7297-29-2

Upstream product

• 1115-01-1 methyl 9,10-dihydroxy stearate 
• 120-87-6 Dihydroxystearic Acid 
• 112-62-9 Methyl oleate 

Downstream Products

• 124-19-6 nonan-1-al 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 67136-05-4 dimethyl 9-hydroxy-10-oxooctadecanedioate 
• 4444-91-1 methyl 9-hydroxy-10-oxostearate 

Relevant academic research and scientific papers

Homogeneous and heterogeneous catalytic (dehydrogenative) oxidation of oleochemical 1,2-diols to α-hydroxyketones

Herein, the preparation of methyl oleate α-hydroxyketone from the corresponding 1,2-diol was investigated using both homogeneous and heterogeneous systems. Homogeneous conditions using a Pd(OAc)2/neocuproine complex were first developed using oxygen as a sole oxidant under mild conditions (MeOH, 50 °C). Under these conditions, the conversion of diol reached 95%, and α-hydroxyketone was obtained with 97% selectivity. The access to α-hydroxyketone has also been studied by dehydrogenation using a range of heterogeneous catalysts under solvent-free conditions at high temperatures (160-180 °C). Dehydrogenation using activated Ru/C under vacuum provided α-hydroxyketone with 93% conversion and 82% GC yield. The optimized conditions were applied to a range of oleochemical diols, including a vegetable oil derivative, to obtain the corresponding α-hydroxyketones with up to 74% isolated yields.

Efficient ruthenium-catalysed oxidative cleavage of methyl oleate with hydrogen peroxide as oxidant

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. The Royal Society of Chemistry.