Reactions of Aldehydes and Ketones and Their Derivatives

Murray, Brian A.

doi:10.1002/9781118707838.ch1

Cited by 2 publications

(1 citation statement)

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“…Aldehydes are ubiquitous in organic chemistry as they serve as platform towards other organic functions such as alcohols, carboxylic acids, acetals, imines, amines, and many others. [1] For several years now, the production of bio-based buildingblocks from biomass as a renewable feedstock has become the subject of very intense research. [2] Contrary to carboxylic acids, only a few bio-based aldehydes are readily accessible from renewable resources.…”

Section: Introductionmentioning

confidence: 99%

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

Miguel¹,

Vu²,

Lemaire³

et al. 2020

Preprint

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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.

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Section: Introductionmentioning

confidence: 99%