Issue 2, 2024

Iron-free mechanochemical limonene inverse vulcanization

Abstract

An iron-free mechanochemical-assisted limonene inverse vulcanization is reported. The process makes use of only limonene and sulphur, industrial waste by-products, under mild conditions (ca. 40 °C) and short time (2 h) using a zirconium oxide reactor and a planetary ball mil. The obtained high value products are light yellow solids, readily soluble in chloroform, optically active oligosulfides, which are different from polysulfides reported under conventional conditions (ca. 185 °C), as confirmed by NMR spectroscopy and mass spectrometry. A general reaction mechanism is proposed, initiated by homolytic sulphur ring opening triggered by mechanical stress, and involving thiirane intermediates, via an addition–elimination reaction of sulphur to the limonene double bonds.

Graphical abstract: Iron-free mechanochemical limonene inverse vulcanization

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Article information

Article type
Paper
Submitted
11 Oct 2023
Accepted
25 Dec 2023
First published
29 Jan 2024
This article is Open Access
Creative Commons BY license

RSC Mechanochem., 2024,1, 176-180

Iron-free mechanochemical limonene inverse vulcanization

R. Tedjini, R. Viveiros, T. Casimiro and V. D. B. Bonifácio, RSC Mechanochem., 2024, 1, 176 DOI: 10.1039/D3MR00002H

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