Mass Spectrum and Thermal Behavior in Solid State of N,N-Di(1-hydroxyalkyl)-2-imidazolidinone

Abstract

Abstract 1,3-Bis(1-hydroxyalkyl)-2-imidazolidinones (1) were prepared by the reaction of imidazolidinone with propyl-, butyl-, isobutylaldehyde. They were unstable and moisture-sensitive substances, except for 1,3-bis(1-hydroxybutyl)-2-imidazolidinone (1c). In the decomposition by the electron impact of 1 and the dimer of 1c, the molecular ion peak of 1 was not detected. The fragmentation of the imidazolidinone ring was considered to take place after a successive cleavage of the two side chains of 1. The pyrolysis reaction of 1 was found to be a thermal decomposition via a molten state after a condensation reaction. The order of the pyrolysis was calculated on the basis of DSC curves. The condensation stage for 1c apparently obeyed 1/2-order kinetics. From the dependence of the velocity on the temperature in DTA and the thermogravimetric analysis, the activation energy of decomposition was calculated; the value for the former was 67 and the latter 73 kJ mol−1. The mechanism of pyrolysis was supported by the results of the IR spectrum and chemical analysis.