OK, so SWIM had some ketone that for some reason or another had to be buried offsite for a while. He didn't bury it below the frost line, so the ketone was exposed to temperature fluctuations throughout the summer and extremely warm winter. He finally decided it was time to aminate the oil 6 months later with an Al/Hg nitro reaction. everything went like it supposedly should have through the reaction. At the end, the product was basified, extracted with 500ml + 200ml + 150ml xylene, washed 4x with 300ml dH2O, 2x with 300ml NaCl solution, and then dryed with baked epson salts and filtered. A gassing apparatus was then used to gas out the oil. At first, gas went in and turned the NP slightly yellow. Crystals then started to form and immediately drop to the bottom, and then SWIM overgassed his product and the xylene turned red. A couple of minutes later, the crystals turned into a red oil and dispersed throughout the xylene. So SWIM added 75ml dH2O and shook in a separatory funnel to reclaim the crystals, and proceeded to evaporate them out. He was left with a red tar that upon repetitive acetone washes produced a little under 6g of extremely light powder that's not very crystalline in nature, has no noticeable smell over the acetone, and has no taste! Do anyone have any ideas what he might have? He thinks it could possibly be a problem with the ketone being stored so long, since it had a somewhat different smell than it had originally and was a darker yellow than before.
Sed quis custodiet ipsos custodes?