Diols obtained by the ring-opening of biomass-based c-valerolactone (GVL) are potentially valuable building blocks that can be used as precursors in the manufacture of green polymers and resins. We report here a study on the ring-opening of GVL through adding amine compounds. The reactivity of the applied amine compounds in this ring-opening was tested by varying the structure of the amine compounds. Both monoamines (ammonium, 2-aminoethanol, 2-phenylethylamine, and morpholine) and di-amines (1,2-diaminoethane, 1,2-diaminopropane, and piperazine) were used. The study showed that steric hindrance at the reacting amine-function plays a more prominent role than local point charge.To optimize the yield of the desired di-functional monomers, the ring-opening of GVL with 1,2-diaminoethane (1,2-DE) was studied in more detail. Reaction temperature (25-100 C), reaction time, and molar ratio of the reactants appeared to be the determining processing parameters. These were found to be more important than the use of catalysts (triphenylphosphine, Tin(II)-2-ethylhexanoate, Ytterbium(III)trifuoromethanesulfonate, AlCl 3 , and SnCl 2 ) and solvent polarity (methanol, DMA, DMSO, and water
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.