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Solid acid based catalytic synthesis method for photoinitiator DETX (2,4-diethyl thioxanthone)

A solid acid catalyst and solid acid catalysis technology, applied in the direction of organic chemistry, can solve the problems of production equipment corrosion, post-processing difficulty, low product yield, etc., and achieve production cost reduction, raw material cost reduction, and simple post-processing Effect

Inactive Publication Date: 2018-08-21
JIAN DONGQING FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the production process of 2,4-diethylthioxanthone mainly uses concentrated sulfuric acid as solvent and catalyst simultaneously (J.Chem.Soc.1911,99,645, JPS 57163377 and CN 102250060 all adopt this process), not only side reactions Many (especially some sulfonated aromatic compounds), the appearance of the product is poor, the product yield is low (about 80%), and the post-treatment is very difficult. While producing a large amount of waste acid, it also causes great corrosion to the production equipment , neither environmentally friendly nor economical

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) Condensation ring reaction: under the condition that the temperature is 100°C, 25g of dithiosalicylic acid, 26g of m-diethylbenzene, and 3g of strongly acidic cation exchange resin are added to a reaction kettle containing 75ml of dimethyl sulfoxide middle reaction;

[0020] (2) HPLC carries out follow-up reaction, after dithiosalicylic acid disappears, the reaction solution is cooled to room temperature, filters, and after the filtrate is concentrated under reduced pressure to remove solvent, adds 100g toluene extraction, divides and removes the water layer, and the organic layer is watered respectively After washing with saturated brine, the toluene was distilled off under reduced pressure, and then the resulting residue was recrystallized with 95% ethanol, and finally filtered and dried to obtain 38.9 g of yellow crystalline powder, which was photoinitiator 2 ,4-Diethylthioxanthone.

[0021] Experimental results: the yield of the product is 88.9%, the melting po...

Embodiment 2

[0023] (1) Condensation ring reaction: under the condition that the temperature is 100°C, 25g dithiosalicylic acid, 26g m-diethylbenzene, 1.5g solid superacid SO 4 2- / TiO 2 Join in the reaction kettle that contains 75ml dimethyl sulfoxide;

[0024] (2) HPLC carries out follow-up reaction, after dithiosalicylic acid disappears, the reaction solution is cooled to room temperature, filters, and after the filtrate is concentrated under reduced pressure to remove solvent, adds 100g toluene extraction, divides and removes the water layer, and the organic layer is watered respectively After washing with saturated brine, the toluene was distilled off under reduced pressure, and then the resulting residue was recrystallized with 95% ethanol, and finally filtered and dried to obtain 37.2 g of yellow crystalline powder, which was photoinitiator 2 ,4-Diethylthioxanthone.

[0025] Experimental results: the yield of the product is 85.0%, the melting point is 70-72°C, and the purity of t...

Embodiment 3

[0027] (1) Condensation ring reaction: under the condition of 100°C, 22g dithiosalicylic acid, 23g m-diethylbenzene, 1.3g solid acid SO 4 2- / TiO 2 Add to contain 70mlN, react in the reactor of N-dimethylacetamide;

[0028] (2) HPLC carries out follow-up reaction, after dithiosalicylic acid disappears, the reaction solution is cooled to room temperature, filters, and after the filtrate is concentrated under reduced pressure to remove solvent, adds 100g toluene extraction, divides and removes the water layer, and the organic layer is watered respectively After washing with saturated brine, the toluene was distilled off under reduced pressure, and then the resulting residue was recrystallized with 95% ethanol, and finally filtered and dried to obtain 36.3 g of yellow crystalline powder, which was photoinitiator 2 ,4-Diethylthioxanthone.

[0029] Experimental results: the yield of the product is 86.2%, the melting point is 70-72°C, and the purity of the product detected by HPL...

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PUM

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Abstract

The invention discloses a solid acid based catalytic synthesis method for photoinitiator DETX (2,4-diethyl thioxanthone). According to the method, solid acid is taken as a catalyst, dithiosalicylic acid and m-diethylbenzene are added to a reaction kettle containing an organic solvent for a reaction, and the required product, namely, the photoinitiator DETX is obtained through extraction, recrystallization, filtering and drying. Compared with the prior art, the yield is increased, side reactions are reduced greatly, and the method is suitable for industrialization and environmentally friendly.

Description

technical field [0001] The invention relates to the field of photoinitiators, in particular to a method for solid acid catalyzed synthesis of photoinitiator 2,4-diethylthioxanthone. Background technique [0002] 2,4-Diethyl Thioxanthone, English name 2,4-Diethyl Thioxanthone (DETX for short), molecular formula: C 17 h 16 OS, molecular weight: 268.37, CAS registry number: [82799-44-8]. 2,4-Diethylthioxanthone is light yellow crystalline powder, melting point: 70~71℃. As an important photoinitiator, 2,4-diethylthioxanthone is widely used in UV-curable coatings and inks. [0003] At present, the production process of 2,4-diethylthioxanthone mainly uses concentrated sulfuric acid as solvent and catalyst simultaneously (J.Chem.Soc.1911,99,645, JPS 57163377 and CN 102250060 all adopt this process), not only side reactions Many (especially some sulfonated aromatic compounds), the appearance of the product is poor, the product yield is low (about 80%), and the post-treatment is ...

Claims

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Application Information

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IPC IPC(8): C07D335/16
CPCC07D335/16
Inventor 曾孝军
Owner JIAN DONGQING FINE CHEM
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