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Pinene-based oxidative synthetic toolbox for scalable polyester synthesis
KTH Royal Institute of Technology, Sweden.
KTH Royal Institute of Technology, Sweden.
KTH Royal Institute of Technology, Sweden.
KTH Royal Institute of Technology, Sweden.
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2021 (English)In: JACS Au, E-ISSN 2691-3704, Vol. 1, no 11, p. 1949-1960Article in journal (Refereed) Published
Abstract [en]

Generation of renewable polymers is a long-standing goal toward reaching a more sustainable society . Herein we show how conceptually simple oxidative transformations can be used to unlock the inherent reactivity of terpene synthons in generating polyesters by two different mechanisms starting from the same α-pinene substrate. In the first pathway, α-pinene was oxidized into the bicyclic verbanone based lactone (VaL) and subsequently polymerized into star-shaped polymers via ring-opening polymerization, resulting in a biobased semicrystalline polyester with tunable glass transition and melting temperatures In a second pathway, polyesters were synthesized via polycondensation, utilizing the diol (1-(1'-hydroxyethyl)-3-(2'-hydroxyethyl)-2,2-dimethylcyclobutane (HHDC)) synthesized by oxidative cleavage of the double bond of α-pinene, together with unsaturated biobased diesters such as di-Me maleate (DMM) and di-Me itaconate (DMI), resp. The resulting families of terpene-based polyesters were thereafter successfully crosslinked by either transetherification, utilizing the terminal hydroxyl groups of the synthesized verbanone-based materials, or by UV-irradiation, utilizing the unsaturation provided by the DMM or DMI moieties within the HHDC-based copolymers. This work highlights the potential to apply an oxidative toolbox to valorize inert terpene metabolites enabling generation of bio sourced polyesters and coatings thereof by complementary mechanisms.

Place, publisher, year, edition, pages
American Chemical Society , 2021. Vol. 1, no 11, p. 1949-1960
Keywords [en]
scalable polyester synthesis oxidative transformation
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:ri:diva-57567DOI: 10.1021/jacsau.1c00312OAI: oai:DiVA.org:ri-57567DiVA, id: diva2:1625485
Available from: 2022-01-07 Created: 2022-01-07 Last updated: 2023-04-05Bibliographically approved

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Bhattacharyya, Shubhankar

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