Indigo Beyond Tradition: Scalable Derivatization, Extraction from Waste Denim Textiles, and Boc-Protected Intermediates
Gökhan Kaplan, Nurgül Seferoğlu, Ertan Şahin, Zeynel Seferoğlu
TL;DR
This paper introduces a scalable method to synthesize Boc-protected indigo derivatives and repurpose waste denim textiles, offering a sustainable solution for the textile industry.
Contribution
The first scalable, column-free synthesis of Boc-protected indigo derivatives and their use in recycling waste denim textiles.
Findings
N-mono-Boc indigo was synthesized under mild conditions with moderate yield.
The oxidation mechanism of di-Boc indigo was elucidated using experimental and theoretical methods.
Indigo-dyed textile waste can be repurposed as a starting material for Boc-protected indigo derivatives.
Abstract
This study demonstrates the feasibility of industrial-scale, column-free synthesis of tert-butoxycarbonyl (Boc)-protected indigo derivatives and highlights their application potential in the textile industry for the dyeing of previously undyeable synthetic textiles with indigo. The direct synthesis of N-mono-tert-butoxycarbonyl (Boc) indigo, an important intermediate for indigo substitution studies, was achieved under very mild conditions and in a moderate yield. For the first time, the molecular structures of all synthesized compounds were comprehensively characterized through detailed NMR and HRMS analyses as well as the single-crystal X-ray diffraction method. The influence of the Boc groups on the photophysical and thermal properties, oxidation–reduction behavior, and dyeing performance was thoroughly investigated and defined. Importantly, the oxidation mechanism of dihydro-di-Boc…
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Taxonomy
TopicsDyeing and Modifying Textile Fibers · Lignin and Wood Chemistry · Synthesis of Organic Compounds