Propiolated Castor Oil: A Novel and Highly Versatile Bio-Based Platform for Extremely Fast, Catalyst-, and Solvent-Free Amino-yne Click Reactions

Büşra Çelik, Dilhan Kandemir, Serter Luleburgaz, Emrah Çakmakçi, Ufuk Saim Gunay, Volkan Kumbaraci, Hakan Durmaz*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The quest for sustainable monomers and “green” synthetic pathways for the design, fabrication, and modification of various polymers is of great importance and attracts a great deal of attention. Here, a highly versatile and novel bio-based platform was developed by reacting castor oil with propiolic acid for performing amino-yne click reactions. Owing to the electron-deficient nature of the propiolic acid esters, amino-yne click reactions were conducted with ease at room temperature, in the absence of any catalyst and solvent (as long as the amines were low-viscosity liquids at room temperature), and within 5 min. Several primary and secondary amines were shown to react readily with the developed platform. Furthermore, thermosets were prepared by using the propiolated castor oil and multifunctional amines. The prepared thermosets displayed improved thermal properties and elastomer-like mechanical properties.

Original languageEnglish
Pages (from-to)831-841
Number of pages11
JournalACS Sustainable Chemistry and Engineering
Volume11
Issue number2
DOIs
Publication statusPublished - 16 Jan 2023

Bibliographical note

Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society.

Funding

This work was supported by the Research Fund of the Istanbul Technical University (project no: TGA-2022-43943).

FundersFunder number
Istanbul Teknik ÜniversitesiTGA-2022-43943

    Keywords

    • activated alkyne
    • amino-yne click reactions
    • aza-Michael
    • castor oil
    • green chemistry
    • propiolic acid

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