[limpet chicken]

A fair while ago, I tried a bit of an experiment, must have been a year or two ago, but the result still perplexes me somewhat as to what the probable reaction pathway might have been.

I passed a constant stream of hydrogen selenide, generated by heating a mixture of powdered elemental Se with parrafin wax, so there may have been some traces of hydrocarbon vapor in there, probably not much though, into heated anhydrous 2-propanol, with a small amount of conc. H2SO4, at the time I was hoping that H2Se was acidic enough to form an ester with the isopropanol, well, it didn't, or at least I don't think it did, as I would have expected a pretty horrendous stench if it had formed a selenol, or just perhaps, for the H2Se to behave as a reducing agent, reducing alcohol to alkane, which obviously didn't occur as the product remained polar.

What did happen though, was a deep blue color change to the IPA, at the time I didn't attempt any more tests on it, as the tubing which I was bubbling  the hydrogen selenide through the alcohol with melted through, spewing H2Se everywhere, leaving me busy with a blowtorch, burning it off as it formed.

What gets me, is what sort of reaction products might have formed, to give that blue color, I can't really start to make an educated guess going by the color, as I don't really know much about organoselenium derivatives at all.