Synthesis of woody oil-based plasticizer via solvent-free Diels-Alder reaction and its biodegradability

Abstract

Woody oil is extracted from the fruits or seeds of woody plants . Preparing woody oil based and biodegradable plasticizer via solvent-free Diels-Alder reaction can reduce plasticizer enrichment and pollution, as well as dependence on petrochemical resources. Herein, woody oil based plasticizer (TOP-Ⅰ and TOP-Ⅱ) were successfully synthesized from renewable woody oil via solvent-free Diels-Alder reaction. Chemical structure of TOP-Ⅰ and TOP-Ⅱ was characterized with 1 H NMR, Biodegradation of TOP-Ⅱ was investigated in active soil and digestive system of Tenebrio molitor . Degradation products were extracted from active soil and Tenebrio molitor feces, the results showed that TOP-Ⅱ experienced biodegradation and formed degradation components with low molecular weight substances. The insect degradation of bio-based plasticizers was first reported and provided an effective way to reduce plasticizer enrichment and pollution. In addition, TOP-Ⅰ and TOP-Ⅱ was used to replace petroleum-based and non-degradable dioctyl phthalate (DOP) in plasticized poly(vinyl chloride) (PVC). The obtained plasticized PVC with TOP-Ⅰ and TOP-Ⅱ showed improved thermal stability, aging resistance, plasticization and solvent extraction resistance, the related mechanism behind these performances were also explored. • Biodegradable plasticizers could reduce plasticizer enrichment and pollution. • Woody oil based plasticizer was synthesized via solvent-free Diels-Alder reaction. • The bio-based plasticizer was degradable with active soil and Tenebrio molitor. • Plasticized PVC with woody oil based plasticizers had excellent properties. • The bio-based plasticizer might replace petro-based or non-degradable plasticizer.