The optimization of the synthesis of 1-(4-vinylbenzyl) thymine (VBT) was studied using a design of experiments (DOE) approach. VBT, a bio-inspired molecule, shows promise in a variety of applications, including as a component of a polymer that can be used as a greener photoresist. When copolymerized with charged monomers, the resulting water soluble VBT copolymers can become insoluble upon UV irradiation. The average reported yield of VBT is less than 50%, resulting in wasted reagents, materials, and energy. A DOE approach is an economical, green way to analyze the effect of many factors on the yield using the minimum number of experiments possible. A fractional factorial screening experiment was performed, investigating the significance of the length of the reaction, the temperature of the reaction, the ratio of reagents, the cation of thyminate salt, the addition of water, and the amount of solvent used for the VBT synthesis. For each run, a Microwave Accelerated Reaction System was used to synthesize VBT. Automated flash column chromatography was used to purify the product, and the yield was determined using UV-Vis analysis. Through the fractional factorial design, the time, temperature, ratio, and amount of solvent were found to be significant. The subsequent full-factorial design futher investigated factors and the interactions of factors and suggested that the interaction between time and temperature was significant. The optimized time and temperature given these conditions for the synthesis of VBT will be determined through a central composite design.

Design of experiments approach to optimize the yield of 1-(4-vinylbenzyl) thymine

249th National Meeting (2015)

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