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.