Sulfonation: p-Toluenesulfonic Acid

[@covodex516]

why haven't I found your videos earlier? your explanations are superb; quick, simple but without too much of dumbing it down. works perfectly for me.

[@jasonpatterson8091]

Miss you Doug!

[@NikKappa]

Why did he stop making videos?

[@crabcrab2024]

You deserve more subscribers!

[@michael3263]

Fan-freakin-tastic! I was just about to investigate the synthesis of a decent hydroxyl protecting group. It's good for getting certain recalcitrant SN2s to work as well. Thanks, Doug!!! You really brighten up my day! 😀😊

[@petkotzvetkov6528]

Great, so great to have you back!!

[@pk10x]

I am loving your comeback on KZbin! keep up the excellent work!

[@nunyabisnass1141]

Professor K still loving it?

[@lajoswinkler]

Nice work. Could you do yield calculation in the future?

[@astralchemistry8732]

Have you planned making tosyl chloride and then tosylate some alcohols?

[@jacobtierney4419]

Astral Chemistry this I would LOVE to see

[@Grak70]

I'd love to see this as well. Unfortunately probably involves thionyl chloride or some other nasty materials.

[@mrfantasticguy6385]

Love your videos! I was wondering if you could make a video on how to clean glassware as I think it would be helpful for other amateur chemists

[@Berghiker]

When distilling sulphuric acid, can I use a PTFE magnetic stir bar or will it get totally destroyed at 380 deg C?

[@antejl7925]

What would be the ideal solvent for a purity recrystalisation? Methanol?

[@baileymclean1021]

How could you convert that to toluenesulfonyl chloride?

[@RaExpIn]

I very often thought about whether this is possible, because of benzene being easily sulfonated, too. I might give this a try in the future. Nice video! :)

[@Berghiker]

If the sulphuric acid is very clean but just diluted, can you not evaporate all the water off at 200 deg C?

[@rabidchipmunk2641]

13:49 Those are some weird tongs.

[@nanobytez6881]

They're flesh tongs!

[@kcore9688]

hahaha I came to the comments as soon as i saw him do that lol

[@fano72]

Decent preparation video!

[@ScienceWithJames]

When is that long lab tour coming?

[@TheDuckofDoom.]

sodium carbonate is also available as arm&hammer "washing soda" in the laundry section of many stores near the borax and blueing, alternately it can be formed by heating sodium hydrogen carbonate (bicarbonate) to over about 90c dry or wet. (actually decomposes at room temp but very slow(months-years) only seconds in boiling water, the resulting carbonate is heat stable to several hundred degrees.)

[@michael3263]

wolfedog99 I use the arm and hammer washing soda as a source of sodium carbonate as well. It works great for everything I've used it for thus far. And it is so easy to turn it into virtually pure NaOH. Every home chem lab should have some. 😀

[@MrTk6969]

@dougslab Can u do a video on p-toluenesulfonylhydrazide

[@arulexport2701]

Alkenes. Sulponation process also same procedure?? Really i like this crystal clear explanation and demo Thank u sir

[@johnblacksuperchemist2556]

THIS WHOLE VIDEO IS GOLD............I wander if you could use the same process to get thiophenes out of fermented ethanol.

[@htomerif]

This is just a suggestion from someone who doesn't know much chemistry, but I find that I have an increasing lexicon of chemicals that I know how to synthesize but not necessarily what I can do with them. If it isnt too difficult, maybe just telling us a few examples of what the particular thing you've synthesized can be used for would be helpful. Its kind of like programming, the more elements of an API you understand, what you can get done with it increases exponentially.

[@spookywizard4980]

It would be nice if you did a yield on the acid

[@AleX-qe8mx]

Wow 🤩.... Love your video .....

[@dudumaurina2]

Hey Doug, can you tell us where to buy that rubber scraper? Thanks man, love your videos, It's awesome that you are back.

[@DougsLab]

Hey, thanks! I got them a long time ago and I'm not really sure where... but to get you started, go on Amazon and search for "rubber policeman." I'm not joking, that's what they're called.

[@zinrice3244]

How does water cause precipitation? Won't water reverse the reaction back again?

[@KowboyUSA]

Sweet. A nice relaxing chemistry video before I hit the hay.

[@chrisjones-fp5vd]

I think it's called a Barrett receiver when it has a stopcock on it.

[@bradbilly2791]

I found your channel because of Nilered. Your videos are equally as good. I'm learning a lot. And may one day go to school for chemistry. Very interesting stuff.

[@noodlesoup2281]

Doug's channel and content is far better atleast Doug has some original vids, red copies everyone else's work and does a terrible job at that low yeild dirty messy reactions, one thing il give him that hes good at is milking KZbin algorithms.

[@aga5897]

Awesome video prax. Wish i knew how to do those reactions.

[@bludeat7398]

and what about ortho product? it wasnt made because of steric effects?

[@kalrbaum]

since this is an equilibrium reaction, the most stable product (the para isomer) is formed

[@shonkysidewayssam6134]

Awesome stuff!

[@nicktohzyu]

could you explain why vacuum dessication is better than dessication at atmospheric pressure? what i was taught in school is that partial pressures of inert components don't affect the phase change rates

[@filipealarza9079]

I suppose it's because water has an easier time evaporating at lower pressures.

[@williamwijaya6679]

Hmmm.. where you buy your rubber scraper?? looks greatt.. please let me know Sir

[@BackYardScience2000]

Google "rubber policeman". That's really what it is called.

[@johnlinley4375]

It is, perhaps a silly question, but it has been more than thirty years, and you remind me of why I miss it so. Why is it para? Is it that the meta comes at a higher temperature, or some resonance effect, or are you getting a mixture, and just didn’t mention it?

[@DougsLab]

Not a silly question at all! Para is favored in this case because of the ring activation effect of the methyl group, which is an electron donor and contributes electrons to the resonance via conjugation. This contorts the electron density of the ring to favor ortho- and para- species. Since there are two ortho- sites and one para- site one would expect more ortho- than para-. However, the steric bulk of the methyl group means that for sulfonation in particular, the para isomer is favored over all other outcomes by a huge margin. It is less stable next to the methyl group and will readily rearrange to the para- position at high temperatures. Had I used SO3 in H2SO4 and kept it cold, I could very well have had a significant percentage of the ortho- product.

[@moritzschaferalthaus3461]

Doug's Lab Hi,i have a question. In the last Lab Tour you said you will make a more detailed Lab Tour.Will we see that in one of your next videos?

[@acx01bc]

I did thisone, just refluxed (density > 1.6) h2so4 with toluene together with a little s2o7 obtained from electrolysis of diluted h2so4, I got a bunch of crystals.

[@yavuzderin9855]

Why did you wash toluen with Na2CO3 solution before dean stark ? Washing with a base should have been last step, isnt it? What is the reason of your Na2CO3 washing ?

[@spiderdude2099]

Yavuz Derin he did it to remove the methylthiophene sulfonic acid like he said at the beginning. The first part was just to remove the thiophene.

[@guywiener6391]

What is the best and safest way to dilute tosylic acid?

[@spiderdude2099]

Guy Wiener just dissolve it in water. It isn’t exothermic like sulfuric is

[@Grak70]

Makes a great leaving group for alkyl alcohol elimination by a nucleophile.

[@stamasd8500]

Thank you for this video about the too silly acid. :)

[@ShroomLab]

Does this work with styrene as well or will it polymerize in the process? I mean that would be incredible to make some acidic polymer film after polymerizing the p-styrenesulfonic acid. Thanks for this video anyway, I really enjoy each of them.

[@a.nonymous9877]

I expect it to react: 1-phenylethylium, as a benzylic carbocation, is relatively stable and could lead to polymerization, formation of (1-phenylethyl)sulfuric acid, etc.

[@tmfan3888]

3:38 y the toluene became cloudy b4 u added the H2SO4? 9:45 btw u should add H2SO4 b4 toluene 2 maximize ur yield since toluene is already in excess

[@DougsLab]

At 3:38 I had already poured some but stuttered or messed up my narration so I had to start again! Good eye. At 9:45, since the toluene was wet it was better to add the acid to it rather than the other way around for the same reason you shouldn't add water to acid. It could have resulted in a lot of toluene vapor escaping the flask.

[@toseltreps1101]

ur 1 dumbass

[@Jayko30]

0:57 "used in some upcomming reactions" .... they never came....

[@science_and_anonymous]

Still would live to see a video completely devoted to solvents

[@MrTk6969]

Can you do a p-toluenesulfonylhydrazide synthesis @dougslab

[@williamackerson_chemist]

I've been wondering how to run a proper sulfonation fro a while now. Do you think this would work with naphthalene to yield naphthalene sulfonic acid?

[@DougsLab]

Not really. If you're looking for 2-naphthalenesulfonic acid, it's pretty simple. The high BP of naphthalene allows you to simply mix naphthalene with sulfuric acid and hold that at a little over 100C to continuously remove water. You literally just heat the two together for like 24h and allow steam to escape, then do an acid/base workup.

[@williamackerson_chemist]

Thank you. This makes sense. Great video by the way.

[@beanlets]

What about making p-xylenesulfonic acids

[@NatasPvPMontagesz]

Hi from Brazil!

[@DougsLab]

Well hello there!

[@bernardo00124719]

quem se importa?

[@zodd0001]

Good work ! What's your next experiments ? Do you accept suggestions ? The mine would be synthesis of vanillyl amine.

[@christopherleubner6633]

This requires oleum for good yeild but a little P2O5 can be added as a catlyst, makes the phosphonate first that becomes the sulfonate 🤓

[@flaplaya]

Love the comment section... Got some true geniuses tapping away.

[@Krawacik3d]

And what with this ~40ml of trapped Toluene in Dean-Stark apparatus? It just didn't react with H2SO4? Did you count it as a loss?

[@DougsLab]

A large excess of toluene is always needed to drive the water removal mechanism. In this case, sulfuric acid was the limiting reagent by a large margin. However, the toluene in the dean-stark trap is clean and can be dried and reused for other experiments.

[@thegreatga]

Should fill up the trap with toluene first, that's what we do when we make 4,000 gallons of tsa.

[@bdnugget]

This is the first time I've ever seen white p-TosOH. Ours is always pink or even purple-ish.

[@pooriaeslami6752]

yeah. like me.

[@bdnugget]

@@pooriaeslami6752 that's normal, don't worry about it. It being white seems more rare

[@riccardoblaso8017]

Nice synthesis! This method is more secure because it hasn’t use oleum. Make a video in which you show your new laboratory!

[@siddharthkhemka1432]

Hey Doug very nice video, can you also show hydrolysis of sulfonated toulene with NaOH to make para cresol. Also can I reach you on email somewhere ?

[@gayrainbowunicorn1367]

Can you buy oleum in your country ?

[@snowdaysrule]

Hey this video is perfect timing! I was FINALLY able to buy a gallon of toluene the other day (and trust me I've been looking forever for it) so might have to give this reaction a try!

[@theterribleanimator1793]

snowdaysrule2 why would you need a gallon of toluene?

[@snowdaysrule]

Yea a gallon is absolutely overkill but my options were either that or a 5 gallon pale! So relatively speaking I bought the smallest quantity they sold. It's more than I need, but was super thrilled to have found it locally

[@TheDuckofDoom.]

Used for thinning and cleaning certain industrial epoxies and paints as well as an octane rating booster in gasoline blends. chemically similar solvent to xylene but it evaporates faster. Also mix 1:1 with methyl ethyl ketone (acetone seems less effective) for one of the strongest solvents I have found for gunk and gum in the nooks of mechanical bits. (dried up bearing grease, gasket and sealant residue, stagnant fuel gums, sticker residue) Soaking parts in a metal or glass container with some agitation is fine but work fast with gloved hands, it has a fairly short breakthrough time on most glove materials including nitrile, which is not the case with either solvent neat. Also this only seems to work undiluted, adding any significant gasoline to stretch the volume (for soaking large parts) seems to destroy the effect and has only the solvency of basic gasoline.

[@snowdaysrule]

wolfedog99 Will keep the 1:1 toluene/mek combo in mind when cleaning up the metal parts in small engine carburetors thanks!

[@DougsLab]

Congratulations on your purchase! Toluene has a lot of uses in the laboratory, and I think a gallon might not even be enough! It can be oxidized by permanganate to benzoic acid, or nitrated and diazotized to make lots of azo dye precursors. Nitrotoluenes can also be reduced easily to various toluidines, and a sandmeyer reaction can give halogenated toluene derivatives. It makes a great benzene substitute in a lot of old procedures which call for benzene, a great nonpolar blending solvent for TLC, the prime mover in a Dean-Stark setup, and all of this is barely scratching the surface. I'm excited for you. :D

[@imrankhan-gl4jb]

Nice bro

[@sharmaineabdulaziz216]

im here because of fucking online class. we cant do actual experiments :((

[@hardikmhatre7075]

Hey Doug I am Hardik can we use toluene from lacquer thinner in making of toluenesulfonic acid ??

[@Spycyzygy]

Hardik Mhatre yes Fractionally distill it to get toluene(look up nurdrage’s video) Then you’re good to go

[@CryptoFrenzyX]

Can i use 15% sulfuric?

[@lautaromorales2903]

for p-TsOH syntesis the reaction needs no water, so it wouldn't work untill all water is distilled over. it's easier to concentrate the acid by boiling the water first.

[@papaversomniferum5247]

Hey man! Can you do a refining video on palladium or gold... orrrr silver? Lol please, that's what I focus on, and I'm curious to see other people's experiments and different variables in everyone's steps. I know most are straight forward. However it would still be cool to add that content to your channel :) cheers

[@vinnyb113]

Good videos

[@garrysekelli6776]

Doug is mia. What has happened to Doug?

[@MasudRana-dr4xg]

nice

[@StevenSchoolAlchemy]

Cool beans.

[@fmdj]

Since you're using a Dean-Stark apparatus to drive the reaction, is it critical to use highly concentrated sulphuric acid or could it work with less concentrated sulphuric acid?

[@DavidRobertsonUK]

Re the thiophene removal step: I found that just stirring magnetically with the sulphuric acid didn't efficiently sulphonate all of the thiophenes. After adding to a separatory funnel and shaking vigorously, the acid layer became very dark, and actually turned blue (?!). I had to discard the acid and repeat the acid washes 5 times until the acid layer was only a pale yellow colour.

[@justusfelix2441]

David Robertson i have the same problem. I think our acid is not pure

[@gayrainbowunicorn1367]

I have liters of Oleum 20% SO3, but i live far away....

[@boris7797]

give me some oleum

[@jamesparslow4939]

Me tooo

[@pooriaeslami6752]

Hi I repeated like you but solid isn't white

[@drinventions9742]

I honestly have no idea what you just made,, BUT as always Very Interesting,,, I do have a question since I’m the First commenter,, can you extract cyanide from seeds, then dissolve gold with that cyanide?

[@ScienceWithJames]

DR Inventions if you are talking about apple seeds, there is not a very large amount of cyanide in them, but maybe CodySlab could do that.

[@drinventions9742]

Actually I’ve heard that walnuts with the hull,,( the part that surrounds the Nut shell)has a decent amount in it,, the old timers use to tell me stories about how they’d gather up a bunch in a burlap bag an throw it in a pond, and in a matter of minutes the fish would just float to the top to be netted up,,but you know old timers an they’re stories

[@TheDuckofDoom.]

Fresh bamboo shoots have a fair amount of a compound that forms hydrogen cyanide in contact with stomach acid, mg per Kg of course but enough to be potential health concern under certain conditions. The compound decomposes at cooking temperatures.(near boiling for a couple minutes, not just warmed) Peach kernels(bitter almonds) are also known for cyanide.

[@drinventions9742]

Well the real question is,, can you separate the cyanide from mother solution of juice extracted from seeds or seed parts an other yielding plants to successfully dissolve Gold or would you even need to extract the cyanide out to do it.. I just think it would make very interesting video,,

[@DougsLab]

Yes, you could technically accomplish this. However, the yield would be too low to make it worth the effort. There are other, much easier ways to get cyanides from hardware store chemicals rather than hundreds of pounds of apple seeds and cherry pits.

[@saadeddinechabani5770]

🤝🤝🤝

[@qwertyqwerty-cx8qn]

p-TSCl

[@FrugalGarden]

Hi from Ohio

[@koukouzee2923]

I wonder if you are in jail and that's why you are not posting :(

[@JustinKoenigSilica]

oh wow it's not pink our laboratory pTSOH is pink for some reason.... :thinking:

[@jpdemer5]

You get a pink product if you don't do the preliminary clean-up with cold sulfuric acid. It's a very minor impurity; you can recrystallize from aqueous HCl to remove it.

[@marinogarym]

Using "wet" toluene will hurt your rxn - You'll spend a lot more time collecting water. You should have dried it with Copper (II) Sulfate, first. It's my personal favorite for benzene and toluene.

[@jpdemer5]

You'll spend just as much time with the drying, filtering, and clean-up. It is a good drying agent when doing solvent-solvent extractions, though.

[@christopherleubner6633]

Indicating too 🤓❤

[@extracrazyguy]

I tried the recipe ... my ketamine never tasted worse

[@Issveinn]

I like your videos a lot...but I had to turn the volume down, because you are continously talking and talking and talking and talking and talking, that gaves me a little headache ;-) .

[@Spycyzygy]

#TheBench

[@realcygnus]

I guess there is a 0% chance that you'll make..... 1oz of fentanyl, with a...... $treet value > the GNP ...... in a future vid !?

[@michael3263]

realcygnus Even if you were able to successfully make it you could die from trace contact with it. I worked at a plant where fentanyl was made and whenever we made it an EMT with a shot of naloxone had to be in the building on standby at all times and the reactor vessel was so contained you'd have thought we were making weapons grade anthrax.

[@realcygnus]

oh I bet.........there are even analogues 100X more potent.........it can be weaponized........the CIA(& other$) wouldn't even allow it........you could find detailed instructions on uranium purification/nuke making much easier........its the kind of thing where the information alone is threatening to the Global Economy.

[@michael3263]

realcygnus Um, you're talking about carfentanyl. No one uses it (except the Russians) because it's so insanely potent that it's almost useless. The therapeutic window is so small. It's like etorphine. You don't see that used in people even by drug cartels because even though it's 10,000x stronger than morphine it's so strong it could very easily kill the user.

[@xClaudiaOctaviax]

stay away from twitter.. bad juju

[@mistertheguy3073]

The background noise is making my headache worse :(

[@DougsLab]

Yeah, sorry! I wish there was something I could do about that but the fume hood fan is necessary to keep me safe. In my next laboratory I think I will put the fan in the attic and run a long tube instead, which might help with the noise.

[@mistertheguy3073]

Doug's Lab normally it isn't a problem, but I'm sick atm and it's annoying to have to wait before I can watch your vid :) I love your channel and I'm so happy you're back!

[@phonotical]

slow down

[@michael3263]

phonotical You can add captions and slow down playback you know. I know it can be hard to follow but if you add the captions, re-watch the difficult bits, and ask questions instead of making demands I'm pretty sure that most on here would go out of their way to help you understand.