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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

Application of Response Surface Methodology for Improving the Yield of 1,5-bis(ptoluenesulfonyl)- 3,7-Dihydroxyoctahydro-1,5-Diazocine

Author(s): Yang Zou, Jingyi Fei, Liangzhe Chen, Qingfeng Dong and Houbin Li*

Volume 16, Issue 3, 2019

Page: [398 - 404] Pages: 7

DOI: 10.2174/1570179415666181113144357

Price: $65

Abstract

Background: 3,3,7,7-tetrakis (difluoramino) octahydro-1,5-dinitro-1,5-diazocine (HNFX), as an important oxidizer in propellants, has received much attention due to its high density and energy. However, there are many difficulties that need to be solved, such as complex synthetic processes, low product yield, high cost of raw materials and complicated purification. In the synthesis of HNFX, the intermediate named 1,5-bis (p-toluenesulfonyl)-3,7-dihydroxyoctahydro-1, 5-diazocine (gem-diol), is difficult to synthesize.

Methods: A simple method was used to synthesize the gem-diol. This prepared gem-diol was characterized by FT-IR, 1H NMR, melting point and mass spectrometry. In order to increase the yield of gem-diol, response surface methodology (RSM) was introduced to optimize experimental conditions.

Results: After the establishment of the model, the optimal conditions of synthesis were found to be 9.33h for reaction time, 6.13wt. % for the concentration of NaOH and 1.38:1 for ratio of ECH (p-toluenesulfonamide): TCA (epichlorohydrin). Under the optimal conditions, the experimental value and the predicted value of yield were 22.18% and 22.92%, respectively.

Conclusion: 1,5-bis (p-toluenesulfonyl)-3,7-dihydroxyoctahydro-1,5-diazocine (gem-diol) can be synthesized using the low cost of chemical materials, including p-toluenesulfonamide, epichlorohydrin, sodium hydroxide and ethanol. Response surface methodology (RSM) is an effective method to optimize the synthesis process, thereby improving the yield of gem-diol.

Keywords: HNFX, 1-5-bis (p-toluenesulfonyl)-3-7-dihydroxyoctahydro-1-5-diazocine, response surface methodology (RSM), gem-diol, oxidizer, synthesis.

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Graphical Abstract

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