Making denatonium benzoate - the world's most bitter chemical
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- Опубликовано: 12 мар 2016
- Hey guys, today we're going to be making denatonium benzoate from lidocaine, benzoic acid and benzyl chloride that I made in previous videos.
Benzyl chloride video: • Making Benzyl Chloride
The intro video was made by user Linus Tuttle (ruclips.net/channel/UCH7P.... Thank you!
The music for it is from Incompetech (Severe Tire Damage Kevin MacLeod (incompetech.com)
Licensed under Creative Commons: By Attribution 3.0 License
creativecommons.org/licenses/b...)
Procedure adapted from: www.google.com/patents/EP18248...
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Nile talks about lab safety: • Chemistry is dangerous. 
Наука
I used this to keep the horse from chewing on our trees.
Cody'sLab Hi Cody!
Vix vapour rub works too
Cody'sLab that's awesome
i think i will use Denatonium Benzoate to stop some crazy peoples form eating/drinking me
mercury How would you drink it yourself? Maybe a dummy straw?
But I’d probably forget about it and getting the taste stuck in my mouth for weeks.
Nile Red always uses the most scientific measurements like, "a bunch"
+Kid Kirby Perfect SI unit ;)
At least not something horrible like fluid ounce.(No, as I'm from central Europe I do not even know how much that is exactly, I think somewhere in the region of 1 liquor shot)
namibjDerEchte The US uses freedom units, You use heathen units. Freedom units > heathen units.
Yup, nilered is quite sloppy. But we don't mind.
Did you see that his stirbar is actually a paper clip?!
Your search is over. This is the only NileRed video with an intro. Congratulations
Really?
@@addyshorhnr3544 yes
This is a monumental discovery
Oh cool
Hahahaha. Thank you. I literally was going to search.
You don't need an intro, you're classy already
+DerFlugzeugTV I probably wont include it in the future videos, but it was made for me and I wanted to credit the person for making it. They took their time to do it and it was the least i could do
+Nile Red keeeeep it is awesome
+Nile Red I'd suggest using it in about half of the videos, as some people like it and some don't.
Chester TheMolester Yh I agree. Well tbh I think no intro necessary but if you want one then at least include your logo and stuff
@@NileRed You should've kept the intro it looks so cool man.
Your story about bitterness was still less insane than my organic chemistry prof's story.
He made a small amount of sweetener(I don't remember which one, but he said it was about 10.000 times sweeter than normal sugar) for an experiment, and decided to try a little bit of it. It tasted sweet but not insane, just like regular sweetness. He then tried to wash it off, surprisingly it didn't wash off. A day later, still, everything tasted sweet. A week later still the same picture. He couldn't get the sweetness out of is mouth for 3 weeks. Literally everything he ate was sweet for 3 weeks.
+MrGurkentomate that is crazy. At least it was enjoyable though?
He could have drunk straight up black coffee for that whole period of time to assert how much of an alpha male he was.
What is it?
@@petevenuti7355 Probably neotame, it's roughly 10,000x sweeter than sugar. I believe it's the 3rd most sweet substance out there
Did he accidentally make miraculin, the stuff on miracle berries?
I think the reason the multiple acetone-evaporation cycles worked is that you were removing some water each time. Wet denatorium benzoate was probably soluble in acetone, but the dry one, much less.
+supersmashsam That might be possible!
this is a pretty fascinating and scary illustration of how, even when taking precautions when working with carcinogenic or other dangerous chemicals, a small amount still gets on your skin and even in your mouth. Glad I'm not a chemist!
You mean, a good illustration of why wearing gloves is important?
@@kirayoshikage4057 at 11:10 he says some gets on your mouth just from the fumes that evaporate. Unless you do everything in a fume hood, which most chemists don't, you are still getting some in your mouth
@@roblarssen249 Not my problem if "most chemists" ignore the fact that chemical reactions release fumes that are possibly toxic.
@@kirayoshikage4057 then you clearly have never worked in chemistry since even a chemistry college student could tell you that it is impossible to do every reaction in a fume hood. There isn't that much space and you are severely limited in what you can do by what you can physically get in a fume hood. Most reactions happen at the bench and only those most likely to be dangerous happen under the fume hood
@@roblarssen249 you clearly never worked with chemicals if you're scared of every single one of them.
I had one of those compressed air cans get punctured a while back in my apartment and for the better part of a day while I aired out my plave, the air itself tasted bitter from this stuff - Really amazing how potent it is.
Yeah I have a more embarrassing but similar story. I used to huff air dusters and they had denatonium benzoate to discourage that. Usually I would use a balloon but one day I decided to just inhale straight from the nozzle. I almost threw up and was tasting it for the next 2 days. I can still remember the taste, yuck.
How long did it stick around? Did it take long to dissipate? My carpet is full of the crud at the moment…
These videos remind me of the organic chemistry lab in undergrad. As a grad student in RNA biochemistry my chemistry has gotten really rusty - so I always stop and look at how I would explain the reaction, how I would go about it etc - great revision!
The stir bar looks vaguely paperclip like.
Jake Kim It is
Indeed
It is the stir bar for the oil Bath
The stir bar is in the round bottom flask --- the shadow on the hot plate makes it look big and paperclip-like.
It's really Clippy from Microsoft word.
In all seriousness though, the paperclip is used to stir oil bath to evenly distribute the heat. There's another stir bar in the round bottom flask.
I watched a whole bunch of videos from 2010-2019 but I haven't seen an intro.
Based on another comment it looks like he only used it once as a favor to the person who created it.
Brandon, I figured it out, I finally did it ! “Nodnarb “ IS JUST BRANDON IM SO STUPID OMG
@@bradleyholland4984 WHO'S brandon!?
@@Tommo. Nodnarb is Brandon.
This happens quite frequently to me. Especially when working with toluene, its really hard to fully remove most of the time as toluene has such a low boiling point. This means that often tiny amounts stick to the otherwise clean product, sometimes even after some washing steps (If you were gonna do it again I would wash it a little more, maybe using something less polar like hexane). One thing I learned to remove the remaining toluene is to add a little bit of low boiling point solvent (in my cases often chloroform or dichloromethane) and then quickly reduce the pressure below the boiling point using a rotary evaporator to quickly pull off the solvent which might strip some toluene with it. oc be careful so you dont create a mess. I believe that something similar happens when adding a little bit of acetone to the allready hot syrupy liquid.
nice video. interesting substance.
like the intro.
"... it's honestly probably better to use a seperatory funnel. But I decided not to for some reason..." comments often remind me a bit of myself when I'm in the lab ;)
“Ill try to remember to post a link in the description but ill forget” Im dying 😆😆😂
Wow, really interesting compound, I could only imagine how bitter it is. Also, kudos for your new mic and intro. Keep up the good work, I can't wait for more videos!!!
Glad your channel is growing and nice intro
+Janusz Januszowski Thanks!
I work at an ice cream factory and we use bixtrex in our pasteurization process. It’s a fail save so we know if anything goes wrong. I tried some straight up because I’m dumb, and yeah extremely painful bitter and then that taste lingered for days. Don’t mess with it 😂
I thought Denatonium Benzoate was bitter but then I remembered how my ex was.
+zubmit oooooo
oh my god! oh my god! oh baby a triple! oh my! oh my God! MLG!!
@@theterminator3907 this made me physically cringe.
@@NileRed So basically, you made Denatured Alcohol...am I right?
@@theterminator3907 yikes
Best chem channel everrrrr
I thought nurd rage was the best, but when I found Nile Red about a year ago, I changed my mind totally. He releases a lot of videos, all of the videos are high quality and he does a brilliant job of explaining the steps and what reactions are taking place.. Only problem I have with this channel is that he doesn't have enough subscribers. This channel deserves a lot more.
+Terry McAnear Thanks :)
4k, awesome intro and quality active content. What's next?! Amazing Nile Red. Keep it up!
Oh, I forgot, new mic?
+ZeroGames intro is gay
billied_2003 Thx for the feedback! :D
+ZeroGames wtheeck
+billied_2003 me too
Hate someone? Pour the whole bottle into his meal!
Put a small amount in their toothpaste, salt shaker, pepper, sugar, water piping, shampoo, soap, ect.
ᴠᴧᴨᴛᴧᴃᴌᴧcᴋ lol
Put in a woman's lipstick, ruin their dates.
+Cyberw4y omg xD
@@Cyberw4y Put it in her douche water, really ruin her dates!
At 9:33, you labeled denatonium chloride as "denatonium hydroxide." Great video, by the way!
The quality of your videos just keeps improving.
That was the cheesiest intro I have ever seen. I love it.
+NeedSkillNow haha thanks
+Nile Blue wha-
+Ben Sullivan XD
@@NileBlue what
Linus Tech Tips worthy?
I never thought you'd get an intro, and you finally got one. It especially suits you.
+Xylofuse This. I've been hoping form some grignard synthesis
Hey Nile, I've been watching your videos for sometime and I really like them, and are one of the things that made me REALLY interested in organic Chemistry. They also helped me with making a project that I have to do in my Organic Lab course :D THANKS!!
I would like to see the Calcium Acetate from Vinegar and Egg shells! and for future videos Nonivamide and Vanillylamine have my votes.
I also second +TheRedKnight 's motion for organometallics reactions if you can.
+Emanuel Rivera Torres I am glad you enjoy! The video you want will be out eventually :)
+Nile Red Hey Nile! I'm really enjoying your videos...
A question, how much money have you spent on equipment so far?
InbredDucks I would go with "a lot". I dont have a dollar amount though. At least a couple thousand dollars on glassware and chemicals
I really enjoyed science in school but I didn't do well because tbh didn't really have friends and there was a lot of group work. But your channel reignited my love for science and I really appreciate it.
You and me both. Nothing like hearing the teacher say, “Divide yourself into groups,” or “Find a partner,” to cause soul-crushing depression.
The degree of consistency in your video production is incredible, I know you changed filming hardware and location since, but your narration was exactly the same, and the production quality was already top notch!
We should fix a goal for Nile, the day he puts al reagents in the beginning of this video, he would get some sort of bonus.
Like a free hot plate paid for by patreon?
I think he does it on purpose.
When I was a child, my mother used one of those nail preventative nail biting polishes on my nails. I didn't know why I had a bitter taste in my mouth after eating or biting my nails whenever I felt anxious, but about 20 years later I know something for sure: that stuff didn't work in my case.
Those nail polishes don't really work if you regularly eat bitter foods like acorns or drink bitter things like black coffee. If anything, my nails ended up between my teeth more because the taste helped me concentrate.
@@callfororion8846 I don't eat or drink anything bitter on a regular basis, much less when I was a child. I believe that the reason the nail polish didn't work with me is that it was directed at the symptom, not the cause, which is my anxiety.
That stuff doesn't work in any case. It is as simple as telling your child not to do it in the first place.
The intro was very surprising to see
Nice work Nile
theese vids are amazing. keep it up nile red!
"I realized that it wasn't supposed to"
I'm done :'DD
Hi Nile. Can you do some different thermite reactions to capture different metals like manganese, silicon etc. Keep up with good work!
Love that new audio! Basic Copper carbonate and methyl iodide :)
Nice intro man! Love it!
I came back here because I was shocked to learn...
HE ACTUALLY HAD AN INTRO
Nintendo switch cartridges
Yea I licked one. Quite nasty
And your fingers after handling switch cartridges. Yes, this is true.
@@memememegaming I learned that the hard way. Never change cartidges with freshly washed damp hands, never lunch after said cartridge switching.
I licked one once. It wasn't so bad
Wtf
This was the first video I watched on this channel and I hooked me now 3 years later i still love this channel
masochistic cooking sounds like it'd be the greatest cooking show ever
Nile you are awesome. I wish some glassware or chemical compound company sponsors you or something. Your channel and style is so good. I love it. Keep going man.
+Batuhan Bulguroğlu Thanks :). I have actually had someone offer in the past to donate glassware to me, but right now I dont really need it. The biggest thing i need now is a good vacuum pump. Maybe ill shop a little for it today.
Hey! I actually understand the mechanism and types of reactions! That's cool! O Chem is actually useful
I like the new intro! Short and sweet.
Glad you finally finished editing this video. The gooeyness is very interesting. Maybe some impurities that eventually get dissolved back into the acetone and finally washed away?
I hope you get a new pump soon so you can do some vacuum distillations.
I'd like to see your HNO3 video next and the methylamine video once you get a better pump (I think I've said that before, getting déjà vu). With all the higher quality chemistry videos here on youtube recently no one is really doing any vacuum distillations or reactions under vacuum. There's so much more opened up to you using lower temps and lower pressures. BTW nitric acid synthesis is a bit cleaner done under a vacuum a la UC235.
+kjpmi Yeah, i really need to get some funds together. My vacuum pump now is useless for distillations. It cant run longer than 5 minutes without smoking :s
Nice sound branding! (I don't know what its called😅)
I watch your videos everyday (don't judge me😅🤣), but hadnt seen the little intro audio branding dealie yet, I like it!👍👍
Gettin' fancy with an intro! Nice =)
Hi Nigel, would you make a bitter blocker substance? That would complement this video nicely.
I love the fact he’s using a paper clip as a stir bar lmao I’m going back and rewatching a lot of your videos
9:36 i think you mislabeled Denatonium Chloride as Denatonium Hydroxide in the second diagram ... still cool video tho!
i no longer take organic chem class anymore but watching your videos brings me some memories back.... i really liked that subject. it was one of the classes i studied really hard. so thanks for making such good videos!
Loving the new 4k video and new microphone.
Your description makes me want to eat this stuff
“This chemical ruined my life for a few days nonstop”
“Anyway we’re making it with these few ingredients”
I'm not surprised lidocaine is involved. The lidocaine suspension I got after GI surgery was horrific. The only thing that's maybe worse is the barium chalk drink before a CT
Very nice, i really enjoy yours videos
Could you do some organometallic reactions?
YES PLEASE!!!!!!!!!!!
+The Chemistry Kid n-Butyllithium flamethrower, baby!
...
Oh, and useful stuff like Grubbs catalysts too....
+Sword of Apollo I would LOVE to see dimethyl Mercury, but it is incredibly toxic, which is like saying the sun is a bit warm.
DO DIETHYL ZINC IT IS PYROPHORIC
madz bush do you mean the positive nitrogen ion on the right with the negative chlorine ion? That's funny 😉
Hi Nile, I started watching your videos a few months ago and I have always enjoyed everyone of them. you know what? I'd like you to show us how to produce hydrogen peroxide.
+Luca Maistrello making it is way too hard. I do plan to concentrate it at some point though
man you are awesome, keep going!
cool intro, and great video!
Do a video on making ceasium metal from lithium and ceasium chloride
"From his fingers, to the cards, to his friend's cards, to his friend's fingers, to his friend's mouth". This should be used as an experiment to demonstrate how COVID can spread.
Accidentally distilled off Denatured Isopropyl, and my resulting product was chock full of Denatonium... Not sure which one (Hydroxide, Chloride, Sulphide, Benzoate, etc), but ever since then I have always pre-tested my Technical-grade Alcohol to ensure that it isn't generating this Godawful substance. If you need this chem in the future, I think distilling it from Dollar Store bottles of Rubbing Alcohol would be a cheaper and easier way to get it.
Thanks for the awesome chemistry and synthesis videos... 🙏 They help me understand complex reactions, and infer other potential reactions, most of which are entirely Undesired, Unintentional, Uncontrolled, and Unhealthy for Human exposure. There are a lot of idiots in industries... Mis-labeled chems, improperly substituted chems, dirty chems, and lapses of logic seem to be the major factors that will RUIN all the hard work and time spent.
Nice intro! But maybe you can add something related to chemistry. One idea could be putting a molecule inside the red circle and depending on the video you could change it.
I want to see you proceed to make the most sweet chemical in the world (afaik)
Lugduname
Is it sweeter than Alitame?
@@mubasshir yes, by more than hundreds of times.
Dang, I never knew he had an old intro!
Yay Nile has a new intro!
The gift that keeps on giving...
Could you use this stuff to dissuade/find out an office food thief, by lacing your food with it?
Yes.
Would you jump through so many hoops just for that? There are cheaper things you can buy at the pharmacy.
Cyanide works better. Nobody will ever steal your food again. Unless you're caught.
Staple their fingers,
@@ethangoldsmith9332 it hurts when that happens
You claim in the title that denatonium benzoate is the most bitter compound known, but wikipedia claims that denatonium saccharide is five times more bitter, being detectable at 0.01 ppm as opposed to the benzoate's 0.05 ppm threshold.
Both of these are still absurdly bitter, of course.
Sounds like you just found ourselves a new challenge for playing cards 🤣
Ironically, saccharides are usually sweet.
@@GRBtutorials reminds me, saccharin actually has a nasty bitter aftertaste
basically people lump the denatoniums together. the practical difference is trivial
Time for some super-scientific self experimentation.
Cool vid. Try serial dilutions to see at which concentration you still cand taste the denatonium.
A Q&A would be pretty awesome.
hey nile, can you make a video about liquid/solid ozone? it would be very interesting :P
Oh yeah
Heck yeah
Toluene. That reminds me of trinitrotoluene. [TNT]
Will you ever make this? I just find it interesting. Because it releases its energy so amazingly fast. But if you do produce this, please make a tiny batch, and exercise safety.
You dont wanna have "a hand" in this reaction lol.
Love the intro!
I kind of want Nigel to also make the sweetest chemical, sourest chemical, the saltiest chemical, and the umamiest chemical, then mix them all together with this and tell us what it's like. ULTIMATE FLAVOR.
Now teach us how to get this thing out of my hand sanitizer
Try distillation
Oh god this aged like milk
@@hiiammatthew8735 LMAAAO
Not using hand sanitizer in the first place works just fine. If you accidentally took a shit straight into your palm, try soap or something, should be more than enough.
If you work in medical field... Just use pure alcohol?
how about some methanol synthesis?
Nice intro!
Nice intro Nile!
10:07 maybe u should try sending it to its room
That is a tasty intro.
Nicolas Giandrea So tasty, it could balance the flavour of the subject of the video.
The new intro looks nice :)
lovin the intro ;D.
9:36 says denatonium hydroxide both places
Immagine the police come to his house while he’s doing this...
Awesome video!
9:35 I assume you meant to write chloride in the bottom left equation? No big deal, just noticed it, and you do say it correctly, and have it correct on the right side of the bottom equation.
Love and appreciate your videos! It's not possible to do all of these myself, so it's nice to see them done. =)
Do you know why the cost of potassium (1,095/kg) is so much more than sodium (220/kg). Is it because it is more hard to make potassium via electrolysis than sodium or is it because of regulations on the sale and production of potassium. If anybody knows please help. Just wondering, thinking about making a small electrolysis cell to make some lithium and sodium based off of some patents I have been reading and was wondering if I could do it for potassium because it was not specifically talked about in the patents or anywhere else.
Prices are based off of gallium source so they are probably quite high
But, why would you make it into the benzoate salt rather than keep it as the chloride? Does that affect its bitterness?
If so, how? benzoate ions aren't bitter.
+piranha031091 I am honestly not sure
Finally! I have been waiting for this video forever! Time to have the family over for dinner.
+Linus Tuttle
I'm going to let all of my family's silverware soak in a solution of this for days. Lmao!
+Linus Tuttle
Actually, nevermind I have a good idea on how to infect everybody at my school. xD
I'm impressed with the intro it's kinda how it's made ish with the beat
3:20 Calm down there.
"When I was playing cards one day..."
It's cool, man. We know you're not playing poker, blackjack or baccarat. You can tell us. Was it MTG, Pokemon, or Yu Gi Oh?
A realy great intro :D
Hahaha love the custom stir bar!
I found nail polish remover that said 100% acetone and I was going to use it as a solvent but the I looked at the ingredients and it said acetone and denatonium benzoate. 100% acetone my ass.
It might’ve said that because the amount of acetone in the nail polish remover is so close to 100% that they just rounded up
When he says playing cards, he definitely means magic the gathering
Liking the new intro ☺️
This is very interesting and how you explain everything in detail is commendable. I have some remarks though:
1. You maybe should have used a separatory funnel to separate the toluene and water layer. Maybe this contributed to your poor yield?
2. I guess what happened is little bit of acetone got dissolved in your denatonium benzoate which is why it formed a jelly, like in your calcium acetate/alcohol jelly experiment. Does this sound probable?
3. You didn't wash your final product with water to get rid of acetone, is it safe then? :)
Best regards to you and thanks for patiently considering my points.
Not really enjoying new intro, but great video :D
+Mario Borras Why dont you like it?
+Nile Red In my opinion the intro is fine, it adds value to the content (which is great :) )
+Nile Red I agree with Mario, it feels slow and out of place in my opinion. Amazing video as always though :D
+Nile Red Well it seems like a good edited intro, but I think it's a little too long and the music doesn't quite fit.
Martynas Malikėnas yeah true. I felt like that could be the case. Thanks for the input. I put it in because it was made for me and I wanted to show my thanks. I probably won't include an intro in the future
What if I wash my face with acetone?
Mud Kip If you do that you can frame your face and put it on he wall
it'll be the last time you'll ever wash your face
Your face will probably just get a little bit irritated and dry, but the denatonium benzoate but still be there and you'd still be bitter as s***. Lol 😂
I like the new intro, makes it seem more professional. Just make sure it’s not more than 9 seconds or it gets obnoxious.
Sick new intro!