Sciencemadness Discussion Board

Nitrogallate, tannins- natural resources

Fantasma4500 - 18-2-2023 at 03:42

i got a bag of tannins sitting around that i extracted from wood bark, looking into uses i found it that it can be hydrolyzed into gallic acid- tho it tends to oxidize into black gunk

https://en.wikipedia.org/wiki/Gallic_acid

i only get very vague hits proving that nitrogallate can even exist- if nitrated this should be a decently stable compound, maybe TNT like properties? and... easily made from wood bark
TNT has 3 nitrogroups where nitrogallate would have 4- right? meaning higher molar weight and probably a slight bit more stable properties- and more nitrogen per carbon. better OB.
now, salicylic acid have been used directly in nitration to make trinitrophenol, maybe with a bit of hydrolysis, thermal decomposition of salicylic acid into phenol is also doable with +150*C
gallic acid however decomposes rapidly between 105 to 150*C, despite being basically phenol molecule with more hydroxy-groups on it
pyrogallol is the product of thermal decomposition mainly

https://en.wikipedia.org/wiki/Pyrogallol

nitrating that leads to- https://www.chemsrc.com/en/cas/14416-24-1_1206543.html

but only 1 nitro group? shouldnt it be possible to nitrate all the hydroxy-groups? density of just the nitropyrogallol with 1 nitrogroup is 1.77 and molecular weight of 170ish, boiling point 370*C

anything on this, any guesstimates on if tannic acid could have the potential to be interesting?

Texium - 18-2-2023 at 07:16

Quote: Originally posted by Fantasma4500  
but only 1 nitro group? shouldnt it be possible to nitrate all the hydroxy-groups?
You’ve been here over 10 years yet clearly have no idea how aromatic nitration works. Once again I implore you to go read an introductory organic chemistry textbook.

This is effectively a spoonfeeding request because you have had ample opportunity to learn the basics but instead insist on fumbling around in the dark.

[Edited on 2-18-2023 by Texium]