smile
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about PEA (phenylethylamine) in chocolate
hello, I am a new member ^^
I am doing a project about extraction of PEA from chocolate. it's really difficult..= =+
I want to make a PEA now, can anyone tell me how? can do by adding something with NH2, right? thanks~
[Edited on 10-4-2004 by chemoleo]
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Esplosivo
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The extraction is extremely difficult. It will not just be a simple one stage extraction since chocolate contains a million and one types of organic
compounds.
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can do by adding something with NH2, right?
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Are you suggesting a possible extraction with ammonium hydroxide?!
Btw, what are you gonna use the PEA for? It is used as an antideppressant and is nearly as strong as amphetamine (with the exception that one does not
become tollerant to it).
Theory guides, experiment decides.
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smile
Harmless
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hmm.....I am not going to do extraction any more. I want to make PEA, how?
well....this is a project, I and my group members are going to put PEA into perfumes. 
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Nick F
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Dichloroethane + benzene + AlCl3 --> 1-chloro-2-phenylethane (via Friedel-Crafts). Purify, react with excess ammonia in an inert solvent -->
phenethylamine.
That'd be one way.
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smile
Harmless
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thank you very much~
but........I am very confused,
how to purify?
what is an inert solvent?
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vulture
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Let's see, you're going to carry out an organic synthesis, but you have no clue what an inert solvent is or how to purify your product?
One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
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smile
Harmless
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| Quote: | Originally posted by vulture
Let's see, you're going to carry out an organic synthesis, but you have no clue what an inert solvent is or how to purify your product?
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yes.......
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Geomancer
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| Quote: | Originally posted by smile
| Quote: | Originally posted by vulture
Let's see, you're going to carry out an organic synthesis, but you have no clue what an inert solvent is or how to purify your product?
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yes....... |
Glad we got that cleared up. Wait--it get's worse. Not only do you have no understanding of the concepts needed to successfully complete such
a synthesis, you seem to have no understanding of what your target is. The PEA in perfume is phenylethylalcohol, not the amine, found
in chocolate, among other things.
Very briefly, inert solvents are those that won't react with anything that you're using in the reaction, under the
conditions you use. Water, for example, has many excellent properties as a solvent, but it is also somewhat reactive, i. e. not inert in many
reactions. Purification is needed because the thing you have when you're done your reaction contains not only the product, but the solvent,
unreacted starting materials, and products from side reactions. It can be done in many ways. Some of the basic techniques are recrystalization,
distillation, and chromatography.
I have my doubts about the current proposed strategy. Using excess benzene would prevent polyalkylation, but that would open up the possibility
of polyarylation of the ethane.
One possible alternative is to start from styrene, react with aqueous peracid (you could try cold permanganate), dehydrate the diol with
H<sub>2</sub>SO<sub>4</sub>, and do a reductive amination. All these reactions should be found in standard organic texts.
Rhodium's drug chemisty site gives plenty of procedures for compounds of this type. Decarboxylation of phenylalanine is attractive.
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Nick F
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"Using excess benzene would prevent polyalkylation, but that would open up the possibility of polyarylation of the ethane."
That's why I said purify .
I was half-joking anyway...
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smile
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| Quote: |
Glad we got that cleared up. Wait--it get's worse. Not only do you have no understanding of the concepts needed to successfully complete such
a synthesis, you seem to have no understanding of what your target is. The PEA in perfume is phenylethylalcohol, not the amine, found
in chocolate, among other things.
oh...I see...
Very briefly, inert solvents are those that won't react with anything that you're using in the reaction, under the
conditions you use. Water, for example, has many excellent properties as a solvent, but it is also somewhat reactive, i. e. not inert in many
reactions. Purification is needed because the thing you have when you're done your reaction contains not only the product, but the solvent,
unreacted starting materials, and products from side reactions. It can be done in many ways. Some of the basic techniques are recrystalization,
distillation, and chromatography.
oh, I got it. Well....I just learn the purifying method last week..
I have my doubts about the current proposed strategy. Using excess benzene would prevent polyalkylation, but that would open up the possibility
of polyarylation of the ethane.
One possible alternative is to start from styrene, react with aqueous peracid (you could try cold permanganate), dehydrate the diol with
H<sub>2</sub>SO<sub>4</sub>, and do a reductive amination. All these reactions should be found in standard organic texts.
can I use the method given by Nick F? I don't have any organic texts..
Rhodium's drug chemisty site gives plenty of procedures for compounds of this type. Decarboxylation of phenylalanine is attractive. can I know the address of the site? |
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The_Davster
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Rhodium:
www.rhodium.ws/chemistry
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vulture
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This thread is going downhill FAST.
Unless smile proves he knows WTF he's about to do and get's off his lazy ass, this thread is going to be closed.
One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
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chemoleo
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Indeed it is.
As Esplosivo said, it will be extremely hard to purify it from chocolate, simply because it contains many additional semi-unpolar substances, such as
fats, flavourings etc.
Unless of course, you have a fully equipped chromatographic laboratory.
For an initial (crude) purification of PEA from chocolate, I suggest the following:
1) Melt 500g of chocolate in a large amount of water, and stir for a long time. Hope that most of the sugar dissolves. YOu have to use a very large
amount because the PEA conc. is so low.
2) As phenylethylamine dissolves in water (checked Roempp, it dissolves in H2O, EtOH, ether), it should be in the aqueous solution BELOW the molten
fats (fats are lighter than water).
3) Add alcohol, and precipitate whatever is not soluble in alcohol. Discard precipitate, and keep the filtrate.
4) Now, evaporate the alcohol. Get rid of it. Then add H2SO4 (strongly dilute), to form the phenylethylamine salt, until a low pH is reached (i.e. pH
2). At this point, filter out any precipitate once again. Discard it.
5) Add Ether (which preciptiates ionic compounds), or possibly ehtanol. This should precipitate the ionic salt of PEA (I.e. PEA HSO4), among
everything else that behaves similarly. This should contain a highly concentrated version of PEA HSO4 however.
6) Take the precipitate, and add CaOH2 (in aqueous solution). CaSO4 should form, and precipitate. Phenylethylamine should be in the solution above. A
slight ammoniakal smell should be noticable (this is what it smells like).
Many people have been wondering about PEA in chocolate. Studies have shown however, that PEA is broken down in the stomach, and thus only very small
amounts reach the brain. There are more susceptible individuals however.
I suggest you search google with 'phenylethylamine in chocolate', it turns up heaps of links.
For instance,
http://www.chocolate.org/pea.htm
http://panicdisorder.about.com/cs/shfitness/a/chocolate.htm
and so on.
Sadly I have a feeling that my effort here is in vain - so I suggest, smile,
before you ask further questions (that is a warning), to just read up a little bit to find out more about chemistry, purifications and so
on.
You cannot expect us to walk you through a full synthesis/purification without even knowing what inert solvents and so on are, and without any will to
look up the address yourself for Rhodiums site, and ... indeed, without bothering to find an organic chemistry text book, which can
be found in the smallest of libraries!!
Make some effort!
Never Stop to Begin, and Never Begin to Stop...
Tolerance is good. But not with the intolerant! (Wilhelm Busch)
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Blind Angel
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It's easter, everyone has chocolate, 4kg or more isn't hard to find
/}/_//|//) /-\\/|//¬/=/_
My PGP Key Fingerprint: D4EA A609 55E4 7ADD 8529 359D D6E2 33F6 4C76 78ED |
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unionised
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I just checked. Chocolate emulsifies in hot water.
It might be better to start by extracting the chocolate with DCM, filtering off the sugars and stuff and then trying to extract the PEA from that
extract with dilute acid.
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chemoleo
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Ok, good to know.
Does emulsion mean though that water solutes don't go into solution, though? I should think they would (providing good heat, and rigorous
stirring)
In case of an emulsion - I guess one could try centrifugation, fat globules are going to be lighter than water & solutes, and thus separate. (As
most will lack a centrifuge, you could probably just wait until it settles - gravity is just a weak centrifuge  )
[Edited on 13-4-2004 by chemoleo]
Never Stop to Begin, and Never Begin to Stop...
Tolerance is good. But not with the intolerant! (Wilhelm Busch)
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unionised
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Left overnight to settle the mixture gave 3 layers. Presumably these are cellulose + such like; water with the sugars etc; and the fatty stuff.
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vulture
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Dumb question: Why extract PEA from chocolate, extracting it from cacao powder (without added sugar and other shit, take a good brand) should be
easier, no?
[Edited on 13-4-2004 by vulture]
One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
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IvX
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yay I get to help
When you make chocolate from cocoa powder you have to separtae it in three diferent parts: the crude chocolate, the cocoa butter(white chocolate) and
some other crap that you cant eat.
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PHILOU Zrealone
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Pea in chocolate beurk....I prefer peanuts à la snickers or M&M's...
No just kidding.
My idea is:
Cl-CH2-CH2-NO2 + AlCl3 + excess benzen --> C6H5-CH2-CH2-NO2 + HCl
Then
C6H5-CH2-CH2-NH2 via Zn/HCl or SnCl2/HCl or Fe/HCl
The other idea is:
C6H5-CH=O + CH3-NO2 -H(+)-> C6H5-CH=CH-NO2 + H2O
Hydrogen en catalyst goes to the desired compound.
Or:
C6H5-CH=CH2 + HCl --> C6H5-CH2-CH2Cl
C6H5-CH2-CH2Cl + exces NH4OH --> C6H5-CH2-CH2-NH2.HCl
Now if one wants to get it the hard way...OK.
First add HCl to molten chocolate (Vulture is right cacao powder is way easier to process than chocolate).Mix well for intimate mix.
The HCl will make a salt of all the amino groups.It may hydrolyse a little some faty esters but those will remain unsolubles...Except some weird
aminolipids...Cool down and filtrate the greases and precipitates...The watery acidic layer will contain the compound as a salt but also suggars ...
Then neutralise with concentrated amonia in excess...PEA will be then become unsoluble in water and be extractible with ether aside with other
aminated molecules..Suggars and acids,salts and alcools will remain in water.
Evaporate...you have an enriched Pea etheral solution...
This process only took 2 steps!
For further purification it can be handy to get...silice TLC( thin layer chromatography) and to make single and 2D elution...
PEA should be viewable under UV.
Usually it will stick to the TLC plate unless you use a tiny % of amonia in butanol...0-3% can allow migration from 0% to 100%.
The ideal way would be to synthetise a little to get the stuff as standart and make tests to get the best butanol/amonia sothat good elution and Rf
numbers (migration related).
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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carbocation
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i am very unconvinced about the psychoactive nature of PEA. It has been administered in gram doses with no effects orally, and intravenously up to
.5g. Allegedly insufflating causes mild stimulation but this has not been well documented. PEA is readily and completely metabolised to phenylacetic
acid and tyramine in the body. I would much rather just eat a bar of chocolate!!
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