Manufacturing technology of isoluminol

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Isoluminol, also known as 4-aminophthaloyl hydrazide, is a white powder with CAS No. 3682-14-2. Luminol is a commonly used luminol chemiluminescence reagent. Its luminescence mechanism is oxidation luminescence. It is catalyzed by horseradish peroxidase under alkaline conditions and oxidized by H2O2 to produce an excited intermediate of 4-aminophthalic acid. When it returns to the ground state, it will emit photons. Commonly used in food, environment, criminal investigation, medicine and other fields. Several methods of making isoluminol will be introduced below.

1. Phthalimide was prepared from phthalic anhydride and urea; Then 4-nitro-phthalimide was prepared under the catalysis of concentrated sulfuric acid and fuming nitric acid; 4-nitro-phthaloyl hydrazide was prepared by adding hydrazine hydrate; Then in the alkaline solution environment, the target product isoluminol was prepared by using stannous chloride solution as catalyst. The synthesis process of this method is simple and the reaction operation is simple, but stannous chloride is used as the catalyst for the catalytic reaction, which will produce a large amount of inorganic tin waste, which will pollute the environment and do not meet the requirements of green synthesis.

2. Diacetyl Phthaloyl hydrazide was prepared by the reaction of Phthaloyl hydrazide with acetylation reagent; Then react with nitroso compounds to obtain nitroso diacetyl Phthaloyl hydrazide; Then, nitroso Phthaloyl hydrazide was obtained by deacetylation; Isoluminol was obtained by reduction reaction. This method makes full use of a large number of Phthaloyl hydrazide by-products in the existing Gabriel amine synthesis method as raw materials. The raw materials are cheap and easy to obtain. At the same time, the synthesis process is simple and the yield of isoluminol product is high, but its advantages are also its disadvantages. Taking the by-products of Gabriel amine as raw materials, its quality is unstable and the batch difference is large. In addition, the intermediate nitroso compounds in the preparation process are highly toxic and have potential safety hazards, It is not suitable for the needs of large-scale industrial production.

3. Firstly, phthalimide was prepared, then reacted with concentrated sulfuric acid and fuming nitric acid, cooled and filtered to obtain 4-Nitrophthalimide. Then the preparation of 4-nitrophthaloyl hydrazide is mixed with a certain concentration of hydrazine hydrate and water and refluxed to obtain an orange red solution. After cooling, adjust the pH with glacial acetic acid, and obtain a light yellow solid 4-nitrophthaloyl hydrazide through precipitation, washing, suction filtration and drying; Finally, dissolve 4-nitrophthaloyl hydrazide in sodium hydroxide solution, drop the solution into the pure solution containing 56g stannous chloride concentrated hydrochloric acid under continuous stirring, add nano titanium dioxide, and then react under ultraviolet light to obtain a colorless clear solution. After cooling, precipitation, suction filtration, precipitation and suction filtration, and then dry to obtain a white powdery solid, namely isoluminol; This method is cumbersome and not suitable for industrial production, but it has the advantages of high yield and high purity of isoluminol.

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