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Robust Organocatalysts for the Cleavage of Vegetable Oil Derivatives to Aldehydes through Retrobenzoin Condensation

Nam Duc Vu 1 Souleymane Bah 1 Elsa Deruer 1 Nicolas Duguet 1 Marc Lemaire 1
1 CASYEN - Catalyse Synthèse et Environnement
ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
Abstract : A series of thiazolium salts was prepared and tested for the cleavage of the α-hydroxyketone derived from methyl oleate. The robustness of these precatalysts was determined by dynamic thermogravimetric analyses (TGA). It has been shown that the stability of these species is mainly governed by the nature of the counter-anion and some of them were found to be stable until 350–400 °C. The α-hydroxyketone derived from methyl oleate was cleaved under reactive distillation conditions using optimized, thermally robust N-butylthiazolium triflate to give the cleavage product, namely, nonanal and methyl azelaaldehydate, with 85 and 70 % yields. A range of α-hydroxyketones derived from several fatty acids was cleaved to give the corresponding bio-based aldehydes with up to 98 % isolated yields. Finally, this protocol was successfully applied to a high-oleic sunflower oil derivative.
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Nam Duc Vu, Souleymane Bah, Elsa Deruer, Nicolas Duguet, Marc Lemaire. Robust Organocatalysts for the Cleavage of Vegetable Oil Derivatives to Aldehydes through Retrobenzoin Condensation. Chemistry - A European Journal, Wiley-VCH Verlag, 2018, 24 (32), pp.8141-8150. ⟨10.1002/chem.201800091⟩. ⟨hal-02128568⟩

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