Scalable Synthesis of 1,1-Diamino-2,2-dinitroethene Without Hazardous Intermediates or by-Products |
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| Authors: | Zdeněk Jalový Jan Ottis Kamil Dudek Aleš Růžicka Antonín Lyčka |
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| Affiliation: | 1. University of Pardubice, Faculty of Chemical Technology, Institute of Energetic Materials , Pardubice , Czech Republic;2. Explosia a.s. , Pardubice , Czech Republic;3. Faculty of Chemical Technology, Department of General and Inorganic Chemistry , University of Pardubice , Pardubice , Czech Republic;4. Research Institute for Organic Syntheses (VUOS) , Rybitví , Czech Republic |
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| Abstract: | A process for the preparation of 1,1-diamino-2,2-dinitroethene suitable for scale-up was developed. The crucial features to allow scalability and enhance the process safety were the improved synthesis of 2-methoxy-2-methylimidazolidine-4,5-dione and its conversion into 2-hydroxy-2-methylimidazolidine-4,5-dione, which is a new intermediate in the synthesis of 1,1-diamino-2,2-dinitroethene. Its nitration produced 2-(dinitromethylidene)-imidazolidine-4,5-dione, whose hydrolysis into 1,1-diamino-2,2-dinitroethene was further improved. The use of trifluoroacetic acid to remove sulfuric acid prior to hydrolysis is no longer required. The described procedure yields no hazardous intermediates such as dinitromethane or 2-(dinitromethylidene)-5,5-dinitrodihydropyrimidine-4,6(1H,5H)-dione. Thus, the process safety was enhanced in comparison with the commercial production process starting from 2-methylpyrimidine-4,6-dione. |
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| Keywords: | 1,1-diamino-2,2-dinitroethene 2-hydroxy-2-methylimidazolidine-4 2-methoxy-2-methylimidazolidine-4,5-dione 5-dione DADNE FOX-7 |
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