Extraction of piperine from white pepper

hello you all due to a copyright claim on my three-year-old pepperon video i had to put a new audio on it so this is a re-upload but this time it is in english and not in german i hope you enjoyed the video in this video we are working with flammable and corrosive chemicals proper safety equipment must be worn so now let's dive straight into the fun our goal is to extract one piparole piperidine also known as piperine it is the most common alkaloid in pepper with percentages ranging from five to ten percent piparin 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 degrees celsius this all happened under the exclusion of light which was achieved by wrapping 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 percent of the starting weight now cotton pads are inserted into the socksled 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'm 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 and i'm always happy to 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 three 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's time to look at how a sockslide extractor works the socksled 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 a boil and the solvent vapor travels upwards the hot solvent vapor travels through 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 out all of the solvent back into the boiling flask through this process the extract concentrates in the boiling flask from there on the process starts anew the beauty of this process is that each extraction cycle is performed with the same solvent but the solvent is always fresh because it is continuously distilling into the extraction chamber this allows you to extract nearly a hundred percent 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 extract it for a further five hours if you're short on time and you don't need as much pepperon as you can get i highly recommend using a causa 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 percent 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 easter 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 off all of the ethyl acetate using a water bath the water bath is used to distill to dryness without the risk of burning the crude product the crude product is then solvated in warm ethanol and the process is continued as normal with the equipment i now have i would simply use my rotational evaporator for this step but for most amateur chemists such things are just as easy to come by as a solid bar of platinum the concentrated extract is now filtered through some cotton to remove any residual pepper or other impurities 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 piperine the process is very simple and works just like the production of soap in our case the hydroxide ions react with the easter 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 piperine but only very slowly this can also be seen in the harsh conditions that are needed to hydrolyze piperine into piparinic acid in 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 glass filters for this step the goopy mixture clocks them pretty bad and it's a pain to clean them out i had to use hot tetrachloroethylene 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 system now we are finally approaching the last step getting our piperine 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 piperine is only soluble in the ethanol but not in the water we are mixing in because of this the solubility of piperine reduces and it starts crashing out the bright yellowish looking clouds you can see are actually very fine peppering crystals which are forged out of solution i know that through the display and especially with my old camera it doesn't seem like it but i find the way the crystals are coming out of the solution very interesting and beautiful after no more cloudiness occurred i gave the mixture a good stir and put it into the freezer for 12 hours this is important it gives the piperine enough time to clump into bigger clusters of crystals which can be filtered i tried filtering the pimperine 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 kept boiling and water is added up to the point that the piperine that is crashing out is just redissolving this recrystallization step can be done several times to increase the purity of the product just remember that with every recrystallization you're losing some of your product after the filtration i was left with 4.4 grams of a bright yellow crystalline 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 of my patreon supporters and all of you guys your positive feedback is one reason why i'm doing all of this so only one thing left to say have fun and do not kill yourself you

Channel: Hazel Chem

Views: 3,218

Rating: 4.944056 out of 5

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Id: 1hCAY-NU1Qo

Length: 10min 49sec (649 seconds)

Published: Thu Sep 03 2020