Synthesis of benzoic acid from toluene. The permanganate method in depth ⚗️📑🔬

#chemistry #benzoicacid #organiclab
Welcome to my new video! Prepare for some more in depth chemistry than usually in my channel, also for some relaxing close up shots!
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[@johnathancorgan3994]

This was a very nice combination of science, chemistry porn, and glassware ASMR.

[@GarwoodNick]

Great clean apparatus! I think you're really charting new territory for KZbin chemistry here with a visual production that exceeds NileRed but with the technical depth of NurdRage and Doug's Lab.

[@Glattuh]

Hi and thanks!! A+ interchange is quite good, I am pleased to have sponsorship with them!! Also thanks for those inspirational words! NurdRage and NileRed are two of my biggest references! In fact I started studying chemistry at the universit, along with other things, because of their videos! I just loved the way one person can mix reagents to change matter properties and give it helpful uses ;D Here is the link to my organic kit if you want to do some research or even purchase ! : www.dixonscience.com/product/48385/Organic%20Chemistry%20Kit

[@johnathancorgan3994]

I usually don't like text-only narration but here the combination of soft ocean wave sounds, the steady clink of glassware and hum of the vacuum pump, and various camera angles was fantastic. That *and* the scientific detail just made it awesome. The only thing missing was the clip of Pink Floyd at then end...

[@Glattuh]

Haha thanks for your comment! Really apreciatte that! Only for that i think the next video will have a pinkfloyd short sound at the end ;D

[@ELBlDu]

@@Glattuh yes on Pink FLoyd

[@petevenuti7355]

​@@Glattuh cought that! how about some obscured by clouds or echoes 🤔

[@-r-495]

I really enjoy the crystallisations, excellent recording!

[@clintongryke6887]

Very interesting, informative and thorough.

[@johnathancorgan3994]

So happy you're back.

[@Glattuh]

Thanks!!! Expect some music in the video hehe

[@charleschidsey2831]

Excellent presentation in virtually every way! Love the stoichiometric analysis and the crystal lattice information, the latter of which I have not encountered prior to this in any YT videos. The graphic depiction of the crystalline structure is superb. My only recommendation for future videos is to consider a flat black background rather than white since most organic compounds are either white powders or colorless liquids. Also, since you have opted for a scholarly approach and obviously have access to incredible graphics capabilities, I would include a discussion of the reaction mechanism (if known), such as substitutions, eliminations, rearrangements, etc. Once again, bravo for the outstanding work here. You have earned my subscription.

[@Glattuh]

Thank you very much! As far as I know the mechanism of oxidation with permangante is not well known. Thanks for the advice, I wish I had more resources to film it in better conditions :D

[@Glattuh]

Here is the stuff I used in the video, thanks to my sponsor!!! : - Organic kit 19/26: www.dixonscience.com/product/48385/Organic%20Chemistry%20Kit - Heating mantle, digital range: www.dixonscience.com/product/... - Hotplate magnetic stirrer: www.dixonscience.com/product/...

[@thatnonchalantguy]

excellent video quality 👏💯

[@mirekbrdek4350]

Thank you for the information, yes I saw your latest videos recorded by Lumix G9, it's really impressive, both in terms of content and editing quality, great shots and of course the resulting quality in 4K, but I'm shocked by the excellent quality of FZ1000 in FullHD resolution, BRAVO! I look forward to your next videos. Cheers Mirek from the Czech Republic

[@Glattuh]

Yeah I think Lumix is a great camera brand and they are doing things really really well! Not sponsored by them yet but hey, who knows :D Thanks for your comment!

[@LEBANON707]

I liked the step by step approach ...One can see you enjoy what you do ...quite inspiring!

[@Glattuh]

Thanks! Indeed, I really love it!

When I've done this reaction in the past, I used to filtrate all the reaction in an Erlenmeyer flask. The remaining manganese dioxide solution was rinsed with water and the filtrate was added to the separation funnel and then separated in the two phases. But also in this manner was a good experiment. I love it. Greetings from Italy.

[@Glattuh]

Yeah that is another way, but if the use of solvent can be skipped.... much better! Thanks, nice to hear you saw me from there!

[@mirekbrdek4350]

I like the excellent image quality, what camera and lenses did you shoot it with? BRAVO!

[@Glattuh]

Thanks! All the footage was recorded with a Lumix FZ1000, a non interchangeable lens camera. Now I upgraded my quiment so if you like the quality of this one check out my latest two videos :D Thanks for commenting!

[@donalkevin6901]

Very pure. Good work 👍

[@Glattuh]

Thanks!!!

[@sciencek]

I really love this love ! Very good job 👍🏻. I love your animation and your explanations for the equations et crystal structure. Continu !!

[@Glattuh]

Thanks for the feedback!!!

[@burkaahmed5222]

A very interesting way of teaching or showing thank you so much!!

[@Glattuh]

Thank you for your time! Nice to hear you enjoyed it!!!

[@nandi123]

Nice demo. Some tips: Always put your stir bar in the flask before any chemicals in case it breaks the flask. The water should enter the condenser jacket from the bottom port an exit at the top. Don't fill reaction flasks more than 50% full. Use a funnel to pour things in to flasks with ground joints. You can simplify your workup by distilling the excess toluene from the reaction flask and by filtering through Celite.

[@danarchy723]

If that's hardware store toluene you are using, you should purify it by adding sulfuric acid to it first. Doing so crystalizes the sulfides in it that distill over with the toluene at the big distallation plant. The boiling points of the two chemicals are really close to each other. After crystalize the sulfides, filter it, neutralize with sodium carbonate solution, add a bunch of sodium chloride to make the water dinse, decant, and add magnesium sulfate, let stand for about 2 hours, then you can add your potassium permanganate solution.

[@manasatextiles7035]

Casticsoda tuluane to sulphuric acid mixing kaise karte hai sir Batav please thanks

[@Kassblue043]

Thank you very much for making this video. It really help my assignments. By the way where can I found the reference for the theory in the video?

[@Glattuh]

Ni ce to hear that, thank you! Unfortunately I dont record the sources when planing my videos. I pretty much use public data to do them. Also I can say that pretty much 100% of my procedures are by myself so to say. I may replicate other people work but I perform them in my style. Also, most knowledge shown, for example in this video, comes from "me". If you have any questions feel free to ask me here so people can see it or privately. You can see my email here: kzbin.infoabout

[@garycard1456]

Your outro theme reminds me of the start of the song "I want to break free" by the 80s rock group, Queen

[@lucianoperitore7891]

great video, especially to explain the process. But I don't know why you didn't follow the reaction quantities. for example you used such as 8 times the molar amounts of toluene required for the mass of kmno4 you weighed. Another thing is that i can't understeand the yields, your theorical massive yield for the benzoic acid had to be 9,0758 grams (0,05665 mol) if you used something like 17,9 grams of kmno4 (0,1133 mol). So the yield of benzoic acid had to be around 21%, if we see the mass that was formed theorically (9,0758g), or around 4% if we see the mass of toluene that you waighed.

[@Glattuh]

Ok I see what your question is, I was honestly a bit lost at the first read. Let me explain: A stoichiometric reaction shows how many molecules react of every reagent to produce certain molecules of product and byproducts. Who speaks of molecules so speaks of moles too, they are the "same". That doesnt mean that I used the stoichiometric amounts to get my reaction mixture!!!! That a veru different thing and this is the key of your question. I added toluene in huge excess. We chemists speak of what we call the limitant reagent, which in this case is the permanganate. And it is very convinient!! Permanganate tends to be very reactive and the byproduct is insoluble in water so I added a huge excess of toluene to ensure all of the permanganate reacts. The excess toluene, as you saw, is simple to be separated from the reaction mixture. Also excess toluene forms an azeotrope with water and increases volume of the mixture, as bigger quantities are easier to work with. You can think that toluene acts both as reagent and solvent (partially, as there is water too). Hope that helps!

[@staticinteger]

Fantastic video! I was wondering if you could provide me with the paper / reference you used? :)

[@Glattuh]

The info behind all my videos is a mix of quick looks to papers, wikipedia, databases of chemical compounds and videos on YT... Sorry, I cant provide them all. If you have any question feel free to ask!

[@oskardumanski8538]

Приветик! Wouldn't be safer to grab the neck of the flask in case you spill out something accidentally? I can see many items (heating mantle, Simax bottle) available for those, who want to perform chemical experiments at home. ;) Would you recommend such a heating mantel? Does it work well? I understand your passion very well. Subscribed.

[@Glattuh]

Well you are actually right! I just sometimes feel so confident handling glassware that I dont even imagine that something bad may happen, which it could alsoo!! Many years of experience and never had an accident hehe About the heating mantle... Yes!!! I am pretty happy with it. On the other hand I had an issue with it and it is the following: without the thermal probe the temperature set is not the actual temperature of the plate. And also my sponsor wants me to say it out loud, let me explain. If you want to boil water and set it to, let's say; 105ºC and erlenmeyer with water will never boil. You have to set it like at 200ºC or even more for a faster boil which is a bit dissapointing even though once you get used to it, its's just ok. With the probe also it works 100% well! The temperature rises pretty fast and precise! Again and as I said, I am pretty happy with it. The materials used and performance are extremely good and durable. I have done many experiments on it and it always have exceed the expectations. If you want to research more follow or even purchase one the next link: www.dixonscience.com/product/47970/Hotplate%20Magnetic%20Stirrer Thanks for commeting!!

[@oskardumanski8538]

​@@Glattuh I think better worry than sorry. The neck grabbing seems to be more comfortable in case you would need to transfer hot liquids. I meant a mantle, not a plate. I've found it already, unfortunately, there are no sizes I would consider to purchase (2000mL), and that link you have shown to me contains a very expensive item - for that price you can get a full set for distillation with the heating mantel for round bottom flasks. On the other hand, I rather do not need a hot plate (hydrodistillation, Soxhlet extractions). I think the temperature sensor on the device like a hot plate or heating mantle is not the best idea - you always suffer some losses of energy, so the temperature should be monitored in the place where you want to have the desired value. Thank you as well.

[@nutbreaker22]

Is there a reason to put toluene in last? I'm I doing something wrong, when I pour a substance, that will oxidize, first? By the way, this is the most cleanest presentation I've seen about oxidizing with KMnO4 ! Wow!

[@Glattuh]

Thank you! I dont quite understand your question... The toluene is oxidised by the permanganate as it is converted into benzoic acid. Excess toluene is added to ensure all the permanganate reacts.

[@petevenuti7355]

I think most of the time the order of addition only matters in more energetic/exothermic reactions.. like with the heat of enthropy when you add acid to water vs water to acid... sorry can't provide the math..

[@Jasleen9294]

what is the reaction between h2so4 and filtrate

[@Glattuh]

I asume you refer to the neutralization step (as I didnt use sulfuric but hydrochloric instead ;D). The reaction is quite simple: 1C6H5COONa (aq) + 1HCl (aq) = C6H5COOH (s) + NaCl (aq) Hope that helps

[@Andrew-my1cp]

I need your help.. I am looking to make p-nitrobenzoic acid. I was originally going to use potassium dichromate for the oxidation but after looking at the msds I quickly opted for KMnO4 instead due to toxicity issues. My question is, how would you react the p-nitrotoluene with the KMnO4? What solvent would you use and how do you figure out how much KMnO4 you'll need? Would it be just as simple as refluxing a solution of both in water? Help is greatly appreciated, thank you.

[@Glattuh]

Hi! Probably you just need to replicate the conditions as in this video. I am sure p-nitrotoluene is a liquid too, inmiscible and less dense than water. So by becoming in contact with excess KMnO4 solution you will get the same reaction going :D

[@GameDevCaptainBlack]

p-nitrotoluene is melting in 55 °C, first melt it, prepare KOH + KMnO4 solution but use little water as you can. Water has H+ ions as well, and they consume KMnO4 electrones. KMnO4 absolutely use with KOH... that would be a rocket.. %85-90 yield. Thanks for video.

[@PaulSt-Germain-c7u]

Very nice video. Can benzoic acid be decarboxylated to benzene with NaOH + CaO?

[@Glattuh]

In theory, yes! I do not really know the experimental conditions though ;(

[@LucaLBO495]

Justo a tiempo, ¿ Dónde conseguís tus solventes?

[@Glattuh]

Hasta la fecha los he conseguido en una drogueria cerca de donde vivo en Madrid. Es una tienda muy famosa entre los químicos locales, incluso tiene historia O: Si estás interesado te dejo el siguiente link hasta su página oficial :D manuelriesgo.com/

[@Prchemist06]

Hey mate ,can ya show your calculations here for the amounts you presumed ..?

[@Glattuh]

Hi! Many of you are asking about the calculations/procedures. In most cases I just create them to fit my necesities for the video. I am starting to think to build a webpage in which we can talk more deeply about some videos/questions you may have. I am still evaluating this. Thanks for your comment!

[@Prchemist06]

@@Glattuh merci beaucoup

[@liltr3w339]

Anyone knows exact efficiency of that process? and also efficiency of particular steps?

[@fugz]

Lovely video. Such good framing and camera work, the graphics are really nice too. Is the noise floor from ventilation equipment or is it just white noise added in post? Either way I do like it :P

[@Glattuh]

Hi! Thanks for the comment! The sound is coming both from noose fron the camera and white noise added in editing. I made that sound myself as I once used the sound of the sea from a YT video and have copyright issues.... ;}

[@Dominik9283]

Hey! Nice video! Still got one question: is it also possible to do it the other way, so you get toluene out of benzoic acid? I nedd to ask because Toluene is much more valuable for me. Hope for an answer :)

[@Glattuh]

Hi and thanks! It is possible but not worth it at all, less than trying to get benzoic acid from toluene. I can imagine at least 2 ways of doing that, and both requires more energetic materials (also more expensive and difficult to get). If there is any interest in doing that is only for academic/entertainig purposes. If you are interested in toluene it can be get cheaply at drug stores as paint thinner. I got mine a while ago for exactly 6,29€ a liter.

[@Dominik9283]

@@Glattuh oh, ok thanks for your advice!

[@spiderdude2099]

I like how the exact mechanism of this rxn is still not fully understood

[@chemicalmaster3267]

+ Nation Of Our Hobbies Hey, Nation Of Our Hobbies! I am curious to know if you can do some videos about some synthesis and other reactions that I have in mind. Is it okay to tell what it is and if you aprove and could do?

[@Glattuh]

Hi! Im having problems with this coment, inmediately after responding you it autodeletes. Find my email on the channel description (bussiness contact)

[@chemicalmaster3267]

@@Glattuh I think I´ve found it. I´m gonna write my requests right away. Hope I didn´t forget anything or made any mistake.

[@alllove1754]

I can give you a way to skip a lot of this, though you still might need to distill the liquid. You need a container, a beaker or a bottle, with water already half way filled in it. Pour in your toluene infused mixture. Cap and shake. Separate organic, top layer. Alcohols and esters stay behind in water. Then distill your organic solution.

[@grhinson]

wow, i just researching benzoyl chloride...

[@aetheonpro396]

Would prefer to make toluene from benzoic acid instead

[@TheMaskedRacoon1]

Cool.