14 Apr
14/04/2020 09:30

Sciences & Société

Soutenance de thèse en visioconférence totale : Lianjie WANG

New biobased chemicals from HMF and GMF: Applications of Morita-Baylis-Hillman reaction and nitrone 1,3-dipolar cycloaddition

Doctorant : Lianjie WANG

Laboratoire INSA : COB ICBMS
Ecole doctorale : ED206 : Chimie de Lyon

In recent years, the design of new fine chemicals from biomass and platform molecules has become a very active field of research. 5-Hydroxymethylfurfural (HMF) is considered as one of the most promising renewable building blocks and its glucosylated analogue glucosyloxymethylfurfural (GMF) is also an interesting biobased furanic aldehyde able to provide a range of novel architectures which include a remaining full carbohydrate moiety.
This thesis is a contribution to the use of these two building blocks in the design of novel fine chemicals, using Morita-Baylis-Hillman reaction and cycloaddition of nitrones. The application of these strategies for designing novel surfactants was also investigated.
First we investigated the MBH reaction of HMF and GMF with cycloalkenones using pure water. New functionalized scaffolds have been prepared in mild and safe conditions with remarkable atom-economy by this route used for the first time. Then we investigated another medium issue which is the possibility to run MBH reactions of HMF and GMF with acrylates or other alkenes in absence of any solvent. After that, we investigated the 1,3- dipolar cycloaddition reactions of nitrones obtained from HMF and GMF, offering novel synthetic routes towards biobased isoxazolidines.
In the last part, we addressed the possibility to use these two routes for the design of novels biobased surfactants. Preliminary results on their surfactants properties have been obtained, and indicate a real interest of these compounds which exhibit easily adjustable properties based on simple structural variations, and are obtained in an easy straightforward and original synthetic sequence.