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Magpie
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Thanks smuv. It really was easy once you have the catalyst.
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ordenblitz
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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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| 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.
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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. 
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ordenblitz
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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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unome2
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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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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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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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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.
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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AndersHoveland
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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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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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Tempus_Edax_Rerum
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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.
The Reality Principle does love to disabuse us of our whims.
... Hououin Kyoma
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SunriseSunset
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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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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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| 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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NZniceguy
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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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wildfyr
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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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NZniceguy
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| 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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nimgoldman
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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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| 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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S.C. Wack
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Hydrolysis of niacinamide is not difficult with HCl or NaOH.
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NZniceguy
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Any chance you could give some details on that please?
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nimgoldman
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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.
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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:
make solution of nicotinamide in a beaker (say 50%)
add enough acid to make it strongly acidic (say pH 1.0-2.0)
heat and stir on hotplate to almost boiling
nicotinic acid will precipitate, filter, wash with cold water (to remove nicotinamide) and return filtrate to the hotplate
continue boiling off water and filtering until no more precipitation is observed
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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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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S.C. Wack
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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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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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