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Author: Subject: Synthesis of L-Phenylacetylcarbinol(L-PAC)
hector2000
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[*] posted on 24-4-2009 at 13:10
Synthesis of L-Phenylacetylcarbinol(L-PAC)


Anyone know Synthesis of L-Phenylacetylcarbinol(L-PAC)?



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[*] posted on 24-4-2009 at 13:18


Did you try the search engine? Maybe google.



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[*] posted on 24-4-2009 at 17:39


L-Phenylacetylcarbinol is a vital intermediate for Ephedrine Hydrochloride and is prepared by the fermentation process using Molasses and yeast (Sachharomyces cerviciae). Benzaldehyde is added at regular intervals when the aldol condensation takes place to give the specific steroisomer.


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[*] posted on 25-4-2009 at 04:27


Quote: Originally posted by Sriraman  
L-Phenylacetylcarbinol is a vital intermediate for Ephedrine Hydrochloride and is prepared by the fermentation process using Molasses and yeast (Sachharomyces cerviciae). Benzaldehyde is added at regular intervals when the aldol condensation takes place to give the specific steroisomer.
Sriraman

in the wikipedia and other patent use pyruvic acid and got good yield i want to know this is possible to use just water and suger+benzaldehyde+yeast and get good yield?
how much is yield?




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[*] posted on 25-4-2009 at 06:07


If it is an industrial process I'm sure there must be details on the web about it? Besides fermentations usually produce a nice complex soup of various biochemicals as by-products. I can envisage 25L + vessels, starter cultures, sterile equipment, mechanical stirring, temperature control. I don't think biotech is really a good method for obtaining chemicals on anything less than an industrial scale.... is it?.... I may be wrong...



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[*] posted on 25-4-2009 at 06:19


hector2000 ......try searching for Organikum's posts....he has always been the expert on this field.

[Edited on 4-26-2009 by Polverone]




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hector2000
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[*] posted on 25-4-2009 at 06:28


Quote: Originally posted by panziandi  
If it is an industrial process I'm sure there must be details on the web about it? Besides fermentations usually produce a nice complex soup of various biochemicals as by-products. I can envisage 25L + vessels, starter cultures, sterile equipment, mechanical stirring, temperature control. I don't think biotech is really a good method for obtaining chemicals on anything less than an industrial scale.... is it?.... I may be wrong...

this is not industrial scale.just lab scale
before i has idea for making l-pac :
http://www.sciencemadness.org/talk/viewthread.php?tid=11319&...

but i think that method wont work and i want to know what is best method for making l-pac

[Edited on 25-4-2009 by hector2000]

[Edited on 25-4-2009 by hector2000]




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[*] posted on 25-4-2009 at 06:42


Yes what I am saying is that biotech methods do not tend to be high yielding and require a fair scale to get a good yield of product.

Take for example making alcohol, most yeasts will only get an alcohol concentration up to 12% (some as high as 20%)...before they die from living in their excrement! So working on a 25L scale you can get perhaps 2L after work up perhaps less.

So for a fair yield of your product you are likely looking at working on a 25L fermentation (at least)! You will have to have everything sterile because if you have stray yeasts or moulds or bacteria then you'll find contaminating growth and competition vs. yeast and a much lower yield and contaminated product.

I was saying that biotech methods for chemicals work industrially because of the huge scale they can operate on. They aren't the best methods for small lab scale preps!




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[*] posted on 25-4-2009 at 07:12


thanks panziandi
i found patent:
us 6,271,008
and i want try it but this patent use pyruvic acid that is expensive
if we use 25 lit container then how long may take for produce l-pac and how much l-pac we will have?
do you have better instruction with detail for making l-pac by ferment method?





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[*] posted on 25-4-2009 at 09:29


http://designer-drugs.com/pte/12.162.180.114/dcd/pdf/l-pac.n...

is the reference that the patent gives (Neuberg, C. and Hirsch, J. Biochem. Z., 1921 115 282-310) it is in German but perhaps you can translate it or gleen some information from the methods section?

The examples given in the patent give 20% yields and product in the milligram range! I do not know how it would scale.





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[*] posted on 25-4-2009 at 10:07


UNFORTUNATELY this patent language is german and i cant use it
but really thanks
i will try pyruvic acid method soon and will write my result
also i am waitng for your advise and your another patent about this method




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[*] posted on 25-4-2009 at 10:22


Pyruic acid can be made from propylene glycol or from lactic acid by oxidation (both are commercially available and cheap), I expect that the acetyl chloride > acetyl cyanide > pyruvic acid method would be unavailable to you.

Well yes that reference is in German, it is the reference that the patent you found quotes.

US patent 6,271,008 describes low volumes and a low yield some 20% as i said above, I do not know how scalable that would be though. From what I can tell, it runs at a higher temperature (50*C) so the yeast is not growing, in fact you won't really get much bacterial growth either, and it really is just utilising the enzymes as a crude catalyst rather than purified enzymes.




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[*] posted on 25-4-2009 at 11:09


Quote: Originally posted by panziandi  
Pyruic acid can be made from propylene glycol or from lactic acid by oxidation (both are commercially available and cheap), I expect that the acetyl chloride > acetyl cyanide > pyruvic acid method would be unavailable to you.

Well yes that reference is in German, it is the reference that the patent you found quotes.

US patent 6,271,008 describes low volumes and a low yield some 20% as i said above, I do not know how scalable that would be though. From what I can tell, it runs at a higher temperature (50*C) so the yeast is not growing, in fact you won't really get much bacterial growth either, and it really is just utilising the enzymes as a crude catalyst rather than purified enzymes.


you think us patent 6,271,008 is unreal?or not working well?
if i want to make 100gram l-pac how much i should use?and temp?baking yeast will work for this purpose?
making pyruvic acid by propylene glycol or lactic acid is simple or is hard?may descript it?
what is your idea about tartaric acid +potassium hydrogen sulfate method?
you advise that i use pyruvic acid method?

my old suggestion for making l-pac is this:



phenylacetic acid+lead acetate---heat--->benzyl methyl ketone

according to wikipedia this reaction is true and will work
but you think below reaction will work?


mandelic acid+lead acetate--heat-->l-pac
??
thanks

[Edited on 25-4-2009 by hector2000]

[Edited on 25-4-2009 by hector2000]




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[*] posted on 25-4-2009 at 13:46


The patent you mention states:

"EXAMPLE 1

Yeast-Mediated Acyloin Condensation of Benzaldehyde Using Pyruvic Acid

Pyruvic acid buffer was prepared by dissolving pyruvic acid (10.44 g, 119 mmol) in 100 ml of 0.05 M sodium citrate. Ammonium acetate was added to give a pH of 5.45. Benzaldehyde (106 mg, 1 mmol), petroleum ether (80 ml), ethanol (0.5 ml), baker's yeast (5 g) and the pyruvic acid buffer (5 ml) were stirred at 50° C. for 24 h. The mixture was then filtered and the yeast washed with diethyl ether.

The combined organic layers were then washed with 10% sodium carbonate. After removal of the solvent in vacuo the product was purified by flash distillation (200° C./1 mm) to give phenylacetylcarbinol (30 mg, 20% yield). Gas chromatography (GC) of the product showed pure PAC (11.88 min.). Chiral GC showed a ratio of 95:5, 90% ee."

So they made 30mg that is 0.03g of phenylacetylcarbinol, you want to make 100g that's over 3000 times the scale! If you multiply everything in their method by 3333, which you will see is starting to look a little bit silly!

And you will soon see why I told you large containers are needed!!!




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[*] posted on 25-4-2009 at 16:25
Bioreactions


Quote: Originally posted by panziandi  

...
"EXAMPLE 1

Yeast-Mediated Acyloin Condensation of Benzaldehyde Using Pyruvic Acid

Pyruvic acid buffer was prepared by dissolving pyruvic acid (10.44 g, 119 mmol) in 100 ml of 0.05 M sodium citrate. Ammonium acetate was added to give a pH of 5.45. Benzaldehyde (106 mg, 1 mmol), petroleum ether (80 ml), ethanol (0.5 ml), baker's yeast (5 g) and the pyruvic acid buffer (5 ml) were stirred at 50° C. for 24 h. The mixture was then filtered and the yeast washed with diethyl ether.

The combined organic layers were then washed with 10% sodium carbonate. After removal of the solvent in vacuo the product was purified by flash distillation (200° C./1 mm) to give phenylacetylcarbinol (30 mg, 20% yield). Gas chromatography (GC) of the product showed pure PAC (11.88 min.). Chiral GC showed a ratio of 95:5, 90% ee."
...

I'm really tickled by the idea of this. The method deserves, IMO, to be tested and a separate thread, maybe in prepublications, created for bioconversions.
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[*] posted on 25-4-2009 at 22:57


Hector2000, post one line questions without a single reference in the Beginnings section. It is pointless to be so lazy and incomprehensive in the Organic section as I will move threads where they belong anyway. Besides, what was the point of opening a new thread on the subject for which a thorough discussion with experimental results already exist in a dedicated thread?
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[*] posted on 26-4-2009 at 01:49


Quote: Originally posted by panziandi  
The patent you mention states:

"EXAMPLE 1

Yeast-Mediated Acyloin Condensation of Benzaldehyde Using Pyruvic Acid

Pyruvic acid buffer was prepared by dissolving pyruvic acid (10.44 g, 119 mmol) in 100 ml of 0.05 M sodium citrate. Ammonium acetate was added to give a pH of 5.45. Benzaldehyde (106 mg, 1 mmol), petroleum ether (80 ml), ethanol (0.5 ml), baker's yeast (5 g) and the pyruvic acid buffer (5 ml) were stirred at 50° C. for 24 h. The mixture was then filtered and the yeast washed with diethyl ether.

The combined organic layers were then washed with 10% sodium carbonate. After removal of the solvent in vacuo the product was purified by flash distillation (200° C./1 mm) to give phenylacetylcarbinol (30 mg, 20% yield). Gas chromatography (GC) of the product showed pure PAC (11.88 min.). Chiral GC showed a ratio of 95:5, 90% ee."

So they made 30mg that is 0.03g of phenylacetylcarbinol, you want to make 100g that's over 3000 times the scale! If you multiply everything in their method by 3333, which you will see is starting to look a little bit silly!

And you will soon see why I told you large containers are needed!!!

ok i will use 25lit container
you think if i use this container then how much i will have?100 gram?or less?
do you have detail about making pyruvic acid by tartaric acid method or another method?

mr nicodem excuse me but my english is very bad but you want to say there is another thread about l-pac in this forum?




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[*] posted on 26-4-2009 at 03:02


3333 x c.100 ml is 333 liters and that is the vioreactor size needed to make 100 g L-PAC a day per this patent.



[Edited on 26-4-2009 by Sauron]




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[*] posted on 26-4-2009 at 03:44


Quote: Originally posted by hector2000  
mr nicodem excuse me but my english is very bad but you want to say there is another thread about l-pac in this forum?

Sigh... Why don't you just use the fucking search engine?
http://www.sciencemadness.org/talk/viewthread.php?tid=1936
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[*] posted on 26-4-2009 at 03:49


Quote: Originally posted by Sauron  
3333 x c.100 ml is 333 liters and that is the vioreactor size needed to make 100 g L-PAC a day per this patent.

[Edited on 26-4-2009 by Sauron]

we just need 5 ml of pyruvic acid buffer solution not 100ml
and i think if we multiply 80ml(ether) to 3000 we should use240 lit and i think this is enough to use 2.5-5lit ether for separate l-pac from solution
i mistake?




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[*] posted on 26-4-2009 at 05:16


Read the patent

Benzaldehyde (106 mg, 1 mmol),
petroleum ether (80 ml),
ethanol (0.5 ml),
baker's yeast (5 g)
and the pyruvic acid buffer (5 ml)
were stirred at 50° C. for 24 h.

That is a little over 90 ml total so figure `100 ml and that gets you just 30 mg L-PAC

Times 3333 = 333 liters. Use a 350 L stirred bioreactor regulated to 50 C. That gets you 100 g if you do everything right.

You have a LOT to learn about biotech.





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[*] posted on 26-4-2009 at 05:27
brewing L-PAC


Once Upon a Time the famous Uncle Fester recommended next proportion of starters for brewing L-PAC:
1 part of glucose, 1 part of yeast, 20 parts of water, 1/12 part of Benzaldehyde.
If (as Uncle Fester claimed) you could get of 85% yield of L-PAC on your Benzaldehyde,
So to get 100 gr. of L-PAC, you probably will need 120 gr. of Benzaldehyde, 1.44 kg. of sugar, 1.44 kg. yeast,
28.8 L. of water. Considering the foam, you'll probably need volume of 50-60 litre container.

Sorry, gentlemen for my broken English.
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[*] posted on 26-4-2009 at 05:36


No comment needed re the "famous" UF.



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[*] posted on 26-4-2009 at 06:12


I am sorry Sauron. I am newcomer here. Why No comment about UF.
May be mentioned of him forbidden here?
Could you please explain more comprehensively?


[Edited on 26-4-2009 by Elena]
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[*] posted on 26-4-2009 at 07:07


I think UF methods are a little, well shall we say, unlikely to yield what they claim to yield? The %s are a little fabricated? Is the general impression I get.

Anyway my comment about requiring a large bioreactor is true, I guessed 25L before reading the patent, and before knowing what scale hector intended, Sauron indeed has a better volume at 350L for hectors scale-up.

Now then the Wattage required to maintain a 330L reaction medium at 50*C for 24hrs is going to be... quite something. Not to mention efficient stirring to keep the 16665g of yeast in suspension! And then working up the rediculous 266.64L of petroleum ether to yield your 100g of l-PAC (assuming the same % yield as in the patent which is not for sure).

Really Hector I would have thought a simple glance at the examples in the patent followed by a bit of SIMPLE maths on a calculator (in fact the rough idea of numbers comes from just a glance!) should have made you gawp at this rediculous idea...

(Using a 25L bioreactor you should in theory get approx 7g product but I shall let you do the math for that one yourself!)

[Edited on 26-4-2009 by panziandi]




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