Author Topic: Cat de-wormer to piperonal  (Read 1645 times)

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AMINATOR

  • Guest
Cat de-wormer to piperonal
« on: October 30, 2001, 04:29:00 AM »
Cat de-worming tablets contain piperine and piperic acid (some contain piperidine...check contents). most of us are aware that piperine and piperic acid are the for-runners to piperonal.....for those not aware:

2. Reflux piperine in KOH+ethanol under reduced pressure until
dryness. Suspend the residue in water, heat and then acidify with
HCl. Collect the yellow precipitate of piperic acid.
                               
   O   ___                                   O   ___
  / \ / _ \            OH                   / \ / _ \     
 <   < (_) >--\//\//\ /   +  KMnO4 --->    <   < (_) >--\  /
  \ / \___/         ||                      \ / \___/    \/
   O                 O                       O           ||
                                                         O
                 
3. Piperic acid is oxidised with potassium permanganate (or some
other oxidizer) to yeild piperonyl....

Actually you end up with piperonyl, piperonylic acid and/or
piperonyl acetone in varying quantities.

the piperonal or Methylenedioxy-benzaldehyde is the treated with nitroethane and the nitroalkane reduced with LiAlaH to produce MDA.

Rhodium

  • Guest
Re: Cat de-wormer to piperonal
« Reply #1 on: October 30, 2001, 04:41:00 AM »
Permanganate is too strong according to

https://www.thevespiary.org/rhodium/Rhodium/chemistry/aldehyde.txt

- dichromate is the preferred oxidizing agent.

"The oxidation of isosafrole to piperonal by potassium permanganate under tested reaction conditions was far too vigorous, and the main product was piperonylic acid, whereas sodium dichromate and sulphuric acid afforded a 70% yield of piperonal, which was increased to 80% and 86.5% by the use of Dispersol and sulphanilic acid respectively as dispersing agents."

About Piperine:

http://www.bioperine.com/Manual/Content.htm

(with references)

PrimoPyro

  • Guest
Re: Cat de-wormer to piperonal
« Reply #2 on: October 30, 2001, 04:49:00 AM »
Dichromate may be out of reach for some bees, like me. KMnO4 on the other hand is easy to buy and make. So I wonder, Mr. Rhodium, or anyone who gets here first and knows the answer:

Since we know Piperic acid + KMnO4 __> MD-Ph-COOH

Could you then just make the calcium salt and react with calcium formate to yield the aldehyde (piperonal) a la halfapints method for benzaldehyde?

                                                 PrimoPyro

How does one win a race when the finish line runs faster than you?  :(

Rhodium

  • Guest
Re: Cat de-wormer to piperonal
« Reply #3 on: October 30, 2001, 05:01:00 AM »
Sodium Dichromate preparation:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/potassium.dichromate.html



But yes, if the method works for benzoic acid, it should for piperonylic acid.

terbium

  • Guest
Re: Cat de-wormer to piperonal
« Reply #4 on: October 30, 2001, 08:19:00 AM »
Cat de-worming tablets contain piperine and piperic acid (some contain piperidine...check contents).
All of the ones that I have seen contained piperazine. I have never seen any that contained piperine or piperidine.

AMINATOR

  • Guest
Re: Cat de-wormer to piperonal
« Reply #5 on: October 30, 2001, 05:22:00 PM »
hmmm....you may be correct, I was out shopping one day and I'm positive the box said piperine...but tiz possible that my memory or vision had failed me. I will check it out.

foxy2

  • Guest
Re: Cat de-wormer to piperonal
« Reply #6 on: October 30, 2001, 06:51:00 PM »
NOPE, They most definatly are PIPERAZINE.  The liquid ones are 250mgs/5 mL in a 120mL bootle($3.50) which is not bad if ya want to play with piperazines for cheap.

Do Your Part To Win The War

Aurelius

  • Guest
Re: Cat de-wormer to piperonal
« Reply #7 on: October 31, 2001, 02:59:00 AM »
poultry de-wormer- same thing.  piperazine (BZP- not that aurelius suggests making it)

AMINATOR

  • Guest
Re: Cat de-wormer to piperonal
« Reply #8 on: October 31, 2001, 08:10:00 AM »
I see....well, chemical free 'Critter ridder' contains piperine, gravel and misclaneous plant fragments. should be 'dirt cheap'....pun intended.


hmmm.... is piperonyl butoxide of any use??

Rhodium

  • Guest
Re: Cat de-wormer to piperonal
« Reply #9 on: October 31, 2001, 05:08:00 PM »
Oh, so now piperine is not a chemical?  :P

Piperonyl butoxide is of no use.

AMINATOR

  • Guest
Re: Cat de-wormer to piperonal
« Reply #10 on: October 31, 2001, 08:29:00 PM »
maybe if they convince enough people (DEA,FDA) we could by truck loads of piperine for while. ;D

uemura

  • Guest
Re: Cat de-wormer to piperonal
« Reply #11 on: February 24, 2002, 04:00:00 PM »
Refering to

Post 230250

(AMINATOR: "Cat de-wormer to piperonal", Chemistry Discourse)
: Piperic acid is oxidised with potassium permanganate (or some other oxidizer) to yeild piperonyl....

and to

Post 230272

(Rhodium: "Re: Cat de-wormer to piperonal", Chemistry Discourse)
: But yes, if the method works for benzoic acid, it should for piperonylic acid. (i.e. the K2CrO7 oxidation)

Uemura found in the original article from Fittig and Mielch Ann. Vol 25, 1869 the following remarks:

Reaction of piperic acid and chrom acid: Into a ice-cold solution of 20g K2CrO7 in 120ml 25% H2SO4 2g of the kalium salt of the piperic acid are added. There was immediately generation of CO2. .... The water steamed destillate was found to be pure water without any residue.

They go on with an analysis of the decomposition products and make a conclusion in the end:

This result is very surprising. Only a few complex organic compounds may be burned down completely to water and CO2 in a cold diluted K2CrO7 solution.

They also found, that the K2CrO7/H2SO4 oxidation destroys completly the piperonylic acid!

Uemura wants this to add to all the stories and attempts on the black pepper route. Obviously in this case you have to use KMnO4 as the oxidiser, not any dichromate.

Carpe Diem

terbium

  • Guest
Re: Cat de-wormer to piperonal
« Reply #12 on: February 24, 2002, 08:16:00 PM »
They go on with an analysis of the decomposition products and make a conclusion in the end:

This result is very surprising. Only a few complex organic compounds may be burned down completely to water and CO2 in a cold diluted K2CrO7 solution.

That is an odd and interesting result.

Did you find a library that has those old volumes of Annalen der Chemie? A company I once worked for had them in their library.

Rhodium

  • Guest
Re: Cat de-wormer to piperonal
« Reply #13 on: February 24, 2002, 08:36:00 PM »

uemura

  • Guest
Re: Cat de-wormer to piperonal
« Reply #14 on: February 25, 2002, 09:09:00 AM »
Hi terbium!

That is an odd and interesting result.



Yes, indeed. Uemura was collected infos and write-ups on oxidative cleavage of double bonds from his collected papers, when he touched the mentioned article to check the ratios/concentrations for the KMnO4 piperidin->piperonal oxidation when he found few pages before the section above.

Uemura preferred (public) library is specialised on the history of science. So they have almost all german journals, sometimes up to their first issue (*). Unfortunately they run out of money to continue after 1970+ for many. They are also 'low' on foreign journals.

(*) Thats way Uemura comes up always with these old German papers :)


Carpe Diem

Antoncho

  • Guest
Re: Cat de-wormer to piperonal
« Reply #15 on: February 25, 2002, 09:51:00 AM »
Adorable, Uemura. Will pass it on to a collegue of mine who's currently working on the project.

Antoncho