

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.

iNsaNiTY_Crona - 2017-02-24

Indeed it's hard to get your hands on chemicals in the EU. In germany you literally have to fill out 5 entire contract papers if you want to buy phosphor (Red), chlorine etc. but also things that seem quite usual like ammonia or hydrochlorid acid which is a pain in the ass for anyone who likes to do chemistry on their own.

htomerif - 2017-10-14

You might want to watch doug's lab videos. He seems to concentrate on making stuff from consumer products. I'll say though that even videos from a couple years ago may be out of date as to whats been banned or controlled in the US. Even derp chemicals like sulfuric acid and potassium nitrate are off the shelves in most stores where I live.
You'll probably have to do lots of distillation to get most things like benzene and toluene as they're usually mixed. Then you get to introduce yourself to the wonderful world of azeotropes.

Fedico7000 - 2021-04-28

Thnx for predicting this channel

Konrad - 2021-05-20

They cannot be bought for a reason as many of them can be used to produce drugs or high explosives

Konrad - 2021-05-20

@Kwaki in my country we can buy only 100g of Red P per year

joed596 - 2021-05-23

Very interesting 🙂 Brings me back to Org. Synthesis days 👍🇺🇸

Umbrus - 2017-01-02

awesome :D question: why do you use a glass stir rod and a metal spatula? wouldn't it be easier to just use the stir rod to, well, stir the powders? i've noticed you do this a lot, and i'm just curious why you use one over the other

BaalAdvocate - 2017-08-28

I tried synthesizing this in my lab. I was able to successfully initiate the reaction and bubble it through HCL. When you boil off the HCL in the final process (obtaining the white powder), the smell stops. How does one release the Trimethylamine from the salt form? I managed to make myself reek, but the final product seems more or less odorless. Any tips?

Alex - 2020-09-12

Don't quote me on this, but I believe you react it with a strong base (sodium hydroxide) to make TMA freebase, sodium chloride and water. You can then extract the TMA oil using a suitable organic solvent such as dichloromethane or chrloroform. Never done it myself so I don't know if that's how it would be done

The Phantom Safety Pin - 2019-03-11

"I made a ghetto dessicator"

Spoken like a true Chemist. XD

David Horgan - 2019-03-18

THATS RACCCISSSS

Fedico7000 - 2021-04-28

@David Horgan no, u.

Roberta Williamson - 2021-05-06

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.

GD lifesteal - 2021-01-02

HAPPY NEW YEAR! the first thing nilered did this year: MaKe TrIMetHyLaMinE

Malaroli - 2020-07-11

But nile you can prepare it easily by reacting the ammonia with methanol in the presence of a catalyst

kevin chandler - 2017-01-02

Try adding your solid using a waxed weighing paper by rolling it into a funnel works much better!

Randy Pullman - 2017-01-05

another great episode. I find this apparatus awesome to look at! The apparatus is becoming as awesomevas the chemistry your conduct. Bravo

NileRed - 2017-01-05

Thanks!

The Killer Fitness - 2017-01-02

Hey I'm a chemistry major right now, I'm just wondering what you did to know the amount that you do. Did you get a chem degree or is a lot of this just practice and experience based? Anyways, love the videos dude. Keep it up

Combatant5 - 2019-05-30

You could try reacting it with RFNA, IIRC they are actually hypergols.

Nimmen - 2021-07-04

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

Patrick Donoghue - 2017-01-02

Hey, I've bought my own glassware for doing experiments, any ideas what I could do to start off and get used to the apparatus?

S.A. Smith - 2017-01-03

Would depend on what glassware you've got and if you have a controllable heat source (heating mantle, hot plate etc. Bunsen burners can make things hot very quickly and uncontronably).

Salts and Sugars or non-toxic organic compounds. You could make something aromatic, but you'd need Phenol, which is a carcinogenic compound.

o-o - 2021-08-03

“I just want to make it because I like to make stinky things”
-Nile 2016

thebestofall007 - 2017-01-02

Could you make a video on how to extract eugenol from cloves, cinnamon, nutmeg, or other eugenol-containing herb?

Misauti Voros - 2022-02-17

Oh I did this one for my first organic chemistry lab