Twilight Zone Orgo Lab problem
I have an interesting separation dilemma from Orgo lab. I determined tentatively (via IR and Mass spec and my nose) that my unknown binary mixture of neutral miscible liquids consists of 2 alcohols: one is a primary alkyl [likely 1-hexanol (bp 159), plus or minus a CH2 group] and the other is benzyl alcohol (bp 205).
However, when I initially tried separating the mixture via microdistillation, the solution almost boiled over (I DID have boiling stones) but then settled down (after removing insulation) and gave distillate (seems to be same as starting material) at around 80 C (column head temp).
What is weird is that distillation left a cloudy white precipitate suspension in the boiling flask material. The same exact thing happened the second time I tried distilling the mixture (w/ boiling stones), only this time I used no insulation on the apparatus and the mixture boiled with no distillate at 35 C!
Could someone explain what's happening here? What is this white stuff? Why am I getting way, WAY off bp's? Is it that the overheating/boiling over contributed to the decomposition of one or both of these high boiling alcohols (which don't react w/ each other)? Or is it something I'm not doing right?