Tandem hydroalkylation and deoxygenation of lignin-derived phenolics to synthesize high-density fuels

doi:10.1016/j.cjche.2023.10.011

中国化学工程学报 ›› 2024, Vol. 66 ›› Issue (2): 104-109.DOI: 10.1016/j.cjche.2023.10.011

• Full Length Article • 上一篇下一篇

Tandem hydroalkylation and deoxygenation of lignin-derived phenolics to synthesize high-density fuels

Rui Yu^1,2, Zhensheng Shen^1,2, Yanan Liu^1,2, Chengxiang Shi^1,2, Juncong Qu^1,2, Lun Pan^1,2,3, Zhenfeng Huang^1,2, Xiangwen Zhang^1,2,3, Ji-Jun Zou^1,2,3

1. Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2. Collaborative Innovative Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China;
3. Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China

收稿日期:2023-07-21 修回日期:2023-10-21 出版日期:2024-02-28 发布日期:2024-04-20
通讯作者: Chengxiang Shi,E-mail:cxshi@tju.edu.cn;Ji-Jun Zou,E-mail:jj_zou@tju.edu.cn
基金资助:
The authors appreciate the support from National Key Research and Development Program of China (2021YFC2104400), the Tianjin Science and Technology Plan Project (21JCQNJC00340), and the Haihe Laboratory of Sustainable Chemical Transformations for financial support.

Tandem hydroalkylation and deoxygenation of lignin-derived phenolics to synthesize high-density fuels

Rui Yu^1,2, Zhensheng Shen^1,2, Yanan Liu^1,2, Chengxiang Shi^1,2, Juncong Qu^1,2, Lun Pan^1,2,3, Zhenfeng Huang^1,2, Xiangwen Zhang^1,2,3, Ji-Jun Zou^1,2,3

1. Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2. Collaborative Innovative Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China;
3. Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China

Received:2023-07-21 Revised:2023-10-21 Online:2024-02-28 Published:2024-04-20
Contact: Chengxiang Shi,E-mail:cxshi@tju.edu.cn;Ji-Jun Zou,E-mail:jj_zou@tju.edu.cn
Supported by:
The authors appreciate the support from National Key Research and Development Program of China (2021YFC2104400), the Tianjin Science and Technology Plan Project (21JCQNJC00340), and the Haihe Laboratory of Sustainable Chemical Transformations for financial support.

摘要/Abstract

摘要： Lignin is the most abundant naturally phenolic biomass, and the synthesis of high-performance renewable fuel from lignin has attracted significant attention. We propose the efficient synthesis of high-density fuels using simulated lignin cracked oil in tandem with hydroalkylation and deoxygenation reactions. First, we investigated the reaction pathway for the hydroalkylation of phenol, which competes with the hydrodeoxygenation form cyclohexane. And then, we investigated the effects of metal catalyst types, the loading amount of metallic, acid dosage, and reactant ratio on the reaction results. The phenol hydroalkylation and hydrodeoxygenation were balanced when 180°C and 5MPa H₂ with the alkanes yield of 95%. By extending the substrate to other lignin-derived phenolics and simulated lignin cracked oil, we obtained the polycyclic alkane fuel with high density of 0.918g·ml^-1 and calorific value of 41.2MJ·L^-1. Besides, the fuel has good low-temperature properties (viscosity of 9.3mm²·s^-1at 20°C and freezing point below-55°C), which is expected to be used as jet fuel. This work provides a promising way for the easy and green production of high-density fuel directly from real lignin oil.

关键词: High-density fuel, Biofuel, Hydrogenation, Alkylation, Lignin, Phenolics

Abstract: Lignin is the most abundant naturally phenolic biomass, and the synthesis of high-performance renewable fuel from lignin has attracted significant attention. We propose the efficient synthesis of high-density fuels using simulated lignin cracked oil in tandem with hydroalkylation and deoxygenation reactions. First, we investigated the reaction pathway for the hydroalkylation of phenol, which competes with the hydrodeoxygenation form cyclohexane. And then, we investigated the effects of metal catalyst types, the loading amount of metallic, acid dosage, and reactant ratio on the reaction results. The phenol hydroalkylation and hydrodeoxygenation were balanced when 180°C and 5MPa H₂ with the alkanes yield of 95%. By extending the substrate to other lignin-derived phenolics and simulated lignin cracked oil, we obtained the polycyclic alkane fuel with high density of 0.918g·ml^-1 and calorific value of 41.2MJ·L^-1. Besides, the fuel has good low-temperature properties (viscosity of 9.3mm²·s^-1at 20°C and freezing point below-55°C), which is expected to be used as jet fuel. This work provides a promising way for the easy and green production of high-density fuel directly from real lignin oil.

Key words: High-density fuel, Biofuel, Hydrogenation, Alkylation, Lignin, Phenolics

Rui Yu, Zhensheng Shen, Yanan Liu, Chengxiang Shi, Juncong Qu, Lun Pan, Zhenfeng Huang, Xiangwen Zhang, Ji-Jun Zou. Tandem hydroalkylation and deoxygenation of lignin-derived phenolics to synthesize high-density fuels[J]. 中国化学工程学报, 2024, 66(2): 104-109.

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Tandem hydroalkylation and deoxygenation of lignin-derived phenolics to synthesize high-density fuels

Tandem hydroalkylation and deoxygenation of lignin-derived phenolics to synthesize high-density fuels

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