氟离子介导酸性体系合成H-ZSM-5分子筛及其液相环己醇催化转化性能研究

doi:10.1016/S1872-2067(25)64718-8

催化学报 ›› 2025, Vol. 74: 97-107.DOI: 10.1016/S1872-2067(25)64718-8

氟离子介导酸性体系合成H-ZSM-5分子筛及其液相环己醇催化转化性能研究

衣启松^a^,^b^,¹, 林露^a^,¹, 耿华伟^a, 陈少华^c, 邵元超^a, 何平^a, 刘志峰^a, 许海梅^a, 陈铁红^c, 刘远帅^a^,^*(), Valentin Valtchev^a^,^d^,^*()

^a中国科学院青岛生物能源与过程研究所, 山东能源研究院, 青岛新能源山东省实验室, 山东青岛 266101, 中国
^b中国科学院大学, 北京 100049, 中国
^c南开大学先进能源材料化学教育部重点实验室, 新催化材料科学研究所, 天津 300350, 中国
^d卡昂大学法国国家科学研究中心, 催化与光谱化学实验室, 卡昂, 法国

收稿日期:2025-01-10 接受日期:2025-04-01 出版日期:2025-07-18 发布日期:2025-07-20
通讯作者: *电子信箱: liuys@qibebt.ac.cn (刘远帅),valentin.valtchev@ensicaen.fr (V. Valtchev).
作者简介:¹共同第一作者.
基金资助:
国家自然科学基金(22109167);国家自然科学基金(22479152);山东省自然科学基金(2022HWYQ-088);泰山学者项目(tsqn202211260)

Benefits of H-ZSM-5 zeolite from fluoride-mediated acidic synthesis for liquid-phase conversion of cyclohexanol

Qisong Yi^a^,^b^,¹, Lu Lin^a^,¹, Huawei Geng^a, Shaohua Chen^c, Yuanchao Shao^a, Ping He^a, Zhifeng Liu^a, Haimei Xu^a, Tiehong Chen^c, Yuanshuai Liu^a^,^*(), Valentin Valtchev^a^,^d^,^*()

^aShandong Energy Institute, Qingdao Energy Shandong Laboratory, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Science, Qingdao 266101, Shandong, China
^bUniversity of Chinese Academy of Sciences, Beijing 100049, China
^cKey Laboratory of Advanced Energy Materials Chemistry, Institute of New Catalytic Materials Science, Nankai University, Tianjin 300350, China
^dUniversité de Caen Normandie, ENSICAEN, CNRS, LCS, 14000 Caen, France

Received:2025-01-10 Accepted:2025-04-01 Online:2025-07-18 Published:2025-07-20
Contact: *E-mail: liuys@qibebt.ac.cn (Y. Liu), valentin.valtchev@ensicaen.fr (V. Valtchev).
About author:¹Contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22109167);National Natural Science Foundation of China(22479152);Natural Science Foundation of Shandong Province(2022HWYQ-088);Taishan Scholars Program(tsqn202211260)

摘要/Abstract

摘要：

随着全球能源危机的加剧, 传统化石能源已难以满足日益增长的能源需求. 在此背景下, 将可再生的生物质资源转化为高值化学品吸引越来越多的研究兴趣. 分子筛具有高比表面积、规则的孔道结构及可调变的表面酸性, 可作为催化剂或催化剂载体使用, 在生物质催化转化领域展现出广阔的应用前景. 然而, 由于生物质分子普遍具有高含氧量和低饱和蒸气压的特性, 其转化过程往往需要在高温含水液-固相反应体系中进行, 这对分子筛催化剂的水热稳定性提出了严峻挑战.

分子筛晶体中的大量羟基缺陷是造成分子筛水热稳定性降低的一个重要原因. 目前改善分子筛水热稳定性的主要方法有: (1)硅烷化后处理修复羟基缺陷, (2)含氟条件下合成低缺陷分子筛. 然而, 硅烷化后处理方法操作繁琐, 并且硅烷化试剂的使用易造成分子筛微孔堵塞; 而含氟体系制备的分子筛晶体通常尺寸较大, 不利于传质扩散. 针对以上问题, 本研究在含氟酸性介质中成功合成具有优异水热稳定性的b轴取向ZSM-5分子筛(H-ZSM-5(A)). 通过红外光谱和水吸附测试比较了H-ZSM-5(A)分子筛以及常规碱性条件下合成的H-ZSM-5(B)分子筛的骨架缺陷浓度和表面性质; 结果表明, 酸性条件下制备H-ZSM-5(A)分子筛的羟基缺陷含量更少, 这赋予其显著增强的疏水特性. 进一步使用环己醇脱水模型反应研究两种分子筛的水热稳定性; 结果表明, 碱性条件制备H-ZSM-5(B)在200 °C水热处理10 d后催化活性降低超过一半, 而酸性条件下制备H-ZSM-5(A)分子筛活性仍然保持不变, 表明其水热稳定性较好. 催化反应动力学结果进一步表明, H-ZSM-5(A)相较于H-ZSM-5(B)具有更高的初始脱水反应速率和更低的环己醇脱水表观反应活化能垒, 这主要归因于两者不同的亲疏水特性. H-ZSM-5(A)和H-ZSM-5(B)在环己醇脱水过程中表现出不同的反应路径, 即H-ZSM-5(A)更倾向于发生环己醇单体脱水反应路线, 而H-ZSM-5(B)中存在醇二聚体脱水的反应路径. 此外, 亲水性的增强也可能导致H-ZSM-5(B)表面环己醇浓度更高, 造成相分离现象, 产生额外的吸附及扩散壁垒, 进而增加反应活化能垒, 降低了反应速率. 最后, 使用吡啶为探针分子的红外光谱以及¹H, ²⁹Si和²⁷Al魔角旋转核磁共振谱分析H-ZSM-5(A)和H-ZSM-5(B)样品水热处理前后酸性及结构性质变化发现: 由于羟基缺陷位点的含量减少, 分子筛表面疏水性增强, H-ZSM-5(A)水热处理前后未发生明显脱铝及脱硅现象, 酸性位含量和分布基本保持不变, 进而在环己醇脱水反应中表现出优异的水热稳定性.

综上, 本研究系统探究了氟离子介导酸性体系中b轴取向H-ZSM-5分子筛的制备, 并以环己醇脱水作为探针反应, 深入揭示了分子筛表面亲疏水性对催化剂活性及稳定性的调控机制, 为生物质转化过程中高水热稳定性分子筛类催化剂的制备提供了参考.

关键词: 生物质转化, 脱水, 水热稳定性, 动力学, 分子筛

Abstract:

The hydrothermal stability of zeolites is essential for their potential applications in biomass conversion, especially in processes involving elevated temperatures alongside the use or generation of H₂O. In this study, we employed F^- ions as mineralizers to synthesize hydrothermally stable ZSM-5 zeolites under acidic conditions. The acidic synthesis system promotes zeolites with fewer silanol-terminated lattice defects (ZSM-5(A)) compared to the traditional basic conditions (ZSM-5(B)), endowing materials with substantially higher structural integrity and hydrophobicity. After 10 days of autoclave treatment at 200 °C in aqueous phase, H-ZSM-5(A) demonstrated nearly unchanged reaction rates in the dehydration of cyclohexanol, while H-ZSM-5(B) lost > 50% of the dehydration activity. Additionally, H-ZSM-5(A) delivered higher initial dehydration rates compared to H-ZSM-5(B). The different measured activation energies further revealed variations in reaction pathways during cyclohexanol dehydration, i.e., the monomer- or dimer-mediated routes depending on the concentration of alcohol molecule within zeolite pores, providing additional evidence for the strengthened hydrophobic nature of H-ZSM-5(A). Beyond this, the zeolite surface properties and the strength of cyclohexanol-zeolite interactions may impose additional transport/adsorption barriers attributed to multi-phase phenomena on the more polar H-ZSM-5(B) zeolite surfaces. More importantly, the hydrothermal treatment did not induce significant desilication and dealumination in H-ZSM-5(A), thereby preserving its active acid sites and ensuring exceptional hydrothermal stability. The present work fundamentally studies the synthesis of hydrothermally stable zeolites in an acidic medium using fluorides and expands the understanding of polar interactions in catalysis, characterized by the dehydration of cyclohexanol, for future application in biomass conversion.

Key words: Biomass conversion, Dehydration, Hydrothermal stability, Kinetics, Zeolites

衣启松, 林露, 耿华伟, 陈少华, 邵元超, 何平, 刘志峰, 许海梅, 陈铁红, 刘远帅, Valentin Valtchev. 氟离子介导酸性体系合成H-ZSM-5分子筛及其液相环己醇催化转化性能研究[J]. 催化学报, 2025, 74: 97-107.

Qisong Yi, Lu Lin, Huawei Geng, Shaohua Chen, Yuanchao Shao, Ping He, Zhifeng Liu, Haimei Xu, Tiehong Chen, Yuanshuai Liu, Valentin Valtchev. Benefits of H-ZSM-5 zeolite from fluoride-mediated acidic synthesis for liquid-phase conversion of cyclohexanol[J]. Chinese Journal of Catalysis, 2025, 74: 97-107.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(25)64718-8

https://www.cjcatal.com/CN/Y2025/V74/I7/97

图/表 7

Fig. 1. (a) The schematic diagram of ZSM-5 synthesis under acidic conditions. XRD patterns (b) and SEM images (c,d) of H-ZSM-5(A) and H-ZSM-5(B) zeolites. TEM (e,f, inset: SAED spectrum) and mapping images (g) of H-ZSM-5(A) zeolite.

Table 1 Acidity measurements of ZSM-5 zeolites before and after hydrothermal treatment using Py-IR.

Sample	Si/Al^a	Acidity (μmol·g^-1)			B/L	Si/Al^b
Sample	Si/Al^a	BAS	LAS	Total	B/L	Si/Al^b
H-ZSM-5(A)	75 (± 8)	230	10	240	23	—
H-ZSM-5(A)-H-10d	80 (± 5)	220	11	231	20	579 (± 21)
H-ZSM-5(B)	73 (± 6)	239	22	261	11	—
H-ZSM-5(B)-H-10d	93 (± 8)	174	27	201	6	372 (± 17)

Fig. 2. (a) FT-IR spectra of H-ZSM-5(A) and H-ZSM-5(B). (b) Water adsorption isotherm over two zeolite samples. FT-IR spectra have been calibrated based on the sample mass.

Fig. 3. (a) The catalytic activity of ZSM-5 zeolites for the dehydration of cyclohexanol in decalin before and after the hydrothermal treatment as well as steaming treatment. (b) Apparent activation energies (Ea,app) for dehydration of cyclohexanol over ZSM-5 zeolites. (c) Adsorption isotherms of cyclohexanol from decalin over ZSM-5. (d) The proposed reaction path for dehydration of cyclohexanol over ZSM-5 zeolites. Hydrothermal treatment conditions: 0.5 g zeolite, 50 mL H2O, 200 °C, 15 rpm, 5?10 d. Steaming treatment conditions: 0.4 g zeolite, 0.04 mL·min?1 H2O, 20 mL·min?1 N2, 500 °C, 4 h on a fixed bed reactor. Reaction conditions: 0.1 g zeolite, 5 g cyclohexanol, 100 mL decalin, 180 °C, 3 Mpa H2, 4 h in a stirred batch reactor.

Fig. 4. Py-IR spectra on ZSM-5 samples before and after hydrothermal treatment.

Fig. 5. (a) 29Si MAS NMR spectra of ZSM-5 zeolites before and after hydrothermal treatment. (b) The structure diagram of Q4 and Q3 silica species. The fitted 29Si MAS NMR spectra of H-ZSM-5(A) (c) and H-ZSM-5(B) (d) before and after hydrothermal treatment.

Fig. 6. (a) 27Al MAS NMR spectra of ZSM-5 zeolites before and after hydrothermal treatment. (b) The schematic diagrams of different locations of Al. The fitted 27Al MAS NMR spectra (c-d), and the distribution of Al (e) over ZSM-5 zeolites before and after hydrothermal treatment.

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氟离子介导酸性体系合成H-ZSM-5分子筛及其液相环己醇催化转化性能研究

Benefits of H-ZSM-5 zeolite from fluoride-mediated acidic synthesis for liquid-phase conversion of cyclohexanol

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