A strategy of one-pot regioselective cohydrogenation of styrene oxide (STOX) and aryl alkenes (styrene and alpha-methylstyrene) in the presence of aralkyl alcohols (1-phenylethanol and 2-phenyl-2-propanol) is proposed. It would help reduce capital and operational expenditure in the aralkyl hydroperoxide-based 2-phenylethanol (2PEA) manufacturing process. Reactions are performed in a stirred tank reactor in the presence of a 5% Pd/C catalyst. A range of operating conditions are proposed wherein STOX is converted to 2PEA, whereas the aryl alkenes are converted to their corresponding alkylbenzenes. Interestingly, the rate of hydrogenation of STOX is much slower than the rapid hydrogenation of the aryl alkenes. The kinetic model for the reaction is proposed based on the experimental data, and the associated parameters are estimated by nonlinear regression. The apparent activation energy for STOX hydrogenation over the range of operating conditions is calculated as 47.65 kJ mol–¹. The estimated kinetic parameters are apposite for the technocommercial feasibility study and subsequent scaling-up issues of the aralkyl hydroperoxide-based novel scheme of 2PEA production. Based on the observations, conceptual flowsheets for 2PEA manufacturing using cumene hydroperoxide and ethylbenzene hydroperoxide are also proposed.
Read full abstract