POS1-1356
Substituted Group Effects in Liquid Jones Oxidation of Primary Alcohols: Foundation for Eco-Friendly Conversion of Seaweed-Derived 3-HP to Malonic Acid
Topic
S1. Polymer Synthesis
When and Where
Sep 30, 2026
08:30 - 09:30
Room 301 (Grand Ballroom)
Session Chairs
Heesuk KIM
Jinhye BAE
Presenter(s)
Yunseul Park (Department of Chemistry, Kongju National University)
Co-Author(s)
Abstract
To address marine debris issues such as Sargassum horneri accumulation in Jeju, converting biomass-derived 3-hydroxypropionic acid (3-HP) into high-value malonic acid (MA) presents a sustainable upcycling pathway. This study systematically investigates the liquid Jones oxidation of substituted primary alcohols as a model system to optimize 3-HP conversion, focusing on how functional groups affect yields. Since E2 elimination of α-hydrogen from the chromate ester is the rate-determining step, halogenated substrates (Cl, Br, I) achieved high yields (81.0–88.5%) due to the strong electron-withdrawing inductive effect increasing α-hydrogen acidity. Conversely, the F-substituted substrate gave a low yield (36.9%) due to poor work-up extraction from strong hydration. Amine and thiol groups proved unsuitable due to ammonium salt formation and direct Cr(VI) reduction, while 4-hydroxy-2-butanone and 1,3-butanediol underwent subsequent molecular degradation, failing to yield single desired acids.
To overcome the environmental toxicity of residual chromium and corrosive acids in liquid systems, future work will focus on developing silica-supported heterogeneous catalysts (Silica Jones Reagent) to minimize heavy metal residues. Ultimately, this process will be integrated into a flow chemistry system to establish a safe, scalable, and eco-friendly platform for mass-producing seaweed-derived malonic acid.
To overcome the environmental toxicity of residual chromium and corrosive acids in liquid systems, future work will focus on developing silica-supported heterogeneous catalysts (Silica Jones Reagent) to minimize heavy metal residues. Ultimately, this process will be integrated into a flow chemistry system to establish a safe, scalable, and eco-friendly platform for mass-producing seaweed-derived malonic acid.
