Benzyl alcohol was used to synthesize esters using a TiO2 catalyzed continuous flow reactor. This is a continuation of research in which temperature, flow rate, stoichiometry, column size, and collection time were varied to produce higher yields of amides from anilines. The previous research found the optimal conditions to be 200 °C, 0.25 mL/min flow rate, 1:8:1:4 (aniline:nitrile:H2O:THF) molar ratio, 5 micron fritted column, and ~2 h product collection time. In efforts to synthesize esters, these reaction conditions were explored and varied and pressure was varied. By varying these conditions, an optimal pressure was found to be a minimum of 1000 psi sustained throughout the reaction, and not exceeding 3000 psi. Esters were successfully synthesized using the reaction conditions described above, using a 1:8:4 (benzyl alcohol:nitrile:THF) molar ratio. In a related project, benzylamine derivatives were used to synthesize amides using a TiO2 catalyst and a microwave reactor. In efforts to optimize yields, the temperature, reaction time, catalyst form, presence and timing of water addition, and workup were varied. Heating the reaction mixture at 250 °C twice for 15 minutes, using TiO2 catalyst in pellet form, and adding water before the first run was found to produce the highest yields.

Synthesis of esters and amides using both flow and microwave reactors

253rd National Meeting (2017)

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