Turning black pepper into piperonal cause it smells better

This long video focuses on first the extraction of black pepper (piperine), second piperine to piperinic acid, and lastly piperinic acid to piperonal. This was a fun video and took forever to do and edit. Enjoy!
Note:
No intent of further conversion to illicit substances
Sources:
www.researchga....
www.chemistrys....
archive.org/de...
pubchem.ncbi.n....
pubchem.ncbi.n....
en.wikipedia.o...
• Extracting the spicy c...
• Black Pepper Extraction
nopr.niscpr.re....
*ChemPlayer deserves all the credit for the procedures that I used!
Music by: Bensound.com/royalty-free-music
License code: BRJ0IYO21RCQOUVK
Patreon: patreon.com/Chemdelic
Discord: / discord

[@That_Chemist]

21:00 btw sodium periodate does the diol cleavage

[@chemdelic]

Interesting. I heard the KMnO4 would do it and the periodate might help or just not. Very interesting! Let me pin this for everyone to see! Thank you.

[@That_Chemist]

@@chemdelic btw the more common version is Lemieux-Johnson oxidation en.wikipedia.org/wiki/Lemieux%E2%80%93Johnson_oxidation

[@That_Chemist]

it's the exact same idea, but OsO4 instead of KMnO4

[@chemdelic]

I have heard of that one and looked into it. Then I looked into the cost and said nevermind 😂

[@nosurprise885]

I would quite like to see the kinetic of this reaction

[@neffix6976]

The gigachad move would be: Making peperine from mdma

[@TheBackyardChemist]

there is is satirical chemistry paper about making pseudo from meth, as the latter is cheaper and easier to buy these days

[@cacogenicist]

@@TheBackyardChemist - Until recently in Oregon, you couldn't get pseudoephedrine without a prescription. For some reason that didn't seem to deter Mexican drug cartels from producing plenty of meth for everyone.

[@mateusfelipecota]

​@@TheBackyardChemist do you have the name of the paper on hand?

[@thatguy431]

dude. yes!

[@thatguy431]

@@TheBackyardChemist google search for "satire paper making piperine from meth" just gave me meth recipes. and now im wanted by the feds would like to see that paper thogh sounds dope

[@CptFishrPrice]

Are you going to turn the piperonal into mdma cause it parties better? Im excited for this one!!

[@noblsht]

I thought I heard that word before somewhere OK I was thinking it was PCP but you're probably right MDMA, I think PCP is piperidine

[@bcubed72]

Thought you needed sassafras tea to party like a rock star?

[@KissMyConverseFool]

this is for smells only sir

[@codenamenel]

@@bcubed72 piperonal works just the same, you can use vanillin as well an extract of vanilla

[@Sniperboy5551]

I was thinking the exact same thing

[@7177YT]

That sweet sweet methylene dioxy bridge. Every time I see this structure bolted to a benze ring, I can't help but smile from ear to ear and nod to a faint memory of muffled techno. Cheers!

[@vogelvogeltje]

How hilarious, I get the same feeling. I see the little bug eyes of the head and the body, and i get all giddy cause I know what could come of it 😂

[@dalethomasdewitt]

I once asked/glanced that ring to Dr. Popp. His steer was a di ether.

[@m.i.c.h.o]

“No intent of further conversion into illicit substances” sure thing bud 😉

[@TagetesAlkesta]

Ahh yes piperonal. Very interesting structure with some very interesting uses!

[@theta3404]

Our beloved 3,4-MDBA

[@divbrho_m7904]

SWIM once made piperonal by dumping piperine into a jar with acetone and a little water, then blasting the solution inside said jar with ozone (about 800mg O3 per gram of piperonal). Afterwards he added ether, decomposed the solution by addition of water, seperated the ether layer, evaporated the ether layer and was left with an amber gooey substance with an incredibly seductive smell. The yields were around 40% by mass however he never bothered with recrystallization as he used the goo directly for further fragrance manufacture.

[@chemdelic]

I did this just recently! I had a fair amount of product too.

[@kirahund6711]

Say hi to SWIM.. we know him/her well. Damn, the good ole days...

[@AlexanderSchwarz-ck3cx]

Can you tell the exact article this was in?

[@Skunkhunt_42]

​@@kirahund6711swims pronouns are they/them😂

[@unintentionallydramatic]

Ozonalysis seems really OP for fragrances of various kinds from common household materials.

[@maestro9765]

I am convinced that this channel is a social experience to test how fast you can get arrested by the DEA from making KZbin videos

[@LiborTinka]

It's calming to see someone else doing it and going through the exact same ordeals in the prep (like the filtration of piperic acid) like I have. To improve yield, you can do the last reaction in two phases (DCM + water). BTW there is another cycloaddition product between periodate and the vicinal diol produced by permanganate (syn dihydroxylation) and this should give you three products: piperonal, glyoxal and glyoxylic acid (I think). The smaller aldehydes turn to soluble hydrates and stay in water while piperonal won't hydrate and go to the organic phase. You may not have to isolate the piperic acid - just filter off piperate after the amide hydrolysis and recrystallize it. Going throug piperic acid will get rid of more of the piperidine though as you can wash it as hydrochloride. Quenching the reaction mixture with ascorbic acid will reduce all the MnO2 into soluble manganese ascorbate and this will avoid another long filtration - excess ascorbic may also protect some of your aldehyde product from oxidation during workup. It would be nice if you made a video about purification of the product via bislfuite or oxime and maybe recrystallization from aq. 50-70% EtOH - it would be nice to see it done by someone as skillful as you! The video is professional quality as well as the 'Hamilton' witty undertones :D Thanks sir for all the inspiration and reviving the spirit of good ol' chemists like ChemPlayer on YT!

[@ChemicalEuphoria]

For better yield it could have been better to not take out the chavicine, and after making piperinic and chavicinic acid ozonolysis by means of ozone followed by zinc reduction, to have way less byproducts.

[@japanjapan3102]

cool

[@Don_Soucy]

Once you try ozone, you will not go back to chemical oxidizers. @@ChemicalEuphoria

[@ashleyobrien4937]

not so sure about that, making ozone in any appreciable amount for cleavage is a VERY slow process

[@nathancheney8306]

Fell into the rabbit hole of KZbin chemistry lately and I’ve been so excited to have found you my guy! Look forward to your videos every night and although I’m definetpy not a chemist you do a really good job of making it easy to follow along. Looking forward to learning some new stuff with every upload. Much love!

[@cheeks1462]

right?! found him today, been binging his vidz yo top shelf content this

[@ThorirLenvik]

You should have porous paper timblets instead of the cotton plug. There's nothing wrong with the soxhlet. It's the cotton!

[@Gradsteranimations]

thats what im sayin

[@danaveye3977]

Or, too much and needs to be precharged with clean solvent and deventilated

[@wack1305]

What is a timblet? I can’t find anything online Edit: oh thimble

[@mustwereallydothis]

I would go so far as to say that it wasn't the cotton either. It was a defective chemist who must have failed tenth grade physics.

[@noname-80lbs]

​@@wack1305 a disposable component of Shoxhlet extractor

[@NautsuJJR]

cant wait for this channel to turn out to just be chemplayers alt with a hired VA to do the voiceover instead of the TTS

[@Anilinequeen]

I love how you show the mechanism of the reaction, keep making fun chemicals

[@apo_chromatic]

An ozonolysis of the piperic acid would probably prove to be better than the permanganate to avoid side reactions. I think ozone generators are relatively cheap, so it may be worth a shot

[@JaredBrewerAerospace]

Love your descriptions and other commentary on "subjective" observations of various properties. This experiment is very a much a sensory experience. You should try a simpler and far higher yield of piperonal from piperine that can be done in a one step process. Dissolve piperine in a minimum amount of dry acetone. Bubble ozone gas through the solution for 8-12 hours. That's it. It is possible to get ~95% yield of piperonal. I have managed 92% personally. There is a ton of literature out there on it so I won't go into the details. I believe the paper I used was from 1972 or 76. If you need it, I can dig it up for you. You end up with a reddish orange oil that is yellow around the edges in the resulting solution. Once the acetone is evaporated off it is already fairly pure, as I do not believe there are many side reactions, but recrystallization is never a bad idea. It smells exactly like a cherry gummy candy with a hint of vanilla. Note that this must be done in a fume hood! Ozone is nothing to play around with. It is one of the most oxidizing oxidizers in chemistry. Breathing in any substantial amount is like breathing in bleach vapor. The same goes with any mucous membrane. Preferentially it should be neutralized with an activated carbon filter or by passing the excess ozone through a solution of potassium iodide or sodium thiosulfate. The ozonolysis reaction is endothermic so the acetone solution gets extremely cold but it will not get cold enough to freeze the acetone.

[@ashleyobrien4937]

I was under the impression that ozonolysis was not that practical because of the small amounts produced. So, you got 92 % that's a good yield for any reaction, but how much piperine did you use ?

[@TaiGell]

You packed lower cotton ball too dense. That is why it was not syphoning.

[@minecraft115able]

this I made the same mistake

[@juggernautonfire]

I had this exact problem while doing a caffeine extraction from coffee. I've found the syphon is also hindered if the extraction material is ground too fine, it basically forms a plug and what's worse, some of the material doesn't even wet very well with the solvent. Better off using a coffee filter and coarser pepper like steak pepper and simply running more cycles.

[@hoggif]

That was my immediate thought too. If the liquid level does not rise in tube to same level, it is blocked (by cotton in this case). Liquid level in tube will rise based on simple physics, unless there is a pressure drop high enough (sometimes called block). If you have only a bit blocked tube, it may also siphon out very slowly. Normally siphoning should be done in a few seconds for a small soxhlet. Large volume with small tubes could take somewhat longer of course.

[@palamalama]

This is literally it #talking from experience

[@Samuel-m3u6q]

Ah now only a few steps away from synthesising my own mdma

[@KissMyConverseFool]

bro it is for smells only

[@wendys4306]

So he maybe do take by snort

[@jessen00001]

I would not ❤

[@grimunleashed9583]

Good idea

[@ev3rsonix392]

Its doable but you need expensive equipment like a vacuum pump for example or you'd be exposing your whole neighborhood to toxic vapors including you

[@shakogasteier6370]

This is one of the few seldom exclusion where yellow chemistry is not awful!

[@andrewbeatty3870]

I think extractions&ire would disagree

[@SetTheCurve]

For filtering, nothing beats a Buckner funnel with celite on the paper. You’ve never seen solutions get so clear, and never get a slow filter. A vacuum or aspirator is necessary with b funnels though, to hold the paper in on first pour.

[@andrews.4780]

This was a dope experiment bro your chemistry channel is really a revival to this side of KZbin keep it coming bro 👏🏼💯

[@Jamiefearon]

As an Englishman, the solution at 15:09 looks like the most perfect cup of tea.

[@That_Chemist]

usually periodate cleavage is done under acidic conditions - 2 min also sounds like a really short amount of time for the KMnO4 thing, but I don't know how long it should be run for (I haven't ever run a dihydroxylation before) - I would think if the dihydroxylation was done in a discrete step, the final periodate cleavage would be facile

[@Psychx_]

When you connect the joints of your funnel with those of the receiving flask, you can't filter with cotton because the joint forms a seal, and thus, the air in the flask has nowhere to go. Pressure buildup within the flask and the surface tension of the liquid prevent displacement of the air with the filtrate. The diameter to length ratio of 24/40 joints does contribute negatively aswell. Btw, the type of funnel you used, is called a "powder funnel" for this reason. It works fine with particulate matter in any case and only for fluid filtration when there's no seal around it. Try it out with a different funnel or an erlenmayer flask without ground joints as the receiving flask (same setup like with the coffee filters) and it will work.

[@timecode37]

imagine using dirty colonizer 24/40 joints instead of glorious european 29/32😏

[@ethanmcmain9112]

The reason for the low yield is because the rate of aldehyde oxidation to acid occurs far more quickly than the oxidation of the diol to the aldehyde. Using your current method you are essentially destroying the product as soon as you form it. I’m not sure where I heard this but apparently a much better way of doing it is to slowly drip permanganate over many hours into a huge volume of very dilute piperic acid (sodium salt) containing the periodate with extremely vigours stirring. The moment you start to visibly see the colour of permanganate you have ruined the reaction. After each addition the colour should vanish within a few seconds. If the colour lingers you added too much too quickly. You could also try doing a biphasic system where the DCM extracts the piperonal into the organic phase as soon as it forms thereby protecting it from oxidation.

[@chemdelic]

Interesting. Let me try this out and see what happens!! Thank you

[@zhanchi90]

This. It's also what they are describing in a few old papers. All water based but insanely dilute, no fancy quenching solutions or periodate required.

[@rubenr4421]

mhm because it "smells better" 👀

[@mikethew3irdo]

24:25 "However, i really didnt get that high" That because you didnt complete the full synthesis ; )

[@chemistryreacts]

HAHAA!~!

[@chemdelic]

Bro😂😂😂

[@j_sum1]

Solid stuff: both the chemistry and the video production.

[@ashueje6416]

Wonderful synthesis after so long from you🎉

[@BBigg-kh7pz]

If you add compressed air to the top of your condenser, you could force the solvent over the loop for drainage.

[@SciDOCMBC]

14:16 Of course, stirring doesn't help against bumping in your case. Your magnetic stirrer is much too small for that. That is also the reason why you burned parts of your product. There was no stirring on the edge. Another small but perhaps helpful note: If you want to isolate natural products you shouldn't work with small quantities, at least if you want a pure product. Experience shows that such natural products have to recrystallize several times in order to get the product to some extent pure. Of course, you fall in love with some product. Therefore better more than less.

[@johndeaux8815]

Hmm, I wonder what a certain Grignard reagent would do to this compound? 🤔

[@williambouthillier8611]

with only an alkyl grignard, it would take you another few steps to get to the interesting part, whereas a Henry condensation of nitroethane directly with the piperonal followed by NiCl2 catalyzed NaBH4 reduction of the resulting nitro to the amine would be quicker and probably much higher yielding. That being said, you would not have access to the N-Methyl analog through this route but you could access it from the conjugated nitro product of the condensation by reducing it to PMK and from there you can acces the N-Methyl analog

[@mortlet5180]

​@@williambouthillier8611 ; I'm pretty sure "a certain Grignard reagent" wasn't referring to "only an alkyl Grignard"...

[@williambouthillier8611]

@@mortlet5180 well then would you please be so kind as to elaborate because I don't see what other grignard would get you further excpet maybe using an acetal protected one to directly get to the alpha hydroxy ketone, but you're left with that hydroxyl which isn't easy to remove at that position

[@user-ls2ff5my8f]

Can we be friends ​@@williambouthillier8611

[@Ryush806]

Lower cotton packed too dense for sure. Might even try something like inert glass or ceramic beads that are bigger than the tube opening as a support for the bottom cotton. That way you have a much lower chance of the tube plugging. Source: I’m a chemical engineer and this is what we do for our catalytic reactors to retain the catalyst but let the liquids go on through on an industrial scale.

[@chemdelic]

Thank you for the advice! I will try that

[@_shadow_1]

"I extracted the rest from Amazon, 100% yield."

[@ketsuekikumori9145]

"I seem to be cursed with orange chemistry." At least it's better than yellow chemistry.

[@LiborTinka]

it was fun until I realized there is a very simple reason why most compounds are white-yellow-orange - especially small compounds which are those often made by amateur chemists

[@jonpopelka]

We know that's you, Tom.

[@Jacob-wp8cx]

Ah yes the wizardly swirl of the flash everyone's favorite thing to do to the flask

[@GraceConyersDirtologist]

Thank you for putting your resource links up! I'm positively addicted to doing more irrelevant things to my chemistry in the lab when you're in the waiting phase of hurry up and wait.

[@williambouthillier8611]

Cotton always pisses me off when it's time to filter protic solvents, even for IPA. When you add water to cellulose, you can usually observe a certain swelling of the fibers which is thought to take place due to the packing of water molecules into the matrix. I suspect that H-Bonding interactions of the alcoholic solvents with the hydroxyl groups on the cellulose of the cotton forms a similar matrix which considerably slows down the flow. Otherwise I never had trouble using cotton filtration with any organic solvent. On a sidenote, is there a specific reason why dyou decided to go with the base catalyzed hydrolysis instead of acid catalyzed hydrolysis of the amide to the acid? Usually, it's much less efficient to hydrolyze amides under basic conditions because of the poor leaving group ability of the amine's conjugate base so it requires harsher conditions and longer reflux times which could result in some degradation of your products or reactant

[@derenjoy3r]

Would love to see the THF/KMnO4 method, also - great video! Love to see the chemplayer legacy get carried further - the knowledge and little tips from videos like these really helped me with all the O Chem I did so far

[@chemdelic]

I found the paper online and another with oxidative cleavage using O3, 5% acetone in water, and ether as an extract solvent

[@derenjoy3r]

​@@chemdelic Now cleavage with ozone, that would be even more interesting as a video IMO, if accessible for you.. Btw, are you from the EU or US or smth else? Bc I checked and even small scale piperonal synthesis is illegal in the EU as far as I can tell

[@ForgottenModders]

@@chemdelic If you go the O3 route, Make sure that generator isn't as shady as Tom's lmao. Ole death box he's got

[@michaelf7093]

@@chemdelic You can get a ozone water purifier for about 200 bucks in the states. Just hook up a tube to the output, and bubble it through your piperinic acid solution. It will take several hours.

[@Don_Soucy]

Could you share the link for that paper? @@chemdelic

[@th3r0d]

Great vid and dive into chemistry, bub. These keep getting better and better.

[@BlackRoseBun]

I know almost nothing about chemistry but thanks to you and others making informative videos like this I can safely say i could replicate this rather easily, and so I must say thank you. Thank you for making these processes/synthesises easy to access and easy to replicate.

[@timh2859]

"smells better", yeah...

[@tonyflamingo3285]

I once played around with pepper chemistry and made what I am pretty sure was 3,4-methylenedioxy-phenyl-aceticacid. It smelled super sweet but it was not very pleasent(possibly due to me burning a bit of it) it was either a very viscous liquid or a very waxy solid. I only made it so I could glout to my friends about mdma synthesis but I made the carboxylic acid because you can just halogenate it methylate the halide after whitch you just do a reductive amination to the ketone with methylamine HCL.

[@ashleyobrien4937]

no your chemistry doesn't sound right at all

[@tonyflamingo3285]

@@ashleyobrien4937 Yeah I did write it wrong. When you have the COCL group you have to react it with some methyl nucleophile. Then you should have the ketone to reduce.

[@evanlabrant5448]

As other have suggested, a paper thimble for the soxhlet would have worked much better. You don’t have to buy the expensive analytical thimbles made for soxhlets, you can fold a couple coffee filters into a cone and it works very well. Also, it helps to pre-wet very dry powders with solvent to prevent air pockets.

[@ejkozan]

In case of soxhlet and filtration cotton is packed (depending on cotton you push very slightly or even not at all), and first case too much, this broke siphoning. Also from what i remember from literature, diethyl ether gives pure compound directly. And also all this could be done directly in one step ozonolysis reaction, with high yield.

[@chemdelic]

I’m setting a video up to show that alongside KMnO4 in THF as well!

[@ejkozan]

@@chemdelichighly recommend protocol for ozonolysis in acetone with water, it directly makes ketones and aldehydes, do not need any additives. I did not do it personally but I talked with person who did. It seems pretty good for hobby lab

[@kinexkid]

I've wanted a soxhlet extractor for a while now but I have no other glassware or heating mantles or anything else. I just want to extract all the oils from my herbs in my herb garden. We have a rosemary plant that's probably about 100-150 square feet in size as well as many other herbs.

[@defenestrated23]

Steam distillation works far better for pulling essential oils than soxhlet extraction. Piperine isn't volatile enough which is why Chemdelic used it here. You can get steam extraction stills pretty cheap online (thanks essential oil foofoo types?). soxhlet are also a pain to clean out.

[@xenoxaos1]

You'd also end up with a lot of the waxy substances in the rosemary.

[@noname-80lbs]

Most labs use addition funnels instead of Shoxhlet. But you need a little labware

[@noname-80lbs]

My advice, spend some money since essential oils are a privilegie. And you must do yourself to be sure the oil is good quality one

[@captainkurt8802]

You should do a lysergic acid amide extraction and (if possible?) crystallization from woodrose seeds.

[@Sniperboy5551]

I second this

[@Bossman50.]

It’s probably one of the hardest extractions out there.

[@LukeDuncan-xi3wf]

That's got my vote as well

[@Drencromalicious]

The MnO2 is easily cleaned with Ascorbic acid. Just rinse with Vitamin C solution.

[@dantefuego]

Brown Camphor oil smells great too

[@gatergates8813]

Eugenol (clove oil) is one of my favorites

[@nefariousyawn]

​@@gatergates8813 it makes me nostalgic for 2009ish when I smoked cloves (before they were banned in the US).

[@defenestrated23]

Does it though? I've tried to locate brown camphor oil which actually smells good, but every source I found stripped out the best-smelling essential oil.

[@dantefuego]

​@@defenestrated23 i know right, the yellow and white camphor is nothing to rave about

[@sneakyBase]

I agree .

[@That_Chemist]

5:00 you are trying to filter it without having a way for the air inside to escape - you need to let air out if you want to let solvent in - smh

[@That_Chemist]

cotton plugs are totally fine when you MAKE SURE THE AIR CAN ESCAPE

[@chemdelic]

NileRed has lied to me!! Haha, thank you for the advice. Love your videos!

[@defenestrated23]

​@@chemdelic I'm going to get hell for this and I love Nigel but... his organic synthesis technique is mediocre.

[@That_Chemist]

@@chemdelic to be fair you CAN pack cotton too tightly, but you do need a way for air to escape - usually what I do when I run into this issue is I use an iron ring for the ground glass funnel, and then I keep the male glass joint half-way out of the RBF so that air can escape

[@Psychx_]

When using a Soxhlet extractor, coarser grinds usually work a tad better, esp. when it comes to draining the apparatus. I had mine clog with plant powder during first use, despite putting in cotton -.-

[@phillipmaciejewski9872]

anyone else get bothered when he let both the other stir bars solutions B and C fall into the beaker with solution A in step 3? the thought of that chaotic tumbling had me stressin lol. great video though, lots of nice colors throughout and i'm sure it smells great. gotta love when chemistry safely satisfies multiple other senses

[@toni6194]

Id be interessted in a video about turning piperonal into mdma but i think you cant do that on yt sadly. Awesome video bud hope it stays online

[@christianterrill3503]

Welcome to the watch list boys and girls!

[@harrol66]

The reason why cottonwool didn't work: you effectively sealed the system so no air could escape. Use a plastic funnel, not a glass connection.

[@geekswithfeet9137]

Im so glad to see that im not the only degenerate in this thread.... keep up the good work guys

[@dalekender422]

I just read a paper about the synthesis of piperonal, so it was really cool seeing this video. The potassium permanganate method you mention at the end was one of the routes they examined, but they """only""" got a 65% yield. The other route from piperine in the paper involved ozonolysis, but you probably don't have access to an ozone generator so I don't know if you could pull that one off. In addition to the methods that started from piperine, a couple procedures that started from vanillin were described. Also, how much piperine did you recover? It isn't very useful, but I think a video about piperine synthesis would be worth making, simply because of how inaccessible it is. It also has a pretty chemical structure.

[@maxboone8279]

Even if you have an ozone generator that's quite dangerous because of extremely explosive reaction products. You could use an acetone / dry ice mixture to cool the reaction vessel but that's quite the set up.

[@ChemicalEuphoria]

5:02 i know why it didn't filter through! it's because you didnt leave any gap for air to get out of the flask... i made this mistakes soooo many times lol 😂 now i mainly use cotton and i pack it kinda hard, it still works for me... i suggest using a narrow-necked funnel with a littoe cotton on the bottom, dont make a ball with the cotton but slide a piece on the bottom and press it with a finger. using some solvent to wet the cotton while pressing it down helps...

[@hoggif]

Soxlet has the other tube by which vapor gets to the condenser. Bottle is therefore connected to bottom of condenser that has open top. It is not closed system.

[@ChemicalEuphoria]

@@hoggif im talking about filtration, not extraction. I pinged the time mark and i said "filter", i thought that was clear enough

[@hoggif]

@@ChemicalEuphoria Oh, I did not notice the time mark. Sorry about confusion!

[@jl8n29]

Ethylvanillin might be an interesting route

[@MrNoodlyone]

From a slop jockey perspective... You should try adding the DCM, stirring it a bit, then decanting. Repeat a couple times. If the solid floats use a lighter than water solvent. Ether (after you quench the oxidizers) or even toluene would work. Dry the organic over Na2SO4. If here is a little solid floating around, a little celite can be added w/ the Na2SO4. Stirr well & let settle. Toluene has a deceptively high boiling point. It is easier to boil off than one would think. It will also azeotrope any stubborn water. Get you a rotovap.

[@MrBoho7]

This man oit uere doing gods work teaching children about the spiciest of chemistry. Never stop being the G that you are

[@chadkline4268]

Black pepper, as noted, is used to acquire Piperine, along with its isomer Chavicine, the compounds responsible for the pungency of black pepper. Piperidine, a cyclic amine that results from Piperine hydrolysis, is used with Cyclohexanone to make PCP.

[@michaelf7093]

Much cleaner product from white, not black pepper. And yes, it does smell wonderful. Instead of loose cotton in your extractor, wrap the pepper into a filter, making a large tea bag. No cotton needed, and it will flush much easier.

[@NuttyGeek]

14:00 you've got the condenser inlet and outlet messed up. The cold water should always be connected to the lower inlet. Otherwise you'll get an air bubble right at the hottest spot of the condenser at its entry, thus reducing the overal distilation effectivenes and even risking to break the condeser glass at the overheated spot with a random splash of cold water. But thank you for the interesting content of the homebrewed stuff anyway! Thinking about joining your Patreon club :)

[@Chemiolis]

Mmmm very interesting structure

[@verysmallcats1374]

"I seem to always be cursed with orange chemistry" that reflection was so out of left field it LOL

[@ChemVids-hu9jp]

The problem with the soxhlet was the particle size of the pepper + very tight packing. You can use coffee filters closed with a paper clips and larger particle size, also adding solvent through the soxhlet until it siphons will help getting the right amount in and verifying if the flow is ok through the apparatus. Great video nonetheless

[@t4steless348]

In Terms of flavor chemistry..white pepper as it goes thru a fermentation step has slightly lower piperine. Additionally typical % content of piperine in black pepper hydrocarbon Extracts (acetone/hexane) ie. Is ~40% piperine. ...cool vid 😊!

[@playmaka2007]

I understand basically zero of what's happening here but I still somehow had fun!

[@Mateo-wf1yz]

You have packed the shoxlet with to fine powder, thats why its not working correctly. A more coarse grind would have worked, also the exit hole must be clear from any blockage. But you can just mix the ground pepper and isopropanol in the boiling flask with stirring and heat for a while, that works too.

[@chemistryreacts]

This is a beautiful piece of content, I hope youtube plays nice!

[@FriendlyChemist907]

The cotton is difficult to work with. I actually have had success with undoing cotton balls and braiding them into a plug

[@SciDOCMBC]

Your Soxhlet extractor is not defective. You just ground the peppercorns too finely. The 2-propanol cannot pass through the ground peppercorns properly. This causes a layer of 2-propanol to form over the grains. You can either not grind the peppercorns so finely or you can mix in some quartz sand. In addition, the peppercorns must not be compacted in the extractor.

[@BerzerkaDurk]

19:45 - "We're now going to add some ice cubes to solution A to slow down the reaction as much as we can. We're trying to slow this down as much as we can, and adding a few ice cubes can help with this process." - Kamala Harris's speechwriter, probably.

[@chemdelic]

LMAO

[@fmdj]

Piperine is crashed out and in the fridge! I got worried for a moment as my isopropyl was a deep black but yellow when in a thin layer, very strange color (I let it reflux quite a long time with the pepper so it probably dissolved some of the dyes too). Then I didn't distill enough of the solvent to be able to crash the piperine out in the flask I wanted to use, so I had to split the liquid into 5 other containers to have enough room for the amount of water needed but it ended up precipitating exactly like in the video! Filtering will be fun. Hopefully vacuum filtration won't be too painful.

[@nicholaschristodoulou5766]

Heilotropin can be made from 1 3 benzodioxle and glyoxylic acid then oxidising the product with nitric acid

[@rdallas81]

What's that?

[@nicholaschristodoulou5766]

@@rdallas81 another name for piperonal

[@FullModernAlchemist]

Putting a bit of filter paper down there in front of the hole before putting a little cotton in there can help. Basically the cotton was plugging the hole cus it was packed too tight. It happened to me a couple of times.

[@benjamintrathen6119]

I would like to see you extract and purify cannabinoids with this method using chloroform as your solvent which does not dissolve any green chlorophyl pigment. Alternately could use another solvent like petroleum distillate or something else but they don't have this effect on chlorophyl.

[@fishingd5962]

I wish there was a video about extracting cannabis resin into diamonds from his lab

[@vaportrapwave2658]

The siphon probably didn´t work because your pepper was packed quiet dense. And your cotton filter didn´t work because of the overpressure build up in the flask you filtered into. The air in there counldn´t escape. hope this helps. have a great day :)

[@noname-80lbs]

Not probably For sure its too fine

[@vogelvogeltje]

I love when my solution gets more O P A E G

[@plokoon4217]

Nice extraction and synthesis, have you ever thought about making citrulline?

[@platinumwaiter]

I think a lot of yield was lost with the extraction. Seemed like the aqueous layer was a fair volume and usually when adding in solvent to extract you want to use about 70-100% of the aqueous volume. Usually also extract three times, maybe more if you really want some extra stuff (although if you pull in 90% of your desired compound into the organic layer you should have 99.9% of it after 3 extractions)

[@intergalacticmeow]

All right, the 90s are back🎉 Time to get my neon rave boots wit the jamiroquai hat

[@rdallas81]

Lol

[@science_and_anonymous]

Bringing back good memories of chemplayer...

[@science_and_anonymous]

Also, the reason for the prevention of the flow in the Sox. Ex. is due to you pressing the cotton down too hard. It should be very gentle and loose. Imagine the consistency of a cloud, and start from there.

[@fastbre4ker]

i somewhere saw an prep where Mg/MeOH reduced the double bond of an piperine derivate on the 3,4 position, oxidizing this alkene would lead to the phenylacetic acid, if you want try it out :P

[@pyrotecx123]

Use celite and all of your filtering and soxhlet woes will be solved. Even better to vacuum filter over a bed of celite. This stuff was a complete game changer for me!

[@chemdelic]

I’ll need to get some!

[@PotooBurd]

This is so informative!!! Fantastic video; I love this kind of content!🌻🌼🐝

[@kachniash3431]

You sound like Sam o’Nella’s older brother, great video

[@yungtrashlord]

what is with this law and order sound effects 😂😂😂i fucking love it

[@christopherleubner6633]

The soxhlet effect is caused by a syphon. In order for ot to work well you need to have a gap between the filter and the wall. That way there is enough fluid to start the syphoning and flush the tube. 🤓❤

[@dpasek1]

If you use an extraction thimble, the siphon will work properly.

[@JustAnotherAlchemist]

One is generally supposed to use a extractor thimble with a soxhlet extractor. ... Also, you *MAY* want to get ready to set up on another video hosting platform soon as one doesn't usually have to cross the line nearly as far as you have to get the boot from KZbin.

[@t4steless348]

Also. Heliotropine or just shortened to helio. Is used alot in marshmallow type flavors.. as well as the obvious cherry-garcia-esque vanilla icecream almond vibe... and perhaps even more commonly used in womans fragrance.

[@SlimothyNate3218]

My guy skates the fine line of legality 😂😂

[@fademusic1980]

every now and then, I hear you slip into nile red's speaking style

[@dyllan559]

"Making a watchlist chem because i cant buy it!" *Uses potassium permanganate during synthesis as if its not also a schedule 1 chemical*

[@Louzahsol]

I purposely watch demonetized content because I refuse to give KZbin money to not have ads

[@zekiz774]

Yeah sure... because it smells better. Doesn't have anything to do with a precursor of a certain drug that looks kinda similar

[@chemicallyfired4743]

The reason why the solution could not filter is most likely due to there being a fixed pressure in the flask because the joint was sealed. Lifting up the funnel would most likely fix this.

[@oligold4939]

Use a soxlet filter capsule available at specific shop chemistry is a exact science

[@quokofumi5653]

You could add saturated salt solution into the dcm/water exctraction to get little bit more product