Improved Synthesis of 4-Bromo-5-Nitro-1,8-Naphthalene Anhydride
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The National Natural Science Foundation of China (General Program, Key Program, Major Research Plan)

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    Abstract:

    Abstract: Using acenaphthene as raw material and NaBr/CeCl3.7H2O/H2O2 as bromination reagent, 5-bromoacenaphthene was obtained. Then it was nitrated with Al(NO3)3.9H2O/CH3COOH to synthesize 4-bromo-5-nitroacenaphthene. Finally, using cobalt acetate/manganese acetate/N-Hydroxyphthalimide (NHPI)/oxygen as oxidant, 4-bromo-5-nitro-1,8-naphthalene anhydride was prepared, which is an important intermediate of naphthalimide fluorescent dyes. The effects of raw material ratio, reaction temperature, reaction time, and solvent on the reaction yield were explored, and the optimal reaction conditions were obtained. For the bromination reaction, the temperature was 25 ℃, the reaction time was 3 h, the ratio of the amount of substances of acenaphthene, cerium chloride heptahydrate, and sodium bromide was 2∶1∶2.4, and the yield was 86.4%. For the nitration reaction, the temperature was 45 ℃, the reaction time was 8 h, the ratio of the amount of substances of 5-bromoacenaphthene, Al(NO3)3.9H2O was 1∶1.2, and the yield was 88.4%. For the oxidation reaction, the temperature was 110 ℃, the reaction time was 5 h, the ratio of the amount of substances of cobalt acetate, Manganese acetate, NHPI and 4-bromo-5-nitroacenaphthene was 1.2∶0.5∶1.2∶10, and the yield was 72.3%. A preliminary scale-up experiment was conducted by using this method. The reaction yield was still high after the reaction was expanded by 5-20 times. This method has the characteristics of cheap and readily available raw materials, mild and environmentally friendly reaction process, high product yield, and easy industrialization.

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History
  • Received:February 05,2021
  • Revised:February 05,2021
  • Adopted:February 19,2021
  • Online: April 07,2021
  • Published: