Phenol from Salicylic Acid

[@NileRed]

Cool thermocouple thermometer. I really need to make one of those

[@ZivTheWyrd]

NileRed yes you do!

[@ClownWhisper]

NileRed if you haven't got a thermocouple yet I think I have some watlow controllers and perhaps the thermocouple and cable somewhere around here I know I got to that I use personally I think I have some extras I'll start looking

[@perfid-deject2027]

ay dood

[@NicolasBana]

I'm always amazed how chemistry can be so simple and so tricky at the same time, after all you only needed to heat the Salicylic acid... But it made a 17 minutes vid of an excellent quality !

[@PauloConstantino167]

Hello Doug. I am very interested in your home lab. I wish to build one at home for my own purposes. I am an organic chemist. Would it be possible for you to make us a video where you go over some of the finer points about your lab?

[@bdot02]

Yay! I've missed your videos!

[@TheHuntermj]

+bdot02 You're glad you missed his videos?

[@huhdidwhat]

no, he's happy to see the videos again... hence, Yay! duh 🙄

[@JRScience]

Another awesome video Doug! I have a question about your heating mantle -- Do you think your mantle could get hot enough to perform a distillation of sulfuric acid? I ask after watching NurdRages video on his home made mantle and sulfuric acid distillation. If it could get hot enough I'd love to know the details on your mantle, cost, wattage etc. Cheers!

[@sekovittol3124]

If water is slowing the phenol from solidifying, couldn't you put some water in with the salicylic acid to keep things moving and not solidifying en route in the column? Or if not that introduce some steam in the column?

[@tman31090]

Finally, I've been waiting a month for this.

[@ClownWhisper]

If you wrap the condenser with the inlet so it warms up it'll almost boil the water in it yours is a little bit wider than mine so it might not boil it but mine just barely bubbles it so I just fill it once and leave it and it keeps the whole system perfectly clear

[@gillasosaurus]

did Doug die? :( 5 months since the last video

[@kentuckyprepper1792]

The cloudy mixture is phenol in water. The phenol is clouding because it wants to be a solid at room temperature.

[@jonhoyles714]

glad your back doug great vid as always nicely done :)

[@shinchaniyer]

It's not fennel. It's phenol.

[@elliotwilliams7523]

Amen

[@DancingRain]

And soooo many KZbinrs keep calling phenol "fennel"...

[@BxnkrollBeatKillerBEATKMB]

@@dylanmcvicker8330 Repeated use fucks me off so bad

[@BxnkrollBeatKillerBEATKMB]

​@@DancingRain own expensive equipment but repeat 'fennel'

[@Cobaltophobia]

Phenyl is a different group. His pronunciation bothered me

[@stefanraul2070]

Is it true that these heating mantles can reach 450 degrees C ?

[@DrakkarCalethiel]

They can get so hot that5 glassware starts to melt. I think NileRed had such an accident.

[@oscill8ocelot]

Hey glad to see you posting again =)

[@tobinator680]

Can you Show us how you make your vacuum?

[@astroglide420]

how can i get the same thermometer setup? And what kind of gloves are you using? Would using a respirator even make any sense during these distillations, like the nitric acid video?

[@Glattuh]

Thanks for hearing me Doug¡ Awesome video

[@StevenSSmith]

New Camera? The footage looked so much clearer than usual.

[@atrumblood]

I hear phenol pronounced both like feenol and like fennel the spice. which way is correct?

[@kevinbyrne4538]

+Curtis Dorris (AtrumBlood) -- phenol = feenol whereas phenyl = fennel

[@1234lavaking]

Both. It's a regional thing but the more accepted pronunciation is "feen-awl" because the "awl" sound is used in other alcohols like methanol, ethanol, etc.

[@boobiesandshit]

+1234lavaking It is more definitely not a regional thing. Stop justifying it haha you're pronouncing it WRONG.

[@homealchemy]

When can we expect the next video Doug? I really miss it!

[@ExemplaryLigas]

how do you clean de rbf? nice yield

[@aetius31]

Nice vid! But are you sure it is a good idea to put the phenol in a bottle container (especially with such a small opening)? getting it out will be a pain again

[@BackYardScience2000]

With such a low melting point (104°f) all he would have to do is hold it under some hot water and liquify it to get it out of the bottle.

[@alexeyleontev7220]

Why not using the simple deflegmator and reflux condenser

[@jamie91995]

Since you work with toluene, xylene, and methyl ethyl ketone. Can u let me know how dangerous they are? Do you need to wear a respirator, is it toxic, what do u do if it gets on ur skin, what do u do if you inhale a bit of it, Etc.

[@photonthelatios7828]

The chemistry Nerd Those solvents aren't very toxic. If you spill some on you, worst thing that'll happen is dry skin. Inhaling any organic solvent in excessive amounts is obviously not healthy, and flammability is their main hazard.

[@tobinator680]

Where do you buy your glassware? Is there a recommended shop?

[@mikeseidman6899]

I saw one of your video were you have lot of sulfur, i was wondering if one day you will test the Willgerodt variant where styrene/sulfur/morpholine is used

[@erictorkelson5778]

TLDR:you have sulfur, make a meth precursor... not likely.

[@kostyk-kostyk291]

And the synthesis from phenol to catechol?

[@AwesomePower1234]

Could you do a video where you separate aspartame into phenylalanine and methanol?

[@diegocrescente8785]

Could the yield be increased by protecting the OH group?

[@marcofico1]

+Diego Crescente probably but it would require another 2 steps (protection and deprotection). Phenol is such a cheap compound that if you really need it you should just buy it. This is a nice demonstration for small quantities. Ciao

[@jozefnovak7750]

Super! Beatiful! Thank you very much!

[@theamateurscientist]

doug i have an interesting question i just bought a distillation apparatus and now i dont know a solvent that can remove avry thing and when i distill alcholol it will be safe to drink CAN SOMEBODY REPLY TO ME AND TELL ME SOME SOLVENT

[@bdot02]

Elbow Grease? Or I'd watch a few of the Periodic Videos and lurk in that comment section.

[@TheBookDoctor]

P.S. you forgot the patreon link.

[@rraabbiitt]

Is it possible to reflux salicylic acid to decarboxylate it? I think it'd be easier.

[@dimaminiailo3723]

It isn't due to the salol formation, but fractional distillation seems to be a good choise

[@stephenjacks8196]

Copper powder or Cuprous Oxide will catalyze the decarboxylation.

[@dimadj01]

The yellow color of the first distillate is probably because of the phenol's oxidation to 1,4-benzoquinone during the heating.

[@LazarusWorms]

I suggest extracting eugenol from cloves and doing some stuff with that! Your lab will smell of Christmas!

[@TheKutia]

this is cool man, its been a while sence ur last upload keep it up!

[@gogear131]

omg your alive hazzah

[@Dinnye01]

The high FPS is amazing :)

[@puo2123]

The milky forerun ist the water phenol azeotrope. Its milky because the phenol formed tiny droplets.

[@lajoswinkler]

When you heat the acid, as you saw, it not only decomposes, but partially sublimates as well, so you have basically got a distillate which is a mixture (possibly some kind of azeotrope, I don't know right now) of phenol and the acid. What you need to do is to set up a refluxing apparatus with a long air condenser or passive Liebig one (like you did, with water boiling inside) and let it churn for few hours. It will decompose to completion. Then you distill it slowly, using an air condenser. It won't clog, and its surface is easily accessible for the hot air gun if the mass starts to solidify too much. Anyway, it's really good that you do these videos. Cheers.

[@lajoswinkler]

***** It might not increase yields, but it will destroy the remaining acid which is very volatile and usually escapes into the recepting flask.

[@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

[@annelieseocallaghan801]

Congratulations on not being poisoned!

[@ahmetselcuk1400]

Catechol video please

[@quantumlab9130]

Phenomenal

[@lagrangiankid378]

Phenol-menal.

[@theginginator1488]

I believe you can do this in the presence of alkali to help the decarboxylation. This will produce the alkali carbonate and the phenol, similar to the process to make benzene from benzoic acid

[@UC235]

+TheGinginator14 That doesn't work. Although I've not posted any videos in years, this is my procedure writeup from sciencemadness. Copper catalyst doesn't work (unless you add quinoline/pyridine) and alkali would make a black tarry mess since phenol is an acid and can be deprotonated.

[@origamigek]

But wouldn't that be much harder on the glassware near the end?

[@SimiliaSC]

Man.. you are a legend Bro! :D

[@TheBIBSS]

I know this is a weird question but,is your lab located in a house or at like w collage or something

[@TheBIBSS]

A collage**

[@JooJingleTHISISLEGIT]

A collage? You mean college?

[@TheBIBSS]

+Joo Jingle you got what I meant right

[@JooJingleTHISISLEGIT]

Jose Villanueva Well, it's hard to correct someone if you don't know what they mean.

[@tyedosminecraft]

hes back!

[@libalj]

I was getting ready to look for news reports of a home lab accident in MI.

[@user255]

+Doug's Lab New videos soon? Can you do anything interesting with creatine? It's OTC and cheap.

[@diegocrescente8785]

Sooo right!

[@CloeStump274]

How old are you Doug?

[@jamesnewmeyer7205]

When I heat the Salicylic Acid the phenol that comes over only comes over at around 100 deg. C. And never at anywhere near 170 C.

[@danielaustin7643]

Could you not dry the phenol chemically, such as mag sulphate?

[@LiborTinka]

yes you can dissolve phenol in ether, dry with sodium sulfate, filter, remove solvent

[@Berghiker]

What type of thermocouple do you have and how do you close it off with the glass stopper?

[@rassimsimou1594]

Good

[@goodsir2551]

Why do you only make one video a month?

[@WizardZph]

This year he said he will probably make one per week!

[@beneric73]

thanks, this video is great !

[@kentuckyprepper1792]

I used to be a phenolic resin chemist and did phenol distillation daily. We always distilled without water circulating through the condensor. Phenol solidifies, blocks the apparatus, and blows. Pheol can be deadly. They trained us that the size of a quarter skin exposure could be deadly.

[@196Stefan2]

Can you tell me, if it is possible to separate phenol from salicylic acid properly by a simple distillation? The issue here is that salicylic acid obviously does sublimate at the boiling-temperature of phenol, that the distillate is probably contaminated by salicylic acid. Do you have an idea to dehydrate hydrous phenol solutions (carbolic acid)? kind regards

[@kentuckyprepper1792]

+196Stefan2 +196Stefan2 If you are set on distillation try a second run of decarboxylation. Heat gun the sublimed material if it starts to appear. Or try heated filtration. Phenol melts at 105F and salicylic acid at 318F. If salicylic acid stays solid and out of solution may be able to filter it. Words of warning. Phenol is deadly. Don't try this at home. Only do this with proper safety equipment in a proper laboratory facility. Look up the MSDS on phenol and heed it's instructions. Or at sublimation try decanting the phenol.

[@silveradoman298]

It sucks that Doug has gone MIA.

[@kkirschkk]

I know it sucks, there is very few people on youtube that do this

[@irvingkurlinski]

Good luck getting the phenol out of that small necked bottle!

[@ClownWhisper]

Pronounced feeeenal fennel is an herb

[@stevebuczek]

(FEE- KNAWL) not (FEN- NEL). directions unclear ketamine turned into chocolate pudding.

[@Smellynyx]

I cried

[@agent475816]

You pronounce phenol wrong. It is (fee-nooL)

[@SoDerpy]

+agent475816 Only you care

[@agent475816]

SoDerpy I don't care, I'm just saying.

[@annelieseocallaghan801]

I think it's pronounced "fee-nol"

[@agent475816]

It is.

[@WizardZph]

Yeah ik... He kept on saying phenyl which was confusing me for a second because I thought he meant benzene. It actually makes a big difference.

[@stephenjacks8196]

Phenol and Fennel are homophones. "You say tomatoe, I say tomato."

[@Tonyneg]

Phenyl does not equal Phen-ol

[@gogear131]

i thought you OD on toxic THC fumes

[@HeartOfGermany]

+gogear131 That only makes you high as hell. :D

[@mikeoxlong1396]

Make a video where you synthesise lysergic acid diethylamide ;)

[@FueledByCookiezGamin]

+Mike Oxlong we don't want him to be arrested now would we. synthesising lysergic acid is extremely hard. you might be better off extracting lysergamides from hawaiian baby woodrose seeds. im not sure though

[@boobiesandshit]

Why are you pronouncing Phenol (Fee-NOL) like Fennel? hahaha Most "OL"'s pronounced the same way.

[@TheRedKnight101]

+Something Something Different dialect then your own.

[@boobiesandshit]

No, when something is ACTUALLY called/pronounced a certain way - you're meant to read it the same way - it's not a dialect thing, it's you saying it wrong.

[@OKB1133]

You definitely know your subject but need to speak slower.

[@rraabbiitt]

Is it possible to (normal) reflux salicylic acid to decarboxylate it? I think it'd be easier.

[@rraabbiitt]

Although I foresee the phenol and salicylic acid reacting this way....