Related Experiment Video
Updated: Jul 4, 2026

Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
Published on: November 30, 2020
Synthesis of readily recyclable biobased plastics by Diels-Alder reaction
1Institute of Industrial Science, the University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan.
Abstract:
Readily recyclable biobased plastics were designed and synthesized utilizing the thermally reversible DA reaction. Furyl-telechelic poly(butylene succinate) prepolymers (PBSF(2)) were extended with bis- and tris-maleimide linkers (M(2) and M(3)) by the DA reaction in the bulk state to produce linear and network polymers, respectively. The DA reaction was able to proceed at 25-80 degrees C, at which crystalline domains of PBSF(2) were present. In the linear polymer system, the molecular weight in the reaction equilibrium was dependent on the chain length of the prepolymer, but almost independent of the reaction temperature. The cycle of DA and retro-DA reactions was repeatable with no prepolymer deterioration.
Related Concept Videos
Bioplastics
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Microbial Bioremediation of Plastics
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...

