The goal of this research is to convert carbonyl compounds found in fast pyrolysis bio-oil, into unsaturated monomers for polymer synthesis. Bio-oil is a liquid product obtained through the pyrolysis of biomass containing lignin, cellulose, and hemi-cellulose. Aqueous phase of bio-oil was preferred due to presence of higher abundance of carbonyl compounds. Currently, the aqueous phase does not have much commercial value but consists of water, alcohols, aldehydes, ketones, sugar and phenols. In order to polymerize the bio-oil components, the bio-oil was altered to contain as high of a ratio of olefins as possible. In the first stage, primary and secondary alcohols in the bio-oil were converted into aldehydes and ketones, respectively by TEMPO-catalyzed oxidation. Then, through Wittig reaction, aldehydes and ketones were converted into olefins. Two different Wittig approaches were performed. Firstly, a water-mediated Wittig reaction was carried out using a stabilized ylide, which yielded an α,β-unsaturated ester from aldehydes present in the bio-oil. Secondly, Wittig methylenation reaction of aldehydes and ketones with an unstabilized ylide produced terminal olefins. Finally, the unsaturated products were polymerized by AIBN initiator at elevated temperature to build polymers.

Synthesis of unsaturated monomers from carbonyl compounds in pyrolytic bio-oil

255th National Meeting (2018)

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