Heterogeneous synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and methyl carbonate in methanol over a CeO2 catalyst

doi:10.1016/j.cjche.2014.03.002

›› 2015, Vol. 23 ›› Issue (2): 446-450.DOI: 10.1016/j.cjche.2014.03.002

• RESEARCH NOTES • Previous Articles Next Articles

Heterogeneous synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and methyl carbonate in methanol over a CeO₂ catalyst

Yan Cao, Huiquan Li, Xintao Li, Liguo Wang, Ganyu Zhu, Qing Tang

Key Laboratory of Green Process and Engineering, National Engineering Laboratory for Hydrometallurgical Cleaner Production Technology, Institute of Process Engineering, Chinese Academy of Sciences(CAS), Beijing 100190, China

Received:2013-11-01 Revised:2014-03-12 Online:2015-03-01 Published:2015-02-28
Supported by:
Supported by the Science and Technology Ministry of China (2013BAC11B03) and National Nature Science Foundation of China (21476244, 21206180, 21406245).

Heterogeneous synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and methyl carbonate in methanol over a CeO₂ catalyst

Yan Cao, Huiquan Li, Xintao Li, Liguo Wang, Ganyu Zhu, Qing Tang

Key Laboratory of Green Process and Engineering, National Engineering Laboratory for Hydrometallurgical Cleaner Production Technology, Institute of Process Engineering, Chinese Academy of Sciences(CAS), Beijing 100190, China

通讯作者: Huiquan Li
基金资助:
Supported by the Science and Technology Ministry of China (2013BAC11B03) and National Nature Science Foundation of China (21476244, 21206180, 21406245).

Abstract

Abstract: The efficient synthesis of dimethylhexane-1,6-dicarbamate (HDC) from 1,6-hexanediamine (HDA) and methyl carbonate over a series of heterogeneous catalysts (e.g., MgO, Fe₂O₃, Mo₂O₃, and CeO₂) was investigated. The reaction pathway was confirmed as an alcoholysis reaction through a series of designed experiments. Under optimized conditions, 100% HDA conversion with 83.1% HDC_total and 16.9% polyurea was obtained using a onestep with high temperature procedurewith CeO₂ as the catalyst. A newtwo-stepwith variable temperature technology was developed based on the reaction pathway to reduce the polyurea yield. Using the proposed method, the HDC_total yield reached 95.2%, whereas the polyurea yield decreased to 4.8%. The CeO₂ catalyst showed high stability and did not exhibit any observable decrease in the HDC yield or any structural changes after four recycling periods.

Key words: Heterogeneous, Dimethylhexane-1,6-dicarbamate, Methyl carbonate, Reaction pathway, Two-step variable-temperature technology

摘要： The efficient synthesis of dimethylhexane-1,6-dicarbamate (HDC) from 1,6-hexanediamine (HDA) and methyl carbonate over a series of heterogeneous catalysts (e.g., MgO, Fe₂O₃, Mo₂O₃, and CeO₂) was investigated. The reaction pathway was confirmed as an alcoholysis reaction through a series of designed experiments. Under optimized conditions, 100% HDA conversion with 83.1% HDC_total and 16.9% polyurea was obtained using a onestep with high temperature procedurewith CeO₂ as the catalyst. A newtwo-stepwith variable temperature technology was developed based on the reaction pathway to reduce the polyurea yield. Using the proposed method, the HDC_total yield reached 95.2%, whereas the polyurea yield decreased to 4.8%. The CeO₂ catalyst showed high stability and did not exhibit any observable decrease in the HDC yield or any structural changes after four recycling periods.

关键词: Heterogeneous, Dimethylhexane-1,6-dicarbamate, Methyl carbonate, Reaction pathway, Two-step variable-temperature technology

Yan Cao, Huiquan Li, Xintao Li, Liguo Wang, Ganyu Zhu, Qing Tang. Heterogeneous synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and methyl carbonate in methanol over a CeO₂ catalyst[J]. , 2015, 23(2): 446-450.

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Heterogeneous synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and methyl carbonate in methanol over a CeO₂ catalyst

Heterogeneous synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and methyl carbonate in methanol over a CeO₂ catalyst

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