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Robust Organocatalysts for the Cleavage of Vegetable Oil Derivatives to Aldehydes through Retrobenzoin Condensation
Author(s) -
Vu Nam Duc,
Bah Souleymane,
Deruer Elsa,
Duguet Nicolas,
Lemaire Marc
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800091
Subject(s) - chemistry , cleavage (geology) , organic chemistry , nonanal , distillation , sunflower oil , medicinal chemistry , materials science , fracture (geology) , composite material , biochemistry
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.