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Preparation method of 2-isopropylthioxanthone

A technology of isopropylthioxanthone and propylthiophenol is applied in the field of preparation of 2-isopropylthioxanthone, and can solve the problems of high energy consumption, low efficiency, and unsuitability for large-scale popularization and use. , to achieve the effect of low energy consumption and high efficiency

Active Publication Date: 2011-09-07
江西扬帆新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] CN200810025425.2 reported the method of etherifying o-chlorobenzoic acid, 4-isopropylthiophenol and lithium hydroxide in tetralin, and then cyclizing in concentrated sulfuric acid to prepare 2-isopropylthioxanthone ; Tetrahydronaphthalene and lithium hydroxide that this method needs are expensive, so they are not suitable for large-scale popularization and use
CN201010168358.7 replaces lithium hydroxide with sodium hydroxide; but it needs pressurization and high temperature reaction, has high requirements on equipment, and has great potential safety hazards
CN201010190953.0 replaces lithium hydroxide with copper powder; but the reaction temperature is high, the reaction time is long, and there are disadvantages such as low efficiency and large energy consumption
Documents (Journal of Industrial and Engineering Chemistry (Seoul), 6(6), 431-436; 2000) have been reported to prepare 2-isopropylthioxanthone with anthranilic acid as a raw material. Aminobenzoic acid is converted into o-mercaptobenzoic acid and then cyclized with cumene. This process uses a metal reducing agent and produces a large amount of sewage containing metal ions, which is not conducive to environmental protection.

Method used

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  • Preparation method of 2-isopropylthioxanthone
  • Preparation method of 2-isopropylthioxanthone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1, a kind of preparation method of 2-isopropylthioxanthone, carries out following steps successively:

[0024] 1), diazotization reaction: add 30ml water, 13.7g (0.1mol) anthranilic acid, 30.4g (0.25mol, mass concentration 30%) industrial hydrochloric acid under stirring in 250ml three-necked flask, cool to 0 ℃, control 7.4g (0.107mol) of sodium nitrite in 20ml of aqueous solution was added dropwise at 0-5°C. After the dropwise addition was completed, the temperature was controlled at 0-5°C for 30 minutes to obtain the diazonium salt for later use.

[0025] 2), Condensation etherification reaction: Add 80ml of water, 12g (0.3mol) sodium hydroxide, 15.2g (0.1mol) 4-isopropylthiophenol into a 500ml three-necked flask with stirring, stir to dissolve, and control the temperature for 5- Add all the diazonium salt obtained in step 1) dropwise at 15°C, after the dropwise addition is completed, heat up to room temperature at 30-35°C and react for 3h, slowly add 25g (...

Embodiment 2

[0028] The preparation method of embodiment 2,2-isopropylthioxanthone, carries out the following steps successively:

[0029] 1), diazotization reaction: add 30ml water, 13.7g (0.1mol) anthranilic acid, 30.4g (0.25mol, mass concentration 30%) industrial hydrochloric acid under stirring in 250ml three-necked flask, cool to 0 ℃, control 7.4g (0.107mol) of sodium nitrite in 20ml of aqueous solution was added dropwise at 0-5°C. After the dropwise addition was completed, the temperature was controlled at 0-5°C for 30 minutes to obtain the diazonium salt for later use.

[0030] 2) Condensation etherification reaction: Add 80ml of water, 12g (0.3mol) of sodium hydroxide, 15.2g (0.1mol) of 4-isopropylthiophenol into a 500ml three-necked flask with stirring, stir to dissolve, and control the temperature at room temperature for 30 Add dropwise the diazonium salt obtained in step 1) at -35°C, after the dropwise addition, react at room temperature for 3h at 30-35°C, slowly add 25g (mass c...

Embodiment 3-6

[0033] Embodiment 3-6: Change reaction temperature T1 and reaction time t1, 4-isopropylthiophenol addition n1, step 3) in step 2) reaction time t2 in reaction temperature T1, obtain 2-odor propyl thioxanthone The total molar yield of is y, and the specific data results are shown in Table 1.

[0034] Example

[0035] n1,mol

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Abstract

The invention discloses a preparation method of 2-isopropylthioxanthone. The method comprises the following steps: 1) performing diazotization reaction: using anthranilic acid, inorganic acid and sodium nitrite to react in water at 0-5 DEG C for 20-40 minutes and obtain diazonium salt; 2) performing condensation etherification reaction: using inorganic alkali, 4-isopropylthiophenol and the diazonium salt obtained in the step 1) to react in water at 0-70 DEG C for 2-4 hours; then adjusting the pH value to 3 with inorganic acid, filtering to obtain the solid; 3) performing dehydration cyclization reaction: placing the solid obtained in the step 2) in concentrated sulphuric acid of which mass concentration is no less than 97%, to react at 20-25 DEG C for 1-3 hours; and 4) reducing the temperature of the product obtained in the step 3), rinsing, filtering, and adding alkaline solution to layer and obtain 2-isopropylthioxanthone. The 2-isopropylthioxanthone prepared by the method is characterized by high efficiency and low energy consumption.

Description

technical field [0001] The invention relates to a preparation method of 2-isopropylthioxanthone. Background technique [0002] 2-isopropylthioxanthone as shown in formula I is a UV-curable photoinitiator, which is widely used in inks, adhesives, electronic products, automotive coatings and the like. [0003] [0004] Formula I [0005] CN200810025425.2 reported the method of etherifying o-chlorobenzoic acid, 4-isopropylthiophenol and lithium hydroxide in tetralin, and then cyclizing in concentrated sulfuric acid to prepare 2-isopropylthioxanthone ; Tetrahydronaphthalene, Lithium Hydroxide that this method needs are expensive, therefore are not suitable for large-scale popularization and use. CN201010168358.7 replaces lithium hydroxide with sodium hydroxide; however, it requires pressurized and high-temperature reaction, requires high equipment, and has great potential safety hazards. CN201010190953.0 replaces lithium hydroxide with copper powder; but the reaction tempe...

Claims

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Application Information

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IPC IPC(8): C07D335/16
Inventor 廖祖态袁继新吕雪皓陈育亮陶明钱超陈新志
Owner 江西扬帆新材料有限公司
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