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Study on the reaction of 4-allyloxybutane-1-ol with ruthenium (II) complexes

Urbala M.

Polish Journal of Chemical Technology

2005

Vol. 7, nr 4

48-50

The allyl ether systems undergo double-bond isomerization to 1-propenyl ethers in the presence of phosphine ruthenium (II) complexes very smoothly and effectively. However, when functionally substituted allyl ether derivatives are used as the substrates, the course of the reaction of the substrate with a metal complex is substantially determined by the complexing ability of the functional group. The reaction of allyl substrates containing primary hydroxyl group (allyloxyalcohols) with phosphine ruthenium (II) complexes (i.e. [RuClH(CO)(PPh3)3], [RuCl2(PPh3)3]) has been investigated. It was found that this reaction leads selectively to either 1-propenoxy alcohols or to cyclic 2-ethyl-[1,3] acetals, depending on the complex used as a catalyst and the reaction conditions. For the model isomerization of 4-allyloxybutan-1-ol, the optimal parameters for highly selective and efficient synthesis of 4-(1-propenyloxy)butan-1-ol or 2-ethyl-[1,3]dioxepane are 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.

The synthesis of 1-propenyl ethers and their photopolymerization

Martysz D., Urbala M., Antoszczyszyn M.

Polish Journal of Chemical Technology

2001

Vol. 3, nr 3

25-26

The di(l-propenyl) ether has been observed to be a highly reactive monomer in photoinitiated cationic polymerization undergoing very high conversions to polymer at very short irradiation times. The polymerization process was investigated for various UV-systems containing: the model 1-propenyl ether 1,4-dipropenoxybutane, the epoxy resin Epidian 6 or the unsaturated polyester resin Estromal 103 and cationic or radical initiator. The amounts of ether and initiators were changed in compositions.

Non-waste synthesis of 1-propenoxyl monomers

Urbala M., Antoszczyszyn M., Krompiec S.

Polish Journal of Chemical Technology

2001

Vol. 3, nr 3

22-24

Non-waste synthesis of 1-propenoxyl monomers of C4 diols ((Z)-butane-2-ene-l,4-diols) via isomerization of the corresponding allyl ethers of diols catalysed by the ruthenium(II) complexes has been investigated. [RuHCl(CO)(PPh3)3] is a very active and selective catalyst precursor of isomerization of allyl ethers of diols, containing neither a triple bond nor unprotected primary allylic hydroxyl group. The optimal parameters for the synthesis of 1-propenyl ethers and their physic-chemical properties ('H NMR, MS, boiling point) are given. Synthesized propenyl ether monomers were of high purity, therefore, they are suitable directly for use in photointiated cationic polymerization.