How to make Pyridine from Vitamin B3

Niacin (Vitamin B3) is decarboxylated into pyridine (which fuccing reeks) using a copper chromite catalyst. First we make the copper chromite catalyst from waste chromic acid waste I somehow generated in the past, then we do the decarboxylation distillation, chemically clean up the pyridine and then re-distil. Nothing too complicated, and I don't throw up, so it was a win for all, especially people who like doing chemistry in the middle of the night.
The Sciencemadness post we are following is here: www.sciencemadness.org/talk/vi...
It is the post near the bottom, labelled "Improved Preparation of Pyridine" by UnintentionalChaos, a true credit to him, fantastic writeup.

[@georgiahalliday8998]

Good vid. I only skipped to the part with myself in it but I’d still give it a 10.

[@ExtractionsAndIre]

u r a 10

[@kjpmi]

Aww this guy ^

[@obviouslytwo4u]

Now this is chemistry of love

[@nigeldepledge3790]

I don't think I've ever read "lightly blowtorch" mentioned in any of my chemistry textbooks. I did wonder how you were going to deal with the pyridine and its unique aroma. It's possibly the fourth-worst-smelling substance I've had to deal with.

[@chemistryofquestionablequa6252]

Like menthol fish...

[@n0tthemessiah]

I worked in an orgo lab for a couple of years as an undergrad and had to use pyridine almost daily. The worst part of the smell is that it felt like I was smelling it the entire rest of the day, long after cleaning up and leaving the lab, even after I showered and changed clothes it felt like I'd catch whiffs of phantom pyridine every few minutes. Drove me mad.

[@ruffusgoodman4137]

@@n0tthemessiah Maybe the substance may adhere to your clothes, like greasy smells of grills on a barb/meat house

[@alans7358]

Came for the chemistry, stayed for the music ...and the chemistry too i guess

[@DrewskisBrews]

I love keeping my hex' chromium in a wine bottle, too. I find the liquor cabinet to be a great place to store it.

[@haraldhimmel5687]

Ah 2016.. a fine vintage!

[@TeslaFactory]

Serve it to your pregnant wife to try produce an Xmen of your very own! 😅😂

[@siberianstuntman3344]

I prefer the pond in front of Erin brockovich's house

[@rubywest5166]

Really? I’d be extremely concerned by that, especially when one looks at the colour. Surely a port bottle would be more appropriate?

[@DrewskisBrews]

@@rubywest5166 i use a Galliano bottle now

[@spiderdude2099]

I find that pyridines smell can best be described as “floral, greasy, and like rotting fish oil” like, there’s an undertone that’s ALMOST perfumed and pleasant but like you dumped febreeze over rotting fish that you were deep frying

[@chemistryofquestionablequa6252]

I'd say it's like menthol rotting fish

[@MeneltirFalmaro]

Soooo... pyridine smells like: victory; anchovies, death, olives and bad. Makes total sense.

[@bromisovalum8417]

And it lingers too. Made a mistake once smelling pyridine straight from the bottle. It's revolting and it lingers in your nose for half a day.

[@chemistryofquestionablequa6252]

Smells kinda like menthol fish.

[@spiderdude2099]

I find the best description to be: “Like you sprayed febreeze on a rotting fish your were deep frying”

[@rubywest5166]

When I had to use it once I felt it was a “mouldy crabstick” smell

[@Humbulla93]

@@bromisovalum8417 that´s a smell you´ll never forget, worked with it twice and absolutely hated it, had to counter that smell with inhaling ether but the relieve was very short

[@rogerdotlee]

Ah yes. Pyridine. Back in my misspent yoof, I worked for a trucking company that had two clients (American Scientific and VWR Scientific). You always knew when one of them had a shipment of Pyridine. Even in a sealed bottle, you needed to give that stuff a wide berth. The phrases we liked to use was 'insupportable stench'.

[@ExtractionsAndIre]

Stench is a great word, seems very appropriate for it somehow. Disgusting. Yet labs were buying it as you say, so it must be pretty useful!

[@Rhodanide]

"That doesn't make any sense but I'll just do it" Hey, that sounds like me!

[@ExtractionsAndIre]

Rhodanide in my head I always think "Jesus Christ I have to edit this rubbish"

[@Rhodanide]

Extractions&Ire It's almost like a lost art, rearranging garbage into a coherent video. That's in my case, your stuff isn't garbo m8

[@abbott2426]

Well even with the loss of efficiency, that still was a neat little project- perhaps the pyridine will come in handy later! Certainly interesting to see how a useful substance can be created from readily available materials, too.

[@ExtractionsAndIre]

I'm hoping it does come in handy, but yeah it has been a project i've always wanted to do. Pyridine is hardly a mundane chemical, but you can make it quite easily, which is just magical honestly

[@TiernanWilkinson]

I love your videos on extracting chemicals from basically household materials; fascinating how the things we use every day forms the building blocks of even refined chemicals and that. Keep it up!

[@trashcompactorYT]

I was gonna watch Nile's video on this but when I saw you did it as well I clicked instantly. Love Nile, but your videos are insanely entertaining

[@chriseffpunkt4333]

I like this channel so much because just as ElectroBOOM he basically shows what can go wrong but still does the thing. Remebered to not overheat stuff several times because of him goofing up ! thanks for that!

[@Vinni-2K]

i watch him too

[@piranha031091]

11:17 : "I love the smell of Pyridine in the evening. Smells like victory!" What do you plan to use it for?

[@TheRolemodel1337]

i think it smells like tomato noodle sauce before adding the spices :p

[@ExtractionsAndIre]

wow that does not sound like a good sauce

[@ExtractionsAndIre]

The plan is perhaps use it during the chlorination of isobutene. I know you're a firm believer in the sodium acetate to mop up the HCl, but looking at the speed of the overchlorination during the gas phase reaction, I feel that a suspension of solid isn't going to be good enough to scavange the HCl. Perhaps pyridine is too nucleophillic, but so far I think its the only idea I could see working that also not heaps and heaps of effort to do

[@piranha031091]

Good to see you're not giving up on that one! ^^ And yeah, Pyridine sounds like a much better HCl scavenger than acetate. TheRolemodel1337 : WTF??? What kind of tomatoes do you use?

[@TheRolemodel1337]

The Sauce coming with this: www.miracoli.de/sortiment/pastagerichte/spaghetti-mit-tomatensauce-familienportion when i first smelled pyridine in the lab i instantly thought of the unprepared tomato sauce of Miracoli noodles :p the labassistent confirmed that it also reminds her of that particular sauce

[@mglmedchem8324]

Great video's, thanks. It's good to see someone showing realistic experiments with the challenges & small errors - rather than editing & cutting to perfect procedure and max yield in one vid; somewhat refreshing. Also, in Aus we can get B3 in most chemists now, sold as "Insolar", by Blackmores. It's not that cheep, but handy & good purity. Thanks for the videos!

[@blakecatlett1011]

Last year I was working on a project that required very precise silicon measurements, so no glassware! My PI found a huge bag of piss bottles just like those old ones of yours, and I did all of my work in said piss bottles. Lots of fun that

[@sethkunert6234]

Someone turn these into audiobooks. Like, backyard chemistry, but in a narrative fashion, with asmr quality background sounds of the ongoing experiment in each stage. Like the TV show "how its made", but also an autobiography by the reckless. Then again, "Off white coloration..."

[@jhyland87]

9:11 Probably easier to blow the bag up with some air _then_ mix the contents around. _Great_ video! I plan to try this as well. Thanks.

[@chemistryscuriosities]

Been waiting for this

[@danielgrantcoleman]

Awesome. You made the pyridine. Gotta hate that smell. Hope that means you are going to try again on the isobutylene. 👍.

[@ExtractionsAndIre]

Yeah that's the thought, hopefully it will save that project

[@danielgrantcoleman]

Gotta love grams keeping chem bottles for you. Haha. My whole family gives me bottles and coffee filters and distilled water ect ect. And they always ask me. Hey. I planned on throwing this “chemical/drug/whatever” away. Do you want it?

[@Cameron_the_Robot]

Today, I learned how to "lightly blowtorch" my solvents. What sublime!

[@dakane328]

in my lab we do like a 50 g scale synthesis step in pyridine and the workup is in a 4 L erlenmeyer in a tub of ice that can't fit in the fume hood so we have to do it on the floor and oooh boy those fumes are spicy

[@StreuB1]

You get a +10,000 for listening to Stardust while doing chem. Fuckin aye mate, lovely.

[@richardwebb5317]

Adverts when I was a kid: Cornflakes, I kept hearing "fortified with niacin and firemen"

[@chemplayer2855]

Nice work!

[@ExtractionsAndIre]

Fantastic to see you back in comment form mate

[@chrisfromnz3038]

I have tried the copper carbonate method along with the copper chromite method a few times and can confirm the yield is much better using the chromite......what I would like to know is, can the copper chromite be recycled somehow? Could you simply wash the left over residue with distilled water or such and reuse it for the next run? Perhaps with a little extra added?

[@ScienceWithJames]

What do you have planned with the new pyridine; pyridinium chlorochromate?

[@psycronizer]

well done bro, I've got plans to do this too, got the Niacin but haven't looked at any methods yet, there's bound to be a few...just from general org. chem. knowledge I know that heat alone can decarboxylate a few compounds

[@alexlong2377]

The compounds that'll decarboxylate the quickest with just heat would be ones with a carbonyl on the beta carbon of a carboxylic acid, or something else to help grab the hydrogen from the COOH group. Those suckers will pop right off! Niacin would be tougher to do in that manner, which is why there's a need for a catalyst in this reaction. Good luck!

[@psycronizer]

@@alexlong2377 yeah, it is also often attempted by using the metal salts of the acid, like Calcium or Barium, better leaving group

[@papaversomniferum5247]

I love these videos

[@markdwyer314]

Can ammonium dichromate be used instead of chromate? Cheers, cool vid

[@valfodr]

Is the first part a similar process to making ammoniacal silver nitrate?

[@wilbertbirdner1303]

"...it's like bad.." *keeps smelling it*

[@trogdo]

Man, a old wine bottle full of hexavalent chromium waste is a pretty cursed object to keep around

[@AngDavies]

Isn't that green the colour of chromium 3? Incomplete oxidation/a reducing agent somewhere?

[@paulgrosse7631]

Next, you need to add methanol, iodine and sulphur dioxide to make your own Karl Fischer reagent, then you can measure low levels of water in things.

[@pbpbpbpbpbpbpbpbpb]

Sweet! (or, to stay true to reality, cool but eww!) What music did you use at 14:50?

[@blackirish781]

You could use it to make pyridine hcl to demethylate codeine to morphine...

[@science_and_anonymous]

I MISS CHEMPLAYER!!! $ :(

[@caraudiosales3572]

I like the basification

[@psycronizer]

might have been an idea to set up the condenser for a reflux for a while THEN switch it over to distillation....

[@Sleepy_zzzzz]

8:18 Uh, no, that makes total sense. I'd of started with less than a half of the niacin for the mixing then built up. It's easier to pay more attention to less material.

[@StreuB1]

3:50 STARDUST!!!!!! YESSSSS!!!!!

[@trevorday7923]

Marry that woman immediately, we science nerds very rarely find a woman who is that understanding and supportive ❤️

[@griffin5226]

I have so much copper carbonate. I know what I'm doing this weekend

[@MichaelClark-uw7ex]

OK where does the Hydrogen from the hydroxyl group go when you decarboxylate, if the only byproduct is CO2? It would seem there is an extra Proton left over that has to go somewhere. Does it bind with some of the Oxygen to make water? Then what happens to the leftover Carbon? There is not enough Oxygen to make both. Or is there some weird chemistry going on with the catalyst making Copper hydroxide or Chromium hydroxide and Carbon monoxide?

[@ExtractionsAndIre]

It's not obvious, but it goes onto the carbon in the pyridine ring, because you leave a vacant space when the carboxylate group leaves

[@MichaelClark-uw7ex]

@@ExtractionsAndIre OK thanks, I didn't see that. That's a relief, having free monatomic Hydrogen floating around can end quite badly.

[@AhmetOzdemir-om3bj]

Now make piperidine from pyridine and make methylphenidate from piperidine.

[@psycronizer]

no..he'll probably just bubble some HCl gas into it, to make Pyridine Hydrochloride to use on demethylating codeine...then with his morphine he'll either reduce it with Pd and hydrogen in alcohol to hydromorphone or he'll acetylate it to Heroin...you know....like everybody just naturally does...

[@Finnnicus]

Why isn’t refluxing pyridine/niacin over copper chromite the standard here? If you’re going to remove the pyridine from the mixture in a second distillation anyway, you may as well push the reaction as far as you can in the first.

[@ExtractionsAndIre]

Excellent question. I didn't really consider it as I was more or less following a procedure that gave such high yields that it didn't seem necessary. And I suppose that's the real reason, if the yields are high and you'd have to do a second distillation after the reflux anyway, why bother. On a larger scale, yes. Although there would be issues with your reflux condenser clogging. On a deeper level, there may be some issue about keeping the pyridine in contact with the hot copper catalyst. For example, when NileRed uses a copper carbonate catalyst, he gets ~40% yield. Where does the 60% yield go? He doesn't boil over 60% of the nicain, nor does he fail to collect stuff. This is purely speculation, but there does seem to be something else going on

[@Metallica4Life92]

one of the few chemicals I actually fear and respect, as to just respect.

[@WilliamFord972]

Can this be done with a weaker catalyst than copper chromite?

[@ExtractionsAndIre]

You can just chuck copper carbonate in, you do lose some yield though

[@danielmclatchie5229]

lit

[@andrewmodell5889]

I would try dry ice and actitone bath then smoke a beer.......pump air into it pop the top or just add dry ice

[@sazxcdewq123]

11:07 THICC

[@mr.m0lam0la]

"so over here we have a soup can..."

[@billsmathers7787]

3:47 Is that Stardust I hear?

[@ExtractionsAndIre]

its that daft punk song, is it called Stardust? Was on the radio and thought it was cool so I just didn't mute the audio like I normally would

[@billsmathers7787]

Stardust was a collaborative project formed by half of Daft Punk before Daft Punk formed. The song is titled "Music Sounds Better With You".

[@MikeRvirtualmike]

"that looks fuckin mint as!" hahaha

[@PowerCrafter123]

10:54 Me working with Pyridine and Phenylacetyl chloride for the first time this semester

[@benburn5]

So there’s pyridine in NutriGrain

[@unlockeduk]

i got quite good yields with copper carbonate and it does smell fishy

[@freehat2722]

When it's a success it's "I", when you fuck up it becomes "we". I'm kindly joking around :P

[@TheZabbiemaster]

You might want to watch out a bit with that stuff. I've heard that long exposure will kill your reproductive system

[@wilbertbirdner1303]

where can i get some?

[@elephystry]

Birth control

[@tmfan3888]

2:35 Cr2O4 2-? 5:30 Cr is reduced but nothing is oxidized?

[@BeastM140i]

Dude settle lol

[@enzyme20056]

I was too lazy to make the pyridine so I just bought some. But the odour is foul or like fishy garbage. How on earth can you use it without the product smelling like fishy garbage. It smells toxic.

[@ExtractionsAndIre]

if more people used it in the manufacture of drugs, it would solve the drug crisis overnight

[@enzyme20056]

Extractions&Ire I think organic active pro-molecules sounds nicer than “drug” and “crisis”. I just know that there are algorithms and AI”s that scan just about the whole internet for trigger words. What governments and companion AI”s have effective set up are modern equivalents of book burnings and petty excommunications. Like the first video of yours I ever saw is just gone. Why? I don’t know. As a consequence of not understanding science people seem to distrust scientists and ignore or make diminutive assessments of their work as dangerous or unnatural .I always introduce myself as a natural products chemist in conversation, people respond more favourably to that than anything else; even tho there is no such thing as unnatural chemistry.

[@connorhoyle2926]

Has chromic acid, doesn't have vinegar...

[@richlong2270]

Is that aphex twin I can hear, track name ???

[@ExtractionsAndIre]

Excellent ear mate. All the backing tracks for my channel come from Aphex Twin's Soundcloud dump that he did, oh a little while back. Because he has never officially laid claim to the tracks, they're virtually free use, which is great, because so much music will get you a copyright flag on youtube these days. And there's so many great tracks. This particular one is: kzbin.info/www/bejne/Y3Xbn4iKrq6eoKc Vintage Aphex. So recognisable. Especially the top line that comes in at about 1:20. So good.

[@richlong2270]

Awesome tom thanks for the reply I will check that out 😀Also I was wondering if you have or are going to create something like chemplayer has (bitchute) I think. to upload all of your old content. I would love to be able to watch those videos again.

[@patrickbo2045]

@@ExtractionsAndIre I KNEW that's aphex, love it!

[@Valdagast]

How to make the the shed smell like fish.

[@feelinghealingfrequences7179]

pyro pyri?

[@scottwest5704]

Ooh dude

[@DanielSMatthews]

So you turned niacin into eww not niacin?

[@ExtractionsAndIre]

yeah it loses quite a lot of health benefits when you remove that CO2 group...

[@californium-2526]

@@ExtractionsAndIre And becomes toxic! (pyridine is toxic)

[@sidjoosin6549]

they name this thing vitamin b3, niacin or nicotinic acid depends how angry they at moment and their's hormon level. true story

[@chumblywarner3776]

Impro cork ring

[@sholbaman1463]

Why not just use sodium hydroxide?

[@ExtractionsAndIre]

And do it exactly the same as the sodium benzoate production? Good question. Firstly you'd have to convert it to the sodium salt, which has a much higher melting point. And you'd have to run it in a metal container as you'd have to rely on the sodium hydroxide to melt, which would eat through your glass flask. But would the chemistry actually work? Even if it had lower yields? That's a good question, I'm not sure

[@AussieChemist]

Umm different background music

[@ExtractionsAndIre]

you don't like it?

[@AussieChemist]

Extractions&Ire nay just not used to it I guess

[@Rhodanide]

Aussie Chemist Blasphemy

[@ExtractionsAndIre]

Aussie Chemist this guy has some of the most forward thinking progressive electronic music.... Most of which was recorded in the 90s, like this track probably was lol

[@mrfantasticguy6385]

Sounds a bit like chemplayer's music, RIP

[@GodlikeIridium]

I hate pyridine... smells damn bad and makes you impotent.... But every damn method for acetylations use pyridine as solvent.

[@mehmoodhassan5355]

make videos with English subtitles please ....

[@jackeldridge1319]

Dude the amount of times I've seen you use sulfuric acid, toluine and ammonia: you are definitely getting watched by the feds. Like it's to the point where I understand why you use benzene instead now, like nobody wants benzene coke. Benzene in durries is understandable, but benzene coke? Nahhhhh son

[@3er24t4g1]

You should make chlorobenzene from phenol

[@ExtractionsAndIre]

Why chlorobenzene?

[@3er24t4g1]

Chlorobenzene can be reduced to aniline and used in many reactions, for example coupling reactions, and is dangerous for the amateur to produce at home as it requires benzene. On the other hand phenol is easy to make from aspirin using only a few dollars of glassware. Well most amateurs would avoid handling benzene they are comfortable with phenol and aspirin.

[@DrakkarCalethiel]

Good morning everyone! Really hate the smell of pyridine, just dreadful!

[@ExtractionsAndIre]

It really is just awful isn't it. I new that coming into the project, but I was still surprised at just the kind of bad it was... it wasn't worse than I thought, i knew it would be awful, but like your brain struggles to go 'hey that's a bad smell its coming from the chemical' it just goes 'wow ok you are sick now lol'

[@ExtractionsAndIre]

also Good morning!

[@DrakkarCalethiel]

Extractions&Ire Thanks! The first time I made pyridine with the cuco3 method I thought, nah it won't smell that bad. Yeah, 20 minutes in and I turned my big fan on to blow that dreadful nauseating smell away. Without the fan It was just horrible! Granted I did it on a large scale. The good thing is that I'll probably never have to do it again. I still have 110 grams left. My poor neighbours, I still feel bad for them xD

[@ExtractionsAndIre]

>110g left Ok yeah that's fairly large scale, i'm impressed

[@DrakkarCalethiel]

Extractions&Ire I used all the niacin I had left. I thought if I make quite a bit I'll never have to synthesise it again.

[@nielsandersen6164]

Like... acidic acid. LOL

[@richardwebb5317]

Unfortunately given prices at the moment, my supermarket only sells the basic version

[@robmckennie4203]

Maths pop quiz what's half of 70

[@immewhou1755]

Anchovies? Its not good Anchovies its bad...👏🙌🧑‍🏫👨‍🏫

[@Nagria2112]

"force people to smell it" you know it makes sexually ipotent right?

[@Exotic_Chem_Lab]

First 😄

[@sammiller5114]

METH

[@keithcookman2918]

Pyridine stinks...........