Characterization of Aniline-Acetone Condensation Products by Liquid Chromatography and Mass Spectroscopy

Abstract

Liquid chromatography has proven to be an extremely valuable tool for many separations involving polymers and polymer chemicals, especially when used in conjunction with mass spectroscopy for chemical identification. The complex products of the condensation reaction of aniline with acetone have been characterized by liquid chromatography and mass spectroscopy. The LC separation procedure utilized a C18 Micro Bondapak (reverse phase) column with a water/tetrahydrofuran gradient system. Eluted peaks were trapped individually for field desorption mass spectral identification. Syringe deposition was used to transfer the isolated components to the field emitter. The major components found in the reaction mixture were oligomers of 2,2,4-trimethyl-l,2-dihydroquinoline (TMDQ), although several other monomeric and oligomeric side-products were observed and characterized. Forty-two components were identified in the product resin. These can be classified into eight major series of oligomers; all series have oligomers separated by the TMDQ monomer unit (173 amu).