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用木糖或半纤维素选择性生产甲基茚和四氢化萘。

Selective production of methylindan and tetralin with xylose or hemicellulose.

作者信息

Zou Zhufan, Yu Zhenjie, Guan Weixiang, Liu Yanfang, Yao Yumin, Han Yang, Li Guangyi, Wang Aiqin, Cong Yu, Liang Xinmiao, Zhang Tao, Li Ning

机构信息

CAS Key Laboratory of Science and Technology on Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.

School of Chemistry, Dalian University of Technology, Dalian, China.

出版信息

Nat Commun. 2024 May 2;15(1):3723. doi: 10.1038/s41467-024-48101-x.

DOI:10.1038/s41467-024-48101-x
PMID:38697973
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11066016/
Abstract

Indan and tetralin are widely used as fuel additives and the intermediates in the manufacture of thermal-stable jet fuel, many chemicals, medicines, and shockproof agents for rubber industry. Herein, we disclose a two-step route to selectively produce 5-methyl-2,3-dihydro-1H-indene (abbreviated as methylindan) and tetralin with xylose or the hemicelluloses from agricultural or forestry waste. Firstly, cyclopentanone (CPO) was selectively formed with ~60% carbon yield by the direct hydrogenolysis of xylose or hemicelluloses on a non-noble bimetallic Cu-La/SBA-15 catalyst. Subsequently, methylindan and tetralin were selectively produced with CPO via a cascade self-aldol condensation/rearrangement/aromatization reaction catalyzed by a commercial H-ZSM-5 zeolite. When we used cyclohexanone (another lignocellulosic cycloketone) in the second step, the main product switched to dimethyltetralin. This work gives insights into the selective production of bicyclic aromatics with lignocellulose.

摘要

茚满和四氢萘被广泛用作燃料添加剂以及制造热稳定喷气燃料、许多化学品、药品和橡胶工业防震剂的中间体。在此，我们公开了一种两步法路线，可从农业或林业废弃物中的木糖或半纤维素选择性生产5-甲基-2,3-二氢-1H-茚（简称为甲基茚满）和四氢萘。首先，通过木糖或半纤维素在非贵金属双金属Cu-La/SBA-15催化剂上的直接氢解反应，以约60%的碳产率选择性地生成环戊酮（CPO）。随后，通过商业H-ZSM-5沸石催化的级联自羟醛缩合/重排/芳构化反应，用CPO选择性生产甲基茚满和四氢萘。当我们在第二步中使用环己酮（另一种木质纤维素环酮）时，主要产物转变为二甲基四氢萘。这项工作为利用木质纤维素选择性生产双环芳烃提供了见解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/22a0247a59e2/41467_2024_48101_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/990590c9816d/41467_2024_48101_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/bbad394da539/41467_2024_48101_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/c1c705779305/41467_2024_48101_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/9f033c2cbfe2/41467_2024_48101_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/93dae9c55441/41467_2024_48101_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/b24d021b2458/41467_2024_48101_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/fa1608a66282/41467_2024_48101_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/0006acf50ffc/41467_2024_48101_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/22a0247a59e2/41467_2024_48101_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/990590c9816d/41467_2024_48101_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/bbad394da539/41467_2024_48101_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/c1c705779305/41467_2024_48101_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/9f033c2cbfe2/41467_2024_48101_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/93dae9c55441/41467_2024_48101_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/b24d021b2458/41467_2024_48101_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/fa1608a66282/41467_2024_48101_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/0006acf50ffc/41467_2024_48101_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1904/11066016/22a0247a59e2/41467_2024_48101_Fig9_HTML.jpg

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本文引用的文献

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Angew Chem Int Ed Engl. 2023 Mar 20;62(13):e202300008. doi: 10.1002/anie.202300008. Epub 2023 Feb 14.
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Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass.从生物质出发高效合成己二酸的催化剂。
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Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d-Proline from Furfural.
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Selective production of indane and its derivatives from lignin over a modified niobium-based catalyst.在改性铌基催化剂上从木质素中选择性生产茚满及其衍生物。
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