木质素精炼制芳香含氮杂环化合物: 高值化学品可持续生产新机遇

doi:10.1016/S1872-2067(25)64798-X

催化学报 ›› 2025, Vol. 78: 25-46.DOI: 10.1016/S1872-2067(25)64798-X

木质素精炼制芳香含氮杂环化合物: 高值化学品可持续生产新机遇

苏文韬^a^,^b, 田胜龙^a, 杨华美^a^,^c, 李昌志^a^,^b^,^*(), 张涛^a^,^b

^a中国科学院大连化学物理研究所, 中国科学院应用催化科学技术重点实验室, 辽宁大连 116023
^b中国科学院大学, 北京 100049
^c徐州工业大学材料化工学院, 江苏徐州 221018

收稿日期:2025-05-10 接受日期:2025-06-18 出版日期:2025-11-18 发布日期:2025-10-14
通讯作者: *电子信箱: licz@dicp.ac.cn (李昌志).
基金资助:
国家重点研发计划(2023YFA1507902);国家自然科学基金单原子催化研究中心(22388102);中国科学院战略性先导科技专项(XDB17020100);大连市科学技术局(2021RT04)

Refining lignin into aromatic nitrogen-heterocyclic compounds: Sustainable avenue toward value-added chemicals

Wentao Su^a^,^b, Shenglong Tian^a, Huamei Yang^a^,^c, Changzhi Li^a^,^b^,^*(), Tao Zhang^a^,^b

^aCAS Key Laboratory of Science and Technology on Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^bUniversity of Chinese Academy of Sciences, Beijing 100049, China
^cSchool of Materials and Chemical Engineering, Xuzhou University of Technology, Xuzhou 221018, Jiangsu, China

Received:2025-05-10 Accepted:2025-06-18 Online:2025-11-18 Published:2025-10-14
Contact: *E-mail: licz@dicp.ac.cn (C. Li).
About author:Changzhi Li (Dalian Institute of Chemical Physics, Chinese Academy of Science) was invited as a young member of the 5th and 6th Editorial Board of Chin. J. Catal. Prof. Changzhi Li received his B.A. degree from Hunan Normal University (P. R. China) in 2002, and Ph.D. degree from Dalian Institute of Chemical Physics, Chinese Academy of Sciences in 2009. Then he has been working in CAS Key Laboratory of Science and Technology on Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, where he was promoted to a full professor in 2019. The overarching theme of his research program is biomass catalytic conversion, especially the catalytic valorisation of lignin into value-added chemicals and high-density fuels. He has published over 90 peer-reviewed papers on international journals, and has been authorized more than 50 patents in China.
Supported by:
National Key R&D Program of China(2023YFA1507902);NSFC Center for Single-Atom Catalysis(22388102);Strategic Priority Research Program of the Chinese Academy of Sciences(XDB17020100);Science and Technology Bureau of Dalian City(2021RT04)

摘要/Abstract

摘要：

木质素作为自然界中储量最丰富的可再生芳香化合物资源, 是由苯丙烷单元(如紫丁香基、愈创木基和对羟基苯基)通过C-O和C-C键(如β-O-4和4-O-5等)交联而成的三维无定形聚合物. 然而, 因其结构复杂性和化学惰性, 目前大部分木质素只能被低值化利用. 芳香含氮杂环化合物是医药、农药和功能材料的重要骨架, 当前其合成高度依赖于不可再生的化石原料, 且反应路线为多步反应过程, 存在原子经济性低、环境污染等问题. 木质素因其固有的芳香骨架和丰富的含氧官能团(如羟基、羰基), 为绿色合成芳香含氮杂环化合物提供了新机遇. 开发基于木质素的可持续合成路线, 不仅可降低碳足迹、拓展生物基化学品多样性, 而且对提升生物炼制经济性和推动医药化工产业的绿色升级具有重要意义.

本文综述了木质素制备芳香含氮杂环化合物的研究进展. 系统介绍了从木质素、木质素衍生单体或模型化合物出发, 经过一步或多步反应构建五元、六元、七元芳香含氮杂环化合物的最新成果. 针对木质素的结构特点, 深入讨论了木质素侧链烷基以及芳环骨架在构建杂环化合物中潜在反应位点与反应类型. 针对催化过程中C-O、C-C键断裂与C-N键形成的兼容性问题及含氮杂环构建所面临的挑战, 结合催化机理和反应路径分析, 全面总结了该系列转化中路线设计思路和催化体系的构建策略. 由于木质素分子结构的复杂性, 其转化过程普遍面临选择性偏低的难题, 因此, 当前成果多局限于木质素解聚单体和模型化合物转化. 为了推进该技术的工业化应用, 尚需革新生物质预处理技术, 最大限度地保留木质素中β-O-4键等关键活性连接键; 设计高效反应路线和多功能催化剂, 突破木质素原料定向转化的瓶颈; 建立绿色分离纯化系统, 解决复杂产物体系中目标组分的高效分离与纯化问题; 拓展下游产品高值化应用出口, 构建"预处理-催化-分离-应用"全链条创新体系, 形成从基础研究到产业应用的完整技术链条. 上述突破将显著提升木质素资源化利用的经济性和可持续性.

综上, 本文系统地总结了木质素转化为高附加值芳香含氮杂环化合物的新进展, 归纳讨论了反应路线、反应位点、催化机理和产物类别, 展望了未来研究方向及所面临的关键科学问题和技术瓶颈. 本文不仅为木质素转化合成芳香含氮杂环的相关研究提供了有益的参考, 更为解决生物质高值化利用过程中所面临的共性问题提供了启发和借鉴.

关键词: 木质素, 生物炼制, 含氮杂环化合物, 绿色化学, C-O键断裂, C-N键构建

Abstract:

Lignin is the only largest renewable aromatic resource in nature. Currently, most lignin is underutilized for low-value applications due to the complex structure and recalcitrant chemical properties. Over the past decades, extensive research has been devoted to valorizing lignin into aromatic N-heterocycles in the presence of nitrogen sources. It overcomes the element limitation, expands the products portfolio and would play a momentous role in value-added biorefinery concept. In this review, the latest research progress in the synthesis of N-heterocyclic compounds from lignin, lignin model compounds, and lignin-derived monomers (phenols, aromatic alcohols, aldehydes, ketones, and ethers) is presented. According to the structural characteristics of the products, these achievements are classified by the construction of five-, six-, and seven-membered N-heterocyclic compounds through one-step, multi-step, or one-pot multi-step reactions. Furthermore, the tailor-designed routes and catalytic systems, along with the reaction mechanisms/pathways involved are entirely discussed to elucidate the challenges regarding the structural complexity of lignin, the incompatible catalysis for C-O cleavage and C-N formation, as well as the nitrogen-heterocyclic ring construction. The prospects, future research efforts and process developments for the refining of lignin into aromatic N-heterocyclic compounds are outlined in terms of economy, environmental friendliness, and safety so as to draw some guidelines for lignin valorization.

Key words: Lignin, Biorefinery, N-heterocyclic compound, Green chemistry, C-O cleavage, C-N formation

苏文韬, 田胜龙, 杨华美, 李昌志, 张涛. 木质素精炼制芳香含氮杂环化合物: 高值化学品可持续生产新机遇[J]. 催化学报, 2025, 78: 25-46.

Wentao Su, Shenglong Tian, Huamei Yang, Changzhi Li, Tao Zhang. Refining lignin into aromatic nitrogen-heterocyclic compounds: Sustainable avenue toward value-added chemicals[J]. Chinese Journal of Catalysis, 2025, 78: 25-46.

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图/表 23

Fig. 1. Summary of aromatic N-heterocyclic compounds from lignin.

Fig. 2. (a) Palladium-catalyzed formal cross-coupling between monophenols and pyrrolidines/indolines to give several N-cyclohexyl-substituted pyrrole or indole products. Reprinted with permission from Ref. [55]. Copyright 2017, Royal Society of Chemistry. (b) The reaction mechanism. Reprinted with permission from Ref. [55]. Copyright 2018, Wiley-VCH.

Fig. 4. By fusing the benzene ring at specific positions on the imidazole ring, constructing Benzimidazole and imidazopyridine frameworks.

Fig. 7. DDQ-catalyzed construction of imidazole derivatives from the lignin β-O-4 model compound and o-phenylenediamine, and the possible reaction mechanism. Reprinted with permission from Ref. [75]. Copyright 2022, Wiley-VCH.

Fig. 8. Formation of isoxazole and nitrile derivatives through hydroxylamine participation in lignin depolymerization. Reprinted with permission from Ref. [79]. Copyright 2018, American Chemical Society.

Fig. 11. Construction of quinoline and acridine from the β-O-4 major decomposition derivative.

Fig. 14. [Ir]- and [Cr]-complex-catalyzed synthesis of 3-oxo quinoline derivatives from the β-O-4 model compound. Reprinted with permission from Ref. [107]. Copyright 2023, American Chemical Society. Reprinted with permission from Ref. [108]. Copyright 2024, Royal Society of Chemistry.

Fig. 16. Coordination-mediated Co-Cu dual single-atom catalysts for the cascade transformation of the β-O-4 model compound to quinoline. Reprinted with permission from Ref. [110]. Copyright 2024, Wiley-Blackwell.

Fig. 19. One-pot synthesis of phenazine from lignin depolymerization-derived catechol and ammonia solution, and the main reaction processes. Reprinted with permission from Ref. [127]. Copyright 2022, Royal Society of Chemistry.

Fig. 22. Direct construction of N-aryl substituted pyrrolidine via Pd/C-catalyzed coupling of aryl ethers and pyrrolidines without additives. Reprinted with permission from Ref. [134]. Copyright 2021, Royal Society of Chemistry.

Fig. 23. Transformation of lignin via a three-step approach for the synthesis of heptacyclic N-heterocyclic compounds. Reprinted with permission from Ref. [138]. Copyright 2019, American Chemical Society.

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木质素精炼制芳香含氮杂环化合物: 高值化学品可持续生产新机遇

Refining lignin into aromatic nitrogen-heterocyclic compounds: Sustainable avenue toward value-added chemicals

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