Doug's Lab - 2018-01-29
In this video, I make p-toluenesulfonic acid by sulfonating toluene. Patreon Link: https://www.patreon.com/DougsLab Twitter: @YTDougsLab Google+: https://plus.google.com/u/1/103236004133559189742
Miss you Doug!
When is that long lab tour coming?
0:57 "used in some upcomming reactions" .... they never came....
I am loving your comeback on YouTube! keep up the excellent work!
Professor K still loving it?
Nice work. Could you do yield calculation in the future?
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
you're awesome
you should make videos dedicated to teaching chemistry
Have you planned making tosyl chloride and then tosylate some alcohols?
Astral Chemistry this I would LOVE to see
I'd love to see this as well. Unfortunately probably involves thionyl chloride or some other nasty materials.
Sweet. A nice relaxing chemistry video before I hit the hay.
Thank you for this video about the too silly acid. :)
Should fill up the trap with toluene first, that's what we do when we make 4,000 gallons of tsa.
Awesome video prax. Wish i knew how to do those reactions.
Awesome stuff!
Good work ! What's your next experiments ? Do you accept suggestions ? The mine would be synthesis of vanillyl amine.
Love the comment section... Got some true geniuses tapping away.
Hey Doug, can you tell us where to buy that rubber scraper? Thanks man, love your videos, It's awesome that you are back.
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.
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?
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.
I need to listen to this in 1 quarter the speeedd y0
Still would live to see a video completely devoted to solvents
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 ?
You deserve more subscribers!
Makes a great leaving group for alkyl alcohol elimination by a nucleophile.
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.
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?
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.
Thank you. This makes sense. Great video by the way.
Can you buy oleum in your country ?
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
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.
Please show all of your glassware and eqiupment in the next video.
Hi from Ohio
Good videos
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.
Nice synthesis! This method is more secure because it hasn’t use oleum.
Make a video in which you show your new laboratory!
Hi from Brazil!
Well hello there!
quem se importa?
I tried the recipe ... my ketamine never tasted worse
How could you convert that to toluenesulfonyl chloride?
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! 😀😊
Great, so great to have you back!!
Hmmm.. where you buy your rubber scraper?? looks greatt.. please let me know Sir
Google "rubber policeman". That's really what it is called.
Alkenes. Sulponation process also same procedure??
Really i like this crystal clear explanation and demo
Thank u sir
I guess there is a 0% chance that you'll make..... 1oz of fentanyl, with a...... $treet value > the GNP ...... in a future vid !?
realcygnus Even if you were able to successfully make it you could die from trace contact with it. I worked at a plant where fentanyl was made and whenever we made it an EMT with a shot of naloxone had to be in the building on standby at all times and the reactor vessel was so contained you'd have thought we were making weapons grade anthrax.
oh I bet.........there are even analogues 100X more potent.........it can be weaponized........the CIA(& other$) 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.
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.
I think it's called a Barrett receiver when it has a stopcock on it.
What about making p-xylenesulfonic acids
It would be nice if you did a yield on the acid
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?
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.
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?
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! :)
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.
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!
DOUG NO, don't give him adeas about nitrotoluenes, he might lose everything.
Doug's Lab Thanks Doug, I'm glad someone out there understands why I was so happy to have found it! I wanted it to use as both a solvent and a reagent. It doesnt mix with water so I can use it in a sep funnel in liquid-liquid acid base extractions. And as a reagent it's super cool because it has benzylic hydrogens on the methyl group, so it's much more reactive than a typical hydrocarbon. You can chlorinate it, partially oxidize it, fully oxidize it, and even turn it into benzene! I hadn't thought about doing any nitrations on the aromatic ring (I generally try not to work with energetic compounds if I can help it) but I just checked out the sandmeyer reaction you mentioned and that looks really interesting. I have sodium nitrite on hand and have done some experiments with nitrous acid and making alkyl nitrite esters before so I will keep the diazotization-type reactions you mentioned in mind.
But anyways I really appreciate you taking the time to respond to my comment with such good info. It was very thorough and thoughtful and I'm glad you're back in the lab making great videos again!
yeah, but please be safe, and don't smell the fumes. BTW, how much did you pay for it?
The Terrible Animator Absolutely safety is always my #1 concern :) It is quite volatile but if you chill it (I left the 1 gal container outside overnight before transferring some to a smaller amber glass bottle) before working with it the fumes aren't so bad. And by the way I like the videos on your channel of the flyback transformer circuits and the sodium chlorate experiments. Did you make it yourself electrochemically? Both of those projects were some of my very first (and favorite) experiments so it's really cool to see that you're doing them too!
Edit: Almost forgot, it was like $30 for the gallon. I believe it goes for $40 a liter on ebay so it really wasn't a bad deal for being able to buy it locally. I'll just need to clean it up a bit to remove the sulfur compound impurities like Doug does in this video.
Thanks, and yes i did make it by myself, though that was the first few grams i made and were very contaminated, i learned how to purify things from there.
And seriously, mind the fumes, i worked a little bit with 200ml of the stuff and i didn't notice that my fume hood wasn't working properly, and i got dizzy and sick for the rest of the day, i gallon of toluene evaporating in the air is no joke. And no, you don't have safety in your first priority, nobody has.
oh wow it's not pink
our laboratory pTSOH is pink for some reason.... :thinking:
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.
How does water cause precipitation? Won't water reverse the reaction back again?
rabidchipmunk2641 - 2018-01-29
13:49 Those are some weird tongs.
Nanobytez - 2018-01-29
They're flesh tongs!
K Core - 2019-09-30
hahaha I came to the comments as soon as i saw him do that lol