NileRed - 2014-06-25
In this video we will be making butyric acid by oxidizing 1-butanol (n-butanol) using KMno4. Chemicals: - 6.2mL 1-butanol - 14g KMno4 - 1.5g sodium carbonate - 2M H2SO4 - Diethyl ether - 90mL 3% H2O2
You should mix cadaverine and the butyric acid
I was thinking of it, but no thanks! haha
+Classical Liberal Do you realize how incredibly disgusting and unbearably stinky that would be?! INSTANT gag and barf city for even the strongest stomachs!!!!! lol
Ahh i think thats the smell of massacre
And skatole.
When watching this video, you can literally smell the odor of butyric acid.
5:07 the color of Vomit when stomach is empty
I wanted to ask--are you on science madness?
haha still nothing!
@Nile Red That's weird, it's not letting me send it again. Could you try sending me a request?
I can't find your account! Do you know the account name?
@NileRed So are you in their group chat?
This saga never got a proper ending
I'll never forget the time that my high school chemistry teacher brought butyric acid into the classroom. It was stored inside a glass jar, inside another glass jar. He only opened up the outer jar and it stunk the whole classroom out. He knew what he was doing.
I knew a guy who told me about this stuff. He called it the plague. He used to do mayhem like clear out malls and stuff like that. Or to get revenge on someone he would use butyric acid. This was 25 years ago. I stumbled onto this and the memories came back. Think times Square, statue of liberty etc
This synth worked great for me, and I modified it it to make Valeric acid from 1-pentanol. I got a really good yield though. About 80-85%
Wow!
Keep updating :-)) love watching organic synthesis
3:05 The MnO2 remaining in the flask is washed twice with about 50ml of water.
The MnO2 is washed twice with about 100ml of water. 3:17
+WaffleSmoof haha i have no idea how that happened. That is clearly messed up, ha,
My response is a little late, but here the explanation. He first washed the MnO2 in the flask with water to form a suspension that could be transferred into the buchner funnel. Then, he washed the MnO2 in the buchner funnel with water to pick up any butyric acid left in the MnO2.
This stuff is sold at the cost of 25$ per 450 ml. It's so expensive.
Interesting, why was such a massive amount of Kmno4 used ? Perhaps just to make sure all 1-butanol was oxidized quickly
Butyric acid is actually produced from dietary fibre by bacterial fermentation even in humans, and may be the mechanism for why a healthy microbiome in the gut might have anti-inflammatory and other health benefits, colonocytes in the colon actually metabolise almost exclusively butyric acid (which is a volatile fatty acid in biochemistry terms) only metabolising glucose under stressful conditions where very little butyric acid is produced (some of the butyric acid reacts with ammonia, or sodium bicarbonate to produce ammonium butyrate, and sodium butyrate which is absorbed and is pretty much the same as butyric acid, which is why in cases of liver failure they might use fibre to generate butyric acid which mops up the excess ammonia that is formed from impaired urea cycle.)
Nice youtube channel overall. Really cool!
3:18 you said it twice lol
Your video was referenced in Project Veritas' latest video.
glad im not the only one who noticed
And an Alex Jones thumbnail
Imagine my surprise as a pretty big Trump guy when I saw my favorite chemistry channel pop up in relation to this shitshow.
Hmm another way of removing MNO2 is by centrifuging. PP tubes with the Mno2 sinks as a solid pellet easy to do.
Does the KMnO4 oxidise the alcohol selectively at the 1 carbon, or is it random?
How corrosive is this? I heard butyric acid is healthy. Can you make some caprylic acid as well? I heard it is supposed to smell like goats. I've never seen a goat, so i don't know :3
Fun Fact: The Ethyl-Ester of Butyric Acid smells like Pineapple. Very pleasent smell. I did that a few years ago, it was so absurd to first smell vomit, then suddently pineapple.
I miss those kind of videos... =(
0:48 ah no. I hate potassium(or kalium) permanganate. That purple stuff gets every where. And it ruins all the glass work. Cleaning is going to be hell
From a guy who can do vomit on command i must say i am disentisized to the smell
Hello Nile, I've replaced permanganate with dichromate in sulfuric acid solution (just because I've plenty of potassium dichromate). After addition of n-butanol my solution heated up and I started to smell the butyraldehyde that has a low boiling point so I had to set up a condenser and a cool water bath. Anyway, the presence of aldehyde meant the reaction was going fine. Due to high solubility of chromium sulfate and, surprisingly, different butyrates, I had to carry out multiple extractions of butyric acid using xylene (I read butyric acid is miscible with all organic solvents, and again I had a lot of this compound). Before the extractions I acidified the solution with sulfuric acid to get pH about 1 to surely hydrolize any butyrates.
The question is why my extract is purple-colored. I tried to mix it with some another solvents like alcohol and alcohol-water mixture, but the colored compound stays in the xylene layer. I thought about using TLC, but I don't know how to make butyric acid's spot visible on paper. Also I tried reacting the alcohol-water mixture I'd previously got with alkaline solution and got some white precipitate. Almost dry precipitate smells definitely like vomit, so I suppose this is butyrate and thus I've successefuly made butyric acid. But there is the second problem: I have no idea how to get pure butyric acid from xylene solution with an acceptable yield.
So, do you have any ideas on the topics I've mentioned?
DevilsVideos1 using pressure n temperature to separate them as both have different boiling points
i was making esters at school using butyric acid. the smell lingered for days...
...It also CAN Be made by sliceing up a potato, and leaving the pieces in a closed jar, filled with water... Afther about two, three weeks, sniff it.!
btw, the time is depended on the temp, so check it better often.!
First! This is a really cool video.
Thanks!
Is ether really necessary or can I substitute it for some other organic solvent (hexane, toluene) ?
I wouldn't say that ether is absolutely necessary. It is just known that butyric acid is quite soluble in ether and I was following a procedure that called for ether. I don't see why hexanes wouldn't work or some other organic solvents wouldn't work.
We used this stuff in Chem for a just-for-fun lab making pleasant smelling esters. They smelled great. This stuff, on the other hand, is straight up NASTY.
The peroxide will also be decomposed by the MnO2.
Is it possible to use hydrogen peroxide instead? Thanks
can i have a sepretory funnel ??
Hi Nile. Im getting mad trying to find a mechanism in wich I can see how the permanganete attacks the primary alcohol to oxidize it two times. Do you know something about that? Also, in theory, how many equivalents of permanganate do you need for an alcohol equivalent?
Thank you¡¡¡
+Nation Of Our Hobbies I am honestly not too familiar with inorganic mechanisms of oxidation. Also, it is late here and I am lazy, haha, so i am not going to calculate it myself. If you want to know the equivalents, just calculate how many mols of each I used. I really dont remember what it was off the top of my head.
When I was in school, a buddy and I put a dead squirrel in the ventilation duct as a joke, but, I think this Butryric Acid would have worked equally as well.
Sounds like you might be a psychopath
Psilocyb do not be mean
I wonder how much I need to put on my toast. You'd better drink your morning coffee first or you might just end up throwing up all over your kitchen :s
Home made blood
Nile: You apparently are bigtime into chemistry and have a lot of knowledge in it and have a lot of equipment for it. I am curious if you have a degree in chemistry or went to school for it in some way.
+tall32guy I was a biochem undergrad and a chemistry graduate student for a while.
+Nile Red cool there friend!
where does one find 1-butanol?
If you want your Butane in liquid state or gas phase you need Butane from gas buttle. For liquid you need to release it from the buttle winter when you are sure the temperature is below -2 celsius. Than you can chlorinate it: CH3CH2CH2CH3+3CL2>CH3CH2CH2CCL3+3HCLAfter the Chlorination you should react 1,1,1 tri ChloroButane with 3 mols Sodium Hydroxide to make Butanic Acid: CH3CH2CH2CL3+3NaOH>CH3CH2CH2COOH+3NaCL+HOH.You can do it in gas phase though I hate gas reactions cuz right steiometry is done a bit tougher.
If you still have pink left in your first flask, why not just add more reactants? Why add h2o2?
I need to sleep but then I saw the title.
Lmao same
+Nile Red Was the sodium carbonate really needed? I mean doesn´t potassium permanganate ALONE react with 1-butanol to form potassium butyrate?
I think it keeps the solution alkaline
It's also in rotten potatoes. thats why leaving a potato in a bucket of water, then leaving it in someones bed is really funny (it also has several other sulfides and sulfates that cause it to smell like gangrenous wounds/rotting flesh)
Yuck!
Headshotted718 that's not funny it's fucking sick as in you are sick in your head.
How do you know when MnO4- gets reduced to Mn4+ or Mn2+? Is it not reduced fully because you didn't heat it?
+slateflash no, it depends on the pH-value: in an acidic milieu permangante is typically reduced to Mn2+, in an alkaline mileu it is reduced to MnO2 (Mn4+).
@196Stefan2 Thanks!!
almost though you stopped making videos but nevertheless that was quite interesting
He's back stronger than ever. His new stuff is great.
I remember being a stupid high school kid and taking a bunch of small concentrated acid vile's from the chem lab. One of them happened to be Butyric acid. That was then the biggest mistake of my life. the smell was so concentrated I had to throw away my clothes, backpack, and anything that came in contact with the CLOSED VILE. room ended up smelling like vomit for days. Oh yeah, and it got in my dads truck when he picked me up from school. he was really happy about that lol.
Now i know how to make more of this stuff! Thanks!
Where did you get butanol?
hardware store.
Fermenting a nutrient to form butyric acid does seem to be the cheapest and easiest way to get butyric acid, but how would butyric acid be extracted from a fermented source?
why does old soap smell like vomit
You sound slightly sad in these old videos. Probably it was before the big success :)
Hi Nile, I am trying to create Butyric Acid too, but due to a limited amount of materials I have, I may have to make do. Can I still get Butyric acid if I just use Sulfuric acid and KMnO4 (and also 1-butanol)? I am planning on doing reflux and if you happen to know how this works, I would love to know an outline of the procedures.
electrorganix - 2017-01-15
Hi Nile, I used to work for a flavor company in Chicagoland area, used to handle 55 gal. drums of butyric acid, capric, caprioc acids, pyruvic acid, glacial acetic, also cinnamic aldehyde, diacetyl, and a lot of other stinky chemicals. In my opinion butyric acid is one of the worst when trying to wash it off hands (caution: it burns skin), it seems to be somewhat oily and skin soaks it up like a sponge. The "vomit" smell can linger for many days before it finally goes away. Thank you for great videos.
Salvatore Bologna - 2018-06-08
I work in a food manufacturing facility. Buytric acid can be used to mimic the flavor of butter and cheese. Sometimes the "natural flavor" you see on food labels are these compounds. When at the movie theater you smell buttery popcorn. Buytric acid is just one of the many compounds present, diacetyl is the main. In e-liquids/vaping a flavorist wants to make a strawberry cheesecake flavored liquid. Buytric acid could be used for that sourness. It's just one of the back notes in cheesecake. We are speaking 1ppb. Or whatever the flavorist is looking for in addition to the flavor.
Patrick Casey - 2018-11-28
A. Neufeld Hershey’s chocolate bars
Tulanir1 - 2018-12-18
@A. Neufeld Butyric acid can for example react with ethanol (a very commonly produced compound) to form ethyl butyrate, a sweet- and pleasant smelling ester (often described as peach)
C3H7COOH + C2H5OH --> C6H12O2 + H3O+
Chris D - 2019-01-02
electrorganix- hey sorry I know this is an old post but this Hershey’s chocolate thing is really bothering me. Do you notice the butyric acid in this product? I never had and I’m thinking some people might have a strong negative reaction to very small amounts of it while for others, small amounts of it taste pleasant.
spiderdude2099 - 2020-04-30
It is very lipophillic so just imagine VERY strong vinegar that soaks immediately into your skin. It’s terrible