Synthesis of Levulinic Acids From Muconic Acids in Hot Water

Area of Science:

• Green Chemistry
• Biorenewable Chemicals
• Polymer Science

Background:

• Levulinic acid is a crucial biorenewable platform chemical.
• Current production methods from sugars suffer from low yields and separation challenges.
• Developing alternative, efficient synthesis routes is essential for sustainable chemical production.

Purpose of the Study:

• To develop a novel, selective hydrothermal method for producing levulinic acid and its derivatives.
• To explore the synthesis of substituted levulinic acids from substituted muconic acids.
• To evaluate the performance of a novel diester plasticizer derived from a substituted levulinic acid.

Main Methods:

• Hydrothermal synthesis of levulinic acid from muconic acid at 180°C.
• Synthesis of substituted muconic acids via catechol oxidation.
• Esterification of 3-propyllevulinic acid with 1,4-butanediol to form a diester.
• Plasticizer performance testing in polyvinyl chloride (PVC) and polylactic acid (PLA).

Main Results:

• A selective hydrothermal route to levulinic acid from muconic acid was established.
• Hitherto unknown substituted levulinic acids were synthesized, including 3-propyllevulinic acid.
• The derived butane-1,4-diyl bis(4-oxo-3-propylpentanoate) plasticizer demonstrated superior performance in PVC and PLA compared to non-substituted analogs.
• The new plasticizer matched the performance of di-2-ethylhexyl phthalate (DEHP) in PVC.

Conclusions:

• Hydrothermal processing offers a viable and selective alternative for levulinic acid production.
• Substituted levulinic acid derivatives can be effectively synthesized and utilized.
• Novel diester plasticizers derived from these compounds exhibit excellent performance, rivaling commercial benchmarks.