POS1-1420
Castor Oil-Derived C7 and C18 Platform Monomers for Biomass Resource Carbon (BRC)-Based Polymer Synthesis
When and Where
Nov 30, -0001
12:00am - 12:00am
Presenter(s)
SUNIL KUMAR (KANGWON NATIONAL UNIVERSITY, GANGNEUNG)
Co-Author(s)
Abstract
Renewable monomers from non-edible biomass offer a sustainable alternative to petroleum-derived chemicals while expanding the molecular toolbox for polymer synthesis. Ricinoleic acid, the major fatty acid of castor oil, is an attractive platform molecule owing to its hydroxyl, alkene, and carboxylic acid functionalities. Herein, we report two complementary routes that convert castor oil into structurally distinct polymerizable monomers. Mesylation of methyl ricinoleate followed by lithium aluminum hydride reduction afforded oleyl alcohol (C18) as the major product; since oleyl alcohol is conventionally produced from the oleic acid of edible vegetable oils, this route establishes non-edible castor oil as an alternative renewable feedstock, and subsequent acrylation furnished long-chain renewable acrylates. More significantly, Ru-catalyzed oxidative cleavage of ricinoleic acid afforded heptanoic acid (C7) together with azelaic acid, and the same product distribution was obtained from castor oil and methyl ricinoleate. Unlike ozonolysis, which typically yields 3-hydroxynonanoic acid, this pathway proceeds with a two-carbon loss to give heptanoic acid, a product not previously reported from the oxidative cleavage of ricinoleic acid; preliminary mechanistic studies implicate the C12 hydroxyl group, positioned β to the nascent carboxyl, in this over-oxidation. Reduction to heptanol and acrylation then delivered the corresponding monomers. Both C7 and C18 platforms are currently being applied to Biomass Resource Carbon (BRC)-based polymers, providing a versatile route from non-edible biomass to structurally diverse polymer precursors and sustainable materials.
