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Author: Subject: IPA + Sulfuric acid -> red color
biomechem
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[*] posted on 1-8-2017 at 13:59
IPA + Sulfuric acid -> red color


Why does the mixture of IPA with H2SO4 left for some time turns into red color?

I thought of oxidation IPA to acetone, and then aldol rxn but I think it would give too short-chained products to change color its.
On the other hand maybe it is just deprotonation of IPA and carbocation reacts further, making it polymerising?

Any ideas, suggestions?

MeshPL
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[*] posted on 2-8-2017 at 02:43


I can try it to see if my IPA will do the same if left to sit with H2SO4.

Edit: it indeed works. I used about 20 ml of IPA and 20ml of H2SO4. The mix instantly turned red-brown and than black. It heated up considerably, emited some bubbles and also some white fumes at first. It smelled like IPA, though. Once the mix cooled I poured it into water. The resulting solution was murky, brown and a brown layer started to separate on the top of aquous layer. It smells differently than IPA. I would describe the smell as "fresh, somewhat like a citrus, somewhat like fresh grass and a bit like an aromatic solvent. In fact it was kind of pleasant. Kind of.". That's all I can do at the moment. Once the school year starts, I could do some other tests including iodoform test, bromine water test or sth.

I used some "extracting gasoline" (that's how we call a really voltaile hydrocarbon based solvents here) to extract all organic stuff from aquous layer, but it nevertheless stayed orange and murky. Organic layer is yellow and fully transparent.

Now the gasolne has evaporated somewhat and organic layer looks brown.

[Edited on 2-8-2017 by MeshPL]

[Edited on 2-8-2017 by MeshPL]

[Edited on 2-8-2017 by MeshPL]

[Edited on 2-8-2017 by MeshPL]

[Edited on 3-8-2017 by MeshPL]
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