Date of Award
Master of Science
Amines have broadly applied in the pharmaceutical and fine chemical industries, which cause intense research for developing efficient methods to produce primary, secondary and tertiary amines in organic synthesis. N, N-dimethyl tertiary amines are useful as catalysts which are buffers on the analysis of peptides and proteins. This transformation proceeds via an active C-N bond, and the most attractive method to produce amines is the reductive amination of carbonyl compounds. This method involves two steps, the condensation of aldehyde and the subsequent imine hydrogenation in the presence of a hydrogen donor. The synthesis of a catalytic, light-driven process for the reductive amination of native Biomass in the presence of heat is considered.
Use of amide as the nitrogen donor and reductant require high temperature. Materials containing zirconium are used as superionic conductors in oxygen sensors, fuel links, and as catalysts of "secondary generation." The catalysts applied in environmental protection, petrochemistry, electrocatalysis, polymerization, etc. Zirconium dioxide is an essential component of the Lambda probe (oxygen sensor) and a significant component of catalysts used in fume purification (three-way catalysts (TWC)) for catalytic fuel combustion, etc. Zirconium dioxide can be applied in the catalysis as a single unit or as a component of compound catalysts. Zirconium dioxide characterized by high chemical resistance is stable at a wide temperature range. It possesses both acidic and basic centers. Its properties enable surface processes as a mechanism of bifunctional acid-base catalysis. The number of acidic and basic centers can be changed using proper preparations in ZrO2 synthesis. All polymorph types of ZrO2 are used in catalysis.
In this study, the researcher developed in the presence of a heterogeneous zirconium-based catalyst in which N, N-dimethylformamide at 180°C was used as the solvent, a low molecular weight amine source and a reductant. Aromatic tertiary amines, 3,4-dimethoxy, N, N-dimethyl benzylamine have been produced from starting materials lignin-derived from grass aromatic aldehydes via the Leuckart reaction using ZrO2 as a catalyst. Approximately 94% yield of the tertiary amines were achieved over a straightforward step for the preparation. The reusability of Zirconium dioxide as a catalyst for the system was studied by using the same zirconium for the conversion of Veratraldehyde to tertiary amine at 600°C for 4h by consecutive addition of Veratraldehyde in six catalytic cycles. The catalyst remains active for the six periods with an 86% yield. All results were fully characterized by 1H and 13C nuclear magnetic resonance spectroscopy and Infrared (IR) spectroscopy.
Ananda S. Amarasekara
Prairie View A&M University
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Date of Digitization
John B Coleman Library
City of Publication
Delfan, S. (2020). Studies on the Conversion Cyclic Aldehyde to Aromatic Amine by Reductive Amination. Retrieved from https://digitalcommons.pvamu.edu/pvamu-theses/1478