High yield production of 1,4-cyclohexanediol and 1,4-cyclohexanediamine from high molecular-weight lignin oil.

Autor:	Wu X; Stratingh Institute for Chemistry, University of Groningen Groningen The Netherlands., De Bruyn M; Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz Heinrichstrasse 28/II 8010 Graz Austria katalin.barta@uni-graz.at., Hulan JM; Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz Heinrichstrasse 28/II 8010 Graz Austria katalin.barta@uni-graz.at., Brasil H; Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz Heinrichstrasse 28/II 8010 Graz Austria katalin.barta@uni-graz.at., Sun Z; Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing Forestry University No. 35 Tsinghua East Road Haidian District Beijing 100083 P. R. China., Barta K; Stratingh Institute for Chemistry, University of Groningen Groningen The Netherlands.; Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz Heinrichstrasse 28/II 8010 Graz Austria katalin.barta@uni-graz.at.
Jazyk:	angličtina
Zdroj:	Green chemistry : an international journal and green chemistry resource : GC [Green Chem] 2022 Nov 29; Vol. 25 (1), pp. 211-220. Date of Electronic Publication: 2022 Nov 29 (Print Publication: 2023).
DOI:	10.1039/d2gc03777g
Abstrakt:	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. Competing Interests: The authors declare no competing interests. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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