Method for preparing salicylaldehyde by oxidizing saligenol selectively catalyzed by molecular oxygen

A technology of salicyl alcohol and molecular oxygen, which is applied to the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds. It can solve the problems of many by-products, high cost, and low yield, and achieve low cost and pollution. Small size and high reaction efficiency

Active Publication Date: 2013-04-03
张家港市飞航科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The purpose of the present invention is to overcome technical problems such as low yield, high cost, many by-products and serious pollution in the existing salicylaldehyde preparation method, and provide a method for preparing salicylaldehyde by selective catalytic molecular oxygen oxidation of salicylalcohol

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The feed ratio is as follows: salicyl alcohol: 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO): sodium bromide-sodium bromate combination: sodium nitrite: sulfuric acid with a molar ratio of 1 :0.01:0.048:0.08:0.075, wherein the molar ratio of sodium bromide-sodium bromate combination is 5:1:

[0028] Add 0.62g (5mmol) salicyl alcohol, 0.0078g (0.05mmol) TEMPO, 0.021g (0.2mmol) NaBr, 0.0063g (0.04mmol) NaBrO to a 50ml Erlenmeyer flask 3 , 5ml 1,2-dichloroethane, 0.5ml water, add 0.018ml concentrated sulfuric acid dropwise, stir for 5 minutes, then add 0.0276g (0.4mmol) NaNO2, react at 25°C for 7 hours in an air atmosphere, and analyze by gas chromatography Product composition. After the reaction, the reaction solution was washed with saturated Na 2 S 2 o 3 The solution is washed, acidified, extracted, dried, and then distilled at atmospheric pressure to remove the solvent, and then distilled with a vacuum distillation device to collect fractions at about 84-86 ...

Embodiment 2

[0030] The feed ratio is as follows: salicyl alcohol: 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO): sodium bromide-sodium bromate combination: sodium nitrite: hydrochloric acid with a molar ratio of 1 :0.01:0.04:0.08:0.06, wherein the molar ratio of sodium bromide-sodium bromate combination is 5:1:

[0031]Add 0.62g (5mmol) salicyl alcohol, 0.0078g (0.05mmol) TEMPO, 0.016g (0.16mmol) NaBr, 0.0063g (0.04mmol) NaBrO to a 50ml Erlenmeyer flask 3 , 5ml dichloromethane, 1ml water, dropwise added 0.014ml hydrochloric acid, stirred for 15 minutes, then added 0.0276g (0.4mmol) NaNO 2 , reacted at 10°C for 12 hours under an oxygen atmosphere, and analyzed the composition of the product by gas chromatography. After the reaction, the reaction solution was washed with saturated Na 2 S 2 o 3 The solution is washed, acidified, extracted, dried, and then distilled at atmospheric pressure to remove the solvent, and then distilled with a vacuum distillation device to collect fracti...

Embodiment 3

[0033] The feed ratio is as follows: salicyl alcohol: 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO): sodium bromide-sodium bromate combination: sodium nitrite: sulfuric acid with a molar ratio of 1 :0.01:0.01:0.1:0.015, wherein the molar ratio of sodium bromide-sodium bromate combination is 3:1:

[0034] Add 0.62g (5mmol) salicyl alcohol, 0.0078g (0.05mmol) TEMPO, 0.0039g (0.0375mmol) NaBr, 0.0019g (0.0125mmol) NaBrO to a 50ml Erlenmeyer flask 3 , 5ml acetonitrile, 0.5ml water, dropwise add 0.004ml concentrated sulfuric acid, stir for 10 minutes, then add 0.035g (0.5mmol) NaNO 2 , reacted at 80°C for 15 hours under an air atmosphere, and analyzed the composition of the product by gas chromatography. After the reaction, the reaction solution was washed with saturated Na 2 S 2 o 3 The solution is washed, acidified, extracted, dried, and then distilled at atmospheric pressure to remove the solvent, and then distilled with a vacuum distillation device to collect fractio...

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PUM

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Abstract

The invention relates to a method for preparing salicylaldehyde by oxidizing saligenol selectively catalyzed by molecular oxygen, and belongs to the technical field of catalysts. In the method, saligenol is used as a raw material, the used catalyst is composed of the following components of (A) 2,2,6,6-tetramethyl piperidine-N-oxygen radical (TEMPO), 4-benzoyl-2,2,6,6-tetramethyl piperidine-N-oxygen radical or 4-acetyl-2,2,6,6-tetramethyl piperidine-N-oxygen radical; (B) a brominated salt-bromate salt combination; (C) a nitrite salt; and (D) sulfuric acid, hydrochloric acid, nitric acid or phosphoric acid; and the catalytic oxidation reaction is carried out at a temperature of 10-80 DEG C under an air atmosphere. The method has the following advantages that (1) reaction condition is mild, catalytic activity is high, reaction efficiency is high, and selectivity of a product is high; (2) transition metals particularly precious metal compounds are prevented from use in the catalytic system, the catalytic system is low in cost, is safe and convenient and has small pollutions; and (3) the used inorganic components of the brominated salt-bromate salt combination and the nitrite salt are low in cost and easy to obtain, and the post-treatment after reaction is easy.

Description

technical field [0001] The invention relates to a preparation method of salicylaldehyde, in particular to a method for preparing salicylaldehyde by selectively catalyzing molecular oxygen oxidation of salicyl alcohol. Background technique [0002] Salicylaldehyde, also known as o-hydroxybenzaldehyde, is a fine chemical product with a wide range of uses, widely used in the production of pesticides, medicines, and integrative agents; low concentrations of salicylaldehyde have a strong ability to inhibit bacteria Active ability, can be used as a preservative; it can be used as a stabilizer in the plastic resin industry; it is used in the fragrance industry to synthesize coumarin and is widely used in soap, detergent, blended spices, candy and tobacco industries; salicyl Aldehyde can form a chelating agent with a variety of metals. Salicylaldehyde is used as a brightener and leveling agent in the electroplating industry; in the petroleum industry, many adducts of salicylaldehyde...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/565C07C45/38
Inventor 韩世清张杰蒋增强赵丹何国珍周双利
Owner 张家港市飞航科技有限公司
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