Making an Important Precursor from Mothballs
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- čas přidán 21. 08. 2024
- In this video I show how to make naphthalene moth balls into the very useful chemical β-Naphthol or 2-naphthol, which is a very useful precursor that is critical in the manufacture of numerous synthetic dyes.
A slight modification of this process can be used to make 1-naphthol, which is used more often in the synthesis of pharmaceuticals, most notably Zoloft.
Given that this is a longer and somewhat more complex video, it is very likely I made a few mistakes along the way. If you find any feel free to let me know!
Note: Procedure was taken from a sciencemadness forum post. I'll try to find the initial post to give proper credit. This one was a little much to rely exclusively on Wikipedia this time.
#chemistry #science #hydrogen #gas #elements #fire #chemical #industury #color
Your channel is honestly the first one of all the channels out there that I'm seriously considering supporting on Patreon. The value of your videos is just immense, packed with quality information and exciting visuals. Easily one of the best aspiring chemistry channels there is right now.
Thank you so much, it really means a lot. I always when people want to help fund my work, but I find comments like this every bit as meaningful. I do worry sometimes (in particular with this video) that I'm trying going a bit too far in the complex science of it all and so its fantastic to hear that not only is that not an issue, but actually genuinely appreciated.
Happy to have you along!
@@integral_chemistry Me personally, I love the science. I'm currently in the second year of my chemical lab assistant apprenticeship where I learn a ton of this stuff as well and seeing it applied when you fully understand the mechanism is just great
What I enjoy most about this channel is that you explain the chemistry and even sometimes the physics behind the reactions.
See what is so great about hearing that is I often worry I'm going too far in the explanations that I assume people either won't care about, or worse be actively bored by. Love hearing you appreciate that aspect of my videos :)
@@integral_chemistry those that are bored or uninterested can skip those minutes, those that are interested would skip the entire video if you didn't have those sections..
@@integral_chemistry i don’t know half the words sometimes, but hot damn I’m enthralled every time. (Often just repeating or pausing to read and attempt to understand best I can what’s going on) 😂
I never had a formal chemistry class, so much of the language and symbology I do know comes from nitty gritty detailed descriptions such as yours. Thank you.
At 0:36 I thought "mmm, a nice project to make with the pack of moth balls I have". But after seeing the amount of work I decided to leave them untouched. I can't wait to see the next videos, the copper chromite reaction is beautiful.
This man is criminally underrated.
Ouh because...meth ??
@@SayaialahBeliauBecause of the quality of his videos coupled with frequent upload time. He has only, 50k subs. That is not little but he deserves a lot more.
One prep of b-naphthol states 70% yield with mp 122 C. The purification includes recryst from weak HCl since such compounds are prone to turning into 'black death' upon any contact with bases. Overall well done, thank you! I like and appreciate the calmness and effort you put into your content
Damn definitely wish I'd come across that paper before starting, probably could have saved myself a lot of headache (and yield) if I'd known to avoid alkali around the final product. Did like 2 more recrystallizations I didn't even show here, nightmare stuff. Oh and thanks! Glad you enjoyed it regardless :)
was showing my lab professor [who used to be an organic chemist] some of my homework from another chem teacher relating to making phenol, he explained the thing with the precursors not being acidic enough and it went in one ear and out the other, but now i know for sure
i'd really love to see an NMR spectrum of your product, seems like this project would be perfect for a simple 60MHz NMR analysis. if you have a couple thousand dollars laying around you should get the NMReady 60-e Benchtop NMR. it'd certainly make you one of the most professional chemistry youtubers having access to his own NMR machine lol.
I do so desperately want an NMR and a UV-Vis. I do promise you that if the day ever comes that this channel inexplicably takes off or I get a ton of people engaged in patreon the very first thing I'll be buying are those two instruments.
I'd definitely go back and run every organic compound I've ever made, definitely a dream of mine when it comes to this channel and such.
@integral_chemistry keep collecting my patreon money, and you'll afford it eventually
@@Samonie67 I just tried to price check the 60e-NMR but apparently you have to request a quote, which is a bad omen on the cost lol. Thanks as always for the help, I have actually been setting aside my patreon fund for something like this.. Think I'm up to $1400 so definitely some progress.
@integral_chemistry yea your best bet is actually eBay or even any second hand business websites. I've had the pleasure of installing a 2nd hand machine at our university and it's quite literally plug and play. An undergraduate could figure it out
+1 for Nebula. I think you’d go down well over there.
Go for nebula! It's a great platform, and I watch a lot of my favorite youtubers on there. One incentive people commonly use is releasing videos early on nebula, another being "nebula only" (though, in this case, it could be "videos for Patreon and/or nebula") videos.
I would definitely watch your videos on Nebula, if that was an option
I really enjoy watching this show and have some (somewhat rambling) thoughts... and an analogy: I have an intuitive grasp of cooking food, so given some arbitrary ingredients, I can often make something tasty that is inspired by things I have enjoyed. My wife is not a risk-taker, and she always goes by a predefined recipe, usually with excellent results. Early on, I'd hoped that by watching these great chemistry videos, I would get an intuitive feel for the chemistry that I could extrapolate to various situations as with cooking, but now, I'm not so sure that will ever happen for me. Still, it's great to have been given so many recipes, so thank you for that.
Thank you for watching, and I think that is a fantastic analogy! I used the same one when I started, and I've found it very much to be the case. I suspect why it might not be the case for you as much watching chemistry rather than doing it is simply because so much of the process gets cut. This initial footage was over 3 hours, and that's only the footage what I did right. Mistakes and all the trial and error generally get cut which is where most of the learning happen as with cooking.
I do want to start including more of the mistakes and trial/error, but a lot of it is so tedious I might instead dedicate a whole video to stuff like that.
In any case, thanks for the ramble!
@@integral_chemistry I actually second this. I've used my chemistry skills in cooking with excellent results.
I think it's about the mindset, the way of thinking about the problem of mixing compounds to get to a goal. And this works in chemistry as well as cooking.
Also I've become neither a cook nor a chemist, but a computer programmer; which ironically is about an entirely different way of thinking about tasks/problems to arrive at a solution.
Thank you for the insane amount of work you put in to make these informative pure chemistry videos!
It's my pleasure, I'm truly happy you guys really appreciate what I do. It's very encouraging to me these days
Looking forward to the new projects you have coming up. It's a shame to see CZcams effect so many great channels like this one because of strict yet unclear policies and guidelines. Especially when the content is clearly educational. I think its a good move keeping the energetics exclusive to Patreon.
CZcams is anti-knowledge a lot of times.
@@filipealarza9079 absolutely. This is why all my favorite channels are going to other platforms.
Glad to hear you like the idea and are looking forward to those videos! I am genuinely excited to release some of them. As for CZcams I find it absurd how little support they give their small and mid-sized creators. Even NurdRage who is definitely in the top 0.001% of creators here has the same issues. I do wish they would hire staff to handle this stuff instead of relying so heavily on AI, and I know for a fact they can afford it.
They do provide how much money they make from our videos, I make about 10% of what my videos earn and so at this point they have made well over $110,000 from my uploads. Feel that's enough to deserve being able to at least speak to a human being.
If Nebula works for you, that’s a great idea! No Patreon app on Apple TV.
Huh that is definitely a big consideration I hadn't thought of. Thanks for the info!
Cool video! Now I know what I was saving those mothballs for!
Same lol I bought them like a year ago for no reason except "huh, a pure chemical. I could probably use this."
Awesome. I appreciate the thoroughness and ambition of your work dude
Props for the tenacity.
Right? I think a lot of folks would have just bailed at the yellow oil phase. The perseverance paid off.
Glad some people out there appreciate how annoying that was lol
I realized that you do chemistry out of the same type of white bowls I eat out of, I need to step up my game.
Lol tbh I also use that same brand in the kitchen, they're good bowls 😅
@@integral_chemistry no kidding, I dropped on to the ground from overhead cabinet level and it bounced twice and was fine
I was thinking that when I saw the bowl. Pyrex or Corell?
Love this channel never stop
Thank you so much :) I certainly hope to keep it up
now we just need a way to turn mothballs into 2 naphtaldehyde!
really interesting video!!
Pyridine is the vilest substance I've ever inadvertently smelled.
Try sulfur chlorides...
It's weird I have definitely smelled "worse" chemicals (like sulfur chlorides) but pyridine is unique in that smelling it gives me a primal gag/vomit reflex where it feels like every cell in my body knows I shouldn't be smelling it
Let’s see some bipyridine/phenanthroline complexes too
I was honestly thinking about it, love to hear there's some interest!
I have some napthalene mothballs in my chemical storage cabinet. Despite being sealed you can smell it from a couple feet away.
Naphthalene has got to be one of my absolute least favorite smells 😅 it penetrates everything and hangs around for ages. It's weird in this process the sulfonic acid still had the smell but since the stuff isn't volatile it was very toned down. The 2-naphthol had more of a phenolic smell to it
Ah, a dear memory of highschool. Smells like artificial cherry flavor
9:59 Really? I love the smell of SO2 and SO3!
LMAO I truly cannot relate 😅 SO3 is not the safest to smell, but I will say SO2 can be nice but only when it's coming from fireworks
Keep it up bro🫡
Thanks man! Feel I've been doing nothing but inorganic crap lately and this video really reminded me how much more I enjoy organic synth
(Sure you can relate lol)
Just wondering besides searching it up is there a way to determine if a compound is thermodynamically favorable or kinetically favorable? Like maybe considering the functional groups of the starting molecule or something.
mmm, tar chemistry
Did you do a melting point or paper chromatography to test purity? I am curious as to the final ratio of alpha to beta to dual substitution.
I did do a melting point, and I actually got some TLC Plates in recently to give the chromatography a shot. Thinking I'll do a whole video just on TLC/MP analysis of all the organics I've made
From glass thermometer stirring to steel digital thermometer stirring, Lol (I would probably do the same though as you don't have that many options)
Btw, is this the first time the "fumehood" running in closed state?
@integral_chemistry Btw I sent you a DM in Discord.
I'll check it out, been getting behind on replying to people lately, got a bunch of family stuff lately.
And yeah I admit I'm the worst about thermometer stirring, been trying to avoid it so people don't call me out as much in the comments but this time given the intensity of the reaction conditions I genuinely didn't know what else to use lol.
And technically the "fume hood" doesn't open/close. I have an upper pane of plexiglass that is mounted in place and covers probably 60% of the opening. On the bottom I have another pane that hinges shut and I only really use that if something started reacting out of control (which thankfully hasn't happened yet).
The reason you can see the pane in this video is because I had to film from a really high angle to see inside of the can and so the fixed pane was in the way.
@@integral_chemistry No worries bro, take your time.
The steel thermometer stirring isn't that bad to be honest, just funny, and if it broke it won't cause anything dangerous. The other things that I can think of is maybe use a steel chopstick or fork, since they should still function the same way in that regards.
Hehe oleum for my bungholeum
hehehe
Nice, I was precisely wondering how to attach hydroxyl groups to aromatics! Any chance a similar process could be used to add the missing -OH group to benzoic acid in order to convert it to salicylic acid? Or would the benzoic acid just uselessly decarboxylate under these harsh conditions? or would the hydroxyl attach to the wrong place?
I'm glad you liked it! To answer your question, I unfortunately think it would be a bit of both. The Thermodynamically and kinetically favorable property of that sulfonation would likely be the meta-isomer, and strong hydroxide does have a tendency to decarboxylate..
@@integral_chemistry ok too bad, but I didn't have very high hopes to start with anyways, thank you :)
Any explanation for why the sodium salt is less soluble? That's very counterintuitive
Hm yeah I hadn't thought of it. I'll look into it a bit more but I'd assume it's similar to how sodium chloride is less soluble than hydrochloric acid. Both really soluble for sure but free acids in my experience tend to be more soluble than salts. Again could be wrong but I'll check
Maybe the case for strong acids, but free acid forms of weak acids can be quite insoluble. A classic example would be EDTA, which is almost totally insoluble as the free acid but has high solubility as the sodium salt.
@@nerd1000ify That is definitely true.. It mostly has to do with the exact weak acid in question. Ethanoic acid for example dissolves quite readily in water, mostly because it is small and polar. EDTA does not dissolve well because it is bulky and not particularly polar so the covalent nature of the hydrogen bonding in the carboxyl groups prevent good dissociation. However this really only applies to carboxylic acids. Sulfonic acids are actually very strong acids, an example would be p-toluenesulfonic acid which is a very strong organic acid, and actually one of very few strong acids that is a solid at room temp. Sulfonate salts are generally always less soluble than the free acid in my experience.
bet the lab smelt... old
Not very many moths though.
😂
I kinda like the smell, but when it's strong it's overwhelming.
It certainly did lol. Luckily the sulfonic acid salt isn't volatile so it really only smelled at the beginning.
more mouse bites
❤❤❤
If you could make quinacridonequinone you'd be a godsend.
I keep failing this and I refuse to pay $765 for 10 grams
Weirdly enough I've been looking into that one for months. I've got an idea worked out, but it's a pretty rough process lol. If you have a strong background in chem it should be manageable but I certainly understand the price tag given the difficulty
@@integral_chemistry My chemistry background is watching chemistry youtubers and having organic chemists in the same room as me at my job so i can ask them questions when I need to but they are organic chemists so talking to them is like talking to a mold colony.
But even they wont help with this one and its driving me nuts.
All I want to do is make a discontinued pigment for personal use.
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Nitration (nitric acid) → Reduction to amine (sodium dithionite) → diazonium salt (sodium nitrite) → naphtol (boiling water) ???
Yeah I don't see any reason that wouldn't work. One thing though is you wouldn't be able to ramp the temp up during the nitration, otherwise it would just attach a second nitro group somewhere else. As a result the final product would primarily be the kinetically-favored 1-naphthol which is also super useful.
Do you have an idea how to separate 2-naphtol from 1-naphtol? I didn’t check anything so this question might be stupid. Also, unfortunately, naphthalene mothballs have been outlawed in Europe due to carcinogenicity suspicions.
Oh and yeah, I experienced with alkaline fusion to make catechol from p-toluenesulphonic acid. It works quite well, but the timing must be quite precise (also I did it in a nickel crucible put at the bottom of my heating mantle, it’s easier for stirring).
no nile red? xd
10000x better than chemdelic
Lol I appreciate the compliment but I gotta say he's done some really cool stuff, super great guy too 😄
The more YT censors the more boring and lame the publisher gets. It’s not a platform if they’re going to censor… wish there were fines for infringing on a nations legal rights their publishing in…. Maybe then a competitor could actually rise up ans be like YT once was…
I've always heard youtube isn't profitable, like Google isn't either, that's why they are doing it to make more ad friendly content ,virtual signaling to all the big companies. Plus Google search is shit now. Like youtube search is shit. On both platforms you get so much click bait unrelated content it's Insufferable. I don't Google search anymore to learn new topics. it's Chatgpt now, he's my new buddy.