What are the production processes of isoluminol

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Isoluminol also known as 4-aminophthalic hydrazide, is a white powder with a CAS number of 3682-14-2. Luminol is a commonly used luminol chemiluminescent reagent. Its luminescence mechanism is oxidation reaction. It is catalyzed by horseradish peroxidase under alkaline conditions and oxidized by H2O2 to generate 4-aminophthalic acid. The excited state intermediate of , emits a photon when it returns to the ground state. Commonly used in food, environment, criminal investigation, medicine and other fields. Here are a few ways to make isoluminol.

1. Using phthalic anhydride as raw material, react with urea to obtain phthalimide products; then under the catalysis of concentrated sulfuric acid and fuming nitric acid, 4-nitro-phthalimide is obtained amine; then adding hydrazine hydrate to react to obtain 4-nitro-phthalic hydrazide; and then in an alkaline solution environment, using stannous chloride acid solution as a catalyst, catalyzing the preparation of the target product isoluminol. The synthesis process of this method is simple and the reaction operation is simple and convenient, but stannous chloride is used as the catalyst to catalyze the reaction, which will generate a large amount of inorganic tin waste, which has great environmental pollution and does not meet the requirements of green synthesis.
2. Using phthalic hydrazide as a raw material, react with an acetylating reagent to obtain diacetyl phthalic hydrazide; then react with a nitroso compound to obtain nitroso diacetyl phthalic hydrazide; Subsequent deacetylation reaction yields nitrosophthalic hydrazide; and then reduction reaction yields isoluminol. This method makes full use of a large amount of phthalic hydrazide by-products in the existing Gabriel amine synthesis method as raw materials, the raw materials are cheap and easy to obtain, the synthesis process is simple and the yield of isoluminol products is high, but the advantages It is also its shortcoming. Taking the by-product of Gabriel amine as a raw material, its quality is unstable, and the difference between batches is large. In addition, the intermediate nitroso compound in the preparation process has high toxicity and has potential safety hazards, which is not suitable for industrialized large-scale production. need.
3. First prepare phthalimide, then react it with concentrated sulfuric acid and fuming nitric acid, and then cool and suction to obtain 4-nitrophthalimide. Then, the preparation of 4-nitrophthalic acid hydrazide is mixed with a certain concentration of hydrazine hydrate and water and refluxed to obtain an orange-red solution. After cooling, the pH is adjusted with glacial acetic acid, and through precipitation, washing, suction filtration, and drying to obtain Light yellow solid 4-nitrophthalic hydrazide; finally 4-nitrophthalic hydrazide was warmed and dissolved in sodium hydroxide solution, and the solution was dripped under constant stirring until the solution contained 56 g of stannous chloride. In the pure clear solution of concentrated hydrochloric acid, nano-titanium dioxide is added, and then reacted under the irradiation of ultraviolet light to obtain a colorless and clear solution. That is isoluminol; this method has complicated synthesis steps and is not suitable for industrial production, but has the advantages of high yield and high purity of the prepared isoluminol.
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