Facile Synthesis of Optically-Active γ-Valerolactone from Levulinic Acid and Its Esters Using a Heterogeneous Enantio-Selective Catalyst

• Published in: Catalysis letters Vol. 148; no. 3; pp. 824 - 830
• Main Authors: Osawa, Tsutomu, Tanabe, Yuya
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.03.2018; Springer Nature B.V
• Subjects: Acids; Catalysis; Catalysts; Cellulose esters; Chemical synthesis; Chemistry; Chemistry and Materials Science; Dehydration; Esters; Industrial Chemistry/Chemical Engineering; Levulinic acid; Nickel; Organometallic Chemistry; Physical Chemistry; Tartaric acid; Enantio-differentiating hydrogenation; Tartaric acid modified Ni; Levulinic acid; Optically-active γ-valerolactone; Alkyl levulinate
• ISSN: 1011-372X; 1572-879X
• DOI: 10.1007/s10562-017-2291-2

Optically-active γ-valerolactone was synthesized by the enantio-selective hydrogenations of levulinic acid and its esters. A tartaric acid-NaBr-modified nickel catalyst produced the optically-active γ-valerolactone with a 60% enantiomeric excess (ee), almost quantitative conversion and chemoselectivity. The synthesis of the optically-active γ-valerolactone using the enantio-selective heterogeneous catalyst would be promising for the large-scale industrial production from levulinic acid and its esters, which can be obtained by the acid-catalyzed dehydration of cellulosic fraction of biomass. Graphical Abstract