Document Type : Research Paper
Authors
Radiation Application Research School, Nuclear Science and Technology Research Institute
Abstract
Substitution of hydrogen with deuterium as a heavier and stable isotope in different molecules leads to interesting and significant effects in various industries like electronics and medicine. One of the important applications of heavy water is the usage of it in hydrogen–deuterium exchange reactions for the production of organic compounds having deuterium atom. Deuterated nitrobenzene is a valuable raw material for the production of deuterated aniline used in organic light-emitting diode industries. The aim of this study is to consider the required conditions for the synthesis of nitrobenzene-d5 with 99.5% atom D. Our studies indicated that preparation of nitrobenzene-d5 from hydrogen–deuterium exchange is not an appropriate method. In this article, under the condition of nitration with sulfuric acid and nitric acid as a source of nitronium, nitrobenzene-d5 was synthesized from benzene-d6 produced from the reaction of benzene with heavy water. Reaction temperature and concentration of sulfuric acid and nitric acid were optimized in order to avoid by-product formation and also to prevent reduction in isotopic enrichment during the conversion of benzene-d6 to nitrobenzene-d5. The product was characterized and analyzed by FT-IR, 1HNMR, mass spectroscopy, and gas chromatography.
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