乙醇乙醛催化转化制丁二烯的双分子协同吸附机制研究

doi:10.1016/S1872-2067(24)60262-7

催化学报 ›› 2025, Vol. 71: 297-307.DOI: 10.1016/S1872-2067(24)60262-7

乙醇乙醛催化转化制丁二烯的双分子协同吸附机制研究

李显泉^a^,^b^,¹, 庞纪峰^a^,¹, 赵于嘉^a^,^b, 李林^a, 于文广^c, 徐斐斐^c, 苏扬^a, 杨小峰^a, 罗文豪^a^,^d, 郑明远^a^,^c^,^*()

^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中国科学院大连化学物理研究所, 洁净能源国家实验室, 辽宁大连 116023
^d内蒙古大学化学化工学院, 内蒙古呼和浩特 010021

收稿日期:2024-11-05 接受日期:2025-01-20 出版日期:2025-04-18 发布日期:2025-04-13
通讯作者: * 电子信箱: myzheng@dicp.ac.cn (郑明远).
作者简介:
¹共同第一作者.
基金资助:
国家自然科学基金(22378383);国家自然科学基金单原子催化基础研究中心(22388102);中国科学院战略重点研究项目“清洁能源转化技术与示范”(XDA 21060200)

Identifying a bi-molecular synergetic adsorption mechanism for catalytic transformation of ethanol/acetaldehyde into 1,3-butadiene

Xianquan Li^a^,^b^,¹, Jifeng Pang^a^,¹, Yujia Zhao^a^,^b, Lin Li^a, Wenguang Yu^c, Feifei Xu^c, Yang Su^a, Xiaofeng Yang^a, Wenhao Luo^a^,^d, Mingyuan Zheng^a^,^c^,^*()

^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
^cDalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^dCollege of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, Inner Mongolia, China

Received:2024-11-05 Accepted:2025-01-20 Online:2025-04-18 Published:2025-04-13
Contact: * E-mail: myzheng@dicp.ac.cn (M. Zheng).
About author:
¹Contributed to this work equally.
Supported by:
National Science Foundation of China(22378383);NSFC Center for Single-Atom Catalysis(22388102);Strategic Priority Research Program of the Chinese Academy of Sciences(XDA 21060200)

摘要/Abstract

摘要：

将可再生的乙醇催化转化为高附加值化学品如1,3-丁二烯, 可有效降低对石油等不可再生资源的依赖, 具有重要社会意义和应用价值. 乙醇制丁二烯的反应过程涉及多步串联反应, 包括乙醇脱氢、羟醛缩合以及米尔温-庞多尔夫-韦利-奥本诺尔还原氧化反应, 整体反应路径复杂. 受限于催化剂上多种金属活性组分的复杂性, 大多数研究并未围绕关键活性中心从分子层面揭示催化过程的微观机制. 此外, 尽管已有研究对反应中间体的形成和反应物的吸附活化步骤进行了探讨, 但分子水平吸附活化机制及其关键中间物种的动态演变鲜有报道.
本文采用两步法乙醇制丁二烯工艺以简化反应步骤和催化剂活性组分, 为明确关键反应步骤中的催化活性位点及其作用机制提供了有利条件. 首先将活性组分Zr负载在MFI分子筛上, 构建乙醇-乙醛制丁二烯所需的Lewis酸位点, 再通过机械化学方法调控Zr/MFI催化剂的微观结构(Zr(OH)(OSi)₃和ZrO_x物种), 制得的催化剂表现出超过70%的丁二烯选择性和120 h的运行稳定性. 综合X射线吸收谱、X射线光电子能谱和低温CO-红外光谱表征结果, 球磨过程中产生的Zr(OH)(OSi)₃被证实为乙醇-乙醛制丁二烯的高活性中心, 其丁二烯的产率分别比ZrO_x和ZrO₂物种高27倍和700倍. 结合密度泛函理论(DFT)计算和乙醇-乙醛温度程序脱附实验、原位傅里叶变换红外光谱及智能重量分析仪等结果, 提出了双分子吸附模型: 乙醇和乙醛分子以双分子模式共同吸附在Zr(OH)(OSi)₃和ZrO_x活性位点上, 而难以共吸附于ZrO₂位点. 共吸附的乙醇分子显著促进乙醛的烯醇化, 有利于羟醛缩合反应和MPVO还原过程, 从而促进丁二烯的生成. DFT结果表明, Zr(OH)(OSi)₃位点上羟醛缩合和MPVO反应的能垒分别是ZrO_x位点的1/2和2/3, 成为Zr(OH)(OSi)₃物种具有高活性和丁二烯高选择性的关键原因. 基于DFT计算和系统的Operando表征, 提出了一种新的乙醇制丁二烯反应的催化循环机制: (1) 反应物乙醛在乙醇的作用下共同吸附在Zr(OH)(OSi)₃位点上并形成烯醇式结构; (2) 发生烯醇式异构的乙醛与气相中的乙醛分子遵循Eley-Rideal机制进行羟醛缩合反应; (3) 共吸附的乙醇分子通过六元环过渡态促进了MPVO还原的H转移过程; (4) 巴豆醇离开活性位点后乙醇、乙醛再依次吸附, 反应进入下一个催化循环.
综上, 本工作深入探究了Zr活性位点在乙醇乙醛反应物活化、C-C偶联和MPVO还原反应中的催化行为, 厘清了不同Zr物种在乙醇制丁二烯反应中的作用机制, 并从分子水平阐明了乙醇制丁二烯的反应机理, 为设计高性能催化剂和深入认识乙醇转化反应的机制提供了理论参考.

关键词: 1,3-丁二烯, 双分子, 共吸附机制, 反应机理, 乙醇转化

Abstract:

The catalytic synthesis of 1,3-butadiene (1,3-BD) from bio-based ethanol offers an alternative and sustainable process beyond petroleum. However, the intrinsic active sites and corresponding mechanism of 1,3-BD formation have not been fully elucidated yet. By correlating systematic characterization results with catalytic performance, the open Zr species, i.e., Zr(OH)(OSi)₃ moieties, were identified as the active site over the Zr/MFI-BM catalysts for the catalytic transformation of ethanol-acetaldehyde into 1,3-BD. In conjunction with controlled experiments and theory calculations, ethanol and acetaldehyde are proposed to synergistically co-adsorb on the Zr(OH)(OSi)₃ species in a bi-molecular mode, which assists the acetaldehyde condensation and accelerates the critical Meerwein-Ponndorf-Verley-Oppenauer reduction, and accordingly promotes 1,3-BD formation. These findings will stimulate the search towards new metal-zeolite combinations for efficient production of value-added 1,3-BD via biomass-derived ethanol and beyond.

Key words: 1,3-Butadiene, Bi-molecular, Co-adsorption-mechanism, Reaction mechanism, Ethanol conversion

李显泉, 庞纪峰, 赵于嘉, 李林, 于文广, 徐斐斐, 苏扬, 杨小峰, 罗文豪, 郑明远. 乙醇乙醛催化转化制丁二烯的双分子协同吸附机制研究[J]. 催化学报, 2025, 71: 297-307.

Xianquan Li, Jifeng Pang, Yujia Zhao, Lin Li, Wenguang Yu, Feifei Xu, Yang Su, Xiaofeng Yang, Wenhao Luo, Mingyuan Zheng. Identifying a bi-molecular synergetic adsorption mechanism for catalytic transformation of ethanol/acetaldehyde into 1,3-butadiene[J]. Chinese Journal of Catalysis, 2025, 71: 297-307.

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Fig. 1. Synthesis and catalytic performance of Zr-based catalysts for the EATB reaction. (a) The main reaction steps for the EATB process. (b) Schematic diagram for the synthesis of Zr/MFI-BM catalysts. (c) Catalytic performance of ZrO2, Zr/MFI, and Zr/MFI-BM catalysts in the EATB reaction. (d) Ethanol-acetaldehyde conversion and 1,3-BD selectivity in the 125 h TOS over Zr/MFI-BM (350 °C, WHSV = 0.64 h?1, ethanol/acetaldehyde = 2).

Fig. 2. Microstructural characterization of Zr-based catalysts. (a) XPS. (b) 29Si MAS NMR. (c) EXAFS spectra. (d) Fitting of k2-weighted EXAFS data. (e) CO-FTIR spectra for typical Zr-based catalysts. (f) Schematic diagram for the Zr(OH)(OSi)3 sites on the Zr/MFI-BM catalyst.

Fig. 3. Identification of the inherent catalytic center of the EATB reaction. FTIR spectra for the adsorption of ethanol (orange line), acetaldehyde (pink line), and reactants mixture (blue line) at 30 °C over ZrO2 (a), Zr/MFI (b) and Zr/MFI-BM (c) catalysts. (d) IGA results of ethanol or/and acetaldehyde chemisorption over ZrO2, Zr/MFI and Zr/MFI-BM catalysts. Productivity of 1,3-BD over ZrO2, Zr/MFI and Zr/MFI-BM catalysts (e) and different Zr active sites (f). ETOH, ACH and ETOH-ACH are abbreviations for ethanol, acetaldehyde, and ethanol-acetaldehyde mixture, respectively.

Fig. 4. Revealing the co-adsorption model for EATB reaction. (a) DFT calculations for Gibbs free energy of ethanol and/or acetaldehyde adsorbed on Zr(OH)(OSi)3 species and (b) the possible reaction pathways.

Fig. 5. The elucidation of the EATB reaction mechanism. DFT calculation for Gibbs free energy of aldol condensation (a) and MPVO step (b) over the ZrOx and Zr(OH)(OSi)3 species. (c) Proposed catalytic cycle for the EATB process over the Zr(OH)(OSi)3 site.

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乙醇乙醛催化转化制丁二烯的双分子协同吸附机制研究

Identifying a bi-molecular synergetic adsorption mechanism for catalytic transformation of ethanol/acetaldehyde into 1,3-butadiene

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