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myristicinaldehyde
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Black Pepper Extraction results!
So i tried this myself. I used my old, unopened tin of fine black pepper, about 100g (box says 113g, didn't bother to check) and made a slurry with
250ml of 75% 2-propanol.
This was microwaved for 2 min, with a flask of cold water to make a crude reflux, allowed to rest for 2 h and repeated 3 times. It was filtered the
old, old fashioned way ala coffee filter.
Smells fab, stains everything. ![:D](./images/smilies/biggrin.gif)
I added some NaOH dissolved in the 2-propanol (just enough to dissolve in 10ml) and added this to the extractive. I filtered this again, and
evaporated down to 150ml. This was then added to 200ml (arbitrary excess) of cold water, and chilled strongly for 24h. The result was a milky white
suspension, with a pale taupe powdery crystal at the bottom.
I then filtered this by coffe filter. This is a bad idea.
The powder happily turns into a sticky resin, which smells amazing but is impossible to get off the paper. Despite this enormous mechanical loss, I
was left with a dismally small, very spicy (yes I tried )yellow brown gummy
blob, 1.5g This was very surprising, considering the mechanical loss and age of the pepper. This was the crude yield. If I decide to do anything, the
next course of action would be to wash the paper in hot solvent, and dissolve the gum, and recrystalize. However, I am not sure how to do that- adding
water made the precipitate too fine, which may have caused the gumming up.
For some reason, this box of "Malabar pepper" has the Taj Mahal on it!
[Edited on 2016-6-29 by myristicinaldehyde]
[Edited on 2016-6-29 by myristicinaldehyde]
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Thread Moved 29-6-2016 at 13:28 |
chemplayer...
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It smells good doesn't it!
When we've done this before using black pepper we find that the addition of the hydroxide causes the proteins etc. in the mixture to coagulate and
form a sticky precipitate, possibly along with some resins and other materials. We filtered these off to give a clear solution again, then slowly
added water to the resulting solution which results in the piperine precipitating out. Without getting rid of the brown sticky stuff the piperine you
get is brown and sticky and horrible.
It may be that you need to reduce down the initial IPA solution of piperine that you filter down to about 10-15ml before adding the hydroxide (as per
the literature) - this concentration increase probably helps the brown resinous stuff to separate out of solution more easily. Then filter, save the
filtrate, add water as before, then leave for 24 hours to aggregate / crystallise.
Alternatively see if you can do it with white pepper - this doesn't normally require a filter stage as there's less gunk in there, and the piperine
product is a nice light yellow colour and recrystallises into beautiful needles.
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Bot0nist
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I never messed with a microwave, but I can attest to what chemplayer... has written. A while back, I had some success with a similar
procedure and made a post.
Black pepper to piperine 91% IPA small scale
[Edited on 30-6-2016 by Bot0nist]
U.T.F.S.E. and learn the joys of autodidacticism!
Don't judge each day only by the harvest you reap, but also by the seeds you sow.
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myristicinaldehyde
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I will try with white pepper next time- fresh, too. Probably the hydroxide addition and half-assed evaporation was insufficient to eliminate the crap.
The crystals I received were very, very fine. I think too much water did this.
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zed
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I have a question about your name. I have queried several posters about the odor of Myristicinaldehyde. Some say "awesome", some say "not much
odor". Have you worked with this material? What does it smell/taste like?
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aga
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The OP is YATP so don't hope for too much.
Certainly best to not hope for any Actual Chemistry Actually Happening.
If a full write-up including photos of any actual experiment done by the OP get posted, i will go and buy a hat, then eat it.
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NEMO-Chemistry
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Quote: Originally posted by myristicinaldehyde ![](images/xpblue/lastpost.gif) | So i tried this myself. I used my old, unopened tin of fine black pepper, about 100g (box says 113g, didn't bother to check) and made a slurry with
250ml of 75% 2-propanol.
This was microwaved for 2 min, with a flask of cold water to make a crude reflux, allowed to rest for 2 h and repeated 3 times. It was filtered the
old, old fashioned way ala coffee filter.
Smells fab, stains everything. ![:D](./images/smilies/biggrin.gif)
I added some NaOH dissolved in the 2-propanol (just enough to dissolve in 10ml) and added this to the extractive. I filtered this again, and
evaporated down to 150ml. This was then added to 200ml (arbitrary excess) of cold water, and chilled strongly for 24h. The result was a milky white
suspension, with a pale taupe powdery crystal at the bottom.
I then filtered this by coffe filter. This is a bad idea.
The powder happily turns into a sticky resin, which smells amazing but is impossible to get off the paper. Despite this enormous mechanical loss, I
was left with a dismally small, very spicy (yes I tried )yellow brown gummy
blob, 1.5g This was very surprising, considering the mechanical loss and age of the pepper. This was the crude yield. If I decide to do anything, the
next course of action would be to wash the paper in hot solvent, and dissolve the gum, and recrystalize. However, I am not sure how to do that- adding
water made the precipitate too fine, which may have caused the gumming up.
For some reason, this box of "Malabar pepper" has the Taj Mahal on it!
[Edited on 2016-6-29 by myristicinaldehyde]
[Edited on 2016-6-29 by myristicinaldehyde] |
Sounds like my frit glass funnel would take a hit with this lol. Cinnamon today maybe pepper later in the week.
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myristicinaldehyde
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Quote: Originally posted by aga ![](images/xpblue/lastpost.gif) | The OP is YATP so don't hope for too much.
Certainly best to not hope for any Actual Chemistry Actually Happening.
If a full write-up including photos of any actual experiment done by the OP get posted, i will go and buy a hat, then eat it. |
Interesting offer! What kind of hat? Don't expect to be blown away by advanced Org. chem- I still don't have a hotplate stirrer! Or any real acids.
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myristicinaldehyde
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Quote: Originally posted by NEMO-Chemistry ![](images/xpblue/lastpost.gif) | Quote: Originally posted by myristicinaldehyde ![](images/xpblue/lastpost.gif) | So i tried this myself. I used my old, unopened tin of fine black pepper, about 100g (box says 113g, didn't bother to check) and made a slurry with
250ml of 75% 2-propanol.
This was microwaved for 2 min, with a flask of cold water to make a crude reflux, allowed to rest for 2 h and repeated 3 times. It was filtered the
old, old fashioned way ala coffee filter.
Smells fab, stains everything. ![:D](./images/smilies/biggrin.gif)
I added some NaOH dissolved in the 2-propanol (just enough to dissolve in 10ml) and added this to the extractive. I filtered this again, and
evaporated down to 150ml. This was then added to 200ml (arbitrary excess) of cold water, and chilled strongly for 24h. The result was a milky white
suspension, with a pale taupe powdery crystal at the bottom.
I then filtered this by coffe filter. This is a bad idea.
The powder happily turns into a sticky resin, which smells amazing but is impossible to get off the paper. Despite this enormous mechanical loss, I
was left with a dismally small, very spicy (yes I tried )yellow brown gummy
blob, 1.5g This was very surprising, considering the mechanical loss and age of the pepper. This was the crude yield. If I decide to do anything, the
next course of action would be to wash the paper in hot solvent, and dissolve the gum, and recrystalize. However, I am not sure how to do that- adding
water made the precipitate too fine, which may have caused the gumming up.
For some reason, this box of "Malabar pepper" has the Taj Mahal on it!
[Edited on 2016-6-29 by myristicinaldehyde]
[Edited on 2016-6-29 by myristicinaldehyde] |
Sounds like my frit glass funnel would take a hit with this lol. Cinnamon today maybe pepper later in the week. |
An interesting experiment to do would be to compare cheap cassia bark cinnamon with the real deal. Real cinnamon is expensive in the US.
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macckone
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Quote: Originally posted by aga ![](images/xpblue/lastpost.gif) | The OP is YATP so don't hope for too much.
Certainly best to not hope for any Actual Chemistry Actually Happening.
If a full write-up including photos of any actual experiment done by the OP get posted, i will go and buy a hat, then eat it. |
extraction and purification is the basis of much chemistry.
these basic experiments are perfect for beginners.
these is little danger and few chemicals required.
the write up is not horrible.
you were less negative when more drunk.
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NEMO-Chemistry
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Slightly off topic........sorry
Anyone know where you can get the filter inserts for soxhlet extractors? I saw them being used on you tube and they look well handy for cinnamon.
I have the cinnamon bark rolls (is that the real stuff??) and the powdered stuff.
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myristicinaldehyde
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I have some experience writing papers (humblebrag- I got 2nd place in the New
York City Quality of Life Competition! and won 2 scholarships from it! <humblebrag/>
but I never wrote a writup.
Here it is as a pdf. I was lazy with the references, I had to write a literature review for school, that was 4 pages of APA citations.
I also probably screwed up the appendix- I forgot to take a picture, and the order might be off out of ~30 I chose 16, and many look similar.
Someone owes me a study on the "Digestion of NON-LEATHER and NON-STRAW human headgear!"
https://drive.google.com/open?id=0Bwy1IbkbAveKUS15WXVOY2tsMD...
[Edited on 2016-7-3 by myristicinaldehyde]
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myristicinaldehyde
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Too late to edit, but the very end I have 2 quotes. These refer to benzoquinones.
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myristicinaldehyde
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Quote: Originally posted by NEMO-Chemistry ![](images/xpblue/lastpost.gif) | Slightly off topic........sorry
Anyone know where you can get the filter inserts for soxhlet extractors? I saw them being used on you tube and they look well handy for cinnamon.
I have the cinnamon bark rolls (is that the real stuff??) and the powdered stuff. |
Powdered is almost certainly cassia, if you are in the US. In my opinion, real cinnamon, tastes less "woody", and has a peculiar balsamic, warm and
smooth sweetness/spiceness. Cassia is woody, almost powdery and (to me) "sharp". It's dirt cheap, too esp. compared to cinnamon.
I noticed that usually real cinnamon brags about it's superiority- 100% Organic! Exclusively from a single island in Indonesia! etc. Cinnamon from
the EU is always real, or should be- Belgium strongly frowns on selling cassia bark as cinnamon.
But, I am no expert, just dissatisfied with cheap cinnamon. Chemplayer's the chef here! lol
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NEMO-Chemistry
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Quote: Originally posted by myristicinaldehyde ![](images/xpblue/lastpost.gif) | Quote: Originally posted by NEMO-Chemistry ![](images/xpblue/lastpost.gif) | Slightly off topic........sorry
Anyone know where you can get the filter inserts for soxhlet extractors? I saw them being used on you tube and they look well handy for cinnamon.
I have the cinnamon bark rolls (is that the real stuff??) and the powdered stuff. |
Powdered is almost certainly cassia, if you are in the US. In my opinion, real cinnamon, tastes less "woody", and has a peculiar balsamic, warm and
smooth sweetness/spiceness. Cassia is woody, almost powdery and (to me) "sharp". It's dirt cheap, too esp. compared to cinnamon.
I noticed that usually real cinnamon brags about it's superiority- 100% Organic! Exclusively from a single island in Indonesia! etc. Cinnamon from
the EU is always real, or should be- Belgium strongly frowns on selling cassia bark as cinnamon.
But, I am no expert, just dissatisfied with cheap cinnamon. Chemplayer's the chef here! lol |
I am in the UK so looks like its probably real then, also google says the rolled bark stuff is about right.
Time to make some Chloroform and ether once my yeast buck up and produce Ethanol!! Weather turned a bit cold and they seem to be on a go slow
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myristicinaldehyde
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My family is from Poland (we're in the us tho) , so we always have some "spare" wódka lying around! How high can you get the alcohol before the yeast
dies? And waht sort of yeast do you use? References seem to vary.
I should make chloroform the way NurdRage did it, starting from methyl ethyl ketone (2-butanone i tink) so I get propionic acid instead of boring ol'
acetic.
If we don't study the mistakes of the future we're doomed to repeat them for the first time.
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S.C. Wack
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Cellulose extraction thimbles are available, the problem is they've always been expensive for what they are. Glass thimbles are best bought from China
or ebay sellers who can provide accurate OD measurement but otherwise have no clue. Neither type were used with my piperine extractions in http://www.sciencemadness.org/talk/viewthread.php?tid=4698&a...
A plug of cotton or glass wool, or a tea bag sort of operation works well enough if packed correctly.
A key feature of that, the best isolation method there is from a Soxhlet and denatured alcohol, is a Mr. Coffee. Alcoholic KOH precipitates piperine
in large enough crystals to wash, and boiling hot water conveniently removes most of that oil.
[Edited on 3-7-2016 by S.C. Wack]
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NEMO-Chemistry
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Quote: Originally posted by S.C. Wack ![](images/xpblue/lastpost.gif) |
Cellulose extraction thimbles are available, the problem is they've always been expensive for what they are. Glass thimbles are best bought from China
or ebay sellers who can provide accurate OD measurement but otherwise have no clue. Neither type were used with my piperine extractions in http://www.sciencemadness.org/talk/viewthread.php?tid=4698&a...
A plug of cotton or glass wool, or a tea bag sort of operation works well enough if packed correctly.
A key feature of that, the best isolation method there is from a Soxhlet and denatured alcohol, is a Mr. Coffee. Alcoholic KOH precipitates piperine
in large enough crystals to wash, and boiling hot water conveniently removes most of that oil.
[Edited on 3-7-2016 by S.C. Wack] |
Thank you for the info, i did find a source of the paper thimble inserts, expensive is being polite!
Is denatured Alcohol the same as Methanol? or is it ethanol? I ask because i can find two products called denatured and both are different.
Methanol i can buy fairly cheap, Ethanol i make because i like doing it. I need to buy more solvents but some are getting hard to find, we dont have
many OTC sources up here and postage is getting more than the products!
I have found a wholesalers for ethnic food, roughly 40 miles away but worth the trip now and then. Loads of spices and strange ingredients in large
packs for very cheap prices .
Anyway thank you again for the information, now i need to unblock my extractor lol
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Denatured alcohol brands as sold in hardware stores here are over 50% methanol, and often a little MIBK, and are dry. I think either or any mix of the
two would be fine. Maybe more or entirely 100% IPA would be better or not, but denatured is usually the cheapest option. Aqueous ethanol is more
uncharted for me but my instinct is against much water and my experience with trying precipitation with water were a mess.
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Nectarine
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for soxhlets, I use glass wool as filter plug.
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woelen
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Quote: Originally posted by aga ![](images/xpblue/lastpost.gif) | The OP is YATP so don't hope for too much.
Certainly best to not hope for any Actual Chemistry Actually Happening.
If a full write-up including photos of any actual experiment done by the OP get posted, i will go and buy a hat, then eat it. |
Why this negative response? By behaving like this you reach the opposite effect
of what you want. If you really want people to do actual chemistry, then do not put them off with such negative non-constructive remarks. Recently I
have seen too many of this kind of responses and my tolerance for them is melting away like snow in hot sunshine, so be warned . . .
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Due too opening the little bag of powder with a bit too much force.....I have had to go with another cloves extraction as my cinnamon powder get
spread all over the floor! I will get more friday when i get to the shops.
I posted a pic a while back of cloves left in chloroform to soak for a while, i got 3/4 distinct layers. The one i did the other day i had to use IPA,
i have run out of bleach and therefore chloroform! I will grab more when shopping.
Also the people i normally get acetone from now only sell acetone that isnt acetone! no idea whats in it but its thick and gloopy and smells nothing
like Acetone, searching on here i found a thread with chloroform made with IPA.
Crap thread not much info but i will give it a shot. Anyway a couple of days in and the IPA cloves extraction is totally different from the chloroform
one, this time its all one colour and a single layer.
I will leave it another 48 hours and take a pic, i will post both pics side by side so you can see the difference. I intend to take some of the IPA
one and see if i can salt out any layers.
I like the chloroform one because it looks like it separates the tannins into two almost distinct layers.
Is HCl the normal goto option for acid base extractions? I think i read with alkaloids etc this will give the hydrochlorides? Or maybe it was extract
with base then use HCL........ NVM i will read that bit up again and try it out.
Finally got a half arsed bench sorted in the bit of garage i can have, so fingers crossed and full steam ahead at the weekend with some chemistry! The
luxury of an electric socket in the garage is beyond description.
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Fyndium
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I wonder why there is no solubility data of piperine in acetone? It should be a good general solvent that dissolves pretty much all organics, so why
is it not used for extraction of piperine? There are sources that recrystallize it from acetone, and since soxhlet column is around 40-50C during
extraction, the logic says it is very soluble in it.
For the record: I'm currently running a batch of black pepper with acetone soxhlet. I run a batch until the acetone is colorless and change the batch,
and collect all the dissolved residue in the boiler. I'll see what it results.
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Boffis
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Does anyone know why most people use black pepper instead of white in spite of the fact that white pepper generally contains more piperine and less
resin?
Keep us informed Fyndium! I have my soxhlet equipment out at present and might try this with white pepper corns. In the past I have used the simple
soak-filter-distill off solvent method using 3 extractions and large amounts of solvent, it works fine but is messy.
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Fyndium
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For me it's opportunism. White pepper is currently much more expensive than black. In general the price difference seems to be marginal.
It seemed at morning like something was crystallized out of the acetone solution to the walls of a rbf. It might have been just settled solids. I
reflux and change batches with the same acetone, haven't yet needed to add more, and biggest losses come from acetone binded in the depleted pepper.
I'm not sure how much can I extract with the same acetone batch, but I'll keep going as long as it seems reasonable. I suppose the resin does not
decompose when refluxing at 56C.
I actually changed my soxhlet to my 500mL comp dropper funnel, as the volume was so small. The dropper can hold about 250g of pepper per load, and it
can be cycled more efficiently.
I'm not quite sure how efficient the extraction is, since the extracted pepper still smells like pepper.
[Edited on 23-1-2021 by Fyndium]
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