Molecular Design and Property Prediction for a Series of 3,3-Bis(difluoroamino)-1,5-substituted-pentane Derivatized as Energetic Plasticizers

doi:10.6023/cjoc201808024

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 170-176.DOI: 10.6023/cjoc201808024 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

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含能增塑剂用系列3,3-二(二氟氨基)-1,5-取代戊烷衍生物的分子设计和性能预测

王万军^a,b, 李欢^a, 潘仁明^a, 朱卫华^a

a 南京理工大学化工学院南京 210094;
b 中国科学院上海有机化学研究所上海 200032

收稿日期:2018-08-20 修回日期:2018-10-22 发布日期:2018-11-30
通讯作者: 王万军 E-mail:wangwj@sioc.ac.cn
基金资助:
国家自然科学基金（No.51603103）资助项目.

Molecular Design and Property Prediction for a Series of 3,3-Bis(difluoroamino)-1,5-substituted-pentane Derivatized as Energetic Plasticizers

Wang Wanjun^a,b, Li Huan^a, Pan Renming^a, Zhu Weihua^a

a School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2018-08-20 Revised:2018-10-22 Published:2018-11-30
Contact: 10.6023/cjoc201808024 E-mail:wangwj@sioc.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51603103).

1. Molecular Design and Property Prediction for a Series of 3,3-Bis(difluoroamino)-1,5-substituted-pentane Derivatized as Energetic Plasticizers.PDF(297KB)

Abstract

3,3-Bis(difluoroamino)-1,5-dinitratopentane was used as energetic plasticizer with improving energy properties and low glass transition temperature. To obtain more new difluoroamino energetic compounds with similar sturctures, a series of 3,3-bis(difluoroamino)-1,5-substituted-pentane derivatives were designed as candidates of novel energetic plasticizers. The heats of formation (HOFs), electronic structure, energy property and thermal stability were studied using density functional theory (DFT) method. The difluoroamino groups can increase energy gaps of electronic structure, density and detonation properties among the title compounds. Especially, 1,3,3,5-tetra(difluoroamino)pentane (S₃) has given outstanding values of potential energetic plasticizer. Its crystal density (1.91 g/cm³), detonation velocity (9.01 km/s), detonation pressure (37.31 GPa) and impact sensitivity (h₅₀ 29.83 cm) are very close to those of cyclotetramethylenetetranitramine (HMX). Furthermore, S₃ can be synthesized via some mature processes in five steps.

Key words: difluoroamino pentane, density functional theory, heats of formation, detonation properties, bond

Cite this article

Wang Wanjun, Li Huan, Pan Renming, Zhu Weihua. Molecular Design and Property Prediction for a Series of 3,3-Bis(difluoroamino)-1,5-substituted-pentane Derivatized as Energetic Plasticizers[J]. Chin. J. Org. Chem., 2019, 39(1): 170-176.

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含能增塑剂用系列3,3-二(二氟氨基)-1,5-取代戊烷衍生物的分子设计和性能预测

Molecular Design and Property Prediction for a Series of 3,3-Bis(difluoroamino)-1,5-substituted-pentane Derivatized as Energetic Plasticizers

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