5581-31-7Relevant academic research and scientific papers
Kinetics of the Aqueous Phase Reactions of Atmospherically Relevant Monoterpene Epoxides
Cortés, DIego A.,Elrod, Matthew J.
, p. 9297 - 9305 (2017/12/18)
Laboratory and field measurements have demonstrated that an isoprene-derived epoxide intermediate (IEPOX) is the origin of a wide range of chemical species found in ambient secondary organic aerosol (SOA). In order to explore the potential relevance of a similar mechanism for the formation of monoterpene-derived SOA, nuclear magnetic resonance techniques were used to study kinetics and reaction products of the aqueous-phase reactions of several monoterpene epoxides: β-pinene oxide, limonene oxide, and limonene dioxide. The present results, combined with a previous study of α-pinene oxide, indicate that all of these epoxides will react more quickly than IEPOX with aqueous atmospheric particles, even under low-acidity conditions. As for α-pinene oxide, the observed products can be mainly rationalized with a hydrolysis mechanism, and no long-lived organosulfate or nitrate species nor species that retain the β-pinene bicyclic carbon backbone are observed. As bicyclic ring-retaining organosulfate and nitrate species have been previously observed in monoterpene-derived SOA, it appears that monoterpene-derived epoxides may not be as versatile as IEPOX in producing a range of SOA species, and other mechanisms are needed to rationalize organosulfate and nitrate formation.
Green Organocatalytic Dihydroxylation of Alkenes
Theodorou, Alexis,Triandafillidi, Ierasia,Kokotos, Christoforos G.
, p. 1502 - 1509 (2017/04/01)
An inexpensive, green, metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 and 2,2,2-trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product.
High Purity Limonene Dicarbonate as Versatile Building Block for Sustainable Non-Isocyanate Polyhydroxyurethane Thermosets and Thermoplastics
Schimpf, Vitalij,Ritter, Benjamin S.,Weis, Philippe,Parison, Karsten,Mülhaupt, Rolf
, p. 944 - 955 (2017/02/23)
Oxidation and subsequent catalytic carbonation of limonene, gained from orange peels, afford high purity limonene dicarbonate (LC) as a versatile building block for tailoring linear and cross-linked non-isocyanate polyurethanes (NIPU) from renewable resources. Spectroscopic investigations reveal so far unknown highly colored carbonation byproducts which are successfully removed to yield crystalline LC. Melt-phase polyaddition of a dimer fatty acid based diamine and its diamine-terminated LC-prepolymers with carbonated 1,4-butanediol diglycidyl ether (BDGC) produces 100% bio-based linear NIPU thermoplastics. Side-reactions occurring during polymerization account for decreasing molar mass with increasing LC content. Curing carbonated pentaerythritol glycidyl ether (PGC)/LC blends with 1,5-diaminopentane, gained from lysine, enables tailoring of 100% bio-based NIPU thermosets exhibiting unconventional property profiles. The incorporation of small amounts high purity LC substantially improves NIPU glass temperature, stiffness, and strength without sacrificing elongation at break. High purity LC prevents color formation of LC-based NIPU coatings.
