Pyridine from Niacin

[@kalolord]

The thing I like about your channel is that you actually make pretty big amounts of your products. Not like "oh here's 5 grams of *some reagent*, add 10ml of *another reagent etc.". Pretty cool!

[@oobermate]

As a chemical lab technician, these videos are awesome. Keep it up!

[@kevinbyrne4538]

Congratulations on your successful synthesis of pyridine. In many parts of the world, the arrival of the new year is traditionally greeted with an organic synthesis. Seriously, however, thanks for taking the time and trouble to prepare these videos.

[@Huskrrrr]

Well done! You just saved me some serious money on lab pyridine!

[@Bronner33]

I found it works well to control the heating mantle with a PID controller connected to a temperature probe placed in the still head. And a light dimmer in series with the mantle also helps to tune the setup. I was able to leave this unattended overnight after I got things set. The temperature in the flask gets high enough to push some pyridine over but then backs off before much sublimation of the niacin occurs.

[@lifeatpaddyspub]

whoa, i really appreciate you explaining the reaction and all the steps of the setup! great vid!

[@plante1999]

Here is a tip: Use a reflux apparatus at first, and the pyridine will serve as a solvent and add all the niacin you want, reflux for a bit, and then distill.

[@stamasd8500]

I use a small straight adapter between the flask and the distillation head that serves as a poor man's reflux/fractionation column. It's a straight 15cm tube with 24/29 joints. Works pretty well in this setting.

[@kevincolwell2115]

I'm not a chemist by any stretch of the imagination, but I've been watching tons of chemistry videos for their entertainment value, and this was the exact thought I had! REFLUX IT!

[@jpdemer5]

The reaction won't proceed at the temperature of boiling pyridine. It needs to be about 250ºC.

[@vector8310]

Every single one of your videos teaches me something and inspire me to do chemistry. Now all I need is the cash for equipment. 😅

[@bromisovalum8417]

Pyridine is a handy base to have around. For one as a common tertiary amine and Lewis base , to make PCC (pyridinium chlorochromate),and Collin's reagent (pyr.CrO3), both very selective oxidation agents, milder than CrO3 itself. Electroreduction at a lead cathode to obtain piperidine would be cool too provided you can do it in a closed system. The last thing you want to do is have an open cell with flowerpot diaphragm through electrode gas evolution spray a fine mist containing pyridine in the air.

[@astroglide420]

I can't stop watching your videos!

[@bromisovalum8417]

Cool, wish I still had my lab equipment. I had to move to an apartment, no more garage or attic I could do experiments in like in the old days. So no opportunity to mess around with stinky pyridine, lol imagine, my apartement would smell like the pits of hell. Bet the neighbour would be real pleased.

[@minipac2]

I'm re-watching this video as I fell asleep yesterday when I was halfway through >.

[@michaelhenwood2493]

Ur awesome keep it up I love learning

[@petkotzvetkov6528]

Great, great work !!! Keep going man!

[@DutchPhlogiston]

Cool, I like your video's very much. I noticed you clamped the distillation head and rely on a clip to connect the roundbottom flask. I was taught to clamp the neck of the roundbottom flask in a setup like this. The weight of the distillation head should rest on the round bottom flask. This ensures a good seal of the ground glass joint. A clamp around the neck of distillation head is optional, and if used should be very loose, just to prevent sideways motion.

[@pietrotettamanti7239]

I think that in this case the high temperature could damage the plastic clip.

[@pietrotettamanti7239]

I usually don't clip the round bottom flask to the distilling head because of this (I burnt one some time ago), but you can use a metal clip if you have it available

[@RaExpIn]

Nice synthesis! :)

[@buckstarchaser2376]

No drunken New Years Eve chaos, but it smells like it nonetheless.

[@michael3263]

It always surprises me to hear you talk about the smell of pyridine when there are so many more amines out there that stink so much worse. 😀

[@petevenuti7355]

I ordered what I was told was niacin, and what I got was inositol hexanicotinate. That's also all I can get at my local drug store. Before I order from someone else, is there a way to separate the inositol? Is what I got an ester or a salt? What could inositol be used for? It looks useful... How do I make thf?

[@smitetheunholy6179]

It's vitamin B3 not B6.

[@DougsLab]

+Drunk Bastard Darn, I swear I meant to say that! Thank you. I have corrected the video with an annotation.

[@goyabee3200]

+Drunk Bastard Vitamin B6 is also based on pyridine so I can understand how he made that mistake.

[@psycronizer]

well,..... arse ! fek ! girls !.....

[@zodd0001]

you could achieve similar results by pyrolizing an alkali niacinate in presence of soda lime.

[@amosz5726]

Sciencemadness forum users have used calcium oxide as a base for this but the copper chromite catalyst appears to give the best and cleanest yields.

[@antejl7925]

Mix the tar waste with ethanol and a little toulene it makes an excellent wood creosote.

[@Piocoto123]

Could you explain the mechanism in this reaction?

[@angelonapolitano888]

How to do calculate the amount of a catalyst needed in a reaction? For example, here you used 2 g copper chromite, which in this reaction is the catalyst, per mole of niacin. How did you get that number? I would love to hear your answer!

[@rogerdotlee]

So I *DO* remember my days of working the docks where one of our clients shipped pyradine in bulk. I seem to recall it smelled like Satan's jock strap. When I found out that pyradine was an 'aromatic hydrocarbon', the phrase made perfect sense.

[@JDeffenb]

Awesome video

[@Robocop-qe7le]

I bet it smells like roses. :D

[@aaronmcguire9730]

What is the yield after purification say with naOh etc. Distillation etc? The video on another video using copper carbonate gave relatively low yields. How pure is this product.

[@lm5050]

Nice one, keep it up

[@erikshaw1511]

Hey Doug,I tried to ask you a few question's before in the comments of your ketene lamp video, you didn't answer those questions but if you could at least answer one question on the same topic, I would greatly appreciate it. What gauge nichrome wire did you use for the filament??

[@Sparky78739]

Can you turn the pyridine into pyridine hydrochloride?

[@libalj]

Why didn't you reflux until the decarboxylation was complete and then distill?

[@middleschoolprecipitate3743]

thats what i was thinking

[@UC235]

Doesn't work for the same reason you can't reflux salicylic acid and turn it into phenol. The stillpot containing molten niacin is far hotter than the boiling point of pyridine. There's a temperature gradient up to the stillhead. If you try to reflux, the stillpot drops in temperature to the boiling point of pyridine and decarboxylation slows to a uselessly slow rate.

[@tetrazolelover]

LOL my room smells of pyridine very often.

[@DarrenDIY]

nicotine from nicotinic acid?

[@Berghiker]

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

[@196Stefan2]

Yes, this will work out, but probably at a far higher temperature than 200 °C. Sulphuric acid forms an azeotrope with water with 98% H2SO4 with a boiling point of 338 °C! I dont know what exactly will happen at 200 °C, but I assume only a partial removal of water. Dealing with such high temperatures with glass-ware always poses a serious risk. Concentrated H2SO4 at room temperature is no fun, but the acid at 338 °C is a horror.

[@Berghiker]

@@196Stefan2 I did do this years ago and it worked. I heated 500ml of 68% H2SO4 at 500 deg C with my expensive lab grade hotplate and I got 94.5% in the end after about 5 hours. It was a risk but I did this on the balcony outside.

[@196Stefan2]

@@Berghiker A liquid at ambient pressure, heated in an open vessel, actually can never get hotter than it's boiling point, in case of H2SO4 338 °C (Water 100 °C, Ethanol 78°C, Acetone 56 °C etc.). The boiling point may raise, the higher the concentration of the acid gets, but 500 °C no way!

[@Berghiker]

@@196Stefan2 Ok. I didn't have a thermometer that time to measure it.

[@JonathanR1994]

I found niacin capsules at dollar general today . $1 per bottle of 45 caps. Let's see my result

[@alllove1754]

Jonathan Rendon and the result is..... drum roll...... one yr later, d...r...u...m... r..o..l..l is slowed way down... and crickets... and silence.. and your results are...?????

[@crysata704]

Am i the only one who's not a chemist watching these videos?!

[@astroglide420]

+crysata computer programmer here, want to setup a hobby lab though :)

[@ashj_2088]

I learning slowly. .its like trying to teach a small rock;)

[@ChannelMath]

@@ashj_2088 same

[@crabcrab2024]

Doesn’t your fume hood have a sash?

[@br2openup100]

Actually, there are 2 types of organic carbon-oxygen bonds: R--C=O (carbonyl) and O II R---C---O---R (carboxyl)

[@ryanhenry8290]

You've had that same magnetic stirring mantle for a couple years now huh? I've been looking for a good quality one. How is it still holding up? Which brand is it?

[@alllove1754]

Believe it or not stay away from Teflon because if it overheats you end up with a compound that I only know of the acronym PFOA. quartz glass is what you really want to get for high temperature work quartz is it the Crystal they use that it's expensive but it is worth every penny in the end

[@jonnathanschillinger9021]

You say in the beginning that niacin is a hydrolysis product of nicotine 0:15 , so is it possible to convert nicotine to niacin? I haven't been able to find anything on doing this

[@douro20]

It may be possible but you need reasonably pure nicotine to do it.

[@jonnathanschillinger9021]

I have access to fairly pure nicotine from an e-liquid supplier, would that be pure enough to try?

[@amosz5726]

Niacin was first prepared by oxidation of nicotine with nitric acid. Nicotine also oxidizes under UV light to produce nicotine oxide, methylamine, and niacin.

[@davidnahmad9405]

Doug can I use pyridine to isomerize Delta 8 THC into Delta 9? any ideas?

[@7kilos947]

Never heard of this one

[@scottpro6591]

do you think the copperchromite kat. also works do decarboxilate benzoicacid ?

[@Felixkeeg]

@@dylanmcvicker8330 That's a really bad idea, there's no way you have a cooler at home that can reliably cool vapors of 300-500°C down to below 80°C. Probably produces a variety of polycyclic hydrocarbons in the flask and gas phase at those temperatures as well.

[@oscarpoll2463]

Hello, Is there any way that i could buy some pyridine off you for a science project. I would only need to buy around 100-500ml! Thanks Oscar

[@AwsomeVids83]

Oscar Poll It can be bought online, if you still need it.

[@nitrousman8882]

I think you meant B3, didn’t you?

[@chimerahitman]

Doug, I like watching your videos but they lack purpose. Let me explain. I don't know any chemistry, but the videos are interesting and would like to know the purpose uses of it in the future or maybe what I can be used for.

[@Bsblob]

+Stefano RR I think that in the videos he assumes you have a decent foundation of synthetic chemistry. Also many of the compounds he is making are quite versatile. Pyridine for instance has a very wide variety of applications for synthetic organic chemistry. If all else fails, wikipedia has plenty of info on all the compounds he has made.

[@matta8508]

+Stefano RR You'd like Nile Red.... he's gone throw a ton of synthesis with the (very noble) objective of making poop essence... And with a lot of molecular sieves in between for good measure.

[@xelionizer]

You do know that you are producing chromyl chloride in this reaction also, right?? That stuff is particularly nasty dude!

[@DougsLab]

+noilex Chromyl chloride hydrolyzes immediately on contact with water to form chlorochromic acid. Also, I made chromyl chloride - check it out! kzbin.info/www/bejne/opbKoIV9dr2Bhpo

[@jaredgarden2455]

+noilex how the hell would he be producing any chromyl chloride in this reaction, the niacin he bought is food grade and is thus pure and would have no chlorides present what so ever, the copper chromite was prepared by heating ammonium copper chromate up to its decomposition temp of 350*C and the ammonium copper chromate was subsequently prepared by reacting ammonium chromate with copper sulfate. So where the hell would the chloride come from?

[@xelionizer]

 jared garden hah.. That's a very good question indeed! I don't know why I wrrote that??? wtf

[@scitwi9164]

What could be pyridine used for?

[@Grak70]

Pyridine is a good solvent for other reactions. The HCl salt is also a catalyst for a variety of reactions. Stinks like hell though. I hated using it when I worked in a lab.

[@scitwi9164]

Grak70 Oh... I was hoping that it can be used to make pyrimidine and then some nucleotides for DNA synthesis ;J

[@Grak70]

Sci Twi Nah, they're totally different heterocycles. Can't make one from the other.

[@scitwi9164]

Hmm... So our bodies cannot convert one into the other? What is the precursor for pyrimidine then? (I'm just being curious.)

[@Grak70]

Sci Twi synthesis of nucleotide precursors is incredibly complicated in biological systems. Just google "biological synthesis of pyrimidine" and you can find sources. There are generally two routes: de novo synthesis from CO2 and amines, and scavenge synthesis from bio-waste products. Both routes are enzyme catalyzed and light years beyond the ability of any organic chemist.

[@atrumblood]

First.

[@JDeffenb]

+Curtis Dorris (AtrumBlood) Cool dude. That kind of thing gets old.

[@atrumblood]

+Classical Liberal , It's an addiction. I think I need professional help. Plus I have an unhealthy infatuation with that heating mantle ;)

[@ThePaintballgun]

If you don't know how to calculate theoretical yield, you shouldn't be doing chemistry.

[@alllove1754]

Even your name implies trolling... smh. And wtf do u do, deb? (No not Doug, video maker, but guy above me in comments, initials are deb)

[@novatech7451]

Pyridine+ codeine = heroin

[@farqdude]

It's dickheads like you that spoil it for others. If you've ever manufactured homebake heroin before, I doubt it, then you'd know that your dicky little formula is wrong anyway. Who are you trying to impress mate, certainly not me. By not saying anything I would think Doug is the least impressed. Show some respect & keep that shit to yourself! Raising red flags is stupid.