Taking Control! The binary catalyst system composed of MoO3 and an organic phoshponium salt [Bu4P]X proved very efficient to produce oleochemical cyclic carbonates from renewables.

No abstract

The oxidative cleavage of alkenes leads to the formation of carboxylic acids. One of the few technical processes using this reaction is the production of azelaic acid via the ozonolysis of oleic acid. Because of the need for stoichiometric amounts of the expensive oxidant ozone, together with safety hazards, there is still a requirement for a catalytic process using a cheap and environmentally friendly oxidant. In the present work, the oxidative cleavage of methyl oleate by hydrogen peroxide was catalysed by an easily available ruthenium precursor with dipicolinic acid as ligand. The systematic optimisation of the reaction led to the formation of azelaic acid monomethyl ester in high yields amounting to 86%. The investigation of the reaction pathway showed that the reaction proceeds via a tandem reaction of epoxidation and hydrolysis of the epoxide and oxidative cleavage of the vic-diol.

4(5)‐(Hydroxymethyl)imidazole and potassium iodide were identified as an efficient catalyst system for the cycloaddition of epoxides and carbon dioxide producing 1,3‐dioxolan‐2‐one derivatives under solvent‐free conditions. The high activity of the catalyst system even at 60 °C was probably due to synergistic effects between potassium iodide and the substituted imidazole. Various functionalized and nonfunctionalized terminal epoxides as well as internal epoxides were converted into the corresponding cyclic carbonates in high yields (up to 99 %) under mild reaction conditions within a short reaction time. Compared with the previously reported amino alcohols e.g. triethanolamine based catalyzed synthesis of cyclic carbonates, the catalyst system described herein demonstrates a higher activity toward a broad substrate scope

The transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide was investigated using Ru(acac)3/dipicolinic acid as catalyst. Under optimised reaction conditions, the epoxidised methyl oleate 2 was obtained with a quantitative yield in short reaction time and under mild reaction conditions.Practical applications: Epoxidised fatty acids and their derivatives are produced by the Prilezhaev reaction and used in various applications in the chemical industry. Due to the known drawbacks of epoxidation with peroxy acids, such as hazardous handling of peracids in large quantities or the decrease of epoxide selectivity due to the formation of undesired by‐products in the acidic medium, the epoxidation of fatty acid derivatives using more convenient oxidants is still a subject of research interest. Herein, we present a simple procedure for the transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide in quantitative yields, and under mild reaction conditions, as a potential alternative for the production of epoxidised fatty acid derivatives.