A comparison of participating solvents during ozonization

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Abstract
Sixteen different participating solvents and certain combinations thereof were evaluated for their effects on the conversion of methyl oleate to carbonyl compounds by ozonolysis. Depending upon the alcohol or carboxylic acid used as a single solvent, chemical reduction with zinc and acetic acid gave yields of 70舑100%; catalytic hydrogenation with 10% Pd/C, 62舑84%. When equimolar mixtures of an acid and a primary, unhindered alcohol were used, catalytic hydrogenation gave yields of 94舑98%. In preparative scale experiments, catalytic hydrogenation gave 98% yields of methyl azelaaldehydate in the representative solvent combinations of 2‐methoxyethanol/acetic acid and 1‐butanol/propionic acid. When anhydrous calcium sulfate was used as a drying agent for aldehyde/alcohol solutions significant acetal was formed in the absence of other catalysts.