Turning Aspirin into Tylenol 

I'm an old-school chemist (PhD 1987). I love what you do, and it reminds me why I fell in love with chemistry as a teenager! Keep experimenting and teaching!

"I was able to convert 200 extra strength aspirins into one really weak tylenol" SUCCESS

I followed along with your video precisely and I ended up with 42 pounds of crystal methamphetamine. Please advise.

"Turning one really weak tylenol back into 200 extra strength Aspirin tablets"

“Polymerized crap” is the IUPAC name

"Ah crap I got aspirin, not tylenol" "Don't worry mom, I can work with this"

NileRed: The process is very straight forward Me 26 minutes later: Wait what?

21:36 I thought "he's good... look, there's a Tylenol capsule in the product!" It was his stir bar.

Converting a fresh big mac into a bk wopper

I have to admit, I use your videos to fall asleep at night. Your voice is so soothing, calm, clear, and never talk too fast. You could narrate a bus schedule, and I'd buy the audiobook. I listen intently and usually before you're done, I am out like a light. But you are not boring! Thats how I discovered your channel. I actually watch the video again the next day. Thanks for your excellent channel!

next time someone asks me for a tylenol imma whip out my bottles of aspirin and my chemistry set and make it from scratch just to spite them

Note: The "filler junk" is actually a carefully designed matrix that produces the correct dissolution profile and bio-availability of the tablet, whilst also ensuring proper binding, distribution of active in the matrix, good compression and ejection from the tablet press, etc., all without having a biologically active impact.

I like to imagine NileRed as an alchemist in a fantasy world. "Today, I will be turning this stone into a bar of iron." or "I had an idea to try to turn a healing potion into a poison."

I watched the original videos a while back. This was far less scattershot and easier to digest.

The “polymerized crap” label in the diagram at 7:44 made me laugh way more than it ought to have 🤣

I have no clue what come out of his mouth 99% of the time, but his videos are really addicting to watch

23:12 "So my original prediction of 30% wasn't that far off, I just kind of misplaced the decimal by two spots" LOL

Thanks, but I think my headache has gone now…

My sister's going to school for chemistry. I always whip out somthing I've learned from these vidoes. Her face is priceless

Can you do converting Advil to morphine next? Asking for a friend

That sweet, sweet vacuum filter action!

Only being off by an order of magnitude isn't bad, if you are an astronomer.

just thought you should know, i sent this to my mom who’s a pharmacist, and classically has a video attention span of 2-5 minutes max. that being said she watched the WHOLE thing and loved it!! really great stuff lovin it

I love how passionate he is about chemistry.

Just wanted to say that I shared this with my mother, who used to be a research chemist 40+ years ago; we both really enjoyed it. =)

Think I'll just go buy some tylenol.

I’m allergic to Tylenol Let me get my tools

This is so interesting. I wish I had paid more attention in chemistry

I love these longer videos. They're so satisfying and fun to watch.

Amazing! Since my wife is a chem professor I am really wanting to brush up and retake some chem classes since I have forgotten so much in the 20 years since graduating from college er... maybe longer, since I was way more interested in playing baseball than retaining this info. You my friend are exceptional.

3:48 you should be aware that this is a yield of 94g of a mixture of ASA and salicylic acid. The recrystallization step almost certainly hydrolyzed a substantial amount of your product, not just a few percent. You can confirm this by using the iron (iii) chloride test for phenols. You will obtain a colored adduct with your recrystallized product, confirming the presence of a phenolic hydroxyl group. I know this because I synthesized ASA from salicylic acid and acetic anhydride, and after quenching the reaction mixture and decanting the precipitate, the crude product was recrystallized from boiling water. The melting point was extremely broad, strongly depressed, and was dependent upon the rate of heating. The NMR spectrum was a mess but did demonstrate the aromatic protons around 7.2-7.24ppm, and FTIR showed a broad and intense absorption around 3300/cm, and a sharp, very intense peak around 1710/cm. This is all immaterial, however, since your next step is to hydrolyze any remaining ASA.

Do be careful with the phenol. It's quite hazardous: Around a tablespoon on the skin can be fatal, and the burns it causes are painless so you may not notice that you spilled it on yourself until it's too late. Another concern is that trying to wash it from your skin with water tends to just spread it and increase the area of skin that is damaged- you must instead wash it off with glycerol or a solution of polyethylene glycol. I certainly wouldn't handle that stuff without a lab coat on!

Thank God for CVS, if I had a headache and needed to go through all of this for Tylenol I’d have a migraine or a brain tumor before I was finished.

This is really cool. As a reference to reality, you created a 210mg rough equivalent of Tylenol? That's wild.

When I want to convert my aspirin to tylenol, I just bring my receipt back to CVS and they swap it out.

The art of turning 200 aspirins into 1/2 tylenol :) For real now, I have a love for chemistry and your videos are pure candy. The right equipment properly used, apt explanations pleasantly delivered, good quality camera, camera work and cuts makes it a joy to watch. My average patience for youtube vids is about 7 minutes, yours watch like professional documentaries. Your videos are excellent fodder for chemistry students. What I find particularly elegant and alchemistic is that your subseqjuent videos keep transforming molecules made in earlier installments, highlighting the dance of functional groups that is applied chemistry. Every molecule can be an end point, starting point and intermediate. A pleasure.

You are awesome Nile! I'm so happy that you are succeeding with RU-vid!!

I watched the orignal series like 2 or 3 times , but one video covering the basic reactions is pretty nice as well. I think you should do this always: a while after ther series combine it into an video

"Even though I do stuff like this all the time, it still blows my mind that it's possible to systematically build and degrade things on the molecular level." And this is, I think,, probably the very most basic essence of most people's interest in chemistry. It's mine, anyway. Chemistry like this is essentially a kind of microscopic engineering combined with the performance of what feels like microscopic magic tricks, except you perform them for yourself as opposed to the _macroscopic_ card tricks you'd perform for others. Actually doing organic chemistry like this almost feels like you're playing god in a small way, like these things shouldn't be possible and it's incredible that the possibility even exists, let alone that YOU get to just play around with it and have fun with it AND get paid for it, if you're extra lucky.

Twas the night before Christmas, when all through the *house* Not a creature was stirring, not even a *mouse* Yet one thing was stirring, twas NileRed's low yield Tylenol *crumbs* Ha-ha-ha

Great video. Here's a couple of points that could be useful for improving the method: (1) I've seen some sources suggest that deprotonation of salicylic acid aids decarboxylation due to the competition for the proton. This should also stop the esterification as the carboxylate is not electrophilic. (2) Before nitration, protect the phenol with either acetic anhydride or (acetic acid + HCl + boil). Do the nitration using c. sulfuric acid as the solvent, and 1.1 equivalents of NaNO3, at -5 degrees Celsius (ice/brine bath), then hydrolyse. It adds two steps; however, this will lead to a selective mononitration to p-nitrophenyl acetate. Also means you avoid forming nasty di(-) and trinitrated products, which will be explosive. Work it up by pouring it onto ice and water and filter in vacuo. The crystals you get out will be almost exclusively p-nitrophenyl acetate. (3) The decomposition of p-aminophenol is due to oxidation/polymerisation in light, but it actually amounts to very little (if you check by NMR etc), so long as you keep it out of solvent. Recryst. from water is the usual way of purification, but I found that toluene works well too (if you can get your hands on it). (4) Recryst for p-aminophenol should be easier than for paracetamol. Source: my own research lab experience

goddamn this gave me a headache, can i have that paracetamol

Neat! Whenever I want to turn my aspirin into tylenol, I just pour some mor into the tylenol bottle. But you're method is much more impressive. Keep up the good work.

So there's a kind of coffee maker that used to be used a lot more, called a vacuum pot, which is essentially a self-contained vacuum filtering setup for extracting coffee. It's crazy to me how much a vacuum filtering device like the one used here looks like it when the flask is attached. Basically it consists of a flask-like carafe and a filtering bowl that has a long glass tube that goes down into the flask, with a rubber gasket between the two and one of various kinds of filters in the bottom of the bowl. Water bubbles up into the top where it is mixed with coffee, and eventually air bubbles out through the tube too and is not replaced. With the proper timing, you can develop a really good low pressure environment inside the carafe that sucks the water right out of the coffee grounds as the carafe cools. It's especially cool watching water boil below 100 c in the carafe, if you get the pressure low enough.

Ive learned more about chemistry from your channel than I did from seven years at school with a shitty teacher. Thanks man.

next video: "turning Pseudoephedrine into crystal meth"

I personally hated chemistry in school but this is just so interesting that i regret paying so little attention to it in school. Thank you !!!

Your channel has sparked a great intrest in Chemistry with my children and I. Seeing how things connect when you find pathways to connect them. Absolutely brilliant

Would you make a series of Flavor and Odor making videos? Love your channel!

Your channel has definitely reinvigorated my interest in chemistry. Thanks!

Man, I love your videos. I have always loved chemistry and physics, and ironically, i dropped out of chemistry just due to my attention to 3D CAD/CAM and physics and now photography, and just not able to dedicate the correct amount of time to chemistry that it deserves. Thanks for all you do. I really enjoy seeing your work.

I'm taking Orgo 2 at university right now and we are basically learning different reactions and mechanism. I'm now re-watching all your organic synthesis to see how much I can recognize. This honestly is amazing to me being able to come back and thinking how and why you came up with your reaction pathway or possible side products.

17:30 That flask looks so pretty with all those greens!

And this is why I do inorganic chemistry... :P QUANTITATIVE YIELDS!

your videos are really calming for me somehow. And i learn a bunch about my favorite kind of science along the wayy so perfect combination. Thank you for doing these videos! :) they help a lt especially now

Hey, I'm fairly new to your channel but I fell in love with your content. You make some pretty awesome videos and I genuinely enjoy watching them. I also appreciate how, for someone like me who doesn't really understand the science behind the experiments that you do, you explain every step of what's going on so everyone can follow along with what you're doing and that's great because otherwise I would not be interested and wouldn't really know what was going on in your videos. Thank you for explaining the science of your experiments for people like me. I am interested in what you are doing but I don't really know the chemistry behind them so for you to explain it for us, keeps me interested and I always learn something new from watching you. I love your channel and your content and you genuinely help me to not only appreciate science but help me to like it and keep my attention and I actually really enjoy what I'm watching, so thank you.

Reminded me of my chem labs. Loved watching and guessing your next steps without stressing for any upcoming exams lol

im studying organic chemistry its fun to watch things happen instead of cramming reaction :P

Fair play to you with so many steps involved!

That's one is the one of most lovely project, NILE RED.

As much as i hated chem in school, i love watching your videos.

as a pharmacy student, i loved this video. it's so cool seeing the structure change.

Watching a video like this makes me want one long ass video of you just cleaning all your glass after a project.

Really cool. A video of full chemical synthesis will all the steps and difficulties described. Thank you, as a person who's very interested in that.

I think you should do the Caffeine as a single video, no matter how long it is, I think it’s nice to not have to deal with the wait time for slow internet(which I have half of the time)

I feel like regardless of how much you love Chemistry, the clean up sometimes makes it feel like it isnt worth it

That was very fun, thank you kindly!

This was seriously fascinating, I’m amazed by how things are converted.

24:41 Why I watch your videos, even though, a lot of the times, I don't understand it.

I'm curious about your cleaning process. How do you clean everything?

This takes me back to organic chem lab. Love your content, keep it up!

no disrespect; i love your videos. this one in particular though i’ve been putting on to fall asleep every night for the last week. it knocks me out like 3 minutes in every time. i like to think that eventually i will learn something.

Turns out creating Tylenol is quite a headache.

7:43 "polymerized crap" lmao

Just had a mental breakdown check. Just wanna let you know, your voice is very comforting to me. i dunno why, but it is.

Wow, that NMR it's amazing

Outside of north america Tylenol is more commonly recognized than acetaminophen. Having grown up in Texas, I default to the generic name and over the last year I have needed to purchase it in Mannheim Germany, Cork Ireland, and Santiago Chile. In all 3 cases the word "acetaminophen" was not recognized but the word "Tylenol" was recognized when I asked where to find it (although in Santiago that was likely a result of Tylenol having a more standardized pronunciation globally).

I never knew aspirin is not the same as paracetamol. In The Netherlands we often use the words interchangeably meaning the same thing, which is probably paracetamol.

Cool Video. It set me back in the Time when i do synthesis.

7:43 “polymerized crap”

This was great. The nitration step is terrible. Still gives me nightmares from my old classes.

I've made aspirin before, or ASA to be precise. At some lab. ended up being pretty high purity. Couldn't take it back home though, but was about 10 grams yield or so.

This was interesting to watch. I graduate in May with a B.S. in Chemical Engineering, and my senior project is designing an acetaminophen plant. I didn’t end up getting phenol as a raw material but I know people who did.

No idea what I was watching, but super excited to see that you did it.

Bro made a aspirin potion 2:25

Request: If you are going to do a long and complicated synthesis chain like this for caffeine, but don't want to do a lot of your normal high production value videos, could you make a B channel where you upload lower production value deeper dive videos for each step as you go? You are probably correct that a summary like this is of more interest to most of your viewers, but the 90+ minutes of your original series seemed to have a lot more reflection on what went wrong where and how you might want to do it different or why you did it the way you did, which is very useful and/or interesting information for some of us.

Kids today are so lucky to have your videos and teachers especially in high school should take advantage of this to inspire young minds.

this is how I'll get ahead on my Chem class. no joke, I love these videos.

19:27 he turned grape soda into ginger ale

Next Video: “Crystal Meth from Pseudoephedrine”

The purple tint of the p-aminophenol solution violently brought back memories of me developing with Rodinal and the color change of the spent solution

I love the subtle Nile-ism in these videos

Sometimes I wander how fast I would die from drinking some of the things you show in your videos

For my next trick I'm going to boil water and turn it into ice.

As someone who takes migraines medications that has APAP in them, this was a fascinating watch! Thank you 💖

You just made a bunch of chemistry concepts click for me. Fantastic video.

RU-vid made me watch an asperin ad before this video lol

Fascinating! Although, if I get a headache, I'll just take the Aspirin. 😁

Wow, I hope you didn't get a headache from this project!!! I love listening to your voice!!! Purple Chrissy

By the time you finally came with the tylenol, the headache is far gone