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All 14 posts   Subject: new method of ephedrine production.   Please login to post   Down

 
    metalgirl
(Newbee)
11-09-04 17:03
No 540666
      new method of ephedrine production.     

This research project is being conducted in collaboration with the Victoria University of Technology.

Ephedrine is a major pharmaceutical compound used widely in cough mixtures, as a decongestant for respiratory allergies. It is currently manufactured by a process which involves the use of organic solvents which have the potential to affect the environment. The process is also expensive as it not only produces the desired molecule but also its mirror-image - subsequent to manufacture, these two molecules have to be separated which is a very difficult process.

The primary aim of this project was to devise an integrated, cost-effective system for the preparation of ephedrine using yeast in an environmentally friendly reaction media. This system may potentially have the following significant advantages:

 it would produce only the desired molecule, not its mirror-image
 it would eliminate many of the by-products produced in the conventional process
 it would replace the current organic solvents

A process has been developed which results in high yield of pure ephedrine in a supercritical carbon dioxide solvent system. Patent applications have been submitted to cover this invention, and Circadian is currently seeking partners to licence the technology.
 
 
 
 
    syschk
(Stranger)
11-09-04 17:23
No 540669
      link me     

URL?

shadow man keeps me company
 
 
 
 
    ChemoSabe
(Hive Addict)
11-09-04 17:29
No 540671
User Picture 
      Biosynth     

Sounds like this is the same or  procedure and method as in the biosynth over in serious chemistry? Post 199197 (Jacked: "Biosynth: Homebrewing Ephedrine", Serious Chemistry)

That posting came straight from Mobius Bandsaw who was the homebrewing forum moderator over at Adroid's now self sabotaged site that was quite similar to the hive.

I'll never forget his comment on when he borrowed some panty hose type stockings to use as filters for winemaking from a hippy girl that he knew. He claimed that they were ready to go for winemaking/fermenting as they already had a decent culture of candida yeast growing on them in the crotch area.

PS. Hey metalgirl, if possible can you give the web URL where you got this?

can't flush this
 
 
 
 
    cycosyince
(Hive Bee)
11-10-04 08:52
No 540790
      Hmmmmmmmmmm     

And they are seeking licensing and/or yadda yadda HERE? No disrespect to the hive, intentional or otherwise, but I have to wonder if there is a hidden agenda, or is this a bit of trolling by some really laid back folks at ol' VUT...wink

"HEY! I know where there would be hundreds of folks that would just LOVE to get on board for THIS STUFF!"
"Are we talking about..."
"I'm talking about folks who are REAL interested in this particular area of chemistry's latest technology!"
"Well go get 'em TIGER!"blush

It doesn't matter. I'll probably get run over anyway...
 
 
 
 
    ChemoSabe
(Hive Addict)
11-10-04 11:15
No 540802
User Picture 
      The URL     

Here's the link.

http://www.circadian.com.au/ephedrine.htm

An utterly astounding lack of information is there concernng this.

And as Organikum has said before on this same topic... (paraphrased) "there is an astounding lack of apparent interst from bees in this technique"

I agree with that sentiment.

As has also been said before, it most likely is true that not many will have an interst in making homebrewed, gakk-free ephedrine until the complete and utter disappearance of OTc 'phed' based products.

Necessity will be the mother of widespread use concerning this particular invention.

can't flush this
 
 
 
 
    Organikum
(Wonderful Personality)
11-10-04 14:08
No 540823
      Not really     


Necessity will be the mother of widespread use concerning this particular invention.


If you refer to "this particular invention" as the production of l-PAC in supercritical CO2, this will never get widespread, neither in industry nor in clandestine chemistry.
I you refer to the yeast mediated conversion of benzaldehyde to l-PAC, this is already the leading technology for ephedrine and pseudoephedrine production worldwide.

The point because this biosynthesis will never become widespread in meth-labs is plain that it affords some basic equipment and knowledge, at least the ability to do fractional distillations and a reductive alkylation.
Dont forget the biosynth doesnt yield ephedrine directly but l-phenylacetylcarbinol which has to be reductivly alkylated to ephedrine. This can be done and is done in industry without isolation/purification of l-PAC but using the raw extract from the fermentation broth (solvents to use in extraction are: ether, chloroform, benzene, toluene, xylene). There is no use in starting a biosynth without having everything needed for the reductive alkylation by hand, say HgCl2, Al-sheet, nitromethane (or methylamine).
The biosynthesis itself is fairly simple and yields between 15% if done sloppy and 50% if done right on the used benzaldehyde. It gets obvious that making benzaldehyde oneself is advantageous. And its not too hard to make it from toluene.
The biosyntesis setup can also be used for making beer and liquor, providing a nice cover for the stuff and the distillation gear and providing booze and beer. Homebrewing shops sell everything needed, in special nutrient salts and thiamine. Yeast is bakers yeast, the cheapest bakers yeast from the supermarket is ok, although you will want to grow it your own lateron for better yields.

It is perhaps interesting to mention that l-PAC can also be reductivly aminated to norephedrine, the starting compound for the famous and fairly simple trans-4-methylaminorex (4-MAR) synthesis as posted by Bandil.
The reductive amination step is harder here as it has to be done under pressure to get tolerable yields if ammonia and Al/Hg is used. The final step to 4-MAR is even easier than any ephedrine reduction as it employs potassium or sodiumcyanate (from urea and potash/sodium carbonate), is done in water and needs nothing whats watched or dangerous.

To tell it: This is nothing to start from the level of a RP/I or Birch cook and to be finished next week. Anyways, if one isnt able to get it going or looses interest, there is always left the gear for making moonshine so not all is lost laugh


Some links, (not complete!):
Al/Hg reductive amination
Post 539332 (abolt: "Hardware store flashing (Thick Al) & Nitromethane", Newbee Forum)
Post 534610 (bio: "Al/Hg Reductive amination under pressure results", Methods Discourse) whole thread
https://www.rhodium.ws/chemistry/alhg.osmium.html

Benzaldehyde
Post 208702 (Antoncho: "The easiest synth of benzaldehyde from toluene", Chemistry Discourse) whole thread
Post 519043 (Organikum: "Better method for the Sommelet", Stimulants)

Biosynthesis of l-PAC
Post 199197 (Jacked: "Biosynth: Homebrewing Ephedrine", Serious Chemistry) whole thread, also the linked posts. Lots of goodies, lots of noise, some nonsense.
I will probably post a new variation of the benzaldehyde to l-PAC biosynth in the next weeks as part of a norephedrine synthesis.



A word of advise:
When looking for example for a synthesis of benzaldehyde, dont jump on what sounds so very easy to you but check first what compounds are needed in the different synths and which of them are available to you. Starting from available compounds has advantages, trust me here smile
Then collect the writeups and keep in mind that the shortest ones which look so very easy at first sight are so short because some details were omitted, detail which the author either regards as common knowledge or which he does not know because he has never done it in reallife.
After having collected and read the posts, feel free to ask further questions in the "Newbee" forum. Link to the posts you refer to and ask your questions. Everybody who shows real interest this way was ever refused help AFAIK.


/ORG


I cant spell, I bad look, the only thing about me is I know how to cook......
 
 
 
 
    ChemoSabe
(Hive Addict)
11-11-04 22:09
No 541093
User Picture 
      Thanks Org     

I was hoping to lure you out to say something on the subject as in my book you're the most qualified on this particular topic.

I'm actually shocked at the degree to which you've spilled your own hard earned beans and valuable hints and clues here as I've never seen you bee so generous with the entire bee enclave on this esoteric subject.

But it's that giving time of year and I'm sure appreciative of your gift of consolidating this info into one easy to access post.

The home beer brewing angle is quite an awesome thing that can make an operation like this appear 100% legit.

Thanks again Org

can't flush this
 
 
 
 
    ayejay
11-11-04 23:10
      I agree
(Rated as: UTF PM Function)
    
 
 
 
    dwarfer
(esoteric)
11-12-04 23:00
No 541294
User Picture 
      Ah yes: But Orgy still has other gifts     

Rumor has it that Orgy has developed
a genus of yeast which has the genetic capacity
to not only stand microwave irradiation,
but thrive on it:

converting moleasses bottoms
to L-Pac up to 90%
before getting drunk and expiring:
and in 30 minutes or less per gallon.!!


No wonder Interpol wants him:
his knowledge would reduce Pseudo sales by 52.6%:
we're talking big money, friends.tongue

Wy, the minus minus precursors make make only
enough dextro product to keep you buying:
not enuff to get you high.

Orgy has had to reinforce
the Right hand side of his vats:
that’s the only way his trained  bugs
know how to turn:
the combined force of trillions at once
hitting the wall
has dented steel
and shattered glass.


Yes, Organicum likely will be a Moleasses Guru:

the rest of us, sated with Laevo MA,
will approach for instruction:
the only likely “continda”
will have a mean right cross
(Kolbe):

phenylalanine betters to the left,
coolplease..cool

Left, right, left, right:
up, down; in, out:

sounds like SEX to me:blush


but those yeast cells know better:
spore things!crazy


Gettum’, Orgy! laugh

dwarfer
 
 
 
 
    Organikum
(Wonderful Personality)
11-13-04 00:20
No 541304
      Would be nice, is not true     


Rumor has it that Orgy has developed
a genus of yeast which has the genetic capacity
to not only stand microwave irradiation,
but thrive on it:

converting moleasses bottoms
to L-Pac up to 90%
before getting drunk and expiring:
and in 30 minutes or less per gallon.!!



As told: This would be nice but isnt true. There is some information about yeast which is microwave irridated at low power giving elevated yields, but for sure not 90% and for sure not in 30 minutes.
Reaction time for the biosynthesis is 8 to 14 hours, plus some hours for a continous extraction (if one doesnt want to use VERY large amounts of solvent in the extraction. It allows also to use more water and to skip the acetaldehyde).

Dont get greedy Dwurflinger! wink

/ORG


......
 
 
 
 
    WizardX
(Wizard Master)
11-13-04 04:02
No 541324
User Picture 
      L-PAC
(Rated as: good read)
    

http://www.angelfire.com/scifi/WizardX/yeast/index.html





A collection of patents. http://www.angelfire.com/scifi/WizardX/yeast/yeast.zip
 
 
 
 
    WizardX
(Wizard Master)
11-13-04 04:53
No 541334
User Picture 
      Welsh Rearrangement.
(Rated as: good read)
    

Welsh Rearrangement.

Medline (PMID=7252804)

Sodium boro[3H]hydride reduction of dl-ephedrine gave [alpha-3H]-dl-ephedrine, and a Welsh rearrangement with acetic anhydride followed by deacetylation gave [alpha-3H]-dl-pseudoephedrine, which was used as a radioligand in radioimmunoassay procedures for direct plasma analyses.


L-Phenylacetylcarbinol (L-PAC): biosynthesis and industrial applications.
http://www.kluweronline.com/article.asp?PIPS=273980&PDF=1

L-Phenylacetylcarbinol (L-PAC), an important drug intermediate, can be produced by biotransformation of benzaldehyde, mainly by yeast cultures but also by Zymomonas mobilis. The biotransformation by free cells, immobilized cells, mutant organisms, purified pyruvate decarboxylase as well as the use of bioreactors, the downstream processing of L-PAC and the industrial applications have been reviewed.
 
 
 
 
    wareami
(Hive Addict)
11-13-04 11:43
No 541361
User Picture 
      Hmmmmm...     

I knew I stumbled into that biomass crap somewhere!laugh
The rush for alternate fuel sources seems to have borrowed some stepped UP attempts from the biochemistry lab in the direction toward the creation of biofuels. That was the first time I saw that "Zymomonas mobilis" term used.


  • An ethanol (E85) vehicle displaces 400 gal/yr of gasoline
  • Ethanol vehicles produce
35% less CO
42% less NO
43% less NMHc
39% less PM
79% less CO2
over life cycle
  • Zymomonas mobilis has
œ shorter fermentation time(300%-400% faster than yeast)
œ higher ethanol yield (92%-94% versus 88%-90% for yeast)
  • Converts sugar mixtures to ethanol with 90%-95% efficiency



Orgy? Have you been holding out on The Kidz?smile

Hey homey...while we got ya here...sourcing of pyruvate isn't as easy as it once was thought by Ibee.
Vigorous aquisition attempts haven't been employed yet, but casual window shopping has turned UP nadda!

Now if I didn't know any better, I'd see this Zymomonas mobilis as a more abundant, easier to aquire substance for treehugger types investigating ways to save the planet.
But what do I know?
If they can extract themselves off the floor and from their fits of hysteria long enough to finish reading this, Dwarfinger and Orgy may see my presense in a thread this complex as a "letting the cat outta `da bag" experience as this subject is too far left for Ibee's feeble mind and it's a radical shift from Ibee's normal routine of "Extracting camels threw the eye's of needles"laugh

The shift is in gear bees as what was propheseed about the opposition putting the smackdown on pills is upon us!

Onward HO!


I'm not totally useless! I can be used as a 'Bad' Example!laugh
 
 
 
 
    Organikum
(Wonderful Personality)
11-13-04 15:50
No 541383
      Not all this again, please!
(Rated as: excellent)
    

There is 1 (one) for our needs well suited patent on l-PAC production and this is Patent DD51651

It is in german, and here is a translation of important parts:

Method for the production of l-ephedrine

Prior art:
- Use of an acid resistant yeast. A aerated suspension of bakers yeast is exposed over 40 minutes to rising concentrations of 0,3% to 10% of a mixture of sulfuric and phosphoric acid in water. Then this yeast is allowed to ripen in a solution containing molasses. The yeast is separated and used as inoculate in the production of l-PAC.

- Use of simple bakers yeast and molasses with or without the addition of the usual nutrient salts. The addition of hydrogen acceptors is supposed to reduce byproducts. 31% to 35% yield.
Hydrogen acceptors are for example acetaldehyde, the addition of nutrient salts is told to LOWER yields (?)

- A nutrient solution containing 3,5% unrefined sugar, 6% molasses, 0,05% MgSO4.7H2O with a ph of 5,5 is used. Acetaldehyde (50% in water) is used as hydrogen acceptor in a ratio of 1 to 1 to benzaldehyde. Bakers yeast (saccharomyces cerevesiae) is used in the fermentation. Benzal and acetaldehydew are added in four portions of 0,2% of the volume of the fermentation broth over a time of 7 to 8 hours. Between the 3rd and 4th addition about 20% to 25% of the starting amount of yeast are added. Yields are reported with 55% on benzaldehyde.

......

Experimental:

1. 800g cane sugar molasses (50% saccharose), 5g potassiumdihydrogenphosphate, 2,5g MgSO4.7H2O epsom salt, 16g ammoniumsulfate, 4liters water.
This is adjusted to a ph of 4,7-5,2 with 50% phosphoric acid. 164g yeast are subjected to fermenattion for 30 to 45 minutes then 32g benzaldehyde and 48ml acetaldehyde (50% in water) are added in four portions every 60 minutes. After 4 to 6 hours 20g l-PAC have formed. The yeast is separated, the liquid is extracted with 3 to 4 equal portions of ether or DCM. The raw extract can be used as is for the reductive alkylation to l-ephedrine.
Isolation of the pure l-PAC so wanted: The raw extract in ether is shaken with sodiumbicarbonate solution (10%) which removes the byproducts mostly the carbinolo is then extracted by the bisulfite additionproduct, followed by neutralisation in water, extraction with ether again and distillation at 120°C to 125°C at 12mm/Hg.
44% yield on benzaldehyde.

2. Nutrients like in 1. 40mg thiamine are added, 5 to 7 hours 24,5g l-PAC, 55,5% yield.

3. As in 1. plus 5% corn steep liquor, 6 to 8 hours, 55,5% yield.

4. Instead of corn steep liquor, 10% whey is used. 6 to 7 hours. 62,5% yield.

5. Like in 1., but instead of 800g only 320g cane sugar molasses is used and 1600g brewers wort (17% to 18%sugar) is added. 8 to 10 hours, 34g l-PAC, 76,5% yield.

....


Whey, cornsteep liquor and brewers wort contain thiamine and obviously other enzymes favorable in the biosynthesis. The use of acid-hardened yeast as described in the prior art is told to have also good yields.



Never bother with exotic yeasts, bakers yeast is it. And no supercritical solvents, no gentech, no raindance is needed.
Brewers wort and fresh whey are NOT easy to prepare without bacterial contamination. I recommend to use thiamine and to add some sodium pyruvate so available. There are ways to produce the wanted pyruvic acid by another batch of yeast under growing conditions though and to filter off this yeast and to add the liquid which contains 10-20% pyruvic acid so done right. Using a bigger volume of the broth makes it possible to work without acetaldehyde, adding ethylalcohol (not denaturated!) is good idea too.
It seems to me that most here are not looking for a working method, but for excuses why they cannot do this by themselves.

It wont get any easier.
Who wants to do this has to learn to make benzaldehyde, thats it. Who can make benzaldehyde has eliminated the limiting factor, then the only question is a bigger bucket. Yields on benzaldehyde and on volume of the broth get interesting again when the scale of the operation gets more professional aka batches with more than 250 gram of product are to be processed, actually there is a logistical gap between about 200 gram and 1 kg, it makes no sense to aim for anything inbetween.

The biosynth is like the monster of Loch Ness. It surfaces from time to time and vanishes again. One difference: The biosynth exists. Most ephedrine worldwide is produced this way.



/ORG frown

......
 
 

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