Nitrowool?

[powium]

Today I was experimenting with a possible way to make some fuse, by nitrating wool. I thought I might end up with a similar product to the nitrocellulose I made yesterday using a similar method with absorbent paper.

50ml 70% nitric acid and 50ml 98% sulfuric acid was added to a beaker. The temp rose to 40deg C. 1.2m wool in 6x 20cm pieces was added over 20mins. The wool turned orange then disintegrated, so I was not able to make fuse out of it, but I thought why not keep going and see what happens. The solution was at 30 deg at this stage, so I heated to 50deg and let sit for 10 minutes. The mixture was dumped into 200ml cold water.
http://img2.freeimagehosting.net/uploads/c2829933c7.jpg (http://img2.freeimagehosting.net/uploads/6e66c4eaed.jpg)

A sticky white plastic precipitate formed. This was extracted, washed with a hot NaHCO3 soln, then hot water. This photo shows the precipitate on paper towel after it was washed:

http://img2.freeimagehosting.net/uploads/adedeb3665.jpg (http://img2.freeimagehosting.net/uploads/82097b4f10.jpg)
http://img2.freeimagehosting.net/uploads/3e5fc3367a.jpg (http://img2.freeimagehosting.net/uploads/a5514fa9f3.jpg)


The substance was dried in the oven, then looked like this:
http://img2.freeimagehosting.net/uploads/ad5b633b28.jpg (http://img2.freeimagehosting.net/uploads/265e95e3ff.jpg)
http://img2.freeimagehosting.net/uploads/00acebc36f.jpg (http://img2.freeimagehosting.net/uploads/7a8e01517e.jpg)

I tried to ignite the substance, and while hard to ignite it did burn, but not deflagrate by any means, and the burn was barely self sustaining.
Does anyone know what it is?

[nbk2000]

Looks like Cracker-Jack popcorn! :D

[megalomania]

I have had nitrocellulose behave in a similar manner, likely due to a low nitrogen content. The ancients nitrated everything back in the day, according to the Encyclopedia of Explosives and Related Items... It says they usually heated the material being nitrated (including wool) to boiling. It makes some picric acid... that might explain your yellow coloration in the picture. Other than the formation of some picric acid I can't find any other mention of nitrated products from wool.

Picric acid soaked into wool sounds plausible for what you are experiencing.

[simply RED]

Wool is a polypeptide, nitrating it is as hard (or impossible/impractical) as nitrating a mix of aminoacids.

[DONMAN]

It looks like a big mass of casein or some other protein as Red previously stated.

[s-lab]

You need to use a +75% nitric acid. What you saw was the sulphuric acid acting on its own to in a way decompose the cotton with a little nitration to partially nitrated cellulose, the precitipate you saw.

[Cindor]

s-lab the thread is about nitrating wool not cotton.

powium why don't try renitrating it ?

[The Laughing Jackal]

I think keratin is much too large and complex of a molecule to be nitrated, cellulose is a simple hydrocarbon C6H10O5 while keratin is a 20 amino acid long protein. In all likelihood, the acids broke down the proteins into their basic peptides which a small percentage of may have had a successful nitration. I think that it is more likely that the nitric acid nitrated another component included in the wool that you used. It sounds like it burned more like potassium nitrate soaked paper more than anything. But then again, wool is fairly fire retardant. Any particular smells that went along with the burning? (hopefully not the horrid burning hair/wool smell.) I would like to know more, especially if you achieve a successful nitration. Just the name of the explosive would strike fear into the hearts of your enemies, NITROWOOL!!

[Charles Owlen Picket]

There was a time when I nitrated horn, wool, & indigo as the original picric acid experiments. I was quite successful with Indigo (->picric acid) with virtually little adjustment from a nitration of phenol. However, as I remember in those instances the material was treated w/ H2SO4 prior to the nitration - with wool and horn this technique broke them down to a virtually unusable point.

I do remember the horn issue; I used HNO3 (@70%) and allowed it to initially interact with the ground material for 3 days (this was from a text written in 1879 & reprinted). Afterward the material was nitrated in the manner typical of phenol (w/ raised temp & mixed acids). The resultant was picric acid, however the yields were quite small from the initial weight of the material. The only material that came close to phenol was Indigo in terms of weight/yeild and nitration action (the reverse; using H2SO4 as a starting point.

The point re; keratin is a good one as this is a very complex molecule and would exist within both. Most all organic materials that nitrate successfully appear simple molecules at the starting point of nitration. The above wool experiment would have come close (IMO) if the temp were monitored and perhaps raised in relation to the actions of the mixed acids.

[The Laughing Jackal]

The extremely low pH of the solution would defiantly denature keratin, Cellulose is a fairly simple organic molecule, keratin is a long chained (20 amino acids long) protein. Meaning that you would be nitrating only certain amino acid(s) and would probably not achieve a very high yield of nitrated (my guess is less than half of the acids would be nitrated) Even with monitored temperature. IF however, this by some way unbeknown to me works out - definitely something I'd like to try.

[Secong Nature]

Have you tried dissolving it in acetone to try and filter out the un-nitrated wool?