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Preparation method of free radical initiator and application of free radical initiator in oxidation reaction

An oxidation reaction and initiator technology, which is applied in the field of free radical initiator preparation, can solve the problems of refractory organic compounds, high N/C, stimulation, etc., and achieve good preparation repeatability, high separation yield and purity, and raw materials simple effect

Pending Publication Date: 2021-11-05
WUHAN QIANGFENG XINTE TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Literature (Molecular Catalysis, 2007, 21 (2): 97-98) reported that tetrachlorophthalic anhydride and hydroxylamine hydrochloride were used as substrates, and triethylamine was used as a promoter to prepare TCNHPI, wherein triethylamine belongs to organic amines It is highly alkaline, toxic, and a small amount of inhalation has a strong irritating effect on the eyes and upper respiratory tract. It is a refractory organic compound and is expensive. Triethylamine wastewater is toxic wastewater with high N / C and is relatively difficult. deal with

Method used

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  • Preparation method of free radical initiator and application of free radical initiator in oxidation reaction
  • Preparation method of free radical initiator and application of free radical initiator in oxidation reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Under the condition of an ice-water bath, add 2.2g of hydroxylamine sulfate, 2.2g of anhydrous sodium carbonate, and 150mL of water into the flask, stir and dissolve, react for 1.5h, then add 6.0g of tetrachlorophthalic anhydride, and stir for 1.0h at room temperature , then raise the temperature to 85°C, and continue the reaction for 12h. After the reaction, cool, filter, wash with water, and dry at 60°C for 12h, then use a mixed solvent of toluene and ethanol (1:1) to recrystallize, filter, and After drying for 12 hours, light brown TCNHPI was obtained, with a melting point of 238°C, a yield of 90.4%, and a purity of 99.1%.

[0029] The TCNHPI prepared in this embodiment is used as an initiator, the above-mentioned loaded multi-metal oxide is used as a catalyst, and glacial acetic acid is used as a solvent to evaluate its catalyzed recycling performance of molecular oxygen oxidation of 2-chloro-4-thiamphenicol toluene, specifically Proceed as follows:

[0030] Put 20...

Embodiment 2

[0032]Under the condition of ice-water bath, add 2.2g of hydroxylamine sulfate, 1.6g of anhydrous sodium carbonate, and 240mL of water into the flask, stir and dissolve, react for 3.0h, then add 6.0g of tetrachlorophthalic anhydride, and stir for 2.0h at room temperature , then raise the temperature to 90°C, and continue the reaction for 8h. After the reaction, cool, filter, wash with water, and dry at 60°C for 12h, then recrystallize with a mixed solvent of toluene and ethanol (1:1), filter, and dry at 60°C After drying for 24 hours, light brown TCNHPI was obtained, with a melting point of 239°C, a yield of 89.0%, and a purity of 99.4%.

[0033] The TCNHPI prepared in this embodiment is used as an initiator, the above-mentioned loaded multi-metal oxide is used as a catalyst, and glacial acetic acid is used as a solvent to evaluate its catalyzed recycling performance of molecular oxygen oxidation of 2-chloro-4-thiamphenicol toluene, specifically Proceed as follows:

[0034] P...

Embodiment 3

[0036] Under the condition of an ice-water bath, add 1.9g of hydroxylamine sulfate, 1.7g of anhydrous sodium carbonate, and 180mL of water into the flask and stir to dissolve, react for 2.0h, then add 6.0g of tetrachlorophthalic anhydride, and stir for 4.0h at room temperature , then raise the temperature to 75°C, and continue the reaction for 16h. After the reaction, cool, filter, wash with water, and dry at 60°C for 12h, then use a mixed solvent of toluene and ethanol (1:1) to recrystallize, filter, and dry After drying for 12 hours, light brown TCNHPI was obtained, with a melting point of 237°C, a yield of 89.6%, and a purity of 98.8%.

[0037] The TCNHPI prepared in this embodiment is used as an initiator, the above-mentioned loaded multi-metal oxide is used as a catalyst, and glacial acetic acid is used as a solvent to evaluate its catalyzed recycling performance of molecular oxygen oxidation of 2-chloro-4-thiamphenicol toluene, specifically Proceed as follows:

[0038] ...

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Abstract

The invention discloses a preparation method of a free radical initiator, the preparation method comprises the following steps: feeding a hydroxylamine raw material, inorganic base and water according to a ratio, and carrying out acid-base neutralization reaction at 0-25 DEG C to dissociate hydroxylamine; adding tetrachlorophthalic anhydride, stirring at room temperature to react for 0.5-2 hours, reacting at 60-95 DEG C for 4-12 hours, washing with water, and drying at 60-80 DEG C for 10-24 hours to obtain an N-hydroxyl tetrachlorophthalimide crude product; and recrystallizing the N-hydroxyl tetrachlorophthalimide crude product in a mixed solvent of toluene and ethanol, filtering, and drying at 60-80 DEG C to obtain the N-hydroxyl tetrachlorophthalimide free radical initiator. According to the method, the adopted raw materials are simple, the conditions are easy to control, the preparation technology is green and environmentally friendly, the preparation repeatability is good, the free radical initiator is used in the oxidation reaction, a high-purity and high-yield product can be obtained, and the product obtained after repeated use still has high separation yield and purity.

Description

technical field [0001] The invention relates to the technical field of free radical initiator preparation, in particular to a recyclable free radical initiator and its application in oxidation reaction. Background technique [0002] The selective oxidation of alkylbenzene and molecular oxygen is a very important selective oxidation reaction for the production of bulk chemicals and fine chemicals, such as benzoic acid and terephthalic acid. At present, transition metals (such as organic acid salts of cobalt, manganese, etc.) and oxidation promoters (bromide) are widely used as catalysts in industry. equipment, and will also cause a certain degree of environmental pollution. [0003] In recent years, the application of N-hydroxyphthalimide (NHPI) and its analogues in organic oxidation reactions has attracted great attention. They are widely used as electrochemical oxidation substrates or catalysts in the oxidation reactions of aromatics, alkanes, alkenes, alkynes, alcohols, ...

Claims

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Application Information

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IPC IPC(8): C07D209/48C07B61/00C07C315/04C07C317/44
CPCC07D209/48C07B61/02C07C315/04C07C317/44
Inventor 李雄李颢吴革晓
Owner WUHAN QIANGFENG XINTE TECH
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