具有富电子镍位点的耐酸金属间化合物CaNi2Si2催化剂用于不饱和有机酸酐/酸的水相加氢

doi:10.1016/S1872-2067(23)64473-0

催化学报 ›› 2023, Vol. 50: 260-272.DOI: 10.1016/S1872-2067(23)64473-0

具有富电子镍位点的耐酸金属间化合物CaNi₂Si₂催化剂用于不饱和有机酸酐/酸的水相加氢

刘诗瑶^a^,¹, 巩玉同^b^,¹, 杨晓^b, 张楠楠^a, 刘会斌^a, 梁长海^a^,^*(), 陈霄^a^,^*()

^a大连理工大学化工学院精细化工国家重点实验室, 先进材料与催化工程实验室, 辽宁大连 116024
^b西北工业大学材料学院凝固技术国家重点实验室, 陕西西安 710072

收稿日期:2023-03-22 接受日期:2023-06-05 出版日期:2023-07-18 发布日期:2023-07-25
通讯作者: *电子邮箱: changhai@dlut.edu.cn (梁长海), xiaochen@dlut.edu.cn (陈霄).
作者简介:
¹共同第一作者.
基金资助:
国家自然科学基金(22272014);国家自然科学基金(22172016);国家自然科学基金(22161132005);中央高校基本科研业务费专项资金(DUT21TD103);博士后研究基金(2021M692634)

Acid-durable intermetallic CaNi₂Si₂ catalyst with electron-rich Ni sites for aqueous phase hydrogenation of unsaturated organic anhydrides/acids

Shiyao Liu^a^,¹, Yutong Gong^b^,¹, Xiao Yang^b, Nannan Zhang^a, Huibin Liu^a, Changhai Liang^a^,^*(), Xiao Chen^a^,^*()

^aState Key Laboratory of Fine Chemicals, Laboratory of Advanced Materials and Catalytic Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, China
^bState Key Laboratory of Solidification Processing, School of Materials Science and Engineering, Northwestern Polytechnical University, Xi'an 710072, Shaanxi, China

Received:2023-03-22 Accepted:2023-06-05 Online:2023-07-18 Published:2023-07-25
Contact: *E-mail: changhai@dlut.edu.cn (C. Liang), E-mail: xiaochen@dlut.edu.cn (X. Chen).
About author:
¹Contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22272014);National Natural Science Foundation of China(22172016);National Natural Science Foundation of China(22161132005);Fundamental Research Funds for the Central Universities(DUT21TD103);Postdoctoral Research Foundation of China(2021M692634)

摘要/Abstract

摘要：

顺酐水相加氢制备下游产物丁二酸, 是一种合成生物可降解塑料聚丁二酸丁二醇酯的重要单体. 在水相体系中, 顺酐迅速水解生成顺丁烯二酸, 表现出较强的酸性, 对催化剂耐酸稳定性要求较高. 贵金属催化剂通常表现出较高的顺酐加氢活性, 但由于其与底物分子结合能力较强, 容易生成深度加氢或氢解产物, 并且贵金属高昂的价格也限制了其进一步应用. 此外, 工业上常用的负载型Ni基催化剂的活性和稳定性也有待进一步提高. 因此, 在顺酐水相直接加氢生成丁二酸的过程中开发高活性和高稳定性的非贵金属基催化剂具有重要意义. 金属硅化物作为一种新型的金属间化合物催化材料, 常作为非均相催化剂应用, 尤其对涉氢反应表现出较高的活性和选择性, 并且由于硅原子的掺入, 调变了活性位点的几何和电子结构, 使其展现出较好的催化活性、耐酸碱腐蚀性和热稳定性, 有望用于顺酐直接水相加氢反应制备丁二酸.

本文采用新型低温熔盐技术成功制备了一种单相的、元素分散均匀以及高比表的CaNi₂Si₂金属间化合物纳米催化剂, 并将其应用于顺酐连续水相加氢制备丁二酸的反应体系中, 可以有效解决该体系存在的瓶颈问题. 采用X射线衍射Rietveld精修技术、X射线光电子能谱深度剖析、紫外光电子能谱和态密度分析等手段对CaNi₂Si₂催化剂的几何和电子结构进行剖析. 并采用模型化合物丙烯酸原位漫反射傅里叶变换红外光谱、原位程序升温脱附/表面反应及密度泛函理论计算等研究了CaNi₂Si₂催化顺酐加氢反应机理, 并剖析构效关系. 结果表明CaNi₂Si₂催化剂中电子由Ca向Ni和Si发生转移, 并证明了这种富电子Ni活性位点的协同作用有利于其对底物分子中C=C键选择性吸附和H₂的活化, 从而使其展现出较好的目标产物丁二酸的选择性. 在3 MPa, 120 °C, 接触时间5.4 g_cat/(mmol_reactant·min^‒1)条件下, 丁二酸产率可达到100%. 此外, 相比于负载型Ni/SBA-15催化剂(51.90 kJ/mol), CaNi₂Si₂展现出更低的表观活化能(46.39 kJ/mol), 从本征活性证明了其作为顺酐水相加氢催化剂的优势. 稳定性测试结果表明, 与Ni/SBA-15相比, 由于CaNi₂Si₂中Ni特殊的配位环境和电子结构抑制了羧酸盐的形成, 有效减少了活性金属Ni位点的流失, 从而有效的提高了其在顺酐水溶液(2 wt%, pH = 1.51)中的耐酸腐蚀性能, 使其表现出高活性的同时具有较好稳定性, 在一定程度上可替代贵金属催化剂. 同时, 底物扩展实验也证明了CaNi₂Si₂作为一种催化新材料在不饱和链状或环状有机酸/酸酐的加氢性能反应中均能展现出较好的活性, 说明了CaNi₂Si₂作为非贵金属催化剂在酸酐加氢领域具有巨大潜力. 总之, 金属硅化物的精细设计和结构调控将为顺酐加氢催化剂的可控优化提供重要参考, 并为设计高效稳定的苛刻反应中选择性加氢催化剂提供新的思路.

关键词: CaNi₂Si₂, 金属间化合物, 富电子镍活性位点, 选择性加氢, 丁二酸

Abstract:

The study of the aqueous-phase selective hydrogenation of maleic anhydride to succinic acid is important for expanding the coal chemical industry chain and promoting biomass conversion. The key lies in the development of highly efficient and stable non-noble metal catalysts. Herein, we report a novel intermetallic CaNi₂Si₂ catalyst with high activity and stability for the aqueous-phase selective hydrogenation of maleic anhydride. The results from the experiments and theoretical calculations demonstrated that the high catalytic performance was due to the synergy of the electron-rich Ni active sites, enhanced adsorption of C=C bonds, and favorable activation of H₂. The yield of succinic acid can be 100% over the CaNi₂Si₂ catalyst at the contact time of 5.4 g_cat/(mmol_reactant·min^-1) under 3 MPa and 120 °C in the continuous flow reactor. Furthermore, the special coordination environment and electronic structure of Ni in CaNi₂Si₂ inhibit the formation of carboxylates, thus enhancing the acid resistance in the reaction environment. The fine design and regulation of the structure of intermetallic silicides will be important references for the controllable optimization of maleic anhydride hydrogenation catalysts and provide new insights into the development of efficient and stable selective hydrogenation catalysts in harsh reaction environments.

Key words: CaNi₂Si₂, Intermetallic compound, Electron-rich Ni active site, Selective hydrogenation, Succinic acid

刘诗瑶, 巩玉同, 杨晓, 张楠楠, 刘会斌, 梁长海, 陈霄. 具有富电子镍位点的耐酸金属间化合物CaNi₂Si₂催化剂用于不饱和有机酸酐/酸的水相加氢[J]. 催化学报, 2023, 50: 260-272.

Shiyao Liu, Yutong Gong, Xiao Yang, Nannan Zhang, Huibin Liu, Changhai Liang, Xiao Chen. Acid-durable intermetallic CaNi₂Si₂ catalyst with electron-rich Ni sites for aqueous phase hydrogenation of unsaturated organic anhydrides/acids[J]. Chinese Journal of Catalysis, 2023, 50: 260-272.

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图/表 9

Fig. 1. (a) Schematic showing synthetic steps for CaNi2Si2 NPs. (b) Crystal structure and powder XRD pattern of CaNi2Si2 sample with Rietveld analysis. (c) WF (?) calculated from the measurement of secondary electron cut-off using UPS at a bias voltage of 6 V. H2-TPR (d) and H2-TPD (e) profiles of CaNi2Si2, Ni2Si, and Ni/SBA-15 samples.

Fig. 2. TEM (a), HRTEM (b), and HAADF-STEM (c) images with the corresponding EDS mappings of CaNi2Si2 sample.

Fig. 3. (a) XPS spectra of Ni 2p, Ca 2p, Si 2p, and O 1s of CaNi2Si2 after Ar+ sputtering. (b) Bader charges of CaNi2Si2 and 3D electron density isosurface map in the region from -0.5 eV to EF at 0.0025 A-3. (c) Calculated electronic DOS of CaNi2Si2 (112)-Ni and Ni metal (111)-Ni. The dotted lines are the d-band centers of CaNi2Si2 (112)-Ni (-1.35 eV) and Ni metal (111)-Ni (-1.06 eV), respectively.

Fig. 4. (a) Reaction pathway for the hydrogenation of MAn in the aqueous phase. (b) Comparison of the catalytic performance of different catalysts (CaNi2Si2, Ni2Si, CaSi2, Ni/SBA-15, and SBA-15). Effect of reaction temperature (c) and H2 pressure (d) on the hydrogenation of MAn in the aqueous phase over CaNi2Si2 (2.0 wt% of MAn aqueous and 0.2 g catalyst). (e) Product distribution for the hydrogenation of MAn in the aqueous phase over CaNi2Si2 catalyst at 3 MPa and 120 °C.

Fig. 5. Kinetic equilibrium constant (a-d) and Arrhenius plot (e) for aqueous phase hydrogenation of MAn (The Ea was estimated in the range of 60-120 °C for controlling the conversion of MAc below 30%).

Fig. 6. Stability tests of the CaNi2Si2 (a) and Ni/SBA-15 (b) for the aqueous-phase hydrogenation of MAn (The inset images display the photos of products at different reaction times and the fresh and spent catalysts).

Table 1 Hydrogenation of other unsaturated organic acids/anhydrides over CaNi2Si2.

Entry	Substrate	Product	pH	Reaction condition		Contact time (g_cat/(mmol·min^-1))	Conv. (%)	Sel. (%)
Entry	Substrate	Product	pH	T (°C)	P (MPa)	Contact time (g_cat/(mmol·min^-1))	Conv. (%)	Sel. (%)
1^a			2.52	100	1	14.4	100	100
2^a			2.64	120	3	2.1	100	99
3^a			2.33	120	3	4.5	100	99
4^a			1.81	120	3	8.4	92	100
5^a			2.04	240	3	4.5	98	95
6^b			1.95	120	3	5.0 h	100	97

Fig. 7. TPD (a) and TPSR (b) profiles of acrylic acid over the CaNi2Si2 catalyst. (c) DRIFT spectra of acrylic acid desorbed on CaNi2Si2 under Ar flow at 30, 50, and 100 °C. (d) DRIFT spectra of acrylic acid over the CaNi2Si2 catalyst in 10 vol% H2/Ar.

Fig. 8. DFT-calculated models of the carboxyl C=O bonds of acrylic acid on CaNi2Si2 (112)-top (a-d) and metallic Ni (111)-top (e-f).

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具有富电子镍位点的耐酸金属间化合物CaNi₂Si₂催化剂用于不饱和有机酸酐/酸的水相加氢

Acid-durable intermetallic CaNi₂Si₂ catalyst with electron-rich Ni sites for aqueous phase hydrogenation of unsaturated organic anhydrides/acids

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