This question about boiling milk reminded me of my everyday lab work at the rotavap: Some solvents and solutes are feared for the intense bubbling they create while the solution is boiling — be it at ambient pressure like the milk or at reduced pressure in the rotavap. For most of the infamous solvents, the bubbles will even create a somewhat stable foam (that usually ends up on the wrong side of the rotavap).
Well known in my lab are dissolved triphenylphosphane and the solvent toluene while isohexane (‘mixture of hexane isomers including methylcyclopentane’) is known to hardly ever give bubbles.
Why is this so? Why are bubbles often so much more stable even for just a solvent (toluene)?