Sustainable Synthesis of Allylic Ethers of Relevance for Biomaterials

University essay from KTH/Skolan för kemi, bioteknologi och hälsa (CBH)

Abstract: Lignin is the most abundant source of naturally occurring aromatic compounds but has mainly been considered as waste material or energy source in the pulp and paper industry. However, due to the drive to find new material applications derived from renewable resources, there are extensive research activities aiming to develop new routes to utilize this source toward novel polymer materials. In this project, cinnamyl alcohol was used as a benchmark substrate in determining the most favorable reaction conditions for the optimal dehydrative etherification of allylic alcohols. The optimal reaction conditions determined for cinnamyl alcohol aimed to be applied to the etherification of the structurally similar, lignin-derived coniferyl alcohol to produce a bio-based allylic ether of relevance for biomaterial applications. However, due to the COVID-19 pandemic, the investigation of the etherification of coniferyl alcohol could not be conducted and the project had to be limited to the synthesis of 2-phenylethyl cinnamyl ether. Thus, this project serves as a pre-study for the sustainable etherification of lignin-derived allylic alcohols of relevance for biomaterials. The optimal reaction conditions for the synthesis of 2-phenylethyl cinnamyl ether was concluded to be 0.25 M cinnamyl alcohol and 1.00 M 2-phenylethanol as initial concentration of the reactants, 0.02 M Zr(Cp)2(OTf)2 ∙ THF as initial concentration of the catalyst, benzotrifluoride as solvent, a reaction mixture temperature of 60 °C, and a reaction time of four hours. Using optimized reaction conditions, coniferyl alcohol, a lignin-derived allylic alcohol, could in further research be evaluated as a sustainably sourced allylating agent with potential for biomaterial purposes.

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