Diamine-catalyzed urethane reaction of 1,3-propanediol with phenyl isocyanate

The urethane reaction of 1,3-propanediol with phenyl isocyanate is monitored by means of in situ FTIR. 1,4-Diazabicyclo[2.2.2]octane (DABCO) and N , N , N ′, N ′-tetramethylethane-1,2-diamine (TMEDA) are used as catalysts. Reaction rates are calculated, and reaction kinetics are studied. Furthermore, Gaussian programs are used to calculate steric configuration and electronegativity of those two diamines. The electronegativity of TMEDA is greater than that of DABCO, but the steric hindrance of DABCO in nitrogen atom is smaller. Steric hindrance plays a more important part in reaction kinetics, which makes the reaction to be catalyzed by DABCO at a faster rate. Finally, activation energy, activation enthalpy, and activation entropy for the reaction are calculated, followed by the discussion of reaction mechanism.