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Preparation method of salicylonitrile

A technology of o-hydroxybenzonitrile and o-hydroxybenzamide, which is applied in the dehydration preparation of carboxylic acid amides, organic chemistry, etc., can solve problems such as being unsuitable for large-scale production, complicated process, difficult to remove, etc. Simple and safe, high-yield effect

Active Publication Date: 2013-04-03
湖南海利常德农药化工有限公司
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Problems solved by technology

A method for synthesizing o-hydroxybenzonitrile under alkaline conditions by using o-cresol as a raw material through ether formation and methyl cyanation. This synthesis method is complex in process and low in yield, and is not suitable for large-scale production
A method for dehydrating o-hydroxybenzamide to generate o-hydroxybenzonitrile. This synthesis method produces phosphorus-containing wastewater, and the main impurities containing phosphorus in the product are difficult to remove

Method used

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  • Preparation method of salicylonitrile
  • Preparation method of salicylonitrile
  • Preparation method of salicylonitrile

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Effect test

Embodiment 1

[0014] 13.7g (0.1mol) o-hydroxybenzamide, 41.1g (0.39mol) xylene, 0.014g (1.6×10 -4 mol) dioxane was added to a 100mL three-necked flask with a stirring and reflux tube, heated to reflux, and 11.9g (0.12mol) phosgene was introduced within 2hr.

[0015] After 0.5hr of heat preservation, 21g of xylene was evaporated from the reaction solution, the concentrated solution was stirred and crystallized in an ice-water bath, and 11.8g of o-hydroxybenzonitrile was obtained by filtration, with a content of 98.3% (liquid chromatography external standard method, the same below), and the yield 97.5%.

Embodiment 2

[0017] 13.7g (0.1mol) o-hydroxybenzamide, 68.5g (0.65mol) xylene, 0.041g (4.7×10 -4 mol) dioxane was added to a 100mL three-necked flask with a stirring and reflux tube, heated to reflux, and 11.9g (0.12mol) phosgene was introduced within 3hr.

[0018] After 0.5 hr of heat preservation, 34 g of xylene was evaporated from the reaction solution, the concentrated solution was stirred and crystallized in an ice-water bath, and 11.6 g of o-hydroxybenzonitrile was obtained by filtration, with a content of 98.9% and a yield of 96.4%.

Embodiment 3

[0020] 13.7g (0.1mol) o-hydroxybenzamide, 108g (1.02mol) xylene, 0.068g (7.7×10 -4 mol) dioxane was added to a 100mL three-necked flask with a stirring and reflux tube, heated to reflux, and 11.9g (0.12mol) phosgene was introduced within 4hr.

[0021] After 0.5 hr of heat preservation, 55 g of xylene was evaporated from the reaction solution, the concentrated solution was stirred and crystallized in an ice-water bath, and 11.5 g of o-hydroxybenzonitrile was obtained by filtration, with a content of 99.2% and a yield of 95.9%.

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Abstract

The invention discloses a method for synthesizing salicylonitrile by using ortho-hydroxybenzamide as a raw material, dioxane or tetrahydropyrane and tetrahydrofuran as catalysts, and dimethylbenzene or benzene, methylbenzene and chlorobenzene as solvents through introducing phosgene at a refluxing temperature. The reaction formula is described in the specification. The invention relates to a method for preparing the salicylonitrile without generating waste water and waste slag. Compared with the prior art, the method has the advantages of less reaction byproducts, high quality, high yield, simplicity and safety in operation, low price and easily available raw material, the content of the salicylonitrile is not less than 98 percent (liquid chromatogram, external standard method), and the yield of the salicylonitrile is not less than 95 percent (in the terms of o-hydroxybenzamide).

Description

technical field [0001] The invention relates to a method for preparing an intermediate o-hydroxybenzonitrile of the fungicide azoxystrobin. Background technique [0002] O-Hydroxybenzonitrile is an important intermediate for the synthesis of a new type of high-efficiency broad-spectrum methoxyacrylate fungicide azoxystrobin, with a structural formula: [0003] [0004] There are many ways to synthesize it. After phosgene dehydration, o-hydroxybenzamide directly generates o-hydroxybenzonitrile. This method produces waste water, and the product content and yield are low. The method of synthesizing the intermediate o-hydroxyaldoxime with o-hydroxybenzaldehyde and hydroxylamine hydrochloride, and then synthesizing o-hydroxybenzonitrile under acidic conditions, the yield is less than 90%, and the content is less than 95%. The operating conditions are mild, but the synthesis method produces a large amount of Refractory waste water. A method for synthesizing o-hydroxybenzonitr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/53C07C253/20
Inventor 臧阳陵周勇陈明周锦萍徐建兵黄幼援
Owner 湖南海利常德农药化工有限公司
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