Synthesis and polymeritzation of 10,11-epoxyundecenoic acid

Identifier:  TFG:128

Handle: https://hdl.handle.net/20.500.11797/TFG128

Authors:  Moreno Guerra, Adrian

Abstract:
The growing awareness of society towards major environmental challenges such as global warming, increasing emissions of greenhouse gases and depleting of the earths limited petroleum reserves, are pushing the chemical industry to develop greener products and to find alternative growth strategies based on sustainable models. A particulary relevant option is to replace oil based resources by raw materials derived from renewable feedstocks. Plant oils and thereof derived fatty acids are important renewable raw materials for polymer chemistry. 10-Undecenoic acid obtained from castor oil pyrolisis is one of the most versatile plant-oil derived commercially available platform chemicals. However, the reactivity of fatty acids such as 10-undecenoic acid is limited (internal double bonds) and an alternative strategy is the functionalization before to polymerization, widening the synthetic possibilities by introducing easily polymerizable functional groups such as the epoxide group. The challenge to progressively replace fossil feedstocks by material derived from plant oils derived renewable resources is the strategy to follow and it implies not only the development of new original reactions and catalysts but also the application of well established reactions to the functionalitzation of vegetables oils. In this context, we have carried out the epoxidation of 10-undecenoic acid with differents oxidising agents and catalysts, looking for the most sustainable and eficient method for obtaining a versatible and reactive monomer (10,11-epoxyundecanoic acid). Then we polymerized this monòmer using a quaternary ammonium salt, tetrabutylammonium bromide (TBAB) as a catalyst. Finally, the fully renewable copolyester have been characterized by 1H-NMR spectroscopy, GPC and SEC.