Cleaning Dirty Phenol

[@BackYardScience2000]

About distilling without vacuum, I have done this and it works decently well. Though the yields aren't as good as when a vacuum is used. You do end up with a bit of discoloration and an impure product. But, it can be easily separated with another distillation under an inert atmosphere if vacuum is unavailable. There are cans of argon that can be bought on eBay that are for keeping wine from oxidizing and it works well for this. It is cheap as well. I think I gave $12 for a whole can of it. It is enough to fill 2 or 3 large wine bottles full of argon.

[@zzdjchris]

I very much doubt I'm alone in saying I love watching distillation vids. Especially Vacuum distillation vids that you made. I see distillation as one of the 1st uses in chemistry that hasn't really changed, and won't. It's so powerful (in chemistry), yet so simple. Thanks.

[@NickGleason3]

Back in grad school, I'd periodically need to do synthesize Fmoc-Alanine for peptide synthesis and used phenol each time. Every time I opened the bottle of phenol the smell would immediately remind me of my childhood. I was never able to precisely pinpoint what the odor specifically reminded me of.

[@spiderdude2099]

It’s pretty close to mothballs. Did you have them in a closet you remember as a kid maybe?

[@olliemc88]

Thank you for all your hard work on these videos. I can tell it's your passion, your videos are excellent quality. You have reinvigorated my interest in chemistry!

[@jb280557]

That formation of crystallization is simply breathtaking truly beautiful

[@astralchemistry8732]

I would suggest a steam destillation for the purification. But your setup is also a good option, as proven by the video. I hope you'll feel ambitous! The literature (Purification of laboratory chemicals, elsevier) gives the procedure of destilling phenol with a fractional column over calcium sulfate and then recrystallizing it several times from absolute toluene or xylenes. This should yield water free phenol.

[@holidaycat]

Hey man. Could you do a video about basics for a home lab? Or suggestions and ideas maybe for creating a ventilated area that is suitable for OC and AC ? I would really want to try some experiments at home but I am kind of overwhelmed in terms of where to start. In addition, i am not a student of chemistry, i m a biology student, we only have two chemistry modules (one in the lab) and i would like to keep doing stuff at home too since its just way to interesting to pass :D

[@ifitmattersidontcare]

Lol. I was surprised by Nile Red's use of the word ghetto considering the formal manner in which he presents. Just made me laugh, not that he can't use any word he likes.

[@snasty99]

ctrl+f in the comments just to see if anyone else felt similarly. was funny.

[@djdrack4681]

Canadian Ghettos are different than here in the US. I hear that there are far more woodchucks as well as the large beaver.

[@Wheresmy240]

I chuckled when he said it too because it seemed out of character

[@bigchungus1592]

Phenol-menal video! (i disgust myself.)

[@madfoxmax4600]

Jay Ricco you disgust me to

[@KnakuanaRka]

*ba dum tss*

[@GRBtutorials]

@@madfoxmax4600 Not me.

[@hikaru-live]

I kind of wish your questions would become the beginning of some serious research. Can't wait to find out that one day you end up being the co-author of some academic paper originating from one of your video.

[@alexparriss-hind3315]

I’m gasping in awe

[@oliver.7400]

i’m wishing i didn’t click

[@alexparriss-hind3315]

OLIVER. Jeps is clapped haha

[@oliver.7400]

Alex Parriss-Hind can’t argue with that

[@alexparriss-hind3315]

OLIVER. Did you know crocodiles have constantly erect penises? That means crocas is constantly in lovveee

[@oliver.7400]

Alex Parriss-Hind that’s what i heard too

[@danielaustin7643]

the first one is the best. any carbocation is bad, they are very prone to side reactions occurring such as rearrangements, always been told to avoid them

[@Timothy656]

After seeing the first mechanism it definitely seems like it's the more feasible option.

[@divenutslincoln]

I agree!

[@AntonVagabond]

Agree, that primary carbocation I seriously doubt that stays like that

[@marco5826]

I thing if not add H3PO4 this reaction run and stopping on alcohol.

[@soonsoon6422]

how to recation fenol and h2 o2 with castic

[@abcrtzyn]

5:55, “I need to make some new stuff” Does that mean you write or play music?

If you ever have any doubts about purification drying, look up Purification of Laboratory Chemicals by WLF Armarego and CLL Chai. They write: the phenol is separated, dried with CaSO4 and fractionally distilled under reduced pressure. It is then fractionally crystallised several times from its melt [Andon et al. J Chem Soc 5246 1960].

[@rob5435354]

Love your channel keep up the good work. I'm really glad you will be putting out more content!

[@kevinbyrne4538]

It should be possible to distinguish which mechanism is correct by examining the reaction's products ; specifically, if the second reaction mechanism is correct, then there should be a variety of chlorinated propyl compounds among the reaction's side products.

[@zock4419]

Yes you asre right, the propionaldehyde isn't the strongest nucleophile but under acidic catalysis it's more active.

[@jasonbooth5182]

I use to work around this stuff daily. It was 99.9% molten phenol used for the nylon plant. Everytime I unloaded this stuff I was nervous we bleed the the vapors back into a carbon bed. We were fully suited to unload it.

[@pedrohenriquedossantos5175]

Indeed the carbocation of the second proposed mechanism is quite unstable, but while the chloro atom withdraws electrons by inductive effect it does estabilize the carbocation by ressonance effect, since it has free electron pairs that can interact with the empty p orbital of the ion. This stabilization is already described in the reaction of alkynes to a hydrogen halide -- the carbocation formed in the second addition occurs in the alpha halogen, not in beta, as you would expect thinking in halogens only as electron withdrawing group. In that way you would not get a hydride shift to form a secondary carbocation...

[@bsheaves]

I've done a lot of research with carbonyls and just because it is an aldehyde vs. a ketone I've found that it really doesn't matter when you have a good nucleophile like an aromatic with donating group or an enol or even a chloride ion. I would prefer a mechanism that is like the second but undergoes a Sn2 reaction as opposed to the Sn1 just because of steric hindering involved with phenyl ring attacking a carbonyl.

[@cambam9749]

Make butyric acid from GABA via diazotization and hypophosphorus acid.

[@AnnaVannieuwenhuyse]

I'd rather have that GABA in my BODY. :')

[@atari7001]

Nile, would you be interested in attempting a synthesis of some sort of rubber compound? It is almost non-existent on youtube with the exception of a simple silicone rubber synthesis made from water glass and ethanol. Is there a simple rubber compound the home chemist could make that would actually be useful for practical application? BTW, thanks for the wonderful videos. I enjoy them very much. Cheers!

[@ReapingMiner]

First one is the best, i tried myself comming up with a mechanism but i too ended up with a primary carbocation. Primary carbocations are a nono! Also due to the Markovnikov's rule i kept running into 2-substituted chlorine and or anisole groups for the chloropropene.

[@TCFr97]

0:31 looks like coca cola slush puppy

[@mihneazoican2479]

The first mechanism is the right one. The protonated aldehyde is really electrophilic and is easily attacked by the anisole. The second mechanism has 2 major problems.. one has been stated in the video, the other one is that the intermediate with OH and Cl is basically a tetrahedral intermediate of a carbonyl nucleophilic substitution and it would break down into an aldehyde.

[@tommybaker351]

You're wrong Mihnea Zoican! The strong electron withdrawing group of Cl could be enough to stabilise the tetrahedral intermediate that is formed during the reaction - I have seen this occur in similar reaction mechanisms. However, the first point brought up by NileRed about a 1,2 hydride shift occurring due to the instability of the primary carbocation I completely agree with and this would result in the wrong product being formed.

[@floyddango]

Aldehyde is actually a rather strong electrophile. Some aldehydes are barely stable to store without the electrophilic position being attacked by a nucleophile (often water). High polarisation of the C=O carbon plus you only have a hydrogen instead of another carbon bond to it, which makes for a very small steric hindrance. The protonation of the C=O oxygen further increases the carbons electrophilicity. The mechanism is called hydroxy alkylation. Especially with the electron rich phenol ring it's a fast reaction.

[@hedgeclipper418]

I wasn't here when you originally asked the question, but when I saw the question in this video, the thing that immediately came to mind was the mechanism that the Wise Sabbath posted. I'd love to solve a mechanism to get a beaker, but I'd also love to just buy a beaker off you. As for mechanistic speculation, questions like "does a rearrangement occur if a given intermediate is produced?" are the perfect sorts of things to use computational chemistry to solve because it doesn't actually take very much work to get an answer. In this case, I think it's unnecessary because the C+ would certainly rearrange, but generally speaking, it's a good way to answer questions like this.

[@thecarrasius]

looking forward to Ammonium metavanadate, Don't hear about vanadium that often. :)

[@MortRotu]

Faffing Around With Chemicals that's because altho V chemistry is full of pretty colours it's very very fussy and difficult to reliably get right.

[@maggiep9007]

Mexico's only element never gets to be the star of the show :(

[@desertrainfrog1691]

@@maggiep9007 It's used in a lot of knife steels nowadays, so it's got something.

[@PraecorLoth970]

I think the first answer is more probable. The carbocation on the second answer is very worrying for me.

[@idvarhurd7804]

Ghetto-paper-towel condenser

[@vincentandrew4717]

watching your videos are somehow helping me study for the MCAT

[@matty9460]

Do you have a link to that song you used when it was crystallising? You said you need to make more music so did you make it yourself? From that little bit it sounded really good

[@KnakuanaRka]

matty9460 The text says he also used it in his cinnamic acid video; he might have a source there.

[@C134B]

I think that the second isn't probable because of the unstability of the carbocation due to its position on the chain and the electron substractor oxygen. the first option is the right answer.

[@chromecrescent]

The primary cation could be stabilized by Cl π donation. Not sure how that compares with the tendency for hydride shift though.

[@s07561277]

I had a different mechanism in mind. Though it is similar to your mechanism. My idea was the same as yours for the first two steps. Then I drew the hydroxy group picking off the proton from the para position to restore aromaticity. The water leaves, forming a secondary carbocation, with the chloride hitting either face. I suppose it could also happen in one step, but the position is secondary, and therefore unlikely. I like your mechanism, but I don't think the double bonded carbon in step 5 would be sufficiently electrophilic to be attacked by the chloride. Also, is the product mixture racemic? Because attacking at that double bond would yield a racemic mixture of products, since the chloride can attack on either face of the planar carbon-carbon double bond.

[@davidwithall1965]

mechanism one is correct. you are correctbthat the primary chlorocation wont form, and if it did you would get a 1,2 hydride shift

[@kalimsheikh2494]

Nice video, i am pretty sure the first mechanism is right. Similiar reaction has been done by gilch to synthesize PPV.

[@jaredgarden2455]

You should try the classic reimer tiemann reaction on phenol to make salicylaldehyde not sure what you could do with the salicylaldehyde except perhaps convert it back to salicylic acid or perhaps prepare some catechol or something but the reimer tiemann reaction would at least be cool to perform and watch.

[@lajoswinkler]

Every time I smell phenol, I think of cadavers. I don't believe I'll ever get rid of that feeling.

[@origamigek]

Hmmn, I agree with the first mechanism, but in the removal of the pronated alcohol, would a chloride ion not just kick it off in a Sn2 kinda fashion? Instead of the double bond formation after which it is attacked by a chloride ion, which doesn't seem likely to me. A nucleophile attacking a double bond.

[@vevenaneathna]

8:40 I hate to be critical but I suspect the addition of chloride to the active positive species (just after water comes off) would likely resonate to a more stable structure and follow direct addition of the Cl- to a positive benzylic carbon. Im pretty sure you might have considered this and opted to simplify the reaction scheme on paper within the same step so it might be a mute point to you; however, I believe the properties of aromatic resonance and activation would strongly stabilize this specific transition state and is responsible for the highly specific addition at the benzylic carbon location.

[@FreeFireFull]

Would it be viable to store chemicals like this in an atmosphere of nitrogen? Or would it be too hard to stop oxygen from leaking in?

[@Zestric]

It would help with the oxidation issue but I don't think there is a practical way of doing it.

[@BackYardScience2000]

Argon can also be used and may be just a bit better because it is heavier than air. But as said before, it isn't very practical. Though it will work for short term storage.

[@hcn6708]

Phenol-ly! A Video!

[@MrRishik123]

I like the first mechanism by the Whysalmon

[@IlusysSystems]

I am realy happy that you start playing with polymers. Are you still planning to make polystyrene vid? Because as it should be pretty easy my attempt to radical polymerisation of styrene or MMA ended up in some rather higher mol weight polymer but not remotely solid. Maybe I am supposed to dissolve this polymer in monomer and try to polymerise that mixture. I was hoping, that I can go from low viscosity liquid straight to solid.

[@ChibiYumSweet]

Not to be gross, but the phenol in the beginning looks like earwax.

[@ananteshesha5788]

What kind of fucking earwax have you been around man?

[@piotrgrzelak2613]

​@@ananteshesha5788 I was surprised to learn this, but apparently some people have solid earwax that comes out as flakes. It's also racially divided, this type happens among east asians.

[@bobthecannibal1]

rewards/fairness: Set a time limit? "You have a T (time) to suggest the best way to do Z. (method) the best entry will get Y. (prize) Submit answers at M (contact method) no later than midnight on D (date)" Doesn't eliminate the lack of discussion aspect, though. Maybe reward the best idea and method. But that could be a pretty large pain in the fundament.

[@KainYusanagi]

Kevin McLoed produces a lot of free music you can use. Consider looking into that for music samples?

[@allurared9029]

5:30 when u see the messy shelves in back reflecting off the flask

[@chadgdry3938]

if you have the funds, try both and discuss them. also, recognizing the people that give you the correct answer rewards their contribution.. just scroll their names after identifying the m as having the best answer.. but keeping it academic is fun if you can bet on it.

[@T42nk]

Hey, an intersting topic you might tackle is how to properly discard chemicals for the amateur chemist, especially since you do this from home.

[@JB-wj4cv]

wow, getting through this reaction mechanism is hefty when you speak it out, and its an easy molecule. does anybody ever SPOKE out the mechanism of the total synthesis of lsd from trylptophan? hammilton morris did it with ketamine synthesis.

[@nackomega9505]

You might be right , because primary carboncation is unstabled , but if phosphoric acid has working it should be with OH group complex , chloride attack carbon then kicked out them. :D

[@GamersBar]

Seeing how bakelite is made sounds interesting could you talk about why it was used so much when you make it too. Also , how do you clean your stuff , im sure you have had issues with shit sticking to glass, i ask because i had to clean a old filthy toilet in a house recently , I almost had to break out oven cleaner it was so baked on stuff.

[@Mrbpotter1]

Nile, please feel ambitious!

[@NileRed]

I do!

[@hlakanipetros6670]

why don't you use a acyl chloride ....

[@Quintinohthree]

Hlakani Petros What exactly do you think that will achieve?

[@hlakanipetros6670]

Esters

[@Quintinohthree]

Hlakani Petros Yes, and? Now you've destroyed your phenol and added acyl chloride as an extra impurity. How does that help clean you phenol.

[@stanalbatross8615]

I would add something that forms a lower boiling azeotrop with water, to get anhydrous Phenol

[@vaas7479]

Thanks for the always great content!

[@fabricwheels7028]

I love these cleaning videos!

[@ashW110]

Hi Nile, I believe you used the rotary vacuum pump for this process as water aspirator won't be powerful enough. Did you have to change the oil in you pump after this process? As far as I know phenol is slightly soluble in mineral oil and I believe quite a bit of phenol vapors passed through to the pump.

[@BKScience812]

I would propose a third mechanism. I like the first mechanism all the way until the alcohol gets dehydrated. I think the phosphoric acid could phosphorylate the secondary alcohol forming an electron withdrawing phosphate group on the benzyl carbon. Once phosphorylated, I believe the phosphate would make a much nicer leaving group, not to mention the phosphate is more electrophilic than hydronium. Also, the electron-rich benzene ring would make this an attractive phosphorylating site. The reason I favor phosphorylation as a mechanism is because it is shown as a catalyst. HCl is good enough of a proton source, so I see no reason for a second acid, much less phosphoric acid specifically.

[@gagerowden1316]

If you add hydroxyquinoline at 0.1% (w:v), it will help prevent your phenol from oxidizing.

[@a3xccy379]

Awesome Video Nile ! Im excited for the next video as handeling ammonia and pouring it makes everyone cry( Sarcasm) I would like to know is there any other way to do it with minimum vapours pouring out! Also As in biology we have molecular docking. So in chemistry we have any such software where we can predict mechanism of a reaction or its still done the old school way of tracking a molecule by labelling it !

[@Timothy656]

You can indeed use isotopic labelling to label a specific site in a molecule and then see where it ends up once the reaction is finished - although the reagents can be very expensive. You could also create a "Hammett Plot" to determine the linear free energy relationship of the reaction. This would allow you to see if positive/negative charge is being built-up close to, far away, or very little at all to the aromatic ring in the transition state of the rate limiting step. For instance, a positive Rho value from the plot would indicate negative charge is being built-up, whereas a negative Rho value would indicate positive charge is being built up. This could then help you decide which mechanism is correct by looking at which one seems to fit the data better overall. There are also many other methods that you can use to help elucidate reaction mechanisms :)

[@a3xccy379]

+Timothy Morrison Thanks for such a deep reply !

[@davidli6931]

8:14 Isn't the first step should be like the para carbon attacking the carbon at the carbonyl group at the aldehyde group?

[@Sinistersider]

It would be really cool if you showed a nitrolysis reation with the hexamine that you made a while back

[@kevinbyrne4538]

At atmospheric pressure, the phenol-water azeotrope contains 91 percent water by weight. The azeotrope can be "broken" (that is, the phenol and water can be separated) by adding a ketone (e.g., 2-butanone) and either benzene or toluene. (See: www.google.com/patents/US4160111 ) Adding petroleum naphtha also works. (See: www.google.com/patents/US2209150 )

[@tylerswanson6358]

The only thing about the first mechanism is that shouldn't it go through a Wheland intermediate for EAS instead of the methoxy donating into the ring?

[@Artillect0]

Would you be able to use a reducing agent to convert the benzoquinone to phenol and break up the polymer?

[@timmulm]

Actually yes, on my phenol bottle they suggest to distill over Zinc dust in vacuum, when discoloured

[@kevinbyrne4538]

12:05 -- Ammonium metavanadate. Hmmm ... Can the preparation of Mandelin reagent be far away ?

[@JourneyedAvenger]

can you make a video on extracting propanol and/or butanol from sharpie markers? I think that would make a fun and cool video

[@petevenuti7355]

now how do you turn this into aniline , and then conductive polymer?

[@24grantj24]

have you every made anything that damaged your stir bars, are they some type of crazy plastic or ceramic or what.

[@Quintinohthree]

Grant Johnson Teflon usually.

[@mingh9543]

Would you mind my asking what type of the Vacuum you are using? My vacuum always get jammed by the cool solid phenol :(

[@thisisnotmyfinalform7856]

i really want to see uracil synthesis 😀😀😀😊😊

[@casualmtg6675]

nothin like a glass of phenol 2 wake u up lmao (dont)

[@jb280557]

casual mtg bro how can i make the phenol that does wake you up in the morning ? If you can explain in detail i would prefer but would love the recipe !

[@majintroll4454]

how did you manage to obtain the optimal concentration for the ghetto product?

[@Metalhammer1993]

well i a bit late but on the last question from the previous video: my bet is i think covered by the wise salmon. i kind of thought about how phenol and Acetaldehyde form Bakelite. under acidic conditions the oxygen of the propionaldehyde gets protonated further activating the carbonyle and that is enough to trigger electrophilic aromatic substitution. the result will be the carbonylgroup becoming an alcohol directly attached to the aromatic ring. and we have HCl in there and HCl+Alcohol in a more or less water free environment is a surefire way to make alkyl chlorides. just don´t see the point of the phosphoric acid. So the first part seems pretty easy to me. the second part which you thank god didn´t ask for, however showed me how bad my dementia is i entirely forgot about elimination reactions. i was torturing myself with how the pyridine might insert itself in the carbon chlorine bond thanks to it´s lone pair of electrons on the Nitrogen. how pyridine normally reacts with alkylhalides btw, but i totally forgot that a base can always abstract a proton from a carbon adjacent to a carbon with a halogen or any other decent leaving group on it and just kick the halogen or the leaving group in general out that way. classic beta elimination. completely forgot about these^^

[@satchelfrost6531]

Concerning the last reaction, why don't you do a mechanistic study i.e. Kinetics experiment. It looks like the outcome should be SN1 which means first order with respect to the aromatic compound and zero order with respect to the aldehyde. If that is indeed the case then you will have evidence that the first proposal to the mechanism is correct.

[@jjppmm29]

you know, at 2160 you can really get a good look at what is behind the camera from the distillation and receiving flask.

[@tedCain1]

your videos are a nice reward. (coming from someone who would never submit an answer)

[@ClownWhisper]

you used to have an actual shortpath aparatus what happened to it didn't break? I broke in about four of them in the past two years

[@amrititbhu]

Hey Nile, there is a process called anti-solvent crystallization. Can you demonstrate it?

[@NileRed]

I kind of showed it in my Lidocaine from lubricant video. kzbin.info/www/bejne/jXKQomemjcljhs0

[@amrititbhu]

Thanks!

[@Gaark]

does this stuff expand as it solidifies like water does?

[@jackgeraghty1548]

What type of distillation apparatus do you use?i really want to know before Christmas.or what is a good one to get, one that has sealing glass joints so you can switch out different columns and condensers.just one that is a reliable good company name and good quality.thanks

[@derkateramabend]

5:30 You can see Nile in the reflection of the round-bottom

[@mpk6664]

derkateramabend ..and?

[@SafetyLucas]

Can you make a video on how to oxidize phenol to p-benzoquinone intentionally?

[@antejl7925]

Boil paracetemol pills in a mild NaOH solution is a very cheap and easy way it goes mohoganny brown.

[@mushroomtoad2000]

can you please do extraction of eugenol?

[@entityrides9313]

just curious but what are your thoughts on schrodingers cat?

[@MuzikBike]

Can you make benzene from PET plastic?

[@Quintinohthree]

Muzik Bike - Geometry Dash and stuff Yes, Extractions&ire did it.

[@leonidandanyabortsov5405]

What about the synthetic version of sarsparilla flavoring? How is it different from the natural, etc.

[@vx-iidu]

Paper towel extraction, Paper towel condenser... do a series on the uses of paper towels in chemistry ;-)

[@Hientran-ib3pv]

how can i take phenol out of glass bottle like that , shall i heat it up ?

[@jb280557]

@NileRed could you help me with a list of chemicals needed to make a similar solution using reductive amenation used for the phenol that wakes you up if you catch my drift ?

[@BackYardScience2000]

Lol! He's already said in previous videos that he will never do that or have anything to do with it. Though you may have luck on the "Walter White" KZbin channel.

[@fatalcomprehension]

Umm.. BTW. I wonder if this might sound ironically dumb.. ... But is it possible to create tert-butyllithium in lab safely?

[@fatalcomprehension]

Hmm.. It's really toxic,really reactive and really inflammable right ?

[@fatalcomprehension]

Well yeah lol

[@Quintinohthree]

Nish Thapa Depends on what equipment you have and how you define safely, but in a home setting it's impossible.

[@fatalcomprehension]

That's tough...

[@hartmehler6069]

Could you do a video of your lab materials and everything you use? Please.

[@rakinkazi9780]

that's gonna be colorful

[@KnakuanaRka]

0:17 Counting the atoms, there should also be a water molecule on the right side of the equation to make this line up. Not all that important, but the equation is still incorrect.

[@AllChemystery]

why were you wearing a respirator?

[@jackm2379]

better safe than sorry

[@LilGugz]

And phenol smells disgusting, always makes me feel light headed when I work with it

[@bsheaves]

Because the lethal aerosol concentration is in the parts per million

[@Ryoka242]

First mechanism would require a lot more energy than what you could provide.

[@Kieranlb05]

Am I still being promised a mercury distillation also how do I clean gallium metal

[@NileRed]

I will clean gallium eventually. Right now Im not sure how to clean it though. Also yes, I will keep promising (an eventually deliver)

[@lexaf7578]

You can clean gallium by melting it in water and adding a bit of sulfuric acid

[@Kieranlb05]

NileRed I did try a warm water method seemed to get the oxide solids out by something similar to gold panning

[@AwsomeVids83]

Nile, I have a channel recommendation for you. It's for a channel called Derek's Lab, and he only has 50 some subscribers, but I feel that he deserves far more. Any chance you could look at his channel and maybe do him the favor of making a quick mention of his channel at the end of one of your videos?