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Extraction of piperine from white pepper

Hazel Chem - 2020-09-03

Hey you all in this video I will show you hoe to get good quality piperine from white pepper. Hope you enjoy the video 

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Hazel Chem - 2020-09-04

Hello you all
Due to a copyright claim on my three-year-old piperin video I had to put a new audio on it, so this is a reupload. But this time it is in English and not in German. Hop you enjoy the video.
In this video we are working with flammable and corrosive chemicals proper safety equipment must be worn. So now lets dive straight into the fun.
Our goal is to extract 1-Piperoylpiperidine also known as piperine. It is the most common alkaloid in pepper with percentages ranging from 5-10%. Piperine is soluble in lipophilic solvents.
To reduce the amount of water present in the pepper I dried 240 grams over the course of around 120 hours at a temperature of 80°C. This all happened under the exclusion of light which was achieved by rapping everything in aluminum foil. I highly recommend using white pepper because the shell which contains the highest percentage of resin and fat has been removed.
With drying the weight was reduced by 42 grams which corresponds to 17,5% of the starting weight.
Now cotton pads are inserted into the Soxhlet extractor to prevent the pepper from getting sucked into the siphon tube. This is one of two options and you can also use a special cellulose shell for your extraction material. I decided to go with this approach because it allows me to fill in more material. But you have to keep in mind that your extraction material can lead to very slow flow rates of the solvent thus decreasing the efficiency of the process. Now 97,6 grams of the pre dried pepper are filled into the Soxhlet apparatus.
While I am recording this, I am in the middle of the renovation of my lab, which desperately needed a new roof and some further improvements. For example, I added new lights, painted the fume hood and the floor with special paints for water and chemical resistance and I treated all the rusting metal parts. If you have an idea for what else I should add to the lab write me a comment I am always happy get new inputs which allow me to improve the lab. If you like to support, my work via Patreon! Link is in the video description.
As solvent I chose ethyl acetate because it can be easily distilled from nail polish remover. The used ethyl acetate was pre dried using 3 angstrom molecular sieves to get rid of any remaining water. 300 milliliters of dry ethyl acetate are added to the boiling flask followed by a magnetic stir bar. Afterwards the apparatus is assembled and connected to the cooling water.
So now it is time to look at how a Soxhlet extractor works. The Soxhlet extractor is divided into three parts with different functions. The first part is the boiling flask. In the boiling flask (hence the name) the solvent is brought to boil and the solvent vapor travels upwards. The hot solvent vapor travels thru the vapor tube into the second part, which is the extraction unit. There it travels up even further until it reaches the third and final part which is the condenser. Upon reaching the condenser the vapor turns back into a liquid and drops into the extraction chamber. The still hot liquid solvent reaches the extraction material and solvates some of the molecules that are soluble in it. When the solvent reaches a certain level the siphon effect kicks in and sucks all of the solvent back into the boiling flask. Thru this process the extract concentrates in the boiling flask. From there on the process starts a new. The beauty of this process is that each extraction cycle is performed with the same solvent BUT the solvent is always “fresh” because it continuously distills into the extraction chamber. This allows you to extract nearly 100% of the soluble molecules.
It should be noted that due to the fine pepper powder it may happen that the siphon effect is not working as intended. But this is no real problem because after some time a slow but steady drip rate of solvent sets in. The extraction is done when the solvent in the siphon tube appears crystal clear. In my case this occurred after 25 hours. Because this was my graduation project in chemistry, I wanted to get the maximum yield, so I extracted for a further 5 hours. If you are short on time and you don´t need as much piperin as you can get, I highly recommend using a coarser grain or one of the extraction shells because it will save you a couple of hours in waiting. Now that we have performed the extraction it is time to clean up the extract. For this I transferred the extract into a distillation apparatus and reduced the volume by around 50%. This was mainly because ethyl acetate can be hydrolyzed by sodium hydroxide which we will use in the next step. As a fun chemistry fact keep in mind that caustic ester hydrolysis is a non-reversible process because the organic acid lacks the proton to reform the ester with the alcohol. Again there is room for improvement in this case I recommend to distill of all of the ethyl acetate using a water bath. The water bath is used to distill to dryness without the risks of burning the crude product. The crude product is then solvated in warm ethanol. With the equipment I now have I would simply use my rotational evaporator for this step but for most amateur chemists such thing are just as easy to come by as a solid bar of platinium. The concentrated extract is now filtered thru some cotton to remove any residual pepper or other impuritys. The next step in the cleanup is the preparation of a saponification solution. This is done by solvating around 6 grams of potassium hydroxide in 50 milliliters ethanol. You can also use sodium hydroxide instead of potassium hydroxide but there may be a slight difference in the appearance of the resin and fat soaps. I also dried the ethanol over three angstrom molecular sieves but that is optional.
The potassium hydroxide solution is used to get rid of most of the resin and fat which we extracted alongside our wanted piperin. The process is very simple and works just like the production of soap. In our case the hydroxide ions react with the ester bonds in the resin and fat to break them up and form water soluble salts. These are commonly known as surfactants and better soluble in water than in the used ethanol which leads to some of them crashing out of solution. The hydrolysis also works on the piperin but only very slowly. This can also be seen in the harsh conditions that are needed to hydrolyze piperin into piperinic acid and piperidine. The hydroxide solution is added in one go and the reaction mixture is stirred for a short period of time. The resulting mixture is filtered and the filter paper is washed once using dry ethanol. If you have access to a vacuum filtration system, I have to warn you do not use the glas filters for this step. The guppy mixture clocks them pretty bad and is a pain to clean out. I had to use hot tetra chloroethylene followed by chromic acid which both are chemicals I don´t really like to work with. But if you have a buchner funnel go for it and enjoy the time saving luxury of a vacuum filtration. Now we are finally approaching the last step: getting our piperin out of that solution. For this we are utilizing two properties of the involved chemicals. Namely solubility and mixability. Because water and ethanol are mixable in any ratio we can add more and more water to the ethanol which decreases the percentage of ethanol in the solution. The piperin is only soluble in in the ethanol but not in the water we are mixing in. Because of this the solubility of piperin reduces and it starts crashing out. The bright yellowish looking clouds you can see are actually very fine piperin crystals which are forced out of solution. I know that thru the display and especially with my old camera it doesn’t seem like it but I find the way the crystals are coming out the solution very interesting and beautiful. After no more cloudiness occurred, I gave the mixture a good stir and put it in the freezer for 12 hours. This is important because it gives the piperine enough time to clump into bigger clusters of crystals which can be filtered. I tried filtering the piperine straight after crashing it out of solution but it failed with all the filter papers I had. The last step is a recrystallization. To perform it the piperine is brought into solution in hot boiling ethanol. This mixture is keep boiling and water is added up to the point that the piperine that is crashing out is just redesolving. This recrystallization step can be done several times to increase the purity of the product. Just remember that with every recrystallization you are losing some of your product. After the filtration I was left with 4.40 grams of a bright yellow crystallin powder. The look and the weight of the product were enough to satisfy my teacher and I got a decent grade from the whole project.I want to thank all my patreon supporters and all of you guys your positive feedback is one reasons why I am doing all of this. So only one thing left to say …. Have fun and do not kill yourself

coWD 420 - 2021-02-23

So when are you gonna mane some piperidine and then MDMA? :D

Vankatanemuedobre - 2020-12-10

dude great video ! you speak English so fluently a bit jealous i really enjoyed watching.

More_Science - 2020-09-03

Excellent video! Who cares if it’s a re-upload, in enjoyed understanding what you are saying this time haha.

Hazel Chem - 2020-09-04

haha glad everyone can understand it now

mfg hazelChem

Jamide 1 - 2021-03-10

I did enjoy the German though

Full Modern Alchemist - 2020-09-04

I watch your videos all the time it was cool to see one in English. I’ll watch them in either language though. 🙂

Hazel Chem - 2020-09-04

thanks ^^ nice to know ones work is being appreciated.

mfg hazelChem

_ RubberStopperMan _ - 2020-09-04

so nise old glass from GDR! ))

Hazel Chem - 2020-09-04

haha ja well I got most of my glass quite cheep from different sources inn the former GDR. The quality of the glass is very good highly recommend using it !

mfg hazelChem

The Creative Chemist - 2020-09-03

I think this is a very nice method. I never heard of a saponification step in piperidine extraction before

Hazel Chem - 2020-09-04

well there are many papers on the mater .... but nearly all come to the conclusion that the clean up works best with this step. BUT if you have access to a good chromatography column skip the saponification and do the clean up with the column and a uv lamp.

mfg hazelChem

Ubya - 2020-09-03

nice voiceover ;)
can i ask you what chemically resistant paint you used for your lab? i don't have the space for a lab (sigh) but i've been building a fumehood from scratch for a few years, and i upgrade it as i go, right now it is bare wood, and it is no good. I planned on using metal panels, but they are not cheap nor easy to mount now.

Hazel Chem - 2020-09-04

hey so you should use wood ! no metal because metal will be corroded away in no time! lab air is pretty harsh to many materials. The paint for the fume hood was specially made for me by a local company (it also does not reflect light which is better for filming videos. But it was 40 euros per liter) the paint for the floor was a liquid polymer paint that is normally used in the garage.
ps: I highly recommend to use a motor that manages at least 300 cubic meters of air per hour

hope this helps you :D

mfg hazelChem

Ubya - 2020-09-04

@Hazel Chem it does, thanks

JOHN BLACK SUPER CHEMIST - 2020-10-17

Ubya...........Hazel chem knows more than me on the subject but i thought i would throw my 2 cents in. I built a fume hood for my buddy and i just used all wood and painted it with regular latex indoor white paint. I figured it would protect the wood and if it got stained up the regular house paint is so cheap and the fume hood so small i could just re paint it once every 5 or ten years. Seriously though except for the table part of the fume hood where you set things down and spill things on there really are no stains. The paint has been good for years although he does not use the fume hood that often. I use it more than him. The paint i always wanted to get when building metal vessels is TEFLON PAINT. To coat the metal inside of the vessel. Teflon is what a stir bar is covered in so it must be very good at fighting corrosion. But i think just regular house paint is good enough. Because teflon paint is like 5 or 6 times as much money as regular house paint. It is like $30 a pint or more.
Hazel chem mentioned fans and getting at least a 300 m3/hour exhaust fan. That is about 177 cfm (cubic feet per minute). ANYWAYS i put 3 fans in the fume hood i built and they were just exhaust fans i bought at lowe's hardware that you would put in your bathroom to exhaust water vapor when you get a shower. Most but not all are rated at 70 cfm. Times that by 3 and you got 210 cfm. I bring this up cause they are cheap fans. The minimum cfm for bathroom exhaust fans is 50 cfm. Although i made the mistake of mounting them on top and OUTSIDE of the fume hood. THEY JUST LEAKED CAUSE OF THAT. So last winter.......at the end of winter........i took the fans out and mounted them on the INSIDE of the fume hood so now there should be no leaks. HOPEFULLY. I need to do some experiments with NASTY chemicals and see if it works perfect now or not

JOHN BLACK SUPER CHEMIST - 2020-10-17

HAZEL CHEM.............Well buddy i have learned a lot from your GREAT OUTSTANDING videos. I wish i could send you a contribution but financially speaking i am barely one step up above a homeless person right now. I hope all my post did not bother you but ..that and thumbs up are what gets a video higher on the list when people search for videos. I watched all you got even the ones i watched several times in the past. Gave them all thumbs up. So you will not be hearing from me again unless you post another video or maybe i think of another question about chemistry. But that does not mean i will stop watching your videos. There are a few of them i will probably watch for the next couple years..........over and over. I really appreciate all the time and effort you put in to your videos. And to me your not just a great video creator but your also a VERY COOL DUDE. You really try to HELP people who are trying to learn chemistry. AND I RESPECT THAT A LOT BUDDY. YOU HAVE A GREAT DAY!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! Keep making videos but don't get obsessed like i was getting. Obsession takes the fun out of any activity.

Hazel Chem - 2020-10-20

Hey John :D thank you for your amazing support. It really gives me allot seeing that my videos are really enjoined by my viewers. I wish you all the best! I am a student my self and I know how it is to be broke ^^ maybe it´s because I am spending way to much money for the lab XD but to be honest money does not make one happy. I really like all your comments they are high grade chemistry! and some of them I haven't answered because I am not sure about the answer BUT I am sure that the community will answer them! have a great day :D

mfg hazelChem

JOHN BLACK SUPER CHEMIST - 2020-10-20

Hazel Chem............I figure at the least maybe some of my comments or questions would start a dialog with viewers. Keep up the great work ..........You are up there with chem player with your videos

JOHN BLACK SUPER CHEMIST - 2020-10-17

QUESTION,,,,,,,,,,,,When you do the saponification and break the esters down into salts of carboxylic acids and alcohols are you using any heat?????????? It seems like you just stirred it up with no heat. Was the pot even hot from distilling out the ethyl acetate?????? I mean i know you need a LOT of heat and reflux to break the amide bond on the piperine. But don't you need at least SOME heat to break the ester bonds for saponification???????????? Also you did not stir it long either. I have made esters but I have NEVER done a saponification. SO I DO NOT KNOW. But by watching your video i am ASSUMING that saponification is FAST and pretty much spontaneous at room temperature. Am I right in that assumption?????????

R Johnson - 2020-09-08

Neat.

JOHN BLACK SUPER CHEMIST - 2020-10-17

GREAT VIDEO...........Beautiful crystals. I like how you dried out the pepper before extracting with the soxhlet. I have had a soxhlet for like 5 years now. Used it only ONCE so far to extract plasticizer out of rubber gloves. Need to get that thing out again.

Hazel Chem - 2020-10-20

Sounds great! I recently extracted birch bark and isolated the betuline was a lot of fun!

mfg hazelChem

JOHN BLACK SUPER CHEMIST - 2020-10-20

@Hazel Chem ........I had to look up what betulin was. It says silver birch bark when dry is 30% betulin. That is a LOT. You have inspired me to get the ole soxhlet out and extract something again. The soxhlet is so cool looking

Hazel Chem - 2020-10-21

@JOHN BLACK SUPER CHEMIST very nice I wish you all the fun!

mfg hazelChem

Jack Handy - 2020-12-18

Add a poster of hot chick in lab coat to the inside of a cabinet or locker door, so u can only see it if u open the door. Nothing to trashy maybe someone inspirational.

nakrul987 - 2020-10-12

what did it taste like?

Hazel Chem - 2020-10-12

I am not nile red ^^ so I am not tasting chemicals (you should never consume something made in a amateur laboratory)

mfg hazelChem

Nicolás Rodriguez - 2020-09-03

what was the yield?

Hazel Chem - 2020-09-04

you can´t calculate a yield because you do not know how much piperin was there to begin with

mfg hazelChem

Nicolás Rodriguez - 2020-09-04

@Hazel Chem but you can state the yield you got, for example 5g per 100g of pepper
:D

Hazel Chem - 2020-09-04

@Nicolás Rodriguez Aaaaaah i see! I got 4.4 grams of piperine from 97.6 grams of pre-dried pepper

mfg hazelChem