basic chem questions

[drainlife20]

Would a stb extract with sodium hydroxide have lye contamination even after recrystallization? Sodium hydroxide doesn't seem to be soluble in heptane. SWIM isn't sure if it is after dissolving in water(no chemistry knowledge=experiments for everything), and the heptane is in the freezer right now. But it didn't dissolve at all in room temp heptane, at least I couldn't see anything happening. I'm guessing a base can't dissolve in a non-polar solution? Or maybe at least sodium hydroxide can't? MY MIND IS A BLANK CANVAS! Sorry for the very basic questions, and just a warning, if you guys answer this, then I'm going to be asking you a whole lot more

 

[drainlife20]

Yeah it's adding up pretty quickly. I'm convinced that it's a tannate. If this is the case, like you said, it would help explain why weaker bases have lower yields. Sodium hydroxide doesn't really break the bark down very well, maybe if you leave it sitting for a month, but most the STB techs are for fast results involving as little time as possible, so that kind of throws that argument out the window. But the NaOH "cleaving" the tannate salts as that quote suggests, yeah, I'm convinced.