Microwave assisted facile synthesis of {1/1,3-bis/1,3,5-tris-[(2-nitroxyethylnitramino)-2,4,6-trinitrobenzene]} using bismuth nitrate pentahydrate as an eco-friendly nitrating agent
- 作者：D.M. Badgujar ; M.B. Talawar ; S.N. Asthana ; S. Venugopalan ; A. Subhan ; a Rao ; P.P. Mahulikar
- 关键词：Bismuth nitrate pentahydrate ; Eco-friendly nitration ; Microwave irradiation ; High energy materials ; Hazardous materials
- 刊名：Journal of Hazardous Materials
- 出版年：2008
- 期刊代码：50_03043894
- 类别：ce
- 出版时间：1 April 2008
- 卷：152
- 期：2
- 页码：820-825
- 文件大小：378 K
摘要
1-(2-Nitroxyethylnitramino)-2,4,6-trinitrobenzene (3a), 1,3-bis(2-nitroxyethyl nitramino)-2,4,6-trinitrobenzene (3b) and 1,3,5-tris(2-nitroxyethylnitramino)-2,4,6-trinitrobenzene (3c) were prepared by the nitration of 1-(2-hydroxyethylamino)-2,4,6-trinitrobenzene (2a) 1,3-bis(2-hydroxyethylamino)-2,4,6-trinitrobenzene (2b) and 1,3,5-tris(2-hydroxyethylamino)-2,4,6-trinitrobenzene (2c) using bismuth nitrate pentahydrate (eco-friendly nitrating agent) in tetrahydrofuran adsorbed on silica gel under microwave irradiation, respectively. Key intermediate compounds viz., 2a, 2b and 2c were synthesized by condensing picryl chloride, styphnyl chloride and 1,3,5-trichloro-2,4,6-trinitrobenzene with ethanol amine, respectively, based on the lines of the reported method. The synthesized compounds were characterized based on their physical constant, infrared (IR) spectroscopy and 1H nuclear magnetic resonance (NMR) spectroscopy. The spectroscopic data obtained indicated the formation of nitrate esters (3a–3c). The nitration methodology adopted in the present study is of relevance in the context of green chemistry. The target compounds (3a–3c) synthesized using eco-friendly approach are of interest from the point of high energy materials (HEMs).