Why not run a test column…with ACID , perhaps HCl just to protonated the supposed “amine” …and trap it in the water phase.
Evaporate a portion of the water phase in the rotovap…
And Bingo…the amine salt is in the jar. Identify it.
The problem I see…are volatile amines…for instance you can certainly smell an aqueous ammonia solution.
But if you protonated it with HCL you can not….???
Just a thought…
I still don’t get the mole fraction aspect of the amine hypothesis.
Open minded….
If you were to prepare the cyclohexamine salt…and then run it standard procedure HPLC RP DAD…will you see the counter ion on that gradient?
Can we purposefully poison a crystallization proceed …like the
Pentane you did with known amine…?
As such…in design we have to sit down and think about what we are doing…as just adding amine changes pH and ionizations state of COOH.
And are we looking for a “non ionic “. H-bonded complex….?
Do we have a clear picture up on the board?
Whether or not we salt it out, collecting the culprit in water IS being done! I have requested of those who water wash their butane (or their 13X mol-sieves) to concentrate a volume of water with ‘wtfamine’ by using that volume as the first in every set of multiple washes. If the volume is large enough, you can be sure that I will take samples of it to run several different experiments!