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Preparation method of o(p)-hydroxybenzonitrile

A technology of hydroxybenzonitrile and halogenated benzonitrile is applied in the field of preparation of important fine chemical intermediate o-hydroxybenzonitrile, which can solve the problems of being difficult to obtain, not suitable for large-scale production, etc. Industrial production, the effect of reducing production costs

Active Publication Date: 2012-01-11
JIANGSU LIANHE CHEM TECH +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0029] The shortcoming of this method is that no matter the raw material is ortho (p) cyanoanisole or o (p) methyl anisole, it is not easy to obtain on the market, and it is not suitable for large-scale production

Method used

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  • Preparation method of o(p)-hydroxybenzonitrile
  • Preparation method of o(p)-hydroxybenzonitrile
  • Preparation method of o(p)-hydroxybenzonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Add 250 g of sodium methoxide methanol solution with a solution concentration of 20.7% and 60 g of o-chlorobenzonitrile into a 1000 ml autoclave, replace the autoclave air with nitrogen, raise the temperature to 160°C, and increase the autoclave pressure to 2.5Mpa, and react in this state After 6-9 hours, complete the reaction, cool to below 50℃, recover methanol under reduced pressure (can be used), add cold water to dissolve the residual product, filter the insoluble matter, acidify with 36% hydrochloric acid to precipitate a white product o-hydroxybenzene Formonitrile, after drying, the content is >99.0%, the mass is 50.5g, and the yield is 96.4%.

Embodiment 2

[0056] Add 258g of 28.5% sodium methoxide methanol solution and 75g of p-chlorobenzonitrile into a 1000ml autoclave, replace the autoclave air with nitrogen, raise the temperature to 200℃, and increase the autoclave pressure to 2.8Mpa, and react 5 in this state After ~7 hours, the reaction is completed, the temperature is lowered to below 50°C, the methanol is recovered under reduced pressure (can be used), cold water is added to dissolve the remaining product, the insoluble matter is filtered, and then acidified with 36% hydrochloric acid to precipitate a white product, p-hydroxybenzonitrile. After drying, the content is >99.0%, and the mass is 62.8g. The yield was 95.9%.

Embodiment 3

[0058] Add 244g of 25.7% sodium ethoxide ethanol solution and 70g of o-bromobenzonitrile into a 1000ml autoclave, replace the autoclave air with nitrogen, raise the temperature to 200℃, and increase the autoclave pressure to 3.0Mpa, and react in this state After 5-7 hours, complete the reaction, cool to below 50℃, recover ethanol under reduced pressure (can be used), add cold water to dissolve the residual product, filter the insoluble matter, acidify with 36% hydrochloric acid, and precipitate the white product o-hydroxybenzonitrile After drying, the content is >99.0%, and the mass is 43.5g. The yield was 96.1%.

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Abstract

The invention provides a preparation method of o(p)-hydroxybenzonitrile which is an important fine chemical intermediate applied in medical and pesticide fields. The method comprises the steps of: reacting the raw material of o(p)-halogenated benzonitrile with an anhydrous alcohol solution of alkali metal alkoxide at a concentration of 5-50% for 1-24h in a mol ratio of 1:2-5, at a temperature of 100-250DEG C and under a pressure of 0.5-6MPa, then conducting temperature falling, cooling, reduced pressure distillation and exsolution, and adding hydrochloric acid for acidification, thus obtaining an o(p)-hydroxybenzonitrile solid. The method provided in the invention has cheap raw material, short reaction step, safe operation, high yield and less by-product, thus being suitable for business production.

Description

Technical field [0001] The invention relates to a chemical synthesis method, in particular to a method for preparing o-(p-hydroxybenzonitrile), an important fine chemical intermediate widely used in the fields of medicine and pesticides. Background technique [0002] Ortho(p)Hydroxybenzonitrile is an important fine chemical intermediate. Ortho-hydroxybenzonitrile (also known as salicylic nitrile) can be used to produce bunolol hydrochloride, which belongs to β-blockers. Mainly used for atrial fibrillation; supraventricular tachycardia and other arrhythmias; treatment of angina and hypertension. P-Hydroxybenzonitrile can be used to produce benzonitrile pesticides such as "Fencitrile", "Phosphos", "Bromobenzonitrile", "Hydroxylanil", "Baijunqing" etc. It can also be used in the field of liquid crystal materials and perfumes. [0003] At present, the preparation methods of o-(p-)hydroxybenzonitrile developed in the world mainly include hydroxybenzaldehyde method, hydroxybenzoic aci...

Claims

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Application Information

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IPC IPC(8): C07C255/53C07C253/30
Inventor 樊小彬王萍李利奎黄超习培华范晶
Owner JIANGSU LIANHE CHEM TECH