Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts

doi:10.1016/j.cjche.2021.12.026

中国化学工程学报 ›› 2023, Vol. 53 ›› Issue (1): 310-316.DOI: 10.1016/j.cjche.2021.12.026

• Full Length Article • 上一篇下一篇

Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts

Xuan Gao¹, Zhihui Li^1,2, Dongsheng Zhang¹, Xinqiang Zhao¹, Yanji Wang¹

1. Hebei Provincial Key Lab of Green Chemical Technology and High Efficient Energy Saving, Hebei University of Technology, Tianjin 300130, China;
2. School of Energy and Environmental Engineering, Hebei University of Technology, Tianjin 300130, China

收稿日期:2021-07-26 修回日期:2021-11-17 出版日期:2023-01-28 发布日期:2023-04-08
通讯作者: Zhihui Li,E-mail:lizhihui425@hebut.edu.cn;Yanji Wang,E-mail:yjwang@hebut.edu.cn
基金资助:
This work was conducted with financial support from the National Natural Science Foundation of China (Nos. U20A20152, 21236001 and 21878069).

Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts

Xuan Gao¹, Zhihui Li^1,2, Dongsheng Zhang¹, Xinqiang Zhao¹, Yanji Wang¹

1. Hebei Provincial Key Lab of Green Chemical Technology and High Efficient Energy Saving, Hebei University of Technology, Tianjin 300130, China;
2. School of Energy and Environmental Engineering, Hebei University of Technology, Tianjin 300130, China

Received:2021-07-26 Revised:2021-11-17 Online:2023-01-28 Published:2023-04-08
Contact: Zhihui Li,E-mail:lizhihui425@hebut.edu.cn;Yanji Wang,E-mail:yjwang@hebut.edu.cn
Supported by:
This work was conducted with financial support from the National Natural Science Foundation of China (Nos. U20A20152, 21236001 and 21878069).

摘要/Abstract

摘要： 2,5-Dicyanofuran (DCF) is an important biomass-derived platform compound primarily used to prepare bio-based adiponitrile, which is the key precursor for the synthesis of nylon 66 and 1,6-hexanediisocyanate (HDI). In this study, one-pot, green and safe synthesis of DCF from 2,5-diformylfuran (DFF) and hydroxylamine ionic liquid salts was proposed. Eco-friendly hydroxylamine ionic liquid salts were used as the nitrogen source. Ionic liquid exhibited three-fold function of cosolvent, catalysis and phase separation. The conversion of DFF and yield of DCF reached 100% under the following optimum reaction conditions: temperature of 120 ℃ for 70 min, volume ratio of paraxylene: [HSO₃-b-Py]·HSO₄ of 2:1, and molar ratio of DFF:(NH₂OH)₂·[HSO₃-b-Py]·HSO₄ of 1:1.5. The reaction mechanism for the synthesis of DCF was proposed, and the kinetic model was established. The reaction order with respect to DFF and intermediate product 2,5-diformylfuran dioxime (DFFD) was 1.06 and 0.16, and the reaction activation energy was 64.07 kJ·mol^-1 and 59.37 kJ·mol^-1 respectively. After the reaction, the ionic liquid was easy to separate, recover and recycle.

关键词: 2,5-Dicyanofuran, Hydroxylamine ionic liquid salts, Green synthesis, Kinetics

Abstract: 2,5-Dicyanofuran (DCF) is an important biomass-derived platform compound primarily used to prepare bio-based adiponitrile, which is the key precursor for the synthesis of nylon 66 and 1,6-hexanediisocyanate (HDI). In this study, one-pot, green and safe synthesis of DCF from 2,5-diformylfuran (DFF) and hydroxylamine ionic liquid salts was proposed. Eco-friendly hydroxylamine ionic liquid salts were used as the nitrogen source. Ionic liquid exhibited three-fold function of cosolvent, catalysis and phase separation. The conversion of DFF and yield of DCF reached 100% under the following optimum reaction conditions: temperature of 120 ℃ for 70 min, volume ratio of paraxylene: [HSO₃-b-Py]·HSO₄ of 2:1, and molar ratio of DFF:(NH₂OH)₂·[HSO₃-b-Py]·HSO₄ of 1:1.5. The reaction mechanism for the synthesis of DCF was proposed, and the kinetic model was established. The reaction order with respect to DFF and intermediate product 2,5-diformylfuran dioxime (DFFD) was 1.06 and 0.16, and the reaction activation energy was 64.07 kJ·mol^-1 and 59.37 kJ·mol^-1 respectively. After the reaction, the ionic liquid was easy to separate, recover and recycle.

Key words: 2,5-Dicyanofuran, Hydroxylamine ionic liquid salts, Green synthesis, Kinetics

Xuan Gao, Zhihui Li, Dongsheng Zhang, Xinqiang Zhao, Yanji Wang. Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts[J]. 中国化学工程学报, 2023, 53(1): 310-316.

Xuan Gao, Zhihui Li, Dongsheng Zhang, Xinqiang Zhao, Yanji Wang. Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts[J]. Chinese Journal of Chemical Engineering, 2023, 53(1): 310-316.

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Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts

Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts

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