Environment friendly method for preparing DMF (Dimethyl Formamide) solution of 2-hydroxy-benzonitril, DMF solution of 2-hydroxy-benzonitril and application thereof

An o-hydroxybenzonitrile and environment-friendly technology, which is applied to the environmentally friendly preparation of DMF solutions of o-hydroxybenzonitrile, DMF solutions of o-hydroxybenzonitrile and their application fields, can solve the problem that the product quality is difficult to improve and the yield is difficult to improve. low production costs and rising production costs, to achieve the effect of reducing overall production costs

Active Publication Date: 2012-06-27
上海禾本药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Huang Shan et al. reported the technology of preparing salicylonitrile by dehydration of triphosgene and salicylamide (Shanxi Chemical Industry, 2009, 29, 4). Salicylamide and triphosgene were reacted in toluene at 100-105°C, and the crude product was recrystallized with toluene. Although the small test gives a yield of about 90%, the yield is not high in the actual industrial production process, the product quality is difficult to improve, it is difficult to exceed 95%, and there are many impurities, which affect the production of subsequent products and lead to the failure of azoxystrobin. Synthesis is difficult to obtain high-quality products
Although the crude product o-hydroxybenzonitrile can reach a content of more than 98% after multiple purifications, the production cost has risen sharply, which has no practical significance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Under the cooling of the ice-water mixture, 11.88 g (0.04 mol) of triphosgene was added in batches to 50 ml of DMF. Stirring was continued for 30 minutes after the addition was complete. Control the temperature not to exceed 15°C. 13.7 grams of salicylamide (0.1 mol) was added in batches to the above reaction solution, and the temperature was controlled at 5-15°C. After the addition was complete, the ice-water cooling bath was removed, the temperature was naturally raised to room temperature, and stirring was continued for one hour to obtain a DMF solution of o-hydroxybenzonitrile. The o-hydroxybenzonitrile content is 98.3%. The chemical conversion rate is 99.1%; the selectivity is 98.2%.

Embodiment 2

[0039] Under the cooling of the ice-water mixture, 11.88 g (0.04 mol) of triphosgene was added in batches to 50 ml of DMF. Stirring was continued for 30 minutes after the addition was complete. Control the temperature not to exceed 15°C. 13.7 g of salicylamide (0.1 mol) was added in batches to the above reaction solution, and the temperature was controlled at 5-15°C. After the addition was complete, the ice-water cooling bath was removed, the temperature was naturally raised to room temperature, and the stirring was continued for one hour; the ice-water mixture was cooled to 15°C again. Add 16.56 g (0.12 mol) of potassium carbonate, stir for 15 minutes, remove the ice-water bath, naturally warm up to room temperature and continue stirring for 6 hours, and filter to obtain a DMF solution of o-hydroxybenzonitrile. The o-hydroxybenzonitrile content is 98.6%. The chemical conversion rate is 99.4%; the selectivity is 98.4%.

Embodiment 3

[0041] Under the cooling of the ice-water mixture, 11.88 g (0.04 mol) of triphosgene dissolved in 25 ml of ethyl acetate was added dropwise to 50 ml of DMF, and stirring was continued for 30 minutes after the addition was complete. Control the temperature not to exceed 15°C. 13.7 g of salicylamide (0.1 mol) was added in batches to the above reaction solution, and the temperature was controlled at 5-15°C. After the feeding was completed, the ice-water cooling bath was removed, and the temperature was naturally raised to room temperature, and the stirring was continued for one hour, and the ethyl acetate was distilled off by concentration with a rotary evaporator under reduced pressure to obtain a DMF solution of o-hydroxybenzonitrile. The o-hydroxybenzonitrile content is 98.7%. The chemical conversion rate is 99.5%; the selectivity is 98.5%.

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Abstract

The invention discloses an environment friendly method for preparing a DMF (Dimethyl Formamide) solution of 2-hydroxy-benzonitril, which is characterized in that triphosgene and salicylamide are respectively added into DMF to be fully reacted. With the preparation method disclosed by the invention, more than 98% of 2-hydroxy-benzonitril (excluding solvent) can be obtained, the chemical conversion and the selectivity are both greater than 98%, and no problems exist if the 2-hydroxy-benzonitril is directly applied for the next step of reaction. In the process of production, no polluting waste gas and waste water are discharged, scraps are inorganic salts which can directly used or organic amine hydrochlorides which can be recycled, the comprehensive production cost of the 2-hydroxy-benzonitril is greatly reduced, and the production process is environment friendly.

Description

technical field [0001] The discovery relates to an environmentally friendly method for preparing a DMF solution of o-hydroxybenzonitrile, a DMF solution of o-hydroxybenzonitrile and applications thereof. Background technique [0002] O-hydroxybenzonitrile, commonly known as salicylonitrile, also known as 2-hydroxybenzonitrile, o-hydroxybenzonitrile, 2-cyanophenol, etc., molecular formula C7H5NO, CAS registration number 611-20-1, has certain water solubility, Pka =7.17, unstable to strong bases and oxidants. As a pharmaceutical intermediate, it can be used to synthesize Bunirolol hydrochloride, a drug for treating hypertension and angina pectoris. As a pesticide intermediate, it can be used to synthesize the fungicide azoxystrobin. In addition, it can also synthesize a variety of spices and liquid crystal materials. [0003] Salicylamide, white or slightly pink crystalline powder. The melting point is 140°C. Salicylamide is easily soluble in hot water, alcohol, ether and c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/53C07C253/20C07D239/52C07C255/54C07C253/30
Inventor 叶光武张小兵赵凌鹄汪青松张万贞
Owner 上海禾本药业股份有限公司
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