Abstract
The liquid phase hydrogenation of 2-((1-benzyl-1, 2, 3, 6-tetrahydropyridin-4-yl)methylene)-5, 6-dimethoxy-2, 3-dihydroinden-1-one hydrochloride (1) over a 5 % Pt/C industrial catalyst was studied experimentally in a batch slurry reactor using methanol as a solvent. The catalyst was characterized by the adsorption techniques for specific surface area and pore volume, and by XRD for crystallinity. To investigate the intrinsic kinetics of the reaction, the effect of temperature, catalyst loading, hydrogen partial pressure and (1) concentration on the initial rate of hydrogenation was studied. The analysis of initial rate data showed that the gas-liquid, liquid-solid, and intraparticle mass-transfer resistances were not significant. The reaction scheme of (1) hydrogenation was proposed for the kinetic modelling. Apparent rate constants for all hydrogenation steps were calculated using a first order kinetic approach resulting in good agreement between the experimentally obtained and predicted concentrations. From the temperature dependence of rate constants, the activation energies of various reaction steps were calculated. The averaged activation energy of these steps was found to be 31.1 kJ mol-1.
Highlights
Selective catalytic hydrogenation of double and triple carbon-carbon bonds is one of the fundamental reactions for the synthesis of fine and industrial chemicals
Order at high concentrations of the substrate. These results indicate the non-linear behaviour of the rate of [1] hydrogenation, which is characteristic of a surface controlled reaction
The hydrogenation of 2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride [1] to 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride [4] using a 5 % Pt/C catalyst was studied in a batch slurry reactor in a temperature range of 298 – 318 K using methanol as solvent
Summary
Selective catalytic hydrogenation of double and triple carbon-carbon bonds is one of the fundamental reactions for the synthesis of fine and industrial chemicals. This important area of catalytic chemistry has been the foundation for the development of numerous diverse, small- and large-scale commercial hydrogenation processes, which include synthesis of fine and specialty chemicals such as agroche micals, flavours and fragrances, food additives and pharmaceuticals. The reaction product is applied in the treatment of all kinds of senile dementia. It is useful for prevention and treatment of Alzheimer’s disease by virtue of its acetyl cholinesterase inhibitory action. There are many processes described mainly in patent literature for producing [4] and its phar-
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