53951-43-2Relevant articles and documents
Selectivity Switch in the Aerobic 1,2-Propandiol Oxidation Catalyzed by Diamine-Stabilized Palladium Nanoparticles
Oberhauser, Werner,Evangelisti, Claudio,Capozzoli, Laura,Manca, Gabriele,Casaletto, Maria Pia,Vizza, Francesco
, p. 2896 - 2906 (2021/05/06)
Palladium nanoparticles stabilized by a sterically demanding secondary diamine ligand have been synthesized by hydrogen reduction of a palladium acetate complex bearing the corresponding diimine ligand. The obtained nanoparticles were used to catalyze the aerobic oxidation of 1,2-propandiol in n-hexane, and after their heterogenization onto a high surface area carbon, in water. In n-hexane (2,4-dimethyl-1,3-dioxolan-2-yl) methanol has been obtained as major product, whereas in water acetic acid with a selectivity of >85 % has been achieved. The selectivity switch observed was a clear induced by water. The robustness of diamine-stabilized palladium nanoparticles under real aerobic oxidation conditions has been proved by recycling experiments, TEM measurements of the recovered catalysts and by comparison of its performance with that of palladium nanoparticles generated by the metal vapor synthesis technique and supported onto the same carbon in the absence of the stabilizing diamine ligand.
Oxidation of Diols and Ethers by NaBrO3/NaHSO3 Reagent
Sakaguchi, Satoshi,Kikuchi, Daisuke,Ishii, Yasutaka
, p. 2561 - 2566 (2007/10/03)
NaBrO3 combined with NaHSO3 was found to be an excellent oxidizing reagent of alcohols, diols, and ethers under mild conditions. A variety of aliphatic and cyclic diols were selectively oxidized with satisfactory yields to the corresponding hydroxy ketones and/or diketones, which are difficult to selectively prepare due to a concomitant formation of cleaved products. For example, 2-hydroxycyclohexanone and 1,2-cyclohexanedione were selectively formed by allowing 1,2-cyclohexanediol to react with NaBrO3/NaHSO3 reagent in a selected solvent. On the other hand, an alkyl ether, such as dioctyl ether, reacted with NaBrO3/NaHSO3, in water at room temperature to give octyl octanoate in 82% yield. The same oxidation at higher temperature (60°C) produced the α-brominated ester, octyl 2-bromooctanoate, which is considered to be formed through an alkenyl alkyl ether as the intermediate. The treatment of 1-ethoxy-l-heptene with NaBrO3/NaHSO3 afforded ethyl 2-bromoheptanoate and 2-bromoheptanoic acid as the major products.