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In this video, I decided to try and extract indigo dye from an old pair of jeans. I managed to find a decent way to do it, and in the future, I'll try to scale up the process and do it on a full pair.
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Nile talks about lab safety: • Chemistry is dangerous.
Music in credits (Walker by SORRYSINES): / walker
Me, knowing absolutely nothing about chemistry: hehe color
lol
Can relate
"CoLoUr"!!!!111!!11!!!1111!!!!!!11!!!1!!
chroma
@@MicroageHD ew colour
Seeing your trial and error is my favorite part of your videos. So many other science type channels just tell you what is but you really go into it and sometimes get unexpected results. BY FAR my favorite chemistry channel.
I send these to my former chem teacher that he tells his students about. He really likes his trial and error also.
I'm glad you like that aspect. It's my favorite thing to do.
Isn't that the damn truth
That's my favourite parts too! Reminds me that experiment is never perfect and I should not pressure myself too much on perfection. Let knowledge and wisdom come as I go.
I don’t really like chemistry because it was boring, but you made it fun because of the weird experiments you do. Whenever chemistry is mentioned in anything I start getting bored before I found you, on the video where you made your own glow sticks
Heh, the idea of using pH-paper in a cup of dye seems problematic.
Mmmh.. Dat face...
Thats funnu
Pietro Bozzetto yall were meant to be
Lol
Thought about the same thing
"Didn't fit me anymore" Nilered becoming thic c
Extra Thicc
i hate this comment
r/cringe
"Moe Chan"? You don't even know Mugi's name but you put her as your profile picture? how dare u
23333
"I need a solvent that is cheap and nontoxic as possible" *Uses DCM*
Well, it's cheap and fairly non toxic compared to most solvents.
DCM is the least toxic chloroalkane solvent, so.
Isn't DCM a carcinogen though
Rubbing alcohol gets poison added to it so people don't drink it (sales tax and special sales requirement for alcohol)
@@FaiienWings What isn't a carcinogen nowadays?
Next video idea: "Extracting cocaine from a vintage Coca-Cola bottle"
Id watch it
its a tutorial 😎
He likes to sleep at night though.
My son is 6 and loves your demonstrations! I caught him in the driveway wearing goggles playing in a puddle. I asked him what he was doing.. Chemistry Dad, Chemistry, he said. Keep up the great work 👍🤘
First I need to thank you, thank you for letting him discover this channel, please keep the drama, vlogging and personailty driven content out of his life. I have seen many young minds being destroyed by these personality. I am not saying that these channels are bad and bad influnence but what i am saying is that they have such strong connection with marketing rather than content and trying to pander to the 2018 "edgy" persona. It is becoming more and more hard to keep children away form these marketing schemes and bad influence. Although it might seem like i am going off topic but please keep him away form them.
Too bad there is an epidemic there are no jobs :(
Just make sure he doesn’t start mixing the windex and bleach in the bath tube
Dinglechalk Crumblewalk Er I want to agree with you but you have extremely bad spelling and edited your comment.
This could be a r/thathappened
NileRed, regarding Sodium Hydrosulfite (aka Sodium Dithionite), which is an alkali salt itself; from Wikipedia: "It is used as such in some industrial dyeing processes, primarily those involving sulfur dyes and vat dyes, where an otherwise water-insoluble dye can be reduced into a water-soluble alkali metal salt (e.g. indigo dye)" So basically the indigo was being kept water-soluble because it was an alkali metal salt. Adding the acid neutralized the alkali and separated out the indigo dye which then was no longer water-soluble.
No it isn't what you said: it's the reduced indigo (yellow-green) that is an alkali metal salt and it is water-soluble, the oxidized form should be insoluble and blue. The solution was blue, so it should have precipitated but it didn't until he added acid.
Just because the solution is blue doesn't mean that it's not leuco-indigo; there's obviously some other chemistry going on that is neutralizing the yellow-green colour, possibly one of the secondary products from the rust out, but it's a blue solution, not a blue suspension; the indigo wasn't converted to its oxidized form, which would have already precipitated naturally. Adding the acid would have neutralized the base alkali component, which would have freed it up to be easily oxidized by the oxygen in the water, which is exactly what happened. There's no other explanation that really fits the scenario, esp. when one considers Occam's Razor.
I think you are close, but not quite! I think what is going on is that oxidized indigo can do this crazy proton transfer keto-enol isomerization of the ketone with the indole amine (google "asian textile studies indigo", first page, search for "the indigotin chromophore") makes the amino hydrogen more acidic than it ought to be in isolation. I don't think aq. NaOH by itself can deprotonate it, but if you reduce it, then let it oxidize, perhaps the proton gets "stuck" and you are left with the sodium salt of the mono-enol indigo. Just speculation. There is more than meets the eye here, like Thunderfoot and the Coulomb explosion.
I'm here to argue. I think the nitrogen was deprotonated forming an imine and an enolate which may or may not have become a salt. Change my mind
The amine groups on indigo are more like vinylogous amides, so the amine proton might be more acidic. Wikipedia says that the pKas of amides are typically above 15 though, so I don't think OH- is a strong enough base. Maybe in dilute solution enough indigo is deprotonated to afford enhanced solubility.
Need to see this go full and extract all the indigo. I'd shred the fabric smaller first though.
Was thinking that too, blend the jeans!
Hmm, I disagree. Shredding it more will add more fibers that float around in solution. Rather have it in one piece.
@@Mp57navy Won't really matter when he filters and rinses it anyway. The solid fabric pieces are traping the solution in the weave, with it shreaded it will be much easier for the solution to both get in, and get out. If he was going to stick with not filtering though, then strips would be the better way to go.
+Oleg fair enough.
@@Oleg-oe1rc as long as you press the shreds to get all the liquid or vacuum filter it
What if you take the leftover denim, and break it down and make moonshine out of it?
The ultimate crossover episode
And then safely dye it with the dye(somehow) and show it as a moonshine "potion"
@@icebiirb9440 That's easy. Just use food coloring.. and there are blue liquor out there, probably using some berries.
@@taiwanluthiers He could use indigo carmine to dye it. Full circle.
OH HI MEMBER
Okay, a couple of things. I've been working with indigo for a few years during my PhD, so there are a few things you could try. For one, as you alluded to, indigo's one characteristic property is its abysmal solubility. Good for a dye, bad for a reagent. Older german papers talk about its solubility in either boiling chloroform, or in neat sulfuric acid, but we have typically used it as a suspension in DMF at around ~260 mg in 40 mL. By itself, it is not very soluble, but a lot of derivatives are considerably more soluble because they typically have less inter/intramolecular hydrogen bonding. Salts in particular have higher solubility (probably why you werent getting anything precipitating before adding acid - indigo is fairly acidic because the N-anion is stabilised), and N-alkyl derivatives are fairly well-behaved (i.e. di-boc indigo will dissolve in hexane). Because of the hydrogen bonding and electronics aspects, a lot of derivatives have different colours. N-acetyl indigos are typically red, mono-N-alkyl derivatives are usually blue, and di-alkyl derivatives are green. The really interesting stuff comes from other modifications of the core ring structure, which is what I've been working on. If you're interested, get in contact and we can talk more about it.
Someone else working on a PhD with indigo? What group? We've found 2-ethoxy ethanol works surprisingly well. The salts are green and absorb out in the 750 nm-ish range (at least in THF). The di-boc is a gorgeous color, isn't it?
Would it be possible to convert indigo while it is on cellulose? I mean could you take blue jeans and add red, green color to them, after they were dyed? Because if you could, then you could add colorful patterns onto generic blue denim.
@@dillonhofsommer5648 I've been working with Paul Keller at Wollongong for the last few years. I remember my Honours year when I made a batch of Di-boc indigo. Working up the reaction, I was condensing it down on the rotovap, when suddenly it precipitated and the huge increase in nucleation sites bumped it into the condensor and stained it hot pink. Bit of fun cleaning it all up.
@@tedmcleod-morris I think it would depend what kind of chemistry you're trying to do, but there's no reason why it wouldn't work. Solid-supported synthesis is a big deal now, so I think the biggest limitation would be using cellulose itself due to the amount of water/hydroxyl functionality.
I work with indigo diimines. I don't think there's a time that I've rotovapped it that it HASN'T bumped aha
I love chemistry and am a horrible test taker. I was getting a 54 in grade 11 chemistry and my teacher saw I wasn’t stupid and asked what the problem was. I told her I loved the class and understood her, just had test anxiety. I showed her one of your videos and said “this is why I took chemistry. I love it and I understand it” she ended up loving your channel and having good conversations with me over them. She passed me with a 70 after the exam. Thanks for your help there 😂. I won’t be continuing chemistry next year but I will be continue watching your videos
Based teacher
You should keep with chemistry if you love it. Don't just give up because of a problem like test anxiety.
@@Jynxedlove Sadly, if it tanks your gpa, then that might be a good idea. That or get a teacher that grades primarily off school work rather than tests. Some teachers grade differently so it really depends.
@@kaitlynp5823 I mean I'm long out of college, and medical issues not being addressed tanked my GPA.
I love this channel because you do a really good job of talking and explaining your methods, and your production quality has increased tremendously over time. I think I've learned more about chemistry by watching your videos than I ever did in high school. Keep this up and you'll have a golden play button in no-time :)
most definitely learning more here then at highschool
@@JuiciestLoot *than, maybe you should go back to highschool
gotta be a grammar nazi? better with math ,THAN spelling
Sebastiano what are you twelve?
Nicely done! I like the explorational video format. You really excelled at taking me through the process.
This video feels a lot more like "practical chemistry" than "educational chemistry", love it.
I am clueless about all of this stuff, BUT I love watching and listening to your videos. I feel like I'm in a science class I missed out on.
Read the title and thought “my washer already does a pretty good job at that”
One reason I really love chemistry is that even masters get confused. There are so many combinations of things that could happen
Your channel is so interesting and cool! Although I’m just a 15 year old chemistry enthusiast, I would really like to do stuff like you someday! ♥️
I'm glad you like it :)
You're a Freddie Mercury fan and I am a MOONWALKER
You’re 18 now, so?
I literally got an ad about indigo jeans dye, that's so oddly specific wtf
Do quinine from tonic water
Hail Schweppes
fun fact, tonic water glows blue under UV light.
Daniel Cogburn this is due to quinine, the point of this comment
Ashencloud You’re assuming that he didn’t know that.
How much quinine is in tonic water though
The organic solvents did SOMETHING though. Could you use an automated repeated extraction like with a soxhlet extractor? Or would the heating costs then outweigh the labour + chemical savings? Still waiting for you to make tea with a soxhlet extractor by the way...
Considering how cheap the drain cleaner + small amount of acid are I don´t think there´s much point mucking about with solvents.
Soxhlet extraction
Hey NileRed, I have seen your videos pop up in my recommended feed a lot and just recently clicked onto one of your videos for the first time. Since then I have watched quite a bit of your videos, and your videos are really fascinating. I know next to nothing about chemistry but yet you somehow make it interesting. Never thought watching a video about making soap would be so entertaining. I just want to say that your content here on KZhead is amazing and you should keep it up! :D
NotLikeThis
Kkona brother
'sup
Wow, this was so fun!! I’m a linguist, so I never dabbled much in chemistry, but it was always the science I enjoyed the most. I’d love to see a full extraction!! You were so informative!
im a linguist currently procrastinating a syntax assignment by watching this, and i feel solidarity across time and space with this comment
@@ilexdiapason 3 years later and I too am currently avoiding some syntax work I have to do. Great linguists think alike
Even though I find all of his videos really interesting, my favorite parts is near the beginning or end when he includes just pictures of him having fun. By far my favorite part about learning applied science and chem is actually enjoying what you're doing. For someone whose main job is probably spending laborious hours on conducting these kinds of interesting experiments, it feels really good seeing that they enjoy what they do :)
Strictly speaking from a geological background, but strong bases are used in particle size analysis for clays and silts. What happens is that the base prevents the clay grains from clumping together by interrupting the static charge that builds up on the surfaces of the grains. Perhaps, a similar process is happening with the indigo.
Love being a supporter of one of the most fascinating channels on KZhead.
I'm so glad that I found your channel! You're videos are so fascinating and fun to watch and I really learn a lot. I think you explain things very cleanly and it's really easy to understand. And I also have a huuuugeeee amount of respect for you for putting in "fails"! Its a huge part of learning and I really appriciate it.Lots of love! Keep up the amazing work!
You just demonstrated subtractive dye for jeans. The patterns in your final sample are attractive and could be extended to creating a 'tie dye' look in jeans. Fabric artists would be very interested in decorating indigo dyed garments by protecting some of the fabric with tightly wrapped string, or even wax and then subtracting indigo. Congratulations.
Yes! Bucket chemistry! I love bucket chemistry! Please show us the full scale extraction from the whole jean!
Nice video as always dude! I'd love to see a scaled up indigo extraction at some point, that would be pretty damn cool to watch.
Yeah I think it'll happen!
Oh my god i love the way he keeps all the scenes in proportion to each other and throws off the sense of scale.
So close to 500k subs, TY for keeping my interest in chemistry re-active and accessible. With the ignition stuff might talk with Cody's Lab & Scott Manley colabs might help put you over a bit faster and have some good input/problems to test. Anyhow keep doing what you do I really appreciate it.
Time to make some white- blue jeans
Please do the full scale extraction, I think it's really interesting
Every day I watch your videos and learn more about chemistry. It is absolutely one of my favorite subjects in school, and I enjoy learning about all of the different elements and chemicals you use in your procedures. I never even thought some of these things you made videos on could be possible.
Honestly; I find these videos super fascinating when i’m awake, and relaxing when I’m tired! I can easily fall asleep listening to your voice
Try to extract MSG from common foods like tomatoes, seaweed, and more.
please full scale extraction. love your videos. especially with my fear of chemials so im glad you do this so i dont have to, lol
I absolutely love you Nile Red... Thank you so much for all of your videos!
Yes please! I’d love to see a full extraction. It would be interesting to see if the solution could be applied by pouring it on the jeans or dripping to selectively remove the indigo to style the jeans.
Dissolve the cellulose instead. :)
damn didn't realize that someone already commented this
Such a severe reduction/ dehydration could denature the indigo.
Maybe with the Schweizer solution.
Could you make another Edible Chem video? Maybe about MSG? It seems very interesting
The true mark of a great KZhead channel is an audible promotion. Glad to hear that you made it to stardom
This dude is absolutely crazy!! Every video I watch my mind gets blown! I never have any idea of wtf he’s talking about or how he does it but this dude does it.
The sodium hydroxide probably formed a salt with the indigo, since it has a N-H group that is a bit acid. When you added the HCl you converted the salt back to indigo.
The N-H bond shouldn't be so acidic to get deprotonated by NaOH
I think it should, apparently indoline has a pKa of 4.9 (www.scripps.edu/baran/heterocycles/Essentials1-2009.pdf - I know, not a very good source, but good enough for a youtube discussion =P). In indigo the pKa might be even lower because of the carbonyl group.
According to predicted data from chemicalize.com the strongest acidic pKa is 8.48. Honestly take the time to check it out, this compound has some interesting characteristics IMO. Indigo will not work in the search bar but its IUPAC name will "(2E)-2-(3-Oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one". Let me know your thoughts!
@@grgvv I think it does. Check out the chemicalize data - It's really interesting.
Hey! I have taken up a recent interest in chemistry and I tried looking for the "glucose/fructose" heavy molecules. In other words, the molecule would be Si6Li12S6. I couldn't find anything on it, and I was also wondering what such a molecule would do to a cell.
"Ignition!" is an absolutely wonderful read -- lots of interesting chemistry and funny anecdotes to go with them. Glad to see you recommending it :)
Would you be interested in doing a series on pigments? Vermilion is a interesting pigment to make and there are a lot of others that's could produce exciting results
read in a car, thought you said you wanting nilered to get you pregnant
15:44 : Usually it's science that turns you into a crazy scientist, not Audible
I'm sorry, Mama, I never meant to hurt you I never meant to make you cry But tonight I'm 0:56
[Whatever name goes here] how to delete somebody’s KZhead comment
I don’t get it
i had to google it to get it why don't i listen to Eminem
@@elephystry eminem
I love this channel! High quality
Great video. I'm surprised the indigo can be removed from the fabric so well. I love the improved quality of the photography.
maybe air wasnt enough to completely destroy the reducing agent and the mix of oxidized and non oxidized indigo somehow helped it solubilitse the acid probably was able to remove the reducing agent and subsequently only the 1.5 mg could solubilize
Please make a video on making or extracting MSG (Monosodium Glutamate) from food
This is like science class! I just found your channel and I love it.
Can you do a video on making bio diesel from different plant oils such as sunflower or olive or corn??
How about something like a chemistry speedrun? Maybe with the Aspirin->Tylenol process
Ignition! is an AWESOME book, also terrifying in parts but AWESOME none the less.
Nile Red I love your videos, keep inspiring people to love science.
that clip at the end IS really satisfying. daily dose of internet should use it
15:45 Is it just me or did he photoshop those headphones on his head😂🤣😂😂
Acid/base extraction always works. It was the first thing I thought of.
I am very interested looking forward to see the full scale extraction
today is now a good day
When will be the next livestream?
Incredible, you just invented indigo recycling! Now our old jeans shan't go to waste, for our new ones can just use the indigo from those instead of having to synthesize more!
A couple of extraction ideas: You can try using a Soxhlet Extractor with ethyl acetate to always be washing with a clean solvent. If you stick with the solvent that you ended the video with then you should take a tube of PVC or something (after you make sure it is chemically compatible), and loosely fill it with the denim. Pour the solvent in the top, and let it drain out of the bottom. This will ensure that the solvent is getting more and more concentrated as it passes through the denim. When you think the denim that is at the top is fully extracted then you can push more fresh denim into the bottom and squeeze the denim at the top out of the pipe. Source: I am helping design a pilot scale counter-current extractor. If anybody has any questions about this process (that is not directly related to my job), feel free to ask.
Nile Red is the best KZhead channel ever!!!!! Please let this be top so everyone knows!
I CONCUR
Thanks!
we know
You're like Cody, if you used proper safety procedures and pronounced bleach as "Blech."
If indigo blue dissolved in base then why not to try a simple acid-base extraction approach ?
This. Why is he not trying that? Maybe its not good if you want to dye cotton (so they use the reduced form), but it seems to be working well for just dissolving the dye?
Anyone who thumbs downs this man is just a hater, and a snowflake. This is the best chemistry channel on KZhead for many reasons. Nile and Cody are the best 2.
I’m so happy you enjoyed the book! Also, I take it (from your use of analine) that you never got your hands on any UDMH. Too bad, but I’m pleased that you still have all your fingers and eye brows!
Huh. I thought *Ignition!* was out of print. When I went looking for it about 5 years ago I had to download an ancient pdf of it.
me: i know lots about chemistry! also me: liquid turn solid color blue acid yes
You better get started on the full scale lol, this was very cool.
Yay! We missed you!
Cool , scientific and interesting. Niceeeee
Did you consider a Soxhlet extractor?
12thealchemist probably hasnt one :/
I think he does, I remember him using it in an earlier video
It would take a *MASSIVE* soxhlet to do it on the whole jean though!
Indigo is just so insoluble (unless you go to solvents like DMF, which he doesn't want to use) there's not much point to it.
@@yatagarasu1495 he has a small one from the pepper video
NileRed and NileBlue are both awesome scientific channels that entertain me. I never knew such a thing could use so many chemicals! This is a really cool thing to watch! Kepp up the awesome work!
This was in my suggested and I’m not sure why but it was very interesting and now I’m subbed so 🤷♀️
Don't know that much chemistry, but could the indigo have stayed in solution because of the sodium citrate in the iron out?
He’s eventually gonna come out with a video called “ making methamphetamine”
From apple juice
Reason for soluble dye in base: With this particular arrangement, the two neighboring keytone-amine groups provide hydrogen bonding sites, but not quite enough to overcome the hydrophobic parts of the molecule. However, in a strong hydroxide base, the negative charged hydroxide is just the right size to squeeze inbetween the amine and keytone groups on each side and strongly lock in place through hydrogen bonding. This is similar to ligand formation with transition metal cations. It now acts as a complex with a net - charge the -OH is providing, making it much more soluble in H2O. The size of the -OH and distance between R-NH-R and =O groups are just right to create this effect. The indigo should extract directly from the jeans somewhat with a hot -OH solution, but this is just in theory...as the other dissolved species from the iron-out may act as a "soap" to help drag the indigo into solution through intermolecular interactions. I would think this should be minimal, but I'd have to study it further in detail. The -OH creating a ligand-like complex, though, im quite confident is mainly responsible for the unexpected solubility.
I completely agree! I really don't think the "Iron Out" is needed, just some 0.1N NaOH solution and some gentle heating and agitation.
You were missing something reasonably obvious. The iron out contains sodium carbonate and hence the pH will have initialy means it will have been around 9/10. A typical amide has a pKa of around 18, which means you'd need sodium hydroxide (and of course anything more basic) to deprotonate it. Indigo however, will have a much lower pKa, so much lower in fact one of the amides is fairly easily able to exist in it's iminol form. This is because the deprotonated nitrogen can delocalise it's negative charge across both oxygens and one of the aromatic rings. And hence the much greater anion stability and lower pKa. So clearly based upon that sodium carbonate was easily able to deprotonate the indigo and produce a water soluble sodium salt which you then destroyed by adding the HCl.
could you do a soxhlet extraction of the denim after grinding it finely with a blender?
I get the dye out by wearing them.
got a jeans/indigo ad in front of this video... now that's just gold
You are doing better job in making chemistry fun and interesting then any of my chemistry teacher. Great video!
If there's a hydroxide bound to the oxydized indigo it might get protolyzed with an hydrogen ion from the acid to water? My guess, I haven't studied chemistry in years
I think that it would be more likely that in basic conditions -NH- group gets deprotonated therefore increasing solubility.
Could be. Anyways I see it as most likely being some polar group in bound with the oxy-indigo that gets protolyzed with the acid
It seems the wikipedia page for Sodium dithionite has all the answers. As the compound "Sodium hydrosulfite" does not exist and Sodium dithionate is referred to as such. > Although it is stable in the absence of air, it decomposes in hot water and in acid solutions. (en.wikipedia.org/wiki/Sodium_dithionite)
"Point something obvious out" "Make you look stupid" Me:
...huh?
Great video, FYI, indigo Carmine will deprotonate above pH 13, so it's possible that the indigo would as well. However that form is a green NIR dye. Most likely what happened is you had incredibly fine particles. If you end up making Carmine, consider doing the stoplight reaction... It's so cool, and call be gorgeous.
this is by far the only channel that actually has a thumbnail that isn't fake or click-baity
wait... so this whole time i thought you could use bleach to extract indigo?! ;-; whoops
Saluditos a todos los de habla hispana
Buenas!
Gracias!
Que?
Si
¡Gracias!
definitely, do the full-scale extraction!
It made such a cool pattern on the jeans for the double washed test! You should do the same experiment with a whole pair of jeans
That's cool and all, but can you extract happiness from the void that is life?
i tried to do this in school and failed miserably lol
good video man as usual
My guess on the solubility fix is that the NaOH you added in advance of the iron-out deprotonated the secondary amines and allowed for the salt to form between the indigo and iron out. The HCl in turn protonated the indigo preferentially allowing it to return to its normal crashing out behavior in water
I got an ad about the indigo in jeans 😂 Who else!?