Making Indigo and Dyeing some jeans and socks

Yeah I figured it eventually. Bromine goes everywhere except to the 6-6' positions. :)

Silviu T

Actually I have been reading a bit about indigo this weekend and I want to try a few older methods for reducing it. One is with zinc powder in alkaline environment and another one is with Fe(II). As for the dithionite, I did order a batch despite the shipping. Should last for a while.

Silviu T

My assumption was that by partially reducing it, its possible to use milder reduction conditions for the remainder. The kit uses a weaker base and no heating, but a lot more reducing agent. And you need to let it sit there for like an hour i think (vs like 5 mins if you boil). If it werent partially reduced, it would need to sit out for much longer. It's a lot nicer for people at home who dont have any chem experience.

Nile Red

Check out the product "iron out" or equivalent iron/rust removing powder based products. I used some in my Luminol video. Its a mix of bicarb, dithionite and metabisulfite i think. I havent tried it with indigo, but i was able to replace dithionite and use it in my luminol video!

Nile Red

Apparently it doesnt work to directly halogenate it and you need to build it from the ground up unfortunately.

Nile Red

I wondered that myself. It might make sense that the additional reductant is needed to reduce the remaining 40% oxidized product. But with the recipe they list on the Amazon page, they advise using a gross excess of additional reductant, nearly 1000% molar excess of the entire amount of indigo. So yeah, why pre-reduce anyway?

It appears that the pre-reduced indigo still needs to be reduced to be used, it can't be used as-is. I wonder why they bother "pre-reducing" it at all.

Silviu T

I commented about sodium dithionite on the preliminary version of this video on youtube, but now that video is gone. I had looked for a long time for a source of dithionite but couldn't find any in the usual places. Your video gave me the idea of looking in other places, and I found some for sale at a company that caters to tie-dye hobbyists (Dharma trading co). They sell mostly kits, but also have raw chemicals - among others, dithionite and thiourea peroxide. Shipping is expensive though because they must be sent as ORM-D hazardous chemicals.

Silviu T

Update: One thing I failed to consider was that for leucoindigo, ionization (by deprotonation) is a prerequisite for oxidation. Leucoindigo has two pKas, at 7.8 and 12.7, with the monoionic species (predominating around pH 10.8-11.2) being the most effective dye (solubility vs affinity). One advantage manufacturers of pre-reduced indigo state is that soda ash (Na2CO3, pKa 10.3) can be used instead of lye (NaOH, pKa 15.7). Another is that it is readily soluble, unlike the dicarbonyl indigo dye as Nile shows. These facts run contrary to my initial doubts and instead seem to indicate that what is being shipped actually is the leuco form. One reference I found reports that the lecuo diacid is formed by catalytic hydrogenation of indigo itself. But this raises a question: Can the leuco diacid be isolated by neutralizing a redox buffered solution of the leuco dianion? Edit: Forgot to add my reference, see pp. 14-15. <a href="http://bit.ly/2sZalUC" rel="nofollow noopener" target="_blank">http://bit.ly/2sZalUC</a>

I thought about that. This Amazon posting (<a href="http://a.co/06MKQcx)" rel="nofollow noopener" target="_blank">http://a.co/06MKQcx)</a> appears to be representative of other offerings. The dark color is clearly evident even at 60% pre-reduced indigo, but then again color isn't always an accurate indicator. The bags don't appear to be vacuum-sealed, although I admit they could be packaged under inert atmosphere. However, I find no mention in the instructions of precautions against air exposure.

I meant Malachite green with acids I think LOL.

Daniel Blake Shoemaker

I can't find references for indigo or its derivatives being used as laser dyes in <a href="https://www.repairfaq.org/sam/lasercdy.htm" rel="nofollow noopener" target="_blank">https://www.repairfaq.org/sam/lasercdy.htm</a> However a table linked from that page mentions that Nile Blue can be used for one, with an emission peak of 690nm (between a dull red and near infrared)

Silviu T

Very likely indigo that is reduced and then packed in absence of air. Meaning that it will start to turn blue once you open the package.

Silviu T

If leucoindigo is so air sensitive, what is pre-reduced indigo? Is it just packaged with a reductant? A quick google search came up empty.

As a follow-up to this video I suggest making some halogenated derivatives of indigo. Tyrian purple? (I remember many many years ago I attempted to halogenate indigo powder with liquid bromine I had produced from KBr and KMnO4; what resulted was a dark violet almost black powder but I never got to prove what that was as I lacked the knowledge and required chemicals)

Silviu T

If you make Indigocarmine, you can also try out making a pigment out of it by using Aluminiumsalts.

Thanks!

Nile Red

hmm interesting

Nile Red

I did, but it would have really drawn out the process.

Nile Red

You didn't consider making o-nitrotoluene and oxidizing it to the aldehyde?

Patrick Sweetman

i plan to make malchite green eventually

Nile Red

It interest me since it can be used as a dye laser medium.

Daniel Blake Shoemaker

Malchite green can be made by this method Red Nile. The leuco form of malachite green was first prepared by Hermann Fischer in 1877 by condensing benzaldehyde and dimethylaniline in the molecular ratio 1:2 in the presence of sulfuric acid.

Daniel Blake Shoemaker

I really look forward to seeing you make Indigo carmine. Perhaps Malachite green too?

Daniel Blake Shoemaker

Hey Nile Red! I'm pretty new here but again awesome performance. I really enjoy your videos keep on going!

ill be making some prussian blue at some point

Nile Red

Thanks!!

Nile Red

haha yeah, that's where the photos were from

Nile Red

Yeah, gotta fix that!

Nile Red

Hi! Around the 3 minute mark you say you have marked something in red, but there's nothing marked. Great video!

Fair enough, it wasn't in the other black background shots, like the ingredients, guess just different lighting/white balance brought it out.

Oh, that banding. I think its just because its 8bit video and it doesnt display color gradients super well.

Nile Red

I took some screenshots from my phone, and desktop, to rule out graphics drivers doing strange things: <a href="https://imgur.com/a/lPmWQ" rel="nofollow noopener" target="_blank">https://imgur.com/a/lPmWQ</a>

hmm, weird. I dont see it on my side

Nile Red

There's heavy banding on the background in the shot starting at 1:40, is this just something from it being not-final?

12:07... "Source: honestlywtf.com" lol?

Now that I've watched it a couple times. Awesome! 👍😎

Michael Aichlmayr

:(

Nile Red

good call!

Nile Red

At 2:55, "The aldehyde group that I've marked in red," I don't see anything marked red.

Wait, who are you? (Hahahaha... Just kidding.) :-)

Michael Aichlmayr

Really cool Red Nile.

Daniel Blake Shoemaker

Hey, i guess it is the same. I had no idea that woad contained indigo

Nile Red

Off topic although I have 700 ml of aged 1.33 percent Indigo carmine I made a labcoat from lots of Prussian blue. It hada cool sky blue color. Prussian blue like Indigo is not very solubile in water either.

Daniel Blake Shoemaker

This is chemically similar to woad right? You can use clips from my video if you like.

CodyDon Reeder