Pyridine Synthesis

Guest · Sat May 21, 2005 2:42 pm

Pyridine is an essential compound required in the hobbyiest chemnical arsenal.

There is a synth that is very elusive, here is the ref'
Stoehr, J. pr.. 43, 153. t fur Chemie, 1871, 1:17. ject, the study of the constitution

If anymember can access this, we might be a step closer to a new route.

There are about 6 or 7 synthesis I am aware of,
But This particular one, Glycerine + Ammonia Sulfate, looks good,

I have also seen a few synth that use h2SO4 as well,

IndoleAmine · Dreamreader Deluxe

Pyridine is the worst thing I ever experienced, smell-wise...
(just wanted to mention it)

No wait - some tetrabutyl-something-mercaptan thingie I once had to handle was far worse, although handled in a glove box.. Shocked

Pyridine is still nasty.

Guest · Sun May 22, 2005 4:43 pm

Found it!<

another reference, looks like phyloxy had the same question

left · Mon May 23, 2005 2:24 am

Has anyone tracked down the J.prakt.chem. article?

yaya · Tue May 24, 2005 5:23 am

Is this what you’re looking for?

“
Synthetische Pyridinbasen der -Reihe
Journal für Praktische Chemie
Volume 43, Issue 1, Date: 14 January 1891, Pages: 153-156
C. Stoehr
“
“Pyridine can be easily made into Piperonyl, piperidine”
Oh yea?…..can you elaborate some?

thanks

hahas · Tue May 24, 2005 7:47 am

that one doesn't seem to say much about production from glycerol and ammonium salts.

Guest · Tue May 24, 2005 11:56 am

yaya,

do you have the whole article?

I think that is the right one, it should have something to do with glycerine or its chemical name.

syn

yaya · Thu May 26, 2005 4:47 am

“Pyridine can be easily made into Piperonyl, piperidine”

Don’t you mean that Piperonyl, piperidine can be made WITH pyridine, not from pyridine?

secret_squirrel · Thu May 26, 2005 8:13 am

yaya- Piperidine is made by the catalytic hydrogenation of pyridine, evidently.

Re: Pyradine from glycerine etc
I think this is exciting. Maybe this reaction could be scaled up to allow serious quantities of safrole to be synthed OTC. Glycerine is a waste product in the production of biodiesel. Ammonium phosphate is a common and inexpensive agricultural chemical. Put them together in an old modified keg and distill off sweet, sweet pyridine. Maybe it could be distilled right into a hermetically sealed reaction flask destined for the microwave pyradine reaction (see rhodium). This might alleviate the smell. Just some wild and crazy ideas to get people hyped on this. I'm excited.

nubee · Master Archiver

i found this:

http://www.tkk.fi/Yksikot/Orgaaninen/Opetus/moderni_synteettinen/luennot/Heterocycles1.pdf

over at:

http://www.chemicalforums.com/index.php

using:

www.google.com

discusse's pyridine synthesis among oher things... perphaps someone who knows a bit more about the topic could have a look... Wink

Guest · Thu May 26, 2005 1:03 pm

Good Find nubee,

Pyridine has many great uses, in all fields of hobbyiest chemistry,

Pyridine can be made by the decarboxylation of nicotinic acid and nicotinamide, at around 300c, with plain water,

Nicotinic Acid is Niacin, Yes, Vitamin B3
30g of Niacin costs around 6US or 8AUD, 3$ EU etc

Niacin by default does not contain nicotinic acid, only the prescrition stuff does, but who cares, when it is just as convenient to have the nicotinamide, which is the what is actually inside Niacin ( Vitamin B3)

From a few hours,well about 20 now, I get this creepy feeling that pyridine can be made by glycerol(glycerine, 1,2,3 propanediol)

If we can get that document translated, then we might be able to figure out the mechanism behind the glycerine + ammonia sulfate?---->pyridine

Here is the patent for the decarboxylation of Vitamin B3
JP56059756

http://l2.espacenet.com/espacenet/viewer?PN=JP56059756&CY=gb&LG=en&DB=EPD

I believe there might be some very fancy cyclization techniques to form phenyethlamine skeletons easily, Building the nitropropene routes via ring closure rather than ring additon, I think I saw the use of nicotinic aldehyde, somewhere,

Syn

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IndoleAmine · Dreamreader Deluxe

Guest · Fri May 27, 2005 7:09 am

Sorry, a typo on my behalf,

Piperine, can be turned into pyridine, and piperonyl,

What I should of said,

Pyridine is essential in the manufacture of many compounds,

Whoops!

But more imporantly, this discussion is on the maufacture of pyridine in the laboratory, which seems to have eluded alot of hobbyiest chemist,

Megolamania, from rogue science almost got the goods from Niacin, or nicotinamide, but has since stopped experimenting.

As lugh said sometime back at the hive, why try to decarboxylate te 3-postition, of pyridinecarboxylic acid(nicotinic acid) when you can easily build a picoline structure from glycerine and a sulfate, to form arcolein, which when added to ammonia at high temp, changes into picilone in good yield, and then demethylate.

Did lugh think that picoline was a pyridinecarboxylic acid, or was he saying that the methyl group at the 2 position of picoline is just as easy to demethylate as the carboxylate,

I searched and came up with alot of different opinions, and was unable to find such a demethylation technique, but that is not to say tat it doesn't exist,

Till now the most reliable way to obtain pyridine is to dry distill nictonamide(vitamin B3 with soda lime(casutic and Cao)).

This should be fine for small amounts of pyridine,
When large amounts are needed maybee the glycerin + sulfate---->picoline
would be the best option.

Syn

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