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.
@nicholi89336 жыл бұрын
I send these to my former chem teacher that he tells his students about. He really likes his trial and error also.
@NileRed6 жыл бұрын
I'm glad you like that aspect. It's my favorite thing to do.
@tylerlowden80235 жыл бұрын
Isn't that the damn truth
@cheesecakelasagna4 жыл бұрын
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.
@pandom_ran4 жыл бұрын
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
@egretwhite39446 жыл бұрын
Heh, the idea of using pH-paper in a cup of dye seems problematic.
@pietrobozzetto29564 жыл бұрын
Mmmh.. Dat face...
@JHbowlsCabot4 жыл бұрын
Thats funnu
@meercat18804 жыл бұрын
Pietro Bozzetto yall were meant to be
@sethamoto90614 жыл бұрын
Lol
@stiky59724 жыл бұрын
Thought about the same thing
@KainYusanagi6 жыл бұрын
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.
@grgvv6 жыл бұрын
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.
@KainYusanagi6 жыл бұрын
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.
@defenestrated236 жыл бұрын
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.
@jojobeachable6 жыл бұрын
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
@apcapc-om8sq6 жыл бұрын
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.
@littlebacchus2166 жыл бұрын
Need to see this go full and extract all the indigo. I'd shred the fabric smaller first though.
@rbbm4546 жыл бұрын
Was thinking that too, blend the jeans!
@Mp57navy6 жыл бұрын
Hmm, I disagree. Shredding it more will add more fibers that float around in solution. Rather have it in one piece.
@Oleg-oe1rc6 жыл бұрын
@@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.
@Mp57navy6 жыл бұрын
+Oleg fair enough.
@lolgamez91716 жыл бұрын
@@Oleg-oe1rc as long as you press the shreds to get all the liquid or vacuum filter it
@DrInorganick6 жыл бұрын
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.
@dillonhofsommer56486 жыл бұрын
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?
@tedmcleod-morris6 жыл бұрын
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.
@DrInorganick6 жыл бұрын
@@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.
@DrInorganick6 жыл бұрын
@@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.
@dillonhofsommer56486 жыл бұрын
I work with indigo diimines. I don't think there's a time that I've rotovapped it that it HASN'T bumped aha
@augustg20594 жыл бұрын
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
@kaitlynp58232 жыл бұрын
Based teacher
@Jynxedlove2 жыл бұрын
You should keep with chemistry if you love it. Don't just give up because of a problem like test anxiety.
@kaitlynp58232 жыл бұрын
@@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.
@Jynxedlove2 жыл бұрын
@@kaitlynp5823 I mean I'm long out of college, and medical issues not being addressed tanked my GPA.
@art_and_sh.t42655 жыл бұрын
Me, knowing absolutely nothing about chemistry: hehe color
@angelique58045 жыл бұрын
lol
@rodneyrodriguez09274 жыл бұрын
Can relate
@MicroageHD4 жыл бұрын
"CoLoUr"!!!!111!!11!!!1111!!!!!!11!!!1!!
@pianojay51464 жыл бұрын
chroma
@LupeSunglass4 жыл бұрын
@@MicroageHD ew colour
@codyv3086 жыл бұрын
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 :)
@JuiciestLoot6 жыл бұрын
most definitely learning more here then at highschool
@SebastianoZanda6 жыл бұрын
@@JuiciestLoot *than, maybe you should go back to highschool
@JuiciestLoot6 жыл бұрын
gotta be a grammar nazi? better with math ,THAN spelling
@codyv3086 жыл бұрын
Sebastiano what are you twelve?
@scripter136 жыл бұрын
Nicely done! I like the explorational video format. You really excelled at taking me through the process.
@zell90586 жыл бұрын
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 👍🤘
@preke9536 жыл бұрын
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.
@jayscoolvideosa5 жыл бұрын
Too bad there is an epidemic there are no jobs :(
@thelispinglizard54585 жыл бұрын
Just make sure he doesn’t start mixing the windex and bleach in the bath tube
@lordofthefreshwater5 жыл бұрын
Dinglechalk Crumblewalk Er I want to agree with you but you have extremely bad spelling and edited your comment.
@roboactive5 жыл бұрын
This could be a r/thathappened
@taiwanluthiers4 жыл бұрын
What if you take the leftover denim, and break it down and make moonshine out of it?
@emichaelk54864 жыл бұрын
The ultimate crossover episode
@icebiirb94404 жыл бұрын
And then safely dye it with the dye(somehow) and show it as a moonshine "potion"
@taiwanluthiers4 жыл бұрын
@@icebiirb9440 That's easy. Just use food coloring.. and there are blue liquor out there, probably using some berries.
@carbon53624 жыл бұрын
@@taiwanluthiers He could use indigo carmine to dye it. Full circle.
@Sciencedoneright3 жыл бұрын
OH HI MEMBER
@miamama97766 жыл бұрын
"I need a solvent that is cheap and nontoxic as possible" *Uses DCM*
@pietrotettamanti72396 жыл бұрын
Well, it's cheap and fairly non toxic compared to most solvents.
@biggyboablo5 жыл бұрын
DCM is the least toxic chloroalkane solvent, so.
@FaiienWings5 жыл бұрын
Isn't DCM a carcinogen though
@firstlast-cs6eg5 жыл бұрын
Rubbing alcohol gets poison added to it so people don't drink it (sales tax and special sales requirement for alcohol)
@tunnar795 жыл бұрын
@@FaiienWings What isn't a carcinogen nowadays?
@emmamattson42535 жыл бұрын
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.
@User_26 жыл бұрын
This video feels a lot more like "practical chemistry" than "educational chemistry", love it.
@moechano6 жыл бұрын
"Didn't fit me anymore" Nilered becoming thic c
@themonkeyspaw73596 жыл бұрын
Extra Thicc
@h0verman6 жыл бұрын
i hate this comment
@imockrartedcomments76726 жыл бұрын
r/cringe
@april50546 жыл бұрын
"Moe Chan"? You don't even know Mugi's name but you put her as your profile picture? how dare u
@paramecium6 жыл бұрын
23333
@Fvneral_moon5 жыл бұрын
Next video idea: "Extracting cocaine from a vintage Coca-Cola bottle"
@casino59514 жыл бұрын
Id watch it
@korihicks76964 жыл бұрын
its a tutorial 😎
@RainbowLovingRainbow8 ай бұрын
He likes to sleep at night though.
@nononattono6 жыл бұрын
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!
@ilexdiapason2 жыл бұрын
im a linguist currently procrastinating a syntax assignment by watching this, and i feel solidarity across time and space with this comment
@nononattono2 жыл бұрын
@@ilexdiapason 3 years later and I too am currently avoiding some syntax work I have to do. Great linguists think alike
@freddiemercury80906 жыл бұрын
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! ♥️
@NileRed6 жыл бұрын
I'm glad you like it :)
@muzankibutsuji46713 жыл бұрын
You're a Freddie Mercury fan and I am a MOONWALKER
@ye83482 жыл бұрын
You’re 18 now, so?
@tedmcleod-morris6 жыл бұрын
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.
@Asdayasman6 жыл бұрын
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...
@User_26 жыл бұрын
Considering how cheap the drain cleaner + small amount of acid are I don´t think there´s much point mucking about with solvents.
@CDCI34 жыл бұрын
Soxhlet extraction
@lovehawks28146 жыл бұрын
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.
@0xESSEL6 жыл бұрын
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 KZbin is amazing and you should keep it up! :D
@themonkeyspaw73596 жыл бұрын
NotLikeThis
@0xESSEL6 жыл бұрын
Kkona brother
@cosimo80466 жыл бұрын
'sup
@DrWhaThaHell Жыл бұрын
Oh my god i love the way he keeps all the scenes in proportion to each other and throws off the sense of scale.
@boba_fairy3 жыл бұрын
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 :)
@piranha0310916 жыл бұрын
Yes! Bucket chemistry! I love bucket chemistry! Please show us the full scale extraction from the whole jean!
@Munden6 жыл бұрын
Love being a supporter of one of the most fascinating channels on KZbin.
@bradleyhowes8486 жыл бұрын
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.
@johnsmith-qn2gd6 жыл бұрын
Do quinine from tonic water
@supersonictumbleweed6 жыл бұрын
Hail Schweppes
@danielcogburn43556 жыл бұрын
fun fact, tonic water glows blue under UV light.
@ashencloud21586 жыл бұрын
Daniel Cogburn this is due to quinine, the point of this comment
@elephystry5 жыл бұрын
Ashencloud You’re assuming that he didn’t know that.
@thomasgoodwin56365 жыл бұрын
How much quinine is in tonic water though
@KnakuanaRka6 жыл бұрын
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?
@ccaio55853 жыл бұрын
One reason I really love chemistry is that even masters get confused. There are so many combinations of things that could happen
@mdavh25823 жыл бұрын
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.
@razor5cl6 жыл бұрын
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.
@NileRed6 жыл бұрын
Yeah I think it'll happen!
@angelmihaylov36813 жыл бұрын
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 :)
@alexanderdechaneet40016 жыл бұрын
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.
@sketchywolff63653 жыл бұрын
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.
@kumabanh17445 жыл бұрын
Read the title and thought “my washer already does a pretty good job at that”
@rishivachaspathyastakala8663 күн бұрын
So a surfactant could do a good job
@nicholasscott18036 жыл бұрын
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.
@mmmhorsesteaks6 жыл бұрын
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.
@MaghrebProductions2 жыл бұрын
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.
@Kunait.6 жыл бұрын
Please do the full scale extraction, I think it's really interesting
@charlesham92143 жыл бұрын
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.
@k.y.6148 Жыл бұрын
Yeah, I loved that design! I immediately thought of the marketing possibilities.
@fwiffo6 жыл бұрын
Dissolve the cellulose instead. :)
@tesseract3426 жыл бұрын
damn didn't realize that someone already commented this
@e00drik16 жыл бұрын
Such a severe reduction/ dehydration could denature the indigo.
@GiovanniCarloIglina6 жыл бұрын
Maybe with the Schweizer solution.
@daniellamaster90005 жыл бұрын
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.
@dudumaurina26 жыл бұрын
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.
@grgvv6 жыл бұрын
The N-H bond shouldn't be so acidic to get deprotonated by NaOH
@dudumaurina26 жыл бұрын
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.
@rpearson5 жыл бұрын
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!
@rpearson5 жыл бұрын
@@grgvv I think it does. Check out the chemicalize data - It's really interesting.
@dejanaur6 жыл бұрын
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!
@CIubDuck5 жыл бұрын
I literally got an ad about indigo jeans dye, that's so oddly specific wtf
@hardstylerockercify6 жыл бұрын
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
@nutellaftw88646 жыл бұрын
Try to extract MSG from common foods like tomatoes, seaweed, and more.
@desert21955 жыл бұрын
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.
@aajjeee6 жыл бұрын
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
@Somedude202826 жыл бұрын
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
@julianvargo99976 жыл бұрын
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.
@potato4dawin16 жыл бұрын
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
@vlaicud6 жыл бұрын
Could you make another Edible Chem video? Maybe about MSG? It seems very interesting
@jaytuberr4 жыл бұрын
I’m not anything close to a chemist but I think that the blue form of indigo was staying in solution kind of like sometimes if you are careful you can have water below it’s freezing point and it freezes instantly when you disturb it. The acid disturbed the indigo that was in solution and it started to fall out
@geckooTec6 жыл бұрын
Please make a video on making or extracting MSG (Monosodium Glutamate) from food
@kevinmartin77606 жыл бұрын
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?
@whatevernamegoeshere36446 жыл бұрын
I'm sorry, Mama, I never meant to hurt you I never meant to make you cry But tonight I'm 0:56
@aljaberhk5 жыл бұрын
[Whatever name goes here] how to delete somebody’s KZbin comment
@elephystry5 жыл бұрын
I don’t get it
@okayaki75675 жыл бұрын
i had to google it to get it why don't i listen to Eminem
@JohnCena-kn9tv3 жыл бұрын
@@elephystry eminem
@forknspoon32754 жыл бұрын
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.
@papanyanz6 жыл бұрын
If indigo blue dissolved in base then why not to try a simple acid-base extraction approach ?
@leocurious99196 жыл бұрын
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?
@dillonhofsommer56486 жыл бұрын
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.
@aleenamurphy11825 жыл бұрын
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
@ckimsey775 жыл бұрын
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.
@rpearson5 жыл бұрын
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.
@among-us-999996 жыл бұрын
How about something like a chemistry speedrun? Maybe with the Aspirin->Tylenol process
@zbeekerm6 жыл бұрын
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!
@darrianweathington19235 жыл бұрын
Time to make some white- blue jeans
@rishikrishnanpk89314 жыл бұрын
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.
@muhammadbilalkhan29166 жыл бұрын
Can you do a video on making bio diesel from different plant oils such as sunflower or olive or corn??
@forkocharles8004 жыл бұрын
The thing I think is happening (outside of it not being indigo) is the actual pH of the water. IIRC pH 7 is for DI water. Since you use distilled water, I wonder if the pH waffles between, e.g., 6 and 8 within some range that your pH papers don't detect and that the reaction is very sensitive to pH.
@yusefdanielhassounharmouch15206 жыл бұрын
Don't know that much chemistry, but could the indigo have stayed in solution because of the sodium citrate in the iron out?
@aaronkessman78323 жыл бұрын
I wonder if the reason the hcl kicks out the indigo is because it's actually present as a colloidal dispersion not a fully dissolved solution (but too small fonthe coffee filter to catch) . These particles could be charged and have an acidic isoelectric point. If you don't want it acidic or to test this idea, you could try adding a good amount of divalent salt (eg CaCl) to destabilize it.
@12thealchemist6 жыл бұрын
Did you consider a Soxhlet extractor?
@yatagarasu14956 жыл бұрын
12thealchemist probably hasnt one :/
@ljfaag6 жыл бұрын
I think he does, I remember him using it in an earlier video
@piranha0310916 жыл бұрын
It would take a *MASSIVE* soxhlet to do it on the whole jean though!
@mmmhorsesteaks6 жыл бұрын
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.
@lolgamez91716 жыл бұрын
@@yatagarasu1495 he has a small one from the pepper video
@seeigecannon6 жыл бұрын
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.
@danielf36236 жыл бұрын
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.
@cushshonvlogs4206 жыл бұрын
15:45 Is it just me or did he photoshop those headphones on his head😂🤣😂😂
@quigonkenny3 жыл бұрын
Looks like the specific combination of chemicals you were using included something that was allowing the indigo to be soluble in water, much like how soap allows fats to be soluble in water. When you add the acid, it neutralizes that substance (or at least the effect) and the indigo precipitates out. No idea what the specific combination or substance is that's causing it, though...
@bcikablam35786 жыл бұрын
that clip at the end IS really satisfying. daily dose of internet should use it
@vuza7526 жыл бұрын
Did you consider doing a soxhlet extraction with the acetone, the poor extraction rate shouldn't be a problem then, and it would be a cheap and low labor procedure. - For collecting the acetone in the end, simply replace the condensor column with a standard destillation apperatus.
@erakettu13956 жыл бұрын
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
@EarlofDestruction6 жыл бұрын
I think that it would be more likely that in basic conditions -NH- group gets deprotonated therefore increasing solubility.
@erakettu13956 жыл бұрын
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
@Mp57navy6 жыл бұрын
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)
@tom_something6 жыл бұрын
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.
@R42PH6 жыл бұрын
15:44 : Usually it's science that turns you into a crazy scientist, not Audible
@spiderdude20996 жыл бұрын
I can't be 100% certain, but perhaps the carbonyl on the indigo is susceptible to being converted into an acetal/hemiacetal equilibrium in basic conditions? That could potentially affect solubility. Either way, the reason has to be due to the base changing something about the structure is a way that it kind of mimics the way the acids and bases change solubility of compounds with salts or whatever.
@modestus28266 жыл бұрын
today is now a good day
@Michael-bt7bq4 жыл бұрын
Acid/base extraction always works. It was the first thing I thought of.
@pernixiom3 жыл бұрын
me: i know lots about chemistry! also me: liquid turn solid color blue acid yes
@leonardfrankel89926 жыл бұрын
Ignition! is a good book. Especially because it recently got reprinted in proper ebook format. For ages it was out of print and only available as PDF with really tiny writing
@quiteindeed68094 жыл бұрын
I get the dye out by wearing them.
@cybeermancom16 жыл бұрын
we did this back in school, but i dont remember which solvent we used. i only remember that nothing worked and we used some sort of solovent combination ( fE water and ethanol) maybe that idea helps gettin it cheaper^^ ah now i remember we ended up reducing the indigo too and yes it was in the range yellow green^^ i suggest burning the jeans in case the indigo wont be burned at those temps my idea with the indigo gettin knocked out by a higher ph would be that it reacted chemically with it or the factory that produced those jeans didnt use "real" indigo
@kadenlarson99926 жыл бұрын
could you do a soxhlet extraction of the denim after grinding it finely with a blender?
@sandervandaatselaar6 жыл бұрын
Great video. I'm surprised the indigo can be removed from the fabric so well. I love the improved quality of the photography.
@jakubrudzki23256 жыл бұрын
When will be the next livestream?
@I_XuMuK_I6 жыл бұрын
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..
@nickbeliveau15564 жыл бұрын
He’s eventually gonna come out with a video called “ making methamphetamine”
@theguywhoasked61043 жыл бұрын
From apple juice
@peregrine19706 жыл бұрын
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.
@brandons10956 жыл бұрын
Nile Red is the best KZbin channel ever!!!!! Please let this be top so everyone knows!
@modestus28266 жыл бұрын
I CONCUR
@NileRed6 жыл бұрын
Thanks!
@BothHands16 жыл бұрын
we know
@submerse99936 жыл бұрын
You're like Cody, if you used proper safety procedures and pronounced bleach as "Blech."
@Woozer734 жыл бұрын
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.
@asgkllngfxxhkkvxdhkkbhjllnvcg6 жыл бұрын
Cool , scientific and interesting. Niceeeee
@vibe48426 жыл бұрын
I looked up some properties in chemicalize, and it seems that at a pH higher than 12.18, indigo is charged negative (NH goes into N-). This would explain why it's in solution under basic conditions. A lower pH causes the indigo to go back to the neutral form, which doesn't solute into water.
@geniewitabeanie4 жыл бұрын
"Point something obvious out" "Make you look stupid" Me:
@schr4pnel4 жыл бұрын
...huh?
@justincrespo39953 жыл бұрын
Maybe I'm going crazy, but with indigo being an Azo compound, the only thing I can think of is when adding the HCL, it would have protonated the carbonyl(s) causing it to become an enol. Probably why it's not precipitating. Idk just a random thought.
@kiganbriody63145 жыл бұрын
wait... so this whole time i thought you could use bleach to extract indigo?! ;-; whoops