Fe2O3掺杂NiSO4/Al2O3催化剂中硫酸根迁移增强丙烯选择性三聚

doi:10.1016/S1872-2067(25)64663-8

催化学报 ›› 2025, Vol. 72: 376-391.DOI: 10.1016/S1872-2067(25)64663-8

Fe₂O₃掺杂NiSO₄/Al₂O₃催化剂中硫酸根迁移增强丙烯选择性三聚

刘旭^a, 凌雨^a^,^b, 陈霄^a^,^*(), 梁长海^a^,^*()

^a大连理工大学化工学院, 先进材料与催化工程实验室, 辽宁大连 116024
^b中石化宁波新材料研究院有限公司, 浙江宁波 315207

收稿日期:2024-12-29 接受日期:2025-01-15 出版日期:2025-05-18 发布日期:2025-05-20
通讯作者: *电子信箱: xiaochen@dlut.edu.cn (陈霄),changhai@dlut.edu.cn (梁长海).
基金资助:
国家自然科学基金(22172016);国家自然科学基金(22272014);辽宁省科技计划项目(2023JH1/10400040)

Engineering of sulfate ions migration in Fe₂O₃-doped NiSO₄/Al₂O₃ catalysts to enhance the selective trimerization of propylene

Xu Liu^a, Yu Ling^a^,^b, Xiao Chen^a^,^*(), Changhai Liang^a^,^*()

^aLaboratory of Advanced Materials and Catalytic Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, China
^bSinopec Ningbo New Material Research Institute Co., Ltd., Ningbo 315207, Zhejiang, China

Received:2024-12-29 Accepted:2025-01-15 Online:2025-05-18 Published:2025-05-20
Contact: *E‐mail: changhai@dlut.edu.cn (C. Liang), xiaochen@dlut.edu.cn (X. Chen).
Supported by:
National Natural Science Foundation of China(22172016);National Natural Science Foundation of China(22272014);Science and Technology Plan Project of Liaoning Province(2023JH1/10400040)

摘要/Abstract

摘要：

烯烃齐聚反应在烯烃产业链延伸中扮演着重要角色. 近年来, 随着煤制烯烃、丙烷脱氢和先进裂解技术的快速发展, 丙烯产能持续增长. 在该背景下, 将丙烯转化为高附加值高级烯烃的研究备受关注. 通过烯烃齐聚反应产生的直链、支链高品质烯烃在农业化学品、热塑性树脂和表面活性剂等多个领域得到广泛应用. 然而, 控制产物的碳链长度一直是烯烃齐聚反应中的关键挑战. 自从“镍效应”被发现以来, 负载型镍基多孔材料已成为重要的催化剂. 同时, 钛、铁等多种过渡金属络合物也在催化中发挥着重要作用. 然而, 目前学术界对于这些金属络合物参与的催化反应机制尚未形成统一定论. 因此, 深入探究活性位点状态和潜在反应机制, 实现对产物分布的有效调控, 对该领域的发展至关重要.

本研究以Fe₂O₃掺杂NiSO₄/Al₂O₃催化剂用于丙烯齐聚反应为研究对象. 通过采用分步浸渍法制备了一系列xFe₂O₃-NiSO₄/Al₂O₃催化剂, 创新性地将Fe₂O₃引入NiSO₄/Al₂O₃体系, 旨在提高丙烯的转化效率和三聚体产物的选择性. 通过调节Ni/Fe元素比来控制催化剂性能, 探究烯烃齐聚反应的反应途径. 利用X射线衍射、透射电镜、能量散射谱等多种表征技术深入分析了催化剂的晶体结构、元素分布和微观形貌. 通过H₂-程序升温还原、拉曼光谱、X射线吸收光谱和X射线光电子能谱等手段研究了硫酸根离子迁移行为以及活性物种的化学环境变化. 借助NH₃-程序升温脱附和吸附吡啶-红外光谱分析了催化剂表面的酸性特征. 结果表明, Fe₂O₃的掺杂促进了金属在载体表面的均匀分散, 显著改变了催化剂的孔结构、表面酸性和活性物种的电子状态. 0.25Fe₂O₃-NiSO₄/Al₂O₃ (0.25=n(Fe)/[n(Ni)+n(Fe)])催化剂表现出最佳性能, 其稳态反应速率达48.5 mmolC₃/(g_cat.·h), C9产率约为32.2%, C9 + C12产率约为55.0%, 远高于NiSO₄/Al₂O₃催化剂. 产物分布由Schulz-Flory分布转变为Poisson分布, 有效提高了三聚体和四聚体的选择性. 值得注意的是, 最优的0.25Fe₂O₃-NiSO₄/Al₂O₃催化剂在80 h的稳定性测试中未出现明显失活. 研究还发现, Fe₂O₃的掺杂引发的硫酸根离子迁移对催化剂的性质和反应性能产生重大影响, 改变了Ni和Fe位点的电子缺失程度. 在反应机理方面, 丙烯分子首先与金属氢化物配位插入形成金属烷基中间体, 然后转化为不同聚合度的烯烃. Fe和Ni位点上的丙烯三聚体形成机制存在差异, Ni-C6烷基中间体易发生消除反应生成二聚体, 再聚合形成三聚体; 而Fe-C6烷基中间体更倾向于直接进一步聚合生成三聚体, 导致了不同的反应路径和产物分布.

综上, 本文通过向NiSO₄/Al₂O₃体系掺杂Fe₂O₃, 优化了丙烯齐聚反应催化剂. 在温和条件下提升了反应速率与目标产物收率, 明确了产物分布转变规律, 阐释了反应机理, 为调控丙烯齐聚反应提供新策略, 为高效催化剂的设计及丙烯选择性齐聚工业化应用提供重要参考.

关键词: 丙烯三聚, Fe₂O₃掺杂NiSO₄/Al₂O₃催化剂, 硫酸根离子迁移, Poisson分布, Cossee-Arlman机理

Abstract:

Propylene, a readily accessible and economically viable light olefin, has garnered substantial interest for its potential conversion into valuable higher olefins through oligomerization processes. The distribution of products is profoundly influenced by the catalyst structure. In this study, Fe₂O₃-doped NiSO₄/Al₂O₃ catalysts have been meticulously developed to facilitate the selective trimerization of propylene under mild conditions. Significantly, the 0.25Fe₂O₃-NiSO₄/Al₂O₃ catalyst demonstrates an enhanced reaction rate (48.5 mmol_C3/(g_cat.·h)), alongside a high yield of C9 (~ 32.2%), significantly surpassing the performance of the NiSO₄/Al₂O₃ catalyst (C9: ~24.1%). The incorporation of Fe₂O₃ modifies the migration process of sulfate ions, altering the Lewis acidity of the electron-deficient Ni and Fe sites on the catalyst and resulting a shift in product distribution from a Schulz-Flory distribution to a Poisson distribution. This shift is primarily ascribed to the heightened energy barrier for the β-H elimination reaction in the C6 alkyl intermediates on the doped catalyst, further promoting polymerization to yield a greater quantity of Type II C9. Furthermore, the validation of the Cossee-Arlman mechanism within the reaction pathway has been confirmed. It is noteworthy that the 0.25Fe₂O₃-NiSO₄/Al₂O₃ catalyst exhibits remarkable stability exceeding 80 h in the selective trimerization of propylene. These research findings significantly enhance our understanding of the mechanisms underlying olefin oligomerization reactions and provide invaluable insights for the development of more effective catalysts.

Key words: Propylene trimerization, Fe₂O₃-doped NiSO₄/Al₂O₃ catalyst, Sulfate ions migration, Poisson distribution, Cossee-Arlman mechanism

刘旭, 凌雨, 陈霄, 梁长海. Fe₂O₃掺杂NiSO₄/Al₂O₃催化剂中硫酸根迁移增强丙烯选择性三聚[J]. 催化学报, 2025, 72: 376-391.

Xu Liu, Yu Ling, Xiao Chen, Changhai Liang. Engineering of sulfate ions migration in Fe₂O₃-doped NiSO₄/Al₂O₃ catalysts to enhance the selective trimerization of propylene[J]. Chinese Journal of Catalysis, 2025, 72: 376-391.

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https://www.cjcatal.com/CN/Y2025/V72/I5/376

图/表 16

Scheme 1. Simplified schematic diagram of fixed-bed continuous flow microreactor for propylene oligomerization.

Fig. 1. (a) Scheme for the synthesis route of catalyst with a total metal loading of 10 wt% prepared using a stepwise impregnation method. (b) XRD patterns of xFe2O3-NiSO4/Al2O3 samples and Fe2O3-SO42-/Al2O3 sample. HAADF-STEM image along with the corresponding EDS elemental mappings (c) and line-scanning profiles (d) of 0.5Fe2O3-NiSO4/Al2O3 sample.

Fig. 2. H2-TPR profiles (a) and Raman spectra (b) of xFe2O3-NiSO4/Al2O3 samples sand the referred Fe2O3-SO42-/Al2O3 sample. (c) Schematic diagram of the hypothetical electron transfer in xFe2O3-NiSO4/Al2O3 samples.

Fig. 3. Ni K-edge XANES (a) and k2-weighted Fourier-transformed EXAFS (b) spectra of xFe2O3-NiSO4/Al2O3 samples, compared with Ni foil and NiO (Ni2+) standard references. (c-f) Wavelet transform plots of xFe2O3-NiSO4/Al2O3 samples.

Fig. 4. XPS of Ni 2p (a) and Fe 2p (b) for xFe2O3-NiSO4/Al2O3 samples and the referred Fe2O3-SO42-/Al2O3 sample.

Fig. 5. NH3-TPD curves (a) and Py-FTIR spectra (b) in the desorption temperature at 150 °C for xFe2O3-NiSO4/Al2O3 samples and the referred Fe2O3-SO42-/Al2O3 sample.

Fig. 6. The propylene oligomerization reaction data for xFe2O3-NiSO4/Al2O3 samples, the referred Fe2O3-SO42-/Al2O3 sample, and Al2O3 sample under conditions of T = 70 °C, P = 2.5 MPa, WHSV = 2.1 gC3/(gcat.?h). (a) Propylene consumption rate and conversion versus time on stream. (b) The yield of the target product in the early stage of the reaction and (c) the selectivity of the oligomerized products.

Table 1 Summary of initial conversion and product distribution for the oligomerization of propylene over xFe2O3-NiSO4/Al2O3 samples along with other reference samples (Fe2O3-SO42-/Al2O3 and sulfonic acid resins). (Reaction conditions: 70 °C, 2.5 MPa, 2.1 gC3/(gcat.?h).

Catalysts	NiSO₄/Al₂O₃	0.25Fe₂O₃-NiSO₄/ Al₂O₃	0.5Fe₂O₃-NiSO₄/ Al₂O₃	0.75Fe₂O₃-NiSO₄/ Al₂O₃	Fe₂O₃-SO₄^2-/ Al₂O₃	Sulfonic acid resins
Dimers distributions (%)
1Hex ^Ⅰ	0.7	0.7	0.8	1.2	0.5	n.d.
2Hex ^Ⅰ	32.6	33.8	28.0	25.9	21.5	n.d.
3Hex ^Ⅰ	9.0	9.8	6.8	4.3	5.3	n.d.
4M1P ^Ⅱ	1.6	2.2	3.7	7.2	4.8	2.7
4M2P ^Ⅱ	43.3	46.3	52.8	52.6	43.9	22.8
2M1P ^Ⅱ	1.0	0.4	0.4	0.4	1.0	4.4
2M2P ^Ⅱ	6.8	3.2	3.4	3.2	8.6	30.0
23DM2B ^Ⅱ	4.2	2.2	2.8	3.9	11.1	27.2
3M2P ^Ⅲ	0.8	1.4	1.3	1.3	3.3	12.9
Trimers distributions (%)
4N ^Ⅰ	10.8	0.9	0.4	0.5	0.5	n.d.
2M3O ^Ⅰ	0.9	0.3	0.2	0.1	0.2	n.d.
7M3O ^Ⅰ	4.7	0.6	0.4	0.3	0.3	n.d.
26DM3Hept ^Ⅰ	13.6	6.0	5.3	7.1	7.6	n.d.
23DM2Hept ^Ⅱ	3.4	3.1	2.2	1.5	1.3	2.0
23DM3Hept ^Ⅱ	33.9	48.5	47.8	47.9	47.8	43.6
445TM3Hex ^Ⅱ	2.4	2.6	3.2	3.2	3.3	1.2
4E3Hept ^Ⅱ	16.0	17.6	17.6	18.0	17.8	21.9
344TM2Hex ^Ⅲ	4.4	7.4	7.9	7.5	6.6	10.7
35DM3Hept ^Ⅲ	3.9	8.0	8.7	8.8	9.1	16.4
Others	6.0	5.0	6.3	5.1	5.5	4.2

Fig. 7. (a) Pseudo-first-order kinetic fitting diagram of propylene oligomerization. Propylene conversion (b,c) and C9 distribution selectivity (d,e) as a function of contact time on NiSO4/Al2O3 sample and 0.25 Fe2O3-NiSO4/Al2O3 sample. Reaction conditions: 70 °C, 2.5 MPa.

Fig. 8. 2D HSQC spectra (a,b) and 1H-NMR spectra (c,d) of products that obtained from the oligomerization of propylene over the 0.25 Fe2O3-NiSO4/Al2O3 sample at contact time of 5 gcat./(gC3·min) and 30 gcat./(gC3·min), respectively. (e) GC×GC-MS spectrum of the product that obtained from the oligomerization of propylene over the 0.25 Fe2O3-NiSO4/Al2O3 sample at a contact time of 5 gcat./(gC3·min). (Reaction conditions: 70 °C, 2.5 MPa).

Scheme 2. Propylene oligomerization reaction network according to the Cossee-Arlman mechanism.

Fig. 9. (a) Relationship between the consumption rate of propylene and Lewis acid concentration (CL). (b) Relationship between the induction period of the reaction and the binding energy of Ni species. Influence of Fe species on the distribution of oligomerization products (c) and C3H6-TPSR-MS profiles (m/z = 84) (d) of xFe2O3-NiSO4/Al2O3 samples.

Fig. 10. (a) Reaction paths of dimer formation at metal sites based on Cossee-Arlman mechanism. (b) Two routes for propylene oligomerization leading to trimer products. (c) Type I C9 produced by propylene oligomerization through Route I.

Fig. 11. Results of stability testing for the 0.25Fe2O3-NiSO4/Al2O3 sample at 70 °C, 2.5 MPa, and 2.1 gC3/(gcat.·h).

Fig. 12. TG-MS curves of the fresh (a,b) and spent (c,d) 0.25Fe2O3-NiSO4/Al2O3 sample.

Fig. 13. XPS spectra of Ni 2p (a) and Fe 2p (b) for the fresh and spent 0.25Fe2O3-NiSO4/Al2O3 sample.

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Fe₂O₃掺杂NiSO₄/Al₂O₃催化剂中硫酸根迁移增强丙烯选择性三聚

Engineering of sulfate ions migration in Fe₂O₃-doped NiSO₄/Al₂O₃ catalysts to enhance the selective trimerization of propylene

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