ฝัง
- เผยแพร่เมื่อ 21 ธ.ค. 2017
- Today I'll be making glowing stuff again, but this time I'm going to try out a more environmentally friendly method. The prep for this video uses wintergreen (methyl salicylate) instead, which I made in an edible chem video.
In the previous video, the active chemical I made was TCPO. This required 2,4,6-trichlorophenol as a precursor, which is damaging to the environment.
Procedure: goo.gl/ikYdRt
Related NileRed Videos
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Nile talks about lab safety: • Chemistry is dangerous.
Music in credits (Walker by SORRYSINES): / walker - วิทยาศาสตร์และเทคโนโลยี
all I'm getting from this is NileRed sleeps for 24 hour periods
Ethan Van Goethem You don't?
all I'm getting from this comment is that +Ethan Van Goethem doesn't know how language works
TheMrVengeance so he didn’t notice it was still glowing the entire day? Just went 18 hours after waking up before looking at it, also ur a weeb so shut up
No, because a lot like Tritium vials, this stuff probably looked like a bottle of yellowish water in the sunlight. Also, he probably has to work during the day, unlike some people...
Ethan Van Goethem - Thanks for proving my point.
He said he wanted to stay awake to watch the glow disappear.
Then he said he was happy he didn't, because it still glowed 24hr later.
That doesn't mean he slept all of those 24hrs.
Nor does it mean he didn't notice it still glowing when he woke up.
So thanks for proving you don't understand language, I was just joking initially, but since you had to go and be rude....
It's interesting that wintergreen is part of this reaction. If you put a wintergreen Life Saver in your mouth, look in a mirror, turn off the lights, and bite down on the candy with your mouth open, you'll see little sparkles of light. Apparently the static electricity generated when the candy crunches will excite the wintergreen, which then gives off brief flashes of light. No other flavor of candy will do this.
Happy Holidays!
Its also important when making wintergreen sparks to breathe through your teeth for a bit and then bite down once theyre nice and dry
@Yung Colgate triboluminescence?
I thought that was a piezo thing. I didn't know it was static.
Nerd
* Butdontaskmebb * nerds candy will not work.
Tasting impure wintergreen? No problem. Using it for synthesis, uhh no I think I'll have to make something more pure.
Mykel Duso yeah hahahahha i wanted to comment that. You would guess its the other way around
Yeah well the impurities were probably mostly food-grade.
Reagent-grade is actually higher in quality than food-grade; a lot of contaminants that can ruin reactions are fine in food-grade.
@@KnakuanaRka Indeed lab grade and food grade arent even neighbors.
Lmao
Back when I was in high school, a friend of mine's dad has some huge bottles of the same stuff used to fill glow sticks. We made a 2 liter bottle of the stuff up. Then we heated the bottle up, it was glowing so bright you could see clearly in the room with no lights on! It was definitely a fun time, especially because we were also doing some experiments with lysergic acid diethylamide at the same time! The 90's were a great time to be alive!
Gary Carone sounds like a fun 90s time
Gary Carone Not for Serbs or russians.Still there were many advancments in technology
awesome fun with LSD in 90's xD
RAVE ON!!!
lysergique acid ? heh i see what you did there
you: "it's a flavoring agent for things like candy and gum-" [shows lifesaver package]
me: immediately smells strong mint despite not being near any of it
brains are weird
Brains are weird.
I was thinking the same thing! I DO have a peppermint essential oil and a room spray, but haven’t used either in some time. But my brain still smells it right now just thinking about it.
just you pal
i can feel how it burns my sinuses just by thinking about it
Synesthesia.
"Glow Stuff"
u suck
same
G L O W S T U F F
bok is not me is another random cat
I am the 222 like
8:55 *Nuka Cola Quantum*
Hydra Overray You mean quartz? Since quartz is the green one, whereas quantum is tonic blue...
domonator5000
no, quartz is the color of mtn dew whitout
Rc glow.
Forbidden Nuka Cola Quantum.
Yep
The vacuum filtration is still magical.
"Possibly carcinogenic" Focusing on the "Possibly" that's how you know that you are doing some really odd things compared to most at home chemist's.
Chloroform IS carcinogenic.
"Enviromentally mean"
D:
Highly technical term, too advanced for you
IDWpresents: Insert Rick and Morty copypasta.
You made Pyridine? Willingly? You are far braver than I, Dr. Red. I haven't had the need to deal with it and it's insupportable stench since the mid 80s, and it could probably wake me from a dead sleep.
Im not a Dr, but yeah, i did it willingly. It was less than pleasant
Ive worked with it some time and IT wasnt very unpleasent.
NileRed
Oh, but you’re MY doctor. ;)
Holy sh*t, what were you even doing that you needed enough chlorine gas to turn your house into a WWI battlefield?
@@elephystry Bruh wtf
Possibly carcinogenic? Is there *any* chloro aromatic molecule that's even remotely good for you?
Good for you? I don't know. But not all are carcinogenic. There are plenty of pharmaceuticals that are chlorinated on an aromatic ring that are, as far as we know, pretty safe. Along with some pretty safe chlorinated recreational drugs, like 2C-C. Honestly, it's better to have a molecule chlorinated on the aromatic ring than to have it chlorinated on an alkyl chain or something; the latter would almost CERTAINLY be carcinogenic.
+Mexi Chemia I wouldn't go that far. There are plenty of halogenated pharmaceuticals. Halogens aren't ALWAYS a safe substituent, but they sometimes are. Fluorines are the safest, considering the fluorine-carbon bond is so stable, you can usually use a fluorine safely even in cases where a chlorine or bromine would be bad. And the aromatic ring is certainly a better place for them than anywhere else; they'd be WAY worse on an alkyl group, pretty much invariably carcinogenic or toxic in some way.
+Mexi Chemia Very true, at least for the most part, but that's certainly not "99%".
Benzene is literally cancer sauce, so it's not suprising if you chlorinate it, which like with chloroform makes it even more cancerous.
How about diclofenac? Two chlorines on an aromatic ring, and it is reasonably safe for humans, it is quite widely used. There are also some others like bupropion, clindamycin (an alkyl chloride!!), clonazepam, though that last thing is so potent at its pharmacological target that the dose is super low, like 0.5 mg low, but the others have much larger doses. Do not forget thyroid hormones either (yes, its iodine, but still). So in fact there are a lot of chlorinated compounds that are good for you, if you dose them appropriately when you need them.
Loving the way that you can tell which chemicals Nile’s made himself vs the ones he had to buy based on which ones are just in little blank bottles/containers with a label from a label maker
y'know that footage of you pouring the glow fluid back and forth would make a solid short outtro. throw in some music and bam!
Throw an eye painted green attached to a string in there and suddenly it's jacksepticeye
Hey NileRed, I have a question. When I was a kid, I was at a party once where there were glow sticks. Some friends and I broke one open, and there was an incredibly awful smell that came from it. I couldn't even describe it. It was just that when the fumes hit your nose, you gag and have to run away, almost vomiting. I had thought it was just the nature of the glow chemicals, but now it seems like maybe it was an additive they may have put in the sticks to keep kids from breaking or eating them? What do you think?
I think it's an additive. Ive broken them apart many times and even used to put the liquid in my mouth when i was young and dumb. It just tasted like solvent.
That sounds both stupid and awesome. Thanks.
NileRed "It tastes like solvent". Doesn't each solvent have It's own taste? I wouldn't want to be the one to check, though.
Either way, if it was a phthalate based solvent, the most dangerous thing about it is probably the cancer causing chemicals and dyes.
@@NileRed I don't like the fact that you know what solvent tastes like
I was taking a bath with glow sticks, they broke. I’m surprised I don’t have three eyes
I heard of this radium stuff and supposedly it glows pretty well.
It's radioactive ☢️
>low yield
must be nilered
:(
:D
Dude works to clean.
Shit needs some dirt in it
DarkIzo he always spill some of the starting materials so its not a surprise
>low yield
Must be another Irish potato famine.
ive binge-watched nilered for 2 years now, old and new. and yet, every time I'm recommended a video its one I've never ever seen and its always 3+ years ago
Very good video!
Funny how no replies lol
@Harshal Gupta lol
I want the 36 hour live stream where you watch a glowing bottle
10:09
You went to sleep and woke up 24 hours later?
lol, i meant its a good thing i didnt wait all nice to watch it disappear
I guess ethyl acetate did the 24h sleep magic :P ...anyway I love that sweet smell - is it possible that body metabolizes ethyl acetate into ethanol and vinegar ? Then it would be pretty safe solvent.
Yes, it is indee a pretty safe solvent. I think that under acidic conditions the ester bond is hydrolized, and then the products must be acetic acid and ethanol.
Oh, so that's how they produce 'cooking wine'. Drink ethyl acetate and pee in a fancy bottle. ;p
yes it does, the body is full of esterase enzymes that hydrolyze esters, a lot of drugs actually use this trick to modify the effect length or absorption from the gut, they make an ester out of the drug, it gets absorbed, and eventually cleaved to release the active form of the drug
2:16 "why are my yields so low?"
If you reply I will scream in my house
Lol hey
@@NileRed gottem😂😂😂
2:05 - Processo de destilação para purificação
Descontinua o processo quando apenas resta um pouco, o que é assumido ser apenas impurezas
Iniciando as reações
2:24 - Adiciona 50mL de THF, 3.85g de Methyl salicylate e 4.97g de pyridine, nessa ordem.
Ps.: A pyridine estava relativamente velha, o que tornou sua coloração mais amarelada, mesmo que isso não influencie no processo
2:41 - A abertura do frasco é tapada com um frasco menor e começa a Mistura Magnética
2:48 - processo de resfriamento pois a reação gera bastante calor. Pra fazer isso é realizado um banho gelado
2:58 - Após o processo de resfriamente estar finalizsado, é adicionado, em pequenas porções e bem aos poucos 1.6g de oxalyl chloride. Essa adição dura por volta de 15 minutos.
A reação é entre 1 de Oxalyl Chloride e 2 de Methyl salicylate, gerando MCPO, mesmo que gere também como subproduto Hydrochloric acid.
o ácido não dura muito, já que reage rapidamente com a Pyridine, um químico básico. Eles geram Pyridine Hydrochloride, um sólido que se prende aao fundo.
E, por fim, o produto desejado é solúvel em THF, fazendo o mesmo continuar em solução
3:45 - Retira o banho de gelo e continua misturando em temperatura ambiente por aproximadamente uma hora.
3:47 - Adiciona 50 mL de água e continua misturando por mais 15 minutos
Ao adicionar a água, o solubilidade do MCPO é reduzida, mas a solubilidade do sub-produto, pyridine hydrochloride, fazendo com que os mesmo troquem de posição. O precipitado branco agora éo MCPO
4:12 - Processo de separação por filtro a vácuo, mesmo que a filtração também poderia ser feita via filtro por gravidade.
4:21 - O frasco é limpo com um pequena quantidade de água para ter o máximo possível do frasco.
A água também serve pra retirar qualquer pyridine hydrochloride que tenha sobrado no MCPO
4:30 - A bomba à vácuo é deixada funcionando por mais 15 minutos para secar o produto o máximo possível
4:37 - Tudo é transferido à um watch glass
5:22 - 100 mg de MCPO são adicionadas à um frasco pequeno, seguidas de 5 mL de ethyl acetate.
5:33 - Mistura os dois um pouco manualmente
5:35 - Adiciona 20 mg de corannte (BPEA) e 20 mg de sodium acetate
5:41 - Adiciona algumas gotas de 30% de hydrogen peroxide e isso inicia a reação.
O ethyl acetate e o hydrogen peroxidade não se unem tão bem, o que faz com que, para ser de fato iniciada, a mistura precisa ser agitada
6:01 - A reação ocorre. O MCPO e o peróxido geram 1,2-dioxetanedione, mas como sub produto ele também re-forma o Methyl Celicilate.
Great videos NileRed greetings from a chemistry fan in Honduras
Environmentally harmful chemical: *exists*
Nile: I don’t fucking think so
Oooo, that HAD to smell so nice while making it! LOVE minty scents!
seriously so cool that you tried this. it was so satisfying to hear that an impurity was insoluble, rather than both being the same solubility and having to do an aqueous workup or something! you rock, cute chemist.
thanks, im glad you liked it!
I'd love to see a video of you making and eating ATP (Adenosine triphosphat).
Why? Just... why? As you probably already know, adenosine triphosphate is stored energy for cells. It’s in all living things, and there’s a lot of it in grains. I don’t think you are going to get the reaction or interest you are hoping for. The most interesting part would be extracting it. Eating it would be the equivalent of eating grain, but without the nutrition and flavor.
Making glowy stuff and saving Earth-Chan, best video you'va made yet
Merry Christmas from Australia, NileRed!!
I thought I'd let you know that I'll be releasing photons from the quinine in my Gin & Tonics throughout the silly-season via chemiluminescence using a blacklight and/or my 405nm laser-pointer.
Have a fun time Dude! See you in the New Year. 👍
Yeh. G&T under UV light. I recommend Plymouth, or perhaps Tanquerey.
Boodles
alternative title: turning mint into mint juice
Turning mint into mint flavored light up sketchers juice
The vacuum filter...my favourite apparatus..😂
Love your content, keep it up!
Tbh mint flavour has always been kinda glowy looking to me. This is just the next natural step: flavour you can see in the dark.
I was looking for more on glo sticks. Very interesting. Great project!
Phthalate esters are easy to make, I made a video on making diethyl phthalate from ethanol and phthalic anhydride. I'm sure you have the chemicals, so you should make a video comparing TCPO in diethyl phthalate to MCPO in ethyl acetate.
Does that mean that the commercial glow sticks are are contributing to environmental damage or do some likely use this alternate chemistry?
Almost definitely environmental damage. Most dont break open though, so I imagine most stay contained.
but, you know, outdoor parties, a few glow sticks get thrown into the woods...
I'm not proud of what I saw in the woods, done with those glow sticks but I am sure glad none of them broke (ya know, environmental damage and all).
Is the actual amount super toxic or does it have retention like DDT?
John Di Francisco what did you do with the glow stick you fiend!
It’s really interesting to me that the liquid, while flowing between containers, doesn’t seem to glow very much at all.
Nice and Merry Christmas nilered
Any chance you could do a tour of your lab/set up? Would be really interesting
Just to ensure you did end up seeing, he put one out a bit after this video came out.
@@CraftQueenJr yes of course, i have seen the video :)
Thank you for these beautiful pictures... ligtning is a magical phenomena !
Merry Christmas! Keep it up. Greetings from Austria. ^^
5:50 that pleasant keyboard noise.
oh no
Nilered marry Christmas dude
Next on Edible Chem: Nuka-Cola Quantum made from MCPO in a nontoxic solvent (maybe ethanol? or maybe something inert) using a food-safe oxidizer and fluorescent dye.
Seriously though that would be really cool, and the reaction products would most likely taste nice and minty...think of how great that would be at a party!
Lol, i am not sure if its possible to make an edible version.
While the math with LD50s for the breakdown products and H2O2 works out in favor of one of those little one-shot liquor bottles as the scale, the ester itself could be highly toxic. I have not yet found any information on it so I wouldn't try it even if you actually could come up with a way to do it. Cool video though man, keep up the good work!
Add to that, that LD50s aren't the only thing to worry about. You obviously don't want to be drinking a lethal dose of anything, but you also wouldn't want to end up with some kind of weird liver/kidney disease in 25 years time or go blind or something.
have the same thought about nuka)
TheMrVengeance Most definitely! Chemists already have enough to deal with in terms of cancer rates, a diseased liver or kidney (probably kidney if the ester is broken down into oxalic acid in the body) on top of that is not something worth the risk...but if it ended up not being at all dangerous to human health, glowing beverages would be rather cool...I guess we will have to stick to tonic water and a UV light until someone is stupid enough to drink a glowing liquid and lucky enough to have no ill effects even at a large quantity!
Happy holidays Dad!
you seem calm in this video
hello, Nile, after your vid i synthesized few grams of divanilyl oxalate by similar method - Vanilline + thriethylamine + oxalyl chloride in anhydrous THF, it is not very soluble in organic solvents and most of it precipitates from THF during the reaction, then i diluted reacton mix with water and filtered it out. I tried this in glow stick reaction and it was pretty bright, i think you should try this too and compare with TCPO and oxalate from methyl salicylate. It should be brighter than the latter.
The wintergreen mints spark in your mouth when you chew them i just put the two and two together of why it does that with this video. Love your channel. Thanks for all the awesome content.
I used to put my glow sticks in the freezer when they got faint. They would significantly light up more. I looked it up just now, it says that it slows the chemical reaction. I’m still not sure why they got brighter but I think it might be because possibly the rate of glow decay thingy was slowed as well, possibly making it possible to make the reaction product more concentrated. Apparently there’s been no studies on it(according to a 30 second google search). Anyway, I’m not a scientist but I think that’s pretty cool.
One of the Inorganic Chem. Working groups at our university works on OLEDs and they have a chamber they call the "light room". It's 4m² and covered wall to wall with racks and shelves, each loaded with vials with fluorescent compound. You can turn off the normal lights and switch on the UV lamp and suddenly the whole room starts glowing in all shades of red, blue and green. Pretty cool stuff
A very illuminating video... :P
"its a good thing i went to sleep, because 24 hours later"
NileRed has chemically invented hibernation in humans
nilered's the kind of guy to making glowing bubblegum flavored concentrated cocaine from 4 liters of coca cola
Hey NileRed, could you do a video on testing the mercury content of tuna? Thanks!
Also, whats the meaning behind your channel name?
p.s. I'm going to ask Cody's Lab to do the same on his next video, I'd love to see both you guys do that!
hmm i could try to figure something out. Might be cool
Thank you, I'd appreciate it. I imagine the quantities extracted would be minute, but from what I've seen in some studies, significant to health.
NileRed Send me a sample, our lab is equipped with an ICP-OES instrument, I'll run it for freesies
You can chill them to make it dimmer but glow for longer or heat it slightly to make it brighter but shorter
Pretty cool!
The more I watch these, and the more I study chemistry on the side, the more convinced I am that alchemists were correct.
About what?
Would it be possible to crystallize the elements that react to create a slow releasing long last chem light?
I just saw a luminous blue cloud in the mostly clear night sky with the crescent moon off to the side unobstructed, it was beautiful, I've never seen that before.
Interesting. I found this same paper a few years back and also tried to make MCPO as an alternative for using TCPO in glow stick demonstrations. I ended up settling on sticking with TCPO after trying it just because the initial brightness of TCPO vs. MCPO looked better in a classroom. I was using diethyl phthalate as my solvent. If I remember right, the MCPO worked fairly similar in ethyl acetate and the diethyl phthalate. The MCPO may have gotten a little brighter in diethyl phthalate, but its hard to say for sure based on comparing a video to memories from three and a half years back. TCPO is where I saw the most difference between diethyl phthalate and ethyl acetate.
I think I may give it another shot to experiment with the MCPO. If we knew more about the kinetics of this reaction, it may make it easier to adjust the recipe to make the MCPO have a brighter punch.
Good video, thank you
I would recommend trying dibutyl phthalate as a solvent in both cases... Worked great with TCPO.
"Just because I figured it would look cool" lol my kind of reasoning
Nile really love your videos. Was wondering how dangerous the other chemilumeniscient solutions you made are mainly flouriscien. Was thinking about making glow in the dark bubbles, but friend was concerned over toxicity.
I've made the chemiluminescent out of vanillian. came out good
Asprin to mint flavor, mint flavor to glowing liquid, the saga continues!
I bet the TCPO kicks out the dioxetanedione faster than the MCPO. Difference between electron donating groups like chlorine ( TCP) and electron withdrawing groups like a methyl ester (methyl salicylate). Nice work.
How have I never seen this!
Nice video. Can you synthesize antibiotics? Also a video on high valent iron would be great.
I filmed sulfanilamide a while ago. I have just slacked on testing it. Ill get my act together soon though
NileRed how are you going to be testing it? In-vitro with a microscope camera?
like hexavalent iron or something? thatd make some powerful oxidizers tbh
Atropos yeah. Ferrate ions as well as some exotic iron chemistry.
Bit late to this thread, but the reason your camera didn't pick up the output of light very well is because the aperture of the lens is too narrow.
A stock lens for a digital camera has a focal ratio of f3.6-f5.6, which doesn't allow a lot of light to hit the sensor. For dark scenes lit naturally (or chemically) I recommend a prime lens with an aperture size of f1.7 (the lower the focal ratio, the more light goes through to the sensor), though this can be expensive. The cheapest option you'll have for that is in analog lenses, which you'll need a mount adapter for.
Asprin -> Mint Flavor -> Glowing Liquid
I need to know if there is a way you can make a glowing liquid that is safe to drink without using a black light.
I know a spot at a children’s camp i work at during the summer where winter green grows
glow sticks are pretty good:)
Great video! How do you shoot your videos in the dark? They are all super sharp and have no grain. What is your equipment, setup and camera settings? Thanks.
Molecular sieves are the best though! However, to be fully activated, they need to be heated to at least 200C for 8h or more under a vacuum of at least 0.05 mbar, and then stored under nitrogen due to them being extremely hygroscopic. In the lab, we use them to get solvents down to less than 1 ppm water.
Considering your oxalyl chloride was not stored under nitrogen, that was probably impure too. Maybe adding a slight excess would have been enough to boost your yield.
Yeah I seriously doubted the statement that the solvent wasn't dry, even if he didn't properly activate the sieves. 1ppm is seriously overstating it, it's way under that by like an order of magnitude at least. Our lab has a Fisher titration apparatus and we looked at water content of acetonitrile and methanol - methanol contained way more, of course, but both were reasonably anhydrous.
Hey, it would be awesome if you could make a video on all of your lab equipment!
Just to ensure you saw, he did release one of his current lab a few months after this video, and I’ve seen a couple references to a new one coming soon.
Mix them together and see how bright it is
ASPRIN GLOW STICK
Hey Nile, since you like odors, you should make propionic acid. I hear it has a rancid, body odor-like smell.
Making that fire dope
Can fluorescein work as a fluorescent dye ? It would be much easier to get them the other fluorescent dyes : ) And also , is there any other solvent that could work for the sintesis of the MCPO , instead of THF ?
Hello Nile Red you have a really great channel....heres a thought can you extract myristicin or elemicin from whole nutmegs?
I'd be interested to see if you could make glow in the dark or UV reactive bubble liquid.
@NileRed what would happen if you mixed both solutions together? Would it be brighter for longer or dimmer for shorter?
So indirectly he can turn Asprin into Glow sticks
is this why my grandma is so vibrant?
Since the true glow is hard to capture on video, as well as the viewers screens displaying it how you intend, maybe use something that can quantify the light output? (I think the unit for brightness is _lux,_ or perhaps there's a more suited alternative that im not aware of).
Just an idea :-)
It feels as I watched your last year ChemisTree video yesterday. Time is passing...
"which.. weren't exactly pleasant" fuckin a I love you nilered
Love the black background cut straight to the brightest white webpage you've ever seen. RIP MY EYES
question: in this vid and the tcpo vid, you used amines to neutralize the acid byproduct. why not use something easier to get like NaOH? would it react with the oxalyl chloride in an unintended way?
"Environmentally mean" 😂 I love that description
do a video tasting the glow sticks to see if they taste minty fresh
That's is a nice bottle of Nuka Cola festive green you made the at the end ;) Glowing should last hundreds of years though :)
this video is exactly what i need right now lol LoVe It thaNKS
Ive got something else you neeD
... VINKS? What does that mean??
Nilered... Question... Is it safe to assume the dye is responding to UV light the reaction is creating?
"...it turned yellow, but it isn't really a problem.."
"Explosions&Fire would like to know your location."