多金属氧酸盐/乙酸协同氧化强化木质素高效解聚

doi:10.1016/S1872-2067(25)64737-1

催化学报 ›› 2025, Vol. 74: 352-364.DOI: 10.1016/S1872-2067(25)64737-1

多金属氧酸盐/乙酸协同氧化强化木质素高效解聚

曹家铭^a^,^b, 刘玉庭^b, 刘慧芳^b^,^*(), 刘春光^d^,^*(), 时君友^a^,^c^,^*(), 李宁^b^,^*()

^a东北林业大学材料科学与工程学院, 黑龙江哈尔滨 150040
^b中国科学院大连化学物理研究所, 催化基础国家重点实验室, 辽宁大连 116023
^c山东理工大学农业工程与食品科学学院, 山东淄博 255000
^d北华大学理学院, 吉林吉林 132013

收稿日期:2024-12-15 接受日期:2025-04-26 出版日期:2025-07-18 发布日期:2025-07-20
通讯作者: *电子信箱: liuhuifang@dicp.ac.cn (刘慧芳),liucg407@163.com (刘春光),bhsjy64@163.com (时君友),ningli603@dicp.ac.cn (李宁).
基金资助:
国家自然科学基金(32130073);国家自然科学基金(22478380);国家自然科学基金(22272169);辽宁省科学技术厅基金(2024JH2/102400040);催化国家重点实验室基金(2024SKL-B-007);辽宁省自然科学基金(2024-MSBA-56)

Oxidative depolymerization of lignin enhanced by synergy of polyoxometalate and acetic acid

Jiaming Cao^a^,^b, Yuting Liu^b, Huifang Liu^b^,^*(), Chunguang Liu^d^,^*(), Junyou Shi^a^,^c^,^*(), Ning Li^b^,^*()

^aMaterial Science and Engineering College of Northeast Forestry University, Harbin 150040, Heilongjiang, China
^bState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^cCollege of Agricultural Engineering and Food Science, Shandong University of Technology, Zibo 255000, Shandong, China
^dDepartment of Chemistry, Faculty of Science, Beihua University, Jilin 132013, Jilin, China

Received:2024-12-15 Accepted:2025-04-26 Online:2025-07-18 Published:2025-07-20
Contact: *E-mail: liuhuifang@dicp.ac.cn (H. Liu), liucg407@163.com (C. Liu), bhsjy64@163.com (J. Shi), ningli603@dicp.ac.cn (N. Li).
Supported by:
National Natural Science Foundation of China(32130073);National Natural Science Foundation of China(22478380);National Natural Science Foundation of China(22272169);Department of Science & Technology of Liaoning province(2024JH2/102400040);State Key Laboratory of Catalysis(2024SKL-B-007);Natural Science Foundation of Liaoning Province(2024-MSBA-56)

摘要/Abstract

摘要：

木质素作为一种可再生的三维高分子聚合物, 具有复杂的结构特征, 富含多种活性官能团和独特的芳环体系. 这种生物质资源作为生产高附加值平台化学品和燃料的可持续原料, 在替代传统化石资源方面展现出巨大潜力. 然而, 木质素固有的组分异质性、溶解性差等特性严重限制了其高值化利用. 其中, 将木质素选择性解聚为小分子芳香化合物是实现其高值化利用的关键途径之一. 在现有的多种催化解聚策略中, 氧化解聚技术因其反应条件温和且能高效制备含羰基的高附加值芳香化合物而受到广泛关注. 多金属氧酸盐作为一类优异的双功能催化剂, 同时具备酸性位点和氧化活性中心, 并能通过分子氧实现催化剂的再生循环. 但传统的氧化反应通常需要较高的氧气压力(1.0-2.5 MPa), 导致反应条件较为苛刻. 因此, 开发兼具高木质素溶解能力、低成本及低氧压需求的新型催化体系, 并深入探究其与木质素大分子的相互作用机制, 成为当前研究的重点方向.

针对上述问题, 本研究开发了一种基于磷钼酸(H₃PMo₁₂O₄₀)与乙酸协同催化的木质素低氧压解聚新策略. 采用可规模化制备的H₃PMo₁₂O₄₀作为多功能催化剂, 通过乙酸/水混合溶剂构建高效的催化环境, 在常压氧气的温和反应条件下实现了含羰基芳香族化合物产率超过20 wt%. 通过解聚产物中β-O-4等特征连接键信号的消失, 以及分子量的大幅度降低, 证实了催化体系优异的解聚效率。H₃PMo₁₂O₄₀在反应中同时发挥酸催化与氧化催化双重作用, 乙酸则显著提高木质素的溶解性, 并与催化剂形成稳定配合物结构, 结合理论计算与紫外光谱分析, 证实该配合物是通过乙酰基与Keggin型杂多酸结构表面的氧原子脱水缩合形成, 这种独特的配位作用显著增强了体系的氧化能力, 电化学测试中半波电位绝对值的降低为此提供了直接证据. 同时配合物的特征峰与纯H₃PMo₁₂O₄₀高度一致, 表明催化剂在反应过程中仍能够保持完整的Keggin结构. 进一步的机理研究揭示了超氧自由基的存在, 证实催化剂与溶剂间的协同效应能够活化分子氧并稳定活性氧物种. 此外, 结合乙酰化中间体的检测结果及吉布斯自由能计算, 明确了乙酰化路径在反应中的主导地位, 该路径不仅降低了反应能垒, 更重要的是通过α-OH位点的保护作用有效阻断了木质素缩合的副反应途径, 抑制了顽固C-C键的形成. 最后通过考察不同浓度、树种以及来源的木质素原料验证了该催化体系具有优异的普适性.

综上, 本文通过构建磷钼酸与乙酸的协同催化体系, 显著提升了反应体系的氧化性能, 在温和的低氧压条件下(0.1 MPa O₂)实现了木质素的高效解聚制备单酚化合物, 并结合机理研究阐明了反应机制, 为木质素资源的可持续转化与高值化利用提供新的技术路径和理论依据.

关键词: 催化氧化, 木质素高值化, 芳香族化学品, 磷钼酸, 有机酸

Abstract:

Oxidative catalysis enables lignin depolymerization to yield carbonyl-containing aromatic chemicals for sustainable lignocellulose valorization. The oxidative depolymerization of lignin requires high oxygen pressure and harsh conditions to trade off lignin’s structural complexity and limited solubility. Herein, we developed an oxidation system for lignin depolymerization using a single phosphomolybdic acid (H₃PMo₁₂O₄₀) catalyst in acetic acid solvent to address the aforementioned issues. The entire catalytic system was operated under only 0.1 MPa O₂ pressure, providing over 20 wt% of aromatic compounds containing aldehydes and carboxylic acids. Theoretical calculations combined with experimental analyses reveal structural transformations and redox behavior driven by the synergistic interaction between H₃PMo₁₂O₄₀ and acetic acid. Mechanistic studies detected superoxide radicals, confirming the joint role of catalyst and solvent in oxygen activation, radicals stabilization, and enhanced reaction efficiency. A low-cost, commercially available catalyst with minimal oxygen demand offers a promising route to industrial-scale biomass refining.

Key words: Oxidative catalysis, Lignin valorization, Aromatic chemicals, Phosphomolybdic acid, Organic acid

曹家铭, 刘玉庭, 刘慧芳, 刘春光, 时君友, 李宁. 多金属氧酸盐/乙酸协同氧化强化木质素高效解聚[J]. 催化学报, 2025, 74: 352-364.

Jiaming Cao, Yuting Liu, Huifang Liu, Chunguang Liu, Junyou Shi, Ning Li. Oxidative depolymerization of lignin enhanced by synergy of polyoxometalate and acetic acid[J]. Chinese Journal of Catalysis, 2025, 74: 352-364.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(25)64737-1

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图/表 8

Fig. 1. Influence of reaction conditions on aromatic monomer yields from birch lignin. (a) Yield of aromatic compounds in different solvents. (b) Yield of aromatic compounds at different concentrations of acetic acid. Reaction conditions: birch lignin:H3PMo12O40 catalyst = 2:1, 160 °C, 2 h, 0.1 MPa O2.

Fig. 2. Lignin oil and aromatic monomer yields under different reaction conditions. (a) Yield of aromatic compounds at different temperatures. Reaction conditions: birch lignin:catalyst = 2:1, 2 h, 0.1 MPa O2, AcOH/H2O = 9:1. (b) Yield of aromatic compounds at different time. Reaction conditions: birch lignin:catalyst = 2:1, 160 °C, 0.1 MPa O2, AcOH/H2O = 9:1. (c) Yield of aromatic compounds at different oxygen pressures. Reaction conditions: birch lignin:catalyst = 2:1, 160 °C, 2 h, AcOH/H2O = 9:1. (The colors of the representative products are consistent with those shown in Fig. 1).

Fig. 3. 2D-HSQC NMR spectra of birch lignin before and after depolymerization catalyzed by H3PMo12O40. (a) Side chain region of birch lignin. (b) Side chain region of the depolymerized product. (c) Aromatic region of birch lignin. (d) Aromatic region of the depolymerized product. Reaction conditions: birch lignin:catalyst = 2:1, AcOH/H2O = 9:1, 160 °C, 2 h, 0.1 MPa O2.

Fig. 4. (a) Reactions of different lignin model compounds. (b) Time relationship plot of the oxidation product yields after reaction of a1. (c) Time relationship plot of the oxidation product yields after reaction of a2.

Table 1 Oxidative reaction of 2-methoxy-4-propylphenol (a3) under different conditions.

Substrate	Catalyst	Atmosphere	Conv. (%)	Yield (mol%)
Substrate	Catalyst	Atmosphere	Conv. (%)	c2	d2	e2	f1
a3 (2-Methoxy-4-propylphenol)	H₃PMo₁₂O₄₀	O₂	87.6	4.3	7.1	21.6	12.8
	H₃PMo₁₂O₄₀	Ar	18.0	—	17.6	—	—
	—	O₂	0	—	—	—	—

Fig. 5. (a) Cyclic voltammetric curves of H3PMo12O40 and AcOH. (b) The FT-IR spectra of different substances containing H3PMo12O40, AcOH. (c) UV-vis spectra of solutions containing various combinations of H3PMo12O40 and AcOH/H2O. (d) UV-vis spectra of H3PMo12O40 in AcOH/H2O solvents at different ratios. (e) Schematic representation of the possible complex structures formed between H3PMo12O40 and AcOH.

Fig. 6. (a) Effects of scavenging agents in model compounds a2 oxidation (Cquencher = 30 mmol·L-1). (b) EPR spectra of reaction mixture with DMPO trapping agent.

Fig. 7. Schematic representation of the presumed major condensation reaction occurring under acidic aqueous conditions (A), and oxidative depolymerization of lignin to aromatic chemicals in acetic acid using H3PMo12O40 as catalyst (B,C).

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多金属氧酸盐/乙酸协同氧化强化木质素高效解聚

Oxidative depolymerization of lignin enhanced by synergy of polyoxometalate and acetic acid

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