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.
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
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.
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.
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.
@@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.
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.
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
@@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.
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 :)
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!
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.
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...
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.
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 :)
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 TH-cam is amazing and you should keep it up! :D
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.
The PH of the sodium hydroxide is quite large (14), making it a base, and neutralising the acid in the iron out (with a PH of one, highly acidic), making it turn into water and salt. This makes the indigo come out of solution.
I’m fascinated by chemistry, but don’t know much more than the basics about it. I do have a recommendation for this, though: the washed scraps of denim from your second extraction clearly have dark spots where the fabric folded and didn’t move around much, so the indigo didn’t have a chance to dissolve and escape from the fabric. If you ever plan to do this on a larger scale, like with a whole pair of jeans, I’d recommend either using some method that lets you physically move the solution to shake it and the fabric around to shake loose the dye (although I can’t think of a way to do it that wouldn’t require a huge dissolving solution and way too much of the chemicals), or cut the fabric into far smaller pieces (or even just shred it) so that they can move around more freely. Also, you consistently referred to the reducing agent as dithionite in the first video; is that another term for hydrosulfite?
Anyone who thumbs downs this man is just a hater, and a snowflake. This is the best chemistry channel on TH-cam for many reasons. Nile and Cody are the best 2.
Either you're forming a ketal that's more soluble; and/or the indigo is precipitating as a charge-stabilized colloid. As soon as you acidify it, the colloid breaks and the indigo clumps together.
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.
Explanation to 8:45: Indigo's molecule is more or less only slightly positively polar that water alone is not enough to dissolve it. NaOH combined with water was good to dissolve it since the polarity is constructive, when you poured acid, you threw the polarity out of bond, and the Indigo precipitated as a result.
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.
Take a look into liquid-liquid extraction. Some indigo salts probably formed with some sodium from the iron out and caused the indigo to be much more soluble in water. Then when you added the HCl it pulled the sodium back off of the indigo, causing it to crash out. Its commonly done with benzoic acid and phenanthrene in lab courses in college.
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.
We use sodium dithionite and sodium citrate to extract Fe and Al from soil for mineralogical analysis. Similarly Oxalic acid and ammonium oxalate to do the same for Si, Al, and Fe (poorly crystalline forms). Using a salt to help suspend and hold the extract to obtain higher yields. Additional freezing the solution will cause precipitate to form for recapture.
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
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!
The denim sample from the second wash method looks beautiful. If you could do that process to an entire pair of jeans it would create a Rorschach Test / Tie-Die pattern that would look amazing and be completely unique from each other.
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.
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!
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.
If you could find out what caused the indigo to appear to dissolve in water (or at least finely suspend itself in water) then maybe you can repeat those conditions to get the indigo to drop directly out of the cloth into the water suspension.
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.
The indigo has 2 vinylogous amides with both carbonyls conjugated together. Additionally, it is also essentially a 2-acylaniline dimer and the electron withdrawing carbonyl decreases the electron density on the aniline nitrogens making the N-H protons more acidic. With this combination of functional groups and the presence of several pathways for the negative charge to be delocalize, the base is probably able to deprotonate one of nitrogens to generate the water soluble anion.
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?
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.
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.
it probably formed a colloid with particles of indigo less than 10 microns wide which are too small and too dispersed to be filtered by a coffee filter. I'm no chemist so I'm not sure how fine of particles you can filter out with your fancy equipment but I think it would be worth a try in addition I would be interested to see about reusability of the chemicals used in the process and see if it would be practical to extract a large amount without having to clear the shelves of drain cleaner and rust out
Having watched several different videos on this channel, I've got a couple of suggestions that I'd like to see you do: • With the current problems with infrastructure that are happening worldwide, I'd like to know some of the alternate methods for removing the lead compounds (leached from ancient lead pipes) from contaminated water to make it potable again. • There's an extraordinary material I'd love to see you try to make - *Aerogel* . It's got so many amazing properties, such as extremely low density & excellent thermal insulation.
What I think, not 100% sure. So, NaHSO3 is an acidic salt, hence its H+ ions given in water dissociation. I'm pretty sure that the blue color came from the formation of indigo carmine (disodium 5,5′-indigodisulfonoate). Indigo reacted with SO3(2-) ions in the solution to form 5,5'- indigosulfonic anions(1-) wich on their side reacted with the Na cations(1+)[from the NaOH]to form the indigo carmine; the carmine is blue and soluble in water. Adding the HCl acid reacted with it. The Na cations reacted with the Cl(1-) anions to form NaCl and the H(1+)[from HCl], which replaced the sodium ones, just created 5,5'-indigosulfonic acid which later due to the excess of H(1+) ions from the NaHSO4 just dissociated to indigo(which precipitated) and 2 molecules of H2SO3. But I'm not sure like I said :)
Nice job. If only I saw this in the 80s... extracting the indigo would have produced some pretty styling jeans from the look of it... almost a tie-dye/bleaching effect.
I was playing with acetone and denim earlier today! The knee of the pants was stained blue with paint from a mural I did. The lighter parts of the jeans actually made it match fairly well , I was trying to get some of the paint out I happens to have acetone out so decided to give it a shot , I have yet to examine the results but it seemed to blend it better . It's still rather a shame because I had considered those one of my nicer pairs and I usually forget the stain until I'm out in public. Oh well I'm an artist I'll wear it proudly
I know this is nearly 2 years old now, but it would be really interesting if you did this with selvedge denim, specially from Japan. Indigo in the Japanese denim circles is a very celebrated aspect of making selvedge denim.
I think that blue form of indigo just form some kind of stable colloidal solution. particles in such solutions have electric charge and by adding acid you add more ions with opposite charge and coagulation starts. Sorry for bad english..
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 loved Ignition. You will never find a more honest book about the development of rock fuel throughout history. It really does go into all the gory details without sacrificing the technical details that became our collective knowledge of rocket fuels. It doesn't matter if your a layman, chemist, physicist, rocket scientist or whatever; that book really does have a lot of offer to the reader.
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
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)
About the addition of acid, since iron out had sodium, it would have hydrolysed to give sodium hydroxide. Hence it was in solution form. But when you added acid, the base would have neutralised hence the indigo started precipitating. This is my thought about that.
I think you should wring out the bleached fabric before sending it to another extraction step. Any liquid you can get out of it with extracted indigo will increase your yield.Also, any indigo that deposits on your glassware or gloves can be recovered using another batch of the reducing solution. Perhaps the indigo formed in the alkaline solution under intense stirring is just particles too fine to settle or filter out, and with a surface charge that prevents them from clumping. Acidifying the solution allows them to clump up so they can settle and are caught in the filter. Could you oxxygenate the solution with hydrogen peroxide? It should not take much. Or perhaps you could find some form of stirring which incorporates as much air but stirs the liquid less. Maybe acidify even before you start aerating?
This is by far and away the coolest channel on youtube, thank you for your work! (Also the Cinemaldehyde clock reaction video was helpful information source for a ChemE Car timer.) Edit: Ignition is an amazing read! Highly recommend it to anyone who hasn't read it yet.
As discussed by another comment, the indigo compound has an N-H bond, and pi bonds near it that help contribute to its resonance. The resonance then stabilizes the N-H bond so it becomes an acidic proton. That’s my theory
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!
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
i would’ve removed the fabric asap, as in as soon as it appeared colorless, i also would’ve used the left over fabric until it was snow white. simply just because since i know you liked to have a small surplus of chemicals so i feel like it would’ve been the smartest and most useful way of doing it, but i know this is 2 years old and i’m not a chemist so you definitely know more than me
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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
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.
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
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
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
Me, knowing absolutely nothing about chemistry: hehe color
lol
Can relate
"CoLoUr"!!!!111!!11!!!1111!!!!!!11!!!1!!
chroma
@@MicroageHD ew colour
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
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.
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
"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?
This video feels a lot more like "practical chemistry" than "educational chemistry", love it.
"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
Next video idea: "Extracting cocaine from a vintage Coca-Cola bottle"
Id watch it
its a tutorial 😎
He likes to sleep at night though.
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.
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
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.
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
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?
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.
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 :)
Love being a supporter of one of the most fascinating channels on TH-cam.
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 TH-cam is amazing and you should keep it up! :D
NotLikeThis
Kkona brother
'sup
Oh my god i love the way he keeps all the scenes in proportion to each other and throws off the sense of scale.
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
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.
One reason I really love chemistry is that even masters get confused. There are so many combinations of things that could happen
The true mark of a great TH-cam channel is an audible promotion. Glad to hear that you made it to stardom
Yes! Bucket chemistry! I love bucket chemistry!
Please show us the full scale extraction from the whole jean!
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
The PH of the sodium hydroxide is quite large (14), making it a base, and neutralising the acid in the iron out (with a PH of one, highly acidic), making it turn into water and salt. This makes the indigo come out of solution.
I’m fascinated by chemistry, but don’t know much more than the basics about it. I do have a recommendation for this, though: the washed scraps of denim from your second extraction clearly have dark spots where the fabric folded and didn’t move around much, so the indigo didn’t have a chance to dissolve and escape from the fabric. If you ever plan to do this on a larger scale, like with a whole pair of jeans, I’d recommend either using some method that lets you physically move the solution to shake it and the fabric around to shake loose the dye (although I can’t think of a way to do it that wouldn’t require a huge dissolving solution and way too much of the chemicals), or cut the fabric into far smaller pieces (or even just shred it) so that they can move around more freely.
Also, you consistently referred to the reducing agent as dithionite in the first video; is that another term for hydrosulfite?
Read the title and thought “my washer already does a pretty good job at that”
So a surfactant could do a good job
Anyone who thumbs downs this man is just a hater, and a snowflake.
This is the best chemistry channel on TH-cam for many reasons.
Nile and Cody are the best 2.
Either you're forming a ketal that's more soluble; and/or the indigo is precipitating as a charge-stabilized colloid. As soon as you acidify it, the colloid breaks and the indigo clumps together.
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.
I literally got an ad about indigo jeans dye, that's so oddly specific wtf
Explanation to 8:45: Indigo's molecule is more or less only slightly positively polar that water alone is not enough to dissolve it. NaOH combined with water was good to dissolve it since the polarity is constructive, when you poured acid, you threw the polarity out of bond, and the Indigo precipitated as a result.
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!
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.
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.
Take a look into liquid-liquid extraction. Some indigo salts probably formed with some sodium from the iron out and caused the indigo to be much more soluble in water. Then when you added the HCl it pulled the sodium back off of the indigo, causing it to crash out. Its commonly done with benzoic acid and phenanthrene in lab courses in college.
Try to extract MSG from common foods like tomatoes, seaweed, and more.
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.
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 TH-cam comment
I don’t get it
i had to google it to get it why don't i listen to Eminem
@@elephystry eminem
We use sodium dithionite and sodium citrate to extract Fe and Al from soil for mineralogical analysis. Similarly Oxalic acid and ammonium oxalate to do the same for Si, Al, and Fe (poorly crystalline forms). Using a salt to help suspend and hold the extract to obtain higher yields. Additional freezing the solution will cause precipitate to form for recapture.
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
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!
Please do the full scale extraction, I think it's really interesting
The denim sample from the second wash method looks beautiful. If you could do that process to an entire pair of jeans it would create a Rorschach Test / Tie-Die pattern that would look amazing and be completely unique from each other.
Yeah, I loved that design! I immediately thought of the marketing possibilities.
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.
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 make another Edible Chem video? Maybe about MSG? It seems very interesting
If you could find out what caused the indigo to appear to dissolve in water (or at least finely suspend itself in water) then maybe you can repeat those conditions to get the indigo to drop directly out of the cloth into the water suspension.
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.
this is by far the only channel that actually has a thumbnail that isn't fake or click-baity
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
The indigo has 2 vinylogous amides with both carbonyls conjugated together. Additionally, it is also essentially a 2-acylaniline dimer and the electron withdrawing carbonyl decreases the electron density on the aniline nitrogens making the N-H protons more acidic. With this combination of functional groups and the presence of several pathways for the negative charge to be delocalize, the base is probably able to deprotonate one of nitrogens to generate the water soluble anion.
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?
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.
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
Best science channel on TH-cam , together with Cody's Lab and The Action Lab , congratulations !
I wish I could go to Canada and meet you !
What about nurdrage
@@lcob490 Yes , Nurdrage does very nice reactions , but gets to deep in the explanations , which bores me 😑 .
How about something like a chemistry speedrun?
Maybe with the Aspirin->Tylenol process
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.
Please make a video on making or extracting MSG (Monosodium Glutamate) from food
it probably formed a colloid with particles of indigo less than 10 microns wide which are too small and too dispersed to be filtered by a coffee filter. I'm no chemist so I'm not sure how fine of particles you can filter out with your fancy equipment but I think it would be worth a try in addition I would be interested to see about reusability of the chemicals used in the process and see if it would be practical to extract a large amount without having to clear the shelves of drain cleaner and rust out
Time to make some white- blue jeans
Having watched several different videos on this channel, I've got a couple of suggestions that I'd like to see you do:
• With the current problems with infrastructure that are happening worldwide, I'd like to know some of the alternate methods for removing the lead compounds (leached from ancient lead pipes) from contaminated water to make it potable again.
• There's an extraordinary material I'd love to see you try to make - *Aerogel* . It's got so many amazing properties, such as extremely low density & excellent thermal insulation.
When will be the next livestream?
What I think, not 100% sure. So, NaHSO3 is an acidic salt, hence its H+ ions given in water dissociation. I'm pretty sure that the blue color came from the formation of indigo carmine (disodium 5,5′-indigodisulfonoate). Indigo reacted with SO3(2-) ions in the solution to form 5,5'- indigosulfonic anions(1-) wich on their side reacted with the Na cations(1+)[from the NaOH]to form the indigo carmine; the carmine is blue and soluble in water. Adding the HCl acid reacted with it. The Na cations reacted with the Cl(1-) anions to form NaCl and the H(1+)[from HCl], which replaced the sodium ones, just created 5,5'-indigosulfonic acid which later due to the excess of H(1+) ions from the NaHSO4 just dissociated to indigo(which precipitated) and 2 molecules of H2SO3. But I'm not sure like I said :)
Don't know that much chemistry, but could the indigo have stayed in solution because of the sodium citrate in the iron out?
Nice job. If only I saw this in the 80s... extracting the indigo would have produced some pretty styling jeans from the look of it... almost a tie-dye/bleaching effect.
Can you do a video on making bio diesel from different plant oils such as sunflower or olive or corn??
I was playing with acetone and denim earlier today!
The knee of the pants was stained blue with paint from a mural I did. The lighter parts of the jeans actually made it match fairly well , I was trying to get some of the paint out I happens to have acetone out so decided to give it a shot , I have yet to examine the results but it seemed to blend it better . It's still rather a shame because I had considered those one of my nicer pairs and I usually forget the stain until I'm out in public. Oh well I'm an artist I'll wear it proudly
15:44 : Usually it's science that turns you into a crazy scientist, not Audible
I know this is nearly 2 years old now, but it would be really interesting if you did this with selvedge denim, specially from Japan. Indigo in the Japanese denim circles is a very celebrated aspect of making selvedge denim.
that clip at the end IS really satisfying. daily dose of internet should use it
I think that blue form of indigo just form some kind of stable colloidal solution. particles in such solutions have electric charge and by adding acid you add more ions with opposite charge and coagulation starts. Sorry for bad english..
15:45 Is it just me or did he photoshop those headphones on his head😂🤣😂😂
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
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.
I loved Ignition. You will never find a more honest book about the development of rock fuel throughout history. It really does go into all the gory details without sacrificing the technical details that became our collective knowledge of rocket fuels. It doesn't matter if your a layman, chemist, physicist, rocket scientist or whatever; that book really does have a lot of offer to the reader.
today is now a good day
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)
About the addition of acid, since iron out had sodium, it would have hydrolysed to give sodium hydroxide. Hence it was in solution form. But when you added acid, the base would have neutralised hence the indigo started precipitating. This is my thought about that.
Nile Red is the best TH-cam 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."
I think you should wring out the bleached fabric before sending it to another extraction step. Any liquid you can get out of it with extracted indigo will increase your yield.Also, any indigo that deposits on your glassware or gloves can be recovered using another batch of the reducing solution.
Perhaps the indigo formed in the alkaline solution under intense stirring is just particles too fine to settle or filter out, and with a surface charge that prevents them from clumping. Acidifying the solution allows them to clump up so they can settle and are caught in the filter.
Could you oxxygenate the solution with hydrogen peroxide? It should not take much. Or perhaps you could find some form of stirring which incorporates as much air but stirs the liquid less. Maybe acidify even before you start aerating?
I get the dye out by wearing them.
This is by far and away the coolest channel on youtube, thank you for your work! (Also the Cinemaldehyde clock reaction video was helpful information source for a ChemE Car timer.)
Edit: Ignition is an amazing read! Highly recommend it to anyone who hasn't read it yet.
could you do a soxhlet extraction of the denim after grinding it finely with a blender?
As discussed by another comment, the indigo compound has an N-H bond, and pi bonds near it that help contribute to its resonance. The resonance then stabilizes the N-H bond so it becomes an acidic proton. That’s my theory
me: i know lots about chemistry!
also me: liquid turn solid color blue acid yes
Nile Red I love your videos, keep inspiring people to love science.
He’s eventually gonna come out with a video called “ making methamphetamine”
From apple juice
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!
Cool , scientific and interesting. Niceeeee
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
"Point something obvious out"
"Make you look stupid"
Me:
...huh?
i would’ve removed the fabric asap, as in as soon as it appeared colorless, i also would’ve used the left over fabric until it was snow white. simply just because since i know you liked to have a small surplus of chemicals so i feel like it would’ve been the smartest and most useful way of doing it, but i know this is 2 years old and i’m not a chemist so you definitely know more than me
That's cool and all, but can you extract happiness from the void that is life?