Aspirin to Acetaminophen - Part 3 of 6: Phenol from Salicylic Acid

[@silkyz68]

I think it would be interesting to revisit this series and make a run trying for the best yeild possible

[@noodlycreature1322]

I am in high school and you are the only guy who can make me inquisitive about chemistry. thanks Nile

[@NileRed]

:)

[@noodlycreature1322]

+NileRed what do you do exactly?

[@noodlycreature1322]

my mom said that we cannot get these things easily. :(

[@ReallyWemja]

+NileRed The red/pink color is probably be unrelated to the dye. When extracting salicylic acid from plants it often has a red color too.

[@nemeanlyan7918]

You're the only KZbinr I have notifications turned on for. ;)

[@NileRed]

Thanks! :)

[@voosum]

Ryan Cooper same

[@enewtevnewton]

me too. well, I have nurd rage as well.

[@edysmetsers5436]

@@NileRed there can be only one!!😂👍

[@NileRed]

Follow me on my Twitter: twitter.com/NileRed2 and my personal Instagram: instagram.com/nilered2/

[@joeya5438]

How is this comment one day old when the video is only nine minutes old?

[@MasterGXD]

Joey A vid was released publicly a few mins ago

[@joeya5438]

MasterG ooohh thx

[@chrischristen8904]

Hey buddy, hows it going?

[@batsman46]

single digit yield is expected so don't worry about it

[@NileRed]

I have more faith

[@RedBloopCreature]

I just want you to know that I watch both your channel and Cody'sLab. The thing is that I nearly failed chemistry when I was in highschool. But now I find it fascinating although I now know I'm terrible at most science. Learning for fun and learning when you have no choice are two different things I guess.

[@NileRed]

Glad to have you!

[@serwoolsley]

i have no idea what's going on but i'm mesmerized, this is so fascinating

[@Dawnbandit1]

Could you try to extract salicin from Willow bark and convert it to Salicylic acid and then to ASA?

[@NileRed]

I will do that at some point :)

[@Dawnbandit1]

NileRed Awesome! A lot of people don't realize how a lot of medicine comes originally from plants. Just started supporting you on Patreon.

[@natefunk1]

That is where the pink color is coming from that he mentioned. Salicin has a pink hue when it is extracted from the willow bark (something in the bark is pink). Not exactly sure what causes it to maintain the hue, but salicylic acid will usually start to turn pink as you heat it because of this.

[@Adoringprodigyfan]

I'm pretty sure the people at Bayer don't get their salicylic acid from trees.

[@natefunk1]

check this wikipedia article en.wikipedia.org/wiki/Salicylic_acid Even if not from trees most sources for it are plant based. You'll notice in the article that i can be synthesized from other chemical sources though. Maybe that is where Bayer gets it from.

[@ethan12313]

Love these videos. Good job. You are one of the KZbinrs I have adblock paused for, keep up the good work.

[@NileRed]

Thanks, I appreciate it! :)

[@zubmit700]

I really like how your channel is forming. Keep up the good work.

[@NileRed]

Thanks!

[@waterunderthebridge7950]

Let's start a petiton to make "leftover tarry crap" an actual chemical term xD

[@vikramkrishnan6414]

Leftovertarrycrapium

[@bsheaves]

Among synthetic organic chemists, tarry crap is a technical term

[@mortlet5180]

YES! TAKE THAT PINK BAYER DYE!!! I really don't know why I'm so invested in this but it made me pretty happy to see that the phenol is clean at the end. :) Great job by the way!

[@NileRed]

Thanks!

[@1st_ProCactus]

That's some hard core shit dude. And thanks for using DCM a lot. I now know it as 3 names and use it for acrylic. Unfortunately for a while the best way I can contribute is by watching and thumbing up. Sometimes a comment. Cheers

[@NileRed]

that is all you need to do to support!

[@HTobias]

Could you make like a chemistry basics video. Not sure how popular it would be but i'm sure there would be some people who'd watch it.

[@psychicai7346]

can melatonin be turned into serotonin? if so, is it possible to some day make it on one of your videos? I guess what i'm hoping for is more synthasis of hormons and neuro-transmitters to be in your future videos. Thanks for the interesting content!!

[@davideaezakmi9530]

Why don't you add Iron (III) chloride to a small sample of phenol in solution to check if you still have some salicylic acid?

[@Andrew-my1cp]

What would the addition of iron (III) chloride do?

[@lunadieschnecke6695]

@@Andrew-my1cp iron 3 can form complexes with phenolic compounds, and salicylic acid is one example. Salicylic acid forms a very characteristic purple colored complex. Phenol itself can react with iron 3 too.

[@AAAAA1_AAAAAA1]

2024 and this is still the best playlist (my opinion).

[@jaromschafer913]

hey, you forgot to mention that you also previously did the same decarboxylation of phenol in a prievious video, although instead of making Tylenol, you made phenolphthalien.

[@NileRed]

Oh yeah that is true. Old stuff that I dont even remember :p

[@erwanlm8814]

Wow ! Great job ! The kind of chemistry I would have enjoyed as a student. You should apply for "best teacher of the world" ^^. One idea for another multisteps videos could be : amino acid starting from alcohol. Ethanol --(I2)--> Ethyl Iodide --(Mg)--> C2H5MgI --(CO2)--> C2H5COOMgI --(H2O)--> C2H5COOH--(Br2 then H2O)--> 2-bromopropionic acid --(NH3)--> Alanine.

[@Imaboss8ball]

I'm pretty certain almost all chem 1 labs make aspirin. At least I did.

[@collinbardini]

To prevent the formation of the ester product, couldn't you add some water to push the equilibrium towards the phenol?

[@NileRed]

In theory, but you need A LOT water to do that. Enough that it would ruin the distillation

[@collinbardini]

Ok good to know. I guess paper chemistry doesn't always align with reality.

[@willim.6985]

Can you make a Mercaptan-Synthesis ??? The Odor of natural gas in Germany.

[@andrzej_autko]

"Was provided by user unintentional chaos on science madness forums" is my new favourite catchphrase.

[@thatcanadianguy2852]

i have watch your video's ever since 2100 subs, i have not watched a video in a while and wow 101,386 subs congrats

[@hal013]

Yikes! 😬 we’re getting really close to your first prediction... 14 percent seems to be better but I have a lil more hope! I predict ~20%

[@krisztiantoth3116]

Hi NileRed. Regarding the red discoloration of your salicylic acid, i have an idea. Phenol like compounds give colorful complexes with iron ions. This is the so called ferric chloride test. The color of the complex depends on the substituents on the aromatic ring. User baguvix aezakmi also mentioned the reaction with iron (III) ions before me. You could test the color of the complexes for both salicyllic acid and the phenol.

[@NileRed]

I was really thinking that it could be iron complexes. Maybe ill do a little testing

[@todoroki6157]

That was so many words… how did I understand that?-

[@user255]

Excellent work!

[@jamie91995]

Can you do a video on hydrofluoric acid? It's uses, dangers, safety protocols, etc. thanks

[@NileRed]

Nope, I do not. I have actually never worked with it before

[@KainYusanagi]

'i do not' what? I do not know enough to do so, I do not work with it so cannot say, what? o.O

[@aMondayMorning]

NileRed You might have misread the comment there, lol.

[@sivalley]

Kain Yusanagi Why not both? :p

[@acrakatau4365]

I would guess the first milky fraction could be just phenol with water, because they form a low boiling azeotrope and don't mix very good in the cold. If it is/was a large quantity it could be worth drying for a higher yield.

[@NileRed]

It is a 90/10 mixture water to phenol i think. That much phenol should dissolve in water

[@Robocop-qe7le]

Salicilic acid sublimates, maybe the milk in the flask was water and salicilic acid?

[@NileRed]

Hmm, that is very possible!

[@Alex-nd5my]

Can you do a video on how to dispose of hazardous waste

[@Jerrytheman9]

Could you have done the decarboxylation first, then hydrolyzed the resulting phenyl acetate ester to avoid the formation of phenyl salicylate?

[@markrigsby2107]

Great work

[@NileRed]

thanks!

[@iantabor3276]

At 4:43 where does the hydrogen that is bonded to the non-double bonded oxygen go? It doesn't carry over as hydrogen gas, or does it just show up bonded to one of the carbons in the ring? Thanks!

[@jrahm111]

Can you do a video about solving an alkali metal in liquid ammonia?

[@MikeTorres-s8w]

Wh how to make methamphetamine what are the names for the Ender

[@SimiliaSC]

What is the name of your heating fabbric device?

[@danielaustin7643]

could the pink colour of the liquid be a small amount of benzoquinone from some Phenol that is starting to oxidise (the l liquid looked a lot more pink than the solid before melting)

[@Pseudomonasa]

I really like your videos +NileRed could you make a video about using fehling's solution to determine the present of glucose in urine?

[@NileRed]

That is a really good idea. I think I will do this!

[@gardenguy357]

can literally almost anything be cleaned with acetone?

[@ThePaintballgun]

not everything, but lots!

[@aMondayMorning]

Don't Even Bother Can I clean myself with acetone?

[@aMondayMorning]

ramirez223 Normal symptoms of a true deep cleansing.

[@dylanlyon7215]

aMondayMorning idk if anything can cleanse your sins

[@luism.1732]

Almost always useful! Just don´t use it on flasks still containing chlorine, bromine or iodine or there will be regret :D

[@tabletopjam4894]

Make thiolacitone(sorry for misspells) then describe the smell

[@thenerdyfarmerguy6144]

You should film the video on Uracil soon. I've always wanted pure poison ivy/oak in a bottle lol.

[@NileRed]

Uracil is actually an RNA base and not poison ivy. That is urushiol. Although it would be AMAZING to make that...I feel like I could very well die doing it

[@DrDuckMD]

Your videos are addictive to watch and i never liked chemistry.

[@frankiescra]

Man can you do a Q&A video?

[@musafer2648]

make a video on turning acids into anhydrides like nicotinic anhydride or acetic anhydride

[@NileRed]

As far as i know, it is pretty useless to try and make acetic anhydride from acetic acid. I am not sure about nicotinic anhydride

[@musafer2648]

NileRed I thought it could at 800C anyways keep up the good work, your videos are great

[@oxm18]

Can you make tramadol???

[@zliveris12345]

Okay so I plan on performing TLC and traditional column chromatography and I need help. gravity isn't a strong enough force to elute obviously and I don't have a license or funds to get a 5ft nitrogen/O2 tank, and I was thinking an air compressor but those are also expensive. does anyone have any experience with at home chromotography workup? please let me know

[@bsheaves]

Should have added a protecting group to the hydroxyl

[@minecraftermad]

4:35 chemistry pun?

[@johnhancock7090]

Nile please tell me where you purchased your bottles with the blue cap or if anyone else knows??

[@NileRed]

from ebay

[@johnhancock7090]

NileRed thanks man my cylindrical media storage is taking up way too much space

[@khushichauhan6431]

Phenol has actually is light pink in colour

[@aMondayMorning]

Is there any way to avoid creating that useless polymer, or is that just inevitable and some of the Phenol /will/ react with the Salicylic Acid?

[@Felixkeeg]

You could hydrolyze the ester afterwards, but I can't think of any way to stop this reaction.

[@NileRed]

Someone above mentioned using a protection group on the OH group (like an acetyl) to prevent it's ability to make esters. It is some extra work to do that and might not be worth it

[@billsmathers7787]

So in other words, decarboxylate acetylsalicylic acid directly?

[@Felixkeeg]

NileRed Yeah, I thought about this for a second too, but it seems like a waste of chemicals and time.

[@LeahtheReds]

"Polymerized crap" so scientific. We'll see that term in the journals any day now.

[@jakkuwolfinsomnia8058]

Have you considered using a fume hood? Unless it's already in one, I feel letting gas vaporise into the air is concerning to me because of your health and environmental damage. I love your videos but I don't want you to put yourself at risk because of it.

[@NileRed]

I have thought about it, but I havent implemented one yet. If I think something is actually dangerous, Ill do it outside and wear a proper mask. I appreciate the concern though :)

[@jakkuwolfinsomnia8058]

NileRed good thank you for considering 😊

[@jhyland87]

I tried this synthesis - It killed my stir bar, lol. I guess what they say about cheap Chinese stir bars is true - They can't handle ~200 °C.

[@chasefuller8496]

Couldn't that milky stuff have been solidified phenol?

[@Hobypyrocom]

can you show us the nitration of Phenol while you are at it?

[@pinksapphire2898]

haha, i believe Nile isn't a fan of explosives

[@NileRed]

Ive made picric acid before!

[@pinksapphire2898]

Really?! I swear ive watched every video of yours and never saw one on it lol. I just know I've heard you say multiple times about your distaste in stuff like that.

[@alexschmidig7413]

Where do you get you chemicals and you heating mantle thanks

[@NileRed]

Heating mantle from ebay and chemicals from ebay mostly

[@Grove332]

What would happen if I drank the liquid salicyclic acid?

[@shadowsonaga]

You won't have headache anymore but serious stomachache (salicylic acid is pretty toxic for the stomach, contrary to acétylsalicylic acid) and your blood would be more fluid so you could get some serious hemoragies. Over all, it depends on the dose. (Sorry for my english i'm french)

[@cambam9749]

Make butyric acid from GABA via diazotization and hypophosphorus acid.

[@billsmathers7787]

Doesn't work; upon diazotisation the carbonyl group attacks the carbon attached to the N2+. This expels nitrogen and forms a five membered ring, gamma butyrolactone. In fact, this is one of the most common ways of illicitly preparing GBL. In general, diazotisation reactions on non-aromatic substrates tend to be a bit dodgy, due to the extreme instability of diazonium compounds and the easy loss of nitrogen gas (forming a carbocation) or a proton (forming a diazo compound). These decompose to an ill defined mixture of products.

[@cambam9749]

Do you have a reference for that?

[@billsmathers7787]

Not directly, but an analogous reaction occurs when producing alpha halo acids from amino acids with the corresponding hydrohalic acid and sodium nitrite: the lactone forms with inversion of stereochemistry, and a halide ion attacks the strained lactone formed, inducing another inversion of stereochemistry. Thus alpha halo acids can be made with the same stereochemistry as the starting amino acid. See orgsyn for a reference.

[@argiebargyplays]

I think it definitely would have increased the yield if an alcohol protecting group was used in the decarboxylation step using something like an acetyl and benzoyl group and then deprotected it after the reaction. It would prevent a lot of side product, and although it introduces an additional step it'd probably have raised the yield to maybe 75% after acid-catalysed hydrolysis. Furthermore, the bp of benzoic acid is 249 celsius and is thus easily separated from the phenol product, which can also easily be dried with a dessicant. Obviously it's a little late now but perhaps could be useful for a future rendition or similar reaction scheme. The only other thing is that I'd recommend stoppering round-bottomed flasks containing intermediate products, such as the salicylic acid or phenol, with a greased stopper between reactions to prevent loss of yield by transfer. Still excellent videos though!

[@NileRed]

Yeah, that is true, protecting it would have helped a lot. I feel like the ASA is abundant enough though that I am okay with a lower yield. Not sure if i'd want to use my precious acetic anhydride to protect it

[@magicwaffles2559]

Very good video again :)

[@NileRed]

thanks!

[@goldnmotivation496]

where do you film your videos?

[@keyurmarolia]

Make tri -nitro toulene pls Little bit pls

[@lewisho8114]

WHY IS THE PHENOL STILL PINK

[@6jonline]

...And if you want to see what happens next, I'll provide a link in the description.

[@joshua22267]

Make barbituate acid

[@donciterenyi4494]

"I'm just hoping that it doesn't dip into the single digits" ... Not done and is already at 1.5%...

[@unpreppedprepper2710]

Oh dear! I tried this experiment a few years ago, but it went wrong due to my stupidity and I poisoned myself! :-( I didn't recognize, that the small outlet on the right was blocked, so the whole system was under pressure. I then removed the upper part from the flask too early and a flush of phenol steam went directly into my face and I inhalated it. I felt a burning pain in my bronchia and I could hardly breath. Short after that, I became dizzy and very weak. I wanted to call the emergency number, but I just felt down to the floor and could not move. There wasn't any power in my muscles anymore... I thought: "Shit!! That was it dude!!" 24 hours later, I woke up and my first thought was: "Holy f*ck!!!! I'm still alive!" ;-D What a disgrace!! :-D

[@Sauti_science]

Dude??!

[@Okja1ONE]

how does the stir bar work?

[@MuzikBike]

magnets

[@retrograde3971]

Hey Nile, love your videos. I have a quick question. My friend made some Lithium Hydroxide and wanted to make it into Lithium Peroxide. Turns out our chem teacher doesn't possess any 35% Hydrogen Peroxide and won't even give him any of her 30%. Is there any other way that you know of where he can complete the Lithium Peroxide synthesis? Thanks.

[@nemeanlyan7918]

MalevolentGoblin You could technically concentrate some H2O2 by vacuum distillation. I can't say I'd recommend it, and it's kind of hard to tell exactly what the concentration of H2O2 is, but you could try it.

[@NileRed]

Unfortunately, I dont know of any other ways. Is it that hard for her to get peroxide?

[@retrograde3971]

NileRed She is an AP Chem teacher and is only able to buy from Flinn Scientific which according to her only sells up to 30%. She also made some comment on the price of the hydrogen peroxide and how it is expensive, is there truth behind that? How did you get your peroxide?

[@KainYusanagi]

Not just according to her- you can check the site for yourself. www.flinnsci.com/store/Scripts/ck_prodList.asp Search for hydrogen peroxide and you'll find that they only stock up to 30%, with a 100 mL bottle going for about $11. For a bit more (plus shipping) your friend could get 250 mL of 35% food grade, though that may have secondary reagents that he might have to address, compared to lab grade. www.amazon.com/Percent-Hydrogen-Peroxide-Dropper-Bottles/dp/B00ID1X258/ref=pd_lpo_121_tr_t_3?_encoding=UTF8&psc=1&refRID=QN9G4ERHAS9X49CS46A6 Most places that sell lab grade H2O2 are much more expensive; SEOHCorp has a price point about the same as for food grade H2O2, but charges more than the price of the 500 mL bottle (27.50) as a hazmat shipping fee. He'd also have to get a business (so the school, for example) to accept the package. www.seohcorp.com/seoh-hydrogen-peroxide-35-tech-500ml/ All in all, I'd just say deal with the problems of using food grade H2O2 over lab grade H2O2, since Flinn states "Orders may only be placed by certified science teachers and shipped to a certified school address" and that or lab certifications seem to be a prerequisite for lab grade H2O2 in the USA.

[@uchihasurival2972]

What happened to your tear gas video?

[@uchihasurival2972]

I just noticed it got take down. Do you have other video links? I hate censorship.

[@MuzikBike]

I think the hydroiodic acid one was unlisted as well.

[@NileRed]

I took a few down because KZbin was on a rampage and videos were getting flagged left right and center

[@MuzikBike]

that makes sense. Why those specific ones though?

[@nilnileer]

​@@NileRedI read this in your voice! :p

[@mrchary5025]

bro in salicylic acid decompostion u missed HYDROGEN

[@thisisnotmyfinalform7856]

yes i waited so long thank you if you respond i will be happy

[@NileRed]

Anything to make you happy!

[@mexicanmuslim]

hey can you combine Gold and Neon and make Goldeon? i really would like to see the properties of this substance. I would also like to know how to make a alkaline oil called capsacin could you make that aswell?

[@theRkzs]

"this really isnt a big dildo" ahahaha 7:43

[@acceptthetruthitwillsetyou2598]

iS THIS NURDRAGE WITHOUT THE VOICE CHANGER... i THINK I'M ONTO SOMETHING

[@undeadflex]

y u upload so late.

[@NileRed]

haha, I meant to do it in the afternoon but i forgot

[@youngmesa4258]

I thought this was a pyrolysis reaction

[@cybeermancom1]

how would you decarboxylate the thc acid to thc?

[@wikcoool88]

teach me how to make chlorine trifluoride for genocidal reasons :)

[@NileRed]

Ill get right on it

[@danger6204]

5:25 *intense chemistry lingo* CRAPPY POLYMER

[@gobs10]

I have heating mantles for you

[@wormbait1706]

Hi

[@NileRed]

hello

[@TheGraphiteCovenant]

make a vid on how to make sulfuric acid pleasee!

[@psychicai7346]

unknown "milky white stuff" heheheh....

[@NileRed]

I knw there would be comments on that, ha

[@chedisLoL]

just saying. I'll most likely donate like $30 in a few weeks :)

[@NileRed]

You dont need to, but I do appreciate it! :)

[@casualmtg6675]

acetone is gods gift 2 chemist dissolves dam near everything

[@gamingmarcus]

If you really wanna dissolve almost everything go with chronic acid. That stuff is awesome.

[@ShadowsLetsPlays37]

Chronic acid? huh that'd be a very interesting acid.

[@gamingmarcus]

TehSoulja Sorry I meant chromic. Damn autocorrect on smartphones doesn't know anything about chemistry :D

[@ShadowsLetsPlays37]

P@r@m3d!© It was a pleasure

[@MuzikBike]

Chronic acid is not acute character.

[@ravenous9577]

Yay ily

[@NileRed]

ily too

[@the866-sushi]

Ha ha "Tarry Crap" ha ha

[@grantrichter8884]

extract caffeine from gfuel

[@NileRed]

Not sure ill do it with gfuel, but I will probably try it with monster or something

[@grantrichter8884]

NileRed haha i think you have a different kind of caffeine addiction

[@grantrichter8884]

NileRed addicted to extracting it

[@_rubberstopperman_]

Bad yeld? Ha-ha )) Synthesys of -(-)Batrachotoxin is 24 steps with 0,25% yeld

[@NileRed]

0.25% is a great yield!

[@nostalgistl0058]

reply me,reply me,reply me...

[@NileRed]

Whatsup

[@nostalgistl0058]

nothing,I am just a little bored.:p

[@MikeTorres-s8w]

Wh how to make methamphetamine what are the names for the Ender

[@greendragon3351]

hi

[@NileRed]

oh hello