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Biobased Aldehydes from Fatty Epoxides Through Thermal Cleavage of β-Hydroxy Hydroperoxides

preprint
revised on 14.10.2020 and posted on 15.10.2020 by Thomas De Dios Miguel, Nam Duc Vu, Marc Lemaire, Nicolas Duguet
The ring-opening of epoxidized methyl oleate by aqueous H2O2 has been studied using tungsten and molybdenum catalysts to form the corresponding fatty b-hydroxy hydroperoxides. It was found that tungstic acid and phosphostungstic acid gave the highest selectivities (92-93%) towards the formation of the desired products, thus limiting the formation of the corresponding fatty 1,2-diols. The optimized conditions were applied to a range of fatty epoxides to give the corresponding fatty b-hydroxy hydroperoxides with 30-80% isolated yields (8 examples). These species were fully characterized by 1H and 13C NMR, HPLC-HRMS and their stability was studied by DSC. The thermal cleavage of the b-hydroxy hydroperoxide derived from methyl oleate was studied both in batch and flow conditions. It was found that the thermal cleavage in flow conditions gave the highest selectivity towards the formation of aldehydes with limited amounts of byproducts. The aldehydes were both formed with 68% GC yield and nonanal and methyl 9-oxononanoate were isolated with 57 and 55% yield, respectively. Advantageously, the overall process does not require large excess of H2O2 and only generates water as a byproduct.

Funding

Auvergne Rhône-Alpes region

History

Email Address of Submitting Author

nicolas.duguet@univ-lyon1.fr

Institution

Université de Lyon

Country

France

ORCID For Submitting Author

0000-0002-9425-7450

Declaration of Conflict of Interest

There is no conflict of interest to declare.

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