Synthesis of Cyclotetramethlene Tetranitramine by Three Stage

Singh, Balwant; Bhatia, Pooja; Singh, Harinder

doi:10.14429/dsj.32.6319

Cited by 5 publications

References 1 publication

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Mechanism Improvement and Process Optimization of the One‐Pot Synthesis of 3.7‐Dinitro‐1,3,5,7‐Tetraazabicyclo[3,3,1]nonane from Urea

Zhu

Meng

Liu

et al. 2018

Propellants Explo Pyrotec

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As a key precursor in the preparation of octahydro‐1,3,5,7‐tetranitro‐1,3,5,7‐tetrazocine (HMX), 3,7‐dinitro‐1,3,5,7‐tetraazabicyclo[3,3,1]nonane (DPT) prepared from urea by a modified one‐pot method has a bright future. On the basis of our previous work (Reaction Mechanism of One‐Pot Synthesis of Dinitro Pentamethylene Tetramine, Chinese Journal of Organic Chemistry 2010, 30 (3), 414–418.) [1], a novel intermediate 3‐nitro‐1,3,5,7‐tetraazabicyclo[3,3,1]nonane was captured and isolated, and the key reactive intermediate hexahydro‐1‐nitro‐1,3,5‐triazine was directly captured and confirmed by HPLC‐MS. Thus, a modified synthetic mechanism for DPT was elaborated, and based which DPT preparation process was optimized.

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Mechanism Improvement and Process Optimization of the One‐Pot Synthesis of 3.7‐Dinitro‐1,3,5,7‐Tetraazabicyclo[3,3,1]nonane from Urea

Zhu

Meng

Liu

et al. 2018

Propellants Explo Pyrotec

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A Stepwise Strategy for the Synthesis of HMX from 3,7‐Dipropionyl‐1,3,5,7‐Tetraazabicyclo[3.3.1]Nonane

Zhang

Ruan

et al. 2018

Propellants Explo Pyrotec

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1,3,5,7-Tetranitro-1,3,5,7-tetraazacyclooctane (HMX) is one of the most powerful and widely used explosives. A new method for the synthesis of HMX from 3,7dipropionyl-1,3,5,7-tetraazabicyclo[3.3.1]nonane (DPPT) was investigated. Two important intermediates, 1,5-dipropionyl-3-nitroso-7-nitro-1,3,5,7-tetraazacyclooctane (DPNNO) and 1,5-dipropionyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane (DPDN), were isolated from the reaction mixture. The reaction mechanism, involving a nitrolysis-nitrosolysis-nitrolysis-nitrolysis process, was proposed and verified by the 1 H-NMR tracking. Based on the reaction mechanism, a stepwise method to prepare HMX from DPPT was developed. DPPT could be efficiently and smoothly converted to DPNNO in red fuming nitric acid with excellent yield up to 94.2 %. The influence factors on the yields of HMX such as reaction temperature, loading amounts of N 2 O 5 were investigated. Under the optimized conditions, HMX was obtained with a satisfactory yield of 85.0 %. The overall yield of the stepwise procedure was as high as 80.0 %.A Stepwise Strategy for the Synthesis of HMX from 3,7-Dipropionyl-1,3,5,7-Tetraazabicyclo[3.3.1]Nonane

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Investigation of the key active intermediate for the synthesis of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane: Hydrolysis and nitrolysis of 1-acetoxymethyl-3,5,7-trinitro-1,3,5,7-tetraazacyclooctane

Zhang

et al. 2020

Energetic Materials Frontiers

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Synthesis of Cyclotetramethlene Tetranitramine by Three Stage

Cited by 5 publications

References 1 publication

Mechanism Improvement and Process Optimization of the One‐Pot Synthesis of 3.7‐Dinitro‐1,3,5,7‐Tetraazabicyclo[3,3,1]nonane from Urea

Mechanism Improvement and Process Optimization of the One‐Pot Synthesis of 3.7‐Dinitro‐1,3,5,7‐Tetraazabicyclo[3,3,1]nonane from Urea

A Stepwise Strategy for the Synthesis of HMX from 3,7‐Dipropionyl‐1,3,5,7‐Tetraazabicyclo[3.3.1]Nonane

Investigation of the key active intermediate for the synthesis of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane: Hydrolysis and nitrolysis of 1-acetoxymethyl-3,5,7-trinitro-1,3,5,7-tetraazacyclooctane

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