Catalytic cascade acetylation-alkylation of biofuran to C17 diesel precursor enabled by a budget acid-switchable catalyst

doi:10.1016/j.cjche.2020.09.037

Chinese Journal of Chemical Engineering ›› 2021, Vol. 34 ›› Issue (6): 171-179.DOI: 10.1016/j.cjche.2020.09.037

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Catalytic cascade acetylation-alkylation of biofuran to C₁₇ diesel precursor enabled by a budget acid-switchable catalyst

Chuanhui Li, Yuanzhong Li, Xiaoxiang Luo, Zhengyi Li, Heng Zhang, Hu Li, Song Yang

State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R & D of Fine Chemicals, Guizhou University, Guiyang 550025, China

Received:2020-08-21 Revised:2020-09-24 Online:2021-08-30 Published:2021-06-28
Contact: Hu Li, Song Yang
Supported by:
The authors thank the financial support from the National Natural Science Foundation of China (21666008, 21908033, 21576059), Fok Ying-Tong Education Foundation (161030), Guizhou Science & Technology Foundation ([2018]1037), and Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023).

Catalytic cascade acetylation-alkylation of biofuran to C₁₇ diesel precursor enabled by a budget acid-switchable catalyst

Chuanhui Li, Yuanzhong Li, Xiaoxiang Luo, Zhengyi Li, Heng Zhang, Hu Li, Song Yang

State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R & D of Fine Chemicals, Guizhou University, Guiyang 550025, China

通讯作者: Hu Li, Song Yang
基金资助:
The authors thank the financial support from the National Natural Science Foundation of China (21666008, 21908033, 21576059), Fok Ying-Tong Education Foundation (161030), Guizhou Science & Technology Foundation ([2018]1037), and Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023).

Abstract

Abstract: Lignocellulosic biomass is a promising feedstock for the synthesis of value-added chemicals and biofuels. However, one of the biggest challenges for producing high-quality diesel fuels is the lack of sufficient carbon-chain length in biomass derivatives. In this study, a C17 diesel precursor 1,1,1-tris(5-methyl-2-f uryl)ethane (TEMF) with a yield of ca. 70% was synthesized from the cascade acetylation-hydroxyalkyla tion/alkylation of bio-based 2-methylfuran (MF) with acetic anhydride (AA) catalyzed by acid-treated montmorillonite with enhanced acidity and improved porosity. The catalytic mechanism of the cascade reaction process was investigated over different types of acid species (Brønsted acid and Lewis acid), and the influence of in situ formed acetic acid was also examined. A synergistic effect was observed to enable the synthesis of TEMF from the trimerization of MF with AA, in which Lewis acid and weak Brønsted acid species mainly catalyze the acetylation and hydroxyalkylation processes, while the subsequent alkylation step is mainly catalyzed by strong Brønsted acid.

Key words: Biomass, Diesel, Catalysis, Biofuranic compound, Acetylation-alkylation

摘要： Lignocellulosic biomass is a promising feedstock for the synthesis of value-added chemicals and biofuels. However, one of the biggest challenges for producing high-quality diesel fuels is the lack of sufficient carbon-chain length in biomass derivatives. In this study, a C17 diesel precursor 1,1,1-tris(5-methyl-2-f uryl)ethane (TEMF) with a yield of ca. 70% was synthesized from the cascade acetylation-hydroxyalkyla tion/alkylation of bio-based 2-methylfuran (MF) with acetic anhydride (AA) catalyzed by acid-treated montmorillonite with enhanced acidity and improved porosity. The catalytic mechanism of the cascade reaction process was investigated over different types of acid species (Brønsted acid and Lewis acid), and the influence of in situ formed acetic acid was also examined. A synergistic effect was observed to enable the synthesis of TEMF from the trimerization of MF with AA, in which Lewis acid and weak Brønsted acid species mainly catalyze the acetylation and hydroxyalkylation processes, while the subsequent alkylation step is mainly catalyzed by strong Brønsted acid.

关键词: Biomass, Diesel, Catalysis, Biofuranic compound, Acetylation-alkylation

Chuanhui Li, Yuanzhong Li, Xiaoxiang Luo, Zhengyi Li, Heng Zhang, Hu Li, Song Yang. Catalytic cascade acetylation-alkylation of biofuran to C₁₇ diesel precursor enabled by a budget acid-switchable catalyst[J]. Chinese Journal of Chemical Engineering, 2021, 34(6): 171-179.

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Catalytic cascade acetylation-alkylation of biofuran to C₁₇ diesel precursor enabled by a budget acid-switchable catalyst

Catalytic cascade acetylation-alkylation of biofuran to C₁₇ diesel precursor enabled by a budget acid-switchable catalyst

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