Hydroxy benzonitril preparation process

A technology of salicylonitrile and process, applied in the field of preparing salicylonitrile, can solve problems such as unfavorable industrial scale-up operation, inability to meet environmental protection requirements, large phosphorus-containing waste water, etc., and achieves ensuring preparation yield, increasing synthesis efficiency, and reducing by-products The effect of the formation of phenol

Inactive Publication Date: 2017-02-22
禹城禹圳生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process produces a large amount of phosphorus-containing wastewater, which cannot meet the increasingly stringent environmental protection requirements
[0004] "Research on the preparation of o-hydroxybenzonitrile by ammonium salicylate method" (Li Wenqing, Cai Zhaosheng, Guangdong Chemistry [J], 2011, 38 (5), 87-88) discloses that ammonium salicylate, urea and sulfamic acid are used in Synthetic salicylonitrile in methyl salicylate; But, in the process of preparing ammonium salicylate, this process needs to evaporate water completely, and this operation is unfavorable for industrial scale-up operation; And, this process needs about three times the equivalent of urea and sulfamic acid to ensure that the yield of salicylonitrile is about 86%, and the waste of raw materials is serious
[0005] According to the applicant's knowledge and retrieval, no patents or literature records have been found that directly use salicylic acid as a raw material to obtain salicylonitrile synthesis process in one step

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Mix 2 grams of magnesium oxide and 2.4 grams of cyanuric chloride evenly, add them into a 1L three-necked bottle, and then add 27.6 grams (0.2mol) of salicylic acid, 24 grams (0.4mol) of urea, and 40.7 grams (0.42 grams) of sulfamic acid. mol) and 500 milliliters of methyl benzoate, the temperature was raised to 150° C., and reacted for 4 hours; then, the temperature was lowered to 90° C., 300 milliliters of water was added, the organic phase was separated while it was hot, the methyl benzoate was recovered by distillation under reduced pressure, and the solid was precipitated by cooling. Filtration and drying yielded 19.1 g of a light yellow solid with a yield of 80.2%; melting point: 88-93°C; 1 H NMR (400MHz, DMSO-d 6 )δ6.88(dd, J=7.6,7.6Hz,1H),7.01(d,J=8.4Hz,1H),7.44(dd,J=7.6,7.6Hz,1H),7.55(d,J=7.6 Hz, 1H), 11.02 (br, 1H), the content is 95.3% (GC).

Embodiment 2

[0020] Mix 2 grams of magnesium oxide and 2.4 grams of cyanuric chloride evenly, add them into a 1L three-necked bottle, and then add 27.6 grams (0.2mol) of salicylic acid, 24 grams (0.4mol) of urea, and 40.7 grams (0.42 grams) of sulfamic acid. mol) and 500 milliliters of ethyl benzoate, the temperature was raised to 150° C., and the reaction was carried out for 4 hours; then, the temperature was lowered to 90° C., 300 milliliters of water was added, the organic phase was separated while it was hot, the ethyl benzoate was recovered by distillation under reduced pressure, and the solid was precipitated by cooling. After filtration and drying, 17.7 g of a light yellow solid was obtained, with a yield of 74.4%; melting point: 89-93° C., content: 95.5% (GC).

Embodiment 3

[0022] Mix 2 grams of magnesium oxide and 2.4 grams of cyanuric chloride evenly, add them into a 1L three-necked bottle, and then add 27.6 grams (0.2mol) of salicylic acid, 24 grams (0.4mol) of urea, and 40.7 grams (0.42 grams) of sulfamic acid. mol) and 500 ml of diphenyl ether, heated to 150°C, and reacted for 4 hours; then, cooled to 90°C, added 300 ml of water, separated the organic phase while hot, recovered diphenyl ether by distillation under reduced pressure, and cooled to 40°C to precipitate solid , filtered, and dried to obtain 17.3 grams of a light yellow solid, with a yield of 72.8%; melting point: 91-94°C, and a content of 96.5% (GC).

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Abstract

The invention discloses a hydroxy benzonitril preparation process and belongs to the technical field of organic synthesis. The hydroxy benzonitril preparation process is characterized by comprising the steps of enabling salicylic acid, urea, sulfamic acid and a catalyst to react in a solvent, and separating to obtain hydroxy benzonitril, wherein the catalyst is a mixture of magnesium oxide and cyanuric chloride at the weight ratio of 1:(1-2), the reaction temperature is 140-160 DEG C, and the materials of the salicylic acid, the urea, the sulfamic acid and the catalyst are added at the weight ratio of 1:(0.8-1.2):(1.4-1.8):(0.05-0.2). The efficient and practical compound catalyst is creatively used, the salicylic acid is directly used as the material, the hydroxy benzonitril is synthesized in a one-step method, the product is easy to separate and purify, the operation is convenient, the product purity is high, and the yield is high.

Description

technical field [0001] The invention relates to a process for preparing salicylonitrile, which belongs to the technical field of organic synthesis. Background technique [0002] Salicylonitrile, also known as 2-hydroxybenzonitrile, is mainly used as an intermediate of the drug Bunirolol and an intermediate of the fungicide Azoxystrobin. [0003] At present, salicylamide is generally used as raw material in industry, phosphorus oxychloride is used as dehydrating agent, and salicylonitrile is prepared by reflux reaction in toluene. This process produces a large amount of phosphorus-containing wastewater, which cannot meet the increasingly stringent environmental protection requirements. [0004] "Research on the preparation of o-hydroxybenzonitrile by ammonium salicylate method" (Li Wenqing, Cai Zhaosheng, Guangdong Chemistry [J], 2011, 38 (5), 87-88) discloses that ammonium salicylate, urea and sulfamic acid are used in Synthetic salicylonitrile in methyl salicylate; But, i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/22C07C255/53
CPCC07C253/22C07C255/53
Inventor 赵景瑞焦志刚杨正龙邹忠华翟宏斌
Owner 禹城禹圳生物科技有限公司
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