Doug's Lab - 2016-01-01
In this video, I prepare pyridine by decarboxylating niacin. Patreon page: https://www.patreon.com/DougsLab
As a chemical lab technician, these videos are awesome. Keep it up!
I'm amazed by how much effort it takes to pop off that CO2 molecule
Nature can do it pretty easy, but with quite sophisticated enzyme molecules.
Great, great work !!! Keep going man!
whoa, i really appreciate you explaining the reaction and all the steps of the setup! great vid!
I can't stop watching your videos!
Nice synthesis! :)
Nice one, keep it up
Could you explain the mechanism in this reaction?
Decarboxylation Reaction using Copper Carbonate or Copper chromate/chromite as a catalyst
I bet it smells like roses. :D
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.
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.
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!
It's vitamin B3 not B6.
+Drunk Bastard
Darn, I swear I meant to say that! Thank you. I have corrected the video with an annotation.
+Drunk Bastard Vitamin B6 is also based on pyridine so I can understand how he made that mistake.
Am i the only one who's not a chemist watching these videos?!
+crysata computer programmer here, want to setup a hobby lab though :)
I learning slowly. .its like trying to teach a small rock;)
@Ash j same
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. 😀
nicotine from nicotinic acid?
I'm re-watching this video as I fell asleep yesterday when I was halfway through >.<
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.
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.
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.
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!
The reaction won't proceed at the temperature of boiling pyridine. It needs to be about 250ºC.
Awesome video
11:18 You're left with Doug's slab in the RBF after Doug's lab?
LOL my room smells of pyridine very often.
you could achieve similar results by pyrolizing an alkali niacinate in presence of soda lime.
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.
zodd0001 I doubt that the yields will be that high. I think this method is very efficient
Besides the Calcium method is very clumbsy giving a lot of tar and ruins the glasware. Thats why this Video is so cool.
You do know that you are producing chromyl chloride in this reaction also, right?? That stuff is particularly nasty dude!
+noilex
Chromyl chloride hydrolyzes immediately on contact with water to form chlorochromic acid. Also, I made chromyl chloride - check it out! https://www.youtube.com/watch?v=legoRGAXNP8
+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?
@jared garden
hah.. That's a very good question indeed! I don't know why I wrrote that??? wtf
First.
+Curtis Dorris (AtrumBlood) Cool dude. That kind of thing gets old.
+Classical Liberal , It's an addiction. I think I need professional help. Plus I have an unhealthy infatuation with that heating mantle ;)
Doug can I use pyridine to isomerize Delta 8 THC into Delta 9? any ideas?
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.
I think that in this case the high temperature could damage the plastic clip.
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
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??
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.
'Lab Ninja'.. HAHA 😂
Humble organic chemist by day; Stealthy Guardian of Peace & Justice by night!
A freak mishap in the lab bestowed inhuman powers upon this modest alchemist!
Your comic debut awaits.. 😂
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
It may be possible but you need reasonably pure nicotine to do it.
I have access to fairly pure nicotine from an e-liquid supplier, would that be pure enough to try?
Niacin was first prepared by oxidation of nicotine with nitric acid. Nicotine also oxidizes under UV light to produce nicotine oxide, methylamine, and niacin.
No drunken New Years Eve chaos, but it smells like it nonetheless.
do you think the copperchromite kat. also works do decarboxilate benzoicacid ?
scott pro No benzoic acid can be directly decarboxylated under heating of 300-500C but be careful because benzene is highly flammable and toxic. not to mention a known carcinogen that can cause leukemia in chronic exposure
@Dylan Mcvicker 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.
If you don't know how to calculate theoretical yield, you shouldn't be doing chemistry.
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)
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?
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
Doesn’t your fume hood have a sash?
Why didn't you reflux until the decarboxylation was complete and then distill?
thats what i was thinking
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.
I found niacin capsules at dollar general today . $1 per bottle of 45 caps. Let's see my result
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...?????
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
Oscar Poll It can be bought online, if you still need it.
Just make your own
Would it not be a better idea to reflux the mixture firsthand to decarboxylate the ring and only then distill off the pyridine? That way you'd avoid the sublimation problem.
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.
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.
+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.
+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.
What could be pyridine used for?
Hmm... So our bodies cannot convert one into the other? What is the precursor for pyrimidine then? (I'm just being curious.)
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.
So how do they make those terminating nucleotides marked with luminescent dyes for use in DNA sequencing or synthesis? I guess there's no organism or natural enzyme which would produce such "broken" nucleotides, so they have to be made in a lab somehow?
Sci Twi they're very clever. :-) look it up! It doesn't start with lab synthesis though. Usually they introduce artificial starting materials and let nature do its work or do clever grafting after the fact. Nothing so basic as nucleosynthesis.
For example, it can be used as a scavenger molecule to remove methyl groups from aryl methyl ethers. It is used widely in pharmaceutical industry for syntheses. Great solvent.
Dániel Kalocsai - 2016-03-22
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!