26424-32-8Relevant academic research and scientific papers
Hydroxy functional acrylate and methacrylate monomers prepared via lipase-catalyzed transacylation reactions
Popescu, Dragos,Hoogenboom, Richard,Keul, Helmut,Moeller, Martin
experimental part, p. 80 - 89 (2010/08/20)
Candida antarctica lipase B (CAL-B, Novozyme 435) catalyzes the transacylation of methyl acrylate and methyl methacrylate with diols and triols in 2-methyl-2-butanol at 50 °C. Under the experimental conditions, up to 70 mol% of the acyl donor methyl acrylate was converted. Methyl methacrylate is the less efficient acyl donor (up to 60 mol%) due to the higher sterical hindrance in the enzymatic transacylation. Under the reaction conditions high yields of the mono-acylated products are obtained, which contain minor amounts of bis(meth)acrylates. In addition it was observed that Novozyme 435 catalyzes regioselectively the acylation of the primary hydroxyl groups. In comparison with the chemical catalyzed route no selectivity was observed for unsubstituted diols. For substituted diols more mono-acylated product was formed in the lipase-catalyzed reaction than in the chemical catalyzed reaction.
Free radical and nitroxide mediated polymerization of hydroxy-functional acrylates prepared via lipase-catalyzed transacylation reactions
Popescu, Dragos,Hoogenboom, Richard,Keul, Helmut,Moeller, Martin
experimental part, p. 2610 - 2621 (2011/04/22)
3-Hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 2-methyl-3-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, neopentyl glycol acrylate, glyceryl acrylate, and dihydroxyhexyl acrylate were prepared via transacylation reaction of methyl acrylate with diols and triols catalyzed by Candida antarctica lipase B. After removal of the enzyme by filtration and the methyl acrylate by distillation, the monomers were polymerized via free radical polymerization (FRP) with azobisisobutyronitrile as initiator and nitroxide mediated polymerization (NMP) employing Blocbuilder alkoxyamine initiator and SG-1 free nitroxide resulting in hydroxy functional poly(acrylates). The NMP kinetics are discussed in detail. In addition, the polymers obtained by FRP and NMP are compared and the results are related to the amount of bisacrylates that are present in the initial monomer mixtures resulting from the transacylation reactions
Thermal reactions of substituted cyclopropenone acetals. Regio- and stereochemistry of vinylcarbene formation and low-temperature [3 + 2] cycloaddition
Tokuyama, Hidetoshi,Isaka, Masahiko,Nakamura, Eiichi
, p. 5523 - 5530 (2007/10/02)
Cyclopropenone acetals bearing olefinic substituents of diverse electronic character have been synthesized and examined for their thermal behavior toward water and electron-deficient olefins. The substituted cyclopropenes underwent regio- and stereoselect
