Synthesis of norbornene via diels-alder reaction

Abstract

This thesis is concerned with the synthesis of norbornene via Diels- Alder reaction of cyclopentadiene with ethylene. For this, we have carried out preliminary thermodynamic study to estimate the preferred reaction temperature on the basis of thermodynamic properties. The calculation indicates that the postulated range of the reaction temperature is 201-272oC. In thermal reaction, the reaction performance was influenced by temperature, pressure, solvent, and initial reactant concentration. Within the scope of the present study, the optimum conditions were found to be 260oC and 1000psi with aromatic solvent and low initial concentration of dicyclopentadiene. Although catalytic reactions have also been examined to probe the viability of the catalytic reaction under mild reaction conditions, it is revealed that catalytic activities were very low and thus it seems that the use of catalyst has little advantage over the corresponding thermal reaction. The kinetic study has been performed to calculate the kinetic parameters (reaction orders and rate constants) using the postulated kinetic mechanism. The kinetic model with the estimated parameters could predict the experimental results well. From the calculated parameters at various temperatures and pressures, the apparent activation energy value and reaction orders were obtained. The apparent activation energy of Diels-Alder reaction of cyclopentadiene with ethylene was found to be 59 ± 3 kJ/mole, and empirical orders of the reaction with respect to the partial pressure of ethylene and the concentration of cyclopentadiene were estimated to be 1.09 ± 0.03 and 0.84 ± 0.02, respectively.