用于生物质基香草醛水相高选择性加氢脱氧的氮掺杂中空碳球负载Pd催化剂的微环境设计和构筑

doi:10.1016/S1872-2067(24)60261-5

催化学报 ›› 2025, Vol. 71: 267-284.DOI: 10.1016/S1872-2067(24)60261-5

用于生物质基香草醛水相高选择性加氢脱氧的氮掺杂中空碳球负载Pd催化剂的微环境设计和构筑

吴君^a^,^*(), 刘立乾^a, 严鑫悦^a, 潘刚^a, 白家豪^a, 王成兵^a, 李福伟^b^,^*(), 李永^a^,^*()

^a陕西科技大学材料科学与工程学院, 无机材料绿色制备与功能化陕西省重点实验室, 陕西西安 710021
^b中国科学院大学化学工程学院, 北京 100049

收稿日期:2024-12-03 接受日期:2025-02-08 出版日期:2025-04-18 发布日期:2025-04-13
通讯作者: * 电子信箱: wjhg168@163.com (吴君), fuweili@ucas.ac.cn (李福伟), yongli@sust.edu.cn (李永).
基金资助:
国家自然科学基金(21902094);国家自然科学基金(22472177);陕西省自然科学基金(2023-JC-QN-0103);中国博士后面上基金(2020M683405);陕西省教育厅科研计划项目(23JK0344)

Microenvironment engineering of nitrogen-doped hollow carbon spheres encapsulated with Pd catalysts for highly selective hydrodeoxygenation of biomass-derived vanillin in water

Jun Wu^a^,^*(), Liqian Liu^a, Xinyue Yan^a, Gang Pan^a, Jiahao Bai^a, Chengbing Wang^a, Fuwei Li^b^,^*(), Yong Li^a^,^*()

^aSchool of Materials Science & Engineering, Shaanxi Key Laboratory of Green Preparation and Functionalization for Inorganic Materials, Shaanxi University of Science & Technology, Xi'an 710021, Shaanxi, China
^bSchool of Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China

Received:2024-12-03 Accepted:2025-02-08 Online:2025-04-18 Published:2025-04-13
Contact: * E-mail: wjhg168@163.com (J. Wu), fuweili@ucas.ac.cn (F. Li), yongli@sust.edu.cn (Y. Li).
Supported by:
National Natural Science Foundation of China(21902094);National Natural Science Foundation of China(22472177);Natural Science Foundation of Shaanxi Province(2023-JC-QN-0103);China Postdoctoral Science Foundation(2020M683405);Scientific Research Program of Shaanxi Provincial Education Department(23JK0344)

摘要/Abstract

摘要：

催化加氢脱氧(HDO)是实现生物质基含氧化合物增值催化转化的关键途径. 开发高效和高选择性的负载型金属催化剂对生物质基香草醛的水相HDO制备高附加值生物燃料至关重要. 负载型金属催化剂的表面微环境(活性金属中心的电子结构和载体的性质)决定了催化剂的加氢脱氧性能. 除活性金属中心的电子性质在调控催化HDO性能的主导作用外, 载体表面润湿性也会影响催化剂在香草醛水相HDO合成2-甲氧基-4-甲基苯酚(MMP)反应中的活性和选择性. 现已报道金属催化体系难以实现活性金属中心电子性质和载体表面润湿性的协同调控, 致使催化剂水相HDO性能还有很大提升空间. 此外, 高温高压苛刻的反应条件对金属催化剂的稳定性和产物选择性造成巨大挑战. 本文以氮掺杂中空碳球(NHCS)负载Pd纳米反应器作为香草醛HDO催化剂, 通过合理调控中空纳米反应器的组成和结构, 精确剪裁金属催化剂的表面微环境以提高其催化HDO性能.
本文制备的氮掺杂中空碳球载体的化学组成和多孔结构对金属催化剂表面微环境影响显著. NHCS中N原子的引入, 一方面能诱导产生电子金属-载体相互作用(EMSI), 调控活性金属的d带中心以提高催化HDO活性和选择性, 另一方面, 还能赋予催化剂表面良好的亲水性, 促进催化剂在水溶剂中均匀分散, 加快反应物对催化活性中心的接触. 本文采用二氧化硅硬模板导向的多巴胺和Pd前驱体的聚合和碳化过程, 研制出一系列氮掺杂中空碳球负载Pd催化剂(Pd@NHCS). 研究发现, 催化剂前驱体焙烧温度对Pd@NHCS的表面微环境包括活性Pd中心的电子性质和NHCS载体的润湿性和多孔结构影响显著. 该系列催化剂在香草醛水相HDO反应中表现出优异的催化性能. 其中, Pd@NHCS-600催化剂在120 °C, 0.1 MPa H₂的水相温和反应条件下实现了香草醛向MMP的100%选择性转化. 催化本征动力学测试证明了Pd@NHCS-600的优异催化HDO活性, 其TOF值为337.77 h⁻¹, 同时具有较低的表观活化能为18.63 kJ/mol. 详细的催化剂结构表征和动力学测试表明Pd@NHCS优异的催化HDO性能取决于独特的表面微环境. Pd@NHCS催化剂具有适宜的亲水性和丰富的孔道结构, 促进催化剂在水介质的均匀分散以及传质过程. 值得注意的是, 催化剂的焙烧温度直接影响NHCS表面N物种的种类和含量. X射线光电子能谱分析证明, NHCS表面吡啶氮物种与Pd活性金属中心的电子相互作用有助于形成富电子活性Pd中心. 结合紫外-可见光光谱和H₂-程序升温脱附等测试, 证明了富电子的活性Pd中心可促进香草醛和H₂的吸附和活化. 理论计算表明了吡啶氮N物种通过EMSI调控活性Pd的d带中心方面的优势, 显著提高反应物的表面吸附和活化. 根据构效关系分析和理论计算结果, 提出了Pd@NHCS催化香草醛HDO合成MMP的反应机理. 另外, Pd@NHCS催化剂在香草醛HDO反应中表现出良好的稳定性. 同时, Pd@NHCS催化剂具有广泛的底物适用性, 适宜于水相选择性催化多种生物质基羰基化合物的HDO转化制备高附加值化学品.
本文提出了一种简单可控的表面微环境调控策略, 成功构筑高效和稳定的氮掺杂中空碳球负载Pd催化剂, 实现了水相、常压温和反应条件下生物质基香草醛高选择性HDO合成MMP, 并阐明了催化体系构效关系和反应机理, 为负载型金属催化剂的设计制备和生物质的高值化利用提供了新思路.

关键词: 微环境调控, 氮掺杂中空碳球, Pd催化剂, 电子金属-载体相互作用, 加氢脱氧, 香草醛

Abstract:

Development of efficient and stable metal catalysts for the selective aqueous phase hydrodeoxygenation (HDO) of biomass-derived oxygenates to value-added biofuels is highly desired. An innovative surface microenvironment modulation strategy was used to construct the nitrogen-doped hollow carbon sphere encapsulated with Pd (Pd@NHCS-X, X: 600-800) nanoreactors for catalytic HDO of biomass-derived vanillin in water. The specific surface microenvironments of Pd@NHCS catalysts including the electronic property of active Pd centers and the surface wettability and porous structure of NHCS supports could be well-controlled by the calcination temperature of catalysts. Intrinsic kinetic evaluations demonstrated that the Pd@NHCS-600 catalyst presented a high turnover frequency of 337.77 h^-1 and a low apparent activation energy of 18.63 kJ/mol. The excellent catalytic HDO performance was attributed to the unique surface microenvironment of Pd@NHCS catalyst based on structure-performance relationship analysis and DFT calculations. It revealed that pyridinic N species dominated the electronic property regulation of Pd sites through electronic metal-support interaction (EMSI) and produced numerous electron-rich active Pd centers, which not only intensified the dissociation and activation of H₂ molecules, but also substantially improved the activation capability of vanillin via the enhanced adsorption of -C=O group. The fine hydrophilicity and abundant porous structure promoted the uniform dispersion of catalyst and ensured the effective access of reactants to catalytic active centers in water. Additionally, the Pd@NHCS-600 catalyst exhibited excellent catalytic stability and broad substrate applicability for the selective aqueous phase HDO of various biomass-derived carbonyl compounds. The proposed surface microenvironment modulation strategy will provide a new consideration for the rational design of high- performance nitrogen-doped carbon-supported metal catalysts for catalytic biomass transformation.

Key words: Microenvironment modulation, Nitrogen-doped hollow carbon sphere, Pd-based catalyst, Electronic metal-support interaction, Hydrodeoxygenation, Vanillin

吴君, 刘立乾, 严鑫悦, 潘刚, 白家豪, 王成兵, 李福伟, 李永. 用于生物质基香草醛水相高选择性加氢脱氧的氮掺杂中空碳球负载Pd催化剂的微环境设计和构筑[J]. 催化学报, 2025, 71: 267-284.

Jun Wu, Liqian Liu, Xinyue Yan, Gang Pan, Jiahao Bai, Chengbing Wang, Fuwei Li, Yong Li. Microenvironment engineering of nitrogen-doped hollow carbon spheres encapsulated with Pd catalysts for highly selective hydrodeoxygenation of biomass-derived vanillin in water[J]. Chinese Journal of Catalysis, 2025, 71: 267-284.

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https://www.cjcatal.com/CN/Y2025/V71/I4/267

图/表 15

Fig. 1. Schematic synthetic route of Pd@NHCS catalysts.

Fig. 2. XRD patterns (a), FTIR spectra (b), and Raman spectra (c) of Pd@NHCS-X (X = 600-800) catalysts. (d) TG/DTG curves of PdCl42--PDA@SiO2 precursor. N2 adsorption-desorption isotherms (e) and the corresponding pore size distribution profiles (f) of Pd@NHCS-X catalysts.

Table 1 The physicochemical properties of Pd@NHCS-X (X: 600-800) catalysts.

Catalyst	S_BET^a (m²/g)	V_pore^a (cm³/g)	D_pore^a (nm)	d_TEM^b (nm)	d_VA^c (nm)	Adsorbed hydrogen^d (μmol/g)	Pd content^e (wt%)	N content^f (at%)
Pd@NHCS-600	275.17	0.55	8.06	6.34	7.38	107.5	6.34	2.21
Pd@NHCS-700	176.32	0.46	10.37	8.37	8.93	70.0	6.63	1.40
Pd@NHCS-800	256.81	0.59	9.21	8.77	9.49	97.5	6.79	1.04

Fig. 3. SEM (a), TEM (b) and high-resolution TEM (c) images of Pd@NHCS-600 catalyst. HAADF-STEM image (d) and the corresponding elemental mapping images (e-i) of C, N, O, and Pd of Pd@NHCS-600 catalyst, respectively.

Table 2 Catalytic HDO of vanillin with different catalysts.

Entry	Catalyst	Conversion (%)	Selectivity (%)
Entry	Catalyst	Conversion (%)	VA	MMP
1	Blank	0	0	0
2	NHCS-600	0	0	0
3	Pd@NHCS-600	100	0	100
4	Pd@NHCS-700	95	10	90
5	Pd@NHCS-800	52	10	90
6	Pt@NHCS-600	10	100	0
7	Ru@NHCS-600	55	43	57
8	Co@NHCS-600	0	0	0
9	Ni@NHCS-600	0	0	0
10	Cu@NHCS-600	0	0	0
11	Pd@HCS-600	66	26	74
12	Pd@NC-600	59	47	53
13	Pd@NCS@SiO₂-600	57	44	56

Fig. 4. Effect of reaction parameters on catalytic HDO of vanillin over Pd@NHCS-600 catalyst: reaction temperature (a), catalyst dosage (b) and reaction time (c). (d) Catalyst stability study for HDO of vanillin over Pd@NHCS-600 catalyst. Reaction conditions: vanillin 0.5 mmol, catalyst 5 mg, water 5 mL, H2 0.1 MPa, 120 °C, 6 h.

Fig. 5. (a) UV-vis spectra of vanillin adsorption on Pd@NHCS-600 catalyst in water and ethanol, respectively. The adsorption profiles of vanillin (b) and vanillyl alcohol (c) on Pd@NHCS-600 catalyst in water and ethanol.

Fig. 6. Kinetic study on the selective HDO of vanillin over Pd@NHCS-X catalysts. ln(Ct/C0) vs. reaction time plots of Pd@NHCS-600 (a), Pd@NHCS-700 (b), and Pd@NHCS-800 (c) catalysts at 80-100 °C. C refers to the concentration of vanillin. The corresponding Arrhenius plots of Pd@NHCS-600 (d), Pd@NHCS-700 (e), and Pd@NHCS-800 (f) catalysts.

Fig. 7. The dynamic evolution process of water contact angles over Pd@NHCS-600 (a), Pd@NHCS-700 (b), and Pd@NHCS-800 (c) catalysts. (d) Optical photographs of Pd@NHCS-600 catalyst dispersed in water and the mixed solvent composed of water and ethyl acetate. (e) H2-TPD profiles of Pd@NHCS-X catalysts. (f) UV-vis spectra of vanillin adsorption on Pd@NHCS-X and NHCS-600 catalysts.

Fig. 8. High-resolution XPS spectra of N 1s (a), Pd 3d (b) and the contents of various N species (c) for Pd@NHCS-X catalysts. (d) Schematic diagrams of the pyridinic N and graphitic N configurations incorporated into the Pd@NHCS catalyst.

Fig. 9. (a) The binding energies of pyridinic N and graphitic N species of Pd@NHCS-X catalysts and the corresponding NHCS-X supports. (b) The binding energy of Pd0 species and the corresponding energy offsets of pyridinic-N and graphitic-N species of Pd@NHCS-X. (c) Dependences of NP/NG ratio of Pd@NHCS-X catalysts, the corresponding NHCS-X supports and their energy offsets of pyridinic-N and graphitic-N species on calcination temperature of catalyst. (d) Dependences of the binding energies of pyridinic N and graphitic N species and the binding energy of Pd0 species on Pd loading. The relationships between TOF value and Pd species content (e), N species content (f) for Pd@NHCS-X catalysts.

Fig. 10. Charge density difference and electron transfer amount of pyridinic N-doped carbon supported Pd (a) and graphitic N-doped carbon supported Pd (c), the yellow and cyan areas refer to the increase and decrease in charge density, respectively. The top view and two-dimensional charge density difference of pyridinic N-doped carbon supported Pd in (a) (b), and graphitic N-doped carbon supported Pd in (c) (d). The red and blue areas refer to the electron accumulation and depletion, respectively. (e) Calculated density of states of the structure in (a-d). (f) Adsorption energies of vanillin binding with pyridinic N and graphitic N-doped carbon supported Pd catalysts, respectively.

Fig. 11. Schematic of reaction mechanism for vanillin HDO over Pd@NHCS catalyst.

Scheme 1. The scale-up experiment of vanillin HDO over Pd@NHCS-600 catalyst. Reaction conditions: vanillin 5 mmol, catalyst 50 mg, water 10 mL.

Table 3 Catalytic HDO of various biomass-derived aldehyde and ketone derivates over Pd@NHCS-600 catalyst a.

Entry	Conversion (%)	Selectivity (%)
1	100	100
2^b	94	87
3^b	95	99
4^c	92	95
5^c	96	100
6	100	100
7^d	100	72
8^e	100	100
9^b	99	100
10^b	93	98
11	100	100
12	78	100
13	71	100

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用于生物质基香草醛水相高选择性加氢脱氧的氮掺杂中空碳球负载Pd催化剂的微环境设计和构筑

Microenvironment engineering of nitrogen-doped hollow carbon spheres encapsulated with Pd catalysts for highly selective hydrodeoxygenation of biomass-derived vanillin in water

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