Mechanism of dibenzofuran hydrodeoxygenation on the Ni (1 1 1) surface

doi:10.1016/j.cjche.2021.02.005

中国化学工程学报 ›› 2021, Vol. 35 ›› Issue (7): 204-210.DOI: 10.1016/j.cjche.2021.02.005

• Catalysis, Kinetics and Reaction Engineering • 上一篇下一篇

Mechanism of dibenzofuran hydrodeoxygenation on the Ni (1 1 1) surface

Zi-Zheng Xie, Meng Zhang, Xing-Bao Wang, Liang Guo, Zhen-Yi Du, Wen-Ying Li

State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology, Taiyuan 030024, China;Key Laboratory of Coal Science and Technology (Taiyuan University of Technology), Ministry of Education, Taiyuan 030024, China

收稿日期:2020-10-13 修回日期:2021-02-17 出版日期:2021-07-28 发布日期:2021-09-30
通讯作者: Xing-Bao Wang, Wen-Ying Li
基金资助:
The authors gratefully acknowledge financial support from the National Key Research and Development Program of China (2016YFB0600305) and National Natural Science Foundation of China (21808153, 22078220).

Mechanism of dibenzofuran hydrodeoxygenation on the Ni (1 1 1) surface

Zi-Zheng Xie, Meng Zhang, Xing-Bao Wang, Liang Guo, Zhen-Yi Du, Wen-Ying Li

State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology, Taiyuan 030024, China;Key Laboratory of Coal Science and Technology (Taiyuan University of Technology), Ministry of Education, Taiyuan 030024, China

Received:2020-10-13 Revised:2021-02-17 Online:2021-07-28 Published:2021-09-30
Contact: Xing-Bao Wang, Wen-Ying Li
Supported by:
The authors gratefully acknowledge financial support from the National Key Research and Development Program of China (2016YFB0600305) and National Natural Science Foundation of China (21808153, 22078220).

摘要/Abstract

摘要： The low-temperature coal tar contains a considerable number of oxygen-containing compounds, which results in poor quality. The catalytic hydrodeoxygenation of oxygen-containing compound to an added-value chemical compound is one of the most efficient methods to upgrade coal tar. In this study, density functional theory calculations are employed to assess and analyze in detail the hydrodeoxygenation of dibenzofuran, as a model compound of coal tar, on the Ni (1 1 1) surface. The obtained results indicate that dibenzofuran can be firstly hydrogenated to tetrahydrodibenzofuran and hexahydrodibenzofuran. The five-membered-ring opening reaction of tetrahydrodibenzofuran is more straightforward than that of hexahydrodibenzofuran (E_a=0.71 eV vs. 1.66 eV). Then, both pathways generate an intermediate 2-cyclohexylphenoxy compound. One part of 2-cyclohexylphenoxy is hydrogenated to 2-cyclohexylphenol and consecutively hydrogenated to cyclohexylcyclohexanol, and another part is directly hydrogenated to cyclohexylcyclohexanone. The hydrogenated intermediates of 2-cyclohexylphenol have higher deoxygenation barriers than 2-cyclohexylphenol and cyclohexylcyclohexanol. During the hydrogenation process of cyclohexylcyclohexanone to cyclohexylcyclohexanol, the intermediate 26, formed by adding H to O atom of cyclohexylcyclohexanone, exhibits the lowest deoxygenation barrier of 1.08 eV. High hydrogen coverage may promote the hydrogenation of tetrahydrodibenzofuran, hexahydrodibenzofuran, and intermediate 26 to generate dodecahydrodibenzofuran and cyclohexylcyclohexanol. This dibenzofuran hydrodeoxygenation reaction mechanism corroborates well with previous experimental results and provides a theoretical basis for further optimization of the design of nickel-based catalysts.

关键词: Oxygen-containing compound, Hydrogenation, Deoxygenation, Catalysis, Computational chemistry

Abstract: The low-temperature coal tar contains a considerable number of oxygen-containing compounds, which results in poor quality. The catalytic hydrodeoxygenation of oxygen-containing compound to an added-value chemical compound is one of the most efficient methods to upgrade coal tar. In this study, density functional theory calculations are employed to assess and analyze in detail the hydrodeoxygenation of dibenzofuran, as a model compound of coal tar, on the Ni (1 1 1) surface. The obtained results indicate that dibenzofuran can be firstly hydrogenated to tetrahydrodibenzofuran and hexahydrodibenzofuran. The five-membered-ring opening reaction of tetrahydrodibenzofuran is more straightforward than that of hexahydrodibenzofuran (E_a=0.71 eV vs. 1.66 eV). Then, both pathways generate an intermediate 2-cyclohexylphenoxy compound. One part of 2-cyclohexylphenoxy is hydrogenated to 2-cyclohexylphenol and consecutively hydrogenated to cyclohexylcyclohexanol, and another part is directly hydrogenated to cyclohexylcyclohexanone. The hydrogenated intermediates of 2-cyclohexylphenol have higher deoxygenation barriers than 2-cyclohexylphenol and cyclohexylcyclohexanol. During the hydrogenation process of cyclohexylcyclohexanone to cyclohexylcyclohexanol, the intermediate 26, formed by adding H to O atom of cyclohexylcyclohexanone, exhibits the lowest deoxygenation barrier of 1.08 eV. High hydrogen coverage may promote the hydrogenation of tetrahydrodibenzofuran, hexahydrodibenzofuran, and intermediate 26 to generate dodecahydrodibenzofuran and cyclohexylcyclohexanol. This dibenzofuran hydrodeoxygenation reaction mechanism corroborates well with previous experimental results and provides a theoretical basis for further optimization of the design of nickel-based catalysts.

Key words: Oxygen-containing compound, Hydrogenation, Deoxygenation, Catalysis, Computational chemistry

Zi-Zheng Xie, Meng Zhang, Xing-Bao Wang, Liang Guo, Zhen-Yi Du, Wen-Ying Li. Mechanism of dibenzofuran hydrodeoxygenation on the Ni (1 1 1) surface[J]. 中国化学工程学报, 2021, 35(7): 204-210.

Zi-Zheng Xie, Meng Zhang, Xing-Bao Wang, Liang Guo, Zhen-Yi Du, Wen-Ying Li. Mechanism of dibenzofuran hydrodeoxygenation on the Ni (1 1 1) surface[J]. Chinese Journal of Chemical Engineering, 2021, 35(7): 204-210.

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Mechanism of dibenzofuran hydrodeoxygenation on the Ni (1 1 1) surface

Mechanism of dibenzofuran hydrodeoxygenation on the Ni (1 1 1) surface

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