Industrial & Engineering Chemistry Research, Vol.55, No.14, 3890-3899, 2016
Catalytic Hydrogenation of 2-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydroinden-1-one Hydrochloride: Fractal-like and Weibull Model Kinetics
The hydrogenation of 24(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3-di-hydroinden-1-one hydrochloride (1) over a 5% Pt/C industrial catalyst is strongly influenced by solvents (methanol, ethanol, acetone, water) and reaction conditions such as temperature, catalyst loading, hydrogen partial pressure, and compound 1 concentration. The solvent has a strong influence on hydrogenation of compound 1 on a Pt/C catalyst. Different physical and electronic properties (given as molecular descriptors) of nonreactive solvents were related to the fractal-like and Weibull model kinetics parameters. The best relation was established between the fractal kinetic index, h, and the solvent H-bond acceptor ability (represented by the Abraham descriptor B, the solute hydrogen-bond basicity). The apparent activation energy of hydrogenation step was determined to be 20 kJ mol(-1). The fractal-like and Weibull model kinetic terms indicate that the formation of 24(1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride, compound 2, can be correlated with the complex distribution of the reactive species.