氮掺杂碳层包覆纳米金催化5-羟甲基糠醛非临氢转化制5-甲基糠醛

doi:10.1016/S1872-2067(21)64049-4

催化学报 ›› 2022, Vol. 43 ›› Issue (8): 2212-2222.DOI: 10.1016/S1872-2067(21)64049-4

氮掺杂碳层包覆纳米金催化5-羟甲基糠醛非临氢转化制5-甲基糠醛

张姜^a, 王子剑^a, 陈慕耕^a, 朱义峰^a, 刘永梅^a, 贺鹤勇^a, 曹勇^a^,^*(), 包信和^a^,^b^,^#()

^a复旦大学化学系, 分子催化和功能材料重点实验室, 上海200433
^b中国科学院大连化学物理研究所, 洁净能源国家实验室, 催化国家重点实验室, 辽宁大连116023

收稿日期:2022-03-06 接受日期:2022-03-09 出版日期:2022-08-18 发布日期:2022-06-20
通讯作者: 曹勇,包信和
基金资助:
国家自然科学基金(21972024);国家自然科学基金(21773033);国家自然科学基金(22088101);上海市科学技术委员会(19DZ2270100);上海市科学技术委员会(20ZR1404600);中国石化(X514005)

N-doped carbon layer-coated Au nanocatalyst for H₂-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural

Jiang Zhang^a, Zijian Wang^a, Mugeng Chen^a, Yifeng Zhu^a, Yongmei Liu^a, Heyong He^a, Yong Cao^a^,^*(), Xinhe Bao^a^,^b^,^#()

^aShanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, Shanghai 200433, China
^bState Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2022-03-06 Accepted:2022-03-09 Online:2022-08-18 Published:2022-06-20
Contact: Yong Cao, Xinhe Bao
Supported by:
National Natural Science Foundation of China(21972024);National Natural Science Foundation of China(21773033);National Natural Science Foundation of China(22088101);Science & Technology Commission of Shanghai Municipality(19DZ2270100);Science & Technology Commission of Shanghai Municipality(20ZR1404600);SINOPEC(X514005)

摘要/Abstract

摘要：

生物质资源丰富、价格低廉, 是有机碳的唯一可持续与可再生来源, 如能将其有效转化将足以满足人类对燃料和化学品日益增长的需求. 生物质衍生的5-羟甲基糠醛(HMF)具有良好的反应性能, 被誉为有望跨越化石能源经济与可持续经济之间鸿沟的关键平台分子. 但HMF高度不稳定及见光易分解等缺点很大程度上限制了其广泛应用, 基于此, 5-甲基糠醛(5-MF)是一种HMF的脱氧衍生物, 作为另一种有前途的平台化合物近期引起了广泛关注. 目前, 由HMF直接转化制5-MF的报道相对较少, 且存在需使用氢气或效率较低等问题. 如何利用生物质衍生的甲酸(FA)作为氢源, 高效的将HMF转化为5-MF仍存在挑战.

本文设计合成了一种氮掺杂的多孔碳层(NPC)包覆的纳米金催化剂(Au-4/TiO₂@NPC), 用于HMF催化转化, 以FA为氢源, 实现了5-MF的高选择性和高收率合成. 采用简单的两步法制备Au-4/TiO₂@NPC. 用沉积-沉淀法制得具有均一尺寸(约为4 nm)纳米Au的Au-4/TiO₂, 再将其置于多巴胺溶液中利用多巴胺的自氧化作用在其表面形成一层聚多巴胺(PDA)膜, 经高温煅烧将PDA膜转化为NPC层. 系统考察了Au粒径、多巴胺浓度和煅烧温度等条件对催化剂活性的影响. 最佳催化剂Au-4/TiO₂@NPC在4倍化学计量的FA(相较HMF)和180 ^oC条件下反应1.5 h, HMF 100%转化, 5-MF收率达95%, 其性能远高于无NPC包覆的Au-4/TiO₂以及半包覆的催化剂. X射线光电子能谱结果表明, 催化剂中Au具有明显的电子结合能偏移, 表明Au呈富电子状态. 一氧化碳-原位红外漫反射结果表明, Au-CO线式吸附峰发生红移, NPC向Au转移电子. 为进一步探究其高活性的原因, 测试了不同催化剂对关键反应步骤即中间产物脱羧和甲酸分解的性能. 结果表明, Au-4/TiO₂@NPC促进了HMF与FA的优先酯化并显著抑制了FA的无效分解, 由此促进了HMF中羟基的选择性甲酰化-脱羧, 从而促进了5-MF的生成. 此外, 得益于PDA衍生的氮掺杂多孔碳层的稳定化作用, 该催化剂可有效阻止Au纳米颗粒在反应条件下的团聚烧结, 表现出较好的稳定性. 本文提出的催化剂制备策略为面向生物质资源可控转化的多相催化剂的理性设计提供了潜在指导.

关键词: 5-羟甲基糠醛, 5-甲基糠醛, 金催化, 氮掺杂的多孔碳, 生物质炼制

Abstract:

Deoxygenative upgrading of 5-hydromethylfurfural (HMF) into valuable chemicals has attracted intensive research interest in recent years, with product selectivity control remaining an important topic. Herein, TiO₂ supported gold catalysts coated with a thin N-doped porous carbon (NPC) layer were developed via a polydopamine-coating-carbonization strategy and utilized for pathway-specific conversion of HMF into 5-methylfurfural (5-MF) with the use of renewable formic acid (FA) as the deoxygenation reagent. The as-fabricated Au/TiO₂@NPC exhibited excellent catalytic performance with a high yield of 5-MF (>95%). The catalytic behavior of Au@NPC-based catalysts was shown to be correlated with the suitable combination of highly dispersed Au nanoparticles and favorable interfacial interactions in the Au@NPC core-shell hetero-nanoarchitectures, thereby facilitating the preferential esterification of HMF with FA and suppressing unproductive FA dehydrogenation, which promoted the selective formylation/decarboxylation of hydroxy-methyl group in HMF in a pathway-specific manner. The present NPC/metal interfacial engineering strategy may provide a potential guide for the rational design of advanced catalysts for a wide variety of heterogeneous catalysis processes in terms of the conversion of biomass source.

Key words: 5-Hydroxymethylfurfural, 5-Methylfurfural, Gold catalysis, N-doped porous carbon, Biomass upgrading

张姜, 王子剑, 陈慕耕, 朱义峰, 刘永梅, 贺鹤勇, 曹勇, 包信和. 氮掺杂碳层包覆纳米金催化5-羟甲基糠醛非临氢转化制5-甲基糠醛[J]. 催化学报, 2022, 43(8): 2212-2222.

Jiang Zhang, Zijian Wang, Mugeng Chen, Yifeng Zhu, Yongmei Liu, Heyong He, Yong Cao, Xinhe Bao. N-doped carbon layer-coated Au nanocatalyst for H₂-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural[J]. Chinese Journal of Catalysis, 2022, 43(8): 2212-2222.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(21)64049-4

https://www.cjcatal.com/CN/Y2022/V43/I8/2212

图/表 11

Scheme 1. Production of bio-based chemicals or fuels by 5-MF or HMF [14].

Scheme 2. Routes for 5-MF synthesis.

Scheme 3. Schematic illustration of the synthesis procedure of Au-n/TiO2@NPC-T.

Fig. 1. (a) TEM image and particle size distribution; HRTEM images (b,c), HAADF-STEM images and corresponding EDX elemental mapping (d) of Au-4/TiO2@NPC.

Fig. 2. CO-DRIFT spectra (a) as well as XPS in the Au 4f (b) and N 1s (c) region of Au-4/TiO2@NPC-T. (1) Au-4/TiO2@NPC-500; (2) Au-4/TiO2@NPC; (3) Au-4/TiO2@NPC-700; (4) Au-4/TiO2@NPC-800.

Table 1 FA-mediated catalytic conversion of HMF into 5-MF using various catalysts.

Entry	Catalysts	Carbon balance (%)	Conversion (%)	Yield (%)
Entry	Catalysts	Carbon balance (%)	Conversion (%)	1	2	3	4	5	others
1	Au/TiO₂-4	>99	>99	—	31	34	—	35	—
2	Au-4/TiO₂@NPC	>99	>99	—	95	—	—	5	—
3 ^a	Au-4/TiO₂@NPC	>99	>99	—	90	—	—	9	1
4 ^b	Au-4/TiO₂@NPC	>99	>99	2	92	—	—	6	—
5	Au_em/TiO₂@NPC	>99	>99	—	81	—	—	19	—
6	Au-4/TiO₂@NPC(5%)	>99	>99	—	90	—	—	10	—
7	Au-4/TiO₂@NPC(15%)	>99	94	6	85	—	2	1	—
8	Au-4/TiO₂@NPC-500	>99	>99	9	89	—	—	2	—
9	Au-4/TiO₂@NPC-700	>99	>99	4	90	—	—	6	—
10	Au-4/TiO₂@NPC-800	>99	>99	—	87	—	—	13	—
11	Au-2/TiO₂@NPC-600	>99	>99	—	89	—	—	11	—
12	Au-3/TiO₂@NPC-600	>99	>99	—	91	—	—	9	—
13	Au-5/TiO₂@NPC-600	>99	99	4	93	—	—	2	—

Fig. 3. (a) Reuse of Au-4/TiO2@NPC in the HMF-to-5-MF transformation (reaction time 10 min). (b) TEM image and particle size distribution of Au-4/TiO2@NPC after reused six times; XPS characterization of Au 4f (c) and CO-DRIFT spectra (d) of Au-4/TiO2@NPC before and after reaction.

Fig. 4. TEM images of Auem/TiO2@NPC.

Fig. 5. Reaction progress of FA-mediated HMF conversion to 5-MF. (a) Time course plot. (b) Reaction network for FA-mediated HMF conversion to 5-MF. Reaction conditions: 1 mmol HMF, 4 mmol FA, Au-4/TiO2@NPC 0.4 mol%, 0.1 MPa N2, 10 mL 1,4-dioxane, 180 °C. Note: HFF: 2-hydroxy-5-fururfylformate, 5-MFF: 5-methylfururfylformate.

Fig. 6. FMF decomposition and FA decomposition over various catalysts. Reaction conditions: 1 mmol substrate, catalyst 0.04 mol%, 0.1 MPa N2, 10 mL 1,4-dioxane, 180 °C, TOF values based on 15% conversion of substrate.

Table 2 FA-mediated hydrodeoxygenation of different substrates over the Au-4/TiO2@NPC catalyst.

Entry	Time (h)	FA (mmol)
1	1.5	4	>99	94
2	1.5	4	>99	92
3	1.5	4	>99	96
4	3	8	>99	93
5	1.5	4	>99	99
6	2.5	4	>99	97
7	1.5	4	trace	trace
8	1.5	4	trace	trace

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氮掺杂碳层包覆纳米金催化5-羟甲基糠醛非临氢转化制5-甲基糠醛

N-doped carbon layer-coated Au nanocatalyst for H₂-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural

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氮掺杂碳层包覆纳米金催化5-羟甲基糠醛非临氢转化制5-甲基糠醛

N-doped carbon layer-coated Au nanocatalyst for H2-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural

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N-doped carbon layer-coated Au nanocatalyst for H₂-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural