[ericandrews]

Referring to http://bama.ua.edu/~kshaughn/chem232/resources/mechanisms/review/imine/imine1.htm

Summary, acetone (and other ketones) reacts with Amine to form imine. The mechanism above is acid catalysed. My questions are (all ideas welcome, need not have an answer set in stone..) Does this happen without acid present ? The acid in this mechanism is H3O+. You guys think I'd get imine formation if I could keep out moisture ? Solution goes from clear to clear yellow tinged. Does this sound right for an imine ? I wasn't able to find any absorption data on imines. Once the imine is formed, its reversible, any ideas on reversing it or  just keeping the equilibrium favouring no imine formation ?
I really need help on this one.
Cheers, Eric.

[Yggdrasil]

In most cases, you will use an acid catalyst in the formation of imines from amines and ketones.  However, it generally isn't done in the presence of aqueous acid (H₃O⁺).  The reaction is reversible, and since water is a prodcut of imine formation, the presence of water in the reaction will shift the equilibrium to favor the reactants (in fact, aqueous acid is used to hydrolyze imines back to amines and ketones).  A lot of the time, I see glacial acetic acid used as a solvent for imine formation since it is an anhydrous acid.