Mo改性Pd/NaY催化剂用于甲醇间接氧化羰基化合成碳酸二甲酯

doi:10.1016/S1872-2067(24)60019-7

催化学报 ›› 2024, Vol. 60: 327-336.DOI: 10.1016/S1872-2067(24)60019-7

Mo改性Pd/NaY催化剂用于甲醇间接氧化羰基化合成碳酸二甲酯

黄恪^a, 袁世诚^a, 梅荣艳^a, 杨歌^b, 白鹏^a, 郭海玲^a, 王纯正^a^,^*(), Svetlana Mintova^a^,^c^,^*()

^a中国石油大学(华东), 化学化工学院, 重质油全国重点实验室, 山东青岛 266580, 中国
^b青岛科技大学化工学院, 先进陶瓷与机械加工技术教育部重点实验室, 山东青岛 266042, 中国
^c法国国家科学研究中心, 催化与光谱实验室, 卡昂, 法国

收稿日期:2024-03-07 接受日期:2024-03-20 出版日期:2024-05-18 发布日期:2024-05-23
通讯作者: *电子信箱: czwang@upc.edu.cn (C. Wang), svetlana.mintova@ensicaen.fr (S. Mintova).
基金资助:
国家重点研发计划(2022YFE0116000);国家重点研发计划(2022YFA1503400);国家自然科学基金(42072147);国家自然科学基金(21908246);国家自然科学基金(21975285);国家自然科学基金(22175200);山东省重点研发计划(重大科技创新项目)(2021ZLGX06);中法国际研究网络(IRN)“Zeolites”

Mo-promoted Pd/NaY catalyst for indirect oxidative carbonylation of methanol to dimethyl carbonate

Ke Huang^a, Shicheng Yuan^a, Rongyan Mei^a, Ge Yang^b, Peng Bai^a, Hailing Guo^a, Chunzheng Wang^a^,^*(), Svetlana Mintova^a^,^c^,^*()

^aState Key Laboratory of Heavy Oil Processing, College of Chemistry and Chemical Engineering, China University of Petroleum (East China), Qingdao 266580, Shandong, China
^bCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, Shandong, China
^cLaboratoire Catalyse et Spectrochimie (LCS), Normandie Université, ENSICAEN, UNICAEN, CNRS, 6 boulevard Maréchal Juin, Caen 14050, France

Received:2024-03-07 Accepted:2024-03-20 Online:2024-05-18 Published:2024-05-23
Contact: *E-mail: czwang@upc.edu.cn (C. Wang), svetlana.mintova@ensicaen.fr (S. Mintova).
Supported by:
National Key R&D Program of China(2022YFE0116000);National Key R&D Program of China(2022YFA1503400);National Natural Science Foundation of China(42072147);National Natural Science Foundation of China(21908246);National Natural Science Foundation of China(21975285);National Natural Science Foundation of China(22175200);Key Research and Development Program (Major Scientific and Technological Innovation Project) of Shandong Province(2021ZLGX06);Sino-French International Research Network (IRN) “Zeolites”

摘要/Abstract

摘要：

碳酸二甲酯(DMC)因具有较好的溶解性、生物降解性和低毒性, 而被认为是一种绿色化学品. 其用途广泛, 不仅用于合成聚碳酸酯, 还是锂离子电池电解液、燃料添加剂以及羰基化和甲基化反应的重要试剂. 在众多合成方法中, CH₃OH间接氧化羰基化合成DMC, 具有无爆炸风险、反应条件温和以及原子经济性高等优点, 因而展现出广阔的应用前景. 然而, 这一过程中使用的无氯Pd/NaY催化剂存在以下问题: Pd²⁺活性物种容易被反应物CO还原成Pd⁰物种, 导致Pd烧结和催化剂失活. 因此, 如何在催化过程中保持Pd²⁺物种的稳定, 是当前面临的一个重要挑战.

本文采用“自上而下”的方法, 制备了Mo改性的Pd/NaY催化剂(Pd-Mo/NaY). 该催化剂在保持贵金属Pd氧化态的同时, 增强了对反应物CO的吸附能力, 进而提高了催化剂的稳定性. 在CH₃OH间接氧化羰基化制DMC反应中, Pd-Mo/NaY表现出比Pd/NaY催化剂更高的催化活性和稳定性. 在30 h的反应过程中, Pd-Mo/NaY催化剂上的CO转化率稳定维持在约97%, 而Pd/NaY催化剂上的CO转化率则从94%逐渐下降至70%. 此外, Pd-Mo/NaY催化剂的本征活性(TOF)为0.019 s^-1, 也明显高于Pd/NaY催化剂的0.005 s^-1. X射线衍射、物理吸附和扫描电镜结果表明, Mo改性未显著改变Pd/NaY的物相结构、孔结构性质与微观形貌. 透射电镜与扫描电镜能谱结果表明, 两个催化剂的Pd聚集状态存在显著差异. Pd/NaY催化剂中Pd物种发生了明显聚集, Pd颗粒平均尺寸达到10.2 nm; 而Pd-Mo/NaY催化剂中, 大部分Pd物种仍保持高度分散的状态, 仅有少量聚集的Pd颗粒, 其平均尺寸仅为2.3 nm.

通过羟基红外、吡啶红外与氨气程序升温脱附表征技术进一步研究了催化性能与Pd聚集状态差异的原因. 结果表明, Mo的引入有效减少了因Pd离子交换过程引入的桥式羟基, 从而降低了Pd-Mo/NaY催化剂的酸性. 此外, 氢气程序升温还原与X射线光电子能谱结果进一步揭示, Pd与Mo之间的相互作用调变了Pd-Mo/NaY的活性位结构, 阻碍了活性Pd²⁺物种被反应物CO还原为Pd⁰物种, 从而有效缓解了Pd物种的聚集. CO漫反射红外与CO低温透射红外研究则表明, Pd-Mo之间的相互作用以及Pd²⁺活性位点的增加, 显著增强了催化剂对反应物CO的吸附能力. 通过原位漫反射红外(DRIFTS)实验捕获了COOCH₃*关键反应中间体, 并发现无论是Pd/NaY催化剂还是Mo改性的Pd-Mo/NaY催化剂, 均遵循相似的反应路径, 并具有相同的决速步骤.

综上, 本文通过Mo对Pd/NaY催化剂进行改性, 有效抑制了反应过程中贵金属Pd的烧结, 从而显著提高Pd-Mo/NaY催化剂的稳定性. 通过这一改性方法, 实现了活性Pd²⁺物种的高度稳定, 为甲醇间接氧化羰基化制DMC催化剂的研发提供了新思路.

关键词: 分子筛, NaY, 钯, 羰基化, 碳酸二甲酯

Abstract:

A chlorine-free catalyst consisting of zeolite Y modified with Pd (Pd/NaY) catalyst has been prepared and used in the indirect oxidative carbonylation of methanol to dimethyl carbonate (DMC). The activity and stability of the catalyst were further improved by introducing molybdenum into Pd/NaY using a top-down approach (Pd-Mo/NaY catalyst). The Pd-Mo/NaY catalyst exhibited higher stability compared to the Pd/NaY. A high CO conversion of 97% and DMC selectivity of 80% during a 30-hour catalytic test for the Pd-Mo/NaY were obtained. Furthermore, the incorporation of Mo was found to partially heal the silanols and hinder the aggregation of Pd in the Pd-Mo/NaY catalyst. The interactions between Mo and Pd increased the amount of active Pd²⁺ species and enhanced the adsorption of CO reactant on the Pd-Mo/NaY catalyst. The key reaction intermediate of COOCH₃* was captured by in situ diffuse reflectance infrared Fourier transform spectroscopy. The stabilization of active Pd²⁺ species contributed to the enhanced catalytic activity of the Pd-Mo/NaY catalyst in the indirect oxidative carbonylation of methanol to DMC reaction.

Key words: Zeolite, NaY, Palladium, Carbonylation, Dimethyl carbonate

黄恪, 袁世诚, 梅荣艳, 杨歌, 白鹏, 郭海玲, 王纯正, Svetlana Mintova. Mo改性Pd/NaY催化剂用于甲醇间接氧化羰基化合成碳酸二甲酯[J]. 催化学报, 2024, 60: 327-336.

Ke Huang, Shicheng Yuan, Rongyan Mei, Ge Yang, Peng Bai, Hailing Guo, Chunzheng Wang, Svetlana Mintova. Mo-promoted Pd/NaY catalyst for indirect oxidative carbonylation of methanol to dimethyl carbonate[J]. Chinese Journal of Catalysis, 2024, 60: 327-336.

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Fig. 1. Conversion of CO and CH3ONO, selectivity of DMC, dimethoxymethane (DMM) and methyl formate (MF) over the catalysts Pd/NaY (A) and Pd-Mo/NaY (B) as a function of time on stream in the gas-solid phase indirect oxidation of methanol to DMC. Reaction conditions: 0.100 g catalyst, CO/CH3ONO/N2 = 1/6/33 (volume), GHSV = 8000 mL gcat.?1 h?1, 110 °C, 0.1 MPa.

Fig. 2. Effect of the CO/CH3ONO ratio on the CH3ONO conversion and DMC selectivity over the Pd-Mo/NaY catalyst in the gas-solid phase indirect oxidation of methanol to DMC. Reaction conditions: 0.100 g catalyst, CO/CH3ONO/N2 = 1, 1.2, 1.5, 2, 3/6/33 (volume), GHSV = 8000-12000 mL gcat.?1 h?1, 110 °C, 0.1 MPa.

Table 1 Physicochemical properties and catalytic performance of the Pd/NaY and Pd-Mo/NaY catalysts.

Catalyst	Status	S_BET^a (m² g⁻¹)	V_mic^a (cm³ g⁻¹)	TOF (s⁻¹)^b	E_a^c (kJ mol⁻¹)
Pd/NaY	fresh	887	0.33	0.005	72
Pd/NaY	after 30 h test	863	0.32	-	-
Pd-Mo/NaY	fresh	857	0.32	0.019	87
Pd-Mo/NaY	after 30 h test	794	0.30	-	-

Fig. 3. Arrhenius plot for the DMC synthesis on the Pd/NaY and Pd-Mo/NaY catalysts (Ea, apparent activation energy). Reaction conditions: mixture of 0.010 g catalyst and 0.090 g α-Al2O3 (diluent), CO/CH3ONO/N2 = 1/6/33 (volume), GHSV = 80,000 mL gcat.?1 h?1, 0.1 MPa.

Fig. 4. XRD patterns in the range of 3°-50°(A) and enlarged patterns (B) in the range of 30°-45°: fresh Pd/NaY (a), Pd/NaY after 30 h catalytic test (b), fresh Pd-Mo/NaY (c), Pd-Mo/NaY after 30 h catalytic test (d), and NaY zeolite (e).

Fig. 5. TEM images of used catalysts after 30 h catalytic test: Pd/NaY (a1,a2) and Pd-Mo/NaY (b1,b2). Insets: particle size distribution of Pd nanoparticles in samples Pd/NaY (a1) and Pd-Mo/NaY (b1) determined by measuring of about 200 nanoparticles.

Fig. 6. SEM images and EDS elemental mapping of Pd/NaY (a) and Pd-Mo/NaY (b) used catalysts after 30 h catalytic test.

Fig. 7. FT-IR spectra of NaY (a), Pd/NaY (b), Mo/NaY (c) and Pd-Mo/NaY (d) samples in the OH stretching vibration region (3400-3800 cm?1).

Fig. 8. FT-IR spectra of CO adsorbed at -140 °C on NaY (A), Mo/NaY (B), Pd/NaY (D) and Pd-Mo/NaY (E) samples. (C) The band areas at 2167 cm-1 versus the CO partial pressure. (F) The band areas at 2169 cm-1 versus the CO partial pressure. The spectra were collected at the equilibrium CO partial pressure of 132 Pa (a) -385 Pa (g).

Fig. 9. DRIFTS spectra of CO adsorbed on used Pd/NaY catalysts after 2 h (a) and 6 h (b) catalytic test, and on used Pd-Mo/NaY catalysts after 2 h (c) and 6 h (d) catalytic test recorded at 35 °C.

Fig. 10. H2-TPR profiles of fresh Pd/NaY (a) and Pd-Mo/NaY (b) catalysts.

Fig. 11. XPS spectra of Pd 3d (A) and Mo 3d (B) regions of used Pd/NaY (a) and Pd-Mo/NaY (b) catalysts.

Table 2 The peak areas of Pd0, Pd2+, and Pd2+/Pd0 area ratio of the used catalysts Pd/NaY and Pd-Mo/NaY determined by XPS a.

Catalyst	Area of Pd⁰		Area of Pd²⁺		Pd^2/Pd⁰ ratio
Pd/NaY	1367^a	1640^a		1.2
Pd-Mo/NaY	1524^a	2437^a		1.6

Fig. 12. In situ DRIFTS spectra of CO and CH3ONO reactants on Pd/NaY (A) and Pd-Mo/NaY (B) catalysts, and the corresponding surface species on the Pd/NaY (C) and Pd-Mo/NaY (D) catalysts after parching with N2 recorded at different temperatures: 30, 50, 70, 90, 110 and 125 °C.

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Mo改性Pd/NaY催化剂用于甲醇间接氧化羰基化合成碳酸二甲酯

Mo-promoted Pd/NaY catalyst for indirect oxidative carbonylation of methanol to dimethyl carbonate

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