ArticleGreen chemistry : an international journal and green chemistry resource : GC2023
High yield production of 1,4-cyclohexanediol and 1,4-cyclohexanediamine from high molecular-weight lignin oil.
Article in Green chemistry : an international journal and green chemistry resource : GC, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Synthesis of bio-based N-containing compounds from biomass.National science review · 2025Review
- Tunable Transfer-Hydrodeoxygenated Upgrading of Lignin-Derived Propylphenols to Versatile Value-Added Alkane-Based Chemicals.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Benzenoid Aromatics from Renewable Resources.Chemical reviews · 2024Review
- The synthesis of fructose-based surfactants.Green chemistry : an international journal and green chemistry resource : GC · 2024Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The complete utilization of all lignin depolymerization streams obtained from the reductive catalytic fractionation (RCF) of woody biomass into high-value-added compounds is a timely and challenging objective. Here, we present a catalytic methodology to transform beech lignin-derived dimers and oligomers (DO) into well-defined 1,4-cyclohexanediol and 1,4-cyclohexanediamine. The latter two compounds have vast industrial relevance as monomers for polymer synthesis as well as pharmaceutical building blocks. The proposed two-step catalytic sequence involves the use of the commercially available RANEY® Ni catalyst. Therefore, the first step involves the efficient defunctionalization of lignin-derived 2,6-dimethoxybenzoquinone (DMBQ) into 1,4-cyclohexanediol (14CHDO) in 86.5% molar yield, representing a 10.7 wt% yield calculated on a DO weight basis. The second step concerns the highly selective amination of 1,4-cyclohexanediol with ammonia to give 1,4-cyclohexanediamine (14CHDA) in near quantitative yield. The ability to use RANEY® Ni and ammonia in this process holds great potential for future industrial synthesis of 1,4-cyclohexanediamine from renewable resources.
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Registered trials
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