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Preparation of toluene and (de)sulfonation in detail

Astral Chemistry - 2017-03-21

We take a look at the chemistry of sulfonates and prepare toluene from para-Toluenesulfonic acid. Enjoy!

BlueChem - 2017-03-21

I think it is important to explain the theory behind what goes behind what you do. Great job explaining the reaction and showing it in the lab; you really hit both sides of the chemistry. Maybe you could demonstrate other EAS reactions like Friedel-crafts or halogenation?

Astral Chemistry - 2017-03-22

Thank you! We definitly plan to do halogenations.

JAWWAD - 2018-10-03

Of course I would be delighted to see more of such awesome content!
one little problem- voice synthesizers are not really made for chemistry and sound really mechanical.
I would love to hear these narrated in your own voice instead please :) ...

Kris - 2017-08-18

Hey. I’m glad I stumbled on your videos. I like the mix of practical chemistry and light explanations of mechanisms. Obviously every reaction is different and some might need more explanation than others but it’s nice to have some explanation at least either up front or before each step.
And what do you mean by the toluene smelling better? I guess I’ve never smelled crude toluene. I’ve always worked with pretty pure stuff.

Astral Chemistry - 2017-08-18

Thank you very much!! Compared to crude, technical toluene with a slight benzene and naphtalene aroma this smelled much cleaner and much more like toluene thats used for chromatography.

P. F. - 2017-03-24

Thank you. This type of explanation is valuable. Of course it would be great to see the magic of aromatic substitution and the sulphonates themselves further expanded. Is there a home-approachable green chemistry version of aromatic sulphonation and its reversal?

Astral Chemistry - 2017-03-24

In my outdated opinion it does not make sense to look for green chemistry approaches for sulfonations as your substrate itself is a homo or polcyclic aromatic hydrocarbon which itself is pretty toxic and carcinogenic (at least most of them).
As for desulfonation, it is a common method to just use very hot steam. This is enough to facilitate the desulfonation. So that could be considered "green chemistry".
Thanks for your opinion!

P. F. - 2017-03-25

Actually I checked it out and found something referring 'silica
sulfuric acid' which I don't understand in: https://greenchemie.files.wordpress.com/2013/02/seminar-on-greener-methods-for-batch-sulfonation.pdf. Maybe it's just sand and acid plus microwave, I don't know. I started to get curious having also been through many UCI Irvine and ChemieRUB organic synthesis videos but there are so many reagents which are unobtainable for garage use.
I quite agree that substrates are likely to be nasty but it's maybe possible to cut down on the solvents which are also none too brilliant. I'm probably much more outdated than you but I might decommission our microwave for nutritional purposes, if I can work out how to try it safelyish.
I really appreciate your videos and if you discussed explanations for some reaction details e.g., solvent volume or condenser type maybe, that would also be interesting.

Astral Chemistry - 2017-03-25

Well, that silica sulfuric acid is just silica gel as you would use for chromatographic purposes soaked in concentrated sulfuric acid. This is probably a good starting point: https://en.wikipedia.org/wiki/Silica_sulfuric_acid And then take a look at the first source. And microwave is not required, check page 15 in the document you provided. They use the microwave when they try to sulfonate polystyrene.
It could actually work but I guess you have to try it out. But please dont use sand because it most likely will fail. Prepare the silicon dioxide as follows: http://www.prepchem.com/synthesis-of-silicon-dioxide/
Condenser types is a very good idea for a future video!

P. F. - 2017-03-27

Thank you for your replies. I'll try this when I am able.

bigrockets - 2018-09-13

please continue with the in depth explanationsl I'm learning from you. thanks!

Charles Chidsey - 2019-07-11

Please continue to show the mechanisms. You might want to do this at the end of the video so those who aren’t interested can tune out. This is what UC -235 used to do and I loved his videos. Too bad he is no longer posting.

Gary Durbin - 2018-05-11

great video i like watching the chemistry and experiment so i can do it myself theory is good but not the primary reason i watch thanks again chem

Spooky Wizard - 2017-12-27

Always do mechanisms! Don't leave us in the dark!

The Gayest Person on YouTube - 2018-03-17

Subbed!
I was going to say nice find on that duran crystallizing dish/water bath from West Germany, but then I heard the radio at the end and figured it’s a lot easier to find over there than here in the states :)

Astral Chemistry - 2018-03-17

Thanks! At least you watched the video until the end.

The Gayest Person on YouTube - 2018-03-17

Astral Chemistry it was a good video so of course I had to. Nice use of openchem btw - I actually found your channel from your post in chemplayers video :)

John Hancock - 2017-03-23

the explanation was cool I guess I more so watch for the practical lab footage and laymen's descriptions of what's going, but that's mainly due to my lack of knowledge and inability to follow along.

I guess to me

YouTube>videos from college lectures

=

erowid literature>patents

but like the other commenter stated it is important in this field to understand why, what, how. That's depending on your target audience you may just want to appeal to people who want to bake a cake and they are here for the instructions and how to, they don't give a shit about what gas yeast releases while eating. I was one of those people I'd just follow literature/videos and not develop any questions about what I just did, so I can't just tweak things when my reagents aren't pure, I don't know what reagents i can substitute if I would like to perform a reaction with what I have on hand, and it fucking sucks and I hate it that this is a skill I'm passionate about that you can't just get into and learn on the job with a professional, I can't go to college, so the road to self teaching is my only option and that brings barriers students don't have, legal risk, sourcing reagents, and when learning researching the credibility of what your learning because things become outdated and the accuracy of theory's could be destroyed tomorrow. I love it though, even if all I can do is bake a cake it's still satisfying to accomplish when the bigger picture is you are assisting molecules to do our bidding.

sorry to rant, just that feeling of being at the beginning while you are among people whom are where you want to be.

Astral Chemistry - 2017-03-24

Thanks for taking your time and sharing your opinion! I guess we all have to start somewhere. The "cake bakers" will turn the video off after 20 seconds anyway...

Michael Ruggiero - 2017-10-27

Sometimes it is hard to hear your reagents. Love the explanations, but a little slide with your reagents would be helpful.

Vanta Black - 2021-10-24

for me it is the only option to get toluene , because in my country it's regulated as a drug precursor

Shonky Sideways Sam - 2018-01-04

Thank you for filling my needs/fix with chemistry and I don’t have to worry about the Hazmat team, or bomb squad etc. showing up. Lol

BioDOC - 2020-09-08

It's terrible that the sound has to be turned up down again because in the middle of the video this terrible and above all horrible loud music is coming

Leonora Jaramillo - 2017-04-08

chido

Cloven Beast - 2021-07-20

Hey man no deal if you don't have ants lol