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Author: Subject: Pyridine synthesis/extraction
Magpie
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[*] posted on 14-11-2008 at 18:51


Thanks smuv. It really was easy once you have the catalyst.
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ordenblitz
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[*] posted on 14-11-2008 at 21:39


Jarynth,
I did not do any more work on the catalyst recovery as I did not have the time. If I were to do any more work in this area it would be on other more common copper compounds to see what else might work better. But since pyridine is of no particular use to me, simple curiosity may not be enough for me to continue.

Magpie,
Did you get any final numbers after distillation for yield? Very interesting project making the catalyst don't you think? I was most amused by the burning of the copper barium ammonium chromate. Also, you keep such a clean lab, I feel ashamed.

[Edited on 15-11-2008 by ordenblitz]
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Magpie
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[*] posted on 15-11-2008 at 08:26


Quote:

Did you get any final numbers after distillation for yield? Very interesting project making the catalyst don't you think? I was most amused by the burning of the copper barium ammonium chromate. Also, you keep such a clean lab, I feel ashamed.


No, I just transferred the pyridine directly to its storage bottle. For my intended use the quantity is more than adequate, and IMO the purity is likely already quite good.

Yes, making the catalyst was interesting. I burned the catalyst off in my muffle furnace so really wasn't able to watch it decomposing. I did expect to see brown NO2 vapors coming out the top of the door gap, but did not. Perhaps the nitrate decomposes to N2 instead.

Re: my lab: I have limited space so have to keep everything in its place. It also makes me feel like I have things under control. :o
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ordenblitz
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[*] posted on 15-11-2008 at 08:34


I would not have characterized any of the runs I did as producing anything near pure. If you evaporate a few drops of the distillate on a watch glass you will more then likely find a remaining tan/white colored residue.

[Edited on 15-11-2008 by ordenblitz]
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[*] posted on 24-5-2009 at 15:21


Here is another on the use of copper(II) nicotinate for the production of pyridine

"The Thermal Decomposition of Copper(II) Nicotinate and Isonicotinate" Thermochemica Acta, 138 (1989), 233-9

They form the salts from CuSO4 and the sodium nicotinate in solution, the formed Cu(II) nicotinate precipitates and is washed.

Lot easier, if it works, than making the copper chromite

[Edited on 24-5-2009 by no1uwant2no]
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elsolvital
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[*] posted on 1-5-2010 at 00:00
Easy pyridine from Niacin


Thanks for the posts here, I was able to make pyridine thanks to them. I made some copper chromite and used it to make pyridine. Then I tried just mixing niacin with aluminium oxide and it worked too. And then I found an even better way...

Just put the tablets whole and uncrushed in the flask and slowly distill them and you get pyridine. Too easy and it works as well as with copper chromite. I used these:

http://www.puritan.com/niacin-b-3-362/niacin-nicotinic-acid-...

Don't bother with catalysts, just distill the tablets whole!!!
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chief
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[*] posted on 1-5-2010 at 00:53


I can get the kg of Pepper at 6 EUR (white or black) ..; with the pyridine-content at 5-9 % (wikipedia) this would give 50-100 g of pyridine for 10 bucks of production-cost ...
==> Is the pyridine any useful ? Can it be sold to any people ?
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UnintentionalChaos
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[*] posted on 1-5-2010 at 01:43


Quote: Originally posted by chief  
I can get the kg of Pepper at 6 EUR (white or black) ..; with the pyridine-content at 5-9 % (wikipedia) this would give 50-100 g of pyridine for 10 bucks of production-cost ...
==> Is the pyridine any useful ? Can it be sold to any people ?


We're talking about pyridine, not piperine.




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AndersHoveland
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[*] posted on 26-5-2012 at 02:38


The trimer of acetaldehyde can be reacted with ammonium hydroxide and ammonium acetate at 230 °C to make 5-ethyl-2-methylpyridine in 50-53% yield.
Org. Synth. 1963, Coll. Vol. 4, 451-453
http://syntheticremarks.com/?p=147
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cal
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[*] posted on 4-8-2012 at 18:10
Link


Do you have a English version?

Quote: Originally posted by not_important  
The ZIP file appears to be broken, near the end of it in the central directory the "version made by" offset is bad, looks like the zip creator stuttered and had 0x1414 instead of 0x0014. What was used to create it?

As it is a DJVU file, zipping it saves little if any space. If the zip was needed to get the board software to take it, that's one thing and perhaps the board could be configured to accept .djvu files, otherwise it might be better not to zip single .djvu files.
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[*] posted on 22-1-2016 at 08:09
Price of Pyridine prepared from Nicotinic Acid


At an 84% yeild from Niacin and the copper chromite catalyst, I was able to produce just under 14L's from 25Kgs of Niacin. I bought 25Kgs for 400 USD from a health food store online. The cost of the catalyst which I prepared, only cost about 30 USD. So if you can buy ACS grade Pyridine cheaper than 430 USD for 14L's, please tell me who your chemical supplier is.



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SunriseSunset
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[*] posted on 31-1-2016 at 10:27


Youtube Video for Copper Chromite catalyst preparation

The same guy also shows how he made pyridine in another one of his videos. From niacin (nicotinic acid) and the copper cromite catalyst. The reason you want to see these videos is because he explains and shows a lot of useful techniques for the preparations! He works at a pretty fast pace and talks pretty quick too. I like his videos a lot

[Edited on 31-1-2016 by SunriseSunset]




Why do chemists call helium, curium and barium the medical elements?
because if you cant helium or curium, you barium! - Heimerdinger
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Magpie
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[*] posted on 31-1-2016 at 10:34


Quote: Originally posted by SunriseSunset  

The same guy ...


This is Praxichys, a member of this forum. He is now the prolific producer of a fine line of YouTube videos. ;)




The single most important condition for a successful synthesis is good mixing - Nicodem
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Herr Haber
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[*] posted on 31-1-2016 at 21:40


Quote: Originally posted by UnintentionalChaos  
Quote: Originally posted by chief  
I can get the kg of Pepper at 6 EUR (white or black) ..; with the pyridine-content at 5-9 % (wikipedia) this would give 50-100 g of pyridine for 10 bucks of production-cost ...
==> Is the pyridine any useful ? Can it be sold to any people ?


We're talking about pyridine, not piperine.


I could see a lot more uses for piperine than pyridine. A few bad ideas spring to mind ;)
Pyridine is a very seldom used solvent. I got 250ml 3-4 years ago and only used about 50ml so far (probably involved in the desctrction of some kind of EM.)

What I do know about Pyridine is that I store it in my toilet among other sensitive chemicals. I replaced the HDPE bottle with real Duran glassware and an PTFE cap. I can stil hear the gurgling noise *I'm about to vomit" from my GF that was passing by behind me even though I had an extractor on (and a gas mask!).
That's the solvent I like less because it's hard to describe the other without being "rude". I mean, it's a mix of sewers, rotting fish and lady parts that havent seen a shower for 15 days.
Even considering boiling point and vapor pressure I'm sure it stinks more even in summer.
And yeah, the toilet / cabinet for nasty chems has a window that's open all year long!

I was very interested in the synth above that went directly to hydrochloride for that reason.
There are alternatives but sometimes not and I know a couple of experiments I never did just because of the stench !
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[*] posted on 27-8-2018 at 20:15


I have been sent niacinamide instead of niacin....niacin is usually a powder when I have bought it before but this is crystals....now the billion dollar question is......will the niacinamide still decarboxylate to pyridine as niacin does?

Edit....damn I see it has an NH2 group instead of the OH group....is there a reasonable way to remove the amide to get pyridene?

[Edited on 28-8-2018 by NZniceguy]
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[*] posted on 28-8-2018 at 18:17


I think the trouble of getting the amide off is much more than just buying some niacin and waiting for it to arrive.
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[*] posted on 29-8-2018 at 05:11


Quote: Originally posted by wildfyr  
I think the trouble of getting the amide off is much more than just buying some niacin and waiting for it to arrive.

I think you are right....guess i'll just have to wait the two weeks.....the joys of living on the opposite side of the world to everybody else. :)
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[*] posted on 3-9-2018 at 21:00


I have prepared pyridine successfully by decarboxylation of niacin (vitamin B3) mixed with basic copper carbonate. It has been discussed here long time ago and the method works.

Copper chromite catalyst should give you better yields and you need much less.

It's certainly not the best, cheapest or highest yielding method but if you need little bit of pyridine (say up to 500 ml), it works great.

Purification of pyridine consists of drying it with NaOH/KOH (this also precipitates niacin as salt), filtering and distillation over more NaOH/KOH.

See Nile Red and Doug's Lab videos on YT. They show the process in detail.

My first time I made something like 60 ml of crude pyridine.
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NZniceguy
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[*] posted on 8-9-2018 at 06:41


Quote: Originally posted by nimgoldman  
I have prepared pyridine successfully by decarboxylation of niacin (vitamin B3) mixed with basic copper carbonate. It has been discussed here long time ago and the method works.

Copper chromite catalyst should give you better yields and you need much less.

It's certainly not the best, cheapest or highest yielding method but if you need little bit of pyridine (say up to 500 ml), it works great.

Purification of pyridine consists of drying it with NaOH/KOH (this also precipitates niacin as salt), filtering and distillation over more NaOH/KOH.

See Nile Red and Doug's Lab videos on YT. They show the process in detail.

My first time I made something like 60 ml of crude pyridine.


That is exactly what I usually do but this time i was sent NiacinAMIDE instead of Niacin so cant just decarboxylate.......I've had to reorder and wait 3 weeks for delivery due to me living on the wrong side of the world.
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[*] posted on 8-9-2018 at 09:01


Hydrolysis of niacinamide is not difficult with HCl or NaOH.



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NZniceguy
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[*] posted on 9-9-2018 at 19:43


Quote: Originally posted by S.C. Wack  
Hydrolysis of niacinamide is not difficult with HCl or NaOH.


Any chance you could give some details on that please?
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[*] posted on 9-9-2018 at 20:56


I see. I faced the same problem as I could get only NiacinAmide locally so had to order Niacin from abroad.

However, here an interesting article on the topic:

Using Niacinamide in an acidic formulation

Quote:
The conversion from Niacinamide to Niacin is called NON ENZYMATIC HYDROLYSIS. Basically that means splitting a molecule up to release water without using a biological enzyme to cleave the molecule. This type of hydrolysis reaction is quite common in organic chemistry.

...

The above study found that a 10% Niacinamide solution heated to around 89C and then taken to a pH of below 4.5 with a STRONG acid did start to hydrolyse and form Niacin and that this conversion was a first order reaction which basically means it went from Niacinamide to Niacin without turning into anything else first. The study found that between pH 4.5-6 very little of this crazy game of shape shifting occurred. In fact at pH 4.5 – 6 the half-life of the solution was found to be 1000 days which probably means that the average cosmetic formulator has little to worry about.


You're welcome.

The reaction gives off ammonia so you could tell the reaction proceeds by smell.

Removing the water should not be much of a problem since niacin has solubility of only 18 g/L and m.p. of 237 °C so hard boiling won't hurt it.

Nicotinamide has much higher solubility in water (500-1000 g/L depending on source) which is convenient.

So the procedure would be something like this:


  1. make solution of nicotinamide in a beaker (say 50%)
  2. add enough acid to make it strongly acidic (say pH 1.0-2.0)
  3. heat and stir on hotplate to almost boiling
  4. nicotinic acid will precipitate, filter, wash with cold water (to remove nicotinamide) and return filtrate to the hotplate
  5. continue boiling off water and filtering until no more precipitation is observed
  6. air dry or vacuum dry the collected nicotinic acid


[Edited on 10-9-2018 by nimgoldman]
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S.C. Wack
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[*] posted on 10-9-2018 at 02:52


I presume that after niacinamide is refluxed with conc. HCl for long enough, the HCl distilled off would leave niacin hydrochloride and ammonium chloride.



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[*] posted on 10-9-2018 at 13:49


AFAIK, at this point if water is added at the rate it's distilled, in time only niacin should remain.



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NZniceguy
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[*] posted on 11-9-2018 at 06:25


Thanks guys, I shalll give it a go whilst i wait for the next lot to arrive and will let you know how i get on.
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