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Technological aspects of synthesis of poly(ethylene glycol) mono-1-propenyl ether monomers

Urbala Magdalena

Polish Journal of Chemical Technology

2020

Vol. 22, nr 3

55--63

For the first time, the technological aspects of the highly productive and selective synthesis of UV-reactive poly(ethylene glycol) mono-1-propenyl ether monomers was developed. The solvent-free isomerization of model commercial available 2-allyloxyethanol and allyloxypoly(ethylene glycol) derivatives, type Allyl–[OCH2CH2]n–OH, n = 1–5, into a 1-propenyl derivative under the homogeneous catalysis conditions using the ruthenium complexes were evaluated. The effect of a various reaction conditions (i.e. the concentration of [Ru] complex, the reaction temperature, reaction gas atmosphere) together with trace amounts of allyl hydroperoxides formed via autoxidation reaction of allyl substrates on the productivity of catalyst was examined in detail. Moreover, the significant role of the allyl substrate structures on the catalytic activity of ruthenium catalysts were also recognized. The optimal parameters of the scaled-up synthesis together with productivity of catalyst were first established.

The isomerization of 1,4-diallyloxybutane catalyzed by [RuClH(CO)(PPh3)3] - the effect of reaction conditions

Urbala M.

Polish Journal of Chemical Technology

2004

Vol. 6, nr 2

59-61

The model isomerization reaction of 1,4-diallyloxybutane catalyzed by [RuClH(CO)(PPh3)3] has been studied. This reaction practically solely leads to the formation of 1-propenyl derivatives in mild and solventless reaction conditions. A mixture of isomer products, i.e. (Z,Z)-, (Z,E)-, (E,E)-l,4-di(l-propenyloxy)butanes is formed. The effect of the reaction conditions on the yield of 1-propenyl ether and the isomers contents was examined. The temperature, the catalyst concentration, the atmosphere of the reaction gas (air or inert gas) and the reaction time were changed. From the viewpoint of a minimal concentration of ruthenium pre-catalyst, the optimal parameters for the quantitative synthesis of 1-propenyl ether have been determined. Additionally, the 100%-yield reaction time was evaluated depending on the temperature and ruthenium pre-catalyst concentration.