Synthesis of α-methylenlactones and α-methyleneenaetal lactones as blocks of hard blocks in ABA block copolymers

Identifier:  TFG:2628

Handle: https://hdl.handle.net/20.500.11797/TFG2628

Authors:  Segarra Casaldàliga, Alba

Abstract:
Elastomeric thermoplastics are a type of polymers that predominantly form ABA block copolymers. These copolymers have a structure segregated into two phases that form the hard block and the soft block. This work focuses on synthesizing monomers, which will constitute the hard block, from renewable sources and have a certain degree of degradability. The monomers that wish to be synthesized are the following: Tulipalin A has been synthesized by means of a condensation of ethyl formate and γ-butyrolactone using the NaH as a base followed by a nucleophilic paraformaldehyde attack. The α-methylene-1,3-dioxolan-4-one has been synthesized following a synthetic pathway three steps. The first step was the condensation of lactic acid and formaldehyde catalysed by para-toluenesulfonic acid forming 5-methyl-1,3-dioxolan-4-one. The second step was bromination in α to carbonyl using NBS and AIBN. The last step was the elimination using a base of Et3N or DBU. The 2-methyl-1,3-dioxan-4-one was synthesized from the Bayer-Villiger oxidation of the furanone of coffee using the MCPBA as an oxidizing agent.