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        Microfluidic continuous flow synthesis of 1,5-ditosyl-1,5-diazocane- 3,7-dione using response surface methodology

        Yang Zou,Tao Zhang,Guannan Wang,Mengwen Zhou,Yabo Xiong,Shaoyun Huang,Houbin Li,Xinghai Liu 한국공업화학회 2020 Journal of Industrial and Engineering Chemistry Vol.82 No.-

        3,3,7,7-tetrakis(difluoroamino) octahydro-1,5-dinitro-1,5-diazocine (HNFX) is a high-density energeticoxidizer with four difluoroamino groups (-NF2). In this study, 1,5-ditosyl-1,5-diazocane-3,7-dione, as animportant intermediate for synthesis of HNFX, was successfully synthesized using Swern oxidation in atraditional batch reactor and a continuousflow microreactor, respectively. 1,5-dotosyl-1,5-diazocane-3,7-dione was characterized by HPLC, FTIR, 1H NMR, 13C NMR, Mass spectrometry, and X-ray crystaldiffraction. Compared with the traditional batch reactor, the microreactor showed several advantages,including less reaction time, milder reaction temperature, higher yield and selectivity for 1,5-ditosyl-1,5-diazocane-3,7-dione. Moreover, the microreactor could ensure the safer and large-scale industrialproduction of 1,5-ditosyl-1,5-diazocane-3,7-dione. However, some solids produced in Swern oxidationwhich might block the channels (diameter of 0.3 mm) in the microreactor. To overcome the challenges,the experimental device was modified to suit for Swern oxidation, contributing to wider application ofthe microreactor. Besides, response surface methodology (RSM) was introduced and an appropriatemathematical model was built to optimize experimental conditions. The optimum experimentalparameters were recommended as 7.8 C for the reaction temperature, 7.7 mL/min for theflow rate, and6% for the concentration of oxalyl chloride. The actual yield of 1,5-ditosyl-1,5-diazocane-3,7-dione was89.7%, which was in great agreement with the highest predicted yield (90.1%).

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