I made schiff base of carbazole aldehyde using excess of aniline, now I need to purify the product. I was just wondering will my schiff base remain stable at column and aniline will come first, or will it remain stuck in the column? Any kind of help will be appreciated.
do you mean you reacted aniline with aldehyde(carbazole) and you get an Imine derivatives and you need to purification ? if yes check your rxn first by TLC to insure that your rxn accomplished then you can make the purification process.
Silica gel is slightly acidic, usually the Schiff's bases are stable under these conditions and you can separate the compounds by column chromatography.
However, few drops of triethylamine can be added before eluting the column with sufficient polarity.
Check TLC first. aniline should be on the top of the TLC plate and come out of the column much faster than the product~!
When you use solvent in which aniline is soluble then aniline will not stick up the solvent
if you want to purify your Schiff's base, and to remove unreacted aniline you should wash the column by methanol because Aniline is soluble in methanol, you can also wash your column using 60/40 methanol/water mixture
I would check what the boiling point of your Schiff base is - especially on a large scale vacuum distillation might be a favourable purification method. I made some imines before and purified them by distillation to obtain great NMRs.
I don't think it will stick because i made amide of aniline with benzoic acid some amount of aniline was left i have done column for that; aniline came first then amide as i have seen on TLC. Only t-amine will stick due to the formation of salt with acidic silica. To avoid add few drop of triethyl amine before doing column and neutralize the silica.
I think TLC is the best way to check its stickiness. Before starting Column Chromatography you should check it on Silica Plates.
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