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Actinium
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Distilling Piperine
Had a quick question about distilling piperine?
The 2-propanol coming over smells of pepper and in a not pleasant way. I tested a small portion by dropping drop by drop H20 into the alcohol. at
first a cloudiness then a small little bit of white cotton candy looking insoluble settle. as I kept adding H20 it completely suspended in solution.
Did some of the piperine make it through?
I thought that the whole point of distillation was to say, remove solvents and purify?
Can substrates come over if they are miscible in such substance?
I wanted to recycle my alcohol and get it down to a concentrate before crashing it out of solution with H20.
Can Hydrolysis be performed with regular store bought muriatic acid or does concentrated 36% solution be required?
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aga
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It is essential to watch the thermometer in the still head to get a clue as to What is 'coming over'.
Miscible substances may come over as droplets, at various temperatures.
2 or more substances forming azeotropes will come over at their azeotrope BP.
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Actinium
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I know that 2-propanol has a B.P. 82.6c, my water bath was about 87c and stirring was at about 5.5-6 on my plate/stirrer and recorded the temp coming
over at 78c-81c.
I know that thermometers can be off by +/- 1c and that placement in the still head is essential for good reading.
I understand the principle of Azeotropic distillation, i.e. steam distillation because the substance(s) are NOT miscible with eachother, however is it
possible that the piperine formed an azeotrope with the Isopropyl?
Would omitting the stirring possibly help? Its coming out 1-2 drops per second.
2 or more substances forming azeotropes will come over at their azeotrope BP
I was wondering about that, that was something that I was wanting to know how to figure out as there is another analytical project that I'm working on
and knowing how to calculate the B.P. of an azeotrope would help narrow my window on not only the distillation of the compound(s), but help in
identification along with all the other data I have been collecting.
-Ac-
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aga
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From the spreadsheet of BP data collated just yesterday, a VT between 78 and 81 C could be any of 22 compounds or azeotropes of 2 compounds in your
mix.
None of the known (to my database) 3 compound azeotropes matched.
All that means is that my data is very much limited, and identifying your distillate is difficult.
Calibrate your thermometers with Ice and Boiling water to get an accurate reading.
In the spreadsheet, the Green box is your Mean Vapour Temperature.
The Red box is how many C +/- you want to go.
Column K will say 'THIS' if it matches.
Attachment: Boiling Point Calculator.xlsx (38kB)
This file has been downloaded 370 times
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Actinium
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with update
thanks aga. 
would it be better to reduce down then crash it out of solution to work on another day or should I distille to dryness and rework to gunk prior to
hydrolysis?
I was thinking of using Dipropyl ether as suitable solvent. but one thing at a time no sense in rushing.
So tried steam distillation after reading this tasty piece, Here
Besides not being able to get my water bath over 100c, I havent sat down and figured the Azeotrope b.p. for Piperine and H2O. the only thing coming
over was about 1ml of clear distillate that had a very pungent odor, incredibly volatile. Its probably the Ethers of Piperine. that and upon getting
home just now, the 1ml-2.5ml had evaporated and the contents of the flask are as such.
250ml dH2O in 1,000ml 3-necked flask
the Piperine concetrate which looks more like tar at this point is sitting at the bottom and hardened up and is holding the stir bar firmly in place.
the water ontop looks like a cup of tea with milk in it.
Im either going to filter and try distilling the saturated H2O or allowing to settle and filter out to try and recuperate the Piperine.
As far as the gunk, I'm going to wash with P.E., followed by disolving in suitable solvent, (I do have a pint of ether in fridge, a little worried
about peroxides forming durring distilling), filter and at that point either try to get it to fall out of solution of just go with the hydrolysis,
recuperate and store away for another day.
[Edited on 19-9-2014 by Actinium]
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vmelkon
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"I do have a pint of ether in fridge, a little worried about peroxides forming durring distilling"
Peroxides don't form during heating, they just get concentrated.
You should test it for presence of peroxide.
I have kept some diethyl ether in a freezer for 1 month without any KOH and BHT. No problem.
Signature ==== Is this my youtube page? https://www.youtube.com/watch?v=tA5PYtul5aU
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aga
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Personally i've never touched Piperine, and am a complete noob to all chemistry, OC more so.
ISTR that arkoma recently distilled some Piperine.
U2U him.
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Actinium
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Quote: Originally posted by vmelkon  | "I do have a pint of ether in fridge, a little worried about peroxides forming durring distilling"
Peroxides don't form during heating, they just get concentrated.
You should test it for presence of peroxide.
I have kept some diethyl ether in a freezer for 1 month without any KOH and BHT. No problem. |
the way I understand it is that the peroxides are heavier than air and accumulate in the pot and this is where the danger lies.
I've had this either for a little over a year, also if memory serves me right from what I have read Cu will neutralize the peroxides?
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unionised
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Why are people talking about what the distillate smells like?
Piperine has no odour.
The smell of pepper is largely due to this stuff.
http://en.wikipedia.org/wiki/Rotundone
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Actinium
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Because I had pointed out that I was trying to steam distill the extract which yields the ethereal of piperine, which the Merck report I had posted 4
post up it explains that both the oil and ethereal oil are solvents for the piperine. so Unless I'm not understanding correctly, it would seem that
had I separated the piperine from it, it should be clear and have a faint to no smell of such compound which it also explains.
Here is the article again just incase you feel like looking it over. 
the water from the failed steam distillation was decanted and seems to have tons of minut crystals suspended in solution. the black oily gunk at the
bottom of the flask was stuck with my stir bar smack in the middle. I added enough 70% 2-propanol to cover, a little swirling was done. as I was
boiling water to add to a pan where the flask was waiting to my surprise was the gunk dissolved and fat plates that had the appearence of "desert
rose" stones and the color of pyrite. The alcohol is realy greasy and oily as are the crystals. as soon as its dry I'll do a m.p. test
[Edited on 20-9-2014 by Actinium]
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S.C. Wack
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You should not be expecting piperine to be distilling over with IPA, no. I would expect a rather clean separation.
True of course but BTW years ago I mentioned large amounts having a very faint and pleasant odor...aka slightest trace of IPA.
Ding! If you want to isolate piperine, follow piperine isolation procedure. It would be wise to use the best one. If you want to distill piperine,
start with asking "how does distillation work" followed by "can piperine be distilled"...start at the piperine wiki for the latter.
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Actinium
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@ S.C. Wack
may be extracted from black pepper using dichloromethane.[2] Aqueous hydrotopes can also be used in the extraction to result in high yield and
selectivity. taken from Wiki
I understand the principal of steam distillation which is a great way to separate a compound or mixture of such compounds either liquid or solid.
Besides trying to isolate the piperine the point of the experiment was to also isolate the other compounds away from it. I think there are alot of
interesting things in there not just piperine. There is no substitue for experience and no experience without failure.
Following a set of direction is important especially if you are unsure or don't understand, but if you bake a cake and you think you might of botched
it, might as well experiment at that point. no sense in throwing thinks away.
As far as the smell that carried over with the IPA was most likely the Ethereal of piperine. I managed to get a very small amount by steam
distillation.
Question? If I where to say make a solution of H2O and NaHCO3 and dripped set solution into an alcoholic extract to precipitate out the piperine,
wouldn't it form the carbonate salt of piperine?
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Nicodem
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| Quote: Originally posted by Actinium | | Question? If I where to say make a solution of H2O and NaHCO3 and dripped set solution into an alcoholic extract to precipitate out the piperine,
wouldn't it form the carbonate salt of piperine? |
How can a neutral compound form a carbonate salt?
As for the rest of your questions, it is pointless to comment as you gave no reference to the procedure you are using. I can only give one comment -
based on your questions about piperine distilling and forming a carbonate salt - that you obviously did not even bother looking at the molecular
structure of piperine.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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S.C. Wack
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| Quote: Originally posted by Actinium | | I understand the principal of steam distillation which is a great way to separate a compound or mixture of such compounds either liquid or solid.
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Not when the solid in question melts at 130C and is hardly volatile at that point.
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Actinium
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| Quote: Originally posted by S.C. Wack | | Quote: Originally posted by Actinium | | I understand the principal of steam distillation which is a great way to separate a compound or mixture of such compounds either liquid or solid.
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Not when the solid in question melts at 130C and is hardly volatile at that point. |
I whent back and read steam distillation and it was defined as solids "sublime", so if the solid can't evaporate on its own at a lower temp does that
disqualify it as a candidate for Steam distillation?
@ Nicodem britannica says its classified with lipids and alkaloids, another reference said carboxylic acid, another vanilloid. my lack of knowledge in
Chemistry makes it hard to UTSF and find what I need and what I would be looking for, if you could please explain I would be so grateful?
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Little_Ghost_again
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| Quote: Originally posted by Nicodem | | Quote: Originally posted by Actinium | | Question? If I where to say make a solution of H2O and NaHCO3 and dripped set solution into an alcoholic extract to precipitate out the piperine,
wouldn't it form the carbonate salt of piperine? |
How can a neutral compound form a carbonate salt?
As for the rest of your questions, it is pointless to comment as you gave no reference to the procedure you are using. I can only give one comment -
based on your questions about piperine distilling and forming a carbonate salt - that you obviously did not even bother looking at the molecular
structure of piperine. |
I shouldnt say this as I am a new member etc, but I have had a similar comment recently.
This is the beginners section, some of us like me are 14, some have NO chemistry experience at any level (again like me). We ask on here because there
are very experienced and knowledgeable members. Most give great guidance and so slowly and gradually we learn.
In my own case looking at the molecular structure would be a bit like someone with zero electronic experience looking at a circuit diagram. Ok google
and search engine are great IF you know can sort the crud from the good./
This is why we ask here, while learning we need the experience and expertise of others.
I am at School but I dont get taught Chemistry, I have brought books that I read, but some times I dont understand. So who exactly should we ask when
things we dont understand crop up?
Sorry but some times I think too much is expected of complete beginners.
That said in my case I have received very good help and much patience. But Like aspergers people I have a thing about injustice (google it)
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aga
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It is probably very hard for seriously experienced chemists to avoid frustration when us noobies ask (what seem to them) really basic questions, or
make really basic mistakes.
Also, as it's all Text communication, much intended information is lost, such as nuances like Humour.
Essentially we're asking for Free info, so you got to accept that any Info given out might not arrive in the format requested, or with the attitude
expected.
Personally i'm really grateful that i get any assistance at all.
The occasional slating i get for being a dumb-ass is a very small price to pay.
[Edited on 21-9-2014 by aga]
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S.C. Wack
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The missing phrase is vapor pressure. Lab manuals speak of this in the distillation part. The vapor pressure of piperine is low, and the temperature
required for a distillable vapor pressure apparently polymerizes or isomerizes it or something. If you're going to distill something, shouldn't the
first piece of information you search for be the boiling point? What's frustrating is this being one of so many threads over so many years and it's
getting worse. At some point we say fine, flush your drug precursor, detonate at the wrong time and place, and burn down your neighborhood.
If optimized piperine extractions posted here are ignored and several historically widely read lab manuals scanned for you are ignored, you risk being
ignorant. I spoke out having done some of that scanning and optimizing, and ignorant things. Piperine extraction, and chemistry and its hazards is not
intuitive at 14 like throwing rocks, so it would not be unwise to figure out how to end an experiment with a fair chance of (casualty-free) success,
before experimenting.
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Actinium
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See I had no idea that it polymerized or isomerized, everything I looked at never mentioned any of those things. and after providing the reference 2-3
times above which states you can S.D.
as a beginner seeing this in the Merck Report none the less you would think that it would hold some validity. Since its clear that it is wrong this
would be a perfect example to demonstrate that not all literature is accurate and really explaine how and why.
I'm really interested in azeotropic distillation, but guess I don't fully understand solid distillation, and if I could understand how to calculate
the some of both the V.P. im assuming you would be able to tell if its feasible or not, unless you are an experienced chemist and can just look at the
compound and determine wheather of not.
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Little_Ghost_again
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I shouldnt have commented, something else got to me I guess. Sorry guys I am not sure why I wrote what I did. It seems I am also a bit stupid, It
never occurs to me that people ask questions that relate to making drugs. I am lucky, my entire life has been lived in VERY rural locations. My
current School is in what seems to me a huge town, but to most its little more than a village.
The house I live in is not remote but (not to me anyway) but very Rural (google map DG80LG) That post code places a arrow directly above our house! As
you can see I live in the middle of nowhere and always have. The place I lived in before was remote even for me .
So I dont or rather so far I havnt had ANY contact with drugs or people that sell,use or make them. I wouldnt know drug precursor if I fell over it.
The search function is good, but I kind of think if you only use the search function then eventually all the questions get answered and no more
threads are ever posted.
Then you get the other situation, I am a member of three of other forums, all electronics related and all of them insist on starting your own threads
and not resurrecting old threads. Different forums have different preferences and etiquette, it takes time to kind of fit in and understand.
I also ask alot of very basic questions because at the moment I cant even balance an equation, I am working on learning this stuff but have to balance
that with the need for answers. This isnt just a learning exercise for me, I am trying to make and sell a product. I dont want to cause anyone harm so
my product has to be safe. Also I am very aware how dangerous chemistry can be, so again I ask before doing. I understand old hands getting peed off,
but certainly in my case I dont ask because I am lazy, I ask because I trust the information given on here.
Anyway Sorry for the outburst earlier, it happens sometimes with me. I get funny over things that most people dont.
LG
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aga
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| Quote: Originally posted by Actinium | | as a beginner seeing this in the Merck Report none the less you would think that it would hold some validity. Since its clear that it is wrong this
would be a perfect example to demonstrate that not all literature is accurate |
Definitely.
There is quite a lot of literature that Assumes that the information they have is True, and print it. Especially so on the Internet.
Hold everything you learn in the 'Might be right' box until you have experimented with it and proven it's validity for yourself.
Experimentation is how it all got discovered in the first place, and there is no substitute for sheer experience, so get distilling, fiddle with the
parameters and take load of measurements.
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arkoma
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This post is EXCELLENT. Second entry down,by bot0nist.
Melting point of piperine:130C--well above B.P. of isopropyl alcohol (2-propanol).
When I did this, only reason I distilled was to recover my solvent.
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S.C. Wack
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| Quote: Originally posted by Actinium | | seeing this in the Merck Report none the less you would think that it would hold some validity. Since its clear that it is wrong this would be a
perfect example to demonstrate that not all literature is accurate and really explaine how and why. |
It may be a better demonstration of misreading the literature and the accuracy of your interpretation.
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aga
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Fantastic post by bot0nist. Inspiring.
So inspiring that i got a Soxhlet running full of black pepper and ethanol now, and it's just done it's first cycle.
What does one do with Piperine if the extraction succeeds ?
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Little_Ghost_again
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| Quote: Originally posted by aga |
Fantastic post by bot0nist. Inspiring.
What does one do with Piperine if the extraction succeeds ? |
Kill bugs or make brandy taste funny apparently (Merck Index 13th ed)
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